A study of the esterification of caffeic acid with methanol using p-toluenesulfonic acid as a catalyst

文献类型： 外文期刊

第一作者： Wang, Jun

作者： Wang, Jun;Gu, Shuangshuang;Pang, Na;Wang, Fangqin;Wu, Fuan;Wu, Fuan

作者机构：

关键词： caffeic acid;catalysis;esterification;kinetics;methyl caffeate;p-toluenesulfonic acid

期刊名称：JOURNAL OF THE SERBIAN CHEMICAL SOCIETY （ 影响因子：1.24； 五年影响因子：1.144 ）

ISSN： 0352-5139

年卷期： 2013 年 78 卷 7 期

页码：

收录情况： SCI

摘要： Caffeic acid (CA) could be considered as an important natural antioxidant. However, the low solubility and stability of CA in various solvent systems is a major limiting factor governing its overall application in the lipid industry. However, the synthesis of methyl caffeate (MC) using CA and methanol is a feasible way to improve its lipophilicity. Herein, the reaction conditions and kinetic parameters for the synthesis of MC using p-toluenesulfonic acid (PTSA) as a catalyst were investigated, and the product was confirmed by liquid chromatography-mass spectrometry (LC-MS), Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy, and melting point analysis. The highest yield of MC catalyzed by PTSA attained 84.0 % under the optimum conditions as follows: molar ratio of methanol to CA of 20:1, reaction temperature of 65 degrees C, mass ratio of catalyst to substrate of 8 %, and a reaction time of 4 h. The esterification kinetics of CA and methanol is described by the pseudo-homogeneous second order reversible model. The relationship between temperature and the forward rate constant gives the activation energy of 17.5 kJ mol(-1). These results indicated that PTSA possesses high catalytic activity in the synthesis of MC, which is an efficient catalyst suitable for MC production in the chemical industry.

分类号：

  • 相关文献

[1]Microfluidic biocatalysis enhances the esterification of caffeic acid and methanol under continuous-flow conditions. Wang, Sha-Sha,Li, Zhong-Jian,Sheng, Sheng,Wu, Fu-An,Wang, Jun,Sheng, Sheng,Wu, Fu-An,Wang, Jun.

[2]Potassium release rates from ustisols and their application. Lu, XN,Zhang, MH,Xu, JM.

[3]Generic DART-MS platform for monitoring the on-demand continuous-flow production of pharmaceuticals: Advancing the quantitative protocol for caffeates in microfluidic biocatalysis. Xu, Yan,Zhang, Dong-Yang,Liu, Xi,Sheng, Sheng,Wu, Guo-Hua,Wang, Jun,Wu, Fu-An,Xu, Yan,Zhang, Dong-Yang,Sheng, Sheng,Wu, Guo-Hua,Wang, Jun,Wu, Fu-An,Meng, Xiang-Yun.

[4]Ultrasound irradiation accelerates the lipase-catalyzed synthesis of methyl caffeate in an ionic liquid. Wang, Jun,Wang, Shasha,Li, Zhongjian,Gu, Shuangshuang,Wu, Fuan,Wang, Jun,Wang, Shasha,Li, Zhongjian,Gu, Shuangshuang,Wu, Fuan,Wang, Jun,Wu, Xiangyang.

[5]Green synthesis of gold nanoparticles using Citrus maxima peel extract and their catalytic/antibacterial activities. Yuan, Chun-Gang,Huo, Can,Gui, Bing,Cao, Wei-Ping. 2017

[6]Aptamer based photometric assay for the antibiotic sulfadimethoxine based on the inhibition and reactivation of the peroxidase-like activity of gold nanoparticles. Yan, Jiao,Huang, Yafei,Zhang, Chenghui,Fang, Zongzhuang,Yan, Jiao,Huang, Yafei,Bai, Wenhui,Yan, Mengmeng,Zhu, Chao,Chen, Ailiang,Yan, Jiao,Huang, Yafei,Bai, Wenhui,Yan, Mengmeng,Zhu, Chao,Chen, Ailiang.

[7]Influence factors for the oxidation of pyrite by oxygen and birnessite in aqueous systems. Qiu, Guohong,Luo, Yao,Chen, Cheng,Lv, Qiang,Tan, Wenfeng,Liu, Fan,Liu, Chengshuai.

[8]Simultaneous Quantitation of Caffeic Acid and Ferulic Acid Based on Graphite-like C3N4/chitosan Modified Film. Jing, Lijun,Lin, Jun,Fei, Qiqi,Yang, Xiaodi,Jing, Lijun,Lin, Jun,Fei, Qiqi,Yang, Xiaodi,Sun, Chong,Tang, Haowei. 2017

[9]Functional expression of an Arabidopsis p450 enzyme, p-coumarate-3-hydroxylase, in the cyanobacterium Synechocystis PCC 6803 for the biosynthesis of caffeic acid. Xue, Yong,Grace, Stephen,He, Qingfang,Zhang, Yan,He, Qingfang.

[10]Quantum dots-based label-free fluorescence sensor for sensitive and non-enzymatic detection of caffeic acid. Xiang, Xia,Huang, Fenghong,Zheng, Mingming,Deng, Qianchun,Shi, Jianbin.

[11]Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors. Xie, Yuanchao,Shi, Fangyuan,Liu, Tianqi,Xu, Wenfang,Huang, Bing,Yu, Kexiang.

[12]Further discovery of caffeic acid derivatives as novel influenza neuraminidase inhibitors. Xie, Yuanchao,Xu, Wenfang,Huang, Bing,Yu, Kexiang.

[13]Cs-substituted H3PW12O40 on Palygorskite Clay for Esterification of Oleic Acid with Ethanol. Zhang, L. X.,Jin, Q. Z.,Shan, L.,Liu, Y. F.,Huang, J. H.,Wang, X. G.,Zhang, L. X.. 2012

[14]Esterification of guaiacol with octanoic acid over functionalized mesoporous silica. Xu, Xiwei,Jiang, Enchen,Lei, Zhiwei. 2018

[15]Ultrasonic pretreatment for lipase-catalyed synthesis of phytosterol esters with different acyl donors. Zheng, Ming-Ming,Wang, Lian,Huang, Feng-Hong,Dong, Ling,Guo, Ping-Mei,Deng, Qian-Chun,Li, Wen-Lin,Zheng, Chang.

[16]Lipase Immobilization on Hyper-Cross-Linked Polymer-Coated Silica for Biocatalytic Synthesis of Phytosterol Esters with Controllable Fatty Acid Composition. Zheng, Ming-Ming,Huang, Feng-Hong,Wang, Lian,Guo, Ping-Mei,Deng, Qian-Chun,Zheng, Ming-Ming,Huang, Feng-Hong,Wang, Lian,Guo, Ping-Mei,Deng, Qian-Chun,Lu, Yong,Feng, Yu-Qi.

[17]Immobilization of Candida rugosa lipase on hydrophobic/strong cation-exchange functional silica particles for biocatalytic synthesis of phytosterol esters. Zheng, Ming-Ming,Dong, Ling,Guo, Ping-Mei,Deng, Qian-Chun,Li, Wen-Lin,Huang, Feng-Hong,Lu, Yong,Feng, Yu-Qi.

[18]Ultrasonic pretreatment for lipase-catalyzed synthesis of 4-methoxy cinnamoyl glycerol. Guo, Pingmei,Zheng, Chang,Huang, Fenghong,Zheng, Mingming,Deng, Qianchun,Li, Wenlin.

[19]The Synthesis of Methyl Oleate Catalyzed by Phosphotungstic Acid Immobilized on the Functionalized Palygorskite. Zhang, L. X.,Jin, Q. Z.,Huang, J. H.,Liu, Y. F.,Shan, L.,Wang, X. G.,Zhang, L. X.. 2012

[20]Preparation and Characterization of a Solid Acid Catalyst from Macro Fungi Residue for Methyl Palmitate Production. Wang, Min,Wu, Wei-Wei,Wang, Sha-Sha,Shi, Xin-Yi,Wu, Fu-An,Wang, Jun,Wu, Fu-An,Wang, Jun. 2015

作者其他论文 更多>>

微信小程序