利用自制简易流动合成反应仪制备2-(4-氯亚苄基)丙二腈—

引用本文: 王一诺, 干浥尘, 李珂宇, 徐大振. 利用自制简易流动合成反应仪制备2-(4-氯亚苄基)丙二腈——推荐一个化学综合实验[J]. 大学化学, 2026, 41(7): 319-325. doi: 10.12461/PKU.DXHX202506036 shu

Citation: Yinuo Wang, Yichen Gan, Keyu Li, Dazhen Xu. Synthesis of 2-(4-Chlorobenzylidene) malononitrile via a self-made continuous flow reactor: a proposed comprehensive chemistry experiment[J]. University Chemistry, 2026, 41(7): 319-325. doi: 10.12461/PKU.DXHX202506036 shu

利用自制简易流动合成反应仪制备2-(4-氯亚苄基)丙二腈——推荐一个化学综合实验

南开大学化学学院, 农药国家工程研究中心, 天津 300071

通讯作者: 徐大振,Email:xudazhen@nankai.edu.cn

基金项目:
国家级大学生创新创业训练计划(202310055078)

摘要: 连续流反应由于其操作安全、反应高效、环境友好等优点，近年来在合成领域中得到广泛应用。本实验设计了一种连续流反应，在聚苯乙烯材料上负载1,4-二氮杂双环[2.2.2]辛烷(DABCO)作为可循环催化剂，催化4-氯苯甲醛与丙二腈间的Knoevenagel缩合反应，绿色、高效合成2-(4-氯亚苄基)丙二腈。本实验将教材中经典的有机反应与科研前沿相结合，在帮助学生巩固理论的基础上，引入新型的连续流反应激发学生的学习兴趣，鼓励学生对经典有机反应制备过程进行优化，培养善于思考、勇于创新的综合型人才。

关键词:

English

Synthesis of 2-(4-Chlorobenzylidene) malononitrile via a self-made continuous flow reactor: a proposed comprehensive chemistry experiment

National Engineering Research Center of Pesticide, College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Dazhen Xu, xudazhen@nankai.edu.cn

Received Date: 10 June 2025
Revised Date: 04 August 2025
Available Online: 24 October 2025

Abstract: Continuous flow reactions have gained widespread application in synthetic chemistry in recent years owing to their operational safety, high efficiency, and environmental friendliness. This experiment presents a continuous flow system employing polystyrene-immobilized 1,4-diazabicyclo[2.2.2]octane (DABCO) as a recyclable catalyst for the Knoevenagel condensation between 4-chlorobenzaldehyde and malononitrile, enabling the green and efficient synthesis of 2-(4-chlorobenzylidene)malononitrile. By integrating fundamental organic reactions from textbooks with contemporary research methodologies, this experiment not only reinforces students’ theoretical knowledge but also introduces innovative continuous flow technology to stimulate learning interest. The approach encourages students to optimize traditional organic synthesis processes, fostering the development of critical thinking and innovation skills in future chemists.

Key words:

1. [1]
  A.V. Lapierre, R.A. Olsina, J. Raba, Anal. Chim. Acta 1999, 396, 143.A.V. Lapierre, R.A. Olsina, J. Raba, Anal. Chim. Acta 1999, 396, 143.
2. [2]
  C. Wiles, P. Watts, Green Chem. 2012, 14, 38.C. Wiles, P. Watts, Green Chem. 2012, 14, 38.
3. [3]
  F. Zhou, H. Liu, Z. Wen, B. Zhang, G. Chen, Ind. Eng. Chem. Res. 2018, 57, 11288.F. Zhou, H. Liu, Z. Wen, B. Zhang, G. Chen, Ind. Eng. Chem. Res. 2018, 57, 11288.
4. [4]
  L. Hao, B. Wang, J. Shi, B. Fu, C. Shi, X. Hao, Bioresour. Technol. 2023, 380, 129062.L. Hao, B. Wang, J. Shi, B. Fu, C. Shi, X. Hao, Bioresour. Technol. 2023, 380, 129062.
5. [5]
  D. Li, Y. Lv, H. Zeng, J. Zhang, Chem. Eng. J. 2016, 298, 107.D. Li, Y. Lv, H. Zeng, J. Zhang, Chem. Eng. J. 2016, 298, 107.
6. [6]
  G. Laudadio, N.J.W. Straathof, M.D. Lanting, B. Knoops, V. Hessel, T. Noël, Green Chem. 2017, 19, 4061.G. Laudadio, N.J.W. Straathof, M.D. Lanting, B. Knoops, V. Hessel, T. Noël, Green Chem. 2017, 19, 4061.
7. [7]
  A. Yang, J. Yue, S. Zheng, X. Yang, L. Kong, D. Zhou, L. Qin, H. Zhong, Res. Chem. Intermed. 2022, 48, 4373.A. Yang, J. Yue, S. Zheng, X. Yang, L. Kong, D. Zhou, L. Qin, H. Zhong, Res. Chem. Intermed. 2022, 48, 4373.
8. [8]
  W.-Q. Yuan, S.-Q. Zhou, Y.-Y. Jiang, H.-H. Li, H.-D. Zheng, J. Flow Chem. 2020, 10, 227.W.-Q. Yuan, S.-Q. Zhou, Y.-Y. Jiang, H.-H. Li, H.-D. Zheng, J. Flow Chem. 2020, 10, 227.
9. [9]
  S. Michałek, A. Powała, L. Gurba-Bryśkiewicz, N. Piórkowska, P. Olejkowska, A. Yamani, Z. Ochal, K. Dubiel, M. Wieczorek, Monatsh. Chem. 2023, 154, 1307.S. Michałek, A. Powała, L. Gurba-Bryśkiewicz, N. Piórkowska, P. Olejkowska, A. Yamani, Z. Ochal, K. Dubiel, M. Wieczorek, Monatsh. Chem. 2023, 154, 1307.
10. [10]
  Á. Tajti, N. Tóth, E. Bálint, G. Keglevich, J. Flow Chem. 2018, 8, 11.Á. Tajti, N. Tóth, E. Bálint, G. Keglevich, J. Flow Chem. 2018, 8, 11.
11. [11]
  F.-J. Wang, Y.-C. Ding, J.-H. Xu, Ind. Eng. Chem. Res. 2019, 58, 16338.F.-J. Wang, Y.-C. Ding, J.-H. Xu, Ind. Eng. Chem. Res. 2019, 58, 16338.
12. [12]
  N. Zaquen, M. Rubens, N. Corrigan, J. Xu, P.B. Zetterlund, C. Boyer, T. Junkers, Prog. Polym. Sci. 2020, 107, 101256.N. Zaquen, M. Rubens, N. Corrigan, J. Xu, P.B. Zetterlund, C. Boyer, T. Junkers, Prog. Polym. Sci. 2020, 107, 101256.
13. [13]
  D.-Z. Xu, S. Shi, Y. Wang, RSC Adv. 2013, 3, 23075.D.-Z. Xu, S. Shi, Y. Wang, RSC Adv. 2013, 3, 23075.
14. [14]
  Mechanism of the Knoevenagel Condensation. [2025-10-23]. https://www.organic-chemistry.org/namedreactions/knoevenagel-condensation.shtmMechanism of the Knoevenagel Condensation. [2025-10-23]. https://www.organic-chemistry.org/namedreactions/knoevenagel-condensation.shtm
15. [15]
  落实“双碳”行动建设美丽中国. [2025-10-23]. https://www.gov.cn/yaowen/liebiao/202404/content_6948005.htm

扫一扫看文章

计量

PDF下载量: 0
文章访问数: 8
HTML全文浏览量: 2

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

利用自制简易流动合成反应仪制备2-(4-氯亚苄基)丙二腈——推荐一个化学综合实验

通讯作者: 徐大振,Email:xudazhen@nankai.edu.cn

English

Synthesis of 2-(4-Chlorobenzylidene) malononitrile via a self-made continuous flow reactor: a proposed comprehensive chemistry experiment

Corresponding author: Dazhen Xu, xudazhen@nankai.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

利用自制简易流动合成反应仪制备2-(4-氯亚苄基)丙二腈——推荐一个化学综合实验

通讯作者: 徐大振,Email:xudazhen@nankai.edu.cn

English

Synthesis of 2-(4-Chlorobenzylidene) malononitrile via a self-made continuous flow reactor: a proposed comprehensive chemistry experiment

Corresponding author: Dazhen Xu, xudazhen@nankai.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs