Citation: 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]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 1104-1110. doi: 10.6023/cjoc201511019 shu

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

1.
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037

Corresponding author: Zhang Xiaoxiang, s070038@hotmail.com Zhu Xinbao, zhuxinbao@njfu.com.cn
Received Date: 12 November 2015
Revised Date: 21 December 2015

Fund Project: Project supported by the 948 Project Foundation of State Forestry Administration No.2015-4-55

Figures(3)

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.
- benzothiazolium,
- ionic liquids,
- ricinoleic acid,
- esterification,
- catalytic activity
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沈阳化工大学材料科学与工程学院沈阳 110142