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.
Koritala
, p. 708 (1968)
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.
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.
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.
A green approach for enhancing the hydrophobicity of UiO-66(Zr) catalysts for biodiesel production at 298 K
Abou-Elyazed, Ahmed S.,El-Nahas, Ahmed M.,Sun, Yinyong,Yousif, Ahmed M.
, p. 41283 - 41295 (2020)
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).
Yatagai et al.
, p. 702 (1978)
Semiconductor Photocatalysis. Cis-Trans Photoisomerization of Simple Alkenes Induced by Trapped Holes at Surface States
Yanagida, Shozo,Mizumoto, Kunihiko,Pac, Chyongjin
, p. 647 - 654 (1986)
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.
Lipase-Catalysed Esterification of Oleic Acid and Methanol in Hexane - A Kinetic Study
Ramamurthi, Suresh,McCurdy, Alan R.
, p. 927 - 930 (1994)
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.
Characterization of markers of botanical origin and other compounds extracted from unifloral honeys
Schievano, Elisabetta,Morelato, Elisa,Facchin, Chiara,Mammi, Stefano
, p. 1747 - 1755 (2013)
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.
Evaluation of diatomaceous earth supported lipase sol-gels as a medium for enzymatic transesterification of biodiesel
Meunier,Legge
, p. 92 - 97 (2012)
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.
Stereoselective synthesis of isomers of the naturally occurring 13-hydroxy-2,4,9-tetradecatrienoic acid. Part II [1]
Huefner, Antje,Hoeller, Christa,Reznicek, Gottfried
, p. 447 - 459 (2004)
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.
Branched alkyl sulfonate anionic surfactant and preparation process thereof
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Paragraph 0041-0042; 0068-0069, (2021/02/10)
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.
Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis
Lam, Ying-Pong,Ng, Wing-Hin,Tan, Fei,Tse, Ying-Lung Steve,Wang, Xinyan,Yeung, Ying-Yeung
, p. 8083 - 8092 (2019/08/26)
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.