Synthesis of Novel Benzothiazolium Ionic Liquids and Research on Their Catalytic Esterification for Ricinoleic Acid

doi:10.6023/cjoc201511019

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1104-1110.DOI: 10.6023/cjoc201511019 Previous Articles Next Articles

NOTE

新型苯并噻唑离子液体的合成及其催化蓖麻油酸酯化研究

张海飞, 刘冬梅, 康婷婷, 王也, 张小祥, 朱新宝

南京林业大学化学工程学院南京 210037

收稿日期:2015-11-12 修回日期:2015-12-21 发布日期:2016-01-15
通讯作者: 朱新宝 E-mail:s070038@hotmail.com,zhuxinbao@njfu.com.cn
基金资助:
国家林业局948项目基金(No.2015-4-55)资助项目.

Synthesis of Novel Benzothiazolium Ionic Liquids and Research on Their Catalytic Esterification for Ricinoleic Acid

Zhang Haifei, Liu Dongmei, Kang Tingting, Wang Ye, Zhang Xiaoxiang, Zhu Xinbao

College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037

Received:2015-11-12 Revised:2015-12-21 Published:2016-01-15
Supported by:
Project supported by the 948 Project Foundation of State Forestry Administration (No. 2015-4-55).

1. Synthesis of Novel Benzothiazolium Ionic Liquids and Research on Their Catalytic Esterification for Ricinoleic Acid.PDF(1075KB)

Abstract

Four new task-specfic benzothiazolium ionic liquids (ILs) [HBth]HSO_4, [HBth]H₂PO₄, [HBth]ClO₄, [HBth]NO₃ were synthesized and characterized by NMR and FT-IR, which bear the proton acid groups based on low price benzothiazole as raw material. The catalytic activities of these acidic ionic liquids were investigated by the esterification of ricinoleic acid with ethanol ethylene glycol monobutyl ether (EGBE) and were compared with concentrated sulfuric acid. The results showed that under the optimized conditions: n(Ricinoleic acid):n(EGBE)=1:1.15, catalyst dosage 2% (wt) of ricinoleic acid, reaction temperature 90 ℃ and reaction time 5 h, esterification yield was up to 98.8%. The ionic liquids dried in vacuum till remained high activity after reused for 10 times. Finally, the yields of series of ricinoleic acid binary alcohol ether ester and short-chain fatty acids ester were also high with [HBth]HSO₄ as catalyst, and the ionic liquids can form split-phases with ester product. Compared with the traditional sulfuric acid catalytic esterification, catalytic esterification of such ionic liquid has the advantages of low production cost, clean process, low corrosion rate, reusable, and has the potential of replacing the traditional sulfuric acid in catalytic esterification reaction of ricinoleic acid.

Key words: benzothiazolium, ionic liquids, ricinoleic acid, esterification, catalytic activity

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Zhang Haifei, Liu Dongmei, Kang Tingting, Wang Ye, Zhang Xiaoxiang, Zhu Xinbao. Synthesis of Novel Benzothiazolium Ionic Liquids and Research on Their Catalytic Esterification for Ricinoleic Acid[J]. Chin. J. Org. Chem., 2016, 36(5): 1104-1110.

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新型苯并噻唑离子液体的合成及其催化蓖麻油酸酯化研究

Synthesis of Novel Benzothiazolium Ionic Liquids and Research on Their Catalytic Esterification for Ricinoleic Acid

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