酸性离子液体催化合成N-氰乙基-N-羟乙基苯胺

doi:10.11944/j.issn.1000-0518.2020.05.190287

摘要/Abstract

摘要：

N-氰乙基-N-羟乙基苯胺是一种具有广泛用途的染料中间体,针对传统合成方法中的缺陷,以1-丁基-3-甲基咪唑硫酸氢盐([BMIM]HSO₄)为催化剂,丙烯腈和N-羟乙基苯胺为原料,建立了N-氰乙基-N-羟乙基苯胺的绿色合成新工艺。系统考察了离子液体种类、离子液体用量、底物比例等因素的影响规律,结果表明,[BMIM]HSO₄用量为0.8 mmol,n(N-羟乙基苯胺):n(丙烯腈)=1:1.2,反应温度为90 ℃,反应时间为12 h 时,N-氰乙基-N-羟乙基苯胺产率最高(89%),离子液体循环使用5次后,催化活性基本保持不变。

关键词: 酸性离子液体, N-氰乙基-N-羟乙基苯胺, 丙烯腈, N-羟乙基苯胺

Abstract:

N-Cyanoethyl-N-hydroxyethylaniline is an important dye intermediate with a wide range of applications. A green and efficient protocol for the synthesis of N-cyanoethyl-N-hydroxyethylaniline by reaction of acrylonitrile and N-hydroxyethyl aniline with 1-butyl-3-methylimidazolium hydrosulphates ionic liquid ([Bmim]HSO₄) as the catalyst has been developed, eliminating the inert-gas welding and complex operation of traditional methods. The effect of ionic liquid, the amount of ionic liquid, the ratio of substrates, temperature and time were investigated. The optimum reaction conditions were obtained as follow:[BMIM]HSO₄ 0.8 mmol, n(N-hydroxyethyl aniline):n(acrylonitrile)=1:1.2, reaction time of 12 h, reaction temperature of 90 ℃. The acdic ionic liquid could be easily separated and reused for at least 5 times without significantly decrease in catalytic activity.

Key words: acdic ionic liquid, N-cyanoethyl-N-hydroxyethylaniline, acrylonitrile, N-hydroxyethyl aniline

郭辉, 殷园园, 张学颖, 庄玉伟, 曹健, 张国宝. 酸性离子液体催化合成N-氰乙基-N-羟乙基苯胺[J]. 应用化学, 2020, 37(5): 512-517.

GUO Hui, YIN Yuanyuan, ZHANG Xueying, ZHUANG Yuwei, JIAN Cao, ZHANG Guobao. Synthesis of N-Cyanoethyl-N-hydroxyethylaniline Catalyzed by Acdic Ionic Liquid[J]. Chinese Journal of Applied Chemistry, 2020, 37(5): 512-517.

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