高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (1): 81-86.doi: 10.7503/cjcu20140685

• 有机化学 • 上一篇    下一篇

新型酸性离子液体催化的 Knoevenagel缩合反应

泮丽亚1, 李志峰2, 倪宇翔2, 姚振刚1, 余志平3, 吴文康3, 应安国1   

  1. 1. 台州学院医药化工学院, 台州 318000;
    2. 天津大学化工学院, 天津 300072;
    3. 浙江省低碳脂肪胺工程技术研究中心, 杭州 311604
  • 收稿日期:2014-07-24 出版日期:2015-01-10 发布日期:2014-12-23
  • 作者简介:应安国, 男, 博士, 副教授, 主要从事绿色化学化工反应研究. E-mail:agying@tzc.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:21106090)、国家级大学生创新训练项目(批准号:201410350018)和浙江省低碳脂肪胺工程技术研究中心开放基金项目(批准号:2012E10033)资助.

Knoevenagel Condensation Catalyzed by Novel Acidic Ionic Liquid

PAN Liya1, LI Zhifeng2, NI Yuxiang2, YAO Zhengang1, YU Zhiping3, WU Wenkang3, YING Anguo1   

  1. 1. School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China;
    2. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
    3. Low Carbon Fatty Amine Engineering Research Center of Zhejiang Province, Hangzhou 311604, China
  • Received:2014-07-24 Online:2015-01-10 Published:2014-12-23
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.21106090), the National Undergraduates Innovating Training Project, China(No.201410350018) and the Foundation of Low Carbon Fatty Amine Engineering Research Center of Zhejiang Province, China(No.2012E10033).

摘要:

研究了一类新型酸性离子液体催化的Knoevenagel缩合反应, 结果表明, 该催化剂适用于一系列芳香/杂环醛与α-取代活性亚甲基化合物间的反应, 反应可在室温下进行, 反应时间短且收率良好(92% ~98%). 该反应体系操作简单, 产物易分离. 提出了可能的反应机理并对机理进行了验证. 该离子液体重复使用5次后仍具有较高的反应活性.

关键词: 新型酸性离子液体, Knoevenagel缩合反应, 绿色化学, 重复使用性

Abstract:

A series of novel multiacidic ionic liquids([TEOA] [CF3COO]) based on triethanolamine were synthesized through the two-step method and introduced as catalysts for Knoevenagel condensation of complex active methylene compounds. [TEOA] [CF3COO] showed the best catalytic performance. The reactions were carried out at room temperature and the amount of catalyst was only 2%(molar fraction). The reaction system was applicable to a wide range of aromatic/heteroaromatic aldehydes with the complex α-substituted active methylene compounds affording the products in excellent yields(92%—98%) within minutes. The reaction system was operationally simple and the desired products could be easily separated from the reaction mixture. A plausible mechanism for the Knoevenagel reaction catalyzed by [TEOA] [CF3COO] was proposed and the relevant evidences were given. In addition, the ionic liquid could be regenerated and recycled five timeswithout a significant loss of activity.

Key words: Novel acidic ionic liquid, Knoevenagel condensation, Green chemistry, Recyclability

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