- Biocatalyzed esterification of oleic acid using cell suspension and dried biomass of Aspergillus sp. RBD01
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Esterification is an industrially important reaction in the field of food and fuel industries. In biofuel and allied industries, long-chain alkyl esters are generally produced from different fat rich feedstocks including non-edible oils, acid oils, and tallow, using a variety of catalysts. Amongst these, whole cell systems have prominently been explored in recent past. The present study focused on the use of Aspergillus sp. RBD01 as a whole cell catalyst, in dry and whole cell suspension, to esterify oleic acid with different alcohols as acyl acceptors. Esterification with dried biomass resulted in better conversion of oleic acid to its respective ester as compared to cell suspension. Further, increase in chain length of alcohol resulted in decrease in the yield from ethyl oleate (98% EO) to decyl oleate (77% DO) with alcohols having an even number of carbon atoms giving better yield of esters over alcohols with odd numbers.
- Aulakh, Satnam Singh,Sharma, Anirudh,Tejo Prakash,Prakash, Ranjana
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- Biodiesel production using a carbon solid acid catalyst derived from β-cyclodextrin
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A novel carbon solid acid catalyst was prepared by incomplete hydrothermal carbonization of β-cyclodextrin into small polycyclic aromatic carbon sheets, followed by the introduction of -SO3H groups via sulfonation with sulfuric acid. The physical and chemical properties of the catalyst were characterized in detail. The catalyst simultaneously catalyzed esterification and transesterification reactions to produce biodiesel from high free fatty acid (FFA) containing oils (55.2%). For the as-prepared catalyst, 90.82% of the oleic acid was esterified after 8 h, while the total transesterification yield of high FFA containing oils reached 79.98% after 12 h. By contrast, the obtained catalyst showed comparable activity to biomass (such as sugar, starch, etc.)-based carbon solid acid catalyst while Amberlyst-15 resulted in significantly lower levels of conversion, demonstrating its relatively high catalytic activity for simultaneous esterification and transesterification. Moreover, as the catalyst can be regenerated, it has the potential for use in biodiesel production from oils with a high FFA content.
- Fu, Xiao-Bo,Chen, Jie,Song, Xue-Li,Zhang, Yuan-Ming,Zhu, Yi,Yang, Jun,Zhang, Cheng-Wu
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- Transesterification of glycerol trioleate catalyzed by basic ionic liquids immobilized on magnetic nanoparticles: Influence of pore diffusion effect
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Supported ionic liquids have become a hotspot in heterogeneous catalysis. 1-Allyl-dodecylimidazolium hydroxide ([ADIm][OH]) basic ionic liquids immobilized on magnetic mesoporous SiO2/CoFe2O4 nanoparticles (SCF) and magnetic CoFe2O4 nanoparticles (CF) were prepared and characterized via FTIR, XRD, TEM, TG-DTA, VSM, elemental analysis and N2 adsorption-desorption measurements. Catalytic performance of both supported ionic liquids catalysts (SILCs) was evaluated through transesterification of glycerol trioleate. The SCF carrier consisted of mesoporous silica matrix and uniformly dispersed CoFe2O4 nanoparticles, while CF carriers were nanosized CoFe2O4 particles with an average size of 15 nm. All of the carriers and the supported catalysts showed excellent paramagnetism. The two SILCs showed excellent catalytic activities higher than NaOH. Furthermore, the structure of the carriers had important influence on the catalytic performance of SILCs. Compared with the two SILCs, [ADIm][OH]/SCF presented a lower catalytic activity at the beginning of the reaction but higher catalytic activity when reaction time was long enough than [ADIm][OH]/CF due to the pore diffusion effect.
- Zhang, Yaping,Jiao, Qingze,Zhen, Bin,Wu, Qin,Li, Hansheng
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- Thermal degradation and isomerisation kinetics of triolein studied by infrared spectrometry and GC-MS combined with chemometrics
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Triolein, a triglyceride containing oleic acid as the only acid moiety in the glyceride molecules has been isothermally treated at 280, 300, and 325 °C in glass vials under nitrogen atmosphere. The products formed during the thermal treatment at each temperature have been analysed both by infrared spectrometry and GC-MS. The GC-MS analysis was performed after derivatisation of the fatty acids into their methyl esters (FAMEs). Chemometric tools were used in determining the concentrations of the main products namely triolein and trieaidin in the thermally treated mixtures. The concentration profiles of the trielaidin formed during thermal treatment at the above three temperatures were used in determining activation energy for the cis-trans isomerisation of triolein. The combined analysis reveals that the thermal treatment induces not only cis-trans isomerisation but also fission and fusion in the molecules. Furthermore, migration of the double bond in oleic and elaidic acids forming cis and trans isomers of the 18:1 acid was also observed. The heat-induced isomerisation in triolein follows a zeroth order reaction with an activation energy 41 ± 5 kcal/mol.
- Christy, Alfred A.,Xu, Zhanfeng,Harrington, Peter de B.
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- Immobilization of Thermomyces lanuginosus lipase on ZnO nanoparticles: Mimicking the interfacial environment
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Thermomyces lanuginosus lipase (TL lipase) was immobilized covalently on ZnO nanoparticles (NPs) functionalized with small amino acid molecules, like glycine. Glutaraldehyde was used as a spacer between the ZnO/glycine Nps and the enzyme. This study is based on the observation that the favorable conformation of an enzyme (in which the catalytic lid is exposed to reactant molecules) can be obtained at the lipid/water interface and such an interfacial environment can be mimicked by properly designing the carrier used as the support for its immobilization. Glycine functionalized ZnO NPs were covalently bonded with glutaraldehyde and consequently TL lipase enzyme immobilization was carried out by a simple wet chemical method. The resulting assemblies were characterized by using techniques like XRD, UV absorption and photoluminescence spectroscopy. The particle size was determined by using Transmission Electron Microscopy (TEM). The immobilized TL lipase enzyme showed high activity for esterification of oleic acid (C-18) with methanol in an organic medium. The catalyst was recovered and reused several times without any significant loss of activity.
- Shah, Ekta,Mahapatra, Paramita,Bedekar, Ashutosh V.,Soni, Hemant P.
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- Transesterification catalyzed by superhydrophobic-oleophilic mesoporous polymeric solid acids: An efficient route for production of biodiesel
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We report here an efficient mesoporous polymeric solid acid catalyst (p-PDVB-SO3H) with superhydrophobic-oleophilic properties synthesized from copolymerization of divinylbenzene (DVB) with sodium p-styrene sulfonate under solvothermal conditions. N2 isotherm showed that p-PDVB-SO 3H has large BET surface area and uniform mesopore. Contact angle tests showed that p-PDVB-SO3H exhibits superhydrophobic-oleophilic property for triolein and methanol, which results in its good miscibility and high exposition degree of active sites for various organic reactants. Catalytic tests showed that p-PDVB-SO3H has much better catalytic activities and recyclability toward transesterification to biodiesel than those of H-form mesoporous ZMS-5 zeolite, carbon solid acid and commercially acidic resin of Amberlyst 15, which will be very important for its wide applications for biodiesel production in industry.
- Noshadi, Iman,Kumar, Ranjan Kamat,Kanjilal, Baishali,Parnas, Richard,Liu, Hua,Li, Jiantao,Liu, Fujian
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- α,ω-functionalized C19 monomers
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High-oleic sunflower oil, a renewable resource, is efficiently incorporated into a sustainable and green chemical process: the synthesis of α,ω-functionalized C19 monomers. These monomers, derived from dimethyl 1,19-nonadecanedioate as a novel platform chemical, may find use as feedstock materials for the polymer industry.
- Walther, Guido,Deutsch, Jens,Martin, Andreas,Baumann, Franz-Erich,Fridag, Dirk,Franke, Robert,K?ckritz, Angela
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- Synthesis of aminimides derived from oleic acid: a new family of drag-reducing surfactants
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Large-scale syntheses of aminimide surfactants that serve as low temperature drag-reducing agents in ethylene glycol-water mixtures are described. Preliminary drag reduction results are presented and the susceptibility of the surfactants to methanolysis is discussed.
- Oba, Gabriel,Coleman, Bridgett E.,Hart, David J.,Zakin, Jacques,Zhang, Ying,Kawaguchi, Yasuo,Talmon, Yeshayahu
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- 9(Z)-Octadecenamide and Fatty Amides by Bacillus megaterium (B-3437) Conversion of Oleic Acid
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9(Z)-Octadecenamide, hexadecenamide, tetradecenamide and tetradecanamide were produced by a novel bioconversion of oleic acid with Bacillus megaterium NRRL B-3437.Although chemical synthesis is more practical, the bioconversion to fatty amides (5-7percent of total recovered lipids) was unique for its requirement of both enzymatic catalysis and equimolar oleic acid / ammonium salt substrates.Purified octadecenamide was obtained by silica gel and high-pressure liquid chromatographic procedures and was characterized by gas chromatography, mass spectrometry, infrared and nuclear magnetic resonance.KEY WORDS: Bacillus megaterium (B-3437), bioconversion, fatty amides, hexadecenamide, 9(Z)-octadecenamide, oleic acid.
- Kaneshiro, T.,Vesonder, R. F.,Peterson, R. E.,Weisleder, D.,Bagby, M. O.
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- Isomerizing olefin metathesis as a strategy to access defined distributions of unsaturated compounds from fatty acids
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The dimeric palladium(I) complex [Pd(μ-Br)tBu 3P]2 was found to possess unique activity for the catalytic double-bond migration within unsaturated compounds. This isomerization catalyst is fully compatible with state-of-the-art olefin metathesis catalysts. In the presence of bifunctional catalyst systems consisting of [Pd(μ-Br)tBu3P]2 and NHC-indylidene ruthenium complexes, unsaturated compounds are continuously converted into equilibrium mixtures of double-bond isomers, which concurrently undergo catalytic olefin metathesis. Using such highly active catalyst systems, the isomerizing olefin metathesis becomes an efficient way to access defined distributions of unsaturated compounds from olefinic substrates. Computational models were designed to predict the outcome of such reactions. The synthetic utility of isomerizing metatheses is demonstrated by various new applications. Thus, the isomerizing self-metathesis of oleic and other fatty acids and esters provides olefins along with unsaturated mono- and dicarboxylates in distributions with adjustable widths. The cross-metathesis of two olefins with different chain lengths leads to regular distributions with a mean chain length that depends on the chain length of both starting materials and their ratio. The cross-metathesis of oleic acid with ethylene serves to access olefin blends with mean chain lengths below 18 carbons, while its analogous reaction with hex-3-enedioic acid gives unsaturated dicarboxylic acids with adjustable mean chain lengths as major products. Overall, the concept of isomerizing metatheses promises to open up new synthetic opportunities for the incorporation of oleochemicals as renewable feedstocks into the chemical value chain.
- Ohlmann, Dominik M.,Tschauder, Nicole,Stockis, Jean-Pierre,Gooben, Kaethe,Dierker, Markus,Gooben, Lukas J.
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- A green approach for enhancing the hydrophobicity of UiO-66(Zr) catalysts for biodiesel production at 298 K
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Recently, the incorporation of hydrophobicity on the surface of UiO-66(Zr) has received much attention due to the deactivation of hydrophilic active sites of UiO-66(Zr) upon water adsorption. In this work, we report UiO-66(Zr) catalysts with an assortment of surface hydrophobicities fabricated by the solvent-free method to elucidate the impact of the environment framing Lewis acid sites on their catalytic activity in the production of fatty acid methyl ester (biodiesel) via the esterification of fatty acids at room temperature with high selectivity (100%) and good recyclability. A detailed structural analysis of the materials by N2 sorption, FT-IR, SEM, XRD, water contact angle measurement, dynamic liquid scattering (DLS), NMR and TGA revealed the fabrication of stearic acid-grafted UiO-66(Zr) catalysts (10SA/UiO-66) with fine particle size and a highly hydrophobic network. 10SA/UiO-66(Zr) with enhanced hydrophobicity exhibited superior catalytic performance in the esterification of a fatty acid with a long alkyl chain compared with conventional solid acid catalysts and even liquid acid catalysts. Detailed kinetic studies corroborated that the adsorption of lipophilic acids at the Lewis acid sites besides the enhancement of wettability between the reactants was facilitated by the hydrophobic environment, thus significantly motivating the esterification reaction at room temperature. Furthermore, 10SA/UiO-66(Zr) showed good catalytic activity in the esterification of oleic acid in the presence of water (~10% in the light of acid weight).
- Abou-Elyazed, Ahmed S.,El-Nahas, Ahmed M.,Sun, Yinyong,Yousif, Ahmed M.
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- Transesterification of vegetable oil with subcritical methanol using heterogeneous transition metal oxide catalysts
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Transesterification of vegetable oil with subcritical methanol over newly-developed heterogeneous Mn catalysts for the production of biodiesel fuel is reported. The dense CH3OH can improve the catalytic performance as a result of the effective removal of the reaction products with methylation of the intermediate carboxylates on the catalyst surface.
- Oku, Tomoharu,Nonoguchi, Masanori,Moriguchi, Toshimitsu,Izumi, Hiroko,Tachibana, Atsushi,Akatsuka, Takeo
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- Transesterification of triolein to biodiesel fuel over mordenite-supported CaO catalysts
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CaO catalysts supported on several metal oxides and zeolites were investigated for transesterification of triolein with methanol. Zeolite-supported CaO catalysts showed high catalytic activity for transesterification compared to the metal oxide-supported CaO catalysts; among the zeolites tested in this work, mordenite exhibited the best support. The catalytic activity of mordenite-supported CaO catalyst depended on both the amount of CaO loading and the calcination temperature for catalyst precursor.
- Yamaguchi, Syuhei,Asamoto, Makiko,Inoue, Syun,Kawahito, Satomi,Mieno, Yasuhiro,Ikushima, Kenji,Yahiro, Hidenori
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- Semiconductor Photocatalysis. Cis-Trans Photoisomerization of Simple Alkenes Induced by Trapped Holes at Surface States
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The use of ZnS or CdS as photocatalysts induces an efficient cis-trans photoisomerization of simple alkenes, e.g., the 2-octenes, 3-hexen-1-ols, and methyl 9-octadecenoates in photostationary cis-trans ratios almost identical with the thermodynamic equilibrium ratios achieved by the phenylthio radical.Quantum yields for the cis-trans photoisomerization, Φc-t, exceed largely over unity.Mechanistic studies involving Stern-Volmer analyses, quenching effect of oxygen, and ESR analysis under band-gap irradiation on ZnS in methanol demonstrate that the photoisomerizations take place with high turnover numbers at active sites where trapped holes at surface states, i.e., sulfur radicals arising from Zn vacancies and/or interstitial sulfur on sulfide semiconductors, play decesive roles.A highly efficient catalysis occurs with ZnS sols prepared from polysulfide-containing Na2S solution.The trapped-hole mechanism is further supported by the enhanced effect of water acting as a good electron acceptor as well as the quenching effect of diethylamine acting as an electron donor.
- Yanagida, Shozo,Mizumoto, Kunihiko,Pac, Chyongjin
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- ISOLATION OF INDIVIDUAL TYPE II CYANOLIPIDS FROM NEPHELIUM LAPPACEUM
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Three kinds of type II cyanolipids were isolated as pure forms from Nephelium lappaceum using HPLC.The full structures were established by spectral and chemical investigations. - Key Word Index: Nephelium lappaceum; Sapindaceae; seeds; type II cyanolipids; HPLC purification.
- Nishizawa, Mugio,Adachi, Kenji,Sastrapradja, Setijati,Hayashi, Yuji
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- Lipase-Catalysed Esterification of Oleic Acid and Methanol in Hexane - A Kinetic Study
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The kinetics of immobilized lipase-catalyzed esterification of oleic acid and methanol in hexane were investigated.The reaction follows Michaelis-Menton kinetics as observed from the relationship of initial rate of the reaction, both as a function of enzyme and of substrate concentration.Inhibition by excess of methanol has been identified.The kinetic constants have been measured for the reaction in the absence of any significant external diffusional limitations.The kinetics of the enzymatic reaction are suggested to agree with a Ping-Pong Bi Bi mechanism.KEY WORDS: Ester synthesis, esterification, immobilized lipase, kinetics, oleic acid, Ping-Pong Bi Bi mechanism.
- Ramamurthi, Suresh,McCurdy, Alan R.
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- SELECTIVE CATALYTIC HYDROGENATION OF 1,4-DIENES TO cis-MONOENES USING (NAPHTHALENE)(TRICARBONYL)CHROMIUM
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Methylene interrupted dienes react with (naphthalene)(tricarbonyl)chromium under H2 to yield a mixture of positionally isomeric cis-monoene products.The isomer distribution, reactions with proposed organic intermediates, and kinetic studies suggest a mechanistic pathway that includes (1) loss of the arene from the metal fragment, (2) isomerization of the 1,4 diene to 1,3 conjugated dienes, and (3) subsequent reduction of the conjugated dienes to the isomeric cis-monoene products.The active metal fragment appeares to be selective in the isomerisation of 1,4 to 1,3 dienes and inert toward cis to trans geometrical isomerization of the monoene products.The results of kinetic studies using methyl cis,cis-9,12-octadienoate (methyl linoleate) as a substrate for the hydrogenation reactions are discussed.
- Tucker, James R.,Riley, Dennis P.
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- Characterization of markers of botanical origin and other compounds extracted from unifloral honeys
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The possibility of tracing the botanical and geographical origin of products such as honey has become more important because of market globalization. As a consequence, numerous analytical methods have been applied to the determination of honey authenticity. The scope of the present work is to chromatographically purify and characterize 23 compounds from organic extracts of unifloral (chestnut, linden, orange, acacia, eucalyptus, honeydew) and polyfloral honeys. Of these compounds, 17 were identified as specific markers and were used for botanical discrimination in a previous study based on multivariate statistical analysis of proton nuclear magnetic resonance ( 1H NMR) data. Together with the botanical markers, 6 other substances were isolated and characterized using NMR and mass spectrometry. These phytochemicals belong to several classes, that is, terpenes, organic acids, flavonoids, and others. For the first time, a diacylglyceryl ether and 5 other compounds present in different types of honey were identified and characterized.
- Schievano, Elisabetta,Morelato, Elisa,Facchin, Chiara,Mammi, Stefano
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- Evaluation of diatomaceous earth supported lipase sol-gels as a medium for enzymatic transesterification of biodiesel
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Immobilized lipase has the potential to be the catalyst of choice for biodiesel production since it is efficient, effective, and environmentally friendly; however, the stability and activity of lipase must be addressed before enzymatic biodiesel production processes can be industrially accepted. This study investigates an enzyme immobilization procedure that immobilizes lipase in a sol-gel supported on diatomaceous earth (Celite R632), and determines its potential for biodiesel production in terms of achievable conversion and apparent stability. Four immobilized materials (lipase sol-gels with and without Celite at two protein loading levels) were compared in terms of their immobilized protein content, conversion of methanol to methyl oleate, lipase activity, long term stability, and glycerol-water adsorption. The Celite R632 sol-gel with high protein loading achieved the maximum conversion in the 6-h reaction period (90%). A drying step was found to be advantageous prior to the reaction, and the absorption of glycerol-water on the Celite was only found to be significant at high levels of glycerol. The material was found to be very stable upon storage at 4 °C for up to 1.5 years, losing only about 15% of its percent conversion capacity per year. Based on this study, the supported immobilization technique shows significant potential as a novel catalyst for biodiesel production.
- Meunier,Legge
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- Facile route to conformal hydrotalcite coatings over complex architectures: A hierarchically ordered nanoporous base catalyst for FAME production
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An alkali- and nitrate-free hydrotalcite coating has been grafted onto the surface of a hierarchically ordered macroporous-mesoporous SBA-15 template via stepwise growth of conformal alumina adlayers and their subsequent reaction with magnesium methoxide. The resulting low dimensional hydrotalcite crystallites exhibit excellent per site activity for the base catalysed transesterification of glyceryl triolein with methanol for FAME production.
- Creasey, Julia J.,Parlett, Christopher M. A.,Manayil, Jinesh C.,Isaacs, Mark A.,Wilson,Lee, Adam F.
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- Stereoselective synthesis of isomers of the naturally occurring 13-hydroxy-2,4,9-tetradecatrienoic acid. Part II [1]
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The stereoselective syntheses of four unsaturated hydroxy fatty acids (13S,2E,4E,9E)-13-hydroxy-2,4,9-tetradecatrienoic acid, (13S,9Z,11E)-13-hydroxy- 9,11-tetradecadienoic acid, (13S,9E, 11E)-13-hydroxy-9,11-tetradecadienoic acid, and (13S,2E,4E,9E)-13-hydroxy-2,4,9,11-tetradecatrienoic acid, are described. Wittig reactions, regioselective oxidation of dialcohol 3, and diastereomerization were used. Springer-Verlag 2004.
- Huefner, Antje,Hoeller, Christa,Reznicek, Gottfried
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- ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS
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An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.
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Paragraph 0010; 0026
(2021/01/29)
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- Branched alkyl sulfonate anionic surfactant and preparation process thereof
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The invention discloses a branched alkyl sulfonate anionic surfactant and a preparation process thereof, and belongs to the field of fine chemical surfactants. The method comprises the steps of (1) conducting a esterification carboxyl-terminated reaction, specifically, catalyzing oleic acid or linoleic acid and fatty alcohol to be subjected to esterification reaction by adopting organic acid as acatalyst to prepare an alkyl oleate or alkyl linoleate compound; and (2) conducting a double bond addition sulfonation reaction, specifically, in the presence of the catalyst, carrying out sulfonationreaction with the alkyl oleate compound or the alkyl linoleate compound obtained in the step (1) by taking low-carbon alcohol and deionized water as solvents and sodium hydrogen sulfite as a sulfonation reagent to prepare the branched alkyl sulfonate anionic surfactant. The synthesized branched alkyl sulfonate anionic surfactant product can effectively reduce the surface tension of an aqueous solution, and is good in solubility, large in initial foaming amount, high in defoaming speed and excellent in surfactant performance. The method has the advantages of simple process operation, few sidereactions, energy saving and environmental protection.
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Paragraph 0041-0042; 0068-0069
(2021/02/10)
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- Identification and α -Glucosidase Inhibitory Activity of Meroterpenoids from Hericium erinaceus
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Hericium erinaceus is a very popular edible and medicinal mushroom used for the treatment of enervation and gastrointestinal diseases in Eastern Asia. Chemical investigation on the fruiting body of Hericium erinaceus led to the isolation of 4 new (1 - 4) and 10 known meroterpenoids (5 - 14). The structures of new compounds were determined via analysis of NMR and MS data in combination with chemical derivatization. The inhibitory activities of 1 - 14 against α -glucosidase were evaluated using p -nitrophenyl- α -D-glucopyranoside, sucrose, or maltose as substrate. Compounds 6, 9, 11 - 13 were demonstrated to show the α -glucosidase inhibitory activities. This work confirms the potential of H. erinaceus in the treatment of diabetes.
- Bao, Li,Chen, Baosong,Han, Junjie,Liu, Hongwei,Ma, Ke,Wang, Wenzhao
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p. 571 - 578
(2020/06/03)
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- Synthesis, ADME, docking studies and in vivo anti-hyperglycaemic potential estimation of novel Schiff base derivatives from octadec-9-enoic acid
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A new series of octadec-9-enoic acid schiff base entities (S1-S30) were designed and synthesized targeting peroxisome proliferator activated receptor-gamma for agonist action. Molinspiration software (online) was used to estimate drug like molecular properties of the metabolites. Docking disquisition on co-crystallized protein of PPAR-γ (PDB ID 1FM9) was carried out which showed S21, S10 and S7 as best situated in the vital sites of receptor having docking scores ?9.19, ?8.68 and ?8.64 respectively. Free binding energy measured using model of Maestro 9.0 and was in range of from ?40.01 and ?80.54 kcal/mol, significant when compared with pioglitazone (?51.58 Kcal/mol). Seven best docked derivatives were assessed for in-vivo oral glucose tolerance on normal rats and anti-hyperglycaemic activity by streptozotocin induced diabetes model. S21 unveiled to be the best measured analogue among all the synthesized entities. Encouraging outcomes motivates fatty acids for further development of more effective and safer compounds.
- Kapoor, Garima,Pathak, Dharam Pal,Bhutani, Rubina,Husain, Asif,Jain, Sandeep,Iqbal, Md. Azhar
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p. 478 - 492
(2019/01/04)
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- Method for preparing environment-friendly plasticizer from waste grease and application of method
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The invention discloses a method for preparing an environment-friendly plasticizer from waste grease and an application of the method, and belongs to the field of fine chemical synthesis and plastic additive application. According to the invention, higher fatty acid purified from waste grease, methanol, 50% hydrogen peroxide, trimellitic anhydride and acetic anhydride are adopted as main raw materials, and molecular structure modification and functional group conversion are carried out through four steps of reactions comprising esterification, epoxidation, ring-opening esterification and acetylation, so that the environment-friendly plasticizer product acetyl fatty acid methyl ester-triphenyl trimellitate is prepared. The environment-friendly plasticizer product prepared by the method hasthe characteristics of combination of cyclic molecules and linear molecules, is moderate in viscosity, yellow in color and relatively good in migration resistance and heat resistance, is suitable forindustrial production, and is expected to replace traditional phthalate plasticizers.
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Paragraph 0022; 0024
(2020/01/12)
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- Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis
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A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic moiety interacting with the carbonyl substrates through nonclassical hydrogen bonding. The reaction can be applied to large-scale synthesis of biodiesel under mild conditions.
- Lam, Ying-Pong,Ng, Wing-Hin,Tan, Fei,Tse, Ying-Lung Steve,Wang, Xinyan,Yeung, Ying-Yeung
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p. 8083 - 8092
(2019/08/26)
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- Catalytic transfer hydrogenation of oleic acid to octadecanol over magnetic recoverable cobalt catalysts
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Efficient transformation of biomass into fuel and chemicals under mild conditions with cost-effective and environmentally friendly characters is highly desirable but still challenging. Herein, a scalable and Earth-abundant cobalt catalyst was used for selective catalytic transfer hydrogenation (CTH) of unsaturated fatty acids to fatty alcohols with sustainable isopropanol as a hydrogen donor. By tuning the surface Co composition by varying the reduction temperature, the catalytic performance could be easily boosted. At 200 °C in 4 h, the optimal catalyst Co-350 (reduced at 350 °C) gives 100% oleic acid conversion with 91.9% octadecanol selectivity. Various characterization studies reveal that the co-existence of Coδ+ and Co0 over the cobalt core might be responsible for its high performance for CTH of oleic acid. This catalyst could be magnetically separated and is highly stable for reusing ten times. Moreover, this cobalt catalyst is relatively cheap and easy to scale-up, thus achieving a low-cost transformation of biomass into high value-added chemicals.
- Wang, Juncheng,Nie, Renfeng,Xu, Ling,Lyu, Xilei,Lu, Xiuyang
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p. 314 - 320
(2019/01/28)
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- Synthesis method of disodium oleate
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The invention relates to a synthesis method of disodium oleate. The synthesis method of the disodium oleate comprises the following steps: performing reaction on oleic acid, methanol and p-toluenesulfonic acid to obtain methyl oleate; performing addition on the methyl oleate and ethylene oxide to obtain methyl oleate ethoxylate; and performing sulfonated addition reaction on an intermediate product and sodium hydrogen sulfite to obtain methyl oleate ethoxylate sulfonate, performing saponification reaction, and performing extraction and separation on ethyl acetate and a saturated sodium chloride aqueous solution of 30 percent by weight to obtain the disodium oleate. The synthesis method of the disodium oleate has the following advantages: the raw materials are rich and can be regenerated, and the sulfonation rate is high; the solvent used in the preparation process is cheap, easily available and recyclable; and reaction is mild, energy consumption is low, sulfonation rate is high and yield is high.
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Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031; 0032
(2018/09/20)
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- Zirconocene-catalysed biodiesel synthesis from vegetable oil with high free fatty acid contents
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A highly efficient transformation of vegetable oils into biodiesel catalysed by air-stable and water-tolerant zirconocene perfluorooctanesulfonate Lewis acid has been developed. By combining the direct esterification of free fatty acids (FFAs) and transesterification of triglycerides (TGs), the simultaneous transformation of the two components to biodiesel is achieved in good yields. Furthermore, this catalyst, when used in the synthesis of biodiesel from commercial oleifera, behaves as a reaction-induced self-separation catalyst. During the course of the reaction, it switches from homogeneous to heterogeneous; upon completion of the reaction, the catalyst precipitates as a white solid, which can be easily recycled.
- Deng, Yiqiang,Hu, Xiaojian,Cheng, Lihua,Wang, Hanlu,Duan, Linhai,Qiu, Renhua
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p. 116 - 120
(2018/07/06)
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- Identification of new diterpene esters from green Arabica coffee beans, and their platelet aggregation accelerating activities
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Eight new ent-kaurane diterpene fatty acid esters, namely caffarolides A–H (1–8), were isolated from green beans of Coffea arabica. Their chemical structures were confirmed by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, 1
- Wang, Xia,Meng, QianQian,Peng, XingRong,Hu, GuiLin,Qiu, MingHua
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p. 251 - 257
(2018/05/23)
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- Methanolysis of Jatropha curcas oil using K2CO3/CaO as a solid base catalyst
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Biodiesel, fatty acid methyl ester produced by the transesterification of vegetable oil with methanol, is a promising alternative to petroleum-based diesel fuel. In the present study, the methanolysis of high free fatty acid (FFA) Jatropha curcas oil in a transesterification reaction using K 2 CO 3 /CaO solid base catalyst was studied. The various reaction parameters in the transesterification reaction were also discussed. The catalyst was characterized by means of Fourier transform infrared, X-ray diffraction, temperature programmed desorption of CO 2, scanning electron microscopy, particle size analyzer, true density, and surface area analyzer. The optimum conversion of jatropha oil was 92% when the transesterification reaction was carried out at 70? C with 10:1 molar ratio of methanol to oil at reaction time of 3 h and catalyst amount of 6 wt%. The efficiency of catalysts in the methanolysis of jatropha oil was also investigated.
- Sahu, Gajanan,Saha, Sujan,Datta, Sudipta,Chavan, Prakash,Naik, Satyanarayan
-
p. 845 - 861
(2018/01/12)
-
- Revealing the Roles of Subdomains in the Catalytic Behavior of Lipases/Acyltransferases Homologous to CpLIP2 through Rational Design of Chimeric Enzymes
-
The lipases/acyltransferases homologous to CpLIP2 of Candida parapsilosis efficiently catalyze acyltransfer reactions in lipid/water media with high water activity (aW>0.9). Two new enzymes of this family, CduLAc from Candida dubliniensis and CalLAc8 from Candida albicans, were characterized. Despite 82 % sequence identity, the two enzymes have significant differences in their catalytic behaviors. In order to understand the roles played by the different subdomains of these proteins (main core, cap and C-terminal flap), chimeric enzymes were designed by rational exchange of cap and C-terminal flap, between CduLAc and CalLAc8. The results show that the cap region plays a significant role in substrate specificity; the main core was found to be the most important part of the protein for acyltransfer ability. Similar exchanges were made with CAL-A from Candida antarctica, but only the C-terminal exchange was successful. Yet, the role of this domain was not clearly elucidated, other than that it is essential for activity.
- Jan, Anne-Hélène,Dubreucq, éric,Subileau, Maeva
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p. 941 - 950
(2017/05/26)
-
- Inflammation Modulatory Phorbol Esters from the Seeds of Aquilaria malaccensis
-
The tree Aquilaria malaccensis is a valuable source of agarwood, which is used in herbal medicinal preparations. Phytochemical research on A. malaccensis seeds has led to the isolation of four new phorbol esters (1-4), two known phorbol esters (5, isolated from Nature for the first time, and 6), and two known glycerides (7 and 8). The structures of these isolates were elucidated by means of spectroscopic data interpretation. The inflammation-modulatory activities of the isolates on elastase release and superoxide anion generation in human neutrophils were evaluated. Interestingly, phorbol esters 1, 5, and 6 showed potent inhibitory activity on elastase release in human neutrophils, with IC50 values of 2.7, 0.8, and 2.1 μM, respectively. All isolated phorbol esters exerted enhancing activity on superoxide anion generation. The results indicated that phorbol esters may play a bilateral modulatory role in the processes of inflammation. In addition, the compounds were evaluated for their cytotoxic properties against HepG2 (hepatoma), MDA-MB-231 (breast), and A549 (lung) cancer cells, but all compounds were inactive for all cell lines used (IC50 > 10 μM).
- Wagh, Vitthal D.,Korinek, Michal,Lo, I-Wen,Hsu, Yu-Ming,Chen, Shu-Li,Hsu, Hsue-Yin,Hwang, Tsong-Long,Wu, Yang-Chang,Chen, Bing-Hung,Cheng, Yuan-Bin,Chang, Fang-Rong
-
p. 1421 - 1427
(2017/06/01)
-
- Sulfonated porous organic polymer as a highly efficient catalyst for the synthesis of biodiesel at room temperature
-
A new functionalized porous organic polymer bearing sulfonic acid groups (PDVTA-SO3H) at the pore surface with high surface area (SBET = 406 m2 g-1) and Bronsted acidity is reported. The material has been synthesized via post-synthetic sulfonation of the porous co-polymer poly-divinylbenzene-co-triallylamine (PDVTA-1) using chlorosulfonic acid as sulfonating agent. A detailed characterization of the -SO3H functionalized porous polymeric material has been carried out using N2 sorption, FT-IR and UV-vis spectroscopy, HR-TEM, FE-SEM, thermogravimetric and elemental analyses. Temperature programmed desorption of NH3 (TPD-NH3 analysis) of PDVTA-SO3H revealed a very high surface acidity of 2.3 mmol g-1. Such high acidity of PDVTA-SO3H has been explored to investigate its catalytic efficiency towards eco-friendly production of biodiesel via esterification of long-chain free fatty acids (FFA) to the respective fatty acid monoalkyl esters (FAMEs) at room temperature using methanol as reactant as well as solvent. The sulfonated porous polymer is found to be a very active and reusable solid acid catalyst giving high yields (~92-98%) of various biodiesel compounds under very mild reaction conditions.
- Gomes, Ruth,Bhanja, Piyali,Bhaumik, Asim
-
p. 110 - 116
(2015/11/11)
-
- A rapid and sensitive profiling of free fatty acids using liquid chromatography electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) after chemical derivatization
-
Free fatty acids (FFAs) have diverse roles in cellular energy and signaling and they are critical molecules in various biological states. Due to the poor ionization efficiency of FFAs under electrospray ionization mass spectrometry (ESI-MS) conditions, it is a challenging aspect to construct a robust platform for profiling of various FFAs in biological samples using liquid chromatography ESI-MS. In the present study, we applied trimethylsilyldiazomethane (TMSD) derivatization to improve ionization efficiencies in the profiling of FFAs. Multiple reaction monitoring (MRM) was used for the selective quantification of methylated FFAs. The optimal TMSD methylation was validated for a reliable FFA profiling. Furthermore, the high-throughput analysis of FFAs was successfully performed in short analysis and derivatization times. To verify the utility and effectiveness of the developed method, we compared both methylation and nonmethylation (intact FFA) data in the profiling of FFAs in mice liver and plasma. It is noteworthy that the methylation derivatization provided better results in FFA profiling. Further, we performed statistical data analysis where HBV and mock mice tissues were discriminated when the methylated FFAs data were used. In the lipidomics field, the present method can also be applied for the profiling of FFAs in biological samples for biomarker discovery. The present validated LC/ESI-MS/MS assay method may also be used for FFA profiling modeling studies in other biomedical samples.
- Mok, Hyuck Jun,Lee, Jae Won,Bandu, Raju,Kang, Hong Seok,Kim, Kyun-Hwan,Kim, Kwang Pyo
-
p. 32130 - 32139
(2016/05/09)
-
- Four new phorbol diesters from Croton tiglium and their cytotoxic activities
-
Phytochemical investigation of the seeds of Croton tiglium resulted in the isolation and structure elucidation of four new 4-deoxy-4β-phorbol diesters (1-4) named as 12-O-tiglylphorbol-4-deoxy-4β-phorbol-13-acetate (1), 12-O-tiglylphorbol-4-deoxy-4β-phorbol-13-hexadecanoate (2), 13-O-acetylphorbol-4-deoxy-4β-phorbol-20-oleate (3) and 13-O-acetylphorbol-4-deoxy-4β-phorbol-20-linoleate (4), respectively. The structures of the new compounds were established by 1D, 2D-NMR and HR-ESI-MS spectroscopic data and chemical degradation experiments. The cytotoxic activities of compounds 1-4 were evaluated against hepatic tumor cell lines (SNU387 and SNU398). Among these compounds, compound 4 exhibited the most potent activity against the SNU387 with IC50 value of 0.71 μM.
- Zhang, Xiao-Long,Khan, Ashfaq-Ahmad,Wang, Lun,Yu, Kai,Li, Fu,Wang, Ming-Kui
-
-
- Cytotoxic ceramides from the Red Sea sponge Spheciospongia vagabunda
-
Extracts of Egyptian marine organisms from the Red Sea were screened for their anticancer activity using sulforhodamine B assay. The extract of the Red Sea sponge Spheciospongia vagabunda possessed promising anticancer activity against HepG2 (liver cancer cell line) and MCF-7 (breast cancer cell line). Isolation of three new ceramides: N-[(2S,3S,4R)-1,3,4-trihydroxytetradecan-2-yl] tridecanamide (1), (R)-2′-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxypentacosan-2-yl] octadecanamide (2) and (R,Z)-2′-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxytricosan-2-yl) nonadec-10-enamide (3) was accomplished via bioassay-guided fractionation. Structure elucidation was achieved using spectroscopic techniques, including 1D and 2D NMR and HRMS. Compounds 2 and 3 displayed high potential cytotoxicity against HepG2 (IC50 24.7 and 21.3 μM, respectively) and MCF-7 (IC50 26.8 and 29.8 μM, respectively), compared with doxorubicin as control drug.
- Eltamany, Enas Elsayed,Ibrahim, Amany K.,Radwan, Mohamed M.,Elsohly, Mahmoud A.,Hassanean, Hashim A.,Ahmed, Safwat A.
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p. 3467 - 3473
(2015/08/03)
-
- SO3H and NH2+ functional carbon-based solid acid catalyzed transesterification and biodiesel production
-
A SO3H and NH2+ functional carbon-based solid acid was used as a highly active heterogeneous catalyst for the transesterification of various carboxylic methyl esters with alcohols under mild conditions. It also showed high catalytic performance for transesterification of triolein with methanol or isopropanol. Furthermore, it was able to catalyze simultaneous esterification and transesterification of rice oil and butter respectively, the yields of biodiesel obtained were up to 94%, and the catalyst could be easily recovered and reused more than ten times without loss of activity, which indicated the carbon-based solid acid was a potential catalyst for the biodiesel industry.
- Cai, Liangzhen,Meng, Decai,Zhan, Shaoqi,Yang, Xiaoxia,Liu, Taoping,Pu, Huiming,Tao, Xiaochun
-
p. 72146 - 72149
(2015/09/08)
-
- Electrochemistry for biofuel generation: Transformation of fatty acids and triglycerides to diesel-like olefin/ether mixtures and olefins
-
Abstract Electroorganic synthesis can be exploited for the production of biofuels from fatty acids and triglycerides. With Coulomb efficiencies (CE) of up to 50%, the electrochemical decarboxylation of fatty acids in methanolic and ethanolic solutions leads to the formation of diesel-like olefin/ether mixtures. Triglycerides can be directly converted in aqueous solutions by using sonoelectrochemistry, with olefins as the main products (with a CE of more than 20%). The latter reaction, however, is terminated at around 50% substrate conversion by the produced side-product glycerol. An energy analysis shows that the electrochemical olefin synthesis can be an energetically competitive, sustainable, and - in comparison with established processes - economically feasible alternative for the exploitation of fats and oils for biofuel production. From fat to fuel: Electrochemical decarboxylation of fatty acids and triglycerides leads to the formation of olefins and ethers (see scheme). This electroorganic synthesis is an energetically competitive, sustainable, and economically feasible alternative for the exploitation of fats and oils for biofuel production.
- Dos Santos, Tatiane R.,Harnisch, Falk,Nilges, Peter,Schr?der, Uwe
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p. 886 - 893
(2015/06/02)
-
- Green bioprocesses in sponge-like ionic liquids
-
Abstract Ionic liquids (ILs) are a new class of liquid solvent, whose use has led to a green chemical revolution because of their unique array of physico-chemical properties, headed by their negligible vapour pressure and their exceptional ability to stabilize biocatalysts. Hydrophobic ILs based on cations with long alkyl side-chains, e.g. N,N,N,N-hexadecyltrimethylammonium bis(trifluoromethylsulfonyl)imide ([C16tma][NTf2]), are temperature switchable ionic liquid/solid phases that behave as sponge-like systems (sponge-like ionic liquid, SLILs). Based on this new property, SLILs have been used to develop straightforward and clean approaches for producing nearly pure synthetic compounds with added value (e.g. geranyl acetate, anisyl acetate, methyl oleate, etc.) in two steps: an enzymatic synthetic step as liquid phase, and then a product separation step involving simple centrifugation as a solid phase.
- Lozano, Pedro,Bernal, Juana M.,Gómez, Celia,García-Verdugo, Eduardo,Isabel Burguete,Sánchez, Gregorio,Vaultier, Michel,Luis, Santiago V.
-
-
- The 3D model of the lipase/acyltransferase from Candida parapsilosis, a tool for the elucidation of structural determinants in CAL-A lipase superfamily
-
Abstract Because lipids are hydrophobic, the development of efficient bioconversions in aqueous media free of organic solvents is particularly challenging for green oleochemistry. Within this aim, enzymes exhibiting various abilities to catalyze acyltransfer reaction in water/lipid systems have been identified. Among these, CpLIP2 from Candida parapsilosis has been characterized as a lipase/acyltransferase, able to catalyze acyltransfer reactions preferentially to hydrolysis in the presence of particularly low acyl acceptor concentration and high thermodynamic activity of water (aw > 0.9). Lipase/acyltransferases are thus of great interest, being able to produce new esters at concentrations above the thermodynamic equilibrium of hydrolysis/esterification with limited to no release of free fatty acids. Here, we present a 3D model of CpLIP2 based on homologies with crystallographic structures of Pseudozyma antarctica lipase A. Indeed, the two enzymes have 31% of identity in their primary sequence, yielding a same general structure, but different catalytic properties. The quality of the calculated CpLIP2 model was confirmed by several methods. Limited proteolysis confirmed the location of some loops at the surface of the protein 3D model. Directed mutagenesis also supported the structural model constructed on CAL-A template: the functional properties of various mutants were consistent with their structure-based putative involvement in the oxyanion hole, substrate specificity, acyltransfer or hydrolysis catalysis and structural stability. The CpLIP2 3D model, in comparison with CAL-A 3D structure, brings insights for the elucidation and improvement of the structural determinants involved in the exceptional acyltransferase properties of this promising biocatalyst and of homologous enzymes of the same family.
- Subileau, Maeva,Jan, Anne-Hélène,Nozac'h, Hervé,Pérez-Gordo, Marina,Perrier, Véronique,Dubreucq, Eric
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p. 1400 - 1411
(2015/08/03)
-
- GC-FID analysis of fatty acids and biological activity of Zanthoxylum rhetsa (Roxb.) DC seed oil
-
The Fatty acid content and composition of fixed oil from Zanthoxylum rhetsa seeds was determined. The seeds were found to contain about ~19.5% of crude fixed oil on a dry weight basis. Fatty acids were converted into methyl esters and analyzed by GC-FID. Ten fatty acids were identified using GC-FID. The major monounsaturated and saturated fatty acids were oleic acid (41.6 - 43.5%) and palmitic acid (26.8-30.2%) respectively, whereas the α-linolenic acid (12.1 - 12.5%) and linoleic acid (10.0%) were polyunsaturated fatty acid. Stearic acid (5.2 - 6.0%), myristic acid (0.1%), traces of pentadecanoic, heptadecanoic and arachidic acid were also identified. These fatty acids have not been reported earlier from the oil of Z. rhetsa. Fixed oil exhibited significant free radical scavenging activity which was measured using DPPH, and is also known to inhibit the gastrointestinal motility significantly.
- Naik, Rajashri R.
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p. 1929 - 1935
(2016/02/27)
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- Antitrypanosomal acetylene fatty acid derivatives from the seeds of Porcelia macrocarpa (Annonaceae)
-
Chagas' disease is caused by a parasitic protozoan and affects the poorest population in the world, causing high mortality and morbidity. As a result of the toxicity and long duration of current treatments, the discovery of novel and more efficacious drugs is crucial. In this work, the hexane extract from seeds of Porcelia macrocarpa R.E. Fries (Annonaceae) displayed in vitro antitrypanosomal activity against trypomastigote forms of T. cruzi by the colorimetric MTT assay (IC50 of 65.44 μg/mL). Using chromatographic fractionation over SiO2, this extract afforded a fraction composed by one active compound (IC50 of 10.70 μg/mL), which was chemically characterized as 12,14-octadecadiynoic acid (macrocarpic acid). Additionally, two new inactive acetylene compounds (α,α′-dimacro-carpoyl-β-oleylglycerol and α-macrocarpoyl-α′-oleylglycerol) were also isolated from the hexane extract. The complete characterization of the isolated compounds was performed by analysis of NMR and MS data as well as preparation of derivatives.
- Santos, Luciana de á.,Cavalheiro, Alberto J.,Tempone, Andre G.,Correa, Daniela S.,Alexandre, Tatiana R.,Quintiliano, Natalia F.,Rodrigues-Oliveira, AndréF,Oliveira-Silva, Diogo,Martins, Roberto Carlos C.,Lago, Jo?o Henrique G.
-
p. 8168 - 8180
(2015/05/20)
-
- Application of metal triflate catalysts for the trans-esterification of Jatropha curcas L. oil with methanol and higher alcohols
-
This paper describes an experimental study on the application of metal triflate salts for the (trans-) esterification of fatty esters (triolein, methyl oleate, methyl linoleate), fatty acid (oleic acid), as well as Jatropha curcas L. oil with methanol and higher alcohols (ethanol, n-propanol, iso-propanol, iso-butanol, tert-butanol). The effect of the metal type (scandium, bismuth, aluminium, lanthanum, copper, zinc) and process conditions on reaction performance were evaluated. Highest conversions were obtained with Al(OTf) 3. Reaction of triolein with methanol gave 99 mol% conversion at 165 C for 1 h and the main product was the methyl ester. In addition, partial methoxylation of the carbon-carbon double bonds in the fatty acid chains was observed, though their fraction in the mixture was less than 20 mol%. The trans-esterification reaction was also successfully performed using higher alcohols, giving >95 % conversions for ethanol, n-propanol, iso-propanol and iso-butanol, whereas tert-butanol was not reactive. For the reaction of oleic acid with methanol, quantitative esterification, partial methoxylation of the carbon-carbon double bonds and the formation of small amounts of a lactone was observed. The methodology using Al(OTf)3 was successfully performed on the trans-esterification reaction of JO (FFA content of 2.1 wt%) with various alcohols. Key properties (viscosity, pour point and cloud points) of the (branched) Jatropha esters were determined. The best cold-flow properties were obtained for the iso-propyl esters of JO, with cloud point and pour point of -3 and -24 C, respectively.
- Daniel, Louis,Rasrendra, Carolus B.,Kloekhorst, Arjan,Broekhuis, Antonius A.,Manurung, Robert,Heeres, Hero J.
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p. 325 - 336
(2014/03/21)
-
- Alkali- and nitrate-free synthesis of highly active Mg-Al hydrotalcite-coated alumina for FAME production
-
Mg-Al hydrotalcite coatings have been grown on alumina via a novel alkali- and nitrate-free impregnation route and subsequent calcination and hydrothermal treatment. The resulting Mg-HT/Al2O3 catalysts significantly outperform conventional bulk hydrotalcites prepared via co-precipitation in the transesterification of C4-C18 triglycerides for fatty acid methyl ester (FAME) production, with rate enhancements increasing with alkyl chain length. This promotion is attributed to improved accessibility of bulky triglycerides to active surface base sites over the higher area alumina support compared to conventional hydrotalcites wherein many active sites are confined within the micropores.
- Creasey, Julia J.,Chieregato, Alessandro,Manayil, Jinesh C.,Parlett, Christopher M. A.,Wilson, Karen,Lee, Adam F.
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p. 861 - 870
(2014/03/21)
-
- Process to prepare a phosphorous containing vegetable oil based lubricant additive
-
Chemically-modified triglycerides are prepared by reacting epoxidized triglyceride oils with phosphorus-based acid hydroxide or esters. The phosphorus-containing triglyceride derivatives are of the formula: wherein R1″, R2″ and R3″ are independently selected from C3 to C29 aliphatic fatty acid residues, at least one of which comprising one or both of the derivatized methylene groups of the formula: wherein m is 0, 1 or 2, n is 0 or 1, q is 1, 2 or 3, and R and R′ are independently selected from the group consisting of H, straight, branched or cyclic hydrocarbons and substituted hydrocarbons, and aryl groups. The phosphorus-containing triglyceride derivatives so produced have utility as antiwear/antifriction additives for industrial oils and automotive applications.
- -
-
Page/Page column 9; 10; 11
(2014/09/16)
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- Mechanistic study of the synthesis of CdSe nanocrystals: Release of selenium
-
We outline a reaction pathway for the cleavage of the P=Se bond in trialkylphosphine selenide during the synthesis of CdSe nanocrystals. The reaction between cadmium carboxylate and trimethylphosphine selenide in the presence of an alcohol produces alkoxytrimethylphosphonium (2). Control experiments and density functional theory calculations suggested that the cleavage of the P=Se bond is initiated by nucleophilic attack of carboxylate on a Cd2+-activated phosphine selenide to produce an acyloxytrialkylphosphonium intermediate (1), which is converted to 2 in the presence of an alcohol.
- Garcia-Rodriguez, Raul,Liu, Haitao
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p. 1400 - 1403
(2012/03/12)
-
- Organic-inorganic hybrid porous sulfonated zinc phosphonate material: Efficient catalyst for biodiesel synthesis at room temperature
-
A new porous zinc phosphonate material (HZnP-1) has been synthesized via the reaction between p-xylenediphosphonic acid and anhydrous ZnCl2 under hydrothermal and mildly acidic conditions (pH ~ 5) in the absence of any structure directing agent. The phenyl group of this material has been sulfonated with concentrated sulfuric acid to obtain sulfonic acid functionalized material HZnPS-1. Powder X-ray diffraction (XRD), field emission scanning electron microscopy (FE SEM), N2 sorption, solid state 13C CP MAS and 31P MAS NMR, and FT IR spectroscopic tools are employed to characterize these materials. The crystal structures of both the materials are indexed corresponding to the new orthorhombic phases with unit cell parameters a = 11.00, b = 8.74, c = 14.62 A, α = β = γ = 90° for HZnP-1, and a = 10.65, b = 13.52, c = 15.30 A and α = β = γ = 90° for HZnPS-1. HZnPS-1 showed outstanding catalytic activity and high recycling efficiency for the synthesis of different biodiesel compounds via esterification of long chain fatty acids by using methanol as both reactant and solvent at room temperature. The green and eco-friendly catalytic system described herein can overcome the problem faced by the existing catalytic systems known in biodiesel synthesis, such as drastic conditions (high reaction temperature) and requirement of hazardous organic solvents.
- Pramanik, Malay,Nandi, Mahasweta,Uyama, Hiroshi,Bhaumik, Asim
-
experimental part
p. 2273 - 2281
(2012/09/08)
-
- Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)
-
A series of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters was synthesized by the cyclocondensation of respective fatty hydrazides with 4-alkoxy-1,1,1-trialomethyl-3-alquen-2-ones. Efficient and regiospecific cyclizations catalyzed by BF3·MeOH gave the desired products in good to excellent yields and at high purity.
- Beck, Paulo,Dos Santos, Juliane M.,Kuhn, Bruna L.,Moreira, Dayse N.,Flores, Alex F. C.,Martins, Marcos A. P.,D'Oca, Marcelo G. M.,Piovesan, Luciana A.
-
p. 2122 - 2127
(2013/04/10)
-
- Pore-expanded SBA-15 sulfonic acid silicas for biodiesel synthesis
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Here we present the first application of pore-expanded SBA-15 in heterogeneous catalysis. Pore expansion over the range 6-14 nm confers a striking activity enhancement towards fatty acid methyl ester (FAME) synthesis from triglycerides (TAG), and free fatty acid (FFA), attributed to improved mass transport and acid site accessibility.
- Dacquin,Lee,Pirez,Wilson
-
supporting information; experimental part
p. 212 - 214
(2012/01/13)
-
- Oxygenation of monoenoic fatty acids by CYP175A1, an orphan cytochrome P450 from thermus thermophilus HB27
-
The catalytic activity of CYP175A1 toward monooxygenation of saturated and monounsaturated fatty acids of various chain lengths (C16-C24) has been investigated to assess the enzymatic properties of this orphan thermostable cytochrome P450 enzyme. The resu
- Goyal, Sandeep,Banerjee, Shibdas,Mazumdar, Shyamalava
-
p. 7880 - 7890
(2013/01/15)
-
- Efficient synthesis of unsaturated 1-monoacyl glycerols for in meso crystallization of membrane proteins
-
A highly efficient synthesis of unsaturated 1-monoacyl glycerols was established to fulfill the pressing need for materials that form lipidic mesophases utilized in membrane protein crystallization. Georg Thieme Verlag Stuttgart.
- Fu, Yu,Weng, Yue,Hong, Wen-Xu,Zhang, Qinghai
-
experimental part
p. 809 - 812
(2011/06/21)
-
- An efficient activity ionic liquid-enzyme system for biodiesel production
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The efficient production of biodiesel in hydrophobic ionic liquids using immobilized lipase was demonstrated. The use of ionic liquids containing long alkyl chains on the cation has the important advantage of producing homogeneous systems at the start of the reaction but, when the reaction is complete, a three-phase system is created that allows selective extraction of the products using straightforward separation techniques, while the ionic liquid and the enzyme can be reused. Fifteen ionic liquids based on different alkyl chain length of the methyl imidazolium cation ([C10MIM], [C 12MIM], [C14MIM], [C16MIM] and [C 18MIM]) combined with [BF4], [PF6] or [NTf 2] anions were assayed as reaction media for two immobilized lipases (Candida antarctica lipase B and Pseudomonas fluorescens lipase AK) for biodiesel production. The highest synthetic activity was obtained in [C 16MIM] [NTf2] using Novozym 435 (immobilized Candida antarctica lipase with 245.13 U g-1 IME), its activity being more than three times higher than in a solvent-free system. Additionally, in this IL the fatty acid methyl esters production was 90.29% after 3 h, while in the solvent-free system it was 27.3%. The influence of several reaction parameters, such as temperature, methanol-to-oil molar ratio, alkyl-chain length of the alcohols, IL:substrate volume ratios, amount of enzyme, and oils feedstock were studied and optimized.
- De Diego, Teresa,Manjon, Arturo,Lozano, Pedro,Vaultier, Michel,Iborra, Jose L.
-
experimental part
p. 444 - 451
(2011/04/18)
-
- PROCESS FOR THE PREPARATION OF DICARBOXYLIC ACIDS OR DICARBOXYLIC ACID ESTERS BY METATHESIS
-
The present invention relates to a process for the preparation of dicarboxylic acids or dicarboxylic acid esters comprising the following process steps: A1 provision of at least the following reactants: a1 - a first aliphatic compound having 5 to 40 carbon atoms with in each case at least one functional group of the general formula (I) and (II), wherein R1 is a saturated or unsaturated aliphatic group having 2 to 20, preferably 4 to 16 and particularly preferably 6 to 12 carbon atoms and R2 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably having 1 to 5 carbon atoms and particularly preferably having 1, 2 or 3 carbon atoms formula (I) and (II) and a2 at least one further aliphatic compound which differs from the first aliphatic compound, chosen from the group consisting of a2a a compound of the general formula (III) in which n is chosen from 1, 2, 3, 4 and 5; a2b a compound of the general formula (IV) in which R3 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably having 1 to 5 carbon atoms and particularly preferably having 1, 2 or 3 carbon atoms and R4 and R5 independently of each other are a saturated alkylene group having 1 to 14 carbon atoms, preferably having 1 to 10 carbon atoms and very particularly preferably 1 to 5 carbon atoms; A2 provision of at least one organometallic catalyst based on ruthenium; A3 bringing into contact of the reactants and the catalyst to obtain a product mixture and the catalyst; A4 separating off of the catalyst; A5 optionally division of the product mixture into products Pi, i being a natural number, and the reactants which remain; the process being a metathesis reaction, and the dicarboxylic acid obtainable therefrom and the dicarboxylic acid ester obtainable therefrom, a process for the preparation of a polymer and the polymer obtainable by this process.
- -
-
Page/Page column 16-17
(2011/10/05)
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- Catalytic deoxygenation of oleic acid in continuous gas flow for the production of diesel-like hydrocarbons
-
Continuous gas phase deoxygenation of oleic acid in the presence of hydrogen employing a granular 2 wt% Pd/C catalyst was investigated under solvent free conditions. Conversion of oleic acid and selectivity to the desired diesel-like C17 hydrocarbons heptadecane and heptadecenes was studied at different reaction conditions such as temperature, gas flow and catalyst amount. The best hydrocarbon yield was achieved with low reaction temperatures, high catalyst amounts and high hydrogen flows. To further decrease the reaction temperature but yet maintain a pure gas phase reaction, reactions were conducted in vacuum. Furthermore, water was added in varying amounts to support desorption and to determine if catalyst deactivation could be overcome. The deoxygenation catalyst was characterized by nitrogen adsorption isotherms (BET; Brunauer-Emmet-Teller method), X-ray powder diffraction (XRD), thermogravimetric analysis (TGA) and field emission scanning electron microscopy (FESEM).
- Arend, Matthias,Nonnen, Thomas,Hoelderich, Wolfgang F.,Fischer, Jürgen,Groos, Jeremie
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experimental part
p. 198 - 204
(2012/02/02)
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- Efficient conversion of triacylglycerols and fatty acids to biodiesel in a microwave reactor using metal triflate catalysts
-
We report that catalytic quantities of the Lewis acidic metal catalysts scandium triflate and bismuth triflate promote conversion of oleic, linoleic, palmitic and myristic acids and their glyceryl triesters to the corresponding methyl esters (biodiesel) in greater than 90% yield upon microwave heating. Additionally, both catalysts could be recovered and reused in esterification reactions at least six times.
- Socha, Aaron M.,Sello, Jason K.
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experimental part
p. 4753 - 4756
(2010/11/19)
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- Preparation of fatty acid methyl esters for gas-liquid chromatography
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A convenient method using commercial aqueous concentrated HCl (conc. HCl; 35%, w/w) as an acid catalyst was developed for preparation of fatty acid methyl esters (FAMEs) from sterol esters, triacylglycerols, phospholipids, and FFAs for gas-liquid chromatography (GC). An 8% (w/v) solution of HCl in methanol/water (85:15, v/v) was prepared by diluting 9.7 ml of conc. HCl with 41.5 ml of methanol. Toluene (0.2 ml), methanol (1.5 ml), and the 8% HCl solution (0.3 ml) were added sequentially to the lipid sample. The final HCl concentration was 1.2% (w/v). This solution (2 ml) was incubated at 45°C overnight or heated at 100°C for 1-1.5 h. The amount of FFA formed in the presence of water derived from conc. HCl was estimated to be 1.4%. The yields of FAMEs were ≥96% for the above lipid classes and were the same as or better than those obtained by saponification/methylation or by acid-catalyzed methanolysis/ methylation using commercial anhydrous HCl/ methanol. The method developed here could be successfully applied to fatty acid analysis of various lipid samples, including fish oils, vegetable oils, and blood lipids by GC. Copyright
- Ichihara, Ken'Ichi,Fukubayashi, Yumeto
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experimental part
p. 635 - 640
(2010/09/10)
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