Chinese Journal of Organic Chemistry >
Synthesis and Catalytic Esterification Performance of Caprolactam Task-Specific Ionic Liquids
Received date: 2015-03-10
Revised date: 2015-04-21
Online published: 2015-04-27
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 20576026, 21106032).
Four kinds of caprolactam task-specific ionic liquids (TSILs), 1-(3-sulfopropyl)caprolactam hydrogen sulfate, 1-(3-sulfopropyl)caprolactam p-toluene sulfonate, 1-(3-sulfopropyl)caprolactam phosphate sulfonate, 1-(3-sulfopropyl)ca-prolactam tetrafluoroborate, were prepared and characterized with low price caprolactam as raw material. The catalytic activities of these acidic ionic liquids were investigated by the esterification of acetic acid with ethanol and were compared with 3 kinds of SO3H-functionalized ionic liquids with different nitrogen heterocycles and concentrated sulfuric acid. The results showed that under the optimized conditions [n(C2H5OH):n(CH3COOH)=1:1.5], catalyst amount of 5% (w) based on acetic acid and ethanol., reaction temperature 80 ℃ and reaction time 6 h), the yield of ethyl acetate was up to 93.8%. The ionic liquids dried in vacuum till remained high activity after reused for 10 times, and the corrosion rates of the 316L austenitic stainless steel plates immersed in the systems with these ionic liquids were less than one sixth of that with sulfuric acid. Finally, the yields of series of ethyl esters were also high with [C3SO3HCP]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, long useage cycle, and has the potential of replacing the traditional sulfuric acid in catalytic esterification reaction.
Hu Jingjing , Zhao Dishun , Li Jingjing , Zhai Jianhua , Hu Tiantian . Synthesis and Catalytic Esterification Performance of Caprolactam Task-Specific Ionic Liquids[J]. Chinese Journal of Organic Chemistry, 2015 , 35(8) : 1773 -1780 . DOI: 10.6023/cjoc201503012
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