20290-84-0Relevant academic research and scientific papers
Production of Valuable Esters from Oleic Acid with a Porous Polymeric Acid Catalyst without Water Removal
Kim, Yo-Han,Han, Jusung,Jung, Byeong Yeon,Baek, Heeyoel,Yamada, Yoichi M. A.,Uozumi, Yasuhiro,Lee, Yoon-Sik
, p. 29 - 32 (2016)
We demonstrate the use of porous phenolsulfonic acid-formaldehyde (PSF) resins as solid-acid catalysts, which showed excellent performance in the esterification of fatty acids without using any solvent or introducing a water-removal process. The catalyst was reused up to 30 times without significant loss of activity.
Chemically Modified Lipase from Thermomyces lanuginosus with Enhanced Esterification and Transesterification Activities
Noro, Jennifer,Cavaco-Paulo, Artur,Silva, Carla
, p. 4524 - 4531 (2021/09/02)
Lipase from Thermomyces lanuginosus is one of the most explored enzymes for the esterification of several added-value industrial compounds, such as biodiesel, fragrances, and flavors. Its selectivity in these reactions is mostly related with its activity towards small alcohols. In this work, the impact of the chemical modification, with 4 dodecyl chains at its surface, was evaluated regarding its transesterification and esterification activities, comparing with the native form. Linear size-differentiated alcohols (from 1 to 20 carbons in the aliphatic chain) were used to explore for the first time the effect of the chain length in both transesterification and esterification reactions, using p-nitrophenyl palmitate and oleic acid as model compounds, respectively. The chemically modified lipase showed an outstanding improvement of its catalytic performance than the native enzyme, being this increase directly proportional to the size of the alcohols chain used as substrates. The enormous potential and remarkable versatility of this novel super catalyst was here demonstrated, where diverse types of esters, differing in their potential applications (biodiesel, cosmetics, fine chemistry), were efficiently synthesized. The produced esters were fully characterized by 1H NMR, GC-MS, and FTIR.
Catalytic Biodiesel Production Mediated by Amino Acid-Based Protic Salts
Li, Jingbo,Guo, Zheng
, p. 1792 - 1802 (2017/04/27)
Hetero- and homogeneous acid catalysts are effective catalysts for the production of biodiesel from oils containing high free fatty acids. The protic salts synthesized from natural amino acids were examined for catalytic activity and efficiency for the esterification of oleic acid after structural identification and characterization. In the esterification reaction of oleic acid with methanol, [Asp][NO3] was the best catalyst, and its high activity correlated to its high Hammett acidity. The optimal reaction conditions for the esterification of oleic acid to achieve 97 % biodiesel yield were: 70 °C, 10 % catalyst loading (w/w, on oleic acid basis), methanol/oleic acid ratio 7.5:1, and 5 h. Generally, [Asp][NO3] could be a good catalyst for the esterification of oleic acid with alcohols with chain lengths of up to six. The biodiesel yield of 93.86 % obtained from palm fatty acid distillate implies that the catalyst has potential for industrial application. A study of the kinetics indicated that the reaction followed pseudo-first-order kinetics with an activation energy and pre-exponential of 57.36 kJ mol?1 and 44.24×105 min?1, respectively. The aspartic acid-derived protic salt is a promising, operationally simply, sustainable, renewable, and possibly biodegradable catalyst for the conversion of free fatty acids into biodiesel.
Guanidine based task specific ionic liquids for the synthesis of biolubricant range esters under solvent-free condition
Porwal, Jyoti,Kumar, Subodh,Kaul, Savita,Jain, Suman L.
, p. 93640 - 93644 (2016/10/18)
Guanidine-based task specific ionic liquids (ILs) were synthesized from the reaction of 1,1,3,3-tetramethyl guanidine with protic acids and used for the synthesis of higher alcohol esters of fatty acids as biolubes under solvent free condition. The synthesized 1,1,3,3-tetramethylguanidinium hydrogen sulphate (TMG·HSO4) was found to be most effective among the different ILs including 1,1,3,3-tetramethylguanidinium acetate (TMG·Ac), 1,1,3,3-tetramethylguanidinium hydrogen phosphate (TMG·H2PO4) and 1,1,3,3-tetramethylguanidinium trifluoro acetate (TMG·TFA). The effect of various reaction parameters such as reaction temperature, reaction time, catalyst amount etc. has been studied. After completion the reaction the esterification product was isolated and the recovered IL was reused for several runs without loss in catalytic activity.
2,2,6,6-Tetramethylpiperidinium triflate (TMPT): a highly selective and self-separated catalyst for esterification
Gao, Lan,Liu, Taoping,Tao, Xiaochun,Huang, Yongmin
supporting information, p. 4905 - 4909 (2016/10/24)
An eco-friendly and readily accessible 2,2,6,6-tetramethylpiperidinium triflate was found as highly-selective and self-separated catalyst for esterification under solvent-free condition. The X-ray crystallography revealed that it formed a ‘hydrophobic wall’ which could effectively eliminate the generated water from the reactive sites. Moreover, it could precipitate from the reaction system with excellent recovery ratio (>99%) and be reused for ten times without any significant loss of activity.
SO3H and NH2+ functional carbon-based solid acid catalyzed transesterification and biodiesel production
Cai, Liangzhen,Meng, Decai,Zhan, Shaoqi,Yang, Xiaoxia,Liu, Taoping,Pu, Huiming,Tao, Xiaochun
, p. 72146 - 72149 (2015/09/08)
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.
The carbon material functionalized with NH2+ and SO3H groups catalyzed esterification with high activity and selectivity
Zhan, Shaoqi,Tao, Xiaochun,Cai, Liangzhen,Liu, Xiaohui,Liu, Taoping
supporting information, p. 4649 - 4653 (2015/02/19)
A novel carbon-based solid acid was conveniently prepared by heating a mixture of d-glucose, p-toluenesulfonic acid and diphenylammonium tosylate. Its structure was measured by XRD, FT-IR, XPS, 13C MAS NMR and EA to illustrate that the carbon material has been functionalized with NH2+ and SO3H groups and has a strong "hydrophobic effect". It can be used to catalyze the esterification reaction of carboxylic acids with equimolar amounts of sterically demanding and acid-sensitive alcohols with high reactivity (yield up to 90%) and selectivity (up to 95%) in heptane at 80 °C. It could be easily recovered and reused more than ten times without loss of activity.
Esterification of oleic acid in [Bmim]BF4/[Hmim]HSO4 + TX-100/cyclohexane ionic liquid microemulsion
Jiang, Dongyu,Chen, Li,Wang, Aili,Yan, Zongcheng
, p. 54427 - 54433 (2015/02/19)
Esterification of oleic acid was carried out in a 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF4)/Triton X-100 + 1-hexyl-3-methylimidazolium hydrogen sulfate ([Hmim]HSO4)/cyclohexane microemulsion. A pseudo ternary phase diagram of the designed systems was drawn to investigate the phase behavior of the microemulsion, with the surfactant [Hmim]HSO4 acting as a catalyst. The effects of various reaction parameters were explored. The results showed that the maximum yield of lauryl oleate reaches 91.17% and its selectivity reaches 98.55% under optimum reaction conditions. The reaction was carried out with 8 wt% catalyst at 373 K for 6 h. The molar ratios of [Bmim]BF4 to the surfactant and of oleic acid to lauryl alcohol were 0.24 and 0.2, respectively. Comparison reactions between different alcohols and oleic acid were also performed, and the results showed that long alkyl chain alcohols promote the reaction rate. UV-vis absorption spectra demonstrated that the generated water enters the [Bmim]BF4 microdomain of the ionic liquid microemulsions. A possible mechanism of the reaction was also presented. All the results indicate that the [Bmim]BF4/TX-100 + [Hmim]HSO4/cyclohexane microemulsion is a very efficient catalyst system for esterification reactions. This journal is
TRIESTER-BASED LUBRICANTS AND METHODS OF MAKING SAME
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, (2008/12/08)
The present invention is generally directed to triester-based lubricant compositions. The present invention is also directed to methods of making these and other similar lubricant compositions. In some embodiments, the methods for making such triester-based lubricants utilize a biomass precursor and/or low value Fischer-Tropsch (FT) products (e.g., alcohols) so as to produce high value triester-based lubricants. In some embodiments, such triester-based lubricants are derived, at least in part, from FT alcohols and fatty acids. The fatty acids can be from a bio-based source (i.e., biomass, renewable source) or can be derived from FT alcohols via oxidation.
Melting points and viscosities of fatty acid esters that are potential targets for engineered oilseed
Yao, Linxing,Hammond, Earl,Wang, Tong
, p. 77 - 82 (2008/09/19)
Our previous isolation of branched-chain fatty acid (BCFA) methyl esters from lanolin was improved and scaled up. Also, oleate esters of isopropanol, oleyl alcohol and normal alcohols of 1-12 carbons chain lengths were prepared. Esters were made by interesterification with sodium alcoholates and by esterification with Candida antarctica lipase. It proved easier to obtain pure esters by the enzymatic synthesis. Melting points and viscosities over the range of 0-70 °C were determined in order to better identify potential lubricant targets that might be produced by genetically modified oilseed crops. Isopropyl and butyl oleate have melting points of -33 and -32 °C, respectively and viscosities that range from ~17 cp (0 °C) to ~2.5 cp (70 °C). They should have suitable stability for lubricants. BCFA esters had viscosities similar to their straight chain analogs. Viscosities increased with alcohol chain length and decreased with temperature. The dependence of viscosity on temperature was fit with an equation based on Erying's rate equation. Some esters with branched acid or branched alcohol moieties, and some oleate esters might be utilized as biolubricants or biofuels on the basis of their melting points and viscosities.
