Page 67 - 《精细化工》2022年第5期

第 39 卷第 5 期 精 细 化 工 Vol.39, No.5
2022 年 5 月 FINE CHEMICALS May 2022

催化与分离提纯技术
凹凸棒土固载 N-杂环卡宾催化安息香缩合反应

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钱存卫 ，杨刘君 ，陈选荣 1,2*
（1. 盐城师范学院 化学与环境工程学院，江苏 盐城 224007；2. 盐城师范学院 分析测试中心，江苏 盐
城 224007）

摘要：将 5 种不同的 N-杂环卡宾（NHCs）前体固载到凹凸棒土（ATP）表面，制备了 5 种固载 NHCs 催化剂。
通过 FTIR、元素分析、BET 和 TEM 对其进行了表征。以苯甲醛的安息香缩合反应为模板，对反应条件进行了
优化，并考察了底物的普适性。最后对催化剂的重复使用性进行了评价。结果表明，NHCs 前体成功地固载到
凹凸棒土表面，制备的固载 NHCs 催化剂能有效催化安息香缩合反应，其中，1-正丁基-3-(3-三甲氧基硅丙基)
苯并咪唑氯化物（BTBCl）@ATP 性能最优。当 BTBCl@ATP 中苯并咪唑盐用量为 1%（以苯甲醛物质的量计，
下同），NaOH 用量 40%，2 mL 甲醇，在氩气中 110 ℃下反应 4 h，产物的收率可达 90%。在优化条件下，
BTBCl@ATP 可催化多种芳香醛的安息香缩合反应，收率在 61%~86%之间。BTBCl@ATP 使用 5 次后，其催化
活性没有明显下降。
关键词：凹凸棒土；固载型催化剂；氮杂环卡宾；安息香缩合反应；催化技术
中图分类号：TQ426.7；TQ244.6 文献标识码：A 文章编号：1003-5214 (2022) 05-0921-07

Attapulgite supported N-heterocyclic carbens for

benzoin condensation reactions

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QIAN Cunwei , YANG Liujun , CHEN Xuanrong 1,2*
（1. School of Chemical and Environmental Engineering, Yancheng Teachers University, Yancheng 224007, Jiangsu,
China; 2. Instumental Analysis Center, Yancheng Teachers University, Yancheng 224007, Jiangsu, China）

Abstract: Five N-heterocyclic carbens (NHCs) supported catalysts were prepared by grafting five different
NHCs precursors onto the surface of attapulgite (ATP) and characterized by FTIR, elemental analysis, BET
and TEM. Taking benzoin condensation reaction of benzaldehyde as template, the reaction conditions were
optimized, and the universality of substrate was investigated. Finally, the reusability of the catalyst was
evaluated. The results showed that the NHCs precursors were successfully supported on the surface of
attapulgite, and the prepared NHCs catalysts could effectively catalyze benzoin condensation reaction,
among which, 1-n-butyl-3-(3-trimethoxysilpropyl)benzoimidazolium chloride (BTBCl)@ATP had the best
performance. Under the conditions of the dosage of benzimidazole salt in BTBCl@ATP of 1% (based on
the amount of substance of benzaldehyde, the same below), NaOH dosage of 40%, 2 mL methanol as
solvent, reaction temperature of 110 ℃ and reaction time of 4 h in Ar atmosphere, the yield of product
could reach 90%. Under the above-mentioned optimized conditions, BTBCl@ATP could catalyze the
benzoin condensation reaction of various aromatic aldehydes with yields ranging from 61% to 86%. The
catalytic activity of BTBCl@ATP had no obvious decrease after 5 times of use.
Key words: attapulgite; supported catalysts; N-heterocyclic carbens; benzoin condensation reaction;
catalysis technology

收稿日期：2021-10-15; 定用日期：2021-12-27; DOI: 10.13550/j.jxhg.20211056
基金项目：国家自然科学基金（21801218）
作者简介：钱存卫（1975—），男，副教授，E-mail：qiancunwei@163.com。联系人：陈选荣（1987—），男，副教授，E-mail：
569591864@qq.com。