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Sample records for acrylated epoxidized soybean

  1. Biobased composites from thermoplastic polyurethane elastomer and cross-linked acrylated-epoxidized soybean oil

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean oil is an important sustainable material. Crosslinked acrylated epoxidized soybean oil (AESO) is brittle without flexibility and the incorporation of thermoplastic polyurethane improves its toughness for industrial applications. The hydrophilic functional groups from both oil and polyurethan...

  2. 4D printing smart biomedical scaffolds with novel soybean oil epoxidized acrylate

    PubMed Central

    Miao, Shida; Zhu, Wei; Castro, Nathan J.; Nowicki, Margaret; Zhou, Xuan; Cui, Haitao; Fisher, John P.; Zhang, Lijie Grace

    2016-01-01

    Photocurable, biocompatible liquid resins are highly desired for 3D stereolithography based bioprinting. Here we solidified a novel renewable soybean oil epoxidized acrylate, using a 3D laser printing technique, into smart and highly biocompatible scaffolds capable of supporting growth of multipotent human bone marrow mesenchymal stem cells (hMSCs). Porous scaffolds were readily fabricated by simply adjusting the printer infill density; superficial structures of the polymerized soybean oil epoxidized acrylate were significantly affected by laser frequency and printing speed. Shape memory tests confirmed that the scaffold fixed a temporary shape at −18 °C and fully recovered its original shape at human body temperature (37 °C), which indicated the great potential for 4D printing applications. Cytotoxicity analysis proved that the printed scaffolds had significant higher hMSC adhesion and proliferation than traditional polyethylene glycol diacrylate (PEGDA), and had no statistical difference from poly lactic acid (PLA) and polycaprolactone (PCL). This research is believed to significantly advance the development of biomedical scaffolds with renewable plant oils and advanced 3D fabrication techniques. PMID:27251982

  3. 4D printing smart biomedical scaffolds with novel soybean oil epoxidized acrylate.

    PubMed

    Miao, Shida; Zhu, Wei; Castro, Nathan J; Nowicki, Margaret; Zhou, Xuan; Cui, Haitao; Fisher, John P; Zhang, Lijie Grace

    2016-06-02

    Photocurable, biocompatible liquid resins are highly desired for 3D stereolithography based bioprinting. Here we solidified a novel renewable soybean oil epoxidized acrylate, using a 3D laser printing technique, into smart and highly biocompatible scaffolds capable of supporting growth of multipotent human bone marrow mesenchymal stem cells (hMSCs). Porous scaffolds were readily fabricated by simply adjusting the printer infill density; superficial structures of the polymerized soybean oil epoxidized acrylate were significantly affected by laser frequency and printing speed. Shape memory tests confirmed that the scaffold fixed a temporary shape at -18 °C and fully recovered its original shape at human body temperature (37 °C), which indicated the great potential for 4D printing applications. Cytotoxicity analysis proved that the printed scaffolds had significant higher hMSC adhesion and proliferation than traditional polyethylene glycol diacrylate (PEGDA), and had no statistical difference from poly lactic acid (PLA) and polycaprolactone (PCL). This research is believed to significantly advance the development of biomedical scaffolds with renewable plant oils and advanced 3D fabrication techniques.

  4. 4D printing smart biomedical scaffolds with novel soybean oil epoxidized acrylate.

    PubMed

    Miao, Shida; Zhu, Wei; Castro, Nathan J; Nowicki, Margaret; Zhou, Xuan; Cui, Haitao; Fisher, John P; Zhang, Lijie Grace

    2016-01-01

    Photocurable, biocompatible liquid resins are highly desired for 3D stereolithography based bioprinting. Here we solidified a novel renewable soybean oil epoxidized acrylate, using a 3D laser printing technique, into smart and highly biocompatible scaffolds capable of supporting growth of multipotent human bone marrow mesenchymal stem cells (hMSCs). Porous scaffolds were readily fabricated by simply adjusting the printer infill density; superficial structures of the polymerized soybean oil epoxidized acrylate were significantly affected by laser frequency and printing speed. Shape memory tests confirmed that the scaffold fixed a temporary shape at -18 °C and fully recovered its original shape at human body temperature (37 °C), which indicated the great potential for 4D printing applications. Cytotoxicity analysis proved that the printed scaffolds had significant higher hMSC adhesion and proliferation than traditional polyethylene glycol diacrylate (PEGDA), and had no statistical difference from poly lactic acid (PLA) and polycaprolactone (PCL). This research is believed to significantly advance the development of biomedical scaffolds with renewable plant oils and advanced 3D fabrication techniques. PMID:27251982

  5. Biorenewable tough blends of polylactide and acrylated epoxidized soybean oil compatibilized by a polylactide star polymer

    DOE PAGES

    Mauck, Sheli C.; Wang, Shu; Ding, Wenyue; Rohde, Brian J.; Fortune, C. Karen; Yang, Guozhen; Robertson, Megan L.; Ahn, Suk -Kyun

    2016-02-26

    Polylactide (PLA), a commercially available thermoplastic derived from plant sugars, finds applications in consumer products, disposable packaging, and textiles, among others. The widespread application of this material is limited by its brittleness, as evidenced by low tensile elongation at break, impact strength, and fracture toughness. Herein, a multifunctional vegetable oil, acrylated epoxidized soybean oil (AESO), was investigated as a biodegradable, renewable additive to improve the toughness of PLA. AESO was found to be a highly reactive oil, providing a dispersed phase with tunable properties in which the acrylate groups underwent cross-linking at the elevated temperatures required for processing the blends.more » Additionally, the presence of hydroxyl groups on AESO provided two routes for compatibilization of PLA/AESO blends: (1) reactive compatibilization through the transesterification of AESO and PLA and (2) synthesis of a PLA star polymer with an AESO core. The morphological, thermal, and mechanical behaviors of PLA/oil blends were investigated, in which the dispersed oil phase consisted of AESO, soybean oil (SYBO), or a 50/50 mixture of AESO/SYBO. The oil additives were found to toughen the PLA matrix, with significant enhancements in the elongation at break and tensile toughness values, while maintaining the glass transition temperature of neat PLA. Specifically, the blend containing PLA, AESO, SYBO, and the PLA star polymer was found to exhibit a uniform oil droplet size distribution with small average droplet size and interparticle distance, resulting in the greatest enhancements of PLA tensile properties with no observable plasticization.« less

  6. Thermodynamics of coil-hyperbranched poly(styrene-b-acrylated epoxidized soybean oil) block copolymers

    NASA Astrophysics Data System (ADS)

    Lin, Fang-Yi; Hohmann, Austin; Hernández, Nacú; Cochran, Eric

    Here we present the phase behavior of a new type of coil-hyperbranched diblock copolymer: poly(styrene- b-acrylated epoxidized soybean oil), or PS-PAESO. PS-PAESO is an example of a biorenewable thermoplastic elastomer (bio-TPE). To date, we have shown that bio-TPEs can be economical commercial substitutes for their petrochemically derived analogues--such as poly(styrene- b-butadiene- b-styrene) (SBS)--in a range of applications including pressure sensitive adhesives and bitumen modification. From a polymer physics perspective, PS-PAESO is an interesting material in that it couples a linear coil-like block with a highly branched block. Thus in contrast to the past five decades of studies on linear AB diblock copolymers, coil-hyperbranched block copolymers are relatively unknown to the community and can be expected to deviate substantially from the standard ``universal'' phase behavior in the AB systems. To explore these new materials, we have constructed a library of PS-PAESO materials spanning a range of molecular weight and composition values. The phase transition behavior and the morphology information will be interpreted by isochronal temperature scanning in dynamic shear rheology, small angle X-ray scattering and the corresponding transmission electron microscopy.

  7. Optical properties and indentation hardness of thin-film acrylated epoxidized oil

    NASA Astrophysics Data System (ADS)

    Rahman, Mohammad Syuhaimi Ab.; Shaktur, Khaled Mohamed; Mohammad, Rahmah; Zalikha, Wan Aimi; Nawi, Norwimie; Mohd, Ahmad Faiza

    2012-02-01

    Epoxy acrylate has been widely used as optical resin for applications such as cladding, the core of a waveguide, and other photonic devices. In this study, sustainable resin from edible oil was used as an alternative to epoxy acrylate. Structural features and the transmission of planar thin-film resin from an ultraviolet-visible spectroscopy (UV-VIS) spectrometer were investigated upon UV exposure. It was found that high transmission still persists for all samples with and without an UV absorber for exposed and unexposed samples. The film was found to absorb strongly below 400 nm. A change in the cut-off wavelength was observed upon exposure. Thin-film hardness and its dynamic indentation in the load-unload mode with different test forces were evaluated. Vickers hardness and the elastic modulus were determined for unacrylated epoxidized soybean oil (ESO) and acrylated epoxidized soybean oil (AESO). It was found that the AESO has a higher Vickers hardness and elastic modulus than those of unacrylated thin film. The Vickers hardness and elastic modulus were found to increase as the applied test force increased. The refractive index, thickness, and modes present were characterized from a spin-coated planar thin film. The refractive index in the transverse electric mode (TE) and transverse magnetic mode (TM) were determined and compared for unacrylated and acrylated epoxidized oil.

  8. 40 CFR 721.10210 - Soybean oil, epoxidized, reaction products with diethanolamine.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Soybean oil, epoxidized, reaction... Significant New Uses for Specific Chemical Substances § 721.10210 Soybean oil, epoxidized, reaction products... chemical substance identified as soybean oil, epoxidized, reaction products with diethanolamine (PMN...

  9. 40 CFR 721.10210 - Soybean oil, epoxidized, reaction products with diethanolamine.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Soybean oil, epoxidized, reaction... Significant New Uses for Specific Chemical Substances § 721.10210 Soybean oil, epoxidized, reaction products... chemical substance identified as soybean oil, epoxidized, reaction products with diethanolamine (PMN...

  10. 40 CFR 721.10210 - Soybean oil, epoxidized, reaction products with diethanolamine.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Soybean oil, epoxidized, reaction... Significant New Uses for Specific Chemical Substances § 721.10210 Soybean oil, epoxidized, reaction products... chemical substance identified as soybean oil, epoxidized, reaction products with diethanolamine (PMN...

  11. 40 CFR 721.10210 - Soybean oil, epoxidized, reaction products with diethanolamine.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Soybean oil, epoxidized, reaction... Significant New Uses for Specific Chemical Substances § 721.10210 Soybean oil, epoxidized, reaction products... chemical substance identified as soybean oil, epoxidized, reaction products with diethanolamine (PMN...

  12. Toughening of epoxy resins by epoxidized soybean oil

    SciTech Connect

    Frischinger, I.; Dirlikov, S.

    1993-12-31

    Homogeneous mixtures of a liquid rubber based on prepolymers of epoxidized soybean oil with amines, diglycidyl ether of bisphenol A epoxy resins, and commercial diamines form, under certain conditions, two-phase thermosetting materials that consist of a rigid epoxy matrix and randomly distributed small rubbery soybean particles (0.1-5 {mu}m). These two-phase thermosets have improved toughness, similar to that of other rubber-modified epoxies, low water absorption, and low sodium content. In comparison to the unmodified thermosets, the two-phase thermosets exhibit slightly lower glass-transition temperatures and Young`s moduli, but their dielectric properties do not change. The epoxidized soybean oil is available at a price below that of commercial epoxy resins and appears very attractive for epoxy toughening on an industrial scale. 15 refs., 17 figs., 6 tabs.

  13. UV-curable acrylated coating from epoxidized palm oil

    NASA Astrophysics Data System (ADS)

    Rahman, Nurliyana Abd; Badri, Khairiah Haji; Salleh, Nik Ghazali Nik

    2014-09-01

    The properties of coating film prepared from the incorporation of acrylated palm oil (EPOLA) in commercial epoxy acrylate have been studied. A series of different amount of EPOLA was mixed with commercial epoxy acrylate. The blended acrylates passed through UV light to produce a non-tacky film. The conversion of acrylate double bond was monitored by FTIR. The effect of EPOLA concentration onto coated films were investigated by determination of the pendulum hardness and gel content. The higher the amount of EPOLA, the lower the pendulum hardness and the gel content but to a level acceptable for usage in the high-end applications.

  14. [Determination of epoxidized soybean oil in bottled foods].

    PubMed

    Kawamura, Yoko; Kanno, Shinji; Mutsuga, Motoh; Tanamoto, Kenichi

    2006-12-01

    A determination method for epoxidized soybean oil (ESBO) in bottled foods was developed and used to survey bottled foods on the Japanese market. The amount of sample required was decreased to 20 g and the standard addition method was adopted for the quantification, because lipid in foods interrupted the hydrolysis of ESBO. The recoveries were 87.1 and 98.9% and the determination limit was 5.0 microg/g for a 20 g sample, be cause lipid in foods interupted the hydrolysis of ESBO. The recoveries using the internal standard method varied widely, because hydrolysis of the internal standard, cis-11,14-eicosadienoic acid ethyl ester, was affected more than that of ESBO by coexisting lipid in the sample. ESBO was not detected in any of the bottled baby food samples examined (14 samples), though it had been frequently detected in previous European surveys. This difference may be related to the low fat content and low fluidity of the bottled baby foods retailed in Japan. On the other hand, ESBO was detected at levels of 25.7-494.0 microg/g in liver paste, pasta sauce, Sungan in spicy oil, and spicy oil. These foods had higher fat content and higher fluidity. However, ESBO intake from these foods appears unlikely to exceed the TDI in the EU (1 mg/kg bw/day). PMID:17228787

  15. Ternary liquid-liquid equilibria measurement for epoxidized soybean oil + acetic acid + water.

    PubMed

    Cai, Shuang-Fei; Wang, Li-Sheng; Yan, Guo-Qing; Li, Yi; Feng, Yun-Xia; Linghu, Rong-Gang

    2012-01-01

    Liquid-liquid equilibria (LLE) data were measured for ternary system epoxidized soybean oil (ESO) + acetic acid + water at 313.15, 323.15 and 333.15 K, respectively. The consistency of the measured LLE data was tested, using Othmer-Tobias correlation and root-mean-square deviation (sigma) in mass fraction of water in the lower phase and average value of the absolute difference (AAD) between experimental mass fraction of epoxidized soybean oil in the upper phase and that calculated using Othmer-Tobias correlation.

  16. Enzymatic epoxidation of soybean oil using ionic liquid as reaction media.

    PubMed

    Sun, Shangde; Li, Ping; Bi, Yanlan; Xiao, Fugang

    2014-01-01

    An ionic liquid (IL) system for the enzymatic epoxidation of soybean oil was studied. The effects of active oxygen carriers (different fatty acids) and ILs ([Bmim]PF6 and [Bmim]BF4) on the enzymatic epoxidation were investigated. Response surface methodology (RSM) was used to study and optimize the effects of variables (reaction time, reaction temperature, molar ratio of H2O2/C=C-bonds, and molar ratio of fatty acid/C=C-bonds) on the epoxy oxygen group content (EOC) of epoxidized soybean oil (ESO). Results showed that the enzymatic epoxidation of soybean oil can be enhanced using tetradecanoic acid (C13H27COOH) as active oxygen carrier and [Bmim]PF6 as reaction medium. The optimum EOC of ESO was 5.9 ± 0.3% under the following conditions: reaction temperature 46°C, reaction time 11 h, enzyme load 3% (w/w, relative to the weight of soybean oil), molar ratio of H2O2/C=C-bonds 1.8:1, and molar ratio of C13H27COOH/C=C-bonds 0.5:1.

  17. Application of hydrated and anhydrous fluroantimonic acids in the polymerization of epoxidized soybean oil

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Polymerizations of epoxidized soybean oil (ESO) were catalyzed by the superacids, fluroantimonic acid hexahydrate (HSbF6•6H2O) and anhydrous fluroantimonic acid (HSbF6) using ethyl acetate solvent. This work was conducted in an effort to develop useful biodegradable polymers from renewable resources...

  18. Boron Trifluoride Catalized Ring-Opening Polymerization of Epoxidized Soybean Oil in Liquid Carbon Dioxide

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Boron trifluoride diethyl etherate (BF3.OEt2) catalyzed ring-opening polymerization of epoxidized soybean oil (ESO), in liquid carbon dioxide, was conducted in an effort to develop useful biobased biodegradable polymers. The resulting polymers (RPESO) were characterized by FTIR spectroscopy, differ...

  19. Lewis Acid Catalyzed Ring-opening Polymerization of Epoxidized Soybean Oil in Liquid Carbon Dioxide

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ring-opening polymerization of epoxidized soybean oil (ESO) catalyzed by boron trifluoride diethyl etherate (BF3•OEt2), in liquid carbon dioxide, was conducted in an effort to develop useful biobased biodegradable polymers. The resulting polymers (RPESO) were characterized by FTIR spectroscopy, diff...

  20. Development of epoxidized soybean oil and soy fibre composites with Polyhedral Oligomeric Silsesquioxane (POSS) nano reinforcement

    NASA Astrophysics Data System (ADS)

    de Boer, Ryan Sietze

    Soy fibre and soybean oil were utilized to produce a bio-composite targeted as a substitute for conventional petroleum-based materials. The study was divided into two parts; the first was the development of a bio-epoxy that consisted of conventional epoxy, epoxidized soybean oil, and two types of functionalized POSS. The second part of the study involved blending of the bio-epoxy with titanate treated soy fibre. Combined incorporation of epoxide and amine functionalized POSS in the bio-epoxy matrix resulted in a 29% impact strength improvement compared to the petroleum-based epoxy. Incorporation of the epoxide functionalized POSS resulted in improvements in tensile strength by 8%, tensile modulus by 2%, and an increase in the glass transition temperature by 4% compared to the petroleum-based epoxy and epoxidized soybean oil hybrid. The coupling of titanate to soy fibre in comparison to the soy fibre without titanate treatment resulted in an impact strength improvement of 37%. Furthermore, the coupling of titanate increased the tensile strength and tensile modulus by 24% and 22% respectively, and reduced the water absorption by 70%.

  1. Gel Point Suppression in RAFT Polymerization of Pure Acrylic Cross-Linker Derived from Soybean Oil.

    PubMed

    Yan, Mengguo; Huang, Yuerui; Lu, Mingjia; Lin, Fang-Yi; Hernández, Nacú B; Cochran, Eric W

    2016-08-01

    Here we report the reversible addition-fragmentation chain transfer (RAFT) polymerization of acrylated epoxidized soybean oil (AESO), a cross-linker molecule, to high conversion (>50%) and molecular weight (>100 kDa) without macrogelation. Surprisingly, gelation is suppressed in this system far beyond the expectations predicated both on Flory-Stockmeyer theory and multiple other studies of RAFT polymerization featuring cross-linking moieties. By varying AESO and initiator concentrations, we show how intra- versus intermolecular cross-linking compete, yielding a trade-off between the degree of intramolecular linkages and conversion at gel point. We measured polymer chain characteristics, including molecular weight, chain dimensions, polydispersity, and intrinsic viscosity, using multidetector gel permeation chromatography and NMR to track polymerization kinetics. We show that not only the time and conversion at macrogelation, but also the chain architecture, is largely affected by these reaction conditions. At maximal AESO concentration, the gel point approaches that predicted by the Flory-Stockmeyer theory, and increases in an exponential fashion as the AESO concentration decreases. In the most dilute solutions, macrogelation cannot be detected throughout the entire reaction. Instead, cyclization/intramolecular cross-linking reactions dominate, leading to microgelation. This work is important, especially in that it demonstrates that thermoplastic rubbers could be produced based on multifunctional renewable feedstocks. PMID:27359245

  2. Epoxidation of soybean oil catalyzed by peroxo phosphotungstic acid supported on modified halloysite nanotubes

    NASA Astrophysics Data System (ADS)

    Jiang, Junqing; Zhang, Yanwu; Yan, Liwei; Jiang, Pingkai

    2012-06-01

    {PO4[W(O)(O2)2]4}3- was supported onto modified halloysite nanotubes (HNTs) to prepare heterogeneous catalysts and these catalysts were applied in epoxidation of soybean oil. To enhance the cohesive force between {PO4[W(O)(O2)2]4}3- and HNTs, quaternary amino groups were anchored onto HNTs through silylation of N-(2-aminoethyl)-3-aminopropyl trimethoxysilane and alkylation of amino groups. Further {PO4[W(O)(O2)2]4}3- was supported onto HNTs by ion exchange. The heterogeneous catalysts were characterized by FTIR, TGA, XRF and TEM-EDS. Then the catalytic behaviour to epoxidation of soybean oil was studied in detail. The results show that the introduction of phase transfer agent during preparation of the catalysts is very effective to improve catalytic activity and mechanical agitation combining with ultrasonic agitation is the best agitation way. The catalytic reactivity increased as reaction time increased. Moreover, the catalysts can be easily recovered from the reaction system by centrifugation as deposit and recycled three times without obviously decreasing the catalytic activity. Through re-exchange of {PO4[W(O)(O2)2]4}3-, the heterogeneous catalyst can be regenerated without catalytic activity loss.

  3. INVESTIGATION OF THE SURFACE PROPERTIES OF POLYMERIC SOAPS OBTAINED BY RING-OPENING POLYMERIZATION OF EPOXIDIZED SOYBEAN OIL

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Epoxidized soybean oil (ESO) was converted to a polysoap via a two-step synthetic procedure of catalytic ring-opening polymerization (PESO), followed by hydrolysis with a base (HPESO). Various molecular weights of PESO and HPESO were prepared by varying the reaction temperature and/or catalyst conc...

  4. "Green" films from renewable resources: properties of epoxidized soybean oil plasticized ethyl cellulose films.

    PubMed

    Yang, Dong; Peng, Xinwen; Zhong, Linxin; Cao, Xuefei; Chen, Wei; Zhang, Xueming; Liu, Shijie; Sun, Runcang

    2014-03-15

    Epoxidized soybean oil (ESO), which is a biomass-derived resource, was first used as a novel plasticizer for ethyl cellulose (EC) film preparation. Surface morphologies, mechanical performances, thermal properties, oxygen and water vapor permeabilities of plasticized EC films were detected in detail to evaluate the plasticizing effect of ESO and explore the plastication mechanisms. Results showed that ESO was an effective plasticizer that outstripped conventional plasticizers, i.e. dibutyl phthalate (DBP) and triethyl citrate (TEC) in producing high-quality films. Especially, at plasticizer concentrations of 15-25%, ESO-EC films had preferable mechanical properties and better thermal stability, as well as non-flammability. In addition, the water vapor permeability of ESO-EC films was lower than that of traditional plasticized films. Their oxygen permeability was also remained in a low level. These outstanding performances were related to the relatively high molecular weight, hydrophobicity, chemical structure of ESO, and the intermolecular interactions between ESO and EC chains.

  5. Epoxidized Soybean Oil: Evaluation of Oxidative Stabilization and Metal Quenching/Heat Transfer Performance

    NASA Astrophysics Data System (ADS)

    Simencio Otero, Rosa L.; Canale, Lauralice C. F.; Said Schicchi, Diego; Agaliotis, Eliana; Totten, George E.; Sánchez Sarmiento, Gustavo

    2013-07-01

    Vegetable and animal oils as a class of fluids have been used for hundreds of years, if not longer, as quenchants for hardening steel. However, when petroleum oils became available in the late 1800s and early 1900s, the use of these fluids as quenchants, in addition to their use in other industrial oil applications, quickly diminished. This was primarily, but not exclusively, due to their generally very poor thermal-oxidative instability and the difficulty for formulating fluid analogs with varying viscosity properties. Interest in the use of renewable fluids, such as vegetable oils, has increased dramatically in recent years as alternatives to the use of relatively non-biodegradable and toxic petroleum oils. However, the relatively poor thermal-oxidative stability has continued to be a significant reason for their general non-acceptance in the marketplace. Soybean oil (SO) is one of the most highly produced vegetable oils in Brazil. Currently, there are commercially produced epoxidized versions of SO which are available. The objective of this paper is to discuss the potential use of epoxidized SO and its heat transfer properties as a viable alternative to petroleum oils for hardening steel.

  6. Epoxidized soybean oil/ZnO biocomposites for soft tissue applications: preparation and characterization.

    PubMed

    Díez-Pascual, Ana M; Díez-Vicente, Angel L

    2014-10-01

    Biocompatible and biodegradable nanocomposites comprising epoxidized soybean oil (ESO) as matrix, zinc oxide (ZnO) nanoparticles as reinforcements, and 4-dimethylaminopyridine (DMAP) as a catalyst have been successfully prepared via epoxidization of the double bonds of the vegetable oil, ultrasonication, and curing without the need for interfacial modifiers. Their morphology, water uptake, thermal, mechanical, barrier, tribological, and antibacterial properties have been investigated. FT-IR analysis revealed the existence of strong ESO-ZnO hydrogen-bonding interactions. The nanoparticles acted as mass transport barriers, hindering the diffusion of volatiles generated during the decomposition process and leading to higher thermal stability, and also reduced the water absorption and gas permeability of the bioresin. Significant improvements in the static and dynamic mechanical properties, such as storage and Young's moduli, tensile strength, toughness, hardness, glass transition, and heat distortion temperature, were attained on reinforcement. A small drop in the nanocomposite stiffness and strength was found after exposure to several cycles of steam sterilization or to simulated body fluid (SBF) at physiological temperature. Extraordinary reductions in the coefficient of friction and wear rate were detected under both dry and SBF conditions, confirming the potential of these nanoparticles for improving the tribological performance of ESO. The nanocomposites displayed antimicrobial action against human pathogen bacteria with and without UV illumination, which increased progressively with the ZnO content. These sustainable, ecofriendly, and low-cost biomaterials are very promising for use in biomedical applications, like structural tissue engineering scaffolds. PMID:25222018

  7. Epoxidized soybean oil/ZnO biocomposites for soft tissue applications: preparation and characterization.

    PubMed

    Díez-Pascual, Ana M; Díez-Vicente, Angel L

    2014-10-01

    Biocompatible and biodegradable nanocomposites comprising epoxidized soybean oil (ESO) as matrix, zinc oxide (ZnO) nanoparticles as reinforcements, and 4-dimethylaminopyridine (DMAP) as a catalyst have been successfully prepared via epoxidization of the double bonds of the vegetable oil, ultrasonication, and curing without the need for interfacial modifiers. Their morphology, water uptake, thermal, mechanical, barrier, tribological, and antibacterial properties have been investigated. FT-IR analysis revealed the existence of strong ESO-ZnO hydrogen-bonding interactions. The nanoparticles acted as mass transport barriers, hindering the diffusion of volatiles generated during the decomposition process and leading to higher thermal stability, and also reduced the water absorption and gas permeability of the bioresin. Significant improvements in the static and dynamic mechanical properties, such as storage and Young's moduli, tensile strength, toughness, hardness, glass transition, and heat distortion temperature, were attained on reinforcement. A small drop in the nanocomposite stiffness and strength was found after exposure to several cycles of steam sterilization or to simulated body fluid (SBF) at physiological temperature. Extraordinary reductions in the coefficient of friction and wear rate were detected under both dry and SBF conditions, confirming the potential of these nanoparticles for improving the tribological performance of ESO. The nanocomposites displayed antimicrobial action against human pathogen bacteria with and without UV illumination, which increased progressively with the ZnO content. These sustainable, ecofriendly, and low-cost biomaterials are very promising for use in biomedical applications, like structural tissue engineering scaffolds.

  8. New hybrid latexes from a soybean oil-based waterborne polyurethane and acrylics via emulsion polymerization.

    PubMed

    Lu, Yongshang; Larock, Richard C

    2007-10-01

    A series of new waterborne polyurethane (PU)/acrylic hybrid latexes have been successfully synthesized by the emulsion polymerization of acrylic monomers (butyl acrylate and methyl methacrylate) in the presence of a soybean oil-based waterborne PU dispersion using potassium persulfate as an initiator. The waterborne PU dispersion has been synthesized by a polyaddition reaction of toluene 2,4-diisocyanate and a soybean oil-based polyol (SOL). The resulting hybrid latexes, containing 15-60 wt % SOL as a renewable resource, are very stable and exhibit uniform particle sizes of 125 +/- 20 nm as determined by transmittance electronic microscopy. The structure, thermal, and mechanical properties of the resulting hybrid latex films have been investigated by Fourier transform infrared spectroscopy, solid state 13C NMR spectroscopy, dynamic mechanical analysis, extraction, and mechanical testing. Grafting copolymerization of the acrylic monomers onto the PU network occurs during the emulsion polymerization, leading to a significant increase in the thermal and mechanical properties of the resulting hybrid latexes. This work provides a new way of utilizing renewable resources to prepare environmentally friendly hybrid latexes with high performance for coating applications. PMID:17877401

  9. Preparation and Characterization of Polymeric Surfactants Based on Epoxidized Soybean Oil Grafted Hydroxyethyl Cellulose.

    PubMed

    Huang, Xujuan; Liu, He; Shang, Shibin; Rao, Xiaoping; Song, Jie

    2015-10-21

    Epoxidized soybean oil (ESO) grafted hydroxyethyl cellulose (HEC) was prepared via ring-opening polymerization, in which the hydroxyl groups of HEC acted as initiators and the polymeric ESO were covalently bonded to the HEC. Hydrolysis of ESO-grafted HEC (ESO-HEC) was performed with sodium hydroxide, and the hydrolyzed ESO-HEC (H-ESO-HEC) products were characterized via Fourier transform infrared (FT-IR) and (1)H and (13)C nuclear magnetic resonance (NMR) spectroscopies, high-temperature gel permeation chromatography (HT-GPC), and differential scanning calorimetry (DSC). The results indicated that ring-opening polymerization of ESO occurred with the hydroxyl groups of HEC as initiators. The molecular weights of the H-ESO-HEC products were varied by adjusting the mass ratio of HEC and ESO. Through neutralizing the carboxylic acid of H-ESO-HEC with sodium hydroxide, novel polymeric surfactants (H-ESO-HEC-Na) were obtained, and the effects of polymeric surfactants on the surface tension of water were investigated as a function of concentration of H-ESO-HEC-Na. The H-ESO-HEC-Na was effective at lowering the surface tension of water to 26.33 mN/m, and the critical micelle concentration (CMC) value decreased from 1.053 to 0.157 g/L with increases in molecular weights of the polymeric surfactants. Rheological measurements indicated that the H-ESO-HEC-Na solutions changed from pseudoplastic property to Newtonian with increasing shear rate. PMID:26416659

  10. Preparation and Characterization of Polymeric Surfactants Based on Epoxidized Soybean Oil Grafted Hydroxyethyl Cellulose.

    PubMed

    Huang, Xujuan; Liu, He; Shang, Shibin; Rao, Xiaoping; Song, Jie

    2015-10-21

    Epoxidized soybean oil (ESO) grafted hydroxyethyl cellulose (HEC) was prepared via ring-opening polymerization, in which the hydroxyl groups of HEC acted as initiators and the polymeric ESO were covalently bonded to the HEC. Hydrolysis of ESO-grafted HEC (ESO-HEC) was performed with sodium hydroxide, and the hydrolyzed ESO-HEC (H-ESO-HEC) products were characterized via Fourier transform infrared (FT-IR) and (1)H and (13)C nuclear magnetic resonance (NMR) spectroscopies, high-temperature gel permeation chromatography (HT-GPC), and differential scanning calorimetry (DSC). The results indicated that ring-opening polymerization of ESO occurred with the hydroxyl groups of HEC as initiators. The molecular weights of the H-ESO-HEC products were varied by adjusting the mass ratio of HEC and ESO. Through neutralizing the carboxylic acid of H-ESO-HEC with sodium hydroxide, novel polymeric surfactants (H-ESO-HEC-Na) were obtained, and the effects of polymeric surfactants on the surface tension of water were investigated as a function of concentration of H-ESO-HEC-Na. The H-ESO-HEC-Na was effective at lowering the surface tension of water to 26.33 mN/m, and the critical micelle concentration (CMC) value decreased from 1.053 to 0.157 g/L with increases in molecular weights of the polymeric surfactants. Rheological measurements indicated that the H-ESO-HEC-Na solutions changed from pseudoplastic property to Newtonian with increasing shear rate.

  11. Biobased composites from cross-linked soybean oil and thermoplastic polyurethane

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean oil is an important sustainable material. Crosslinked acrylated epoxidized soybean oil (AESO) is brittle and the incorporation of thermoplastic polyurethane improves its toughness. The hydrophilic functional groups from both oil and polyurethane contribute to the adhesion of the blend compon...

  12. Computer-Aided Design and Computer-Aided Manufacturing Hydroxyapatite/Epoxide Acrylate Maleic Compound Construction for Craniomaxillofacial Bone Defects.

    PubMed

    Zhang, Lei; Shen, Shunyao; Yu, Hongbo; Shen, Steve Guofang; Wang, Xudong

    2015-07-01

    The aim of this study was to investigate the use of computer-aided design and computer-aided manufacturing hydroxyapatite (HA)/epoxide acrylate maleic (EAM) compound construction artificial implants for craniomaxillofacial bone defects. Computed tomography, computer-aided design/computer-aided manufacturing and three-dimensional reconstruction, as well as rapid prototyping were performed in 12 patients between 2008 and 2013. The customized HA/EAM compound artificial implants were manufactured through selective laser sintering using a rapid prototyping machine into the exact geometric shapes of the defect. The HA/EAM compound artificial implants were then implanted during surgical reconstruction. Color-coded superimpositions demonstrated the discrepancy between the virtual plan and achieved results using Geomagic Studio. As a result, the HA/EAM compound artificial bone implants were perfectly matched with the facial areas that needed reconstruction. The postoperative aesthetic and functional results were satisfactory. The color-coded superimpositions demonstrated good consistency between the virtual plan and achieved results. The three-dimensional maximum deviation is 2.12 ± 0.65  mm and the three-dimensional mean deviation is 0.27 ± 0.07  mm. No facial nerve weakness or pain was observed at the follow-up examinations. Only 1 implant had to be removed 2 months after the surgery owing to severe local infection. No other complication was noted during the follow-up period. In conclusion, computer-aided, individually fabricated HA/EAM compound construction artificial implant was a good craniomaxillofacial surgical technique that yielded improved aesthetic results and functional recovery after reconstruction.

  13. Ring-opening polymerization of epoxidized soybean oil catalyzed by the superacid, Fluroantimonic acid hexahydrate (HSbF6-6H2O)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ring-opening polymerization of epoxidized soybean oil (ESO) catalyzed by the super acid, fluroantimonic acid hexahydrate (HSbF6-6H2O), in ethyl acetate was conducted. The resulting polymers, SA-RPESO, were characterized using infrared spectroscopy, differential scanning calorimetry, thermogravimetri...

  14. Fluoroantimonic acid hexahydrate (HSbF6-6H2O) catalysis: The ring-opening polymerization of epoxidized soybean oil

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ring-opening polymerization of epoxidized soybean oil (ESO) catalyzed by a super acid, fluroantimonic acid hexahydrate (HSbF6-6H2O), in ethyl acetate was conducted in an effort to develop useful biodegradable polymers. The resulting polymerized ESO (SA-RPESO) were characterized by using infrared (IR...

  15. Wheat gluten-based renewable and biodegradable polymer materials with enhanced hydrophobicity by using epoxidized soybean oil as a modifier.

    PubMed

    Zhang, Xiaoqing; Do, My Dieu; Kurniawan, Lusiana; Qiao, Greg G

    2010-10-13

    Epoxidized soybean oil (ESO) was applied as an additive for wheat gluten (WG) to modify the properties of the renewable and biodegradable natural polymer materials. Optimum intermolecular interactions and crosslinking between ESO chains and the WG matrix were achieved under alkaline conditions. The WGESO materials were heterogeneous on a scale of 20-30 nm, but the homogeneity was improved upon increasing the amount of glycerol as a plasticizer in the materials. The combination of plasticization and crosslinking effects derived from ESO resulted in good retention in mechanical strength for the plasticized WGESO materials as compared to those without 10 wt% of mobile ESO additives. The hydrophobicity of the plasticized WG materials was also enhanced significantly by using the ESO additives.

  16. Application of Fourier transform infrared (FT-IR) spectroscopy to the study of the modification of epoxidized sunflower oil by acrylation.

    PubMed

    Irinislimane, Ratiba; Belhaneche-Bensemra, Naima

    2012-12-01

    Commercial sunflower oil was epoxidized at the laboratory-scale. The epoxidized sunflower oil (ESFO) was modified following the acrylation reaction. Modification was carried out simultaneously using acrylic acid (AA) and triethylamine (TEA). To optimize the reaction conditions, the effects of four temperatures (40, 60, 80, and 100 °C), the ESFO:AA (100:100) ratio, and 0.2% TEA were investigated. The rate of conversion was analyzed with both FT-IR and titration of the oxirane ring. After that, the temperature with the highest conversion was selected and used throughout for all modification reactions. Then, four ratios (100:100, 100:90, 100:80, and 100:75) of ESFO:AA were analyzed at four different concentrations of TEA (0.2, 0.3, 0.4, and 0.5%) to determine the best estimate for both the ESFO:AA ratio and the catalyst concentration. Conversion rate was analyzed using FT-IR spectroscopy by measuring the concentrations of ester, carbonyl, and alcohol groups. Moreover, oxirane-ring concentration was estimated using the titration method (with gentian violet as indicator) and FT-IR spectroscopy (epoxy ring absorptions at 1270 cm(-1) and 877 cm(-1)). Based on conversion yield, the optimum ESFO:AA ratio corresponds to 100:80; the best temperature reaction was at 60 °C, and the best TEA concentration was 0.2%. The critical amounts of reactants needed to reach maximum conversion were established. The final acid value of the acrylated ESFO after washing (pH = 7) was 2.1 mg potassium hydroxide (KOH)·g(-1). All results show that FT-IR spectroscopy is a simple, low-cost, rapid method for investigating the kinetics of a reaction. PMID:23231904

  17. Transfer of the epoxidation of soybean oil from batch to flow chemistry guided by cost and environmental issues.

    PubMed

    Kralisch, Dana; Streckmann, Ina; Ott, Denise; Krtschil, Ulich; Santacesaria, Elio; Di Serio, Martino; Russo, Vincenzo; De Carlo, Lucrezia; Linhart, Walter; Christian, Engelbert; Cortese, Bruno; de Croon, Mart H J M; Hessel, Volker

    2012-02-13

    The simple transfer of established chemical production processes from batch to flow chemistry does not automatically result in more sustainable ones. Detailed process understanding and the motivation to scrutinize known process conditions are necessary factors for success. Although the focus is usually "only" on intensifying transport phenomena to operate under intrinsic kinetics, there is also a large intensification potential in chemistry under harsh conditions and in the specific design of flow processes. Such an understanding and proposed processes are required at an early stage of process design because decisions on the best-suited tools and parameters required to convert green engineering concepts into practice-typically with little chance of substantial changes later-are made during this period. Herein, we present a holistic and interdisciplinary process design approach that combines the concept of novel process windows with process modeling, simulation, and simplified cost and lifecycle assessment for the deliberate development of a cost-competitive and environmentally sustainable alternative to an existing production process for epoxidized soybean oil. PMID:22287262

  18. Migration of epoxidized soybean oil (ESBO) and phthalates from twist closures into food and enforcement of the overall migration limit.

    PubMed

    Pedersen, G A; Jensen, L K; Fankhauser, A; Biedermann, S; Petersen, J H; Fabech, B

    2008-04-01

    Nineteen samples of food in glass jars with twist closures were collected by the national food inspectors at Danish food producers and a few importers, focusing on fatty food, such as vegetables in oil, herring in dressing or pickle, soft spreadable cheese, cream, dressings, peanut butter, sauces and infant food. The composition of the plasticizers in the gaskets was analysed by gas chromatography with flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Epoxidized soybean oil (ESBO) and phthalates were determined in the homogenized food samples. ESBO was the principal plasticizer in five of the gaskets; in 14 it was phthalates. ESBO was found in seven of the food samples at concentrations from 6 to 100 mg kg(-1). The highest levels (91-100 mg kg(-1)) were in oily foods such as garlic, chilli or olives in oil. Phthalates, i.e. di-iso-decylphthalate (DIDP) and di-iso-nonylphthalates (DINP), were found in seven samples at 6-173 mg kg(-1). The highest concentrations (99-173 mg kg(-1)) were in products of garlic and tomatoes in oil and in fatty food products such as sauce béarnaise and peanut butter. For five of the samples the overall migration from unused lids to the official fatty food simulant olive oil was determined and compared with the legal limit of 60 mg kg(-1). The results ranged from 76 to 519 mg kg(-1) and as a consequence the products were withdrawn from the market. PMID:18348048

  19. Migration of epoxidized soybean oil (ESBO) and phthalates from twist closures into food and enforcement of the overall migration limit.

    PubMed

    Pedersen, G A; Jensen, L K; Fankhauser, A; Biedermann, S; Petersen, J H; Fabech, B

    2008-04-01

    Nineteen samples of food in glass jars with twist closures were collected by the national food inspectors at Danish food producers and a few importers, focusing on fatty food, such as vegetables in oil, herring in dressing or pickle, soft spreadable cheese, cream, dressings, peanut butter, sauces and infant food. The composition of the plasticizers in the gaskets was analysed by gas chromatography with flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Epoxidized soybean oil (ESBO) and phthalates were determined in the homogenized food samples. ESBO was the principal plasticizer in five of the gaskets; in 14 it was phthalates. ESBO was found in seven of the food samples at concentrations from 6 to 100 mg kg(-1). The highest levels (91-100 mg kg(-1)) were in oily foods such as garlic, chilli or olives in oil. Phthalates, i.e. di-iso-decylphthalate (DIDP) and di-iso-nonylphthalates (DINP), were found in seven samples at 6-173 mg kg(-1). The highest concentrations (99-173 mg kg(-1)) were in products of garlic and tomatoes in oil and in fatty food products such as sauce béarnaise and peanut butter. For five of the samples the overall migration from unused lids to the official fatty food simulant olive oil was determined and compared with the legal limit of 60 mg kg(-1). The results ranged from 76 to 519 mg kg(-1) and as a consequence the products were withdrawn from the market.

  20. The effect of epoxidized soybean oil on mechanical and rheological properties of poly(butylene succinate)/lignin via vane extruder

    NASA Astrophysics Data System (ADS)

    Liu, Huanyu; Huang, Zhaoxia; Qu, Jinping; Meng, Cong

    2016-03-01

    Epoxidized Soybean Oil (ESO) have been used as the compatilizer in the Poly (butylene succinate)/lignin (PBS/lignin) composites. Compatibilized composites were fabricated by a novel vane extruder (VE) which can generate global and dynamic elongational flow. The effects of ESO on the mechanical, rheological properties and morphology of PBS/lignin were studied. The results indicated that the use of ESO had plasticizing effect on the matrix PBS while the addition reduced tensile strength. From SEM micrographs it could be clearly observed that there was a better interfacial adhesion between lignin and matrix. Meanwhile, rheological tests showed the incorporation of ESO improved its Newtonian behavior and can enhance PBS's flexibility.

  1. Migration analysis of epoxidized soybean oil and other plasticizers in commercial lids for food packaging by gas chromatography-mass spectrometry.

    PubMed

    Bueno-Ferrer, C; Jimenez, A; Garrigos, M C

    2010-10-01

    A modification of the method of Castle et al. (J. Chromatogr. 1988: 437:274-280) for the analysis of epoxidized soybean oil (ESBO) is proposed to simplify the analysis and reduce the time and consumption of reagents. The proposed modifications, particularly the elimination of the internal standard, resulted in a simpler, faster and more economical method. A complete analytical validation, including evaluation of the main analytical parameters, such as detection and quantification limits, linearity, working range, precision, accuracy and selectivity, was carried out. The data demonstrated the suitability of the proposed method for the determination of ESBO in polymer matrices. A specific migration study for ESBO in different food simulants (fat and aqueous) was carried out by applying the method to poly(vinyl chloride) materials prepared with known amounts of ESBO, as well as some commercial lids. High levels of migration of ESBO into fat simulants were found. In the case of commercial lids, in addition to ESBO, some other plasticizers such as citrates, adipates and sebacates were found and quantified to establish their migration under different conditions of use.

  2. Heptachlor epoxide

    Integrated Risk Information System (IRIS)

    Heptachlor epoxide ; CASRN 1024 - 57 - 3 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogen

  3. Polymerization of epoxidized triglycerides with fluorosulfonic acid

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The use of triglycerides as agri-based renewable raw materials for the development of new products is highly desirable in view of uncertain future petroleum prices. A new method of polymerizing epoxidized soybean oil has been devised with the use of fluorosulfonic acid. Depending on the reaction con...

  4. Industrially relevant epoxy-acrylate hybrid resin photopolymerizations

    NASA Astrophysics Data System (ADS)

    Ajiboye, Gbenga I.

    Photopolymerization of epoxy-acrylate hybrid resins takes advantages of inherent properties present in the free-radical and cationic reactions to reduce oxygen inhibition problems that plague free-radical reactions. Similarly, the combined reaction mechanisms reduce moisture sensitivity of the cationic reactions. Despite the advantages of epoxy-acrylate hybrid resins, problems persist that need to be addressed. For example, low conversion and polymerization rate of the epoxides are a problem, because the fast acrylate conversion prevents the epoxide from reaching high conversion. Controlling phase separation is challenging, since two moieties with different properties are reacting. The physical properties of the polymer will be impacted by the availability of different moieties. High shrinkage stress results from the acrylate moiety, causing buckling and cracking in film and coating applications. The overall goal of this study is to use the fundamental knowledge of epoxy-acrylate hybrid resins to formulate industrially viable polymers. In order to achieve this goal, the study focuses on the following objectives: (I) determine the apparent activation energy of the hybrid monomer METHB, (II) increase epoxide conversion and polymerization rate of hybrid formulations, and (III) control physical properties in epoxy-acrylate hybrid resins. In order to increase the epoxide conversion and rate of polymerization, the sensitivity of epoxides to alcohol is used to facilitate the activated monomer (AM) mechanism and induce a covalent bond between the epoxide and acrylate polymers through the hydroxyl group. It is hypothesized that if the AM mechanism is facilitated, epoxide conversion will increase. As a result, the resins can be tailored to control phase separation and physical properties, and shrinkage stress can be reduced. In pursuit of these objectives, the hybrid monomer METHB was polymerized at temperatures ranging from 30°C to 70°C to obtain apparent activation

  5. Electrochemical epoxidation of olefins

    SciTech Connect

    van der Eijk, J.M. )

    1987-08-01

    Direct epoxidation of an olefin, using oxygen and a catalyst, only proceeds with a high yield in the case of ethene. All commercial processes for the epoxidation of higher olefins therefore make use of an indirect route, yielding a co-product besides the desired epoxide. From an economic point of view this is an unfavorable situation since it couples the manufacture of two products. Recently, we have made a comprehensive study of a non-conventional method involving the electrochemical oxidation of olefins to epoxides. The major technical challenge posed by the electrochemical route to epoxides is the identification of conditions under which the desired reaction proceeds selectively. An exploratory study had indicated that the direct oxidation of olefins at the surface of catalytically active anodes (Pt, silver oxide, nickel oxide, lead ruthenates (1)) proceeds either slowly or non-selectively. A more promising approach was expected to be electrochemical (re)generation of an epoxidation agent at the anode of an electrochemical cell and carrying out the epoxidation in the anolyte solution. Epoxidation agents of interest included thallium (III) acetate complexes, hypobromite and silver(II)-pyridine complexes. Here we report on the electrochemical oxidation of olefins as mediated by silver-pyridine complexes. Subjects to be dealt with include the chemical efficacy of the process as well as the kinettics and mechanism of the olefin-Ag(II) reaction.

  6. Epoxidation catalyst and process

    DOEpatents

    Linic, Suljo; Christopher, Phillip

    2010-10-26

    Disclosed herein is a catalytic method of converting alkenes to epoxides. This method generally includes reacting alkenes with oxygen in the presence of a specific silver catalyst under conditions suitable to produce a yield of the epoxides. The specific silver catalyst is a silver nanocrystal having a plurality of surface planes, a substantial portion of which is defined by Miller indices of (100). The reaction is performed by charging a suitable reactor with this silver catalyst and then feeding the reactants to the reactor under conditions to carry out the reaction. The reaction may be performed in batch, or as a continuous process that employs a recycle of any unreacted alkenes. The specific silver catalyst has unexpectedly high selectivity for epoxide products. Consequently, this general method (and its various embodiments) will result in extraordinarily high epoxide yields heretofore unattainable.

  7. Succinic anhydrides from epoxides

    SciTech Connect

    Coates, Geoffrey W.; Rowley, John M.

    2013-07-09

    Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.

  8. Succinic anhydrides from epoxides

    SciTech Connect

    Coates, Geoffrey W; Rowley, John M

    2014-12-30

    Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.

  9. Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

    PubMed Central

    Abderrezak, Meriem K; Šichová, Kristýna; Dominguez-Boblett, Nancy; Dupé, Antoine; Kabouche, Zahia; Bruneau, Christian

    2015-01-01

    Summary The cross metathesis of 1,2-epoxy-5-hexene (1) with methyl acrylate and acrylonitrile was investigated as an entry to the synthesis of polyfunctional compounds. The resulting cross metathesis products were hydrogenated in a tandem fashion employing the residual ruthenium from the metathesis step as the hydrogenation catalyst. Interestingly, the epoxide ring remained unreactive toward this hydrogenation method. The saturated compound resulting from the cross metathesis of 1 with methyl acrylate was transformed by means of nucleophilic ring-opening of the epoxide to furnish a diol, an alkoxy alcohol and an amino alcohol in high yields. PMID:26664605

  10. New ¹H NMR-Based Technique To Determine Epoxide Concentrations in Oxidized Oil.

    PubMed

    Xia, Wei; Budge, Suzanne M; Lumsden, Michael D

    2015-06-24

    A new method to determine epoxide concentrations in oxidized oils was developed and validated using (1)H NMR. Epoxides derived from lipid oxidation gave signals between 2.90 and 3.24 ppm, well separated from the signals of other lipid oxidation products. To calibrate, soybean oils with a range of epoxide concentrations were synthesized and analyzed using (1)H NMR by taking the sn-1,3 glycerol protons (4.18, 4.33 ppm) as internal references. The (1)H NMR signals were compared to the epoxide content determined by titration with hydrogen bromide (HBr)-acetic acid solution. As expected, the signal response increased with concentration linearly (R(2) = 99.96%), and validation of the method gave results comparable to those of the HBr method. A study of the oxidative stability of soybean oil was performed by applying this method to monitor epoxides during thermal lipid oxidation. The epoxide content increased over time and showed a different trend compared to peroxide value (PV). A phenomenological model was suggested to model epoxides derived from lipid oxidation. PMID:26035119

  11. Acrylic acid

    Integrated Risk Information System (IRIS)

    Acrylic acid ( CASRN 79 - 10 - 7 ) Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic Eff

  12. Methyl acrylate

    Integrated Risk Information System (IRIS)

    Methyl acrylate ; CASRN 96 - 33 - 3 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic Ef

  13. Microbial production of epoxides

    SciTech Connect

    Clark, Thomas R.; Roberto, Francisco F.

    2003-06-10

    A method for microbial production of epoxides and other oxygenated products is disclosed. The method uses a biocatalyst of methanotrophic bacteria cultured in a biphasic medium containing a major amount of a non-aqueous polar solvent. Regeneration of reducing equivalents is carried out by using endogenous hydrogenase activity together with supplied hydrogen gas. This method is especially effective with gaseous substrates and cofactors that result in liquid products.

  14. "Green" composites and nanocomposites from soybean oil

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In this study, we report preparation of epoxidized soybean oil (ESO) based "green" composites and nanocomposites. The high strength and stiffness composites and nanocomposites are formed through flax fiber and organoclay reinforcement. The epoxy resin, 1,1,1-tris(p-hydroxyphenyl)ethane triglycidyl...

  15. Preparation of Soypolymers by Ring-opening Polymerization of Epoxdized Soybean Oil

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ring opening polymerization of epoxidized soybean oil (ESO) initiated by boron trifluoride diethyl etherate in methylene chloride was conducted in an effort to develop useful biodegradable polymers. The resulting polymers (PESO) were characterized using Infrared (IR), differential scanning calorime...

  16. Synthesis of Radiation Curable Palm Oil-Based Epoxy Acrylate: NMR and FTIR Spectroscopic Investigations.

    PubMed

    Salih, Ashraf M; Ahmad, Mansor Bin; Ibrahim, Nor Azowa; Dahlan, Khairul Zaman Hj Mohd; Tajau, Rida; Mahmood, Mohd Hilmi; Yunus, Wan Md Zin Wan

    2015-01-01

    Over the past few decades, there has been an increasing demand for bio-based polymers and resins in industrial applications, due to their potential lower cost and environmental impact compared with petroleum-based counterparts. The present research concerns the synthesis of epoxidized palm oil acrylate (EPOLA) from an epoxidized palm oil product (EPOP) as environmentally friendly material. EPOP was acrylated by acrylic acid via a ring opening reaction. The kinetics of the acrylation reaction were monitored throughout the reaction course and the acid value of the reaction mixture reached 10 mg KOH/g after 16 h, indicating the consumption of the acrylic acid. The obtained epoxy acrylate was investigated intensively by means of FTIR and NMR spectroscopy, and the results revealed that the ring opening reaction was completed successfully with an acrylation yield about 82%. The UV free radical polymerization of EPOLA was carried out using two types of photoinitiators. The radiation curing behavior was determined by following the conversion of the acrylate groups. The cross-linking density and the hardness of the cured EPOLA films were measured to evaluate the effect of the photoinitiator on the solid film characteristics, besides, the thermal and mechanical properties were also evaluated. PMID:26248072

  17. Molecular Interactions between a Novel Soybean Oil-Based Polymer and Doxorubicin

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A novel soybean oil-based polymer, hydrolyzed polymers of epoxidized soybean oil (HPESO), was developed and investigated for drug delivery. This work was aimed at determining the molecular interactions between HPESO and doxorubicin (DOX), an anticancer drug. Powder X-ray diffraction, ATR-FTIR and ...

  18. Study of soybean oil-based polymers for controlled release anticancer drugs

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean oil-based polymers were prepared by the ring-opening polymerization of epoxidized soybean oil with Lewis acid catalyst. The formed polymers (HPESO) could be converted into hydrogels through hydrolysis. Characterization and viscoelastic properties of this soy hydrogel and application in contr...

  19. Anti-wear additive derived from soybean oil and boron utilized in a gear oil formulation

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The synthesis of lubricant additives based on boron and epoxidized soybean oil are presented. These additives are made from a simple patent pending method involving a ring opening reaction and addition of the borate. A pair of different additives were tested in soybean oil, polyalpha olefin basestoc...

  20. Characterization of novel soybean-oil-based thermosensitive amphiphilic polymers for drug delivery applications

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Characterization, aggregation behavior, physical properties and drug-polymer interaction of novel soybean oil-based polymers i.e., hydrolyzed polymers of (epoxidized) soybean oil (HPESO), were studied. The surface tension method was used to determine the critical micelle concentration (CMC). CMC w...

  1. Organocatalytic asymmetric hydrolysis of epoxides.

    PubMed

    Monaco, Mattia Riccardo; Prévost, Sébastien; List, Benjamin

    2014-07-28

    The hydrolytic ring opening of epoxides is an important biosynthetic transformation and is also applied industrially. We report the first organocatalytic variant of this reaction, exploiting our recently discovered activation of carboxylic acids with chiral phosphoric acids via heterodimerization. The methodology mimics the enzymatic mechanism, which involves an enzyme-bound carboxylate nucleophile. A newly designed phosphoric acid catalyst displays high stereocontrol in the desymmetrization of meso-epoxides. The methodology shows wide generality with cyclic, acylic, aromatic, and aliphatic substrates. We also apply our method in the first highly enantioselective anti-dihydroxylation of simple olefins.

  2. Acrylate Systemic Contact Dermatitis.

    PubMed

    Sauder, Maxwell B; Pratt, Melanie D

    2015-01-01

    Acrylates, the 2012 American Contact Dermatitis Society allergen of the year, are found in a range of products including the absorbent materials within feminine hygiene pads. When fully polymerized, acrylates are nonimmunogenic; however, if not completely cured, the monomers can be potent allergens.A 28-year-old woman is presented, who had her teeth varnished with Isodan (Septodont, Saint-Maur-des-Fossés, France) containing HEMA (2-hydroxyethyl methacrylate) with no initial reaction. Approximately 1 month later, the patient developed a genital dermatitis secondary to her feminine hygiene pads. The initial reaction resolved, but 5 months later, the patient developed a systemic contact dermatitis after receiving a second varnishing.The patient was dramatically patch test positive to many acrylates. This case demonstrates a reaction to likely unpolymerized acrylates within a feminine hygiene pad, as well as broad cross-reactivity or cosensitivity to acrylates, and possibly a systemic contact dermatitis with systemic re-exposure to unpolymerized acrylates.

  3. 21 CFR 172.723 - Epoxidized soybean oil.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... is incorporated by reference in accordance with 5 U.S.C 552(a) and 1 CFR part 51. Copies are... U.S.C. 552(a) and 1 CFR part 51. The availability of this incorporation by reference is given in... incorporated by reference in accordance with 5 U.S.C. 552(a) and 1 CFR part 51. Copies are available from...

  4. 21 CFR 172.723 - Epoxidized soybean oil.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... is incorporated by reference in accordance with 5 U.S.C 552(a) and 1 CFR part 51. Copies are... U.S.C. 552(a) and 1 CFR part 51. The availability of this incorporation by reference is given in... incorporated by reference in accordance with 5 U.S.C. 552(a) and 1 CFR part 51. Copies are available from...

  5. 21 CFR 172.723 - Epoxidized soybean oil.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 5 U.S.C 552(a) and 1 CFR part 51. Copies are available from the American Oil Chemists' Society, P. O... incorporated by reference in accordance with 5 U.S.C. 552(a) and 1 CFR part 51. The availability of this... in the control), which is incorporated by reference in accordance with 5 U.S.C. 552(a) and 1 CFR...

  6. 21 CFR 172.723 - Epoxidized soybean oil.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... is incorporated by reference in accordance with 5 U.S.C 552(a) and 1 CFR part 51. Copies are... U.S.C. 552(a) and 1 CFR part 51. The availability of this incorporation by reference is given in... incorporated by reference in accordance with 5 U.S.C. 552(a) and 1 CFR part 51. Copies are available from...

  7. 21 CFR 172.723 - Epoxidized soybean oil.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... is incorporated by reference in accordance with 5 U.S.C 552(a) and 1 CFR part 51. Copies are... accordance with 5 U.S.C. 552(a) and 1 CFR part 51. The availability of this incorporation by reference is... is incorporated by reference in accordance with 5 U.S.C. 552(a) and 1 CFR part 51. Copies...

  8. Organocatalyzed enantioselective desymmetrization of aziridines and epoxides

    PubMed Central

    2013-01-01

    Summary Enantioselective desymmetrization of meso-aziridines and meso-epoxides with various nucleophiles by organocatalysis has emerged as a cutting-edge approach in recent years. This review summarizes the origin and recent developments of enantioselective desymmetrization of meso-aziridines and meso-epoxides in the presence of organocatalysts. PMID:24062828

  9. Reduction of epoxidized vegetable oils: a novel method to prepare bio-based polyols for polyurethanes.

    PubMed

    Zhang, Chaoqun; Ding, Rui; Kessler, Michael R

    2014-06-01

    A novel method, epoxidation/reduction of vegetable oils, is developed to prepare bio-based polyols for the manufacture of polyurethanes (PUs). These polyols are synthesized from castor oil (CO), epoxidized soybean oil, and epoxidized linseed oil and their molecular structures are characterized. They are used to prepare a variety of PUs, and their thermomechanical properties are compared to those of PU made with petroleum-based polyol (P-450). It is shown that PUs made with polyols from soybean and linseed oil exhibit higher glass transition temperatures, tensile strength, and Young's modulus and PU made with polyol from CO exhibits higher elongation at break and toughness than PU made with P-450. However, PU made with P-450 displays better thermal resistance because of tri-ester structure and terminal functional groups. The method provides a versatile way to prepare bio-polyols from vegetable oils, and it is expected to partially or completely replace petroleum-based polyols in PUs manufacture.

  10. Reactive coating of soybean oil-based polymer on nanofibrillated cellulose film for water vapor barrier packaging.

    PubMed

    Lu, Peng; Xiao, Huining; Zhang, Weiwei; Gong, Glen

    2014-10-13

    Nanofibrillated cellulose (NFC) easily forms a high strength film but is unable to withstand the influence of water vapor when used in high moisture situations. The water vapor transmission rate (WVTR) of a NFC film was as high as 5088 g/m(2)24h (38 °C, 90% RH). The addition of beeswax latex in a NFC casting film (NFX) lowered the WVTR to 3918 g/m(2)24h. To further reduce the WVTR, a coating agent comprised of acrylated epoxidized soybean oil (AESO) and 3-aminopropyltriethoxysilane (APTS) was applied onto the NFX film using a rod coater. A combination of the suitable AESO/APTS ratio, initiator dosing, curing time and temperature could reduce the WVTR to 188 g/m(2) 24h when the coat weight was 5 g/m(2). Moreover, the coated NFX film was highly hydrophobic along with the improved transparency and thermal stability. This biodegradable polymer-coated NFC film can be used as potential packaging barrier in certain areas.

  11. Acrylic vessel cleaning tests

    SciTech Connect

    Earle, D.; Hahn, R.L.; Boger, J.; Bonvin, E.

    1997-02-26

    The acrylic vessel as constructed is dirty. The dirt includes blue tape, Al tape, grease pencil, gemak, the glue or residue form these tapes, finger prints and dust of an unknown composition but probably mostly acrylic dust. This dirt has to be removed and once removed, the vessel has to be kept clean or at least to be easily cleanable at some future stage when access becomes much more difficult. The authors report on the results of a series of tests designed: (a) to prepare typical dirty samples of acrylic; (b) to remove dirt stuck to the acrylic surface; and (c) to measure the optical quality and Th concentration after cleaning. Specifications of the vessel call for very low levels of Th which could come from tape residues, the grease pencil, or other sources of dirt. This report does not address the concerns of how to keep the vessel clean after an initial cleaning and during the removal of the scaffolding. Alconox is recommended as the cleaner of choice. This acrylic vessel will be used in the Sudbury Neutrino Observatory.

  12. Epoxides and Soluble Epoxide Hydrolase in Cardiovascular Physiology

    PubMed Central

    Imig, John D.

    2013-01-01

    Epoxyeicosatrienoic acids (EETs) are arachidonic acid metabolites that importantly contribute to vascular and cardiac physiology. The contribution of EETs to vascular and cardiac function is further influenced by soluble epoxide hydrolase (sEH) that degrades EETs to diols. Vascular actions of EETs include dilation and angiogenesis. EETs also decrease inflammation and platelet aggregation and in general act to maintain vascular homeostasis. Myocyte contraction and increased coronary blood flow are the two primary EET actions in the heart. EET cell signaling mechanisms are tissue and organ specific and provide significant evidence for the existence of EET receptors. Additionally, pharmacological and genetic manipulations of EETs and sEH have demonstrated a contribution for this metabolic pathway to cardiovascular diseases. Given the impact of EETs to cardiovascular physiology, there is emerging evidence that development of EET-based therapeutics will be beneficial for cardiovascular diseases. PMID:22298653

  13. Epoxides and soluble epoxide hydrolase in cardiovascular physiology.

    PubMed

    Imig, John D

    2012-01-01

    Epoxyeicosatrienoic acids (EETs) are arachidonic acid metabolites that importantly contribute to vascular and cardiac physiology. The contribution of EETs to vascular and cardiac function is further influenced by soluble epoxide hydrolase (sEH) that degrades EETs to diols. Vascular actions of EETs include dilation and angiogenesis. EETs also decrease inflammation and platelet aggregation and in general act to maintain vascular homeostasis. Myocyte contraction and increased coronary blood flow are the two primary EET actions in the heart. EET cell signaling mechanisms are tissue and organ specific and provide significant evidence for the existence of EET receptors. Additionally, pharmacological and genetic manipulations of EETs and sEH have demonstrated a contribution for this metabolic pathway to cardiovascular diseases. Given the impact of EETs to cardiovascular physiology, there is emerging evidence that development of EET-based therapeutics will be beneficial for cardiovascular diseases.

  14. Acrylic purification and coatings

    NASA Astrophysics Data System (ADS)

    Kuźniak, Marcin

    2011-04-01

    Radon (Rn) and its decay daughters are a well-known source of background in direct WIMP detection experiments, as either a Rn decay daughter or an alpha particle emitted from a thin inner surface layer of a detector could produce a WIMP-like signal. Different surface treatment and cleaning techniques have been employed in the past to remove this type of contamination. A new method of dealing with the problem has been proposed and used for a prototype acrylic DEAP-1 detector. Inner surfaces of the detector were coated with a layer of ultra pure acrylic, meant to shield the active volume from alphas and recoiling nuclei. An acrylic purification technique and two coating techniques are described: a solvent-borne (tested on DEAP-1) and solvent-less (being developed for the full scale DEAP-3600 detector).

  15. Acrylic purification and coatings

    SciTech Connect

    Kuzniak, Marcin

    2011-04-27

    Radon (Rn) and its decay daughters are a well-known source of background in direct WIMP detection experiments, as either a Rn decay daughter or an alpha particle emitted from a thin inner surface layer of a detector could produce a WIMP-like signal. Different surface treatment and cleaning techniques have been employed in the past to remove this type of contamination. A new method of dealing with the problem has been proposed and used for a prototype acrylic DEAP-1 detector. Inner surfaces of the detector were coated with a layer of ultra pure acrylic, meant to shield the active volume from alphas and recoiling nuclei. An acrylic purification technique and two coating techniques are described: a solvent-borne (tested on DEAP-1) and solvent-less (being developed for the full scale DEAP-3600 detector).

  16. Acrylic mechanical bond tests

    SciTech Connect

    Wouters, J.M.; Doe, P.J.

    1991-02-01

    The tensile strength of bonded acrylic is tested as a function of bond joint thickness. 0.125 in. thick bond joints were found to posses the maximum strength while the acceptable range of joints varied from 0.063 in. to almost 0.25 in. Such joints are used in the Sudbury Neutrino Observatory.

  17. Advances in acrylic-alkyd hybrid synthesis and characterization

    NASA Astrophysics Data System (ADS)

    Dziczkowski, Jamie

    2008-10-01

    performance. Reversible-addition fragmentation polymerization techniques were employed to create a new class of acrylic-alkyd hybrid materials. Medium and long oil alkyds made from the monoglyceride process using soybean oil, glycerol, and phthalic anhydride were modified with a RAFT chain transfer agent. The alkyd macro-RAFT agents were reached by end-capping a medium oil soya-based alkyd with a carboxy-functional trithiocarbonate. The alkyd macro-RAFT agents were then used to create acrylic-alkyd block structures by polymerizing different acrylic monomers, including both acrylates and methacrylates in the presence of the macro-RAFT agent and 2, 2'-azobisisobutyronitrile (AIBN). Co-acrylic segments were reached by complete polymerization of one monomer followed by the addition of a second monomer and additional free radical initiator. The alkyds, macro-RAFT agents and, acrylic-alkyd blocks were characterized by size-exclusion chromatography (SEC), FTIR, and 1H-NMR. Pseudo-first-order kinetics behavior and conversion vs. molecular weight plots show that the RAFT-mediated reaction afforded a more controlled process for the synthesis of acrylated-alkyd materials. Preliminary coatings tests showed that material properties of acrylated-alkyds achieved by RAFT polymerization exhibit good overall coatings properties including adhesion, gloss, hardness, and impact resistance.

  18. Novel bio-based thermoset resins based on epoxidized vegetable oils for structural adhesives

    NASA Astrophysics Data System (ADS)

    Sivasubramanian, Shivshankar

    Conventional engineered wood composites are bonded for the most part through formaldehyde-based structural adhesives such as urea formaldehyde (UF), melamine formaldehyde (MF), phenol formaldehyde (PF) and resorcinol formaldehyde (RF). Formaldehyde is a known human carcinogen; the occupational exposure and emission after manufacturing of these binders is raising more and more concern. With increasing emphasis on environmental issues, there is clear incentive to replace these hazardous conventional formaldehyde-based binders with cco-friendly resins having similar properties but derived from renewable sources, bearing in mind the economics of the structural wood composite industry. In this thesis, the curing reaction of bio-derived epoxy thermosets with inexpensive, low-toxicity precursors, including polyimines and amino acids was investigated. Epoxidized linseed oil (ELO) and epoxidized soybean oil (ESO) were successfully crosslinked with both branched polyethyleneimine (PEI) and triethylenetetramine (fETA). Epoxidized castor oil (ECO) was crosslinked with polyethyleneimine (PEI), having different molecular weights. Curing conditions were optimized through solvent uptake and soluble fraction analysis. Finally, the mechanical properties of the optimized compositions of rigid bioepoxies were evaluated using dynamic mechanical rheological testing (DMRT). While not as stiff as conventional materials, optimized materials have sufficient room temperature moduli to show promise for coatings and as binders in engineered wood products.

  19. Kinetic Resolution in Asymmetric Epoxidation using Iminium Salt Catalysis

    PubMed Central

    2013-01-01

    The first reported examples of kinetic resolution in epoxidation reactions using iminium salt catalysis are described, providing up to 99% ee in the epoxidation of racemic cis-chromenes. PMID:23862687

  20. 21 CFR 177.1010 - Acrylic and modified acrylic plastics, semirigid and rigid.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Acrylic and modified acrylic plastics, semirigid... Acrylic and modified acrylic plastics, semirigid and rigid. Semirigid and rigid acrylic and modified acrylic plastics may be safely used as articles intended for use in contact with food, in accordance...

  1. 21 CFR 177.1010 - Acrylic and modified acrylic plastics, semirigid and rigid.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Acrylic and modified acrylic plastics, semirigid... Acrylic and modified acrylic plastics, semirigid and rigid. Semirigid and rigid acrylic and modified acrylic plastics may be safely used as articles intended for use in contact with food, in accordance...

  2. 21 CFR 177.1010 - Acrylic and modified acrylic plastics, semirigid and rigid.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Acrylic and modified acrylic plastics, semirigid... Acrylic and modified acrylic plastics, semirigid and rigid. Semirigid and rigid acrylic and modified acrylic plastics may be safely used as articles intended for use in contact with food, in accordance...

  3. 40 CFR 721.10233 - Linear alkyl epoxide (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Linear alkyl epoxide (generic). 721... Substances § 721.10233 Linear alkyl epoxide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as linear alkyl epoxide (PMN...

  4. 40 CFR 721.10233 - Linear alkyl epoxide (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Linear alkyl epoxide (generic). 721... Substances § 721.10233 Linear alkyl epoxide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as linear alkyl epoxide (PMN...

  5. 40 CFR 721.10233 - Linear alkyl epoxide (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Linear alkyl epoxide (generic). 721... Substances § 721.10233 Linear alkyl epoxide (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as linear alkyl epoxide (PMN...

  6. 40 CFR 721.2673 - Aromatic epoxide resin (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Aromatic epoxide resin (generic). 721... Substances § 721.2673 Aromatic epoxide resin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as aromatic epoxide resin (PMN...

  7. 40 CFR 721.2673 - Aromatic epoxide resin (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Aromatic epoxide resin (generic). 721... Substances § 721.2673 Aromatic epoxide resin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as aromatic epoxide resin (PMN...

  8. 40 CFR 721.2673 - Aromatic epoxide resin (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Aromatic epoxide resin (generic). 721... Substances § 721.2673 Aromatic epoxide resin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as aromatic epoxide resin (PMN...

  9. 40 CFR 721.2673 - Aromatic epoxide resin (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Aromatic epoxide resin (generic). 721... Substances § 721.2673 Aromatic epoxide resin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as aromatic epoxide resin (PMN...

  10. Asymmetric Epoxidation Using Hydrogen Peroxide as Oxidant.

    PubMed

    Wang, Chuan; Yamamoto, Hisashi

    2015-10-01

    Asymmetric epoxidation is one of the most important transformations in organic synthesis. Although tremendous progress was achieved in this field in the 1980s and 1990s, it is still desirable from both economical and ecological views to develop environmentally friendly catalytic epoxidation with a broad substrate scope. Hydrogen peroxide is a safe and cheap oxidant, which is easy to handle and generates water as the sole byproduct. Therefore, asymmetric epoxidation of olefins using hydrogen peroxide as oxidant has been a very active research field and has been investigated by many research groups in recent years. In this review, the exciting very recent developments of this rapidly growing area are surveyed and organized according to the catalyst systems.

  11. Organocatalytic Asymmetric Reactions of Epoxides: Recent Progress.

    PubMed

    Meninno, Sara; Lattanzi, Alessandra

    2016-03-01

    In this Minireview recent advances in the asymmetric reactions of meso and racemic epoxides promoted by organocatalysts is reviewed. Organic promoters, such as chiral phosphoric acids, amino- and peptidyl thioureas, and sulfinamides, have been successfully used for a variety of enantioselective transformations of epoxides under catalytic conditions, involving direct nucleophilic attack at the oxirane ring, base-catalysed β-eliminations and Brønsted acid catalysed 1,2-rearrangements. Accordingly, highly valuable enantioenriched 1,2-functionalised alcohols, carbonyl compounds and nitroepoxides are attainable. Dual activation of the reagents, provided by the organocatalysts, appears to be the most recurrent strategy, potentially suitable to face other unmet challenges in asymmetric ring-opening reactions of epoxides.

  12. Synthesis of diethylamine-functionalized soybean oil.

    PubMed

    Biswas, Atanu; Adhvaryu, Atanu; Gordon, Sherald H; Erhan, Sevim Z; Willett, Julious L

    2005-11-30

    Specialty chemicals based on renewable resources are desirable commodities due to their eco-friendly nature and "green" product characteristics. These chemicals can demonstrate physical and chemical properties comparable to those of conventional petroleum-based products. Suitably functionalized amines in the triacylglycerol structure can function as an antioxidant, as well as an antiwear/antifriction agent. In addition, the amphiphilic nature of seed oils makes them an excellent candidate as base fluid. The reaction of amine and epoxidized seed oils in the presence of a catalyst almost always leads to different intra/intermolecular cross-linked products. In most cases, the triacylglycerol structure is lost due to disruption of the ester linkage. Currently, there is no reported literature describing the aminolysis of vegetable oil without cross-linking. Here the epoxy group of the epoxidized soybean oil has been selectively reacted with amines to give amine-functionalized soybean oil. The optimization procedure involved various amines and catalysts for maximum aminolysis, without cross-linking and disruption of the ester linkage. Diethylamine and ZnCl2 were found to be the best. NMR, IR, and nitrogen analysis were used to characterize the products. PMID:16302766

  13. Heterogeneous reactions of epoxides in acidic media.

    PubMed

    Lal, Vinita; Khalizov, Alexei F; Lin, Yun; Galvan, Maria D; Connell, Brian T; Zhang, Renyi

    2012-06-21

    Epoxides have recently been identified as important intermediates in the gas phase oxidation of hydrocarbons, and their hydrolysis products have been observed in ambient aerosols. To evaluate the role of epoxides in the formation of secondary organic aerosols (SOA), the kinetics and mechanism of heterogeneous reactions of two model epoxides, isoprene oxide and α-pinene oxide, with sulfuric acid, ammonium bisulfate, and ammonium sulfate have been investigated using complementary experimental techniques. Kinetic experiments using a fast flow reactor coupled to an ion drift-chemical ionization mass spectrometer (ID-CIMS) show a fast irreversible loss of the epoxides with the uptake coefficients (γ) of (1.7 ± 0.1) × 10(-2) and (4.6 ± 0.3) × 10(-2) for isoprene oxide and α-pinene oxide, respectively, for 90 wt % H(2)SO(4) and at room temperature. Experiments using attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR) reveal that diols are the major products in ammonium bisulfate and dilute H(2)SO(4) (<25 wt %) solutions for both epoxides. In concentrated H(2)SO(4) (>65 wt %), acetals are formed from isoprene oxide, whereas organosulfates are produced from α-pinene oxide. The reaction of the epoxides with ammonium sulfate is slow and no products are observed. The epoxide reactions using bulk samples and Nuclear Magnetic Resonance (NMR) spectroscopy reveal the presence of diols as the major products for isoprene oxide, accompanied by aldehyde formation. For α-pinene oxide, organosulfate formation is observed with a yield increasing with the acidity. Large yields of organosulfates in all NMR experiments with α-pinene oxide are attributed to the kinetic isotope effect (KIE) from the use of deuterated sulfuric acid and water. Our results suggest that acid-catalyzed hydrolysis of epoxides results in the formation of a wide range of products, and some of the products have low volatility and contribute to SOA growth under ambient conditions

  14. Alkene epoxidation employing metal nitro complexes

    DOEpatents

    Andrews, M.A.; Cheng, C.W.; Kelley, K.P.

    1982-07-15

    Process for converting alkenes to form epoxides utilizes transition metal nitro complexes of the formula: M(RCN)/sub 2/XNO/sub 2/ wherein M is palladium or platinum, R is an alkyl or aryl group containing up to 12 carbon atoms, and X is a monoanionic, monodentate ligand such as chlorine, optionally in the presence of molecular oxygen.

  15. Epoxidation of Methyl Oleate using Heterogeneous Catalyst

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In this work we studied the catalytic activity of commercial alumina, and laboratory synthesized alumina doped with Lewis acid metals, in the epoxidation of methyl oleate with aqueous hydrogen peroxide. It was observed that the reaction yields increased when the amount of catalyst, the quantity of ...

  16. Limonene-1,2-Epoxide Hydrolase from Rhodococcus erythropolis DCL14 Belongs to a Novel Class of Epoxide Hydrolases

    PubMed Central

    van der Werf, Mariët J.; Overkamp, Karin M.; de Bont, Jan A. M.

    1998-01-01

    An epoxide hydrolase from Rhodococcus erythropolis DCL14 catalyzes the hydrolysis of limonene-1,2-epoxide to limonene-1,2-diol. The enzyme is induced when R. erythropolis is grown on monoterpenes, reflecting its role in the limonene degradation pathway of this microorganism. Limonene-1,2-epoxide hydrolase was purified to homogeneity. It is a monomeric cytoplasmic enzyme of 17 kDa, and its N-terminal amino acid sequence was determined. No cofactor was required for activity of this colorless enzyme. Maximal enzyme activity was measured at pH 7 and 50°C. None of the tested inhibitors or metal ions inhibited limonene-1,2-epoxide hydrolase activity. Limonene-1,2-epoxide hydrolase has a narrow substrate range. Of the compounds tested, only limonene-1,2-epoxide, 1-methylcyclohexene oxide, cyclohexene oxide, and indene oxide were substrates. This report shows that limonene-1,2-epoxide hydrolase belongs to a new class of epoxide hydrolases based on (i) its low molecular mass, (ii) the absence of any significant homology between the partial amino acid sequence of limonene-1,2-epoxide hydrolase and amino acid sequences of known epoxide hydrolases, (iii) its pH profile, and (iv) the inability of 2-bromo-4′-nitroacetophenone, diethylpyrocarbonate, 4-fluorochalcone oxide, and 1,10-phenanthroline to inhibit limonene-1,2-epoxide hydrolase activity. PMID:9748436

  17. [Acrylic resin removable partial dentures].

    PubMed

    de Baat, C; Witter, D J; Creugers, N H J

    2011-01-01

    An acrylic resin removable partial denture is distinguished from other types of removable partial dentures by an all-acrylic resin base which is, in principle, solely supported by the edentulous regions of the tooth arch and in the maxilla also by the hard palate. When compared to the other types of removable partial dentures, the acrylic resin removable partial denture has 3 favourable aspects: the economic aspect, its aesthetic quality and the ease with which it can be extended and adjusted. Disadvantages are an increased risk of caries developing, gingivitis, periodontal disease, denture stomatitis, alveolar bone reduction, tooth migration, triggering of the gag reflex and damage to the acrylic resin base. Present-day indications are ofa temporary or palliative nature or are motivated by economic factors. Special varieties of the acrylic resin removable partial denture are the spoon denture, the flexible denture fabricated of non-rigid acrylic resin, and the two-piece sectional denture. Furthermore, acrylic resin removable partial dentures can be supplied with clasps or reinforced by fibers or metal wires.

  18. Fungal epoxide hydrolases: new landmarks in sequence-activity space.

    PubMed

    Smit, Martha S

    2004-03-01

    Epoxide hydrolases are useful catalysts for the hydrolytic kinetic resolution of epoxides, which are sought after intermediates for the synthesis of enantiopure fine chemicals. The epoxide hydrolases from Aspergillus niger and from the basidiomycetous yeasts Rhodotorula glutinis and Rhodosporidium toruloides have demonstrated potential as versatile, user friendly biocatalysts for organic synthesis. A recombinant A. niger epoxide hydrolase, produced by an overproducing A. niger strain, is already commercially available and recombinant yeast epoxide hydrolases expressed in Escherichia coli have shown excellent results. Within the vast body of activity information on the one hand and gene sequence information on the other hand, the epoxide hydrolases from the Rhodotorula spp. and A. niger stand out because we have sequence information as well as activity information for both the wild-type and recombinant forms of these enzymes.

  19. Thermochemical Studies of Epoxides and Related Compounds

    PubMed Central

    Morgan, Kathleen M.; Ellis, Jamie A.; Lee, Joseph; Fulton, Ashley; Wilson, Shavonda L.; Dupart, Patrick S.; Dastoori, Rosanna

    2013-01-01

    Gas phase heats of formation for the our butene oxide isomers are reported. They were obtained by measuring the condensed-phase heat of reduction to the corresponding alcohol using reaction calorimetry. Heats of vaporization were determined, and allow gas-phase heats of formation to be obtained. The experimental measurements are compared to calculations obtained using a variety of computational methods. Overall, the G3 and CBS-APNO methods agree quite well with the experimental data. The influence of alkyl substituents on epoxide stability is discussed. Comparisons to alkenes, cyclopropanes, aziridines, thiiranes and phosphiranes are also made. Isodesmic-type reactions were used to determine strain energies of the epoxides and related compounds with various substituents. PMID:23551240

  20. Simple Epoxide Formation for the Organic Laboratory Using Oxone

    ERIC Educational Resources Information Center

    Broshears, Williams C.; Esteb, John J.; Richter, Jeremy; Wilson, Anne M.

    2004-01-01

    Epoxide chemistry is widely used in organic synthesis and regularly discussed in organic chemistry textbooks. An experiment to generate dimethyldioxirane in situ from acetone using Oxone is explained.

  1. Synthesis and characterization of polyurethanes made from copolymers of epoxidized natural oil and tetrahydrofuran.

    PubMed

    Hoong, Seng Soi; Yeong, Shoot Kian; Hassan, Hazimah Abu; Din, Ahmad Kushairi; Choo, Yuen May

    2015-01-01

    Polyols were synthesized from epoxidized natural oils and tetrahydrofuran through ring opening copolymerization catalyzed by Lewis acid. The properties of these polyols depend on the type of natural oils as well as the reaction conditions (monomer concentration, catalyst amount, reaction temperature and reaction time). These polyols were evaluated as a raw material for making polyurethane (PU) in order to understand the structure-property relationship between a natural oil and PU made from it. The tensile test analysis shows that the incorporation of natural oil moiety into the PU polymer network improves the elasticity of these PU samples when compared to a benchmark PU sample. In addition, the PU samples made from palm oil and soybean oil based polyols exhibit better tensile strength than benchmark PU. These polyols samples are suitable for making elastomeric PU, where high flexibility (high elongation at break) of PU is a common requirement. PMID:25492233

  2. Bonding auto-polymerising acrylic resin to acrylic denture teeth.

    PubMed

    Nagle, Susan; Ray, Noel J; Burke, Francis M; Gorman, Catherine M

    2009-09-01

    This study investigated the effect of surface treatments on the shear bond strength of an auto-polymerising acrylic resin cured to acrylic denture teeth. The surface treatments included a combination of grit-blasting and/or wetting the surface with monomer. Samples were prepared and then stored in water prior to shear testing. The results indicated that the application of monomer to the surface prior to bonding did not influence the bond strength. Grit blasting was found to significantly increase the bond strength. PMID:19839190

  3. Epoxide ring-opening and Meinwald rearrangement reactions of epoxides catalyzed by mesoporous aluminosilicates.

    PubMed

    Robinson, Mathew W C; Davies, A Matthew; Buckle, Richard; Mabbett, Ian; Taylor, Stuart H; Graham, Andrew E

    2009-06-21

    Mesoporous aluminosilicates efficiently catalyze the ring-opening of epoxides to produce beta-alkoxyalcohols in high yields under extremely mild reaction conditions. These materials also catalyze the corresponding Meinwald rearrangement in non-nucleophilic solvents to give aldehydes which can be trapped in situ to provide the corresponding acetals in an efficient tandem process.

  4. Functionalized oxepines via fragmentation of highly strained epoxides.

    PubMed

    Leyhane, Andrew J; Snapper, Marc L

    2006-11-01

    [Structure: see text] Epoxidation of highly strained cyclobutenes followed by thermal rearrangement provides a new entry into oxepine-containing bicyclo[5.3.0] ring systems. In contrast to the rearrangement of the corresponding cyclopropanated systems, the strained epoxides in this study are believed to fragment through two competing pathways leading to a mixture of diastereomeric 5-7 ring systems.

  5. Epoxides--is there a human health problem?

    PubMed Central

    Manson, M M

    1980-01-01

    The purpose of this review is to consider whether epoxides represent a hazard to human health. Possible means of occupational and non-occupational exposure are discussed with reference to the production and uses of industrially important compounds and other epoxides, such as naturally occurring plant and fungal products. In addition to epoxides themselves, unsaturated compounds that may be metabolised in vivo to epoxides are included, since this appears to be a further important means of exposure. The toxicology, in particular carcinogenicity and mutagenicity, is discussed, along with a brief outline of the biochemistry such as metabolism, binding to cell constituents, and DNA repair mechanisms. The question of interactions between different epoxides in vivo is also raised. PMID:7004476

  6. Identification of Epoxide-Derived Metabolite(s) of Benzbromarone.

    PubMed

    Wang, Kai; Wang, Hui; Peng, Ying; Zheng, Jiang

    2016-04-01

    Benzbromarone (BBR) is a benzofuran derivative that has been quite useful for the treatment of gout; however, it was withdrawn from European markets in 2003 because of reported serious incidents of drug-induced liver injury. BBR-induced hepatotoxicity has been suggested to be associated with the formation of a quinone intermediate. The present study reported epoxide-derived intermediate(s) of BBR. An N-acetylcysteine (NAC) conjugate derived from epoxide metabolite(s) was detected in both microsomal incubations of BBR and urine samples of mice treated with BBR. The NAC conjugate was identified as 6-NAC BBR. Ketoconazole suppressed the bioactivation of BBR to the epoxide intermediate(s), and the CYP3A subfamily was the primary enzyme responsible for the formation of the epoxide(s). The present study provided new information on metabolic activation of BBR. PMID:26792818

  7. NMR studies on epoxidations of allenamides. Evidence for formation of nitrogen-substituted allene oxide and spiro-epoxide via trapping experiments.

    PubMed

    Rameshkumar, C; Xiong, Hui; Tracey, Michael R; Berry, Craig R; Yao, Letitia J; Hsung, Richard P

    2002-02-22

    Two epoxidations of chiral allenamides are described here. While treatment with m-CPBA led to highly stereoselective formation of an alpha-keto aminal that can be useful synthetically, DMDO oxidation led to conclusive evidence for both nitrogen-substituted allene oxide (via mono-epoxidation) and spiro-epoxide (via bis-epoxidation) using intramolecular nucleophilic trapping experiments. NMR studies provide reliable evidence for a 3-oxetanone that can be derived from the spiro-epoxide and also suggest the presence of an allene oxide. Despite a facile second epoxidation as evidenced by the predominant formation of the 3-oxetanone, in the presence of furan, [4 + 3] cycloaddition of the nitrogen-substituted allene oxide or oxyallyl cation with furan occurs faster than the second epoxidation efficiently leading to cycloadducts. This rate difference plays an invaluable role for the success of a stereoselective sequential epoxidation-[4 + 3] cycloaddition reaction via DMDO epoxidations of chiral allenamides.

  8. 40 CFR 721.2805 - Acrylate ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acrylate ester. 721.2805 Section 721... Acrylate ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an acrylate ester (PMN P-96-824) is subject to reporting under...

  9. 40 CFR 721.2805 - Acrylate ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Acrylate ester. 721.2805 Section 721... Acrylate ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an acrylate ester (PMN P-96-824) is subject to reporting under...

  10. 40 CFR 721.2805 - Acrylate ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Acrylate ester. 721.2805 Section 721... Acrylate ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an acrylate ester (PMN P-96-824) is subject to reporting under...

  11. 40 CFR 721.2805 - Acrylate ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acrylate ester. 721.2805 Section 721... Acrylate ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an acrylate ester (PMN P-96-824) is subject to reporting under...

  12. Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions

    ERIC Educational Resources Information Center

    Mak, Kendrew K. W.; Lai, Y. M.; Siu, Yuk-Hong

    2006-01-01

    This article describes a discovery-oriented experiment for demonstrating the selectivity of two epoxidation reactions. Peroxy acids and alkaline H[subscript 2]O[subscript 2] are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich alkenes while the latter works better with alpha,beta-unsaturated…

  13. Utilizing soybean milk to culture soybean pathogens

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Liquid and semi-solid culture media are used to maintain and proliferate bacteria, fungi, and Oomycetes for research in microbiology and plant pathology. In this study, a comparison was made between soybean milk medium, also referred to as soymilk, and media traditionally used for culturing soybean ...

  14. Mixing It Up with Acrylics.

    ERIC Educational Resources Information Center

    Laird, Shirley

    1999-01-01

    Presents an art activity for fifth-grade students in which they learn about basic shapes and what happens when shapes overlap, draw seven overlapping geometric shapes, review the use of acrylic paint and mixing colors, and finally paint with primary colors. (CMK)

  15. Thermodynamic and kinetic evaluation of the polymerization process of epoxidized biodiesel with dicarboxylic anhydride

    NASA Astrophysics Data System (ADS)

    da Roza, Miriam B.; Nicolau, Aline; Angeloni, Luiz M.; Sidou, Pedro N.; Samios, Dimitrios

    2012-06-01

    This paper reports on a polymerization study of the epoxidized methyl esters (EME) obtained from soybean oil, with phthalic anhydride (PA) and 2-methyl-imidazole in the presence of soybean oil biodiesel (BD) as solvent. The gelation region for the system EME/PA/2MI without BD was determined using the Flory's theory occurring between X EME = 0.33 to 0.54. The evaluation of the polymerization enthalpy (ΔH) indicates that the experimental stoichiometric composition of the system EME/PA/2MI without solvent is near to X EME = X PA = 0.5. ΔH values higher than 76 J/g were observed for samples located in the theoretical gelation region. Different polymers were produced using the stoichiometric composition and varying only the amount of BD. Kinetics and thermodynamics of the polymerization reaction, using solvent, were evaluated by DSC technique. The results show that BD acts as solvent in the polymerization reaction and a compensation effect between activation energy and logarithm of pre-exponential factor was observed. Thermogravimetric analysis indicated that the degradations of the products include two well-defined processes. The compensation effect was observed in the thermal degradation kinetics too.

  16. Inhibiting an epoxide hydrolase virulence strategy protects CFTR**

    PubMed Central

    Bahl, Christopher D.; Hvorecny, Kelli L.; Bomberger, Jennifer M.; Stanton, Bruce A.; Hammock, Bruce D.; Morisseau, Christophe; Madden, Dean R.

    2015-01-01

    Opportunistic pathogens exploit diverse strategies to sabotage host defenses. Pseudomonas aeruginosa secretes the CFTR inhibitory factor Cif and thus triggers loss of CFTR, an ion channel required for airway mucociliary defense. However, Cif's mechanism of action has remained unclear. It catalyzes epoxide hydrolysis, but there is no known role for natural epoxides in CFTR regulation. Here, we show that Cif's hydrolase activity is strictly required for its effects on CFTR. We also uncover a small-molecule inhibitor that protects this key component of the mucociliary defense system. Our results provide a basis for targeting Cif's distinctive virulence chemistry and suggest an unanticipated role of physiological epoxides in intracellular protein trafficking. PMID:26136396

  17. Orally Bioavailable Potent Soluble Epoxide Hydrolase Inhibitors

    PubMed Central

    Hwang, Sung Hee; Tsai, Hsing-Ju; Liu, Jun-Yan; Morisseau, Christophe; Hammock, Bruce D.

    2008-01-01

    A series of N,N′-disubstituted ureas having a conformationally restricted cis- or trans-1,4-cyclohexane α to the urea were prepared and tested as soluble epoxide hydrolase (sEH) inhibitors. This series of compounds showed low nanomolar to picomolar activities against recombinant human sEH. Both isomers showed similar potencies, but the trans isomers were more metabolically stable in human hepatic microsomes. Furthermore, these new potent inhibitors show a greater metabolic stability in vivo than previously described sEH inhibitors. We demonstrated that trans-4-[4-(3-adamantan-1-ylureido)cyclohexyloxy]benzoic acid 13g (t-AUCB, IC50 = 1.3 ± 0.05 nM) had excellent oral bioavailability (98%, n = 2) and blood area under the curve in dogs and was effective in vivo to treat hypotension in lipopolysaccharide challenged murine models. PMID:17616115

  18. Investigation of copper(II) tetrafluoroborate catalysed epoxide opening

    PubMed Central

    Capes, Amy S.; Crossman, Arthur T.; Webster, Lauren A.; Ferguson, Michael A.J.; Gilbert, Ian H.

    2011-01-01

    We report the extension of the copper(II) tetrafluoroborate catalysed opening of epoxides with alcohols to include a wider variety of alcohols, a range of solvents and a method to purify the products from the reaction. PMID:22505782

  19. Molecular Epoxidation Reactions Catalyzed by Rhenium, Molybdenum, and Iron Complexes.

    PubMed

    Kück, Jens W; Reich, Robert M; Kühn, Fritz E

    2016-02-01

    Epoxidations are of high relevance in many organic syntheses, both in industry and academia. In this personal account, the development of rhenium, molybdenum, and iron complexes in molecular epoxidation catalysis is presented. Methyltrioxorhenium (MTO) is the benchmark catalyst for these reactions, with a thoroughly investigated mechanism and reactivity profile. More recently, highly active molecular molybdenum and iron catalysts have emerged, challenging the extraordinary role of MTO in epoxidation catalysis with high turnover frequencies (TOFs). This development is highlighted in its use of cheaper, more readily available metals, and the challenges of using base metals in catalysis are discussed. These results show the promise that relatively cheap and abundant metals, such as molybdenum and iron, hold for the future of epoxidation catalysis. PMID:26776087

  20. Genotoxicity characteristics of reverse diol-epoxides of chrysene.

    PubMed

    Glatt, H; Wameling, C; Elsberg, S; Thomas, H; Marquardt, H; Hewer, A; Phillips, D H; Oesch, F; Seidel, A

    1993-01-01

    Trans-3,4-dihydroxy-3,4-dihydrochrysene (chrysene-3,4-diol), a major metabolite of chrysene, is further metabolized by rat liver enzymes to products which effectively revert the his- Salmonella typhimurium strain TA98 to histidine prototrophy, but are only weakly mutagenic in strain TA100 and in Chinese hamster V79 cells (acquisition of resistance to 6-thioguanine). The liver enzyme mediated mutagenicity of chrysene-3,4-diol is substantially enhanced in the presence of 1,1,1-trichloropropene 2,3-oxide, an inhibitor of microsomal epoxide hydrolase. The predominant metabolites of chrysene-3,4-diol, namely the anti- and syn-isomers of its 1,2-oxide (termed reverse diol-epoxides), proved to be extraordinarily effective mutagens in S.typhimurium strain TA98, but were only moderately active in strains TA100 and TA104, and in the SOS induction in Escherichia coli PQ37. These genotoxicity spectra in bacteria are completely different from those observed with the bay-region diol-epoxides of chrysene and 3-hydroxychrysene. In V79 cells, the reverse diol-epoxides formed low levels of DNA adducts and were very weak inducers of gene mutations. In M2 mouse prostate cells, however, high numbers of transformed foci were induced by chrysene-3,4-diol and its diastereomeric 1,2-oxides. Chrysene-3,4-diol was somewhat more potent than chrysene-1,2-diol. The potency of both reverse diol-epoxides was similar to that of the syn-diastereomers of the bay-region diol-epoxides of chrysene and 3-hydroxychrysene, but lower than that of their anti-diastereomers. The reverse diol-epoxides of chrysene, unlike the bay-region diol-epoxides, were inactivated by purified microsomal epoxide hydrolase. Noteworthy findings were also made with regard to the chemical stability of the diol-epoxides in buffer, determined from the decline in mutagenicity after preincubation in the absence of the target cells. Despite its lower delta Edeloc/beta value for the formation of the benzylic carbocation, anti

  1. A method for preparing sodium acrylate-d3, a useful and stable precursor for deuterated acrylic monomers

    SciTech Connect

    Yang, Jun; Hong, Kunlun; Bonnesen, Peter V

    2011-01-01

    A convenient and economical method for converting propiolic acid to sodium acrylate-d3 is described. Successive D/H exchange of the alkyne proton of sodium propiolate (prepared from propiolic acid) using D2O affords sodium propiolate-d having up to 99 atom% D. Sodium propiolate-d can be partially reduced to sodium acrylate-d3 with 90% conversion and 89% yield, using D2 and the Lindlar catalyst with control of reaction parameters to maximize conversion while minimizing over reduction.

  2. Esterification of acrylic acid with methanol

    SciTech Connect

    Chubarov, G.A.; Danov, S.M.; Logutov, V.I.; Obmelyukhina, T.N.

    1984-01-01

    The esterification of acrylic acid with methanol in the absence of catalysis by strong mineral acids has been studied. The esterification rate was estimated from the amount of methyl acrylate formed at the end of a definite time, and the reaction rate was found to be first order with respect to methanol and second order with respect to acrylic acid. Mathematical relationships in good agreement with experimental data were derived from the results of the kinetic studies.

  3. Immunohistochemical study of epoxide hydrolase induced by trichloroethylene in rat liver

    SciTech Connect

    Kawamoto, T.; Hobara, T.; Ogino, K.; Takemoto, T.; Nakamura, K.; Imamura, A.; Koshiro, A.; Kobayashi, H.; Iwamoto, S.; Sakai, T.

    1987-10-01

    Epoxide hydrolase catalyzes the hydrolation of potentially toxic, electrophilic epoxides that are often generated during cytochrome P-450 catalyzed monooxigenation, forming the corresponding transdihydrodiols. It is well-known that trichloroethylene is metabolized by cytochrome P-450 containing mixed-function oxidase systems to trichloroethylene oxide, which decomposes to other metabolites. As trichloroethylene is an epoxide, epoxide hydrolase is suspected to catalyze the hydrolation of trichloroethylene oxide. No reports have appeared about the relationship between trichloroethylene and epoxide hydrolase. In this report, the authors studied the effect of trichloroethylene on epoxide hydrolase immunohistochemically.

  4. Soybean Production Lesson Plan.

    ERIC Educational Resources Information Center

    Carlson, Keith R.

    These lesson plans for teaching soybean production in a secondary or postsecondary vocational agriculture class are organized in nine units and cover the following topics: raising soybeans, optimum tillage, fertilizer and lime, seed selection, pest management, planting, troubleshooting, double cropping, and harvesting. Each lesson plan contains…

  5. Soybean irrigation management

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean is an important crop and a major component of the agricultural economy in the Missouri Bootheel and throughout Missouri. USDA’s National Agricultural Statistics Service (NASS) reported that in 2012, 960 thousand acres of soybeans were harvested in Southeast Missouri (Butler, Cape Girardeau, ...

  6. 40 CFR 721.2805 - Acrylate ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acrylate ester. 721.2805 Section 721... Acrylate ester. Link to an amendment published at 79 FR 34637, June 18, 2014. (a) Chemical substance and... ester (PMN P-96-824) is subject to reporting under this section for the significant new uses...

  7. Formation of furan fatty alkyl esters from their bis-epoxide fatty esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Epoxidation of vegetable oils and consecutive epoxide ring-opening reaction is a widely investigated path for producing biobased lubricants and polymers. The reaction mechanism and products are considered well-studied and known. In the current study, the reactions of epoxidized alkyl soyate with fou...

  8. Cu-catalyzed cross-coupling reactions of epoxides with organoboron compounds.

    PubMed

    Lu, Xiao-Yu; Yang, Chu-Ting; Liu, Jing-Hui; Zhang, Zheng-Qi; Lu, Xi; Lou, Xin; Xiao, Bin; Fu, Yao

    2015-02-11

    A copper-catalyzed cross-coupling reaction of epoxides with arylboronates is described. This reaction is not limited to aromatic epoxides, because aliphatic epoxides are also suitable substrates. In addition, N-sulfonyl aziridines can be successfully converted into the products. This reaction provides convenient access to β-phenethyl alcohols, which are valuable synthetic intermediates. PMID:25564373

  9. Sulfuric acid as a catalyst for ring-opening of biobased bis-epoxides

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Vegetable oils can be relatively and easily transformed into bio-based epoxides. Because of this, the acid-catalyzed epoxide ring-opening has been explored for the preparation of bio-based lubricants and polymers. Detailed model studies are carried out only with mono-epoxide made from methyl oleate,...

  10. Soluble epoxide hydrolase: Gene structure, expression and deletion

    PubMed Central

    Harris, Todd R.; Hammock, Bruce D.

    2013-01-01

    Mammalian soluble epoxide hydrolase (sEH) converts epoxides to their corresponding diols through the addition of a water molecule. sEH readily hydrolyzes lipid signaling molecules, including the epoxyeicosatrienoic acids (EETs), epoxidized lipids produced from arachidonic acid by the action of cytochrome p450s. Through its metabolism of the EETs and other lipid mediators, sEH contributes to the regulation of vascular tone, nociception, angiogenesis and the inflammatory response. Because of its central physiological role in disease states such as cardiac hypertrophy, diabetes, hypertension, and pain sEH is being investigated as a therapeutic target. This review begins with a brief introduction to sEH protein structure and function. sEH evolution and gene structure are then discussed before human small nucleotide polymorphisms and mammalian gene expression are described in the context of several disease models. The review ends with an overview of studies that have employed the sEH knockout mouse model. PMID:23701967

  11. Epoxide Chemistry: Guided Inquiry Experiment Emphasizing Structure Determination and Mechanism

    NASA Astrophysics Data System (ADS)

    Krishnamurty, H. G.; Jain, Niveta; Samby, Kiran

    2000-04-01

    This paper presents an operationally simple three-step synthesis of an a-hydroxy acid based on epoxide chemistry. The focus of the experiment is on the preparation of the chalcone epoxide and its reaction with hot alcoholic alkali. The experiment leads to an unpredicted reaction product. Its structure is established as 2-benzyl-2-phenylglycollic acid by chemical and spectroscopic analysis. The hydroxyacid is a good example to bring home an important NMR principle: the nonequivalence of hydrogens adjacent to a stereogenic center. The formation of the alpha-hydroxy acid is a mechanistic puzzle. A stepwise mechanism can be developed applying lecture-based organic chemistry concepts. On the other hand, acid-catalyzed (H2SO4, BF3) reaction of the chalcone epoxide gives benzoylphenylacetaldehyde. The exercise can be used as a multistep organic chemistry experiment. It also gives students a research-type experience.

  12. Soluble epoxide hydrolase: gene structure, expression and deletion.

    PubMed

    Harris, Todd R; Hammock, Bruce D

    2013-09-10

    Mammalian soluble epoxide hydrolase (sEH) converts epoxides to their corresponding diols through the addition of a water molecule. sEH readily hydrolyzes lipid signaling molecules, including the epoxyeicosatrienoic acids (EETs), epoxidized lipids produced from arachidonic acid by the action of cytochrome p450s. Through its metabolism of the EETs and other lipid mediators, sEH contributes to the regulation of vascular tone, nociception, angiogenesis and the inflammatory response. Because of its central physiological role in disease states such as cardiac hypertrophy, diabetes, hypertension, and pain sEH is being investigated as a therapeutic target. This review begins with a brief introduction to sEH protein structure and function. sEH evolution and gene structure are then discussed before human small nucleotide polymorphisms and mammalian gene expression are described in the context of several disease models. The review ends with an overview of studies that have employed the sEH knockout mouse model. PMID:23701967

  13. The oxidation of copper catalysts during ethylene epoxidation.

    PubMed

    Greiner, M T; Jones, T E; Johnson, B E; Rocha, T C R; Wang, Z J; Armbrüster, M; Willinger, M; Knop-Gericke, A; Schlögl, R

    2015-10-14

    The oxidation of copper catalysts during ethylene epoxidation was characterized using in situ photoemission spectroscopy and electron microscopy. Gas chromatography, proton-transfer reaction mass spectrometry and electron-ionization mass spectrometry were used to characterize the catalytic properties of the oxidized copper. We find that copper corrodes during epoxidation in a 1 : 1 mixture of oxygen and ethylene. The catalyst corrosion passes through several stages, beginning with the formation of an O-terminated surface, followed by the formation of Cu2O scale and eventually a CuO scale. The oxidized catalyst exhibits measurable activity for ethylene epoxidation, but with a low selectivity of <3%. Tests on pure Cu2O and CuO powders confirm that the oxides intrinsically exhibit partial-oxidation activity. Cu2O was found to form acetaldehyde and ethylene epoxide in roughly equal amounts (1.0% and 1.2% respectively), while CuO was found to form much less ethyl aldehyde than ethylene epoxide (0.1% and 1.0%, respectively). Metallic copper catalysts were examined in extreme dilute-O2 epoxidation conditions to try and keep the catalyst from oxidizing during the reaction. It was found that in feed of 1 part O2 to 2500 parts C2H4 (PO2 = 1.2 × 10(-4) mbar) the copper surface becomes O-terminated. The O-terminated surface was found to exhibit partial-oxidation selectivity similar to that of Cu2O. With increasing O2 concentration (>8/2500) Cu2O forms and eventually covers the surface.

  14. A strategy for position-selective epoxidation of polyprenols.

    PubMed

    Gnanadesikan, Vijay; Corey, E J

    2008-06-25

    An effective strategy has been developed for the efficient site-selective epoxidation of poylolefinic isoprenoid alcohols, based on the use of an internal control element for intramolecular reaction. The approach is illustrated by application to a series of polyisoprenoid alcohols (polyprenols) at substrate concentration of 0.5 mM. With polyprenol substrates having the hydroxyl function at one terminus, the internal epoxidation can be directed at the double bond of the polyprenol, which is either four or five away from the terminal hydroxyprenyl subunit.

  15. Radiopurity measurement of acrylic for DEAP-3600

    SciTech Connect

    Nantais, C. M.; Boulay, M. G.; Cleveland, B. T.

    2013-08-08

    The spherical acrylic vessel that contains the liquid argon target is the most critical detector component in the DEAP-3600 dark matter experiment. Alpha decays near the inner surface of the acrylic vessel are one of the main sources of background in the detector. A fraction of the alpha energy, or the recoiling nucleus from the alpha decay, could misreconstruct in the fiducial volume and result in a false candidate dark matter event. Acrylic has low levels of inherent contamination from {sup 238}U and {sup 232}Th. Another background of particular concern is diffusion of {sup 222}Rn during manufacturing, leading to {sup 210}Pb contamination. The maximum acceptable concentrations in the DEAP-3600 acrylic vessel are ppt levels of {sup 238}U and {sup 232}Th equivalent, and 10{sup −8} ppt {sup 210}Pb. The impurities in the bulk acrylic will be measured by vaporizing a large quantity of acrylic and counting the concentrated residue with ultra-low background HPGe detectors and a low background alpha spectrometer. An overview of the acrylic assay technique is presented.

  16. 21 CFR 177.1310 - Ethylene-acrylic acid copolymers.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Ethylene-acrylic acid copolymers. 177.1310 Section... Use Food Contact Surfaces § 177.1310 Ethylene-acrylic acid copolymers. The ethylene-acrylic acid... for use in contact with food subject to the provisions of this section. (a) The ethylene-acrylic...

  17. 21 CFR 176.110 - Acrylamide-acrylic acid resins.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Acrylamide-acrylic acid resins. 176.110 Section... Paper and Paperboard § 176.110 Acrylamide-acrylic acid resins. Acrylamide-acrylic acid resins may be...) Acrylamide-acrylic acid resins are produced by the polymerization of acrylamide with partial hydrolysis or...

  18. 21 CFR 573.120 - Acrylamide-acrylic acid resin.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Acrylamide-acrylic acid resin. 573.120 Section 573... Food Additive Listing § 573.120 Acrylamide-acrylic acid resin. Acrylamide-acrylic acid resin... acrylamide with partial hydrolysis, or by copolymerization of acrylamide and acrylic acid with the...

  19. 21 CFR 573.120 - Acrylamide-acrylic acid resin.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Acrylamide-acrylic acid resin. 573.120 Section 573... Food Additive Listing § 573.120 Acrylamide-acrylic acid resin. Acrylamide-acrylic acid resin... acrylamide with partial hydrolysis, or by copolymerization of acrylamide and acrylic acid with the...

  20. 21 CFR 573.120 - Acrylamide-acrylic acid resin.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Acrylamide-acrylic acid resin. 573.120 Section 573... Food Additive Listing § 573.120 Acrylamide-acrylic acid resin. Acrylamide-acrylic acid resin... acrylamide with partial hydrolysis, or by copolymerization of acrylamide and acrylic acid with the...

  1. 21 CFR 177.1060 - n-Alkylglutarimide/acrylic copolymers.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false n-Alkylglutarimide/acrylic copolymers. 177.1060... Use Food Contact Surfaces § 177.1060 n-Alkylglutarimide/acrylic copolymers. n-Alkylglutarimide/acrylic...) Identity. For the purpose of this section, n-alkylglutarimide/acrylic copolymers are copolymers obtained...

  2. 21 CFR 573.120 - Acrylamide-acrylic acid resin.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Acrylamide-acrylic acid resin. 573.120 Section 573... Food Additive Listing § 573.120 Acrylamide-acrylic acid resin. Acrylamide-acrylic acid resin... acrylamide with partial hydrolysis, or by copolymerization of acrylamide and acrylic acid with the...

  3. Seasonal soybean crop reflectance

    NASA Technical Reports Server (NTRS)

    Lemaster, E. W. (Principal Investigator); Chance, J. E.

    1983-01-01

    Data are presented from field measurements of 1980 including 5 acquisitions of handheld radiometer reflectance measurements, 7 complete sets of parameters for implementing the Suits mode, and other biophysical parameters to characterize the soybean canopy. LANDSAT calculations on the simulated Brazilian soybean reflectance are included along with data collected during the summer and fall on 1981 on soybean single leaf optical parameters for three irrigation treatments. Tests of the Suits vegetative canopy reflectance model for the full hemisphere of observer directions as well as the nadir direction show moderate agreement for the visible channels of the MSS and poor agreement in the near infrared channel. Temporal changes in the spectral characteristics of the single leaves were seen to occur as a function of maturity which demonstrates that the absorptance of a soybean single leaf is more a function of thetransmittancee characteristics than the seasonally consistent single leaf reflectance.

  4. Argentina soybean yield model

    NASA Technical Reports Server (NTRS)

    Callis, S. L.; Sakamoto, C.

    1984-01-01

    A model based on multiple regression was developed to estimate soybean yields for the country of Argentina. A meteorological data set was obtained for the country by averaging data for stations within the soybean growing area. Predictor variables for the model were derived from monthly total precipitation and monthly average temperature. A trend variable was included for the years 1969 to 1978 since an increasing trend in yields due to technology was observed between these years.

  5. Soybean aphid and soybean cyst nematode interactions in the field and effects on soybean yield.

    PubMed

    Hong, S C; MacGuidwin, A; Gratton, C

    2011-10-01

    How above- and belowground plant pests interact with each other and how these interactions affect productivity is a relatively understudied aspect of crop production. Soybean cyst nematode, Heterodera glycines Ichinohe, a root parasite of soybean, Glycine max (L.) Merr., is the most threatening pathogen in soybean production and soybean aphid, Aphis glycines Matsumura, an aboveground phloem-feeding insect that appeared in North America in 2000, is the key aboveground herbivore of soybean in the midwestern United States. Now, both soybean aphid and soybean cyst nematode co-occur in soybean-growing areas in the Upper Midwest. The objectives of this study were to examine aphid colonization patterns and population growth on soybean across a natural gradient of nematode density (range, approximately 900 and 27,000 eggs per 100 cm3 soil), and to investigate the effect of this pest complex on soybean productivity. Alate (winged) soybean aphid colonization of soybean was negatively correlated to soybean cyst nematode egg density (r = -0.363, P = 0.0095) at the end of July, at the onset of peak alate colonization. However, both a manipulative cage study and openly colonized plants showed that soybean cyst nematode density below ground was unrelated to variation in aphid population growth (r approximately -0.01). Based on regression analyses, soybean aphids and cyst nematodes had independent effects on soybean yield through effects on different yield components. High soybean cyst nematode density was associated with a decline in soybean yield (kg ha(-1)), whereas increasing soybean aphid density (both alate and apterous) significantly decreased seed weight (g 100 seeds(-1)).

  6. Protein profile of mature soybean seeds and prepared soybean milk.

    PubMed

    Capriotti, Anna Laura; Caruso, Giuseppe; Cavaliere, Chiara; Samperi, Roberto; Stampachiacchiere, Serena; Zenezini Chiozzi, Riccardo; Laganà, Aldo

    2014-10-01

    The soybean (Glycine max (L.) Merrill) is economically the most important bean in the world, providing a wide range of vegetable proteins. Soybean milk is a colloidal solution obtained as water extract from swelled and ground soybean seeds. Soybean proteins represent about 35-40% on a dry weight basis and they are receiving increasing attention with respect to their health effects. However, the soybean is a well-recognized allergenic food, and therefore, it is urgent to define its protein components responsible for the allergenicity in order to develop hypoallergenic soybean products for sensitive people. The main aim of this work was the characterization of seed and milk soybean proteome and their comparison in terms of protein content and specific proteins. Using a shotgun proteomics approach, 243 nonredundant proteins were identified in mature soybean seeds.

  7. Crystal structure transformation in potassium acrylate

    NASA Astrophysics Data System (ADS)

    Pai Verneker, V. R.; Vasanthakumari, R.

    1983-10-01

    Potassium acrylate undergoes a reversible phase transformation around 335°K with an activation energy of 133 kcal/mole. Differential scanning calorimetry and high temperature X-ray powder diffraction techniques have been used to probe this phenomenon.

  8. Encapsulation of photocells with acrylic prepolymer

    SciTech Connect

    Avenel, M.; Evrard, P.; Leca, J.-P.

    1985-10-22

    Acrylic prepolymer comprising: from 10 to 50% by weight of units derived from at least one alkyl acrylate, the alkyl group having from 4 to 12 carbon atoms, from 30 to 60% by weight of units derived from at least one alkyl methacrylate, the alkyl group having from 1 to 5 carbon atoms, and from 10 to 40% by weight of units derived from methyl acrylate. The prepolymer is used to encapsulate photocells, connected to one another by conducting wires and positioned on a support plate, by casting a resin into the space located between the support plate and a second protective plate, the resin being obtained by mixing 100 parts of the acrylic prepolymer, from 0.1 to 4 parts of a vanadium arenesulphonate and from 0.5 to 4 parts of a free-radical initiator, at a temperature between 10 and 70 C. and for a sufficient time to solidify the polymeric resin at the temperature selected.

  9. DEVELOPMENT OF METABOLICALLY STABLE INHIBITORS OF MAMMALIAN MICROSOMAL EPOXIDE HYDROLASE

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The microsomal epoxide hydrolase (mEH) plays a significant role in the metabolism of xenobiotics such as polyaromatic toxicants. Additionally, polymorphism studies have underlined a potential role of this enzyme in relation to a number of diseases, such as emphysema, spontaneous abortion, eclampsia ...

  10. Stability and friction reducing properties of epoxidized oleochemical methyl esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The use of oleochemicals as biobased replacements for petrochemical lubricants is an important area of study. Physical properties of the epoxidized fatty esters derived from vegetable oil are reported and compared to their olefinic counterparts. Overall the frictional behavior of epoxy methyl olea...

  11. A Photorhabdus natural product inhibits insect juvenile hormone epoxide hydrolase.

    PubMed

    Nollmann, Friederike I; Heinrich, Antje K; Brachmann, Alexander O; Morisseau, Christophe; Mukherjee, Krishnendu; Casanova-Torres, Ángel M; Strobl, Frederic; Kleinhans, David; Kinski, Sebastian; Schultz, Katharina; Beeton, Michael L; Kaiser, Marcel; Chu, Ya-Yun; Phan Ke, Long; Thanwisai, Aunchalee; Bozhüyük, Kenan A J; Chantratita, Narisara; Götz, Friedrich; Waterfield, Nick R; Vilcinskas, Andreas; Stelzer, Ernst H K; Goodrich-Blair, Heidi; Hammock, Bruce D; Bode, Helge B

    2015-03-23

    Simple urea compounds ("phurealipids") have been identified from the entomopathogenic bacterium Photorhabdus luminescens, and their biosynthesis was elucidated. Very similar analogues of these compounds have been previously developed as inhibitors of juvenile hormone epoxide hydrolase (JHEH), a key enzyme in insect development and growth. Phurealipids also inhibit JHEH, and therefore phurealipids might contribute to bacterial virulence. PMID:25711603

  12. 40 CFR 721.2673 - Aromatic epoxide resin (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Aromatic epoxide resin (generic). 721.2673 Section 721.2673 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2673 Aromatic...

  13. ULTRASOUND-ASSISTED ORGANIC SYNTHESIS: ALCOHOL OXIDATION AND OLEFIN EPOXIDATION

    EPA Science Inventory

    Ultrasound-assisted Organic Synthesis: Alcohol Oxidation and Olefin Epoxidation

    Unnikrishnan R Pillai, Endalkachew Sahle-Demessie , Vasudevan Namboodiri, Quiming Zhao, Juluis Enriquez
    U.S. EPA , 26 W. Martin Luther King Dr. , Cincinnati, OH 45268
    Phone: 513-569-773...

  14. Relationships between soybean shoot nitrogen components and soybean aphid populations

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Defining the relationships between soybean (Glycine max [L.] merr.) shoot nitrogen (N) components and soybean aphid (Aphis glycines Matsumura) populations will increase understanding of the biology of this important insect pest. In this 2-year field study, caged soybean plants were infested with so...

  15. Soybean (2010 JGI User Meeting)

    ScienceCinema

    Stacey, Gary

    2016-07-12

    Gary Stacey, associate director of the National Center for Soybean Biotechnology at the University of Missouri, gives a talk simply titled "Soybean" on March 24, 2010 at the 5th Annual DOE JGI User Meeting

  16. Soybean (2010 JGI User Meeting)

    SciTech Connect

    Stacey, Gary

    2010-03-24

    Gary Stacey, associate director of the National Center for Soybean Biotechnology at the University of Missouri, gives a talk simply titled "Soybean" on March 24, 2010 at the 5th Annual DOE JGI User Meeting

  17. Effect of epoxidation level on thermal properties and ionic conductivity of epoxidized natural rubber solid polymer nanocomposite electrolytes

    SciTech Connect

    Harun, Fatin; Chan, Chin Han; Winie, Tan; Sim, Lai Har; Zainal, Nurul Fatahah Asyqin

    2015-08-28

    Effect of epoxide content on the thermal and conductivity properties of epoxidized natural rubber (ENR) solid polymer nanocomposite electrolytes was investigated. Commercial available epoxidized natural rubber having 25 (ENR25) and 50 mole% (ENR50) epoxide, respectively were incorporated with lithium perchlorate (LiClO{sub 4}) salt and titanium dioxide (TiO{sub 2}) nanofiller via solution casting method. The solid polymer nanocomposite electrolytes were characterized by differential scanning calorimetry (DSC) and impedance spectroscopy (IS) for their thermal properties and conductivity, respectively. It was evident that introduction of LiClO{sub 4} causes a greater increase in glass transition temperature (T{sub g}) and ionic conductivity of ENR50 as compared to ENR25. Upon addition of TiO{sub 2} in ENR/LiClO{sub 4} system, a remarkable T{sub g} elevation was observed for both ENRs where ENR50 reveals a more pronounced changes. It is interesting to note that they exhibit different phenomenon in ionic conductivity with TiO{sub 2} loading where ENR25 shows enhancement of conductivity while ENR50 shows declination.

  18. Effect of epoxidation level on thermal properties and ionic conductivity of epoxidized natural rubber solid polymer nanocomposite electrolytes

    NASA Astrophysics Data System (ADS)

    Harun, Fatin; Chan, Chin Han; Sim, Lai Har; Winie, Tan; Zainal, Nurul Fatahah Asyqin

    2015-08-01

    Effect of epoxide content on the thermal and conductivity properties of epoxidized natural rubber (ENR) solid polymer nanocomposite electrolytes was investigated. Commercial available epoxidized natural rubber having 25 (ENR25) and 50 mole% (ENR50) epoxide, respectively were incorporated with lithium perchlorate (LiClO4) salt and titanium dioxide (TiO2) nanofiller via solution casting method. The solid polymer nanocomposite electrolytes were characterized by differential scanning calorimetry (DSC) and impedance spectroscopy (IS) for their thermal properties and conductivity, respectively. It was evident that introduction of LiClO4 causes a greater increase in glass transition temperature (Tg) and ionic conductivity of ENR50 as compared to ENR25. Upon addition of TiO2 in ENR/LiClO4 system, a remarkable Tg elevation was observed for both ENRs where ENR50 reveals a more pronounced changes. It is interesting to note that they exhibit different phenomenon in ionic conductivity with TiO2 loading where ENR25 shows enhancement of conductivity while ENR50 shows declination.

  19. Modeling Epoxidation of Drug-like Molecules with a Deep Machine Learning Network.

    PubMed

    Hughes, Tyler B; Miller, Grover P; Swamidass, S Joshua

    2015-07-22

    Drug toxicity is frequently caused by electrophilic reactive metabolites that covalently bind to proteins. Epoxides comprise a large class of three-membered cyclic ethers. These molecules are electrophilic and typically highly reactive due to ring tension and polarized carbon-oxygen bonds. Epoxides are metabolites often formed by cytochromes P450 acting on aromatic or double bonds. The specific location on a molecule that undergoes epoxidation is its site of epoxidation (SOE). Identifying a molecule's SOE can aid in interpreting adverse events related to reactive metabolites and direct modification to prevent epoxidation for safer drugs. This study utilized a database of 702 epoxidation reactions to build a model that accurately predicted sites of epoxidation. The foundation for this model was an algorithm originally designed to model sites of cytochromes P450 metabolism (called XenoSite) that was recently applied to model the intrinsic reactivity of diverse molecules with glutathione. This modeling algorithm systematically and quantitatively summarizes the knowledge from hundreds of epoxidation reactions with a deep convolution network. This network makes predictions at both an atom and molecule level. The final epoxidation model constructed with this approach identified SOEs with 94.9% area under the curve (AUC) performance and separated epoxidized and non-epoxidized molecules with 79.3% AUC. Moreover, within epoxidized molecules, the model separated aromatic or double bond SOEs from all other aromatic or double bonds with AUCs of 92.5% and 95.1%, respectively. Finally, the model separated SOEs from sites of sp(2) hydroxylation with 83.2% AUC. Our model is the first of its kind and may be useful for the development of safer drugs. The epoxidation model is available at http://swami.wustl.edu/xenosite. PMID:27162970

  20. Modeling Epoxidation of Drug-like Molecules with a Deep Machine Learning Network

    PubMed Central

    2015-01-01

    Drug toxicity is frequently caused by electrophilic reactive metabolites that covalently bind to proteins. Epoxides comprise a large class of three-membered cyclic ethers. These molecules are electrophilic and typically highly reactive due to ring tension and polarized carbon–oxygen bonds. Epoxides are metabolites often formed by cytochromes P450 acting on aromatic or double bonds. The specific location on a molecule that undergoes epoxidation is its site of epoxidation (SOE). Identifying a molecule’s SOE can aid in interpreting adverse events related to reactive metabolites and direct modification to prevent epoxidation for safer drugs. This study utilized a database of 702 epoxidation reactions to build a model that accurately predicted sites of epoxidation. The foundation for this model was an algorithm originally designed to model sites of cytochromes P450 metabolism (called XenoSite) that was recently applied to model the intrinsic reactivity of diverse molecules with glutathione. This modeling algorithm systematically and quantitatively summarizes the knowledge from hundreds of epoxidation reactions with a deep convolution network. This network makes predictions at both an atom and molecule level. The final epoxidation model constructed with this approach identified SOEs with 94.9% area under the curve (AUC) performance and separated epoxidized and non-epoxidized molecules with 79.3% AUC. Moreover, within epoxidized molecules, the model separated aromatic or double bond SOEs from all other aromatic or double bonds with AUCs of 92.5% and 95.1%, respectively. Finally, the model separated SOEs from sites of sp2 hydroxylation with 83.2% AUC. Our model is the first of its kind and may be useful for the development of safer drugs. The epoxidation model is available at http://swami.wustl.edu/xenosite. PMID:27162970

  1. Allergic contact dermatitis to acrylates in disposable blue diathermy pads.

    PubMed Central

    Sidhu, S. K.; Shaw, S.

    1999-01-01

    We report 2 cases of elicitation of allergic contact dermatitis to acrylates from disposable blue diathermy pads used on patients who underwent routine surgery. Their reactions were severe, and took approximately 5 weeks to resolve. Both patients gave a prior history of finger tip dermatitis following the use of artificial sculptured acrylic nails, which is a common, but poorly reported, cause of acrylate allergy. Patch testing subsequently confirmed allergies to multiple acrylates present in both the conducting gel of disposable blue diathermy pads, and artificial sculptured acrylic nails. We advocate careful history taking prior to surgery to avoid unnecessary exposure to acrylates in patients already sensitized. Images Figure 1 Figure 2 PMID:10364952

  2. Synthesis and self-assembly behavior of a biodegradable and sustainable soybean oil-based copolymer nanomicelle

    NASA Astrophysics Data System (ADS)

    Bao, Lixia; Bian, Longchun; Zhao, Mimi; Lei, Jingxin; Wang, Jiliang

    2014-08-01

    Herein, we report a novel amphiphilic biodegradable and sustainable soybean oil-based copolymer (SBC) prepared by grafting hydrophilic and biocompatible hydroxyethyl acrylate (HEA) polymeric segments onto the natural hydrophobic soybean oil chains. FTIR, H1-NMR, and GPC measurements have been used to investigate the molecular structure of the obtained SBC macromolecules. Self-assembly behaviors of the prepared SBC in aqueous solution have also been extensively evaluated by fluorescence spectroscopy and transmission electron microscopy. The prepared SBC nanocarrier with the size range of 40 to 80 nm has a potential application in the biomedical field.

  3. The conformations of cyclooctene: consequences for epoxidation chemistry.

    PubMed

    Neuenschwander, Ulrich; Hermans, Ive

    2011-12-16

    The conformational space of cyclooctene has been explored computationally in order to rationalize its high epoxidation selectivity. Four different conformations were identified. Each conformation is chiral and has two enantiomeric forms. The degeneracy is further increased by a ring-inversion process, yielding a total of 16 conformers. The potential energy surface for the interconversion of these conformers was characterized via intrinsic reaction coordinate analyses. Furthermore, an evaluation of the microcanonical partition functions allowed for a quantification of the entropy contributions and hence the calculation of the equilibrium composition at different temperatures. The results strongly suggest that the high epoxidation selectivity, typically observed for cyclooctene, is related to a poor σ(C-αH)-π(C═C) orbital overlap in the predominant conformation, disfavoring αH-abstraction by radical species and thus allylic byproduct formation via undesired homolytic side-reactions.

  4. Sunflowers versus soybeans

    SciTech Connect

    Baldwin, J.D.C.

    1980-10-01

    While both soybeans and sunflowers provide oil and protein, sunflowers offer the higher potential yield of oil per hectare. Research to modify vegetable oils to improve their fuel properties is suggested, particularly on improving the characteristics of the oil as a fuel for diesel engines.

  5. 21 CFR 173.5 - Acrylate-acrylamide resins.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... additive consists of one of the following: (1) Acrylamide-acrylic acid resin (hydrolyzed polyacrylamide) is... and acrylic acid, with the greater part of the polymer being composed of acrylamide units. (2)...

  6. Markedly Elevated Carbamazepine-10,11-epoxide/Carbamazepine Ratio in a Fatal Carbamazepine Ingestion

    PubMed Central

    Russell, Jason L.; Spiller, Henry A.; Baker, Daniel D.

    2015-01-01

    Carbamazepine is a widely used anticonvulsant. Its metabolite, carbamazepine-10,11-epoxide, has been found to display similar anticonvulsant and neurotoxic properties. While the ratio of parent to metabolite concentration varies significantly, at therapeutic doses the epoxide concentration is generally about 20% of the parent. We report a case of fatal carbamazepine overdose in which the epoxide metabolite concentration was found to be 450% higher than the parent compound, suggesting a potential role for metabolite quantification in severe toxicity. PMID:26550016

  7. Direct Epoxidation of Propylene over Stabilized Cu+ Surface Sites on Ti Modified Cu2O

    DOE PAGES

    Yang, X.; Kattel, S.; Xiong, K.; Mudiyanselage, K.; Rykov, S.; Senanayake, S. D.; Rodriguez, J. A.; Liu, P.; Stacchiola, D. J.; Chen, J. G.

    2015-07-17

    Direct propylene epoxidation by O2 is a challenging reaction because of the strong tendency for complete combustion. Results from the current study demonstrate the feasibility to tune the epoxidation selectivity by generating highly dispersed and stabilized Cu+ active sites in a TiCuOx mixed oxide. The TiCuOx surface anchors the key surface intermediate, oxametallacycle, leading to higher selectivity for epoxidation of propylene.

  8. Isolation and characterization of Xenopus soluble epoxide hydrolase.

    PubMed

    Purba, Endang R; Oguro, Ami; Imaoka, Susumu

    2014-07-01

    Soluble epoxide hydrolase (sEH) contributes to cell growth, but the contribution of sEH to embryonic development is not well understood. In this study, Xenopus sEH cDNA was isolated from embryos of Xenopus laevis. The Xenopus sEH was expressed in Escherichia coli and was purified. The epoxide hydrolase and phosphatase activities of purified sEH were investigated. The Xenopus sEH did not show phosphatase activity toward 4-methylumbelliferyl phosphate or several lysophosphatidic acids although it had EH activity. The amino acid sequence of Xenopus sEH was compared with that reported previously. We found amino acid substitutions of the 29th Thr to Asn and the 146th Arg to His and prepared a sEH mutant (N29T/H146R), designed as mutant 1. Neither wild-type sEH nor mutant 1 had phosphatase activity. Additional substitution of the 11th Gly with Asp was found by comparison with human sEH which has phosphatase activity, but the Xenopus sEH mutant G11D prepared as mutant 2 did not have phosphatase activity. The epoxide hydrolase activity of sEH seemed to be similar to that of human sEH, while Xenopus sEH did not have phosphatase activity toward several substrates that human sEH metabolizes. PMID:24681163

  9. Transgenic soybeans and soybean protein analysis: an overview.

    PubMed

    Natarajan, Savithiry; Luthria, Devanand; Bae, Hanhong; Lakshman, Dilip; Mitra, Amitava

    2013-12-01

    To meet the increasing global demand for soybeans for food and feed consumption, new high-yield varieties with improved quality traits are needed. To ensure the safety of the crop, it is important to determine the variation in seed proteins along with unintended changes that may occur in the crop as a result various stress stimuli, breeding, and genetic modification. Understanding the variation of seed proteins in the wild and cultivated soybean cultivars is useful for determining unintended protein expression in new varieties of soybeans. Proteomic technology is useful to analyze protein variation due to various stimuli. This short review discusses transgenic soybeans, different soybean proteins, and the approaches used for protein analysis. The characterization of soybean protein will be useful for researchers, nutrition professionals, and regulatory agencies dealing with soy-derived food products.

  10. 40 CFR 721.324 - Alkoxylated acrylate polymer (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkoxylated acrylate polymer (generic... Substances § 721.324 Alkoxylated acrylate polymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as alkoxylated acrylate...

  11. 40 CFR 721.324 - Alkoxylated acrylate polymer (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkoxylated acrylate polymer (generic... Substances § 721.324 Alkoxylated acrylate polymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as alkoxylated acrylate...

  12. 40 CFR 721.324 - Alkoxylated acrylate polymer (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkoxylated acrylate polymer (generic... Substances § 721.324 Alkoxylated acrylate polymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as alkoxylated acrylate...

  13. 40 CFR 721.5325 - Nickel acrylate complex.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Nickel acrylate complex. 721.5325... Substances § 721.5325 Nickel acrylate complex. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance nickel acrylate complex (PMN P-85-1034) is subject to reporting...

  14. 40 CFR 721.5325 - Nickel acrylate complex.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Nickel acrylate complex. 721.5325... Substances § 721.5325 Nickel acrylate complex. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance nickel acrylate complex (PMN P-85-1034) is subject to reporting...

  15. 40 CFR 721.5325 - Nickel acrylate complex.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Nickel acrylate complex. 721.5325... Substances § 721.5325 Nickel acrylate complex. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance nickel acrylate complex (PMN P-85-1034) is subject to reporting...

  16. 40 CFR 721.5325 - Nickel acrylate complex.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Nickel acrylate complex. 721.5325... Substances § 721.5325 Nickel acrylate complex. Link to an amendment published at 79 FR 34637, June 18, 2014... nickel acrylate complex (PMN P-85-1034) is subject to reporting under this section for the...

  17. 40 CFR 721.5325 - Nickel acrylate complex.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Nickel acrylate complex. 721.5325... Substances § 721.5325 Nickel acrylate complex. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance nickel acrylate complex (PMN P-85-1034) is subject to reporting...

  18. 21 CFR 573.120 - Acrylamide-acrylic acid resin.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Acrylamide-acrylic acid resin. 573.120 Section 573.120 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Food Additive Listing § 573.120 Acrylamide-acrylic acid resin. Acrylamide-acrylic acid...

  19. 21 CFR 173.5 - Acrylate-acrylamide resins.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Acrylate-acrylamide resins. 173.5 Section 173.5... CONSUMPTION Polymer Substances and Polymer Adjuvants for Food Treatment § 173.5 Acrylate-acrylamide resins. Acrylate-acrylamide resins may be safely used in food under the following prescribed conditions: (a)...

  20. 21 CFR 176.110 - Acrylamide-acrylic acid resins.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Acrylamide-acrylic acid resins. 176.110 Section 176... Substances for Use Only as Components of Paper and Paperboard § 176.110 Acrylamide-acrylic acid resins. Acrylamide-acrylic acid resins may be safely used as components of articles intended for use in...

  1. 21 CFR 176.110 - Acrylamide-acrylic acid resins.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Acrylamide-acrylic acid resins. 176.110 Section... Substances for Use Only as Components of Paper and Paperboard § 176.110 Acrylamide-acrylic acid resins. Acrylamide-acrylic acid resins may be safely used as components of articles intended for use in...

  2. 21 CFR 177.1310 - Ethylene-acrylic acid copolymers.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Ethylene-acrylic acid copolymers. 177.1310 Section... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1310 Ethylene-acrylic acid copolymers. The ethylene-acrylic acid copolymers identified in paragraph (a) of this section may be...

  3. 21 CFR 177.1310 - Ethylene-acrylic acid copolymers.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Ethylene-acrylic acid copolymers. 177.1310 Section... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1310 Ethylene-acrylic acid copolymers. The ethylene-acrylic acid copolymers identified in paragraph (a) of this section may be...

  4. 21 CFR 176.110 - Acrylamide-acrylic acid resins.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Acrylamide-acrylic acid resins. 176.110 Section... Substances for Use Only as Components of Paper and Paperboard § 176.110 Acrylamide-acrylic acid resins. Acrylamide-acrylic acid resins may be safely used as components of articles intended for use in...

  5. 21 CFR 177.1310 - Ethylene-acrylic acid copolymers.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Ethylene-acrylic acid copolymers. 177.1310 Section... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1310 Ethylene-acrylic acid copolymers. The ethylene-acrylic acid copolymers identified in paragraph (a) of this section may be...

  6. 40 CFR 721.10537 - Acrylate ester (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acrylate ester (generic). 721.10537... Substances § 721.10537 Acrylate ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as acrylate ester (PMN P-01-579) is subject...

  7. 40 CFR 721.10477 - Acrylate ester (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acrylate ester (generic). 721.10477... Substances § 721.10477 Acrylate ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as acrylate ester (PMN P-04-290) is subject...

  8. 40 CFR 721.10477 - Acrylate ester (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acrylate ester (generic). 721.10477... Substances § 721.10477 Acrylate ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as acrylate ester (PMN P-04-290) is subject...

  9. 40 CFR 721.10537 - Acrylate ester (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acrylate ester (generic). 721.10537... Substances § 721.10537 Acrylate ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as acrylate ester (PMN P-01-579) is subject...

  10. 21 CFR 177.1320 - Ethylene-ethyl acrylate copolymers.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... prescribed for polyethylene in § 177.1520. (1) Specifications—(i) Infrared identification. Ethylene-ethyl acrylate copolymers can be identified by their characteristic infrared spectra. (ii) Quantitative determination of ethyl acrylate content. The ethyl acrylate can be determined by the infrared spectra. Prepare...

  11. 21 CFR 177.1320 - Ethylene-ethyl acrylate copolymers.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... prescribed for polyethylene in § 177.1520. (1) Specifications—(i) Infrared identification. Ethylene-ethyl acrylate copolymers can be identified by their characteristic infrared spectra. (ii) Quantitative determination of ethyl acrylate content. The ethyl acrylate can be determined by the infrared spectra. Prepare...

  12. 40 CFR 721.324 - Alkoxylated acrylate polymer (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkoxylated acrylate polymer (generic... Substances § 721.324 Alkoxylated acrylate polymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as alkoxylated acrylate...

  13. 40 CFR 721.324 - Alkoxylated acrylate polymer (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkoxylated acrylate polymer (generic... Substances § 721.324 Alkoxylated acrylate polymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as alkoxylated acrylate...

  14. 40 CFR 721.484 - Fluorinated acrylic copolymer (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Fluorinated acrylic copolymer (generic... Specific Chemical Substances § 721.484 Fluorinated acrylic copolymer (generic name). (a) Chemical substance... fluorinated acrylic copolymer (PMN P-95-1208) is subject to reporting under this section for the...

  15. 40 CFR 721.484 - Fluorinated acrylic copolymer (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fluorinated acrylic copolymer (generic... Specific Chemical Substances § 721.484 Fluorinated acrylic copolymer (generic name). (a) Chemical substance... fluorinated acrylic copolymer (PMN P-95-1208) is subject to reporting under this section for the...

  16. 40 CFR 721.10180 - Trifunctional acrylic ester (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Trifunctional acrylic ester (generic... Specific Chemical Substances § 721.10180 Trifunctional acrylic ester (generic). (a) Chemical substance and... acrylic ester (PMN P-04-692) is subject to reporting under this section for the significant new...

  17. 40 CFR 721.10180 - Trifunctional acrylic ester (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Trifunctional acrylic ester (generic... Specific Chemical Substances § 721.10180 Trifunctional acrylic ester (generic). (a) Chemical substance and... acrylic ester (PMN P-04-692) is subject to reporting under this section for the significant new...

  18. 21 CFR 177.1060 - n-Alkylglutarimide/acrylic copolymers.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false n-Alkylglutarimide/acrylic copolymers. 177.1060... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1060 n-Alkylglutarimide/acrylic copolymers. n-Alkylglutarimide/acrylic copolymers identified in this section may be safely used as...

  19. 40 CFR 721.10180 - Trifunctional acrylic ester (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Trifunctional acrylic ester (generic... Specific Chemical Substances § 721.10180 Trifunctional acrylic ester (generic). (a) Chemical substance and... acrylic ester (PMN P-04-692) is subject to reporting under this section for the significant new...

  20. 40 CFR 721.484 - Fluorinated acrylic copolymer (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Fluorinated acrylic copolymer (generic... Specific Chemical Substances § 721.484 Fluorinated acrylic copolymer (generic name). (a) Chemical substance... fluorinated acrylic copolymer (PMN P-95-1208) is subject to reporting under this section for the...

  1. 40 CFR 721.484 - Fluorinated acrylic copolymer (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Fluorinated acrylic copolymer (generic... Specific Chemical Substances § 721.484 Fluorinated acrylic copolymer (generic name). (a) Chemical substance... fluorinated acrylic copolymer (PMN P-95-1208) is subject to reporting under this section for the...

  2. 21 CFR 177.1060 - n-Alkylglutarimide/acrylic copolymers.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true n-Alkylglutarimide/acrylic copolymers. 177.1060... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1060 n-Alkylglutarimide/acrylic copolymers. n-Alkylglutarimide/acrylic copolymers identified in this section may be safely used as...

  3. 21 CFR 177.1060 - n-Alkylglutarimide/acrylic copolymers.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false n-Alkylglutarimide/acrylic copolymers. 177.1060... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1060 n-Alkylglutarimide/acrylic copolymers. n-Alkylglutarimide/acrylic copolymers identified in this section may be safely used as...

  4. 40 CFR 721.10180 - Trifunctional acrylic ester (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Trifunctional acrylic ester (generic... Specific Chemical Substances § 721.10180 Trifunctional acrylic ester (generic). (a) Chemical substance and... acrylic ester (PMN P-04-692) is subject to reporting under this section for the significant new...

  5. 21 CFR 177.1310 - Ethylene-acrylic acid copolymers.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Ethylene-acrylic acid copolymers. 177.1310 Section... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1310 Ethylene-acrylic acid copolymers. The ethylene-acrylic acid copolymers identified in paragraph (a) of this section may be...

  6. 21 CFR 176.110 - Acrylamide-acrylic acid resins.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Acrylamide-acrylic acid resins. 176.110 Section... Substances for Use Only as Components of Paper and Paperboard § 176.110 Acrylamide-acrylic acid resins. Acrylamide-acrylic acid resins may be safely used as components of articles intended for use in...

  7. 40 CFR 721.484 - Fluorinated acrylic copolymer (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fluorinated acrylic copolymer (generic... Specific Chemical Substances § 721.484 Fluorinated acrylic copolymer (generic name). (a) Chemical substance... fluorinated acrylic copolymer (PMN P-95-1208) is subject to reporting under this section for the...

  8. 40 CFR 721.10180 - Trifunctional acrylic ester (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Trifunctional acrylic ester (generic... Specific Chemical Substances § 721.10180 Trifunctional acrylic ester (generic). (a) Chemical substance and... acrylic ester (PMN P-04-692) is subject to reporting under this section for the significant new...

  9. 21 CFR 177.1060 - n-Alkylglutarimide/acrylic copolymers.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false n-Alkylglutarimide/acrylic copolymers. 177.1060... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1060 n-Alkylglutarimide/acrylic copolymers. n-Alkylglutarimide/acrylic copolymers identified in this section may be safely used as...

  10. 40 CFR 721.10307 - Acrylate resin (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acrylate resin (generic). 721.10307... Substances § 721.10307 Acrylate resin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as acrylate resin (PMN P-01-343) is subject...

  11. 40 CFR 721.10307 - Acrylate resin (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Acrylate resin (generic). 721.10307... Substances § 721.10307 Acrylate resin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as acrylate resin (PMN P-01-343) is subject...

  12. 21 CFR 173.5 - Acrylate-acrylamide resins.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Acrylate-acrylamide resins. 173.5 Section 173.5... CONSUMPTION Polymer Substances and Polymer Adjuvants for Food Treatment § 173.5 Acrylate-acrylamide resins. Acrylate-acrylamide resins may be safely used in food under the following prescribed conditions: (a)...

  13. Molecular Soybean-Pathogen Interactions.

    PubMed

    Whitham, Steven A; Qi, Mingsheng; Innes, Roger W; Ma, Wenbo; Lopes-Caitar, Valéria; Hewezi, Tarek

    2016-08-01

    Soybean hosts a wide variety of pathogens that cause significant yield losses. The importance of soybean as a major oilseed crop has led to research focused on its interactions with pathogens, such as Soybean mosaic virus, Pseudomonas syringae, Phytophthora sojae, Phakopsora pachyrhizi, and Heterodera glycines. Pioneering work on soybean's interactions with these organisms, which represent the five major pathogen groups (viruses, bacteria, oomycetes, fungi, and nematodes), has contributed to our understanding of the molecular mechanisms underlying virulence and immunity. These mechanisms involve conserved and unique features that validate the need for research in both soybean and homologous model systems. In this review, we discuss identification of effectors and their functions as well as resistance gene-mediated recognition and signaling. We also point out areas in which model systems and recent advances in resources and tools have provided opportunities to gain deeper insights into soybean-pathogen interactions. PMID:27359370

  14. Acrylic Tanks for Stunning Chemical Demonstrations

    ERIC Educational Resources Information Center

    Mirholm, Alexander; Ellervik, Ulf

    2009-01-01

    We describe the use of acrylic tanks (400 x 450 x 27 mm) for visualization of chemical demonstrations in aqueous solutions. Examples of well-suited demonstrations are oscillating reactions, pH indicators, photochemical reduction of Lauth's violet, and chemoluminiscent reactions. (Contains 1 figure.)

  15. 40 CFR 721.405 - Polyether acrylate.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 721.405 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.405 Polyether acrylate. (a) Chemical substance and significant new uses subject to reporting....

  16. 40 CFR 721.405 - Polyether acrylate.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 721.405 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.405 Polyether acrylate. (a) Chemical substance and significant new uses subject to reporting....

  17. Fighting Asian Soybean Rust

    PubMed Central

    Langenbach, Caspar; Campe, Ruth; Beyer, Sebastian F.; Mueller, André N.; Conrath, Uwe

    2016-01-01

    Phakopsora pachyrhizi is a biotrophic fungus provoking SBR disease. SBR poses a major threat to global soybean production. Though several R genes provided soybean immunity to certain P. pachyrhizi races, the pathogen swiftly overcame this resistance. Therefore, fungicides are the only current means to control SBR. However, insensitivity to fungicides is soaring in P. pachyrhizi and, therefore, alternative measures are needed for SBR control. In this article, we discuss the different approaches for fighting SBR and their potential, disadvantages, and advantages over other measures. These encompass conventional breeding for SBR resistance, transgenic approaches, exploitation of transcription factors, secondary metabolites, and antimicrobial peptides, RNAi/HIGS, and biocontrol strategies. It seems that an integrating approach exploiting different measures is likely to provide the best possible means for the effective control of SBR. PMID:27375652

  18. Fighting Asian Soybean Rust.

    PubMed

    Langenbach, Caspar; Campe, Ruth; Beyer, Sebastian F; Mueller, André N; Conrath, Uwe

    2016-01-01

    Phakopsora pachyrhizi is a biotrophic fungus provoking SBR disease. SBR poses a major threat to global soybean production. Though several R genes provided soybean immunity to certain P. pachyrhizi races, the pathogen swiftly overcame this resistance. Therefore, fungicides are the only current means to control SBR. However, insensitivity to fungicides is soaring in P. pachyrhizi and, therefore, alternative measures are needed for SBR control. In this article, we discuss the different approaches for fighting SBR and their potential, disadvantages, and advantages over other measures. These encompass conventional breeding for SBR resistance, transgenic approaches, exploitation of transcription factors, secondary metabolites, and antimicrobial peptides, RNAi/HIGS, and biocontrol strategies. It seems that an integrating approach exploiting different measures is likely to provide the best possible means for the effective control of SBR. PMID:27375652

  19. Soybean Growth Aboard ISS

    NASA Technical Reports Server (NTRS)

    2002-01-01

    This is a photo of soybeans growing in the Advanced Astroculture (ADVASC) Experiment aboard the International Space Station (ISS). The ADVASC experiment was one of the several new experiments and science facilities delivered to the ISS by Expedition Five aboard the Space Shuttle Orbiter Endeavor STS-111 mission. An agricultural seed company will grow soybeans in the ADVASC hardware to determine whether soybean plants can produce seeds in a microgravity environment. Secondary objectives include determination of the chemical characteristics of the seed in space and any microgravity impact on the plant growth cycle. Station science will also be conducted by the ever-present ground crew, with a new cadre of controllers for Expedition Five in the ISS Payload Operations Control Center (POCC) at NASA's Marshall Space Flight Center in Huntsville, Alabama. Controllers work in three shifts around the clock, 7 days a week, in the POCC, the world's primary science command post for the Space Station. The POCC links Earth-bound researchers around the world with their experiments and crew aboard the Space Station.

  20. Large Acrylic Spherical Windows In Hyperbaric Underwater Photography

    NASA Astrophysics Data System (ADS)

    Lones, Joe J.; Stachiw, Jerry D.

    1983-10-01

    Both acrylic plastic and glass are common materials for hyperbaric optical windows. Although glass continues to be used occasionally for small windows, virtually all large viewports are made of acrylic. It is easy to uderstand the wide use of acrylic when comparing design properties of this plastic with those of glass, and glass windows are relatively more difficult to fabricate and use. in addition there are published guides for the design and fabrication of acrylic windows to be used in the hyperbaric environment of hydrospace. Although these procedures for fabricating the acrylic windows are somewhat involved, the results are extremely reliable. Acrylic viewports are now fabricated to very large sizes for manned observation or optical quality instrumen tation as illustrated by the numerous acrylic submersible vehicle hulls for hu, an occupancy currently in operation and a 3600 large optical window recently developed for the Walt Disney Circle Vision under-water camera housing.

  1. Asymmetric Epoxidation: A Twinned Laboratory and Molecular Modeling Experiment for Upper-Level Organic Chemistry Students

    ERIC Educational Resources Information Center

    Hii, King Kuok; Rzepa, Henry S.; Smith, Edward H.

    2015-01-01

    The coupling of a student experiment involving the preparation and use of a catalyst for the asymmetric epoxidation of an alkene with computational simulations of various properties of the resulting epoxide is set out in the form of a software toolbox from which students select appropriate components. At the core of these are the computational…

  2. Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions.

    PubMed

    Novacek, Johanna; Roiser, Lukas; Zielke, Katharina; Robiette, Raphaël; Waser, Mario

    2016-08-01

    The key factors for carbonyl-stabilised ammonium ylide-mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine-based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions. PMID:27381752

  3. 40 CFR 721.7210 - Epoxidized copolymer of phenol and substituted phenol.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Epoxidized copolymer of phenol and substituted phenol. 721.7210 Section 721.7210 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7210 Epoxidized copolymer of phenol and substituted phenol. (a)...

  4. 40 CFR 721.7210 - Epoxidized copolymer of phenol and substituted phenol.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Epoxidized copolymer of phenol and substituted phenol. 721.7210 Section 721.7210 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7210 Epoxidized copolymer of phenol and substituted phenol. (a)...

  5. Fluorinated Alcohols as Activators for the Solvent-Free Chemical Fixation of Carbon Dioxide into Epoxides.

    PubMed

    Gennen, Sandro; Alves, Margot; Méreau, Raphaël; Tassaing, Thierry; Gilbert, Bernard; Detrembleur, Christophe; Jerome, Christine; Grignard, Bruno

    2015-06-01

    The addition of fluorinated alcohols to onium salts provides highly efficient organocatalysts for the chemical fixation of CO2 into epoxides under mild experimental conditions. The combination of online kinetic studies, NMR titrations and DFT calculations allows understanding this synergistic effect that provides an active organocatalyst for CO2 /epoxides coupling.

  6. Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions.

    PubMed

    Novacek, Johanna; Roiser, Lukas; Zielke, Katharina; Robiette, Raphaël; Waser, Mario

    2016-08-01

    The key factors for carbonyl-stabilised ammonium ylide-mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine-based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions.

  7. 40 CFR 721.7210 - Epoxidized copolymer of phenol and substituted phenol.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Epoxidized copolymer of phenol and substituted phenol. 721.7210 Section 721.7210 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7210 Epoxidized copolymer of phenol and substituted phenol. (a)...

  8. 40 CFR 721.7210 - Epoxidized copolymer of phenol and substituted phenol.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Epoxidized copolymer of phenol and substituted phenol. 721.7210 Section 721.7210 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7210 Epoxidized copolymer of phenol and substituted phenol. (a)...

  9. 40 CFR 721.7210 - Epoxidized copolymer of phenol and substituted phenol.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Epoxidized copolymer of phenol and substituted phenol. 721.7210 Section 721.7210 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.7210 Epoxidized copolymer of phenol and substituted phenol. (a)...

  10. COMPARATIVE STUDIES OF THE EFFECT OF POLYCYCLIC AROMATIC HYDROCARBON GEOMETRY ON THE HYDROLYSIS OF DIOL EPOXIDES

    EPA Science Inventory

    Comparative studies of the effect of polycyclic aromatic hydrocarbon geometry on the hydrolysis of diol epoxides

    The interaction of the diol epoxides (DEs) of both planar and non-planar PAHs with water have been examined using quantum mechanical and molecular dynamics. Th...

  11. Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions

    PubMed Central

    Robiette, Raphaël; Waser, Mario

    2016-01-01

    The key factors for carbonyl-stabilised ammonium ylide-mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine-based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions. PMID:27381752

  12. Soybean Aphid (Hemiptera: Aphididae) Affects Soybean Spectral Reflectance.

    PubMed

    Alves, Tavvs M; Macrae, Ian V; Koch, Robert L

    2015-12-01

    Soybean aphid, Aphis glycines Matsumura (Hemiptera: Aphididae), is the most economically important insect pest of soybean in the north central United States. Scouting-based integrated pest management (IPM) programs could become more efficient and more widely adopted by using plant spectral reflectance to estimate soybean aphid injury. Our objective was to determine whether plant spectral reflectance is affected by soybean aphid feeding. Field trials were conducted in 2013 and 2014 using caged plots. Early-, late-, and noninfested treatments were established to create a gradient of soybean aphid pressure. Whole-plant soybean aphid densities were recorded weekly. Measurements of plant spectral reflectance occurred on two sample dates per year. Simple linear regression models were used to test the effect of cumulative aphid-days (CAD) on plant spectral reflectance at 680 nm (RED) and 800 nm (NIR), normalized difference vegetation index (NDVI), and relative chlorophyll content. Data indicated that CAD had no effect on canopy-level RED reflectance, but CAD decreased canopy-level NIR reflectance and NDVI. Canopy- and leaf-level measurements typically indicated similar plant spectral response to increasing CAD. CAD generally had no effect on relative chlorophyll content. The present study provides the first documentation that remote sensing holds potential for detecting changes in plant spectral reflectance induced by soybean aphid. The use of plant spectral reflectance in soybean aphid management may assist future IPM programs to reduce sampling costs and prevent prophylactic insecticide sprays.

  13. Soybean Aphid (Hemiptera: Aphididae) Affects Soybean Spectral Reflectance

    PubMed Central

    Alves, Tavvs M.; Macrae, Ian V.; Koch, Robert L.

    2015-01-01

    Soybean aphid, Aphis glycines Matsumura (Hemiptera: Aphididae), is the most economically important insect pest of soybean in the north central United States. Scouting-based integrated pest management (IPM) programs could become more efficient and more widely adopted by using plant spectral reflectance to estimate soybean aphid injury. Our objective was to determine whether plant spectral reflectance is affected by soybean aphid feeding. Field trials were conducted in 2013 and 2014 using caged plots. Early-, late-, and noninfested treatments were established to create a gradient of soybean aphid pressure. Whole-plant soybean aphid densities were recorded weekly. Measurements of plant spectral reflectance occurred on two sample dates per year. Simple linear regression models were used to test the effect of cumulative aphid-days (CAD) on plant spectral reflectance at 680 nm (RED) and 800 nm (NIR), normalized difference vegetation index (NDVI), and relative chlorophyll content. Data indicated that CAD had no effect on canopy-level RED reflectance, but CAD decreased canopy-level NIR reflectance and NDVI. Canopy- and leaf-level measurements typically indicated similar plant spectral response to increasing CAD. CAD generally had no effect on relative chlorophyll content. The present study provides the first documentation that remote sensing holds potential for detecting changes in plant spectral reflectance induced by soybean aphid. The use of plant spectral reflectance in soybean aphid management may assist future IPM programs to reduce sampling costs and prevent prophylactic insecticide sprays. PMID:26470392

  14. General, Highly Selective Synthesis of 1,3- and 1,4-Difunctionalized Building Blocks by Regiodivergent Epoxide Opening.

    PubMed

    Funken, Nico; Mühlhaus, Felix; Gansäuer, Andreas

    2016-09-19

    We describe a regiodivergent epoxide opening (REO) featuring a catalyst-controlled synthesis of enantiomerically and diastereomerically highly enriched or pure syn- and anti- 1,3- and 1,4-difunctionalized building blocks from a common epoxide precursor. The REO is attractive for natural product synthesis and as a branching reaction for diversity-oriented synthesis with epoxides.

  15. General, Highly Selective Synthesis of 1,3- and 1,4-Difunctionalized Building Blocks by Regiodivergent Epoxide Opening.

    PubMed

    Funken, Nico; Mühlhaus, Felix; Gansäuer, Andreas

    2016-09-19

    We describe a regiodivergent epoxide opening (REO) featuring a catalyst-controlled synthesis of enantiomerically and diastereomerically highly enriched or pure syn- and anti- 1,3- and 1,4-difunctionalized building blocks from a common epoxide precursor. The REO is attractive for natural product synthesis and as a branching reaction for diversity-oriented synthesis with epoxides. PMID:27600090

  16. 40 CFR 63.1427 - Process vent requirements for processes using extended cookout as an epoxide emission reduction...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... constant, 1/hr. t = Time, hours. Note: This equation assumes a first order reaction with respect to epoxide... epoxide concentration using 40 CFR part 60, appendix A, Method 18. (ii) Determine the epoxide concentration in the vapor space using Raoult's Law or another appropriate phase equilibrium equation and...

  17. Retinoic acid 5,6-epoxidation by hemoproteins.

    PubMed

    Iwahashi, H; Ikeda, A; Negoro, Y; Kido, R

    1986-01-01

    Retinoic acid 5,6-epoxidase activity was found in several hemoproteins such as human oxy- and methemoglobin (HbO2 and MetHb), equine skeletal muscle oxy- and metmyoglobin (MbO2 and MetMb), bovine liver catalase, and horseradish peroxidase. Hematin also catalyzed retinoic acid 5,6-epoxidation. The results suggest that the heme moiety participates in the epoxidation. However, neither horse heart cytochrome c, nor free ferrous ion nor free ferric ion exhibited the epoxidase activity. Some hemoproteins (HbO2, MetHb, MbO2, MetMb, catalase, peroxidase, and hematin) exhibited characteristic individual pH dependences of the activity, suggesting that the epoxidase activities of the hemoproteins are influenced by the apoenzymes to some degree. This view is also supported by the finding that preincubation of an HbO2 preparation at various temperatures (37-70 degrees C) reduced its epoxidase activity with increasing temperature, whereas the activity of hematin was unaffected. Active oxygen scavengers such as mannitol, catalase, and superoxide dismutase exhibited no effect on the epoxidase activities of HbO2, MetHb, MbO2, and MetMb. A ligand of heme, CN- (100 mM), inhibited the epoxidase activities but N3- (100 mM) did not. The epoxidase activities were completely inhibited by NADPH, NADH, and/or 2-mercaptoethanol but not by NADP+ and/or NAD+. An intermediate in the epoxidation may be reduced by NADPH, NADH and/or 2-mercaptoethanol. Radical species can be considered as plausible candidates for the intermediate. PMID:3957898

  18. Biodegradation of heptachlor and heptachlor epoxide-contaminated soils by white-rot fungal inocula.

    PubMed

    Purnomo, Adi Setyo; Putra, Surya Rosa; Shimizu, Kuniyoshi; Kondo, Ryuichiro

    2014-10-01

    The ability of certain white-rot fungi (WRF) inocula to transform heptachlor and heptachlor epoxide and its application in artificially contaminated soil were investigated. Fungal inoculum of Pleurotus ostreatus eliminated approximately 89 % of heptachlor after 28 days of incubation, and chlordene was detected as the primary metabolite. The fungal inoculum of Pleurotus ostreatus had the highest ability to degrade heptachlor epoxide; approximately 32 % were degraded after 28 days of incubation, and heptachlor diol was detected as the metabolite product. Because Pleurotus ostreatus transformed heptachlor into a less toxic metabolite and could also effectively degrade heptachlor epoxide, it was then selected to be applied to artificially contaminated soil. The spent mushroom waste (SMW) of Pleurotus ostreatus degraded heptachlor and heptachlor epoxide by approximately 91 and 26 %, respectively, over 28 days. This finding indicated that Pleurotus ostreatus SMW could be used to bioremediate heptachlor- and heptachlor epoxide-contaminated environments.

  19. Photoaffinity labeling of opioid receptor with morphine-7,8-oxide (morphine epoxide)

    SciTech Connect

    Takayanagi, I.; Shibata, R.; Miyata, N.; Hirobe, M.

    1982-05-01

    The opioid receptor mediating inhibitory action of morphine in the electrically stimulated guinea pig ileum was irreversibly photoinactivated by morphine epoxide (3 X 10(-6) M). Morphine epoxide (up to 3 X 10(-5) M) did not influence the responses of rat vas deferens (epsilon-receptor) or rabbit vas deferens (kappa-receptor) to electrical stimulation. Effective concentrations of morphine epoxide were much lower in the guinea pig ileum (mu-receptor) than in the mouse vas deference (delta-receptor). The inhibitory action of (Met)-enkephalin on the twitch responses of the rat vas deferens and mouse vas deferens to electrical stimulation were not influenced after irradiation in the presence of morphine epoxide (3 X 10(-6) M). Therefore, morphine epoxide is probably a useful probe for photoaffinity labeling of the mu-receptor in vitro.

  20. Catalysts for CO2/epoxide ring-opening copolymerization

    PubMed Central

    Trott, G.; Saini, P. K.; Williams, C. K.

    2016-01-01

    This article summarizes and reviews recent progress in the development of catalysts for the ring-opening copolymerization of carbon dioxide and epoxides. The copolymerization is an interesting method to add value to carbon dioxide, including from waste sources, and to reduce pollution associated with commodity polymer manufacture. The selection of the catalyst is of critical importance to control the composition, properties and applications of the resultant polymers. This review highlights and exemplifies some key recent findings and hypotheses, in particular using examples drawn from our own research. PMID:26755758

  1. Brazil soybean yield covariance model

    NASA Technical Reports Server (NTRS)

    Callis, S. L.; Sakamoto, C.

    1984-01-01

    A model based on multiple regression was developed to estimate soybean yields for the seven soybean-growing states of Brazil. The meteorological data of these seven states were pooled and the years 1975 to 1980 were used to model since there was no technological trend in the yields during these years. Predictor variables were derived from monthly total precipitation and monthly average temperature.

  2. Intercalation of acrylic acid and sodium acrylate into kaolinite and their in situ polymerization

    NASA Astrophysics Data System (ADS)

    Zhang, Bo; Li, Yanfeng; Pan, Xiaobing; Jia, Xin; Wang, Xiaolong

    2007-02-01

    Novel nano-composites of poly (acrylic acid)-kaolinite were prepared, and intercalation and in situ polymerization were used in this process. The nano-composites were obtained by in situ polymerization of acrylic acid (AA) and sodium acrylate (AANa) intercalated into organo-kaolinite, which was obtained by refining and chemically modifying with solution intercalation step in order to increase the basal plane distance of the original clay. The modification was completed by using dimethyl-sulfoxide (DMSO)/methanol and potassium acetate (KAc)/water systems step by step. The materials were characterized with the help of XRD, FT-IR and TEM; the results confirmed that poly(acrylic acid) (PAA) and poly(sodium acrylate) (PAANa) were intercalated into the interlamellar spaces of kaolinite, the resulting copolymer composites (CC0 : copolymer crude kaolinite composite, CC1 : copolymer DMSO kaolinite composite, CC2 : copolymer KAc kaolinite composite) of CC2 exhibited a lamellar nano-composite with a mixed nano-morphology, and partial exfoliation of the intercalating clay platelets should be the main morphology. Finally, the effect of neutralization degree on the intercalation behavior was also investigated.

  3. Epoxide hydrolase of Trichoderma reesei: Biochemical properties and conformational characterization.

    PubMed

    de Oliveira, Gabriel Stephani; Adriani, Patricia Pereira; Borges, Flavia Garcia; Lopes, Adriana Rios; Campana, Patricia T; Chambergo, Felipe S

    2016-08-01

    Epoxide hydrolases (EHs) are enzymes that are present in all living organisms and catalyze the hydrolysis of epoxides to the corresponding vicinal diols. EHs have biotechnological potential in chiral chemistry. We report the cloning, purification, enzymatic activity, and conformational analysis of the TrEH gene from Trichoderma reesei strain QM9414 using circular dichroism spectroscopy. The EH gene has an open reading frame encoding a protein of 343 amino acid residues, resulting in a molecular mass of 38.2kDa. The enzyme presents an optimum pH of 7.2, and it is highly active at temperatures ranging from 23 to 50°C and thermally inactivated at 70°C (t1/2=7.4min). The Michaelis constants (Km) were 4.6mM for racemic substrate, 21.7mM for (R)-(+)-styrene oxide and 3.0mM for (S)-(-)-styrene oxide. The kcat/Km analysis indicated that TrEH is enantioselective and preferentially hydrolyzes (S)-(-)-styrene oxide. The conformational stability studies suggested that, despite the extreme conditions (high temperatures and extremely acid and basic pHs), TrEH is able to maintain a considerable part of its regular structures, including the preservation of the native cores in some cases. The recombinant protein showed enantioselectivity that was distinct from other fungus EHs, making this protein a potential biotechnological tool. PMID:27177457

  4. Peripheral FAAH and soluble epoxide hydrolase inhibitors are synergistically antinociceptive.

    PubMed

    Sasso, Oscar; Wagner, Karen; Morisseau, Christophe; Inceoglu, Bora; Hammock, Bruce D; Piomelli, Daniele

    2015-07-01

    We need better medicines to control acute and chronic pain. Fatty acid amide hydrolase (FAAH) and soluble epoxide hydrolase (sEH) catalyze the deactivating hydrolysis of two classes of bioactive lipid mediators--fatty acid ethanolamides (FAEs) and epoxidized fatty acids (EpFAs), respectively--which are biogenetically distinct but share the ability to attenuate pain responses and inflammation. In these experiments, we evaluated the antihyperalgesic activity of small-molecule inhibitors of FAAH and sEH, administered alone or in combination, in two pain models: carrageenan-induced hyperalgesia in mice and streptozocin-induced allodynia in rats. When administered separately, the sEH inhibitor 1-trifluoromethoxyphenyl-3-(1-propionylpiperidine-4-yl)urea (TPPU) and the peripherally restricted FAAH inhibitor URB937 were highly active in the two models. The combination TPPU plus URB937 was markedly synergistic, as assessed using isobolographic analyses. The results of these experiments reveal the existence of a possible functional crosstalk between FAEs and EpFAs in regulating pain responses. Additionally, the results suggest that combinations of sEH and FAAH inhibitors might be exploited therapeutically to achieve greater analgesic efficacy. PMID:25882247

  5. Integrated process and dual-function catalyst for olefin epoxidation

    DOEpatents

    Zhou, Bing; Rueter, Michael

    2003-01-01

    The invention discloses a dual-functional catalyst composition and an integrated process for production of olefin epoxides including propylene oxide by catalytic reaction of hydrogen peroxide from hydrogen and oxygen with olefin feeds such as propylene. The epoxides and hydrogen peroxide are preferably produced simultaneously in situ. The dual-functional catalyst comprises noble metal crystallites with dimensions on the nanometer scale (on the order of <1 nm to 10 nm), specially dispersed on titanium silicalite substrate particles. The dual functional catalyst catalyzes both the direct reaction of hydrogen and oxygen to generate hydrogen peroxide intermediate on the noble metal catalyst surface and the reaction of the hydrogen peroxide intermediate with the propylene feed to generate propylene oxide product. Combining both these functions in a single catalyst provides a very efficient integrated process operable below the flammability limits of hydrogen and highly selective for the production of hydrogen peroxide to produce olefin oxides such as propylene oxide without formation of undesired co-products.

  6. Soybean aphids making their summer appearance early

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Two small, soft-bodied insects have begun showing up in South Dakota soybean. One is the soybean aphid, and the other is a mealybug. Soybean aphids are yellow to yellow/green and are usually found feeding on the underside of leaves. Incidence of soybean aphid has been a bit higher than typical fo...

  7. 7 CFR 1220.614 - Soybeans.

    Code of Federal Regulations, 2013 CFR

    2013-01-01

    ... 7 Agriculture 10 2013-01-01 2013-01-01 false Soybeans. 1220.614 Section 1220.614 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Procedures To Request a Referendum Definitions § 1220.614 Soybeans. Soybeans means...

  8. 7 CFR 1220.127 - Soybean products.

    Code of Federal Regulations, 2013 CFR

    2013-01-01

    ... 7 Agriculture 10 2013-01-01 2013-01-01 false Soybean products. 1220.127 Section 1220.127... AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.127 Soybean products. The...

  9. 7 CFR 1220.614 - Soybeans.

    Code of Federal Regulations, 2014 CFR

    2014-01-01

    ... 7 Agriculture 10 2014-01-01 2014-01-01 false Soybeans. 1220.614 Section 1220.614 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Procedures To Request a Referendum Definitions § 1220.614 Soybeans. Soybeans means...

  10. 7 CFR 1220.128 - Soybeans.

    Code of Federal Regulations, 2013 CFR

    2013-01-01

    ... 7 Agriculture 10 2013-01-01 2013-01-01 false Soybeans. 1220.128 Section 1220.128 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.128 Soybeans. The...

  11. 7 CFR 1220.127 - Soybean products.

    Code of Federal Regulations, 2014 CFR

    2014-01-01

    ... 7 Agriculture 10 2014-01-01 2014-01-01 false Soybean products. 1220.127 Section 1220.127... AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.127 Soybean products. The...

  12. 7 CFR 1220.614 - Soybeans.

    Code of Federal Regulations, 2012 CFR

    2012-01-01

    ... 7 Agriculture 10 2012-01-01 2012-01-01 false Soybeans. 1220.614 Section 1220.614 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Procedures To Request a Referendum Definitions § 1220.614 Soybeans. Soybeans means...

  13. 7 CFR 1220.614 - Soybeans.

    Code of Federal Regulations, 2010 CFR

    2010-01-01

    ... 7 Agriculture 10 2010-01-01 2010-01-01 false Soybeans. 1220.614 Section 1220.614 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Procedures To Request a Referendum Definitions § 1220.614 Soybeans. Soybeans means...

  14. 7 CFR 1220.128 - Soybeans.

    Code of Federal Regulations, 2010 CFR

    2010-01-01

    ... 7 Agriculture 10 2010-01-01 2010-01-01 false Soybeans. 1220.128 Section 1220.128 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.128 Soybeans. The...

  15. 7 CFR 1220.127 - Soybean products.

    Code of Federal Regulations, 2012 CFR

    2012-01-01

    ... 7 Agriculture 10 2012-01-01 2012-01-01 false Soybean products. 1220.127 Section 1220.127... AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.127 Soybean products. The...

  16. 7 CFR 1220.127 - Soybean products.

    Code of Federal Regulations, 2011 CFR

    2011-01-01

    ... 7 Agriculture 10 2011-01-01 2011-01-01 false Soybean products. 1220.127 Section 1220.127... AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.127 Soybean products. The...

  17. 7 CFR 1220.128 - Soybeans.

    Code of Federal Regulations, 2012 CFR

    2012-01-01

    ... 7 Agriculture 10 2012-01-01 2012-01-01 false Soybeans. 1220.128 Section 1220.128 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.128 Soybeans. The...

  18. 7 CFR 1220.127 - Soybean products.

    Code of Federal Regulations, 2010 CFR

    2010-01-01

    ... 7 Agriculture 10 2010-01-01 2010-01-01 false Soybean products. 1220.127 Section 1220.127... AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.127 Soybean products. The...

  19. 7 CFR 1220.614 - Soybeans.

    Code of Federal Regulations, 2011 CFR

    2011-01-01

    ... 7 Agriculture 10 2011-01-01 2011-01-01 false Soybeans. 1220.614 Section 1220.614 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Procedures To Request a Referendum Definitions § 1220.614 Soybeans. Soybeans means...

  20. 7 CFR 1220.128 - Soybeans.

    Code of Federal Regulations, 2014 CFR

    2014-01-01

    ... 7 Agriculture 10 2014-01-01 2014-01-01 false Soybeans. 1220.128 Section 1220.128 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.128 Soybeans. The...

  1. 7 CFR 1220.128 - Soybeans.

    Code of Federal Regulations, 2011 CFR

    2011-01-01

    ... 7 Agriculture 10 2011-01-01 2011-01-01 false Soybeans. 1220.128 Section 1220.128 Agriculture... AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN PROMOTION, RESEARCH, AND CONSUMER INFORMATION Soybean Promotion and Research Order Definitions § 1220.128 Soybeans. The...

  2. 'Weightless' acrylic painting by Jack Kroehnke

    NASA Technical Reports Server (NTRS)

    1987-01-01

    'Weightless' acrylic painting by Jack Kroehnke depicts STS-26 Discovery, Orbiter Vehicle (OV) 103, Mission Specialist (MS) David C. Hilmers participating in extravehicular activity (EVA) simulation in JSC Weightless Environment Training Facility (WETF) Bldg 29. In the payload bay (PLB) mockup, Hilmers, wearing extravehicular mobility unit (EMU), holds onto the mission-peculiar equipment support structure in foreground while SCUBA-equipped diver monitors activity overhead and camera operator records EVA procedures. Copyrighted art work for use by NASA.

  3. ICI/BASF PP for acrylics swap

    SciTech Connect

    Alperowicz, N.

    1993-01-27

    ICI (London) and BASF (Ludwigshafen) have announced their long-awaited polypropylene (PP) for acrylics swap deal. ICI is buying BASF's European acrylic resin business, and the German firm will acquire ICI's European PP operations. The deal is due for completion by mid-1993, subject to regulatory approvals. BASF, hitherto a small-scale PP producer, doubles capacity to 600,000 m.t./year and moves up the European PP league to number three, behind Himont and Shell. BASF, whose process is used in the plants, secures a foothold in the UK PP market, where Shell - planning a merger with Himont - is the only other producer, with 170,000 m.t./year. ICI's purchase involves BASF's Resart GmbH and Critesa SA subsidiaries, located at Mainz, Germany and near Barcelona, Spain, respectively. The business - which will add about [Brit pounds]60 million ($93 million) to ICI Acrylics [Brit pounds]300-million revenues - employs 400 people, who will transfer to ICI.

  4. Performance comparison of acrylic and thiol-acrylic resins in two-photon polymerization.

    PubMed

    Jiang, Lijia; Xiong, Wei; Zhou, Yushen; Liu, Ying; Huang, Xi; Li, Dawei; Baldacchini, Tommaso; Jiang, Lan; Lu, Yongfeng

    2016-06-13

    Microfabrication by two-photon polymerization is investigated using resins based on thiol-ene chemistry. In particular, resins containing different amounts of a tetrafunctional acrylic monomer and a tetrafunctional thiol molecule are used to create complex microstructures. We observe the enhancement of several characteristics of two-photon polymerization when using thiol-acrylic resins. Specifically, microfabrication is carried out using higher writing velocities and it produces stronger polymeric microstructures. Furthermore, the amount of shrinkage typically observed in the production of three-dimensional microstructures is reduced also. By means of microspectrometry, we confirm that the thiol-acrylate mixture in TPP resins promote monomer conversion inducing a higher degree of cross-linked network formation.

  5. Performance comparison of acrylic and thiol-acrylic resins in two-photon polymerization.

    PubMed

    Jiang, Lijia; Xiong, Wei; Zhou, Yushen; Liu, Ying; Huang, Xi; Li, Dawei; Baldacchini, Tommaso; Jiang, Lan; Lu, Yongfeng

    2016-06-13

    Microfabrication by two-photon polymerization is investigated using resins based on thiol-ene chemistry. In particular, resins containing different amounts of a tetrafunctional acrylic monomer and a tetrafunctional thiol molecule are used to create complex microstructures. We observe the enhancement of several characteristics of two-photon polymerization when using thiol-acrylic resins. Specifically, microfabrication is carried out using higher writing velocities and it produces stronger polymeric microstructures. Furthermore, the amount of shrinkage typically observed in the production of three-dimensional microstructures is reduced also. By means of microspectrometry, we confirm that the thiol-acrylate mixture in TPP resins promote monomer conversion inducing a higher degree of cross-linked network formation. PMID:27410383

  6. Aminoacylase 1-catalysed deacetylation of bioactives epoxides mycotoxin-derived mercapturates; 3,4-epoxyprecocenes as models of cytotoxic epoxides.

    PubMed

    Stocker, Pierre; Brunel, Jean Michel; de Rezende, Leandro; do Amaral, Antonia Tavares; Morelli, Xavier; Roche, Phillipe; Vidal, Nicolas; Giardina, Thierry; Perrier, Josette

    2012-08-01

    The mycotoxin aflatoxin B1 (AFB1) is a carcinogenic food contaminant which is metabolically activated by epoxydation. The metabolism of mycotoxins via the mercapturate metabolic pathway was shown, in general, to lead to their detoxication. Mercapturic acids thus formed (S-substitued-N-acetyl-l-cysteines) may be accumulated in the kidney and either excreted in the urine or desacetylated by Acylase 1 (ACY1) to yield cysteine S-conjugates. To be toxic, the N-acetyl-l-cysteine-S-conjugates first have to undergo deacetylation by ACY 1. The specificity and rate of mercapturic acid deacetylation may determine the toxicity, however the exact deacetylation processes involved are not well known. The aim of this study was to investigate the role of ACY1 in the toxicity of some bioactive epoxides from Aflatoxin B1. We characterized the kinetic parameters of porcine kidney and human recombinant aminoacylase-1 towards some aromatic and aliphatic-derived mercapturates analogue of mycotoxin-mercapturic acids and 3,4-epoxyprecocene, a bioactive epoxide derivated from aflatoxin. The deacetylation of mercapturated substrates was followed both by reverse phase HPLC and by TNBS method. Catalytic activity was discussed in a structure-function relationship. Ours results indicate for the first time that aminoacylase-1 could play an important role in deacetylating mercapturate metabolites of aflatoxin analogues and this process may be in relation with their cyto- and nephrotoxicity in human.

  7. Palladium (Ii) Catalyzed Polymerization Of Norbornene And Acrylates

    DOEpatents

    Sen, Ayusman; Kacker, Smita; Hennis, April; Polley, Jennifer D.

    2001-10-09

    Homopolymers or copolymers of acrylates, homopolymers or copolymers of norbornenes, and copolymers of acrylates with norbornenes, may be prepared by contacting acrylate and/or norbornene monomer reactant under polymerization conditions and in the presence of a solvent with a catalyst system consisting essentially of a Pd(II) dimer component having the formula: where L is a monodentate phosphorus or nitrogen ligand, X is an anionic group, and R is an alkyl or aryl group.

  8. Palladium (II) catalyized polymerization of norbornene and acrylates

    DOEpatents

    Sen, Ayusman; Kacker, Smita; Hennis, April; Polley, Jennifer D.

    2000-08-29

    Homopolymers or copolymers of acrylates, homopolymers or copolymers of norbornenes, and copolymers of acrylates with norbornenes, may be prepared by contacting acrylate and/or norbornene monomer reactant under polymerization conditions and in the presence of a solvent with a catalyst system consisting essentially of a Pd(II) dimer component having the formula: [(L)Pd(R)(X)].sub.2, where L is a monodentate phosphorus or nitrogen ligand, X is an anionic group, and R is an alkyl or aryl group.

  9. Primary structure and catalytic mechanism of the epoxide hydrolase from Agrobacterium radiobacter AD1.

    PubMed

    Rink, R; Fennema, M; Smids, M; Dehmel, U; Janssen, D B

    1997-06-01

    The epoxide hydrolase gene from Agrobacterium radiobacter AD1, a bacterium that is able to grow on epichlorohydrin as the sole carbon source, was cloned by means of the polymerase chain reaction with two degenerate primers based on the N-terminal and C-terminal sequences of the enzyme. The epoxide hydrolase gene coded for a protein of 294 amino acids with a molecular mass of 34 kDa. An identical epoxide hydrolase gene was cloned from chromosomal DNA of the closely related strain A. radiobacter CFZ11. The recombinant epoxide hydrolase was expressed up to 40% of the total cellular protein content in Escherichia coli BL21(DE3) and the purified enzyme had a kcat of 21 s-1 with epichlorohydrin. Amino acid sequence similarity of the epoxide hydrolase with eukaryotic epoxide hydrolases, haloalkane dehalogenase from Xanthobacter autotrophicus GJ10, and bromoperoxidase A2 from Streptomyces aureofaciens indicated that it belonged to the alpha/beta-hydrolase fold family. This conclusion was supported by secondary structure predictions and analysis of the secondary structure with circular dichroism spectroscopy. The catalytic triad residues of epoxide hydrolase are proposed to be Asp107, His275, and Asp246. Replacement of these residues to Ala/Glu, Arg/Gln, and Ala, respectively, resulted in a dramatic loss of activity for epichlorohydrin. The reaction mechanism of epoxide hydrolase proceeds via a covalently bound ester intermediate, as was shown by single turnover experiments with the His275 --> Arg mutant of epoxide hydrolase in which the ester intermediate could be trapped.

  10. Pulse radiolysis of aqueous solutions of ethyl acrylate and hydroxy ethyl acrylate

    NASA Astrophysics Data System (ADS)

    Safrany, A.; Biro, A.; Wojnarovits, L.

    1993-10-01

    Ethyl- and hydroxy ethyl acrylate show high reactivities with hydrated electron and hydroxyl radical intermediates of water radiolysis. The electron adduct reversibly protonate with pK values of 5.7 and 7.3. The adducts may take part in irreversible protonation at the β carbon atom forming α-carboxyl alkyl radicals. Same type of radical forms in reaction of acrylates with OH: at low concentration the adduct mainly disappear in self termination reactions. Above 5 mmol dm -1 the signals showed the startup of oligomerization.

  11. Severe Onychodystrophy due to Allergic Contact Dermatitis from Acrylic Nails

    PubMed Central

    Mattos Simoes Mendonca, Marcela; LaSenna, Charlotte; Tosti, Antonella

    2015-01-01

    Acrylic nails, including sculptured nails and the new ultraviolet-curable gel polish lacquers, have been associated with allergic contact dermatitis (ACD). We report 2 cases of ACD to acrylic nails with severe onychodystrophy and psoriasiform changes including onycholysis and subungual hyperkeratosis. In both cases, the patients did not realize the association between the use of acrylate-based manicures and nail changes. One patient had been previously misdiagnosed and treated unsuccessfully for nail psoriasis. The informed clinician should elicit a history of acrylic manicure in patients with these nail changes, especially in cases of suspected nail psoriasis refractory to treatment. Patch testing is a useful tool in confirming diagnosis. PMID:27170940

  12. Severe Onychodystrophy due to Allergic Contact Dermatitis from Acrylic Nails.

    PubMed

    Mattos Simoes Mendonca, Marcela; LaSenna, Charlotte; Tosti, Antonella

    2015-09-01

    Acrylic nails, including sculptured nails and the new ultraviolet-curable gel polish lacquers, have been associated with allergic contact dermatitis (ACD). We report 2 cases of ACD to acrylic nails with severe onychodystrophy and psoriasiform changes including onycholysis and subungual hyperkeratosis. In both cases, the patients did not realize the association between the use of acrylate-based manicures and nail changes. One patient had been previously misdiagnosed and treated unsuccessfully for nail psoriasis. The informed clinician should elicit a history of acrylic manicure in patients with these nail changes, especially in cases of suspected nail psoriasis refractory to treatment. Patch testing is a useful tool in confirming diagnosis. PMID:27170940

  13. Detection of genetically modified soybean in crude soybean oil.

    PubMed

    Nikolić, Zorica; Vasiljević, Ivana; Zdjelar, Gordana; Ðorđević, Vuk; Ignjatov, Maja; Jovičić, Dušica; Milošević, Dragana

    2014-02-15

    In order to detect presence and quantity of Roundup Ready (RR) soybean in crude oil extracted from soybean seed with a different percentage of GMO seed two extraction methods were used, CTAB and DNeasy Plant Mini Kit. The amplifications of lectin gene, used to check the presence of soybean DNA, were not achieved in all CTAB extracts of DNA, while commercial kit gave satisfactory results. Comparing actual and estimated GMO content between two extraction methods, root mean square deviation for kit is 0.208 and for CTAB is 2.127, clearly demonstrated superiority of kit over CTAB extraction. The results of quantification evidently showed that if the oil samples originate from soybean seed with varying percentage of RR, it is possible to monitor the GMO content at the first stage of processing crude oil.

  14. Detection of genetically modified soybean in crude soybean oil.

    PubMed

    Nikolić, Zorica; Vasiljević, Ivana; Zdjelar, Gordana; Ðorđević, Vuk; Ignjatov, Maja; Jovičić, Dušica; Milošević, Dragana

    2014-02-15

    In order to detect presence and quantity of Roundup Ready (RR) soybean in crude oil extracted from soybean seed with a different percentage of GMO seed two extraction methods were used, CTAB and DNeasy Plant Mini Kit. The amplifications of lectin gene, used to check the presence of soybean DNA, were not achieved in all CTAB extracts of DNA, while commercial kit gave satisfactory results. Comparing actual and estimated GMO content between two extraction methods, root mean square deviation for kit is 0.208 and for CTAB is 2.127, clearly demonstrated superiority of kit over CTAB extraction. The results of quantification evidently showed that if the oil samples originate from soybean seed with varying percentage of RR, it is possible to monitor the GMO content at the first stage of processing crude oil. PMID:24128586

  15. Data set of optimal parameters for colorimetric red assay of epoxide hydrolase activity.

    PubMed

    de Oliveira, Gabriel Stephani; Adriani, Patricia Pereira; Borges, Flavia Garcia; Lopes, Adriana Rios; Campana, Patricia T; Chambergo, Felipe S

    2016-09-01

    The data presented in this article are related to the research article entitled "Epoxide hydrolase of Trichoderma reesei: Biochemical properties and conformational characterization" [1]. Epoxide hydrolases (EHs) are enzymes that catalyze the hydrolysis of epoxides to the corresponding vicinal diols. This article describes the optimal parameters for the colorimetric red assay to determine the enzymatic activity, with an emphasis on the characterization of the kinetic parameters, pH optimum and thermal stability of this enzyme. The effects of reagents that are not resistant to oxidation by sodium periodate on the reactions can generate false positives and interfere with the final results of the red assay. PMID:27366781

  16. Mechanism of olefin epoxidation in the presence of a titanium-containing zeolite

    NASA Astrophysics Data System (ADS)

    Danov, S. M.; Krasnov, V. L.; Sulimov, A. V.; Ovcharova, A. V.

    2013-11-01

    The effect of the nature of a solvent on the liquid-phase epoxidation of olefins with an aqueous solution of hydrogen peroxide over a titanium-containing zeolite is studied. Butanol-1, butanol-2, propanol-1, isopropanol, methanol, ethanol, water, acetone, methyl ethyl ketone, isobutanol, and tert-butanol are examined as solvents. A mechanism of olefin epoxidation with hydrogen peroxide in an alcohol medium over a titanium-containing zeolite is proposed. Epoxidation reactions involving hydrogen peroxide and different olefins are studied experimentally.

  17. Methods of producing epoxides from alkenes using a two-component catalyst system

    DOEpatents

    Kung, Mayfair C.; Kung, Harold H.; Jiang, Jian

    2013-07-09

    Methods for the epoxidation of alkenes are provided. The methods include the steps of exposing the alkene to a two-component catalyst system in an aqueous solution in the presence of carbon monoxide and molecular oxygen under conditions in which the alkene is epoxidized. The two-component catalyst system comprises a first catalyst that generates peroxides or peroxy intermediates during oxidation of CO with molecular oxygen and a second catalyst that catalyzes the epoxidation of the alkene using the peroxides or peroxy intermediates. A catalyst system composed of particles of suspended gold and titanium silicalite is one example of a suitable two-component catalyst system.

  18. Bradyrhizobium japonicum Survival in and Soybean Inoculation with Fluid Gels.

    PubMed

    Jawson, M D; Franzluebbers, A J; Berg, R K

    1989-03-01

    The utilization of gels, which are used for fluid drilling of seeds, as carriers of Bradyrhizobium japonicum for soybean (Glycine max (L.) Merr.) inoculation was studied. Gels of various chemical composition (magnesium silicate, potassium acrylate-acrylamide, grafted starch, and hydroxyethyl cellulose) were used, although the hydroxyethyl cellulose gels were more extensively investigated. Gel inocula were prepared by mixing gel powder with liquid cultures of B. japonicum (2% [wt/vol]). The population of B. japonicum USDA 110 did not change in each gel type during 8 days of incubation at 28 degrees C. These fluid gels were prepared with late-exponential-growth-phase cells that were washed and suspended in physiological saline. Mid-exponential-growth-phase B. japonicum USDA 110, 123, and 138 grew in cellulose gels prepared with yeast extract-mannitol broth as well as or better than in yeast extract-mannitol broth alone for the first 10 days at 28 degrees C. Populations in these cellulose gels after 35 days were as large as when the gels had originally been prepared, and survival occurred for at least 70 days. Soybeans grown in sand in the greenhouse had greater nodule numbers, nodule weights, and top weights with gel inoculants compared with a peat inoculant. In soil containing 10 indigenous B. japonicum per g of soil, inoculation resulted in increased soybean nodule numbers, nodule weights, and top weights, but only nodule numbers were greater with gel than with peat inoculation. The gel-treated seeds carried 10 to 10 more bacteria per seed (10 to 10) than did the peat-treated seeds. PMID:16347870

  19. Antitermite activity of beta-caryophyllene epoxide and episulfide.

    PubMed

    Ashitani, Tatsuya; Kusumoto, Norihisa; Borg-Karlson, Anna-Karin; Fujita, Koki; Takahashi, Koetsu

    2013-01-01

    Caryophyllene-6,7-epoxide and caryophyllene-6,7-episulfide can be easily synthesized from beta-caryophyllene by autoxidation or episulfidation. The bioactivities of beta-caryophyllene and its derivatives were investigated against the subterranean termite Reticulitermes speratus Kolbe. The antifeedant, feeding, and termiticidal activities of each compound were tested using no-choice, dual-choice, and non-contact methods. Antitermitic activities were not shown by beta-caryophyllene, but were observed for the oxide and sulfide derivatives. Caryophyllene-6,7-episulfide showed especially high antifeedant and termiticidal activities. Thus, naturally abundant, non-bioactive beta-caryophyllene can be easily converted into an antitermite reagent via a non-biological process. PMID:24066515

  20. Olefin Epoxidation in Aqueous Phase Using Ionic-Liquid Catalysts.

    PubMed

    Cokoja, Mirza; Reich, Robert M; Wilhelm, Michael E; Kaposi, Marlene; Schäffer, Johannes; Morris, Danny S; Münchmeyer, Christian J; Anthofer, Michael H; Markovits, Iulius I E; Kühn, Fritz E; Herrmann, Wolfgang A; Jess, Andreas; Love, Jason B

    2016-07-21

    Hydrophobic imidazolium-based ionic liquids (IL) act as catalysts for the epoxidation of unfunctionalized olefins in water using hydrogen peroxide as oxidant. Although the catalysts are insoluble in both the substrate and in water, surprisingly, they are very well soluble in aqueous H2 O2 solution, owing to perrhenate-H2 O2 interactions. Even more remarkably, the presence of the catalyst also boosts the solubility of substrate in water. This effect is crucially dependent on the cation design. Hence, the imidazolium perrhenates enable both the transfer of hydrophobic substrate into the aqueous phase, and serve as actual catalysts, which is unprecedented. At the end of the reaction and in absence of H2 O2 the IL catalyst forms a third phase next to the lipophilic product and water and can easily be recycled.

  1. Structure of a bacterial homologue of vitamin K epoxide reductase

    SciTech Connect

    Li, Weikai; Schulman, Sol; Dutton, Rachel J.; Boyd, Dana; Beckwith, Jon; Rapoport, Tom A.

    2010-03-19

    Vitamin K epoxide reductase (VKOR) generates vitamin K hydroquinone to sustain {gamma}-carboxylation of many blood coagulation factors. Here, we report the 3.6 {angstrom} crystal structure of a bacterial homologue of VKOR from Synechococcus sp. The structure shows VKOR in complex with its naturally fused redox partner, a thioredoxin-like domain, and corresponds to an arrested state of electron transfer. The catalytic core of VKOR is a four transmembrane helix bundle that surrounds a quinone, connected through an additional transmembrane segment with the periplasmic thioredoxin-like domain. We propose a pathway for how VKOR uses electrons from cysteines of newly synthesized proteins to reduce a quinone, a mechanism confirmed by in vitro reconstitution of vitamin K-dependent disulphide bridge formation. Our results have implications for the mechanism of the mammalian VKOR and explain how mutations can cause resistance to the VKOR inhibitor warfarin, the most commonly used oral anticoagulant.

  2. Characteristics of polyaniline cobalt supported catalysts for epoxidation reactions.

    PubMed

    Kowalski, Grzegorz; Pielichowski, Jan; Grzesik, Mirosław

    2014-01-01

    A study of polyaniline (PANI) doping with various cobalt compounds, that is, cobalt(II) chloride, cobalt(II) acetate, and cobalt(II) salen, is presented. The catalysts were prepared by depositing cobalt compounds onto the polymer surface. PANI powders containing cobalt ions were obtained by one- or two-step method suspending PANI in the following acetonitrile/acetic acid solution or acetonitrile and then acetic acid solution. Moreover different ratios of Co(II) : PANI were studied. Catalysts obtained with both methods and at all ratios were investigated using various techniques including AAS and XPS spectroscopy. The optimum conditions for preparation of PANI/Co catalysts were established. Catalytic activity of polyaniline cobalt(II) supported catalysts was tested in dec-1-ene epoxidation with molecular oxygen at room temperature. The relationship between the amount of cobalt species, measured with both AAS and XPS techniques, and the activity of PANI-Co catalysts has been established.

  3. Olefin Epoxidation in Aqueous Phase Using Ionic-Liquid Catalysts.

    PubMed

    Cokoja, Mirza; Reich, Robert M; Wilhelm, Michael E; Kaposi, Marlene; Schäffer, Johannes; Morris, Danny S; Münchmeyer, Christian J; Anthofer, Michael H; Markovits, Iulius I E; Kühn, Fritz E; Herrmann, Wolfgang A; Jess, Andreas; Love, Jason B

    2016-07-21

    Hydrophobic imidazolium-based ionic liquids (IL) act as catalysts for the epoxidation of unfunctionalized olefins in water using hydrogen peroxide as oxidant. Although the catalysts are insoluble in both the substrate and in water, surprisingly, they are very well soluble in aqueous H2 O2 solution, owing to perrhenate-H2 O2 interactions. Even more remarkably, the presence of the catalyst also boosts the solubility of substrate in water. This effect is crucially dependent on the cation design. Hence, the imidazolium perrhenates enable both the transfer of hydrophobic substrate into the aqueous phase, and serve as actual catalysts, which is unprecedented. At the end of the reaction and in absence of H2 O2 the IL catalyst forms a third phase next to the lipophilic product and water and can easily be recycled. PMID:27219852

  4. Identification of potent inhibitors of the chicken soluble epoxide hydrolase

    PubMed Central

    Shihadih, Diyala S.; Harris, Todd R.; Yang, Jun; Merzlikin, Oleg; Lee, Kin Sing S.; Hammock, Bruce D.; Morisseau, Christophe

    2014-01-01

    In vertebrates, soluble epoxide hydrolase (sEH) hydrolyzes natural epoxy-fatty acids (EpFAs), which are chemical mediators modulating inflammation, pain, and angiogenesis. Chick embryos are used to study angiogenesis, particularly its role in cardiovascular biology and pathology. To find potent and bio-stable inhibitors of the chicken sEH (chxEH) a library of human sEH inhibitors was screened. Derivatives of 1(adamantan-1-yl)-3-(trans-4-phenoxycyclohexyl) urea were found to be very potent tight binding inhibitors (KI < 150 pM) of chxEH while being relatively stable in chicken liver microsomes, suggesting their usefulness to study the role of EpFAs in chickens. PMID:25479771

  5. Conformational diversity and enantioconvergence in potato epoxide hydrolase 1.

    PubMed

    Bauer, P; Carlsson, Å Janfalk; Amrein, B A; Dobritzsch, D; Widersten, M; Kamerlin, S C L

    2016-06-28

    Potato epoxide hydrolase 1 (StEH1) is a biocatalytically important enzyme that exhibits rich enantio- and regioselectivity in the hydrolysis of chiral epoxide substrates. In particular, StEH1 has been demonstrated to enantioconvergently hydrolyze racemic mixes of styrene oxide (SO) to yield (R)-1-phenylethanediol. This work combines computational, crystallographic and biochemical analyses to understand both the origins of the enantioconvergent behavior of the wild-type enzyme, as well as shifts in activities and substrate binding preferences in an engineered StEH1 variant, R-C1B1, which contains four active site substitutions (W106L, L109Y, V141K and I155V). Our calculations are able to reproduce both the enantio- and regioselectivities of StEH1, and demonstrate a clear link between different substrate binding modes and the corresponding selectivity, with the preferred binding modes being shifted between the wild-type enzyme and the R-C1B1 variant. Additionally, we demonstrate that the observed changes in selectivity and the corresponding enantioconvergent behavior are due to a combination of steric and electrostatic effects that modulate both the accessibility of the different carbon atoms to the nucleophilic side chain of D105, as well as the interactions between the substrate and protein amino acid side chains and active site water molecules. Being able to computationally predict such subtle effects for different substrate enantiomers, as well as to understand their origin and how they are affected by mutations, is an important advance towards the computational design of improved biocatalysts for enantioselective synthesis. PMID:27049844

  6. Expanding the Catalytic Triad in Epoxide Hydrolases and Related Enzymes

    PubMed Central

    2015-01-01

    Potato epoxide hydrolase 1 exhibits rich enantio- and regioselectivity in the hydrolysis of a broad range of substrates. The enzyme can be engineered to increase the yield of optically pure products as a result of changes in both enantio- and regioselectivity. It is thus highly attractive in biocatalysis, particularly for the generation of enantiopure fine chemicals and pharmaceuticals. The present work aims to establish the principles underlying the activity and selectivity of the enzyme through a combined computational, structural, and kinetic study using the substrate trans-stilbene oxide as a model system. Extensive empirical valence bond simulations have been performed on the wild-type enzyme together with several experimentally characterized mutants. We are able to computationally reproduce the differences between the activities of different stereoisomers of the substrate and the effects of mutations of several active-site residues. In addition, our results indicate the involvement of a previously neglected residue, H104, which is electrostatically linked to the general base H300. We find that this residue, which is highly conserved in epoxide hydrolases and related hydrolytic enzymes, needs to be in its protonated form in order to provide charge balance in an otherwise negatively charged active site. Our data show that unless the active-site charge balance is correctly treated in simulations, it is not possible to generate a physically meaningful model for the enzyme that can accurately reproduce activity and selectivity trends. We also expand our understanding of other catalytic residues, demonstrating in particular the role of a noncanonical residue, E35, as a “backup base” in the absence of H300. Our results provide a detailed view of the main factors driving catalysis and regioselectivity in this enzyme and identify targets for subsequent enzyme design efforts. PMID:26527505

  7. Acrylic Finger Prosthesis: A Case Report

    PubMed Central

    Bandela, Vinod; M, Bharathi; S V, Giridhar Reddy

    2014-01-01

    Hands basic function is to grasp, hold and manipulate items. Hand gesture is perhaps the most blatant example of non-verbal communication. Finger and partial finger amputations are most frequently encountered forms of partial hand loss. Common causes are traumatic injuries, congenital absence or malformations present great clinical challenges. In addition to immediate loss of grasp strength, finger absence may cause marked psychological trauma. Individuals who desire finger replacement usually have high expectation for the appearance of prosthesis. This clinical report portrays simple method to retain acrylic finger prosthesis. PMID:25302271

  8. A Computational Study of Acid Catalyzed Aerosol Reactions of Atmospherically Relevant Epoxides

    EPA Science Inventory

    Epoxides are important intermediates of atmospheric isoprene oxidation. Their subsequent reactions in the particle phase lead to the production of organic compounds detected in ambient aerosols. We apply density functional theory to determine the important kinetic factors that ...

  9. Epoxidation of trans-cyclooctene by Methyltrioxorhenium/H(2)O(2): reaction of trans-epoxide with the monoperoxo complex

    PubMed

    Adam; Saha-Moller; Weichold

    2000-08-11

    The epoxidation of trans-cyclooctene (trans-1) with the MTO/H(2)O(2), MTO/UHP, and NaY/MTO/H(2)O(2) oxidants leads to a mixture of trans/cis-olefins 1, trans/cis-epoxides 2, and the cis-diol 3. While the oxygen transfer proceeds stereoselectively, the monoperoxo rhenium complex A, which is generated in situ during the catalytic cycle, is responsible for the facile deoxygenation, isomerization, and hydrolysis of the trans-epoxide. In the case of the homogeneous MTO/H(2)O(2) system, rapid decomposition of the catalytically active rhenium species into HReO(4) circumvents the formation of such side products. In contrast, for the heterogeneous oxidants MTO/UHP and NaY/MTO/H(2)O(2), the catalytically active rhenium species are sufficiently stabilized and survive long enough to promote the observed side reactions.

  10. Discovery of Potent Non-urea Inhibitors of Soluble Epoxide Hydrolase

    PubMed Central

    Xie, Yuli; Liu, Yidong; Gong, Gangli; Smith, Deborah H.; Yan, Fang; Rinderspacher, Alison; Feng, Yan; Zhu, Zhengxiang; Li, Xiangpo; Deng, Shi-Xian; Branden, Lars; Vidović, Dušica; Chung, Caty; Schürer, Stephan; Morisseau, Christophe; Hammock, Bruce D.; Landry, Donald W.

    2009-01-01

    Soluble epoxide hydrolase (sEH) is a novel target for the treatment of hypertension and vascular inflammation. A new class of potent non-urea sEH inhibitors was identified via high throughput screening (HTS) and chemical modification. IC50s of the most potent compounds range from micromolar to low nanomolar. A Class of potent non-Urea inhibitors of soluble epoxide hydrolase was discovered via high throughput screening and SARs-guided modification. PMID:19303288

  11. Hydroxyl-Substituted Ladder Polyethers via Selective Tandem Epoxidation/Cyclization Sequence

    PubMed Central

    Czabaniuk, Lara C.; Jamison, Timothy F.

    2015-01-01

    A new and highly selective method for the synthesis of hydroxyl-substituted tetrahydropyrans is described. This method utilizes titanium(IV) iso-propoxide and diethyl tartrate to perform a diastereoselective epoxidation followed by in situ epoxide activation and highly selective endo-cyclization to form the desired tetrahydropyran ring. The HIJ ring fragment of the marine ladder polyether yessotoxin was synthesized using this two-stage tactic that proceeds with high efficiency and excellent regioselectivity. PMID:25647091

  12. Highly Active Titanocene Catalysts for Epoxide Hydrosilylation: Synthesis, Theory, Kinetics, EPR Spectroscopy.

    PubMed

    Henriques, Dina Schwarz G; Zimmer, Katharina; Klare, Sven; Meyer, Andreas; Rojo-Wiechel, Elena; Bauer, Mirko; Sure, Rebecca; Grimme, Stefan; Schiemann, Olav; Flowers, Robert A; Gansäuer, Andreas

    2016-06-27

    A catalytic system for titanocene-catalyzed epoxide hydrosilylation is described. It features a straightforward preparation of titanocene hydrides that leads to a reaction with low catalyst loading, high yields, and high selectivity of radical reduction. The mechanism was studied by a suite of methods, including kinetic studies, EPR spectroscopy, and computational methods. An unusual resting state leads to the observation of an inverse rate order with respect to the epoxide.

  13. The Epoxidation of Carbonyl Compounds with a Benzyne-Triggered Sulfur Ylide.

    PubMed

    Lou, Mei-Mei; Wang, Han; Song, Li; Liu, Hong-Yi; Li, Zhong-Qiu; Guo, Xiao-Shuang; Zhang, Fu-Geng; Wang, Bin

    2016-07-15

    An efficient method for the synthesis of epoxides from carbonyl compounds, sulfoxides, and benzyne is presented. The strategy involved an epoxidation by a sulfur ylide which is formed in situ from sulfoxide and benzyne through the S-O bond insertion and deprotonation. This one-pot reaction proceeds under mild and base-free conditions, providing a convenient way to introduce the substituted methylene groups onto the carbonyl carbon.

  14. Highly Active Titanocene Catalysts for Epoxide Hydrosilylation: Synthesis, Theory, Kinetics, EPR Spectroscopy.

    PubMed

    Henriques, Dina Schwarz G; Zimmer, Katharina; Klare, Sven; Meyer, Andreas; Rojo-Wiechel, Elena; Bauer, Mirko; Sure, Rebecca; Grimme, Stefan; Schiemann, Olav; Flowers, Robert A; Gansäuer, Andreas

    2016-06-27

    A catalytic system for titanocene-catalyzed epoxide hydrosilylation is described. It features a straightforward preparation of titanocene hydrides that leads to a reaction with low catalyst loading, high yields, and high selectivity of radical reduction. The mechanism was studied by a suite of methods, including kinetic studies, EPR spectroscopy, and computational methods. An unusual resting state leads to the observation of an inverse rate order with respect to the epoxide. PMID:27125466

  15. Bromine-catalyzed conversion of CO2 and epoxides to cyclic carbonates under continuous flow conditions.

    PubMed

    Kozak, Jennifer A; Wu, Jie; Su, Xiao; Simeon, Fritz; Hatton, T Alan; Jamison, Timothy F

    2013-12-11

    A continuous method for the formation of cyclic carbonates from epoxides and carbon dioxide (CO2) is described. The catalysts used are inexpensive and effective in converting the reagents to the products in a residence time (t(R)) of 30 min. The cyclic carbonate products are obtained in good to excellent yield (51-92%). On the basis of a series of kinetics experiments, we propose a reaction mechanism involving epoxide activation by electrophilic bromine and CO2 activation by an amide.

  16. Alkylation of 2-substituted (6-methyl-2-pyridyl)methyllithium species with epoxides

    PubMed Central

    Vyvyan, James R.; Brown, Rebecca C.; Woods, Brian P.

    2009-01-01

    Substituted (6-methyl-2-pyridyl)methyllithium species were reacted with 1,2-epoxyoctane and 2-methyl-2,3-epoxynonane. The monosubstituted epoxide reacted efficiently with lutidyllithium and a number of 2-substituted-(6-methyl-2-pyridyl)methyllithium derivatives. The trisubstituted epoxide gave low yields of adducts with all (2-pyridyl)methyllithium species studied. These results are discussed in the context of a proposed synthesis of cananodine. PMID:19113936

  17. 40 CFR 721.10500 - Acrylated mixed metal oxides (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acrylated mixed metal oxides (generic... Specific Chemical Substances § 721.10500 Acrylated mixed metal oxides (generic). (a) Chemical substance and... mixed metal oxides (PMN P-06-341) is subject to reporting under this section for the significant...

  18. 40 CFR 721.10500 - Acrylated mixed metal oxides (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acrylated mixed metal oxides (generic... Specific Chemical Substances § 721.10500 Acrylated mixed metal oxides (generic). (a) Chemical substance and... mixed metal oxides (PMN P-06-341) is subject to reporting under this section for the significant...

  19. 40 CFR 721.8082 - Polyester polyurethane acrylate.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Polyester polyurethane acrylate. 721... Substances § 721.8082 Polyester polyurethane acrylate. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as polyester polyurethane...

  20. 40 CFR 721.8082 - Polyester polyurethane acrylate.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Polyester polyurethane acrylate. 721... Substances § 721.8082 Polyester polyurethane acrylate. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as polyester polyurethane...

  1. 40 CFR 721.8082 - Polyester polyurethane acrylate.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Polyester polyurethane acrylate. 721... Substances § 721.8082 Polyester polyurethane acrylate. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as polyester polyurethane...

  2. 40 CFR 721.8082 - Polyester polyurethane acrylate.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Polyester polyurethane acrylate. 721... Substances § 721.8082 Polyester polyurethane acrylate. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as polyester polyurethane...

  3. 40 CFR 721.8082 - Polyester polyurethane acrylate.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Polyester polyurethane acrylate. 721... Substances § 721.8082 Polyester polyurethane acrylate. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as polyester polyurethane...

  4. The Acrylation of Glycerol: a Precursor to Functionalized Lipids

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Didecanoylacryloylglycerol was synthesized from decanoic and acrylic acids and glycerol using K2O as catalyst. This reaction was carried out in hexane in a closed stainless steel reactor at 200°C for 5h. The reactants were added in a 1:3:4 glycerol:decanoic acid:acrylic acid molar ratio. The resu...

  5. 40 CFR 721.10307 - Acrylate resin (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acrylate resin (generic). 721.10307 Section 721.10307 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10307 Acrylate resin...

  6. 40 CFR 721.330 - Aromatic acrylate (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.330 Aromatic acrylate (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an aromatic acrylate (PMN P-01-420)...

  7. 40 CFR 721.330 - Aromatic acrylate (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.330 Aromatic acrylate (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an aromatic acrylate (PMN P-01-420)...

  8. Enantioselective epoxidation and carbon-carbon bond cleavage catalyzed by Coprinus cinereus peroxidase and myeloperoxidase.

    PubMed

    Tuynman, A; Spelberg, J L; Kooter, I M; Schoemaker, H E; Wever, R

    2000-02-01

    We demonstrate that myeloperoxidase (MPO) and Coprinus cinereus peroxidase (CiP) catalyze the enantioselective epoxidation of styrene and a number of substituted derivatives with a reasonable enantiomeric excess (up to 80%) and in a moderate yield. Three major differences with respect to the chloroperoxidase from Caldariomyces fumago (CPO) are observed in the reactivity of MPO and CiP toward styrene derivatives. First, in contrast to CPO, MPO and CiP produced the (S)-isomers of the epoxides in enantiomeric excess. Second, for MPO and CiP the H(2)O(2) had to be added very slowly (10 eq in 16 h) to prevent accumulation of catalytically inactive enzyme intermediates. Under these conditions, CPO hardly showed any epoxidizing activity; only with a high influx of H(2)O(2) (300 eq in 1.6 h) was epoxidation observed. Third, both MPO and CiP formed significant amounts of (substituted) benzaldehydes as side products as a consequence of C-alpha-C-beta bond cleavage of the styrene derivatives, whereas for CPO and cytochrome c peroxidase this activity is not observed. C-alpha-C-beta cleavage was the most prominent reaction catalyzed by CiP, whereas with MPO the relative amount of epoxide formed was higher. This is the first report of peroxidases catalyzing both epoxidation reactions and carbon-carbon bond cleavage. The results are discussed in terms of mechanisms involving ferryl oxygen transfer and electron transfer, respectively.

  9. Organic foliar Milstop shows efficacy against soybean aphid (Aphis glycines) on soybean (Glycine max)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean (Glycine max (L.) Merr.) has been produced in the United States since 1765. Soybean aphids (Aphis glycines Matsumura) were first detected on soybean in the United States in 2000 and now cause an estimated yield loss of up to US$4.9 billion annually. Organic soybean producers have few insecti...

  10. Epoxidation Activities of Human Cytochromes P450c17 and P450c21

    PubMed Central

    2015-01-01

    Some cytochrome P450 enzymes epoxidize unsaturated substrates, but this activity has not been described for the steroid hydroxylases. Physiologic steroid substrates, however, lack carbon–carbon double bonds in the parts of the pregnane molecules where steroidogenic hydroxylations occur. Limited data on the reactivity of steroidogenic P450s toward olefinic substrates exist, and the study of occult activities toward alternative substrates is a fundamental aspect of the growing field of combinatorial biosynthesis. We reasoned that human P450c17 (steroid 17-hydroxylase/17,20-lyase, CYP17A1), which 17- and 16α-hydroxylates progesterone, might catalyze the formation of the 16α,17-epoxide from 16,17-dehydroprogesterone (pregna-4,16-diene-3,20-dione). CYP17A1 catalyzed the novel 16α,17-epoxidation and the ordinarily minor 21-hydroxylation of 16,17-dehydroprogesterone in a 1:1 ratio. CYP17A1 mutation A105L, which has reduced progesterone 16α-hydroxylase activity, gave a 1:5 ratio of epoxide:21-hydroxylated products. In contrast, human P450c21 (steroid 21-hydroxylase, CYP21A2) converted 16,17-dehydroprogesterone to the 21-hydroxylated product and only a trace of epoxide. CYP21A2 mutation V359A, which has significant 16α-hydroxylase activity, likewise afforded the 21-hydroxylated product and slightly more epoxide. CYP17A1 wild-type and mutation A105L do not 21- or 16α-hydroxylate pregnenolone, but the enzymes 21-hydroxylated and 16α,17-epoxidized 16,17-dehydropregnenolone (pregna-5,16-diene-3β-ol-20-one) in 4:1 or 12:1 ratios, respectively. Catalase and superoxide dismutase did not prevent epoxide formation. The progesterone epoxide was not a time-dependent, irreversible CYP17A1 inhibitor. Our substrate modification studies have revealed occult epoxidase and 21-hydroxylase activities of CYP17A1, and the fraction of epoxide formed correlated with the 16α-hydroxylase activity of the enzymes. PMID:25386927

  11. 21 CFR 177.1340 - Ethylene-methyl acrylate copolymer resins.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Ethylene-methyl acrylate copolymer resins. 177...-methyl acrylate copolymer resins. Ethylene-methyl acrylate copolymer resins may be safely used as... prescribed conditions: (a) For the purpose of this section, the ethylene-methyl acrylate copolymer...

  12. Epoxide-Mediated Differential Packaging of Cif and Other Virulence Factors into Outer Membrane Vesicles

    PubMed Central

    Ballok, Alicia E.; Filkins, Laura M.; Bomberger, Jennifer M.; Stanton, Bruce A.

    2014-01-01

    Pseudomonas aeruginosa produces outer membrane vesicles (OMVs) that contain a number of secreted bacterial proteins, including phospholipases, alkaline phosphatase, and the CFTR inhibitory factor (Cif). Previously, Cif, an epoxide hydrolase, was shown to be regulated at the transcriptional level by epoxides, which serve as ligands of the repressor, CifR. Here, we tested whether epoxides have an effect on Cif levels in OMVs. We showed that growth of P. aeruginosa in the presence of specific epoxides but not a hydrolysis product increased Cif packaging into OMVs in a CifR-independent fashion. The outer membrane protein, OprF, was also increased under these conditions, but alkaline phosphatase activity was not significantly altered. Additionally, we demonstrated that OMV shape and density were affected by epoxide treatment, with two distinct vesicle fractions present when cells were treated with epibromohydrin (EBH), a model epoxide. Vesicles isolated from the two density fractions exhibited different protein profiles in Western blotting and silver staining. We have shown that a variety of clinically or host-relevant treatments, including antibiotics, also alter the proteins packaged in OMVs. Proteomic analysis of purified OMVs followed by an analysis of transposon mutant OMVs yielded mutants with altered vesicle packaging. Finally, epithelial cell cytotoxicity was reduced in the vesicles formed in the presence of EBH, suggesting that this epoxide alters the function of the OMVs. Our data support a model whereby clinically or host-relevant signals mediate differential packaging of virulence factors in OMVs, which results in functional consequences for host-pathogen interactions. PMID:25112474

  13. Patulin biosynthesis: Epoxidation of toluquinol and gentisyl alcohol by particulate preparations from Penicillium patulum

    SciTech Connect

    Priest, J.W.; Light, R.J. )

    1989-11-14

    A crude extract that catalyzes the epoxidation of toluquinol and gentisyl alcohol was isolated from cultures of Penicillium patulum. About 60% of the activity sedimented from crude extract upon centrifugation at 105000g for 2 h, and at 30000g for 30 min after precipitation with 30% ammonium sulfate and resuspension in buffer. The quinone epoxide phyllostine, a product of gentisyl alcohol epoxidation, has previously been shown to be an intermediate in the biosynthesis of patulin and was shown to be further converted to neopatulin by the extract. The epoxide product of toluquinol, desoxyphyllostine (2-methyl-5,6-epoxy-1,4-benzoquinone), has not been reported previously from fungal cultures. Its structure was confirmed by GC-mass spectrometry and proton and {sup 13}C NMR. Its CD spectrum showed the same shape and signs as that of phyllostine, indicating that it too is an enzymatic product with a similar absolute configuration. Whereas chemical epoxidation of toluquinone and gentisly quinone occurs with hydrogen peroxide, the enzymatic epoxidation utilized oxygen and the hydroquinone. The epoxidation was inhibited by 1,10-phenanthroline, EDTA, and {rho}-(chloromercuri)benzenesulfonic acid and by degassing with nitrogen, but no inhibition was observed with KCN, catalase, or CO. The apparent K{sub m}'s were similar for the two substrates with both substrates showing inhibition at 1.0 mM. The rate of desoxyphyllostine formation was more than 10 times that of phyllostine formation at equivalent substrate concentrations. Gentisaldehyde was not a substrate for the enzyme. The epoxidase was induced in late fermentor cultures of P. patulum with the same kinetics as m-hydroxybenzyl alcohol dehydrogenase, another enzyme associated with the induction of patulin biosynthesis.

  14. Final Report: Experimental and Theoretical Studies of Surface Oxametallacycles - Connections to Heterogeneous Olefin Epoxidation

    SciTech Connect

    Mark A. Barteau

    2009-09-15

    This project has aimed at the rational design of catalysts for direct epoxidation of olefins. This chemistry remains one of the most challenging problems in heterogeneous catalysis. Although the epoxidation of ethylene by silver catalysts to form ethylene oxide (EO) has been practiced for decades, little progress has been made in expanding this technology to other products and processes. We have made significant advances through the combination of surface science experiments, Density Functional Theory (DFT) calculations, and catalytic reactor experiments, toward understanding the mechanism of this reaction on silver catalysts, and to the rational improvement of selectivity. The key has been our demonstration of surface oxametallacycle intermediates as the species that control reaction selectivity. This discovery permits the influence of catalyst promoters on selectivity to be probed, and new catalyst formulations to be developed. It also guides the development of new chemistry with potential for direct epoxidation of more complex olefins. During the award period we have focused on 1. the formation and reaction selectivity of complex olefin epoxides on silver surfaces, and 2. the influence of co-adsorbed oxygen atoms on the reactions of surface oxametallacycles on silver, and 3. the computational prediction, synthesis, characterization and experimental evaluation of bimetallic catalysts for ethylene epoxidation. The significance of these research thrusts is as follows. Selective epoxidation of olefins more complex than ethylene requires suppression of not only side reactions available to the olefin such as C-H bond breaking, but it requires formation and selective ring closure of the corresponding oxametallacycle intermediates. The work carried out under this grant has significantly advanced the field of catalyst design from first principles. The combination of computational tools, surface science, and catalytic reactor experiments in a single laboratory has few

  15. A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl(4)-catalyzed arene-epoxide coupling.

    PubMed

    Elango, Shanmugham; Yan, Tu-Hsin

    2002-10-01

    A facile construction of the typical framework of narcissus alkaloids has been realized by virtue of the development of a practical route involving stereocontrolled epoxide formation and SnCl(4)-catalyzed arene-epoxide coupling. To achieve this goal, it proved to be necessary to devise a strategy that would enable chemical transformations to install an epoxy moiety in a congested environment. The successful preparation of a hindered epoxide from O-isopropylidene-protected 4-aminocyclohexenol required three steps consisting principally of controlled bromohydration and base-promoted closure and N-alkylation. It was found that a catalytic amount of SnCl(4) not only maintained the catalytic cycle but also effected clean arylation to form a fused BC ring system. Several tactics that ultimately proved to be unsatisfactory are also discussed in an effort to set important boundary limits on arene-epoxide coupling. The requisite enantiopure 4-aminocyclohexenol was available via an asymmetric cycloaddition of diene to camphor-based chloronitroso. The total synthesis of (+)-narciclasine was realized in nine steps with an overall yield of 19%.

  16. Thermal and mechanical properties of palm oil-based polyurethane acrylate/clay nanocomposites prepared by in-situ intercalative method and electron beam radiation

    SciTech Connect

    Salih, A. M.; Ahmad, Mansor Bin; Ibrahim, Nor Azowa; Dahlan, Khairul Zaman Hj Mohd; Tajau, Rida; Mahmood, Mohd Hilmi; Yunus, Wan Md. Zin Wan

    2014-02-12

    Palm oil based-polyurethane acrylate (POBUA)/clay nanocomposites were prepared via in-situ intercalative polymerization using epoxidized palm oil acrylate (EPOLA) and 4,4' methylene diphenyl diisocyante (MDI). Organically modified Montmorillonite (ODA-MMT) was incorporated in EPOLA (1, 3 and 5%wt), and then subjected to polycondensation reaction with MDI. Nanocomposites solid films were obtained successfully by electron beam radiation induced free radical polymerization (curing). FTIR results reveal that the prepolymer was obtained successfully, with nanoclay dispersed in the matrix. The intercalation of the clay in the polymer matrix was investigated by XRD and the interlayer spacing of clay was found to be increased up to 37 Å, while the structure morphology of the nanocomposites was investigated by TEM and SEM. The nanocomposites were found to be a mixture of exfoliated and intercalated morphologies. The thermal stability of the nanocomposites was significantly increased by incorporation of nanoclay into the polymer matrix. DSC results reveal that the Tg was shifted to higher values, gradually with increasing the amount of filler in the nanocomposites. Tensile strength and Young's modulus of the nanocomposites showed remarkable improvement compared to the neat POBUA.

  17. Thermal and mechanical properties of palm oil-based polyurethane acrylate/clay nanocomposites prepared by in-situ intercalative method and electron beam radiation

    NASA Astrophysics Data System (ADS)

    Salih, A. M.; Ahmad, Mansor Bin; Ibrahim, Nor Azowa; Dahlan, Khairul Zaman Hj Mohd; Tajau, Rida; Mahmood, Mohd Hilmi; Yunus, Wan Md. Zin Wan

    2014-02-01

    Palm oil based-polyurethane acrylate (POBUA)/clay nanocomposites were prepared via in-situ intercalative polymerization using epoxidized palm oil acrylate (EPOLA) and 4,4' methylene diphenyl diisocyante (MDI). Organically modified Montmorillonite (ODA-MMT) was incorporated in EPOLA (1, 3 and 5%wt), and then subjected to polycondensation reaction with MDI. Nanocomposites solid films were obtained successfully by electron beam radiation induced free radical polymerization (curing). FTIR results reveal that the prepolymer was obtained successfully, with nanoclay dispersed in the matrix. The intercalation of the clay in the polymer matrix was investigated by XRD and the interlayer spacing of clay was found to be increased up to 37 Å, while the structure morphology of the nanocomposites was investigated by TEM and SEM. The nanocomposites were found to be a mixture of exfoliated and intercalated morphologies. The thermal stability of the nanocomposites was significantly increased by incorporation of nanoclay into the polymer matrix. DSC results reveal that the Tg was shifted to higher values, gradually with increasing the amount of filler in the nanocomposites. Tensile strength and Young's modulus of the nanocomposites showed remarkable improvement compared to the neat POBUA.

  18. Electrochemical characterization of aminated acrylic conducting polymer

    SciTech Connect

    Rashid, Norma Mohammad; Heng, Lee Yook; Ling, Tan Ling

    2015-09-25

    New attempt has been made to synthesize aminated acrylic conducting polymer (AACP) using precursor of phenylvinylsulfoxide (PVS). The process was conducted via the integration of microemulsion and photopolymerization techniques. It has been utilized for covalent immobilization of amino groups by the adding of N-achryiloxisuccinimide (NAS). Thermal eliminating of benzene sulfenic acids from PVS has been done at 250 °C to form electroactive polyacetylene (PA) segment. Characterization of AACP has been conducted using fourier transform infrared (FTIR), scanning electron microscopy (SEM) and linear sweep cyclic voltammetry (CV). A range of 0.3-1.25μm particle size obtained from SEM characterization. A quasi-reversible system performed as shown in electrochemical study.

  19. Electrochemical characterization of aminated acrylic conducting polymer

    NASA Astrophysics Data System (ADS)

    Rashid, Norma Mohammad; Heng, Lee Yook; Ling, Tan Ling

    2015-09-01

    New attempt has been made to synthesize aminated acrylic conducting polymer (AACP) using precursor of phenylvinylsulfoxide (PVS). The process was conducted via the integration of microemulsion and photopolymerization techniques. It has been utilized for covalent immobilization of amino groups by the adding of N-achryiloxisuccinimide (NAS). Thermal eliminating of benzene sulfenic acids from PVS has been done at 250 °C to form electroactive polyacetylene (PA) segment. Characterization of AACP has been conducted using fourier transform infrared (FTIR), scanning electron microscopy (SEM) and linear sweep cyclic voltammetry (CV). A range of 0.3-1.25μm particle size obtained from SEM characterization. A quasi-reversible system performed as shown in electrochemical study.

  20. Flexible, stretchable electroadhesives based on acrylic elastomers

    NASA Astrophysics Data System (ADS)

    Duduta, Mihai; Wood, Robert J.; Clarke, David R.

    2016-04-01

    Controllable adhesion is a requirement for a wide variety of applications including robotic manipulation, as well as locomotion including walking, crawling and perching. Electroadhesives have several advantages such as reversibility, low power consumption and controllability based on applied voltage. Most demonstrations of electroadhesive devices rely on fairly rigid materials, which cannot be stretched reversibly, as needed in some applications. We have developed a fast and reliable method for building soft, stretchable electroadhesive pads based on acrylic elastomers and electrodes made of carbon nanotubes. The devices produced were tested pre-deformation and in a stretched configuration. The adhesive force was determined to be in the 0.1 - 3.0 N/cm2 range, depending on the adhering surface. The electroadhesive devices were integrated with pre-stretched dielectric elastomer actuators to create a device in which the adhesion force could be tuned by changes in either the applied voltage or total area.

  1. Custom cranioplasty using stereolithography and acrylic.

    PubMed

    D'Urso, P S; Earwaker, W J; Barker, T M; Redmond, M J; Thompson, R G; Effeney, D J; Tomlinson, F H

    2000-04-01

    Numerous methods of cranioplasty have been described. Customization and prefabrication have been reported to reduce operating time and improve cosmesis. An original technique for the manufacture of customized cranioplastic implants has been developed and tested in 30 patients.Thirty patients requiring cranioplasties were selected. Data acquired from computed tomography (CT) were used to manufacture exact plastic replicas (biomodels) of craniotomy defects and master cranioplastic implants using the rapid prototyping technology of stereolithography (SL). The three-dimensional (3D) imaging techniques of mirroring and interpolation were used to extrapolate on existing anatomy to design the master implants. The master implants were hand finished to fit the defect in the corresponding cranial biomodel exactly and were then used to create a cavity mould. The mould was used to cast thermally polymerised custom acrylic implants. The surgeons reported that the customized implants reduced operating time, afforded excellent cosmesis and were cost effective. The patients reported that the opportunity to see the biomodel and implant preoperatively improved their understanding of the procedure. Two complications were noted, one infection and one implant required significant trimming. The simultaneous manufacture of the master implant (male) and biomodel (female) components from SL allowed custom accurate implants to be manufactured. Disadvantages identified were the time required for computer manipulations of the CT data (up to 2 h), difficulty in assessing the accuracy of the computer generated master as a 3D rendering, the potential for SL parts to warp, manufacturing time (minimum 2 days) and the cost of approximately $1300 US per case ($1000 for the SL biomodel and $300 for the acrylic casting). PMID:10738323

  2. Poly(amide-graft-acrylate) interfacial compounds

    NASA Astrophysics Data System (ADS)

    Zamora, Michael Perez

    Graft copolymers with segments of dissimilar chemistries have been shown to be useful in a variety of applications as surfactants, compatibilizers, impact modifiers, and surface modifiers. The most common route to well defined graft copolymers is through the use of macromonomers, polymers containing a reactive functionality and thus capable of further polymerization. However, the majority of the studies thus far have focused on the synthesis of macromonomers capable of reacting with vinyl monomers to form graft copolymers. This study focused on the synthesis of macromonomers capable of participating in condensation polymerizations. A chain transfer functionalization method was utilized. Cysteine was evaluated as a chain transfer agent for the synthesis of amino acid functionalized poly(acrylate) and poly(methacrylate) macromonomers. Low molar mass, functionalized macromonomers were produced. These macromonomers were proven to be capable of reacting with amide precursors to form poly(amide-g-acrylate) graft copolymers. Macromonomers and graft copolymers were characterized by gel permeation chromatography (GPC), Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR) spectroscopy, elemental analysis (EA), inductively coupled plasma (ICP), and differential scanning calorimetry (DSC). The second part of this research involved poly(dimethacrylate) dental restorative materials. Volumetric shrinkage during the cure of these resins results in a poor interface between the resin and the remaining tooth structure, limiting the lifetime of these materials. Cyclic anhydrides were incorporated into common monomer compositions used in dental applications. Volume expansion from the ring opening hydrolysis of these anhydrides was shown to be feasible. The modified dental resins were characterized by swelling, extraction and ultraviolet spectroscopy (UV), and density measurements. Linear poLymers designed to model the crosslinked dental resins were

  3. Conversion of Lignocellulosic Biomass to Ethanol and Butyl Acrylate

    SciTech Connect

    Binder, Thomas; Erpelding, Michael; Schmid, Josef; Chin, Andrew; Sammons, Rhea; Rockafellow, Erin

    2015-04-10

    Conversion of Lignocellulosic Biomass to Ethanol and Butyl Acrylate. The purpose of Archer Daniels Midlands Integrated Biorefinery (IBR) was to demonstrate a modified acetosolv process on corn stover. It would show the fractionation of crop residue to distinct fractions of cellulose, hemicellulose, and lignin. The cellulose and hemicellulose fractions would be further converted to ethanol as the primary product and a fraction of the sugars would be catalytically converted to acrylic acid, with butyl acrylate the final product. These primary steps have been demonstrated.

  4. Investigation of Acrylic Acid at High Pressure Using Neutron Diffraction

    PubMed Central

    2014-01-01

    This article details the exploration of perdeuterated acrylic acid at high pressure using neutron diffraction. The structural changes that occur in acrylic acid-d4 are followed via diffraction and rationalized using the Pixel method. Acrylic acid undergoes a reconstructive phase transition to a new phase at ∼0.8 GPa and remains molecular to 7.2 GPa before polymerizing on decompression to ambient pressure. The resulting product is analyzed via Raman and FT-IR spectroscopy and differential scanning calorimetry and found to possess a different molecular structure compared with polymers produced via traditional routes. PMID:24650085

  5. Methods for the synthesis of deuterated acrylate salts

    SciTech Connect

    Yang, Jun; Bonnesen, Peter V.; Hong, Kunlun

    2014-09-09

    A method for synthesizing a deuterated acrylate of the Formula (1), the method comprising: (i) deuterating a propiolate compound of Formula (2) to a methyne-deuterated propiolate compound of Formula (3) in the presence of a base and D.sub.2O: and (ii) reductively deuterating the methyne-deuterated propiolate compound of Formula (3) in a reaction solvent in the presence of deuterium gas and a palladium-containing catalyst to afford the deuterated acrylate of the Formula (1). The resulting deuterated acrylate compounds, derivatives thereof, and polymers derived therefrom are also described.

  6. Grignard Reaction of an Epoxide: A Mechanistic Study

    NASA Astrophysics Data System (ADS)

    Ciaccio, James A.; Volpi, Sabrina; Clarke, Ransford

    1996-12-01

    Addition of PhMgBr to styrene oxide (1) affords a mixture of 2,2-diphenylethanol (3) and 1,2-diphenylethanol (6) (3:6 = 1:3); reversing the order of addition inverts the ratio of 3 to 6 formed (3:6 = 2:1). Students identify 3 and 6 by TLC comparison with authentic samples which they prepare by independent synthesis (hydride reduction of the corresponding carbonyl compounds), and establish the ratios of 3 to 6 by a combination of 1H and 13C NMR spectroscopies. This undergraduate experiment serves as an interesting alternative to more traditional Grignard experiments and is an excellent vehicle for a "discovery-based" experiment in which students are introduced to epoxide chemistry, share their laboratory data and make mechanistic conclusions from their experimental results. Unlike most undergraduate Grignard experiments which are performed merely for the sake of illustrating a textbook reaction, this Grignard synthesis is performed to probe the reactivity of styrene oxide. Students are required to analyze their products by TLC and NMR spectroscopy (instead of just submitting them for a grade) in order to obtain the data necessary for making mechanistic conclusions.

  7. Pharmacokinetic Screening of Soluble Epoxide Hydrolase Inhibitors in Dogs

    PubMed Central

    Tsai, Hsing-Ju; Hwang, Sung Hee; Morisseau, Christophe; Yang, Jun; Jones, Paul D.; Kasagami, Takeo; Kim, In-Hae; Hammock, Bruce D.

    2012-01-01

    Epoxyeicosatrienoic acids that have anti-hypertensive and anti-inflammatory properties are mainly metabolized by soluble epoxide hydrolase (sEH, EC 3.3.2.3). Therefore, sEH has emerged as a therapeutic target for treating various cardiovascular diseases and inflammatory pain. N,N’-Disubstituted ureas are potent sEH inhibitors in vitro. However, in vivo usage of early sEH inhibitors has been limited by their low bioavailability and poor physiochemical properties. Therefore, a group of highly potent compounds with more drug-like physiochemical properties were evaluated by monitoring their plasma profiles in dogs treated orally with sEH inhibitors. Urea compounds with an adamantyl or a 4-trifluoromethoxyphenyl group on one side and a piperidyl or a cyclohexyl ether group on the other side of the urea function showed pharmacokinetic profiles with high plasma concentrations and long half lives. In particular, the inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid (t-AUCB) not only is very potent with good physiochemical properties, but also shows high oral bioavailability for doses ranging from 0.01 to 1 mg/kg. This compound is also very potent against the sEH of several mammals, suggesting that t-AUCB will be an excellent tool to evaluate the biology of sEH in multiple animal models. Such compounds may also be a valuable lead for the development of veterinary therapeutics. PMID:20359531

  8. Terreic Acid, a Quinone Epoxide Inhibitor of Bruton's Tyrosine Kinase

    NASA Astrophysics Data System (ADS)

    Kawakami, Yuko; Hartman, Stephen E.; Kinoshita, Eiji; Suzuki, Hidefumi; Kitaura, Jiro; Yao, Libo; Inagaki, Naoki; Franco, Alessandra; Hata, Daisuke; Maeda-Yamamoto, Mari; Fukamachi, Hiromi; Nagai, Hiroichi; Kawakami, Toshiaki

    1999-03-01

    Bruton's tyrosine kinase (Btk) plays pivotal roles in mast cell activation as well as in B cell development. Btk mutations lead to severe impairments in proinflammatory cytokine production induced by cross-linking of high-affinity IgE receptor on mast cells. By using an in vitro assay to measure the activity that blocks the interaction between protein kinase C and the pleckstrin homology domain of Btk, terreic acid (TA) was identified and characterized in this study. This quinone epoxide specifically inhibited the enzymatic activity of Btk in mast cells and cell-free assays. TA faithfully recapitulated the phenotypic defects of btk mutant mast cells in high-affinity IgE receptor-stimulated wild-type mast cells without affecting the enzymatic activities and expressions of many other signaling molecules, including those of protein kinase C. Therefore, this study confirmed the important roles of Btk in mast cell functions and showed the usefulness of TA in probing into the functions of Btk in mast cells and other immune cell systems. Another insight obtained from this study is that the screening method used to identify TA is a useful approach to finding more efficacious Btk inhibitors.

  9. A simple solubility tests for the discrimination of acrylic and modacrylic fibers.

    PubMed

    Suga, Keisuke; Narita, Yuji; Suzuki, Shinichi

    2014-05-01

    In a crime scene investigation, single fibers play an important role as significant trace physical evidence. Acrylic fibers are frequently encountered in forensic analysis. Currently, acrylic and modacrylic are not discriminated clearly in Japan. Only results of FT-IR, some of acrylics were difficult to separate clearly to acrylic and modacrylic fibers. Solubility test is primitive but convenient useful method, and Japan Industrial Standards (JIS) recommends FT-IR and solubility test to distinguish acrylic and modacrylic fibers. But recommended JIS dissolving test using 100% N,N-dimethylformamide (DMF) as a solvent, some acrylics could not be discriminated. In this report, we used DMF and ethanol (90:10, v/v) solvent. The JIS method could not discriminate 6 acrylics in 60 acrylics; hence, DMF and ethanol (90:10, v/v) solvent discriminated 59 of the 60 fibers (43 acrylic and 16 modacrylic fibers) clearly, but only one modacrylic fiber incorrectly identified as acrylic.

  10. Protein Bodies of the Soybean

    PubMed Central

    Tombs, M. P.

    1967-01-01

    Some microscope observations of the protein bodies of the cotyledon cells of the soybean (Glycine max) are described, together with changes in their appearance which occur on germination. Density gradient centrifugation permits the isolation of protein bodies from soymeal. They contain about 70% of the protein of the bean. Only 1 protein could be detected in them: glycinin, the major soybean protein. The protein bodies were fractionated to light and heavy fractions. The former contained 97.5% protein, the latter 78.5%. RNA, phytic acid and lipids were also present. The 2 fractions probably differ only in the extent of contamination by other cell fragments. Images PMID:16656574

  11. [Determination of 9 residual acrylic monomers in acrylic resins by gas chromatography-mass spectrometry coupled with microwave assisted extraction].

    PubMed

    Lai, Ying; Lin, Rui; Cai, Luxin; Ge, Xiuxiu; Huang, Changchun

    2012-01-01

    A reliable gas chromatography-mass spectrometry (GC-MS) method was developed for the determination of 9 residual acrylic monomers (methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, n-butyl acrylate, butyl methacrylate, styrene, acrylic acid and methacrylic acid) in acrylic resins. Solid resin was precipitated with methanol after microwave assisted extraction with ethyl acetate for 30 min, and liquid resin was diluted with methanol directly. The nine acrylic monomers got a good separation within 20 min on a DB-WAX column. The limits of quantification (LOQs, S/N = 10) of the method were in the range of 1-10 mg/kg for liquid resin and 3-50 mg/kg for solid resin. The calibration curves were linear within 1-500 mg/L range with correlation coefficients above 0. 995. The recoveries ranged from 84.4% to 108.6% at five spiked levels. The sensitivity, recovery and selectivity of the method can fully meet the requirements of practical work.

  12. [Transgenic technology and soybean quality improvement].

    PubMed

    Cheng, Hao; Jin, Hang-Xia; Gai, Jun-Yi; Yu, De-Yue

    2011-05-01

    Soybean is an important source of edible oil, protein and protein diet. The breeding process of high quality soybean can be accelerated via employment of transgenic technology, by which the key genes for soybean quality traits could be directly manipulated. Thus, various soybean varieties could be bred to fulfill different needs for specific consumers. Here, we reviewed the contribution of transgenic technology to improvement of soybean qualities in recent years. We also introduce some newly developed safe transgenic technologies and hope this information could relieve some concerns on the GM food.

  13. Effects of selective genetic introgression from wild soybean to soybean

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Commercial soybean [Glycine max (L.) Merr.] breeding in the U.S. currently relies on a narrow genetic base in which more than half of the genetic contribution, calculated by pedigree analysis, comes from only 5 ancestral lines. For decades, but more intensely in recent years, efforts have been made ...

  14. Mutagenic and cell-transforming activities of triol-epoxides as compared to other chrysene metabolites.

    PubMed

    Glatt, H; Seidel, A; Bochnitschek, W; Marquardt, H; Marquardt, H; Hodgson, R M; Grover, P L; Oesch, F

    1986-09-01

    The syn- and anti-isomers of the bay-region diol-epoxides of chrysene and of 3-hydroxychrysene and their metabolic precursors have been investigated for mutagenicity in Salmonella typhimurium (reversion to histidine prototrophy) and V79 Chinese hamster cells (acquirement of resistance to 6-thioguanine) and for transforming activity in M2 mouse prostate cells. Other known and potential chrysene metabolites have been included in mutagenicity experiments. Direct mutagenic activity in S. typhimurium TA 100 exhibited, in order of potency, anti-triol-epoxide greater than syn-triol-epoxide greater than anti-diol-epoxide greater than syn-diol-epoxide greater than chrysene 5,6-oxide much greater than chrysene-1,2-quinone, chrysene-3,4-quinone, and chrysene 5,6-quinone. Chrysene, the six isomeric chrysenols, and the trans-dihydrodiols [trans-1,2-dihydroxy-1,2-dihydrochrysene (chrysene-1,2-diol), trans-3,4-dihydroxy-3,4-dihydrochrysene, trans-5,6-dihydroxy-5,6-dihydrochrysene, and 9-hydroxy-trans-1,2-dihydroxy-1,2-dihydrochrysene (9-hydroxychrysene-1,2-diol)] were inactive per se but were activated to mutagens in the presence of reduced nicotinamide adenine dinucleotide phosphate-fortified postmitochondrial fraction (S9 mix) of liver homogenate from Arochlor 1254-treated rats. Chrysene, 3-hydroxychrysene, chrysene-1,2-diol, and 9-hydroxychrysene-1,2-diol were activated efficiently; the other compounds were activated weakly. In S. typhimurium TA 98, the mutagenic activities of the chrysene derivatives were weak in comparison with those in the strain TA 100. trans-3,4-Dihydroxy-3,4-dihydrochrysene (in the presence of S9 mix) was the most efficacious mutagen in strain TA 98. The relative mutagenic potencies of the directly active compounds differed from the results obtained in strain TA 100, in that in strain TA 98 the anti-diol-epoxide was more mutagenic than the triol-epoxides and chrysene 5,6-oxide was more mutagenic than syn-diol-epoxide and syn-triol-epoxide. In V79 cells

  15. Metatungstate and tungstoniobate-containing LDHs: Preparation, characterisation and activity in epoxidation of cyclooctene

    NASA Astrophysics Data System (ADS)

    Carriazo, D.; Lima, S.; Martín, C.; Pillinger, M.; Valente, A. A.; Rives, V.

    2007-10-01

    Polyoxometalates (POMs) H2W12O406- and W4Nb2O194- have been intercalated between the brucite-like layers of Mg, Al and Zn, Al hydrotalcites by anion exchange, starting from the corresponding nitrate precursors. The solids have been characterised by Powder X-ray Diffraction (PXRD), Fourier Transform infrared (FT-IR) spectroscopy, N2 adsorption desorption at -196 °C and thermogravimetric (TG) and differential thermal analyses (DTA), and have been tested in the epoxidation of cyclooctene using H2O2 or t-BuOOH as oxidants. The results show that both anions are effectively located in the interlayer space maintaining their pristine structures without depolymerisation. Upon intercalation of such large anions microporosity is developed and subsequently an increase in the specific surface areas is also observed. In general, the prepared materials possess catalase and epoxidation activity, with ZnAl-intercalated H2W12O406- giving the best results in terms of epoxide yield (17% at 24 h). Product selectivity is different for the intercalated and free POMs, the latter yielding 1,2-cyclooctanediol as the only product, whereas the former produces only the epoxide. The epoxidation reaction seems to be catalysed in homogeneous phase by the POM.

  16. Synthesis and physicochemical properties of epoxidized Tmp trioleate by in situ method

    SciTech Connect

    Samidin, Salma; Salimon, Jumat

    2014-09-03

    Tmp trioleate was initially synthesized via esterification of trimetilolprapane and oleic acid (90%) using 1.5% of H{sub 2}SO{sub 4} as a catalyst. The production of Tmp trioleate was observed at 98% (w/w). The iodine value of Tmp trioleate was analyzed for further reaction of epoxidation. Epoxide was important reaction as an intermediate for preparation of chemical modified lubricants from vegetable oils. Finding the best way of epoxidation process will give high quality for further modification of oil instead of reduce the cost and time for the preparation process during reaction of epoxidation. In this study, the epoxidation of unsaturation Tmp trioleate with peroxyformic acid generated in-situ from hydrogen peroxide 30% in H{sub 2}O{sub 2} with formic acid was studied. 95% conversion to oxygen oxirane content (OOC) ring was obtained. The derivatization showed an improvement of the compound's oxidative stability evidenced from pressurized differential scanning calorimetry (PDSC) data which are 177°C to 200°C. Physicochemical properties showed increasing of temperature of flash point from 280°C to 300°C and viscosity index (VI) from 146 to 154. However, the pour point showed increasing temperature which was −58.81°C to −17.32°C. From the data obtained, these derivatives have shown better performance of lubricity properties. Overall, the data indicates that these performances are compatible to the commercial lubricants.

  17. Synthesis and physicochemical properties of epoxidized Tmp trioleate by in situ method

    NASA Astrophysics Data System (ADS)

    Samidin, Salma; Salimon, Jumat

    2014-09-01

    Tmp trioleate was initially synthesized via esterification of trimetilolprapane and oleic acid (90%) using 1.5% of H2SO4 as a catalyst. The production of Tmp trioleate was observed at 98% (w/w). The iodine value of Tmp trioleate was analyzed for further reaction of epoxidation. Epoxide was important reaction as an intermediate for preparation of chemical modified lubricants from vegetable oils. Finding the best way of epoxidation process will give high quality for further modification of oil instead of reduce the cost and time for the preparation process during reaction of epoxidation. In this study, the epoxidation of unsaturation Tmp trioleate with peroxyformic acid generated in-situ from hydrogen peroxide 30% in H2O2 with formic acid was studied. 95% conversion to oxygen oxirane content (OOC) ring was obtained. The derivatization showed an improvement of the compound's oxidative stability evidenced from pressurized differential scanning calorimetry (PDSC) data which are 177°C to 200°C. Physicochemical properties showed increasing of temperature of flash point from 280°C to 300°C and viscosity index (VI) from 146 to 154. However, the pour point showed increasing temperature which was -58.81°C to -17.32°C. From the data obtained, these derivatives have shown better performance of lubricity properties. Overall, the data indicates that these performances are compatible to the commercial lubricants.

  18. [Treatment of acrylate wastewater by electrocatalytic reduction process].

    PubMed

    Yu, Li-Na; Song, Yu-Dong; Zhou, Yue-Xi; Zhu, Shu-Quan; Zheng, Sheng-Zhi; Ll, Si-Min

    2011-10-01

    High-concentration acrylate wastewater was treated by an electrocatalytic reduction process. The effects of the cation exchange membrane (CEM) and cathode materials on acrylate reduction were investigated. It indicated that the acrylate could be reduced to propionate acid efficiently by the electrocatalytic reduction process. The addition of CEM to separator with the cathode and anode could significantly improve current efficiency. The cathode materials had significant effect on the reduction of acrylate. The current efficiency by Pd/Nickel foam, was greater than 90%, while those by nickel foam, the carbon fibers and the stainless steel decreased successively. Toxicity of the wastewater decreased considerably and methane production rate in the biochemical methane potential (BMP) test increased greatly after the electrocatalytic reduction process.

  19. Use of acrylic sheet molds for elastomeric products

    NASA Technical Reports Server (NTRS)

    Heisman, R. M.; Koerner, A. E.; Messineo, S. M.

    1970-01-01

    Molds constructed of acrylic sheet are more easily machined than metal, are transparent to ensure complete filling during injection, and have smooth surfaces free of contamination. Technique eliminates flashing on molded parts and mold release agents.

  20. Performance behavior of modified cellulosic fabrics using polyurethane acrylate copolymer.

    PubMed

    Zuber, Mohammad; Shah, Sayyed Asim Ali; Jamil, Tahir; Asghar, Muhammad Irfan

    2014-06-01

    The surface of the cellulosic fabrics was modified using self-prepared emulsions of polyurethane acrylate copolymers (PUACs). PUACs were prepared by varying the molecular weight of polycaprolactone diol (PCL). The PCL was reacted with isophorone diisocyanate (IPDI) and chain was extended with 2-hydroxy ethyl acrylate (HEA) to form vinyl terminated polyurethane (VTPU) preploymer. The VTPU was further co-polymerized through free radical polymerization with butyl acrylate in different proportions. The FT-IR spectra of monomers, prepolymers and copolymers assured the formation of proposed PUACs structure. The various concentrations of prepared PUACs were applied onto the different fabric samples using dip-padding techniques. The results revealed that the application of polyurethane butyl acrylate copolymer showed a pronounced effect on the tear strength and pilling resistance of the treated fabrics.

  1. Emulsion Polymerization of Butyl Acrylate: Spin Trapping and EPR Study

    NASA Technical Reports Server (NTRS)

    Kim, S.; Westmoreland, D.

    1994-01-01

    The propagating radical in the emulsion polymerization reaction of butyl acrylate was detected by Electron Paramagnetic Resonance spectroscopy using two spin trapping agents, 2-methyl-2nitrosopropane and alpha -N-tert-butylnitrone.

  2. PERMEATION OF MULTIFUNCTIONAL ACRYLATES THROUGH SELECTED PROTECTIVE GLOVE MATERIALS

    EPA Science Inventory

    In support of the Premanufacture Notification (PMN) program of the Environmental Protection Agency's Office of Toxic Substances, the resistance of three glove materials to permeation by multifunctional acrylate compounds was evaluated through a program for the Office of Research ...

  3. Quaternary ammonium salt containing soybean oil: an efficient nanosize gene delivery carrier for halophile green microalgal transformation.

    PubMed

    Akbari, Fariba; Yari Khosroushahi, Ahmad; Yeganeh, Hamid

    2015-01-01

    Dunaliella salina, a halophile green microalga, is considered a robust photobioreactor and a remarkable cost beneficial system for the production of therapeutic recombinant proteins. In this study, with low overall cost, a proper cationic lipid was synthesized from renewable soybean oil as an efficient gene delivery carrier for D. salina cells to create appropriate protein-producing transformed cell lines. To obtain an effective carrier, quaternary ammonium salt containing soybean oil (QASSO) was synthesized through the ring opening reaction of the epoxy groups of epoxidized soybean oil with diethylamine. QASSO was characterized using nuclear magnetic resonance and Fourier-transform infrared instruments. QASSO was used to prepare nanolipoplex construct using plasmid DNA molecules containing green fluorescent protein (GFP) as reporter gene. These nanolipoplexes (QASSO-pGFP, N/P=3) and QASSO had diameter of 63.62 and 110.63 nm, and zeta potential of -68.89 and 48.25 mV at pH 7.0, respectively. Results indicated the GFP gene expression and cytoplasmic accumulation of GFP protein in the transformants after incubation under desirable conditions for 48 h and 1 week. The transformation efficiency was quantitatively assayed by flow cytometry, which yielded transformations of 58.87% and 48.34% for QASSO and 38.32% and a negligible percentage for Polyfect® after 48 h and 1 week incubation, respectively.

  4. Synthesis and evaluation of antibacterial polyurethane coatings made from soybean oil functionalized with dimethylphenylammonium iodide and hydroxyl groups.

    PubMed

    Bakhshi, Hadi; Yeganeh, Hamid; Mehdipour-Ataei, Shahram

    2013-06-01

    Preparation of antibacterial polyurethane coatings from novel functional soybean oil was considered in this work. First, epoxidized soybean oil (ESBO) as a low price and widely available renewable resource raw material was subjected to the reaction with aniline using an ionic liquid as a green catalyst. The intermediate phenylamine containing polyol (SAP) was then methylated by reaction with methyl iodide to produce a polyol (QAP) with pendant dimethylphenylammonium iodide groups. To regulate the physical and mechanical properties as well as biological characteristics of final coatings, QAP was mixed with different portions of a similar soybean oil-based polyol (MSP) without quaternary ammonium groups. The mixtures were reacted with isophorone diisocyanate to produce crosslinked polyurethane coatings. Evaluation of viscoelastic properties by DMA method revealed single phase structure with Tg in the range of 50-82°C. Stress-strain analysis of the prepared polyurethanes showed initial modulus, tensile strength, and elongation at break in the ranges of 13-299 MPa, 4.5-13.8 MPa, and 16-109%, respectively. Additionally, the coatings showed good adherence to aluminum and PVC substrates. The solvent extracted samples showed excellent biocompatibility as determined by monitoring L929 fibroblast cells morphology and MTT assay. Meanwhile, very promising antibacterial properties against both Gram-positive (S. aureus) and Gram-negative (E. coli) bacteria with bacterial reduction in the range of 83-100% was observed. PMID:23172859

  5. Archaeophytopathology of Global Soybean Rust

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phakopsora pachyrhizi and P. meibomiae are two rust species that infect soybean (Glycine max). A number of other hosts support the uredinial growth of these Phakopsora, including Pachyrhizus erosus, Pueraria lobata, and Vigna unguiculata, but no aecial host is known. Traditionally, these two species...

  6. Agriculture Education. Soybeans and Rice.

    ERIC Educational Resources Information Center

    Stuttgart Public Schools, AR.

    This curriculum guide is designed for group instruction of secondary students enrolled in one or two semester-long courses in agricultural education. The guide presents units of study in the following areas: (1) soybeans, (2) rice, and (3) orientation. Each of the 17 units of instruction follows a typical format: terminal objective, specific…

  7. Synthesis and characterization of antibacterial polyurethane coatings from quaternary ammonium salts functionalized soybean oil based polyols.

    PubMed

    Bakhshi, Hadi; Yeganeh, Hamid; Mehdipour-Ataei, Shahram; Shokrgozar, Mohammad Ali; Yari, Abbas; Saeedi-Eslami, Seyyed Nasirodin

    2013-01-01

    In this study, a simple and versatile synthetic approach was developed to prepare bactericidal polyurethane coatings. For this purpose, introduction of both quaternary ammonium salts (QASs), with well-known antibacterial activity, and reactive hydroxyl groups on to the backbone of soybean oil was considered. Epoxidized soybean oil was reacted with diethylamine and the intermediate tertiary amine containing polyol was reacted with two different alkylating agents, methyl iodide and benzyl chloride, to produce MQAP and BQAP, respectively. These functional polyols were reacted with different diisocyanate monomers to prepare polyurethane coatings. Depending on the structure of monomers used for the preparation of polyurethane coatings, initial modulus, tensile strength and elongation at break of samples were in the ranges of 122-339 MPa, 4.6-12.4 MPa and 8.4-46%, respectively. Polyurethane coatings based on isophorone diisocyanate showed proper mechanical properties and adhesion strength (0.41 MPa) for coating application. Study of fibroblast cells interaction with prepared polyurethanes showed promising cells viability in the range of 78-108%. Meanwhile, MQAP based samples with higher concentration of QASs showed better adhesion strength, surface hydrophilicity and antibacterial activity (about 95% bacterial reduction). Therefore, these materials can find applications as bactericidal coating for biomedical devices and implants.

  8. Synthesis and characterization of antibacterial polyurethane coatings from quaternary ammonium salts functionalized soybean oil based polyols.

    PubMed

    Bakhshi, Hadi; Yeganeh, Hamid; Mehdipour-Ataei, Shahram; Shokrgozar, Mohammad Ali; Yari, Abbas; Saeedi-Eslami, Seyyed Nasirodin

    2013-01-01

    In this study, a simple and versatile synthetic approach was developed to prepare bactericidal polyurethane coatings. For this purpose, introduction of both quaternary ammonium salts (QASs), with well-known antibacterial activity, and reactive hydroxyl groups on to the backbone of soybean oil was considered. Epoxidized soybean oil was reacted with diethylamine and the intermediate tertiary amine containing polyol was reacted with two different alkylating agents, methyl iodide and benzyl chloride, to produce MQAP and BQAP, respectively. These functional polyols were reacted with different diisocyanate monomers to prepare polyurethane coatings. Depending on the structure of monomers used for the preparation of polyurethane coatings, initial modulus, tensile strength and elongation at break of samples were in the ranges of 122-339 MPa, 4.6-12.4 MPa and 8.4-46%, respectively. Polyurethane coatings based on isophorone diisocyanate showed proper mechanical properties and adhesion strength (0.41 MPa) for coating application. Study of fibroblast cells interaction with prepared polyurethanes showed promising cells viability in the range of 78-108%. Meanwhile, MQAP based samples with higher concentration of QASs showed better adhesion strength, surface hydrophilicity and antibacterial activity (about 95% bacterial reduction). Therefore, these materials can find applications as bactericidal coating for biomedical devices and implants. PMID:25428057

  9. Separation of soybean saponins from soybean meal by a technology of foam fractionation and resin adsorption.

    PubMed

    Jiang, Jianxing; Wu, Zhaoliang; Liu, Wei; Gao, Yanfei; Guo, Shenghao; Kang, Shufang

    2016-05-18

    Foam fractionation and resin adsorption were used to recover soybean saponins from the industrial residue of soybean meal. First, a two-stage foam fractionation technology was studied for concentrating soybean saponins from the leaching liquor. Subsequently, resin adsorption was used to purify soybean saponins from the foamate in foam fractionation. The results showed that the enrichment ratio, the recovery percentage, and the purity of soybean saponins by using the two-stage foam fractionation technology could reach 4.45, 74%, and 67%, respectively. After resin adsorption and desorption, the purity of soybean saponins in the freeze-dried powder from the desorption solution was 88.4%.

  10. A biotechnological approach to the synthesis of epoxides: bioconversion of hydrocarbons by Pseudomonas oleovorans during growth in a multiphase system

    SciTech Connect

    De Smet, M.J.

    1983-04-01

    This communication examines the oxidation of alkanes and alkenes by Pseudomonas oleovorans. A variety of substrates were tested in order to extend the practical use of P. oleovorans for the synthesis of chiral epoxides. Concludes that hydrocarbon fermentations of P. oleovorans might be an important tool not only in the production of epoxides but also in the production of aliphatic polyesters and biosurfactants.

  11. 40 CFR 63.1427 - Process vent requirements for processes using extended cookout as an epoxide emission reduction...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... epoxide in the reactor liquid at the beginning of the time period, weight percent. k = Reaction rate... directly measuring the concentration of the unreacted epoxide, or by using process knowledge, reaction... accordance with paragraph (f)(1)(i) of this section, or reaction kinetics in accordance with paragraph...

  12. [(Salcen)Cr(III) + Lewis base]-catalyzed synthesis of N-aryl-substituted oxazolidinones from epoxides and aryl isocyanates.

    PubMed

    Paddock, Robert L; Adhikari, Debashis; Lord, Richard L; Baik, Mu-Hyun; Nguyen, SonBinh T

    2014-12-14

    [(Salcen)Cr(III) + Lewis base] was found to be a highly active and selective catalyst system in the [2+3] cycloaddition between epoxides and isocyanates to form 5-oxazolidinones. The reaction proceeds to high yield under mild reaction conditions and is applicable to a variety of terminal epoxides and aryl isocyanates.

  13. Highly Selective Olefin Epoxidation with Aqueous H₂O₂ Over Surfacemodified TaSBA15 Prepared via the TMP Method

    SciTech Connect

    Ruddy, Daniel A.; Tilley, T. D.

    2007-07-17

    Trialkylsiloxy-modified Ta(V) centers on mesoporous silica exhibit excellent selectivity for epoxide formation (>98% after 2 h) in the oxidation of cyclohexene using aqueous H₂O₂ as the oxidant; the modified catalysts exhibit an increased lifetime, retaining high selectivity after 6 h of reaction (>95% epoxide).

  14. 40 CFR 63.1427 - Process vent requirements for processes using extended cookout as an epoxide emission reduction...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... at the beginning of the time period, weight percent. k = Reaction rate constant, 1/hr. t = Time... epoxide concentration using 40 CFR part 60, appendix A, Method 18. (ii) Determine the epoxide concentration in the vapor space using Raoult's Law or another appropriate phase equilibrium equation and...

  15. 40 CFR 63.1427 - Process vent requirements for processes using extended cookout as an epoxide emission reduction...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... at the beginning of the time period, weight percent. k = Reaction rate constant, 1/hr. t = Time... epoxide concentration using 40 CFR part 60, appendix A, Method 18. (ii) Determine the epoxide concentration in the vapor space using Raoult's Law or another appropriate phase equilibrium equation and...

  16. Nutritional value of raw soybeans, extruded soybeans, roasted soybeans and tallow as fat sources in early lactating dairy cows

    PubMed Central

    Amanlou, H.; Maheri-Sis, N.; Bassiri, S.; Mirza-Aghazadeh, A.; Salamatdust, R.; Moosavi, A.; Karimi, V.

    2012-01-01

    Thirty multiparous Holstein cows (29.8 ± 4.01days in milk; 671.6 ± 31.47 kg of body weight) were used in a completely randomized design to compare nutritional value of four fat sources including tallow, raw soybeans, extruded soybeans and roasted soybeans for 8 weeks. Experimental diets were a control containing 27.4 % alfalfa silage, 22.5% corn silage, and 50.1% concentrate, and four diets with either tallow, raw soybean, extruded soybean, or roasted soybean added to provide 1.93% supplemental fat. Dry matter and NEL intakes were similar among treatments, while cows fed fat diets had significantly (P<0.05) high NEL intakes when compared to control with no fat. Supplemental fat, whether tallow or full fat soybeans increased milk production (1.89-2.45 kg/d; P<0.01) and FCM production (1.05-2.79; P<0.01). Milk fat yield and percentage of cows fed fat-supplemented diets were significantly (P<0.01 and P<0.05 respectively) higher than control. Between fat-supplemented diets, roasted soybean caused highest milk fat yield and extruded soybean caused lowest milk fat yield. There was no significant effect of supplemental fat on the milk protein and lactose content and yield. Feed efficiency of fat-supplemented diets was significantly (P<0.01) higher than control. Body weight, body weight change and BCS (body condition score) of cows, as well as energy balance and energy efficiency were similar between treatments. In conclusion, while there was no significant effect of fat sources on production response of cows, fat originating from heat-treated soybean help to minimize imported RUP (rumen undegradable protein) sources level as fish meal in comparison with tallow and raw soybean oil. In the Current study, there was no statistical significance among nutritional values of oil from extruded soybeans and roasted soybeans. PMID:26623299

  17. Stabilizing effects of estertins mercaptide (methyl acrylate) for PVC degradation

    NASA Astrophysics Data System (ADS)

    Zhang, S. H.; Liu, T. M.; Li, J. L.; Wang, C. R.; Li, C.; Wang, Z. Q.

    2016-07-01

    The thermal and UV light (ultraviolet light) stability of PVC films with estertins mercaptide (methyl acrylate), methyltins mercaptide and the compound consisted of estertins mercaptide (methyl acrylate) and hydrotalcite (2:2.5) were investigated by ageing in a circulation oven at 190 °C and irradiating with 72W UV light for 96h, respectively, and then the yellowness and transmission rate were tested by Color Quest XE. Hydrotalcite was proved to have good synergies with estertins mercaptide (methyl acrylate) on improving the thermal stability and UV light stability. The retarding effects of the heat stabilizers to PVC degradation were tested by TGA from 50°C to 600°C. The results show that temperature of HCl evolution from PVC film was improved obviously by compounding with estertins mercaptide(methyl acrylate) and hydrotalcite and estertins mercaptide(methyl acrylate) was found to have a better long term stability. Sn4+ consistence of water and seawater in which films before and after UV light irradiation were soaked for 60 days was analyzed by ICP; the results indicate that the Sn4+ consistence from the films with estertins mercaptide(methyl acrylate) as thermal stabilizer was lower than that from the film with methyltins mercaptide. The crosslink moderately by UV irradiation for PVC films can hold back the dissolution of organotin heat stabilizers from PVC products into water and seawater.

  18. A 2014 nationwide survey of the distribution of Soybean mosaic virus (SMV), Soybean yellow mottle mosaic virus (SYMMV) and Soybean yellow common mosaic virus (SYCMV) major viruses in South Korean soybean fields, and changes

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In 2014 symptomatic soybean samples were collected throughout Korea, and were tested for the most important soybean viruses found in Korea, namely Soybean mosaic virus (SMV), Soybean yellow common mosaic virus (SYCMV), and Soybean yellow mottle mosaic virus (SYMMV). SYMMV was most commonly detected,...

  19. Pharmacokinetics: time-dependent changes--autoinduction of carbamazepine epoxidation

    SciTech Connect

    Bertilsson, L.; Tomson, T.; Tybring, G.

    1986-07-01

    Drugs labeled with stable isotopes have been useful to study time-dependent changes in kinetics. Early studies suggested that carbamazepine (CBZ) may induce its own metabolism, but this could not be proved until tetradeuterium-labeled CBZ (CBZ-D4) was synthesized and then given to patients. CBZ-D4 was administered to three children during long-term treatment of epilepsy with CBZ. After 17 to 32 days of treatment, the plasma clearance of CBZ-D4 was doubled, but during the next four months, there was no further increase, indicating that autoinduction was complete within one month. Two patients with chronic alcoholism were treated with CBZ for five days. Half of the first dose of 600 mg was comprised of CBZ-D4. The half-life of this CBZ-D4 dose in the two patients (20 and 26 hr, respectively) was similar to the post-steady-state half-life of CBZ (23 hr in both patients) measured later. A single dose of CBZ given one week after the last maintenance dose had a longer half-life (46 and 45 hr, respectively), which probably is close to the disposition of the drug before starting the treatment with CBZ. This shows that autoinduction of CBZ metabolism was completed during the very first doses of CBZ. Autoinduction also disappeared rapidly after stopping the treatment. We have shown that it is mainly the epoxide-diol pathway that is induced, both during autoinduction and after induction with other antiepileptic agents.

  20. Microbial metabolism of steviol and steviol-16alpha,17-epoxide.

    PubMed

    Yang, Li-Ming; Hsu, Feng-Lin; Chang, Shwu-Fen; Cheng, Juei-Tang; Hsu, Ju-Yin; Hsu, Chung-Yi; Liu, Pan-Chun; Lin, Shwu-Jiuan

    2007-02-01

    Steviol (2) possesses a blood glucose-lowering property. In order to produce potentially more- or less-active, toxic, or inactive metabolites compared to steviol (2), its microbial metabolism was investigated. Incubation of 2 with the microorganisms Bacillus megaterium ATCC 14581, Mucor recurvatus MR 36, and Aspergillus niger BCRC 32720 yielded one new metabolite, ent-7alpha,11beta,13-trihydroxykaur-16-en-19-oic acid (7), together with four known related biotransformation products, ent-7alpha,13-dihydroxykaur-16-en-19-oic acid (3), ent-13-hydroxykaur-16-en-19-alpha-d-glucopyranosyl ester (4), ent-13,16beta,17-trihydroxykauran-19-oic acid (5), and ent-13-hydroxy-7-ketokaur-16-en-19-oic acid (6). The preliminary testing of antihyperglycemic effects showed that 5 was more potent than the parent compound (2). Thus, the microbial metabolism of steviol-16alpha,17-epoxide (8) with M. recurvatus MR 36 was continued to produce higher amounts of 5 for future study of its action mechanism. Preparative-scale fermentation of 8 yielded 5, ent-11alpha,13,16alpha,17-tetrahydroxykauran-19-oic acid (10), ent-1beta,17-dihydroxy-16-ketobeyeran-19-oic acid (11), and ent-7alpha,17-dihydroxy-16-ketobeyeran-19-oic acid (13), together with three new metabolites: ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid (9), ent-11beta,13-dihydroxy-16beta,17-epoxykauran-19-oic acid (12), and ent-11beta,13,16beta,17-tetrahydroxykauran-19-oic acid (14). The structures of the compounds were fully elucidated using 1D and 2D NMR spectroscopic techniques, as well as HRFABMS. In addition, a GRE (glucocorticoid responsive element)-mediated luciferase reporter assay was used to initially screen the compounds 3-5, and 7 as glucocorticoid agonists. Compounds 4, 5 and 7 showed significant effects. PMID:17207824

  1. Naphthalene cytotoxicity in microsomal epoxide hydrolase deficient mice.

    PubMed

    Carratt, S A; Morin, D; Buckpitt, A R; Edwards, P C; Van Winkle, L S

    2016-03-30

    Naphthalene (NA) is a ubiquitous pollutant to which humans are widely exposed. 1,2-Dihydro-1,2-dihydroxynaphthalene (NA-dihydrodiol) is a major metabolite of NA generated by microsomal epoxide hydrolase (mEH). To investigate the role of the NA-dihydrodiol and subsequent metabolites (i.e. 1,2-naphthoquinone) in cytotoxicity, we exposed both male and female wild type (WT) and mEH null mice (KO) to NA by inhalation (5, 10, 20 ppm for 4h). NA-dihydrodiol was ablated in the KO mice. High-resolution histopathology was used to study site-specific cytotoxicity, and formation of naphthalene metabolites was measured by HPLC in microdissected airways. Swollen and vacuolated airway epithelial cells were observed in the intra- and extrapulmonary airways of all mice at and below the current OSHA standard (10 ppm). Female mice may be more susceptible to this acute cytotoxicity. In the extrapulmonary airways, WT mice were more susceptible to damage than KO mice, indicating that the metabolites associated with mEH-mediated metabolism could be partially responsible for cytotoxicity at this site. The level of cytotoxicity in the mEH KO mice at all airway levels suggests that non-mEH metabolites are contributing to NA cellular damage in the lung. Our results indicate that the apparent contribution of mEH-dependent metabolites to toxicity differs by location in the lung. These studies suggest that metabolites generated through the mEH pathway may be of minor importance in distal airway toxicity and subsequent carcinogenesis from NA exposure.

  2. A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions

    PubMed Central

    White, David E.; Tadross, Pamela M.; Lu, Zhe

    2014-01-01

    The (salen) Co catalyst (4a) can be prepared as a mixture of cyclic oligomers in a short, chromatography-free synthesis from inexpensive, commercially available precursors. This catalyst displays remarkable enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen) Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of water and carbamates; and the desymmetrization of oxetanes by intramolecular ring opening with alcohols and phenols. The favorable solubility properties of complex 4a under the catalytic conditions facilitated mechanistic studies, allowing elucidation of the basis for the beneficial effect of oligomerization. Finally, a catalyst selection guide is provided to delineate the specific advantages of oligomeric catalyst 4a relative to (salen) Co monomer 1 for each reaction class. PMID:25045188

  3. Inhibiting an Epoxide Hydrolase Virulence Factor from Pseudomonas aeruginosa Protects CFTR.

    PubMed

    Bahl, Christopher D; Hvorecny, Kelli L; Bomberger, Jennifer M; Stanton, Bruce A; Hammock, Bruce D; Morisseau, Christophe; Madden, Dean R

    2015-08-17

    Opportunistic pathogens exploit diverse strategies to sabotage host defenses. Pseudomonas aeruginosa secretes the CFTR inhibitory factor Cif and thus triggers loss of CFTR, an ion channel required for airway mucociliary defense. However, the mechanism of action of Cif has remained unclear. It catalyzes epoxide hydrolysis, but there is no known role for natural epoxides in CFTR regulation. It was demonstrated that the hydrolase activity of Cif is strictly required for its effects on CFTR. A small-molecule inhibitor that protects this key component of the mucociliary defense system was also uncovered. These results provide a basis for targeting the distinctive virulence chemistry of Cif and suggest an unanticipated role of physiological epoxides in intracellular protein trafficking. PMID:26136396

  4. Increased silver activity for direct propylene epoxidation via subnanometer size effects.

    PubMed

    Lei, Y; Mehmood, F; Lee, S; Greeley, J; Lee, B; Seifert, S; Winans, R E; Elam, J W; Meyer, R J; Redfern, P C; Teschner, D; Schlögl, R; Pellin, M J; Curtiss, L A; Vajda, S

    2010-04-01

    Production of the industrial chemical propylene oxide is energy-intensive and environmentally unfriendly. Catalysts based on bulk silver surfaces with direct propylene epoxidation by molecular oxygen have not resolved these problems because of substantial formation of carbon dioxide. We found that unpromoted, size-selected Ag3 clusters and approximately 3.5-nanometer Ag nanoparticles on alumina supports can catalyze this reaction with only a negligible amount of carbon dioxide formation and with high activity at low temperatures. Density functional calculations show that, relative to extended silver surfaces, oxidized silver trimers are more active and selective for epoxidation because of the open-shell nature of their electronic structure. The results suggest that new architectures based on ultrasmall silver particles may provide highly efficient catalysts for propylene epoxidation. PMID:20378815

  5. Increased Silver Activity for Direct Propylene Epoxidation via Subnanometer Size Effects

    SciTech Connect

    Lei, Y.; Mehmood, Faisal; Lee, Sang Soo; Greeley, Jeffrey P.; Lee, Byeongdu; Seifert, Soenke; Winans, R. E.; Elam, J. W.; Meyer, R. J.; Redfern, Paul C.; Teschner, D.; Schlogl, Robert; Pellin, M. J.; Curtiss, Larry A.; Vajda, S.

    2010-04-09

    Production of the industrial chemical propylene oxide is energy-intensive and environmentally unfriendly. Catalysts based on bulk silver surfaces with direct propylene epoxidation by molecular oxygen have not resolved these problems because of substantial formation of carbon dioxide. We found that unpromoted, size-selected Ag3 clusters and ~3.5-nanometer Ag nanoparticles on alumina supports can catalyze this reaction with only a negligible amount of carbon dioxide formation and with high activity at low temperatures. Density functional calculations show that, relative to extended silver surfaces, oxidized silver trimers are more active and selective for epoxidation because of the open-shell nature of their electronic structure. The results suggest that new architectures based on ultrasmall silver particles may provide highly efficient catalysts for propylene epoxidation.

  6. Increased silver activity for direct propylene epoxidation via subnanometer size effects.

    SciTech Connect

    Lei, Y.; Mehmood, F.; Lee, S.; Greeley, J. P.; Lee, B.; Seifert, S.; Winans, R. E.; Elam, J. E.; Meyer, R. J.; Redfern, P. C.; Teschner, D.; Schlogl, R.; Pellin, M. J.; Curtiss, L. A.; Vajda, S.; Univ. of Illinois at Chicago; Fritz-Haber Inst. der Max-Planck-Gesellschaft; Yale Univ.

    2010-04-09

    Production of the industrial chemical propylene oxide is energy-intensive and environmentally unfriendly. Catalysts based on bulk silver surfaces with direct propylene epoxidation by molecular oxygen have not resolved these problems because of substantial formation of carbon dioxide. We found that unpromoted, size-selected Ag{sub 3} clusters and {approx}3.5-nanometer Ag nanoparticles on alumina supports can catalyze this reaction with only a negligible amount of carbon dioxide formation and with high activity at low temperatures. Density functional calculations show that, relative to extended silver surfaces, oxidized silver trimers are more active and selective for epoxidation because of the open-shell nature of their electronic structure. The results suggest that new architectures based on ultrasmall silver particles may provide highly efficient catalysts for propylene epoxidation.

  7. Epoxidized natural rubber toughened aqueous resole type liquefied EFB resin: Physical and chemical characterization

    NASA Astrophysics Data System (ADS)

    Amran, Umar Adli; Zakaria, Sarani; Chia, Chin Hua

    2013-11-01

    A preliminary study on the reaction between aqueous resole type resinified liquefied palm oil empty fruit bunches fibres (RLEFB) with epoxidized natural rubber (ENR). Liquefaction of empty fruit bunches (EFB) is carried out at different ratio of phenol to EFB (P:EFB). Resole type phenolic resin is prepared using sodium hydroxide (NaOH) as the catalyst with the ratio of liquefied EFB (LEFB) to formaldehyde (LEFB:F) of 1:1.8. 50% epoxidation of epoxidized natural rubber (ENR-50) is used to react with resole resin by mixing with ENR with aqueous resole resin. The cured resin is characterized with FT-IR and SEM. Aqueous system have been found to be unsuitable medium in the reaction between resin and ENR. This system produced a highly porous product when RLEFB/ENR resin is cured.

  8. Synthesis of Marine Polycyclic Polyethers via Endo-Selective Epoxide-Opening Cascades

    PubMed Central

    Vilotijevic, Ivan; Jamison, Timothy F.

    2010-01-01

    The proposed biosynthetic pathways to ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share a dramatic epoxide-opening cascade as a key step. Polycyclic structures generated in these biosynthetic pathways display biological effects ranging from potentially therapeutic properties to extreme lethality. Much of the structural complexity of ladder polyether and oxasqualenoid natural products can be traced to these hypothesized cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of ladder polyethers and oxasqualenoid natural products. PMID:20411125

  9. Zirconium(IV)- and hafnium(IV)-catalyzed highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols.

    PubMed

    Li, Zhi; Yamamoto, Hisashi

    2010-06-16

    In this report, zirconium(IV)- and hafnium(IV)-bishydroxamic acid complexes were utilized in the highly enantioselective epoxidation of homoallylic alcohols and bishomoallylic alcohols, which used to be quite difficult substrates for other types of asymmetric epoxidation reactions. The performance of the catalyst was improved by adding polar additive and molecular sieves. For homoallylic alcohols, the reaction could provide epoxy alcohols in up to 83% yield and up to 98% ee, while, for bishomoallylic alcohols, up to 79% yield and 99% ee of epoxy alcohols rather than cyclized tetrahydrofuran compounds could be obtained in most cases.

  10. The selection reaction of homogeneous catalyst in soy-epoxide hydroxylation

    NASA Astrophysics Data System (ADS)

    Elvistia Firdaus, Flora

    2014-04-01

    Hydroxylation reaction of soy-epoxide has resulted soy-polyol; a prepolymeric material for polyurethane. The conversion and selectivity of soy-epoxide butanol based to hydroxylation was found higher than soy-ethylene glycol (EG) based. These reactions were performed by sulfur acid which commonly known as homogeneous catalyst. Conversion and selectivity of homogeneous catalyst compared to bentonite; a heteregeneous catalyst was lower as in fact the mixtures were more viscous. The catalysis were significantly effected to cell morphology. Foams were conducted by heterogeneous catalyst resulted an irregular form of windows while homogeneous catalyst are more ordered.

  11. Asymmetric epoxidation of allylic alcohols catalyzed by vanadium-binaphthylbishydroxamic Acid complex.

    PubMed

    Noji, Masahiro; Kobayashi, Toshihiro; Uechi, Yuria; Kikuchi, Asami; Kondo, Hisako; Sugiyama, Shigeo; Ishii, Keitaro

    2015-03-20

    A vanadium-binaphthylbishydroxamic acid (BBHA) complex-catalyzed asymmetric epoxidation of allylic alcohols is described. The optically active binaphthyl-based ligands BBHA 2a and 2b were synthesized from (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid and N-substituted-O-trimethylsilyl (TMS)-protected hydroxylamines via a one-pot, three-step procedure. The epoxidations of 2,3,3-trisubstituted allylic alcohols using the vanadium complex of 2a were easily performed in toluene with a TBHP water solution to afford (2R)-epoxy alcohols in good to excellent enantioselectivities.

  12. Regioselective and Stereospecific Copper-Catalyzed Deoxygenation of Epoxides to Alkenes.

    PubMed

    Yu, Jingxun; Zhou, Yu; Lin, Zhenyang; Tong, Rongbiao

    2016-09-16

    Two copper salts (Cu(CF3CO2)2 and IMesCuCl) were identified as earth-abundant, inexpensive, but effective metal catalysts together with diazo malonate for chemo-/regioselective and stereospecific deoxygenation of various epoxides with tolerance of common functional groups (alkene, ketone, ester, p-methoxybenzyl, benzyl, tert-butyldimethylsilyl, and triisopropylsilyl). In particular, the unprecedented regioselectivity allowed for the first time monodeoxygenation of diepoxides to alkenyl epoxides. Density functional theory mechanistic studies showed that the deoxygenation occurred by collapsing the free ylide, unfavoring the possible intuitive pathway via cycloreversion of possible oxetane. PMID:27596225

  13. Microsomal Epoxide Hydrolase 1 (EPHX1): Gene, Structure, Function, and Role in Human Disease

    PubMed Central

    Václavíková, Radka; Hughes, David J; Souček, Pavel

    2015-01-01

    Microsomal epoxide hydrolase (EPHX1) is an evolutionarily highly conserved biotransformation enzyme for converting epoxides to diols. Notably, the enzyme is able to either detoxify or bioactivate a wide range of substrates. Mutations and polymorphic variants in the EPHX1 gene have been associated with susceptibility to several human diseases including cancer. This review summarizes the key knowledge concerning EPHX1 gene and protein structure, expression pattern and regulation, and substrate specificity. The relevance of EPHX1 for human pathology is especially discussed. PMID:26216302

  14. Green chemistry: Efficient epoxides ring-opening with 1-butanol under microwave irradiation

    NASA Astrophysics Data System (ADS)

    García-Vidal, Jesús A.; Durán-Valle, Carlos J.; Ferrera-Escudero, Santiago

    2006-06-01

    Two activated carbons treated with mineral acids (HNO 3 and sulfonitric mixture) have been tested as acid catalysts in the epoxides (1,2-epoxyhexane and styrene oxide) ring-opening reaction with 1-butanol under microwave (MW) irradiation. The mayor obtained product is that resulting of the alcohol addition to the most substituted carbon in the epoxide ring. The most active catalyst is that treated with sulfonitric mixture. The use of a MW oven allows achieving to the complete conversion of styrene oxide in only 2 min.

  15. Analysis of emulsion stability in acrylic dispersions

    NASA Astrophysics Data System (ADS)

    Ahuja, Suresh

    2012-02-01

    Emulsions either micro or nano permit transport or solubilization of hydrophobic substances within a water-based phase. Different methods have been introduced at laboratory and industrial scales: mechanical stirring, high-pressure homogenization, or ultrasonics. In digital imaging, toners may be formed by aggregating a colorant with a latex polymer formed by batch or semi-continuous emulsion polymerization. Latex emulsions are prepared by making a monomer emulsion with monomer like Beta-carboxy ethyl acrylate (β-CEA) and stirring at high speed with an anionic surfactant like branched sodium dodecyl benzene sulfonates , aqueous solution until an emulsion is formed. Initiator for emulsion polymerization is 2-2'- azobis isobutyramide dehydrate with chain transfer agent are used to make the latex. If the latex emulsion is unstable, the resulting latexes produce a toner with larger particle size, broader particle size distribution with relatively higher latex sedimentation, and broader molecular weight distribution. Oswald ripening and coalescence cause droplet size to increase and can result in destabilization of emulsions. Shear thinning and elasticity of emulsions are applied to determine emulsion stability.

  16. Fracture properties of an acrylic bone cement.

    PubMed

    Bialoblocka-Juszczyk, E; Baleani, M; Cristofolini, L; Viceconti, M

    2008-01-01

    This study investigated experimentally the fracture properties, i.e., the fatigue strength, the resistance to crack propagation and the fracture toughness, of an acrylic bone cement (Cemex RX). The mean endurance limit was determined following the staircase method. The endurance limit was estimated at 9.2 MPa. The fatigue crack propagation rate was measured according to the ASTM E647 standard. The equation of the line fitting the crack growth per cycle (da/dN) versus the stress-intensity factor range (delta K), in a log-log graph, was used to calculate the empirical constants of Paris' law for the selected bone cement: da/dN (m/cycle) = 3.56 x 10(-7) x delta K (MPa x m1/2)5.79. This power-law relationship described well (R2 = 0.96) the growth rate in the stable crack growth region, i.e., in the mid delta K range. The fracture toughness K(IC) of the bone cement was determined according to the ASTM E399 standard. The K(IC) mean value was 1.38 MPa x m1/2. These experimental results provide the set of necessary inputs for numerical studies aimed to investigate the damage accumulation process in the mantle fixing cemented prostheses.

  17. Acrylate ester-based monolithic columns for capillary electrochromatography separation of triacylglycerols in vegetable oils.

    PubMed

    Lerma-García, M J; Vergara-Barberán, M; Herrero-Martínez, J M; Simó-Alfonso, E F

    2011-10-21

    A simple and reliable method for the evaluation of triacylglycerols (TAGs) in vegetable oils by capillary electrochromatography (CEC) with UV-Vis detection, using octadecyl acrylate (ODA) ester-based monolithic columns, has been developed. The percentages of the porogenic solvents in the polymerization mixture, and the mobile phase composition, were optimized. The optimum monolith was obtained at the following ratios: 40:60% (wt/wt) monomers/porogens, 60:40% (wt/wt) ODA/1,3-butanediol diacrylate and 23:77% (wt/wt) 1,4-butanediol/1-propanol (14 wt% 1,4-butanediol in the polymerization mixture). A satisfactory resolution between TAGs was achieved in less than 12 min with a 65:35 (v/v) acetonitrile/2-propanol mixture containing 5 mM ammonium acetate. The method was applied to the analysis of TAGs of vegetable oil samples. Using linear discriminant analysis of the CEC TAG profiles, the vegetable oils belonging to six different botanical origins (corn, extra virgin olive, hazelnut, peanut, soybean and sunflower) were correctly classified with an excellent resolution among all the categories.

  18. Artificial Selection for Determinate Growth Habit in Soybean

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Determinacy is an agronomically important trait associated with the domestication in soybean (Glycine max). Most soybean cultivars are classifiable into indeterminate and determinate growth habit, while Glycine soja, the wild progenitor of soybean, is indeterminate. Indeterminate (Dt1) and determina...

  19. Effect of curing cycle on the tensile strength of the bond between heat cured denture base acrylic resin and acrylic resin denture teeth.

    PubMed

    Dalal, Ayesha; Juszczyk, Andrzej S; Radford, David R; Clark, Robert K F

    2009-12-01

    The effect of different curing cycles on the tensile strength of the bond between one brand of cross-linked acrylic resin teeth and three heat cured denture base acrylic resins was tested. There were differences in the tensile bond strength between the three heat cured denture base acrylic resins and the three curing cycles used. The bond strength of the acrylic resin denture base material made by the same manufacturer as the cross-linked acrylic resin denture teeth was higher. The bond strength following the short cycle was lowest in all cases, individual differences between curing cycles failed to reach statistical significance. PMID:20158054

  20. Inhibition of insect juvenile hormone epoxide hydrolase: asymmetric synthesis and assay of glycidol-ester and epoxy-ester inhibitors of trichoplusia ni epoxide hydrolase.

    PubMed

    Linderman, R J; Roe, R M; Harris, S V; Thompson, D M

    2000-01-01

    Juvenile hormone (JH) undergoes metabolic degradation by two major pathways involving JH esterase and JH epoxide hydrolase (EH). While considerable effort has been focussed on the study of JH esterase and the development of inhibitors for this enzyme, much less has been reported on the study of JH-EH. In this work, the asymmetric synthesis of two classes of inhibitors of recombinant JH-EH from Trichoplusia ni, a glycidol-ester series and an epoxy-ester series is reported. The most effective glycidol-ester inhibitor, compound 1, exhibited an I(50) of 1.2x10(-8) M, and the most effective epoxy-ester inhibitor, compound 11, exhibited an I(50) of 9.4x10(-8) M. The potency of the inhibitors was found to be dependent on the absolute configuration of the epoxide. In both series of inhibitors, the C-10 R-configuration was found to be significantly more potent that the corresponding C-10 S-configuration. A mechanism for epoxide hydration catalyzed by insect EH is also presented.

  1. Overexpression of a soybean salicylic acid methlyltransferase gene confers resistance to soybean cyst nematode

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean cyst nematode (Heterodera glycines Ichinohe, SCN) is the most pervasive pest of soybean [Glycine max (L.) Merr.] in the USA and worldwide. SCN reduced soybean yields worldwide by an estimated billion dollars annually. These losses remained stable with the use of resistant cultivars but over ...

  2. Identification and molecular mapping of two soybean aphid resistance genes in soybean PI 587732

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean [Glycine max (L.) Merr.] continues to be plagued by the soybean aphid (Aphis glycines Matsumura: SA) in North America. New soybean resistance sources are needed to combat the four identified SA biotypes. The objectives of this study were to determine the inheritance of SA resistance in PI 58...

  3. THE SOYBEAN BREEDER'S TOOLBOX: INTEGRATION OF GENETIC AND MOLECULAR DATA FOR SOYBEAN

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean genetic data has been compiled and stored in the soybean genetic database SoyBase. This data has been retrieved from an AceDB database and used to compile a new database called the Soybean Breeder’s Toolbox (SBT). The toolbox is a relational database utilizing the MySQL RDMS. The use of a...

  4. Fine Mapping the Soybean Aphid Resistance Gene Rag1 in Soybean

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The soybean aphid [Aphis glycines Matsumura] is an important soybean [Glycine max (L.) Merr.] pest in North America. The dominant aphid resistance gene Rag1 was previously mapped from the cultivar ‘Dowling’ to a 12 centiMorgan (cM) marker interval on soybean chromosome 7 [formerly linkage group (LG)...

  5. Soybean germplasm accession seedling reactions to soybean rust isolates from Georgia

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean rust (SBR), caused by Phakopsora pachyrhizi, is a threat to soybean [Glycine max (L.) Merr.] production in regions of the world where winters are not cold enough to completely eliminate the many hosts of the fungus, so resistant soybean cultivars would be useful in managing this disease. Res...

  6. Distribution of Soybean Cyst Nematode in Nebraska

    PubMed Central

    Powers, T. O.; Sandall, L. J.; Wysong, D. S.

    1989-01-01

    A survey of 552 soybean fields in 20 counties in Nebraska in 1986-88 revealed 35 fields infested with the soybean cyst nematode (SCN), Heterodera glycines. Identification was confirmed with a greenhouse bioassay, using 'Lee 74' soybean, and by the application of a DNA hybridization probe derived from SCN mitochondrial DNA. Most of the SCN-infested fields were located on the Missouri River floodplain and in the southeastern corner of the state. PMID:19287657

  7. Acrylic Resin Cytotoxicity for Denture Base--Literature Review.

    PubMed

    Goiato, Marcelo C; Freitas, Emily; dos Santos, Daniela; de Medeiros, Rodrigo; Sonego, Mariana

    2015-01-01

    Acrylic resin is a widely used material in clinical practice, and a satisfactory biocompatibility is essential. When the resin polymerization reaction is incomplete, residual monomers are released into the oral cavity. The aim of this study was to evaluate, through a literature review, the cytotoxicity caused by the denture base acrylic resin used, and its components. The selection of published studies was performed on the Pubmed database from January 2008 to July 2013. The keywords used were: "cytotoxicity and acrylic resins", "cytotoxicity and denture base resins" and "cytotoxicity and oral prosthesis". Inclusion criteria were: in vitro studies and literature reviews published in English that evaluated the acrylic resin cytotoxicity for denture base and its components. Studies with no reference to the search strategy were excluded. A total of 182 articles were found. Among these, only 13 were included for writing this review. The MTT test is the most common test used to evaluate acrylic resin cytotoxicity. Auto-polymerized resin is more cytotoxic than heat-polymerized resin because of its higher quantity of residual monomers which cause cell and tissue changes in the oral mucosa. However, more studies are necessary for the development of biocompatible materials.

  8. Impact Delamination and Fracture in Aluminum/Acrylic Sandwich Plates

    NASA Technical Reports Server (NTRS)

    Liaw, Benjamin; Zeichner, Glenn; Liu, Yanxiong; Bowles, Kenneth J. (Technical Monitor)

    2000-01-01

    Impact-induced delamination and fracture in 6061-T6 aluminum/cast acrylic sandwich plates adhered by epoxy were generated in an instrumented drop-weight impact machine. Although only a small dent was produced on the aluminum side when a hemispherical penetrator tup was dropped onto it from a couple of inches, a large ring of delamination at the interface was observed. The delamination damage was often accompanied by severe shattering in the acrylic substratum. Damage patterns in the acrylic layer include radial and ring cracks and, together with delamination at the interface, may cause peeling-off of acrylic material from the sandwich plate. Theory of stress-wave propagation can be used to explain these damage patterns. The impact tests were conducted at various temperatures. The results also show clearly that temperature effect is very important in impact damage. For pure cast acrylic nil-ductile transition (NDT) occurs between 185-195 F. Excessive impact energy was dissipated into fracture energy when tested at temperature below this range or through plastic deformation when tested at temperature above the NDT temperature. Results from this study will be used as baseline data for studying fiber-metal laminates, such as GLARE and ARALL for advanced aeronautical and astronautical applications.

  9. Sultones and Sultines via a Julia-Kocienski Reaction of Epoxides.

    PubMed

    Smith, Geoffrey M T; Burton, Paul M; Bray, Christopher D

    2015-12-01

    The development of the homologous Julia-Kocienski reaction has led to the discovery of two new reaction modes of epoxides with sulfones. These pathways allow rapid and direct access to a range of γ-sultones and γ-sultines.

  10. EXPRESSION AND CHARACTERIZATION OF THE RECOMBINANT JUVENILE HORMONE EPOXIDE HYDROLASE (JHEH) FROM MANDUCA SEXTA. (R825433)

    EPA Science Inventory

    The cDNA of the microsomal Juvenile Hormone Epoxide Hydrolase (JHEH) from Manduca sexta was expressed in vitro in the baculovirus system. In insect cell culture, the recombinant enzyme (Ms-JHEH) was produced at a high level (100 fold over background EH catalytic activit...

  11. Synthesis of an Epoxide Carbonylation Catalyst: Exploration of Contemporary Chemistry for Advanced Undergraduates

    ERIC Educational Resources Information Center

    Getzler, Yutan D. Y. L.; Schmidt, Joseph A. R.; Coates, Geoffrey W.

    2005-01-01

    A class of highly active, well-defined compounds for the catalytic carbonylation of epoxides and aziridines to beta-lactones and beta-lactams are introduced. The synthesis of one of the catalysts involves a simple imine condensation to form the ligand followed by air-sensitive metalation and salt metathesis steps.

  12. INTERACTION OF BENZO(A)PYRENE DIOL EPOXIDE WITH SVAO MINICHROMOSOMES

    SciTech Connect

    Gamper, Howard B.; Yokota, Hisao A.; Bartholomew, James C.

    1980-03-01

    SV40 minichromosomes were reacted with (+)7{beta},8{alpha}-dihydroxy-9{alpha},10{alpha}-epoxy- 7,8,9,10-tetrahydrobenzo[a]pyrene (BaP diol epoxide). Low levels of modification (< 5 DNA adducts/minichromosome) did not detectably alter the structure of the minichromosomes but high levels (> 200 DNA adducts/minichromosome) led to extensive fragmentation. Relative to naked SV40 DNA BaP diol epoxide induced alkylation and strand scission of minichromosomal DNA was reduced or enhanced by factors of 1.5 and 2.0, respectively. The reduction in covalent binding was attributed to the presence of histones, which competed with DNA for the hydrocarbon and reduced the probability of BaP diol epoxide intercalation by tightening the helix. The enhancement of strand scission was probably due to the catalytic effect of histones on the rate of S-elimination at apurinic sites, although an altered adduct profile or the presence of a repair endonuclease were not excluded. Staphylococcal nuclease digestion indicated that BaP dial epoxide randomly alkylated the minichromosomal DNA. This is in contrast to studies with cellular chromatin where internucleosomal DNA was preferentially modified. Differences in the minichromosomal protein complement were responsible for this altered susceptibility.

  13. Catalytic epoxidation by perrhenate through the formation of organic-phase supramolecular ion pairs.

    PubMed

    Cokoja, Mirza; Markovits, Iulius I E; Anthofer, Michael H; Poplata, Saner; Pöthig, Alexander; Morris, Danny S; Tasker, Peter A; Herrmann, Wolfgang A; Kühn, Fritz E; Love, Jason B

    2015-02-25

    Organic-phase supramolecular ion pair (SIP) host-guest assemblies of perrhenate anions (ReO4(-)) with ammonium amide receptor cations are reported. These compounds act as catalysts for the epoxidation of alkenes by aqueous hydrogen peroxide under biphasic conditions and can be recycled several times with no loss in activity.

  14. Signature motifs identify an Acinetobacter Cif virulence factor with epoxide hydrolase activity.

    PubMed

    Bahl, Christopher D; Hvorecny, Kelli L; Bridges, Andrew A; Ballok, Alicia E; Bomberger, Jennifer M; Cady, Kyle C; O'Toole, George A; Madden, Dean R

    2014-03-14

    Endocytic recycling of the cystic fibrosis transmembrane conductance regulator (CFTR) is blocked by the CFTR inhibitory factor (Cif). Originally discovered in Pseudomonas aeruginosa, Cif is a secreted epoxide hydrolase that is transcriptionally regulated by CifR, an epoxide-sensitive repressor. In this report, we investigate a homologous protein found in strains of the emerging nosocomial pathogens Acinetobacter nosocomialis and Acinetobacter baumannii ("aCif"). Like Cif, aCif is an epoxide hydrolase that carries an N-terminal secretion signal and can be purified from culture supernatants. When applied directly to polarized airway epithelial cells, mature aCif triggers a reduction in CFTR abundance at the apical membrane. Biochemical and crystallographic studies reveal a dimeric assembly with a stereochemically conserved active site, confirming our motif-based identification of candidate Cif-like pathogenic EH sequences. Furthermore, cif expression is transcriptionally repressed by a CifR homolog ("aCifR") and is induced in the presence of epoxides. Overall, this Acinetobacter protein recapitulates the essential attributes of the Pseudomonas Cif system and thus may facilitate airway colonization in nosocomial lung infections. PMID:24474692

  15. Formation of furan fatty alkyl esters from their bis-epoxide fatty esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Reactions of epoxidized alkyl soyate with four different alcohols: ethanol, isopropyl alcohol, 2-ethylhexanol, benzyl alcohol, in the presence of Bronsted acid catalyst, were investigated. Products that were not reported in prior studies of similar reactions were found. These were furan fatty acid a...

  16. (Salen)Mn(III) Catalyzed Asymmetric Epoxidation Reactions by Hydrogen Peroxide in Water: A Green Protocol

    PubMed Central

    Ballistreri, Francesco Paolo; Gangemi, Chiara M. A.; Pappalardo, Andrea; Tomaselli, Gaetano A.; Toscano, Rosa Maria; Trusso Sfrazzetto, Giuseppe

    2016-01-01

    Enantioselective epoxidation reactions of some chosen reactive alkenes by a chiral Mn(III) salen catalyst were performed in H2O employing H2O2 as oxidant and diethyltetradecylamine N-oxide (AOE-14) as surfactant. This procedure represents an environmentally benign protocol which leads to e.e. values ranging from good to excellent (up to 95%). PMID:27420047

  17. Formation of furan fatty alkyl esters from their bis-epoxide fatty esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Reactions of epoxidized alkyl soyate with four different alcohols: ethanol, isopropyl alcohol, 2-ethylhexanol, and benzyl alcohol were investigated in the presence of Bronsted acid catalyst. Products not reported in prior studies of similar reactions were found. These were furan fatty acid alkyl est...

  18. Differences in Catalytic Sites for CO Oxidation and Propylene Epoxidation on Au Nanoparticles

    SciTech Connect

    Lee, W.S.; Stach, E.; Zhang, R.; Akatay, M.C.; Baertsch, C.D.; Ribeiro, F.H.; Delgass, W.N.

    2011-08-29

    Sintering and increased Au loading of Au/TS-1 causes the rate of CO oxidation per mole of Au to increase, whereas that for epoxidation of propylene in O{sub 2} and H{sub 2} decreases. This opposite trend in rate behavior shows that the catalytic sites for the two reactions must be different.

  19. EPOXIDATION OF SMALL ORGANIC MOLECULES USING A SPINNING TUBE-IN-TUBE REACTOR

    EPA Science Inventory

    The commodity-scale epoxidation of several organic molecules has been carried out using a Spinning Tube-in-Tube (STTr) reactor (manufactured by Kreido Laboratories). This reactor, which embodies and facilitates the use of Green Chemistry principles and Process Intensification, a...

  20. Highly selective oxidative cleavage of beta-cyclodextrin-epoxide/aziridine complexes with IBX in water.

    PubMed

    Surendra, K; Krishnaveni, N Srilakshmi; Reddy, M Arjun; Nageswar, Y V D; Rao, K Rama

    2003-11-14

    Water, an environmentally friendly reaction medium, has been utilized for the reaction of IBX with various epoxides 1 and aziridines 2 as their beta-cyclodextrin complexes to afford for the first time alpha-hydroxyketones 3 and alpha-aminoketones 4, respectively.

  1. Synthesis of epoxidized cardanol and its antioxidative properties for vegetable oils and biodiesel

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A novel antioxidant epoxidized cardanol (ECD), derived from cardanol, was synthesized and characterized by FT-IR, 1H-NMR and 13C-NMR. Oxidative stability of ECD used in vegetable oils and biodiesel was evaluated by pressurized differential scanning calorimetry (PDSC) and the Rancimat method, respect...

  2. Diastereoselective synthesis of CF3-substituted, epoxide-fused heterocycles with β-(trifluoromethyl)vinylsulfonium salts.

    PubMed

    Fritz, Sven P; West, Thomas H; McGarrigle, Eoghan M; Aggarwal, Varinder K

    2012-12-21

    CF(3)-substituted vinyl diphenylsulfonium triflate is an effective annulation reagent for the formation of α-CF(3) substituted, epoxide-fused heterocycles (pyrrolidines, piperidines, and tetrahydrofurans). This simple method affords a variety of valuable heterocyclic building blocks in a highly diastereoselective manner (dr >20:1). PMID:23231752

  3. Deep eutectic solvents (DESs) are viable cosolvents for enzyme-catalyzed epoxide hydrolysis.

    PubMed

    Lindberg, Diana; de la Fuente Revenga, Mario; Widersten, Mikael

    2010-06-01

    A special group of ionic liquids, deep eutectic solvents (DESs) have been tested as cosolvents in enzyme-catalyzed hydrolysis of a chiral (1,2)-trans-2-methylstyrene oxide. The choline chloride:ethane diol (ET), choline chloride:glycerol (GLY) and choline:chloride:urea (REL) DESs were included in the reaction mixtures with epoxide and the potato epoxide hydrolase StEH1. The effect of the DESs on enzyme function was primarily elevations of K(M) (up to 20-fold) and with lesser effects on turnover numbers (twofold variation). The regioselectivity in hydrolysis of the (1R,2R)-2-trans-methylstyrene oxide was altered in the presence of GLY or ET to favor epoxide ring opening at the benzylic carbon (R=2.33), enhancing the regioselectivity observed in buffer-only systems (R=1.35). The DES solutions dissolved 1.5-fold higher epoxide concentrations as compared to phosphate buffer. The total conversion of high concentration (40 g/l) of (1S,2S)-MeSO was not negatively affected by addition of 40% GLY. PMID:20438773

  4. Metabolism of methaqualone by the epoxide-diol pathway in man and the rat.

    PubMed

    Stillwell, W G; Gregory, P A; Horning, M G

    1975-01-01

    The metabolism of methaqualone (2-methyl-3-o-tolyl-4(3H)-quinazolinone) has been studied in man and the rat using gas phase analytical methods. Seven new metabolites formed by the epoxide-diol pathway were detected in human urine after methaqualone administration. Five of these compounds were characterized as dihydrodiols and two as hydroxydihydrodiols. The seven dihydrodiol metabolites were present in the nonhydrolyzed fraction isolated from urine. After intraperitoneal administration of methaqualone to the rat (40 mg/kg) the major monohydroxyl metabolites of the drug in hydrolyzed urine were identified as 2-methyl-3-(2'-hydroxymethylphenyl)-4(3H)-quinazolinone (I) and 2-hydroxymethyl-3-o-tolyl-4(3H)-quinazolinone (II). Two dihydroxyl metabolites were also present, but only trace amounts of a dihydrodiol were detected. The major monohydroxyl metabolites of methaqualone detected in human urine after enzymic hydrolysis were I, II, 2-methyl-3-(3'-hydroxy-2'-methylphenyl)-4(3H)-quinazolinone (III), and 2-methyl-3-(4'-hydroxy-2'-methylphenyl)-4(3H)-quinazolinone (IV). Hydroxylation of the tolyl moiety of methaqualone probably occurs by way of an epoxide intermediate. The phenols, III and IV, may be formed from an epoxide or from the dihydrodiol(s) by enzymic or nonenzymic reactions. The results obtained suggest that epoxidation of methaqualone represents a major pathway of metabolism in the human.

  5. Genes encoding vitamin-K epoxide reductase are present in Drosophila and trypanosomatid protists.

    PubMed

    Robertson, Hugh M

    2004-10-01

    Vitamin-K epoxide reductase is encoded by the VKORC1 gene in mammals and other vertebrates, which also have a paralog, VKORC1L1. Single homologs are present in basal deuterostome and insect genomes, including Drosophila, and three trypanosomatid protists. VKOR is therefore an ancient gene/protein that can be studied in the Drosophila model system.

  6. Engineering of an epoxide hydrolase for efficient bioresolution of bulky pharmaco substrates

    PubMed Central

    Kong, Xu-Dong; Yuan, Shuguang; Li, Lin; Chen, She; Xu, Jian-He; Zhou, Jiahai

    2014-01-01

    Optically pure epoxides are essential chiral precursors for the production of (S)-propranolol, (S)-alprenolol, and other β-adrenergic receptor blocking drugs. Although the enzymatic production of these bulky epoxides has proven difficult, here we report a method to effectively improve the activity of BmEH, an epoxide hydrolase from Bacillus megaterium ECU1001 toward α-naphthyl glycidyl ether, the precursor of (S)-propranolol, by eliminating the steric hindrance near the potential product-release site. Using X-ray crystallography, mass spectrum, and molecular dynamics calculations, we have identified an active tunnel for substrate access and product release of this enzyme. The crystal structures revealed that there is an independent product-release site in BmEH that was not included in other reported epoxide hydrolase structures. By alanine scanning, two mutants, F128A and M145A, targeted to expand the potential product-release site displayed 42 and 25 times higher activities toward α-naphthyl glycidyl ether than the wild-type enzyme, respectively. These results show great promise for structure-based rational design in improving the catalytic efficiency of industrial enzymes for bulky substrates. PMID:25331869

  7. Discovery and characterization of thermophilic limonene-1,2-epoxide hydrolases from hot spring metagenomic libraries.

    PubMed

    Ferrandi, Erica Elisa; Sayer, Christopher; Isupov, Michail N; Annovazzi, Celeste; Marchesi, Carlotta; Iacobone, Gianluca; Peng, Xu; Bonch-Osmolovskaya, Elizaveta; Wohlgemuth, Roland; Littlechild, Jennifer A; Monti, Daniela

    2015-08-01

    The epoxide hydrolases (EHs) represent an attractive option for the synthesis of chiral epoxides and 1,2-diols which are valuable building blocks for the synthesis of several pharmaceutical compounds. A metagenomic approach has been used to identify two new members of the atypical EH limonene-1,2-epoxide hydrolase (LEH) family of enzymes. These two LEHs (Tomsk-LEH and CH55-LEH) show EH activities towards different epoxide substrates, differing in most cases from those previously identified for Rhodococcus erythropolis (Re-LEH) in terms of stereoselectivity. Tomsk-LEH and CH55-LEH, both from thermophilic sources, have higher optimal temperatures and apparent melting temperatures than Re-LEH. The new LEH enzymes have been crystallized and their structures solved to high resolution in the native form and in complex with the inhibitor valpromide for Tomsk-LEH and poly(ethylene glycol) for CH55-LEH. The structural analysis has provided insights into the LEH mechanism, substrate specificity and stereoselectivity of these new LEH enzymes, which has been supported by mutagenesis studies.

  8. Thermal behavior of epoxidized cardanol diethyl phosphate as novel renewable plasticizer for poly(vinyl chloride)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A novel plasticizer, epoxidized cardanol diethyl phosphate (ECEP), based on cardanol was synthesized. Chemical structure of ECEP was characterized by fourier transform infrared (FTIR), 1H-nuclear magnetic resonance(1H NMR) and 13C-nuclear magnetic resonance(13C NMR) spectroscopy. Effects of ECEP sub...

  9. Oxodiperoxo molybdenum modified mesoporous MCM-41 materials for the catalytic epoxidation of cyclooctene.

    PubMed

    Jia, Mingjun; Thiel, Werner R

    2002-10-21

    A hybrid heterogeneous catalyst system, which has been synthesized by covalently anchoring oxodiperoxo molybdenum chelate complexes onto the surface of mesoporous MCM-41, is highly active and truly heterogeneous for the liquid-phase epoxidation of cyclooctene with tBuOOH as the oxygen source.

  10. Surface Tension Studies of Alkyl Esters and Epoxidized Alkyl Esters Relevant to Oleochemically Based Fuel Additives

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We report the surface tension of several epoxidized oleochemicals and their comparable fatty esters at temperatures between 25 and 60 deg C. Surface tensions of the olefins measured at 40 deg C range from 25.9 mN m-1, for isobutyl oleate, to 28.4 mN m-1 for methyl linoleate. The epoxy versions of ...

  11. Graphene oxide as an acid catalyst for the room temperature ring opening of epoxides.

    PubMed

    Dhakshinamoorthy, Amarajothi; Alvaro, Mercedes; Concepción, Patricia; Fornés, Vicente; Garcia, Hermenegildo

    2012-06-01

    The minute amount of hydrogen sulfate groups introduced into the graphene oxide (GO) obtained by Hummers oxidation of graphite renders this material as a highly efficient, recyclable acid catalyst for the ring opening of epoxides with methanol and other primary alcohols as nucleophile and solvent. PMID:22534622

  12. 40 CFR 63.1431 - Process vent annual epoxides emission factor plan requirements.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... factor plan requirements. 63.1431 Section 63.1431 Protection of Environment ENVIRONMENTAL PROTECTION... Polyether Polyols Production § 63.1431 Process vent annual epoxides emission factor plan requirements. (a) Applicability of emission factor plan requirements. An owner or operator electing to comply with an...

  13. Preferential Glutathione Conjugation of a Reverse Diol Epoxide Compared to a Bay Region Diol Epoxide of Phenanthrene in Human Hepatocytes: Relevance to Molecular Epidemiology Studies of Glutathione-S-Transferase Polymorphisms and Cancer

    PubMed Central

    Hecht, Stephen S.; Berg, Jeannette Zinggeler; Hochalter, J. Bradley

    2009-01-01

    Bay region diol epoxides are recognized ultimate carcinogens of polycyclic aromatic hydrocarbons (PAH), and in vitro studies have demonstrated that they can be detoxified by conjugation with glutathione, leading to the widely investigated hypothesis that individuals with low activity forms of glutathione-S-transferases are at higher risk of PAH induced cancer, a hypothesis that has found at most weak support in molecular epidemiology studies. A weakness in this hypothesis was that the mercapturic acids resulting from conjugation of PAH bay region diol epoxides had never been identified in human urine. We recently analyzed smokers’ urine for mercapturic acids derived from phenanthrene, the simplest PAH with a bay region. The only phenanthrene diol epoxide-derived mercapturic acid in smokers’ urine was produced from the reverse diol epoxide, anti-phenanthrene-3,4-diol-1,2-epoxide (11), not the bay region diol epoxide, anti-phenanthrene-1,2-diol-3,4-epoxide (10), which does not support the hypothesis noted above. In this study, we extended these results by examining the conjugation of phenanthrene metabolites with glutathione in human hepatocytes. We identified the mercapturic acid N-acetyl-S-(r-4,t-2,3-trihydroxy-1,2,3,4-tetrahydro-c-1-phenanthryl)-L-cysteine (14a), (0.33–35.9 pmol/mL at 10 µM 8, 24h incubation, N = 10) in all incubations with phenanthrene-3,4-diol (8) and the corresponding diol epoxide 11, but no mercapturic acids were detected in incubations with phenanthrene-1,2-diol (7) and only trace amounts were observed in incubations with the corresponding bay region diol epoxide 10. Taken together with our previous results, these studies clearly demonstrate that glutathione conjugation of a reverse diol epoxide of phenanthrene is favored over conjugation of a bay region diol epoxide. Since reverse diol epoxides of PAH are generally weakly or non-mutagenic/carcinogenic, these results, if generalizable to other PAH, do not support the widely held

  14. Occurrance in Korea of three major soybean viruses, Soybean mosaic virus (SMV), Soybean yellow mottle mosaic virus (SYCMV), and Soybean yellow common mosaic virus (SYCMV) revealed by a nationwide survey of soybean fields

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean yellow mottle mosaic virus (SYMMV) and soybean yellow common mosaic virus (SYCMV) were recently isolated in Korea, and it hasn’t been reported how these two viruses were dispersed in Korea. In 2012, we performed a nationwide survey of subsistence soybean farms in Korea. Leaves that appeared ...

  15. Mononuclear Nonheme High-Spin Iron(III)-Acylperoxo Complexes in Olefin Epoxidation and Alkane Hydroxylation Reactions.

    PubMed

    Wang, Bin; Lee, Yong-Min; Clémancey, Martin; Seo, Mi Sook; Sarangi, Ritimukta; Latour, Jean-Marc; Nam, Wonwoo

    2016-02-24

    Mononuclear nonheme high-spin iron(III)-acylperoxo complexes bearing an N-methylated cyclam ligand were synthesized, spectroscopically characterized, and investigated in olefin epoxidation and alkane hydroxylation reactions. In the epoxidation of olefins, epoxides were yielded as the major products with high stereo-, chemo-, and enantioselectivities; cis- and trans-stilbenes were oxidized to cis- and trans-stilbene oxides, respectively. In the epoxidation of cyclohexene, cyclohexene oxide was formed as the major product with a kinetic isotope effect (KIE) value of 1.0, indicating that nonheme iron(III)-acylperoxo complexes prefer C═C epoxidation to allylic C-H bond activation. Olefin epoxidation by chiral iron(III)-acylperoxo complexes afforded epoxides with high enantioselectivity, suggesting that iron(III)-acylperoxo species, not high-valent iron-oxo species, are the epoxidizing agent. In alkane hydroxylation reactions, iron(III)-acylperoxo complexes hydroxylated C-H bonds as strong as those in cyclohexane at -40 °C, wherein (a) alcohols were yielded as the major products with high regio- and stereoselectivities, (b) activation of C-H bonds by the iron(III)-acylperoxo species was the rate-determining step with a large KIE value and good correlation between reaction rates and bond dissociation energies of alkanes, and (c) the oxygen atom in the alcohol product was from the iron(III)-acylperoxo species, not from molecular oxygen. In isotopically labeled water (H2(18)O) experiments, incorporation of (18)O from H2(18)O into oxygenated products was not observed in the epoxidation and hydroxylation reactions. On the basis of mechanistic studies, we conclude that mononuclear nonheme high-spin iron(III)-acylperoxo complexes are strong oxidants capable of oxygenating hydrocarbons prior to their conversion into iron-oxo species via O-O bond cleavage.

  16. Pilot scale production, characterization, and optimization of epoxidized vegetable oil-based resins

    NASA Astrophysics Data System (ADS)

    Monono, Ewumbua Menyoli

    Novel epoxidized sucrose soyate (ESS) resins perform much better than other vegetable oil-based resins; thus, they are of current interest for commercial scale production and for a wide range of applications in coatings and polymeric materials. However, no work has been published that successfully scaled-up the reaction above a 1 kg batch size. To achieve this goal, canola oil was first epoxidized at a 300 g scale to study the epoxidation rate and thermal profile at different hydrogen peroxide (H2O2) addition rates, bath temperatures, and reaction times. At least 83% conversion of double bonds to oxirane was achieved by 2.5 h, and the reaction temperature was 8-15 °C higher than the water bath temperature within the first 30-40 min of epoxidation. A 38 L stainless steel kettle was modified as a reactor to produce 10 kg of ESS. Twenty 7-10 kg batches of ESS were produced with an overall 87.5% resin yield and > 98% conversion after batch three. The conversion and resin quality were consistent across the batches due to the modifications on the reaction that improved mixing and reaction temperature control within 55-65 oC. The total production time was reduced from 8 to 4 days due to the fabrication of a 40 L separatory funnel for both washing and filtration. A math model was developed to optimize the epoxidation process. This was done by using the Box-Behnken design to model the conversion at various acetic acid, H2O2, and Amberlite ratios and at various reaction temperatures and times. The model had an adjusted R2 of 97.6% and predicted R2 of 96.8%. The model showed that reagent amounts and time can be reduced by 18% without compromising the desired conversion value and quality.

  17. Discovery of a Novel Microsomal Epoxide Hydrolase-Catalyzed Hydration of a Spiro Oxetane.

    PubMed

    Li, Xue-Qing; Hayes, Martin A; Grönberg, Gunnar; Berggren, Kristina; Castagnoli, Neal; Weidolf, Lars

    2016-08-01

    Oxetane moieties are increasingly being used by the pharmaceutical industry as building blocks in drug candidates because of their pronounced ability to improve physicochemical parameters and metabolic stability of drug candidates. The enzymes that catalyze the biotransformation of the oxetane moiety are, however, not well studied. The in vitro metabolism of a spiro oxetane-containing compound AZD1979 [(3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone] was studied and one of its metabolites, M1, attracted our interest because its formation was NAD(P)H independent. The focus of this work was to elucidate the structure of M1 and to understand the mechanism(s) of its formation. We established that M1 was formed via hydration and ring opening of the oxetanyl moiety of AZD1979. Incubations of AZD1979 using various human liver subcellular fractions revealed that the hydration reaction leading to M1 occurred mainly in the microsomal fraction. The underlying mechanism as a hydration, rather than an oxidation reaction, was supported by the incorporation of (18)O from H2 (18)O into M1. Enzyme kinetics were performed probing the formation of M1 in human liver microsomes. The formation of M1 was substantially inhibited by progabide, a microsomal epoxide hydrolase inhibitor, but not by trans-4-[4-(1-adamantylcarbamoylamino)cyclohexyloxy]benzoic acid, a soluble epoxide hydrolase inhibitor. On the basis of these results, we propose that microsomal epoxide hydrolase catalyzes the formation of M1. The substrate specificity of microsomal epoxide hydrolase should therefore be expanded to include not only epoxides but also the oxetanyl ring system present in AZD1979. PMID:27256986

  18. Titania-silica mixed oxides. II. Catalytic behaviour in olefin epoxidation

    SciTech Connect

    Hutter, R.; Mallat, T.; Baiker, A.

    1995-04-15

    Various titania-silica aerogels prepared by an alkoxide-sol-gel route have been tested in the epoxidation of bulky olefins using cumene hydroperoxide as oxidant. The drying method, the titanium content between 2 and 20 wt%, and the calcination temperature between 473 and 1073 K were the most important preparation parameters, influencing the catalytic behaviour of the aerogels. The aerogels dried by semicontinuous extraction with supercritical CO{sub 2} at low temperature (LT aerogel) were found to be much more efficient epoxidation catalysts than aerogels prepared by high-temperature supercritical drying and conventionally dried xerogels. The reaction rate of cyclohexene epoxidation over LT aerogels increased monotonically with increasing Ti content. In the range of 333-363 K the catalysts containing 20 wt% TiO{sub 2} (20LT) showed high activity and selectivity (79-93% to peroxide and 87-100% to epoxide) in the oxidation of various cyclic olefins, including cyclododecene, norbornene, cyclohexene, and limonene. Catalytic experiments, FTIR, and UV-vis spectroscopy indicated that the LT aerogels consist of two different types of active species: titanium well-dispersed in the silica matrix and titania nanodomains. The key factors determining the activity and selectivity of sol-gel titania-silica catalysts are the morphology (surface area and pore size) and the relative proportions of Ti-O-Si and Ti-O-Ti structural parts. A comparative study of the epoxidation of cyclohexene, cyclododecene, and norbornene over structurally different titania-silica catalysts, indicates that 20LT shows better catalytic behaviour in these reactions than Ti zeolites and silica-supported titania. 46 refs., 12 figs., 3 tabs.

  19. Reusable manganese compounds containing pyrazole-based ligands for olefin epoxidation reactions.

    PubMed

    Manrique, Ester; Poater, Albert; Fontrodona, Xavier; Solà, Miquel; Rodríguez, Montserrat; Romero, Isabel

    2015-10-28

    We describe the synthesis of new manganese(ii) and manganese(iii) complexes containing the bidentate ligands 2-(3-pyrazolyl)pyridine, pypz-H, and 3(5)-(2-hydroxyphenyl)pyrazole, HOphpz-H, with formula [MnX2(pypz-H)2] (X = Cl(-), 1, CF3SO3(-), 2, OAc(-), 3 or NO3(-) (4)), [MnCl2(pypz-H)(H2O)2], 5, or [MnCl(Ophpz-H)2], 6. All the complexes have been characterized through analytical, spectroscopic and electrochemical techniques. Single X-ray structure analysis revealed a six-coordinated Mn(ii) ion in complexes 1-5, and a five-coordinated Mn(iii) ion in complex 6. Compound 5 is the first co-crystal of Mn(ii) containing Cl and H2O ligands together with bidentate nitrogen ligands. The catalytic activity of complexes 1-6 has been tested with regard to the epoxidation of styrene and, in the case of 1, 5 and 6, other alkenes have been epoxidized using peracetic acid as oxidant in different media, among which glycerol, a green solvent never used in epoxidation reactions using peracetic acid as oxidant. The catalysts show moderate to high conversions and selectivities towards the corresponding epoxides. For complexes 1, 5 and 6, a certain degree of cis→trans isomerization is observed in the case of cis-β-methylstyrene. These observations have been explained through computational calculations. The reutilization of catalysts 1 and 6 for the epoxidation of alkenes has been evaluated in [bmim] : acetonitrile mixture (bmim = 1-butyl-3-methylimidazolium), allowing the effective recyclability of the catalytic system and keeping high conversion and selectivity values up to 12 successive runs, in all cases.

  20. Reusable manganese compounds containing pyrazole-based ligands for olefin epoxidation reactions.

    PubMed

    Manrique, Ester; Poater, Albert; Fontrodona, Xavier; Solà, Miquel; Rodríguez, Montserrat; Romero, Isabel

    2015-10-28

    We describe the synthesis of new manganese(ii) and manganese(iii) complexes containing the bidentate ligands 2-(3-pyrazolyl)pyridine, pypz-H, and 3(5)-(2-hydroxyphenyl)pyrazole, HOphpz-H, with formula [MnX2(pypz-H)2] (X = Cl(-), 1, CF3SO3(-), 2, OAc(-), 3 or NO3(-) (4)), [MnCl2(pypz-H)(H2O)2], 5, or [MnCl(Ophpz-H)2], 6. All the complexes have been characterized through analytical, spectroscopic and electrochemical techniques. Single X-ray structure analysis revealed a six-coordinated Mn(ii) ion in complexes 1-5, and a five-coordinated Mn(iii) ion in complex 6. Compound 5 is the first co-crystal of Mn(ii) containing Cl and H2O ligands together with bidentate nitrogen ligands. The catalytic activity of complexes 1-6 has been tested with regard to the epoxidation of styrene and, in the case of 1, 5 and 6, other alkenes have been epoxidized using peracetic acid as oxidant in different media, among which glycerol, a green solvent never used in epoxidation reactions using peracetic acid as oxidant. The catalysts show moderate to high conversions and selectivities towards the corresponding epoxides. For complexes 1, 5 and 6, a certain degree of cis→trans isomerization is observed in the case of cis-β-methylstyrene. These observations have been explained through computational calculations. The reutilization of catalysts 1 and 6 for the epoxidation of alkenes has been evaluated in [bmim] : acetonitrile mixture (bmim = 1-butyl-3-methylimidazolium), allowing the effective recyclability of the catalytic system and keeping high conversion and selectivity values up to 12 successive runs, in all cases. PMID:26389716

  1. Capsanthone 3,6-epoxide, a new carotenoid from the fruits of the red paprika Capsicum annuum L.

    PubMed

    Maoka, T; Fujiwara, Y; Hashimoto, K; Akimoto, N

    2001-08-01

    The structure of a new carotenoid, isolated from the fruits of the red tomato-shaped paprika Capsicum annuum L., was elucidated to be (3S,5R,6S,5'R)-3,6-epoxy-5,6-dihydro-5-hydroxy-beta,kappa-carotene-3',6'-dione by spectroscopic analyses, including fast atom bombardment collision-induced dissociation-mass spectrometry/mass spectrometry (FAB CID-MS/MS) and was designated capsanthone 3,6-epoxide. Capsanthone 3,6-epoxide is assumed to be an oxidative metabolite of capsanthin 3,6-epoxide in paprika.

  2. Biosynthetic pathway for acrylic acid from glycerol in recombinant Escherichia coli.

    PubMed

    Tong, Wenhua; Xu, Ying; Xian, Mo; Niu, Wei; Guo, Jiantao; Liu, Huizhou; Zhao, Guang

    2016-06-01

    Acrylic acid is an important industrial feedstock. In this study, a de novo acrylate biosynthetic pathway from inexpensive carbon source glycerol was constructed in Escherichia coli. The acrylic acid was produced from glycerol via 3-hydroxypropionaldehyde, 3-hydroxypropionyl-CoA, and acrylyl-CoA. The acrylate production was improved by screening and site-directed mutagenesis of key enzyme enoyl-CoA hydratase and chromosomal integration of some exogenous genes. Finally, our recombinant strain produced 37.7 mg/L acrylic acid under shaking flask conditions. Although the acrylate production is low, our study shows feasibility of engineering an acrylate biosynthetic pathway from inexpensive carbon source. Furthermore, the reasons for limited acrylate production and further strain optimization that should be performed in the future were also discussed. PMID:26782744

  3. Nucleophilic addition of reactive dyes on amidoximated acrylic fabrics.

    PubMed

    El-Shishtawy, Reda M; El-Zawahry, Manal M; Abdelghaffar, Fatma; Ahmed, Nahed S E

    2014-01-01

    Seven reactive dyes judiciously selected based on chemical structures and fixation mechanisms were applied at 2% of of shade on amidoximated acrylic fabrics. Amidoximated acrylic fabric has been obtained by a viable amidoximation process. The dyeability of these fabrics was evaluated with respect to the dye exhaustion, fixation, and colour strength under different conditions of temperature and dyeing time. Nucleophilic addition type reactive dyes show higher colour data compared to nucleophilic substitution ones. FTIR studies further implicate the binding of reactive dyes on these fabrics. A tentative mechanism is proposed to rationalize the high fixation yield obtained using nucleophilic addition type reactive dyes. Also, the levelling and fastness properties were evaluated for all dyes used. Excellent to good fastness and levelling properties were obtained for all samples irrespective of the dye used. The result of investigation offers a new method for a viable reactive dyeing of amidoximated acrylic fabrics.

  4. Properties of the modified cellulosic fabrics using polyurethane acrylate copolymers.

    PubMed

    Tabasum, Shazia; Zuber, Mohammad; Jabbar, Abdul; Zia, Khalid Mahmood

    2013-05-15

    Polyurethane acrylate copolymers (PAC) were synthesized via emulsion polymerization following three step synthesis process using toluene-2,4-diisocyanate, hydroxy terminated poly(caprolactone) diol, 2-hydroxyethylacrylate (HEA) and butyl acrylate (BuA). Structural characteristics of the synthesized polyurethane acrylate copolymer (PAC) were studied using Fourier Transform Infrared (FT-IR) spectrophotometer and are with accordance with the proposed PAC structure. The physicochemical properties such as solid contents (%), tackiness, film appearance and emulsion stability were studied, discussed and co-related with other findings. The plain weave poly-cotton printed fabrics after application of PAC was evaluated applying colorfastness standard test method. The results revealed that emulsion stability is the main controlling factor of the synthesized material in order to get better applications and properties. The emulsion stability of the synthesized material increased with increase in molecular weight of the polycaprolactone diol. PMID:23544644

  5. Properties of the modified cellulosic fabrics using polyurethane acrylate copolymers.

    PubMed

    Tabasum, Shazia; Zuber, Mohammad; Jabbar, Abdul; Zia, Khalid Mahmood

    2013-05-15

    Polyurethane acrylate copolymers (PAC) were synthesized via emulsion polymerization following three step synthesis process using toluene-2,4-diisocyanate, hydroxy terminated poly(caprolactone) diol, 2-hydroxyethylacrylate (HEA) and butyl acrylate (BuA). Structural characteristics of the synthesized polyurethane acrylate copolymer (PAC) were studied using Fourier Transform Infrared (FT-IR) spectrophotometer and are with accordance with the proposed PAC structure. The physicochemical properties such as solid contents (%), tackiness, film appearance and emulsion stability were studied, discussed and co-related with other findings. The plain weave poly-cotton printed fabrics after application of PAC was evaluated applying colorfastness standard test method. The results revealed that emulsion stability is the main controlling factor of the synthesized material in order to get better applications and properties. The emulsion stability of the synthesized material increased with increase in molecular weight of the polycaprolactone diol.

  6. Biocatalytic functionalization of hydroxyalkyl acrylates and phenoxyethanol via phosphorylation.

    PubMed

    Tasnádi, Gábor; Hall, Mélanie; Baldenius, Kai; Ditrich, Klaus; Faber, Kurt

    2016-09-10

    The enzymatic phosphorylation of phenoxyethanol, 2-hydroxyethyl acrylate and 4-hydroxybutyl acrylate catalyzed by acid phosphatases PhoN-Sf and PiACP at the expense of inorganic di-, tri-, hexameta- or polyphosphate was applied to the preparative-scale synthesis of phosphorylated compounds. The reaction conditions were optimized with respect to enzyme immobilization, substrate concentration, pH and type of phosphate donor. The mild reaction conditions prevented undesired polymerization and hydrolysis of the acrylate ester moiety. Application of a continuous flow system allowed facile scale-up and mono-phosphates were obtained in up to 26% isolated yield with space-time yields of 0.89kgL(-1)h(-1). PMID:27422352

  7. Biocatalytic functionalization of hydroxyalkyl acrylates and phenoxyethanol via phosphorylation.

    PubMed

    Tasnádi, Gábor; Hall, Mélanie; Baldenius, Kai; Ditrich, Klaus; Faber, Kurt

    2016-09-10

    The enzymatic phosphorylation of phenoxyethanol, 2-hydroxyethyl acrylate and 4-hydroxybutyl acrylate catalyzed by acid phosphatases PhoN-Sf and PiACP at the expense of inorganic di-, tri-, hexameta- or polyphosphate was applied to the preparative-scale synthesis of phosphorylated compounds. The reaction conditions were optimized with respect to enzyme immobilization, substrate concentration, pH and type of phosphate donor. The mild reaction conditions prevented undesired polymerization and hydrolysis of the acrylate ester moiety. Application of a continuous flow system allowed facile scale-up and mono-phosphates were obtained in up to 26% isolated yield with space-time yields of 0.89kgL(-1)h(-1).

  8. Colour Stability of Heat and Cold Cure Acrylic Resins

    PubMed Central

    Ganesh, P R; Reddy, Madan Mohan; Ebenezar, A.V. Rajesh; Sivakumar, G

    2015-01-01

    Introduction: To evaluate the colour stability of heat and cold cure acrylic resins under simulated oral conditions with different colorants. Materials and Methods: Three different brands of heat cure acrylic resin and two rapid cure auto polymerizing acrylic resin of commercial products such as Trevelon Heat Cure (THC), DPI Heat cure (DHC), Pyrax Heat Cure (PHC), DPI Cold cure (DCC) and Acralyn-R-Cold cure (ACC) have been evaluated for discoloration and colour variation on subjecting it to three different, commonly employed food colorants such as Erythrosine, Tartarizine and Sunset yellow. In order to simulate the oral condition the food colorants were diluted with artificial saliva to the samples taken up for the study. These were further kept in an incubator at 37°C ± 1°C. The UV-visible spectrophotometer has been utilized to evaluate the study on the basis of CIE L* a* b* system. The prepared samples for standard evaluation have been grouped as control group, which has been tested with a white as standard, which is applicable for testing the colour variants. Results: The least colour changes was found to be with Sunset Yellow showing AE* value of 3.55 with heat cure acrylic resin branded as PHC material and the highest colour absorption with Tartarizine showing AE* value of 12.43 in rapid cure autopolymerzing acrylic resin material branded as ACC material. Conclusion: ACC which is a self cure acrylic resin shows a higher colour variation to the tartarizine food coloration. There were not much of discoloration values shown on the denture base resins as the food colorants are of organic azodyes. PMID:25738078

  9. Technology and the use of acrylics for provisional dentine protection.

    PubMed

    Kapusevska, Biljana; Dereban, Nikola; Popovska, Mirjana; Nikolovska, Julijana; Radojkova Nikolovska, Vеrа; Zabokova Bilbilova, Efka; Mijoska, Aneta

    2013-01-01

    Acrylics are compounds polymerized from monomers of acrylic, metacrylic acid or acrylonitrates. The purpose of this paper is to present the technology and use of acrylics for provisional dentine protection in the practice of dental prosthodontics. For this reason, we followed 120 clinical cases from the everyday clinical practice, divided into 4 groups of 30 patients who needed prosthetic reconstruction. The first group included cases in which we applied celluloid crowns for dentine protection, for the second group we used acrylic teeth from a set of teeth for complete dentures; in the third and fourth groups the fabrication was done with the system of an impression matrix and the acrylic resin block technique respectively. In all the examined patients, the gingival index by Silness and Loe and the vitality of the dental pulp were verified clinically, after preparation and 8 days from the placement of the provisional crown. The value for dental sensitivity measured after preparation was 2.59, and 8 days after the placement of the provisional crown it bwas 3.1. From these results we can conclude that after the 8th day from the placement of the provisional crown, there was an adaptation period, characterized by a decrease in the painful sensations. The value of the Silness and Loe gingival index measured after the preparation was 1.34, and 8 days from the placement of the provisional crown was 0.94. The results inclined us to the fact that the provisional acrylic crowns facilitated the reparation of the periodontal tissue. PMID:24566021

  10. The creep behavior of acrylic denture base resins.

    PubMed

    Sadiku, E R; Biotidara, F O

    1996-01-01

    The creep behavior of acrylic dental base resins, at room temperature and at different loading conditions, has been examined. The behaviors of these resins are similar to that of "commercial perspex" at room temperature over a period of 1000 seconds. The pseudo-elastic moduli of the blends of PMMA VC show a significant increase compared with PMMA alone. The addition of the PVC powder to the heat-cured acrylic resin increased the time-dependent elastic modulus. This increase in elastic modulus is advantageous in the production of denture based resins of improv mechanical properties.

  11. Kinetic relationships governing addition of methanol to methyl acrylate

    SciTech Connect

    Chubarov, G.A.; Danov, S.M.; Kutnyaya, M.Yu.

    1988-11-10

    The kinetic relationships governing the addition of methanol to methyl acrylate and the reverse reaction, i.e., the elimination of methanol from methyl /beta/-methoxypropionate catalyzed by sulfuric and p-toluenesulfonic acids, were investigated. The rate of the forward reaction depends on the concentrations of methyl acrylate, methanol, and the catalyst, and the rate of the reverse reaction depends on the concentration of methyl /beta/-methoxypropionate and of the catalyst. A kinetic expression which describes the process well was obtained.

  12. Corrosion resistant properties of polyaniline acrylic coating on magnesium alloy

    NASA Astrophysics Data System (ADS)

    Sathiyanarayanan, S.; Azim, S. Syed; Venkatachari, G.

    2006-12-01

    The performance of the paint coating based on acrylic-polyaniline on magnesium alloy ZM 21 has been studied by electrochemical impedance spectroscopy in 0.5% NaCl solution. The polyaniline was prepared by chemical oxidative method of aniline with ammonium persulphate in phosphoric acid medium. The phosphate-doped polyaniline was characterized by FTIR and XRD methods. Acrylic paint containing the phosphate-doped polyaniline was prepared and coated on magnesium ZM 21 alloy. The coating was able to protect the magnesium alloy and no base metal dissolution was noted even after 75 days exposure to sodium chloride solution.

  13. Cardiovascular effects of acrylic bone cement in rabbits and cats.

    PubMed

    Pelling, D; Butterworth, K R

    1973-06-16

    The cardiovascular responses to forcing acrylic bone cement, Plasticine, or soft paraffin wax into the medullary cavity of the femur have been studied in rabbits and cats. An acute fall in blood pressure, occurring within a few seconds of insertion, was demonstrated with each substance. In a few of the animals the blood pressure response had a second more protracted component and it is suggested that more than one mechanism is involved. The cardiovascular effects that have been observed in man when acrylic cement is used in prosthetic hip surgery also may be due to more than one mechanism. PMID:4714847

  14. Lipase-catalyzed aza-Michael reaction on acrylate derivatives.

    PubMed

    Steunenberg, Peter; Sijm, Maarten; Zuilhof, Han; Sanders, Johan P M; Scott, Elinor L; Franssen, Maurice C R

    2013-04-19

    A methodology has been developed for an efficient and selective lipase-catalyzed aza-Michael reaction of various amines (primary and secondary) with a series of acrylates and alkylacrylates. Reaction parameters were tuned, and under the optimal conditions it was found that Pseudomonas stutzeri lipase and Chromobacterium viscosum lipase showed the highest selectivity for the aza-Michael addition to substituted alkyl acrylates. For the first time also, some CLEAs were examined that showed a comparable or higher selectivity and yield than the free enzymes and other formulations.

  15. SOYBEAN.DEFOLIATION.1.SD.2011

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Various chewing insects feed upon soybean plants, and their infestations may be economically significant in some years in the north-central United States. Soybean lines that are resistant to defoliation may be useful for management of chewing insect pests. Levels of defoliation from chewing insec...

  16. SOYBEAN.DEFOLIATION.2.SD.2011

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Several types of chewing insects feed upon soybean plants, and their infestations may be economically significant in some years in the north-central United States. Soybean lines that are resistant to defoliation may be useful in the management of chewing insect pests. Levels of defoliation from c...

  17. Analysis of soybean flowering-time genes

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Control of soybean flowering time is important for geographic adaptation, and maximizing yield. RT-PCR analysis was performed using primers synthesized for a number of putative flowering-time genes based on homology of soybean EST and genomic sequences to Arabidopsis genes. RNA for cDNA synthesis ...

  18. 40 CFR 721.6560 - Acrylic acid, polymer with substituted ethene.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.6560 Acrylic acid, polymer with substituted ethene. (a) Chemical... as acrylic acid, polymer with substituted ethene (PMN P-91-521) is subject to reporting under...

  19. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  20. 40 CFR 721.10223 - Styrenyl surface treated manganese ferrite with acrylic ester polymer (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... ferrite with acrylic ester polymer (generic). 721.10223 Section 721.10223 Protection of Environment... manganese ferrite with acrylic ester polymer (generic). (a) Chemical substance and significant new uses... manganese ferrite with acrylic ester polymer (PMN P-09-582) is subject to reporting under this section...

  1. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  2. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  3. 40 CFR 721.463 - Acrylate of polymer based on isophorone diisocyanate (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acrylate of polymer based on... New Uses for Specific Chemical Substances § 721.463 Acrylate of polymer based on isophorone... substance identified generically as acrylate of polymer based on isophorone diisocyanate (PMN P-00-0626)...

  4. 40 CFR 721.10032 - Acrylic acid, polymer with substituted acrylamides (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.10032 Acrylic acid, polymer with substituted acrylamides (generic). (a... generically as acrylic acid, polymer with substituted acrylamides (PMN P-02-269) is subject to reporting...

  5. 40 CFR 721.6560 - Acrylic acid, polymer with substituted ethene.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.6560 Acrylic acid, polymer with substituted ethene. (a) Chemical... as acrylic acid, polymer with substituted ethene (PMN P-91-521) is subject to reporting under...

  6. 40 CFR 721.463 - Acrylate of polymer based on isophorone diisocyanate (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acrylate of polymer based on... New Uses for Specific Chemical Substances § 721.463 Acrylate of polymer based on isophorone... substance identified generically as acrylate of polymer based on isophorone diisocyanate (PMN P-00-0626)...

  7. 40 CFR 721.10032 - Acrylic acid, polymer with substituted acrylamides (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.10032 Acrylic acid, polymer with substituted acrylamides (generic). (a... generically as acrylic acid, polymer with substituted acrylamides (PMN P-02-269) is subject to reporting...

  8. 40 CFR 721.463 - Acrylate of polymer based on isophorone diisocyanate (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Acrylate of polymer based on... New Uses for Specific Chemical Substances § 721.463 Acrylate of polymer based on isophorone... substance identified generically as acrylate of polymer based on isophorone diisocyanate (PMN P-00-0626)...

  9. 40 CFR 721.6560 - Acrylic acid, polymer with substituted ethene.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.6560 Acrylic acid, polymer with substituted ethene. (a) Chemical... as acrylic acid, polymer with substituted ethene (PMN P-91-521) is subject to reporting under...

  10. 40 CFR 721.10032 - Acrylic acid, polymer with substituted acrylamides (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.10032 Acrylic acid, polymer with substituted acrylamides (generic). (a... generically as acrylic acid, polymer with substituted acrylamides (PMN P-02-269) is subject to reporting...

  11. 40 CFR 721.10223 - Styrenyl surface treated manganese ferrite with acrylic ester polymer (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... ferrite with acrylic ester polymer (generic). 721.10223 Section 721.10223 Protection of Environment... manganese ferrite with acrylic ester polymer (generic). (a) Chemical substance and significant new uses... manganese ferrite with acrylic ester polymer (PMN P-09-582) is subject to reporting under this section...

  12. 40 CFR 721.10223 - Styrenyl surface treated manganese ferrite with acrylic ester polymer (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... ferrite with acrylic ester polymer (generic). 721.10223 Section 721.10223 Protection of Environment... manganese ferrite with acrylic ester polymer (generic). (a) Chemical substance and significant new uses... manganese ferrite with acrylic ester polymer (PMN P-09-582) is subject to reporting under this section...

  13. 40 CFR 721.10101 - Copolymer of alkyl acrylate and ethyleneglycol dimethacrylate (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Copolymer of alkyl acrylate and... Significant New Uses for Specific Chemical Substances § 721.10101 Copolymer of alkyl acrylate and...) The chemical substance identified generically as copolymer of alkyl acrylate and...

  14. 40 CFR 721.10101 - Copolymer of alkyl acrylate and ethyleneglycol dimethacrylate (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Copolymer of alkyl acrylate and... Significant New Uses for Specific Chemical Substances § 721.10101 Copolymer of alkyl acrylate and...) The chemical substance identified generically as copolymer of alkyl acrylate and...

  15. 40 CFR 721.10101 - Copolymer of alkyl acrylate and ethyleneglycol dimethacrylate (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Copolymer of alkyl acrylate and... Significant New Uses for Specific Chemical Substances § 721.10101 Copolymer of alkyl acrylate and...) The chemical substance identified generically as copolymer of alkyl acrylate and...

  16. 40 CFR 721.10101 - Copolymer of alkyl acrylate and ethyleneglycol dimethacrylate (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Copolymer of alkyl acrylate and... Significant New Uses for Specific Chemical Substances § 721.10101 Copolymer of alkyl acrylate and...) The chemical substance identified generically as copolymer of alkyl acrylate and...

  17. 21 CFR 177.1340 - Ethylene-methyl acrylate copolymer resins.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Ethylene-methyl acrylate copolymer resins. 177.1340... copolymer resins. Ethylene-methyl acrylate copolymer resins may be safely used as articles or components of...) For the purpose of this section, the ethylene-methyl acrylate copolymer resins consist of...

  18. 40 CFR 721.10192 - Amides, coco, N-[3-(dibutylamino)propyl], acrylates.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Amides, coco, N- , acrylates. 721... Substances § 721.10192 Amides, coco, N- , acrylates. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as amides, coco, N- , acrylates (PMN...

  19. 40 CFR 721.10192 - Amides, coco, N-[3-(dibutylamino)propyl], acrylates.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Amides, coco, N- , acrylates. 721... Substances § 721.10192 Amides, coco, N- , acrylates. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as amides, coco, N- , acrylates (PMN...

  20. 21 CFR 177.1340 - Ethylene-methyl acrylate copolymer resins.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Ethylene-methyl acrylate copolymer resins. 177... for Use as Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1340 Ethylene-methyl acrylate copolymer resins. Ethylene-methyl acrylate copolymer resins may be safely used...

  1. 21 CFR 177.1340 - Ethylene-methyl acrylate copolymer resins.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Ethylene-methyl acrylate copolymer resins. 177... for Use as Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1340 Ethylene-methyl acrylate copolymer resins. Ethylene-methyl acrylate copolymer resins may be safely used...

  2. 21 CFR 177.1340 - Ethylene-methyl acrylate copolymer resins.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Ethylene-methyl acrylate copolymer resins. 177... Repeated Use Food Contact Surfaces § 177.1340 Ethylene-methyl acrylate copolymer resins. Ethylene-methyl... section, the ethylene-methyl acrylate copolymer resins consist of basic copolymers produced by...

  3. 40 CFR 721.463 - Acrylate of polymer based on isophorone diisocyanate (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Acrylate of polymer based on... New Uses for Specific Chemical Substances § 721.463 Acrylate of polymer based on isophorone... substance identified generically as acrylate of polymer based on isophorone diisocyanate (PMN P-00-0626)...

  4. 40 CFR 721.463 - Acrylate of polymer based on isophorone diisocyanate (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acrylate of polymer based on... New Uses for Specific Chemical Substances § 721.463 Acrylate of polymer based on isophorone... substance identified generically as acrylate of polymer based on isophorone diisocyanate (PMN P-00-0626)...

  5. 40 CFR 721.10032 - Acrylic acid, polymer with substituted acrylamides (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.10032 Acrylic acid, polymer with substituted acrylamides (generic). (a... generically as acrylic acid, polymer with substituted acrylamides (PMN P-02-269) is subject to reporting...

  6. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  7. 40 CFR 721.10223 - Styrenyl surface treated manganese ferrite with acrylic ester polymer (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... ferrite with acrylic ester polymer (generic). 721.10223 Section 721.10223 Protection of Environment... manganese ferrite with acrylic ester polymer (generic). (a) Chemical substance and significant new uses... manganese ferrite with acrylic ester polymer (PMN P-09-582) is subject to reporting under this section...

  8. 40 CFR 721.6560 - Acrylic acid, polymer with substituted ethene.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.6560 Acrylic acid, polymer with substituted ethene. (a) Chemical... as acrylic acid, polymer with substituted ethene (PMN P-91-521) is subject to reporting under...

  9. 40 CFR 721.10032 - Acrylic acid, polymer with substituted acrylamides (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.10032 Acrylic acid, polymer with substituted acrylamides (generic). (a... generically as acrylic acid, polymer with substituted acrylamides (PMN P-02-269) is subject to reporting...

  10. 40 CFR 721.6560 - Acrylic acid, polymer with substituted ethene.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Acrylic acid, polymer with substituted... Specific Chemical Substances § 721.6560 Acrylic acid, polymer with substituted ethene. (a) Chemical... as acrylic acid, polymer with substituted ethene (PMN P-91-521) is subject to reporting under...

  11. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  12. 40 CFR 721.9640 - Salt of an acrylic acid - acrylamide terpolymer (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Salt of an acrylic acid - acrylamide... Specific Chemical Substances § 721.9640 Salt of an acrylic acid - acrylamide terpolymer (generic). (a... generically as salt of an acrylic acid - acrylamide terpolymer (PMN P-99-817) is subject to reporting...

  13. 40 CFR 721.321 - Substituted acrylamides and acrylic acid copolymer (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted acrylamides and acrylic... New Uses for Specific Chemical Substances § 721.321 Substituted acrylamides and acrylic acid copolymer... identified generically as substituted acrylamides and acrylic acid copolymer (PMN P-00-0490) is subject...

  14. 40 CFR 721.321 - Substituted acrylamides and acrylic acid copolymer (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Substituted acrylamides and acrylic... New Uses for Specific Chemical Substances § 721.321 Substituted acrylamides and acrylic acid copolymer... identified generically as substituted acrylamides and acrylic acid copolymer (PMN P-00-0490) is subject...

  15. 40 CFR 721.321 - Substituted acrylamides and acrylic acid copolymer (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted acrylamides and acrylic... New Uses for Specific Chemical Substances § 721.321 Substituted acrylamides and acrylic acid copolymer... identified generically as substituted acrylamides and acrylic acid copolymer (PMN P-00-0490) is subject...

  16. 40 CFR 721.9640 - Salt of an acrylic acid - acrylamide terpolymer (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Salt of an acrylic acid - acrylamide... Specific Chemical Substances § 721.9640 Salt of an acrylic acid - acrylamide terpolymer (generic). (a... generically as salt of an acrylic acid - acrylamide terpolymer (PMN P-99-817) is subject to reporting...

  17. 40 CFR 721.9640 - Salt of an acrylic acid - acrylamide terpolymer (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Salt of an acrylic acid - acrylamide... Specific Chemical Substances § 721.9640 Salt of an acrylic acid - acrylamide terpolymer (generic). (a... generically as salt of an acrylic acid - acrylamide terpolymer (PMN P-99-817) is subject to reporting...

  18. 40 CFR 721.338 - Salt of an acrylate copolymer (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Salt of an acrylate copolymer (generic... Substances § 721.338 Salt of an acrylate copolymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as salt of an acrylate...

  19. 40 CFR 721.338 - Salt of an acrylate copolymer (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Salt of an acrylate copolymer (generic... Substances § 721.338 Salt of an acrylate copolymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as salt of an acrylate...

  20. 40 CFR 721.338 - Salt of an acrylate copolymer (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Salt of an acrylate copolymer (generic... Substances § 721.338 Salt of an acrylate copolymer (generic). Link to an amendment published at 79 FR 34636... substances identified generically as salt of an acrylate copolymer (PMNs P-00-0333 and P-00-0334) are...

  1. 40 CFR 721.338 - Salt of an acrylate copolymer (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Salt of an acrylate copolymer (generic... Substances § 721.338 Salt of an acrylate copolymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as salt of an acrylate...

  2. 40 CFR 721.338 - Salt of an acrylate copolymer (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Salt of an acrylate copolymer (generic... Substances § 721.338 Salt of an acrylate copolymer (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substances identified generically as salt of an acrylate...

  3. 40 CFR 721.321 - Substituted acrylamides and acrylic acid copolymer (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted acrylamides and acrylic... New Uses for Specific Chemical Substances § 721.321 Substituted acrylamides and acrylic acid copolymer... identified generically as substituted acrylamides and acrylic acid copolymer (PMN P-00-0490) is subject...

  4. 40 CFR 721.321 - Substituted acrylamides and acrylic acid copolymer (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Substituted acrylamides and acrylic... New Uses for Specific Chemical Substances § 721.321 Substituted acrylamides and acrylic acid copolymer... identified generically as substituted acrylamides and acrylic acid copolymer (PMN P-00-0490) is subject...

  5. 40 CFR 721.9640 - Salt of an acrylic acid - acrylamide terpolymer (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Salt of an acrylic acid - acrylamide... Specific Chemical Substances § 721.9640 Salt of an acrylic acid - acrylamide terpolymer (generic). (a... generically as salt of an acrylic acid - acrylamide terpolymer (PMN P-99-817) is subject to reporting...

  6. 40 CFR 721.9640 - Salt of an acrylic acid - acrylamide terpolymer (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Salt of an acrylic acid - acrylamide... Specific Chemical Substances § 721.9640 Salt of an acrylic acid - acrylamide terpolymer (generic). (a... generically as salt of an acrylic acid - acrylamide terpolymer (PMN P-99-817) is subject to reporting...

  7. Tensile bond strength between auto-polymerized acrylic resin and acrylic denture teeth treated with MF-MA solution

    PubMed Central

    2016-01-01

    PURPOSE This study evaluated the effect of chemical surface treatment using methyl formate-methyl acetate (MF-MA) solution on the tensile bond strength between acrylic denture teeth and auto-polymerized acrylic resin. MATERIALS AND METHODS Seventy maxillary central incisor acrylic denture teeth for each of three different brands (Yamahachi New Ace; Major Dent; Cosmo HXL) were embedded with incisal edge downwards in auto-polymerized resin in polyethylene pipes and ground with silicone carbide paper on their ridge lap surfaces. The teeth of each brand were divided into seven groups (n=10): no surface treatment (control group), MF-MA solution at a ratio of 25:75 (v/v) for 15 seconds, 30 seconds, 60 seconds, 120 seconds, 180 seconds, and MMA for 180 seconds. Auto-polymerized acrylic resin (Unifast Trad) was applied to the ground surface and polymerized in a pressure cooker. A tensile strength test was performed with a universal testing machine. Statistical analysis of the results was performed using two-way analysis of variance (ANOVA) and post-hoc Dunnett T3 test (α=.05). RESULTS The surface treatment groups had significantly higher mean tensile bond strengths compared with the control group (P<.05) when compared within the same brand. Among the surface treatment groups of each brand, there were no significantly different tensile bond strengths between the MF-MA groups and the MMA 180 second group (P>.05), except for the Yamahachi New Ace MF-MA 180-second group (P<.05). CONCLUSION 15-second MF-MA solution can be an alternative chemical surface treatment for repairing a denture base and rebonding acrylic denture teeth with auto-polymerized acrylic resin, for both conventional and cross-linked teeth. PMID:27555897

  8. Stereoselective formations of K-region and non-K-region epoxides in the metabolism of chrysene by rat liver microsomal cytochrome P-450 isozymes.

    PubMed

    Yang, S K; Bao, Z P

    1987-07-01

    The K-region 5,6-epoxide and non-K-region 1,2- and 3,4-epoxides of chrysene were isolated by normal phase high performance liquid chromatography (HPLC) from a mixture of products formed in the metabolism of chrysene by liver microsomes from untreated (control), phenobarbital-treated, or 3-methylcholanthrene-treated rats in the presence of an epoxide hydrolase inhibitor, 3,3,3-trichloropropylene 1,2-oxide. Epoxides were characterized by ultraviolet, mass, and circular dichroism spectral and chiral stationary phase HPLC analyses. Each of the metabolically formed epoxides was hydrated by rat liver microsomal epoxide hydrolase to a trans-dihydrodiol. The metabolically formed chrysene 5,6-epoxides were determined by chiral stationary phase HPLC and were found to contain (5S,6R):(5R,6S) enantiomer ratios of 68:32 (control), 71:29 (phenobarbital), and 5:95 (3-methylcholanthrene), respectively. The enantiomers of chrysene 1,2-epoxide and 3,4-epoxide were also resolved by chiral stationary phase HPLC. However, the enantiomeric compositions of the metabolically formed chrysene 1,2- and 3,4-epoxides, which racemized rapidly at room temperature, could not be directly determined. By using molecular oxygen-18 in the in vitro incubation of chrysene and by mass spectral analyses of the resulting oxygen-18-containing dihydrodiol metabolites and their acid-catalyzed dehydration (phenolic) products, both 1,2-epoxide and 3,4-epoxide were found to be converted by microsomal epoxide hydrolase-catalyzed water attack at predominantly (greater than or equal to 97%) the allylic carbons.

  9. Trends in predicted chemoselectivity of cytochrome P450 oxidation: B3LYP barrier heights for epoxidation and hydroxylation reactions.

    PubMed

    Rydberg, Patrik; Lonsdale, Richard; Harvey, Jeremy N; Mulholland, Adrian J; Olsen, Lars

    2014-07-01

    Prediction of epoxide formation in drug metabolism is a difficult but important task, as epoxide formation is linked to drug toxicity. A comparison of the energy barriers for cytochrome P450 mediated epoxidation of alkenes to the barriers for the hydroxylation of an aliphatic carbon atom next to a double bond has been performed using B3LYP and B3LYP-D3. Relevant experimental data on oxidation selectivity has also been assessed. The results show that density functional theory, when using B3LYP-D3, does well in reproducing the experimental trends. Considering that the comparison involves chemical steps with quite different features this is remarkable. We also find that B3LYP consistently underestimates the hydrogen abstraction barriers relative to the epoxidation barriers, and that including a dispersion correction reduces this problem.

  10. Isolation of β-Cryptoxanthin-epoxides, Precursors of Cryptocapsin and 3'-Deoxycapsanthin, from Red Mamey (Pouteria sapota).

    PubMed

    Turcsi, Erika; Murillo, Enrique; Kurtán, Tibor; Szappanos, Ádám; Illyés, Tünde-Zita; Gulyás-Fekete, Gergely; Agócs, Attila; Avar, Péter; Deli, József

    2015-07-01

    From an extract of red mamey (Pouteria sapota) β-cryptoxanthin-5,6-epoxide, β-cryptoxanthin-5',6'-epoxide, 3'-deoxycapsanthin, and cryptocapsin were isolated and characterized by UV-vis spectroscopy, electronic circular dichroism (ECD), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). Epoxidation of β-cryptoxanthin delivered the β-(5'R,6'S)- and (5'S,6'R)-cryptoxanthin-5',6'-epoxides, which were identified by HPLC-ECD analysis. These carotenoids among others are quite common in the fruits of Central America, and as they are natural provitamins A, they should play an important role in the diet of the mostly vitamin A deficient population of this region. PMID:26057604

  11. Isolation of β-Cryptoxanthin-epoxides, Precursors of Cryptocapsin and 3'-Deoxycapsanthin, from Red Mamey (Pouteria sapota).

    PubMed

    Turcsi, Erika; Murillo, Enrique; Kurtán, Tibor; Szappanos, Ádám; Illyés, Tünde-Zita; Gulyás-Fekete, Gergely; Agócs, Attila; Avar, Péter; Deli, József

    2015-07-01

    From an extract of red mamey (Pouteria sapota) β-cryptoxanthin-5,6-epoxide, β-cryptoxanthin-5',6'-epoxide, 3'-deoxycapsanthin, and cryptocapsin were isolated and characterized by UV-vis spectroscopy, electronic circular dichroism (ECD), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). Epoxidation of β-cryptoxanthin delivered the β-(5'R,6'S)- and (5'S,6'R)-cryptoxanthin-5',6'-epoxides, which were identified by HPLC-ECD analysis. These carotenoids among others are quite common in the fruits of Central America, and as they are natural provitamins A, they should play an important role in the diet of the mostly vitamin A deficient population of this region.

  12. Epoxide pathways improve model predictions of isoprene markers and reveal key role of acidity in aerosol formation

    EPA Science Inventory

    Isoprene significantly contributes to organic aerosol in the southeastern United States where biogenic hydrocarbons mix with anthropogenic emissions. In this work, the Community Multiscale Air Quality model is updated to predict isoprene aerosol from epoxides produced under both ...

  13. Genome-wide association mapping of soybean aphid resistance traits

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean aphid is the most damaging insect pest of soybean in the Upper Midwest and is primarily controlled by insecticides. Soybean aphid resistance (i.e., Rag genes) has been documented in some soybean lines at chromosomes 6, 7, 13, and 16, but more sources of resistance are needed. Genome-wide ass...

  14. Translating Soybean Genomics to Opportunities for Improved Human Health

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Soybean is a major crop for food and fuel. While the vast majority of soybean meal is incorporated into the diet of livestock such as poultry and swine, the soybean oil is extremely valuable as a component of the human diet. Many soybean breeding efforts are targeted to improve agronomic traits suc...

  15. 7 CFR 1220.313 - Qualified State Soybean Boards.

    Code of Federal Regulations, 2010 CFR

    2010-01-01

    ... 7 Agriculture 10 2010-01-01 2010-01-01 false Qualified State Soybean Boards. 1220.313 Section 1220... SERVICE (MARKETING AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN... Soybean Boards. The following State soybean promotion organizations shall be Qualified State...

  16. 7 CFR 1220.313 - Qualified State Soybean Boards.

    Code of Federal Regulations, 2014 CFR

    2014-01-01

    ... 7 Agriculture 10 2014-01-01 2014-01-01 false Qualified State Soybean Boards. 1220.313 Section 1220... SERVICE (MARKETING AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN... Soybean Boards. The following State soybean promotion organizations shall be Qualified State...

  17. 7 CFR 1220.313 - Qualified State Soybean Boards.

    Code of Federal Regulations, 2011 CFR

    2011-01-01

    ... 7 Agriculture 10 2011-01-01 2011-01-01 false Qualified State Soybean Boards. 1220.313 Section 1220... SERVICE (MARKETING AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN... Soybean Boards. The following State soybean promotion organizations shall be Qualified State...

  18. 7 CFR 1220.313 - Qualified State Soybean Boards.

    Code of Federal Regulations, 2012 CFR

    2012-01-01

    ... 7 Agriculture 10 2012-01-01 2012-01-01 false Qualified State Soybean Boards. 1220.313 Section 1220... SERVICE (MARKETING AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN... Soybean Boards. The following State soybean promotion organizations shall be Qualified State...

  19. 7 CFR 1220.313 - Qualified State Soybean Boards.

    Code of Federal Regulations, 2013 CFR

    2013-01-01

    ... 7 Agriculture 10 2013-01-01 2013-01-01 false Qualified State Soybean Boards. 1220.313 Section 1220... SERVICE (MARKETING AGREEMENTS AND ORDERS; MISCELLANEOUS COMMODITIES), DEPARTMENT OF AGRICULTURE SOYBEAN... Soybean Boards. The following State soybean promotion organizations shall be Qualified State...

  20. Soybean aphid intrabiotype variability based on colonization of specific soybean genotypes.

    PubMed

    Pawlowski, Michelle; Hill, Curtis B; Voegtlin, David J; Hartman, Glen L

    2015-12-01

    The soybean aphid, Aphis glycines Matsumura (Hemiptera: Aphididae), is one of the most destructive insect pests on soybeans in the United States. One method for managing this pest is through host plant resistance. Since its arrival in 2000, 4 aphid biotypes have been identified that are able to overcome soybean aphid resistance (Rag) genes. A soybean aphid isolate collected from Moline, Illinois readily colonized soybean plants with the soybean aphid resistance gene Rag2, unlike biotypes 1 and 2, but similar to soybean aphid biotype 3. Two no-choice experiments compared the virulence of the Moline isolate with biotype 3. In both experiments, differences in aphid population counts were not significant (P > 0.05) on soybean genotypes LD08-12957a (Rag2) and LD11-5413a (Rag2), but the aphid counts for the Moline isolate were significantly (P < 0.05) lower than the aphid counts for the biotype 3 isolate on the soybean genotypes Dowling (Rag1), LD05-16611 (Rag1), LD11-4576a (Rag1), and PI 567598B (rag1b and rag3). The Moline isolate was a variant of aphid biotype 3, which is the first report showing that soybean aphid isolates classified as the same biotype, based on virulence against specific Rag genes, can differ in aggressiveness or ability to colonize specific host genotypes.