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112-62-9Relevant articles and documents
Biocatalyzed esterification of oleic acid using cell suspension and dried biomass of Aspergillus sp. RBD01
Aulakh, Satnam Singh,Sharma, Anirudh,Tejo Prakash,Prakash, Ranjana
, p. 127 - 130 (2017)
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.
Biodiesel production using a carbon solid acid catalyst derived from β-cyclodextrin
Fu, Xiao-Bo,Chen, Jie,Song, Xue-Li,Zhang, Yuan-Ming,Zhu, Yi,Yang, Jun,Zhang, Cheng-Wu
, p. 495 - 502 (2015)
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.
Transesterification of glycerol trioleate catalyzed by basic ionic liquids immobilized on magnetic nanoparticles: Influence of pore diffusion effect
Zhang, Yaping,Jiao, Qingze,Zhen, Bin,Wu, Qin,Li, Hansheng
, p. 327 - 333 (2013)
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.
Thermal degradation and isomerisation kinetics of triolein studied by infrared spectrometry and GC-MS combined with chemometrics
Christy, Alfred A.,Xu, Zhanfeng,Harrington, Peter de B.
, p. 22 - 31 (2009)
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.
Immobilization of Thermomyces lanuginosus lipase on ZnO nanoparticles: Mimicking the interfacial environment
Shah, Ekta,Mahapatra, Paramita,Bedekar, Ashutosh V.,Soni, Hemant P.
, p. 26291 - 26300 (2015)
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.
Transesterification catalyzed by superhydrophobic-oleophilic mesoporous polymeric solid acids: An efficient route for production of biodiesel
Noshadi, Iman,Kumar, Ranjan Kamat,Kanjilal, Baishali,Parnas, Richard,Liu, Hua,Li, Jiantao,Liu, Fujian
, p. 792 - 797 (2013)
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.
α,ω-functionalized C19 monomers
Walther, Guido,Deutsch, Jens,Martin, Andreas,Baumann, Franz-Erich,Fridag, Dirk,Franke, Robert,K?ckritz, Angela
, p. 1052 - 1054 (2011)
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.
Synthesis of aminimides derived from oleic acid: a new family of drag-reducing surfactants
Oba, Gabriel,Coleman, Bridgett E.,Hart, David J.,Zakin, Jacques,Zhang, Ying,Kawaguchi, Yasuo,Talmon, Yeshayahu
, p. 10193 - 10201 (2006)
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.
9(Z)-Octadecenamide and Fatty Amides by Bacillus megaterium (B-3437) Conversion of Oleic Acid
Kaneshiro, T.,Vesonder, R. F.,Peterson, R. E.,Weisleder, D.,Bagby, M. O.
, p. 491 - 494 (1994)
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.
Isomerizing olefin metathesis as a strategy to access defined distributions of unsaturated compounds from fatty acids
Ohlmann, Dominik M.,Tschauder, Nicole,Stockis, Jean-Pierre,Gooben, Kaethe,Dierker, Markus,Gooben, Lukas J.
, p. 13716 - 13729 (2012)
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.
