111-59-1Relevant articles and documents
Clean and Green Procedure for the Synthesis of Biodiesel from the Esterification of Free Fatty Acids and Alcohol Catalyzed by 6-O-(sulfobutyl)-Β-cyclodextrin
Zhang, Guangqing,He, Leqin,Yuan, Mingxia,Li, Hui,Chang, Tao,Qin, Shenjun
, p. 1123 - 1128 (2018)
The catalyst of 6-O-(sulfobutyl)-β-cyclodextrin (SB-CD) is renewable, non-toxic, environmentally benign and biocompatible, which could be used as efficient and recyclable catalyst for the synthesis of biodiesel from free long-chain fatty acids with low-chain alcohols as substrates. The reaction was accomplished at 60°C for 1.5 h, while the products were separated from the catalyst system by liquid/liquid at room temperature with good conversion of 91–98%. The catalyst can be reused for 10 times. The novel and clean procedure offers advantages including short reaction time, good conversion, operational simplicity, and environmentally benign characteristics.
Immobilization of a thiol-functionalized ionic liquid onto HKUST-1 through thiol compounds as the chemical bridge
Chen, Chong,Wu, Zuowang,Que, Yigen,Li, Bingxue,Guo, Qirui,Li, Zhong,Wang, Lei,Wan, Hui,Guan, Guofeng
, p. 54119 - 54128 (2016)
A novel heterogeneous catalyst [HVIm-(CH2)3SO3H]HSO4@HKUST-1 (IL@HKUST-1), with both Lewis and Br?nsted acid sites, was developed for the esterification of oleic acid with short-chain alcohols. HKUST-1 was chemically modified with ethanedithiol, and the vinyl-containing ionic liquid was then grafted onto the carrier through thiol groups. The catalyst IL@HKUST-1 was characterized by XRD, N2 adsorption-desorption, FT-IR, SEM, TG, elemental analysis, and ICP. The results proved that HKUST-1 had typical microporous structure, and the thiol groups were incorporated into the channels of the carrier. Through the reaction of vinyl and thiol, the ionic liquid was successfully immobilized onto SH-HKUST-1 by chemical covalent bonds. The catalyst was applied in the esterification of oleic acid with ethanol, and the optimal conditions were determined as follows: molar ratio of ethanol to oleic acid 12 : 1, catalyst amount 15 wt% (based on oleic acid), reaction time 4 h, and reaction temperature 90 °C. Under the conditions, the conversion of oleic acid was 92.1%. After 5 times of recycling, there was no significant decrease in conversion, showing a certain stability and good reusability of the catalyst. The catalyst also exhibited high catalytic activity in esterification of oleic acid with other short-chain alcohols.
Synthesis and analysis of the C1-C18 alkyl oleates
Vieville, Corinne,Mouloungui, Zephirin,Gaset, Antoine
, p. 101 - 108 (1995)
The C1-C18 alkyl oleates were prepared in n-hexane by esterification of oleic acid with either the primary and secondary C1-C6 alcohols or the primary fatty C8-C18 alcohols. The esterification was acid-catalyzed in the presence of p-toluene sulfonic acid (p-TSA) in a pseudo-homogeneous phase, or in the presence of the sulfonic macroporous resin (K2411) in the heterogeneous phase. The purified alkyl oleates were characterized by 13C-NMR. The oleic acid/alkyl oleate mixtures were analyzed by high-performance liquid chromatography (HPLC).
An efficient activity ionic liquid-enzyme system for biodiesel production
De Diego, Teresa,Manjon, Arturo,Lozano, Pedro,Vaultier, Michel,Iborra, Jose L.
, p. 444 - 451 (2011)
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.
Biodiesel synthesis from the esterification of free fatty acids and alcohol catalyzed by long-chain Bronsted acid ionic liquid
He, Leqin,Qin, Shenjun,Chang, Tao,Sun, Yuzhuang,Gao, Xiaorui
, p. 1102 - 1107 (2013)
A long-chain Bronsted acid ionic liquid (IL), 3-(N,N- dimethyldodecylammonium)propanesulfonic acid p-toluenesulfonate ([DDPA][Tos]), was prepared and characterized by FT-IR, 1H NMR, 13C NMR, UV/vis and TGA. The H0 (Hammett function) value of the IL was also determined. The IL as catalyst was applied to the catalytic synthesis of biodiesel from free fatty acids (FFAs). The influencing factors, such as the type and amount of catalyst, reaction time, molar ratio of fatty acid to methanol and reaction temperature, were investigated. The results indicated that the long-chain Bronsted acid IL showed high catalytic activity and fair reusability. Esterification was accomplished under the following optimized conditions: molar ratio of alcohols to FFA at 1.5:1, mole fraction of ionic liquid at 10%, 60 °C, and 3 h. The products could be separated from the catalyst system by liquid-liquid biphase separation at room temperature with good yields of 92.5% to 96.5%. The catalyst could be reused nine times after the removal of water and alcohol. Therefore, the long-chain Bronsted acid IL has good potential for the synthesis of biodiesel from low-cost feedstocks such as waste oil and woody plant oils.
Catalytic Biodiesel Production Mediated by Amino Acid-Based Protic Salts
Li, Jingbo,Guo, Zheng
, p. 1792 - 1802 (2017)
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.
Solvent-free esterification catalyzed by surfactant-combined catalysts at room temperature
Gang, Li,Xinzong, Li,Eli, Wumanjiang
, p. 348 - 351 (2007)
Solvent-free esterifications of various carboxylic acids and alcohols can be catalyzed by surfactant-combined catalysts dodecylbenzene sulfonic acid (DBSA) and copper dodecylbenzene sulfonate (CDBS) in moderate to excellent yield at room temperature. The esterification method has two notable advantages: first, there is no need for any solvent, even water, and secondly, no need for energy, the reaction can proceed smoothly at room temperature. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Synthesis and characterization of oleic succinic anhydrides: Structure-property relations
Candy, Laure,Vaca-Garcia, Carlos,Borredon, Elisabeth
, p. 271 - 277 (2005)
Alkenyl succinic anhydrides (ASA) were prepared by an -ene reaction of n-alkyl (C1 to C5) oleates with maleic anhydride. The purified compounds were characterized by FTIR, 1H NMR, and MS analytical methods to elucidate their structures. Their physicochemical properties were systematically studied and found to depend on the length of the alkyl radical. Structure-property relations were established for viscosity, m.p., and density. The combination of a long hydrophobic chain and a highly polar group with density values close to that of water implied good emulsification properties for some of these molecules. Comparison of the thermal properties of alkyl oleates and their respective ASA demonstrated that the grafting of maleic anhydride allowed the synthesis of compounds with very low melting temperatures (less than -60°C) and good stability at high temperatures (greater than 350°C) under both air and helium atmospheres. All these properties suggest a strong potential for application in the biolubricant or surfactant fields. The combined influences of the succinic part and variable ester moieties imply that each ASA molecule has its own characteristics, based on which applications could be developed. Copyright
Novel porous and hydrophobic POSS-ionic liquid polymeric hybrid as highly efficient solid acid catalyst for synthesis of oleate
Lu, Dan,Zhao, Jiwei,Leng, Yan,Jiang, Pingping,Zhang, Chenjun
, p. 27 - 30 (2016)
A novel porous and hydrophobic Br?nsted acidic solid catalyst (POSS-[VMPS][H2SO4]) was successfully synthesized by copolymerization of polyhedral oligomeric vinylsilsesquioxanes (POSSs) and sulfonic acid-functionalized imidazole ionic liquids. Catalytic tests for the esterification of oleic acid with methanol have shown that this newly obtained polymeric hybrid exhibits very high catalytic activity and selectivity, which was more active or comparable to those of the common solid acid Amberlite-732 and liquid acid H2SO4. Moreover, the catalyst has a good recyclability without significant loss in the activity.
Enzymatic Esterification of Oleic Acid with Aliphatic Alcohols for the Biodiesel Production by Candida antarctica Lipase
Rosset, Isac G.,Cavalheiro, Maria Cecilia H. T.,Assaf, Elisabete M.,Porto, Andre L. M.
, p. 863 - 872 (2013)
Biodiesel can be obtained by esterification reactions of free fatty acids with enzymatic catalysts (lipases). In this study, the immobilized Candida antarctica lipase was employed in enzymatic esterifications of oleic acid with aliphatic alcohols (methanol, ethanol, n-propanol, n-butanol). Some features that influence the enzymatic esterification reaction, such as amount of biocatalysts, reaction time, hydration level and biocatalyst turnover were evaluated. The products were determined by GC-FID and 1H NMR analyses and these analytical methods were compared. The enzymatic catalyst (C. antarctica lipase) was efficient providing high yields of biodiesel (above 90 %) in less than 24 h to ethanol, n-propanol and n-butanol, whereas for methanol, the enzyme was inactive after ten cycles of reaction. Two new quantitative easy methods were also developed to quantify esters produced by 1H NMR based on the α-CH2 protons of oleic acid and esters. The quantification method used in the enzymatic reactions by 1H NMR showed effective with small differences in comparison with GC-FID analyses. Graphical Abstract: C. antarctica lipase was employed in enzymatic esterifications of oleic acid with aliphatic alcohols (methanol, ethanol, n-propanol, n-butanol) for the biodiesel production. A new method was developed to quantify esters produced (biodiesel) by 1H NMR based on the α-CH2 protons. [Figure not available: see fulltext.]
