基于流动化学的硝化反应精准调控——推荐一个综合化学实验

doi:10.12461/PKU.DXHX202605016

大学化学

基于流动化学的硝化反应精准调控——推荐一个综合化学实验

李峙德, 刘一弘, 马竹清, 马道璠, 王光伟, 赵温涛, 任相伟

天津大学理学院化学系, 天津 300354

收稿日期:2026-05-11 录用日期:2026-07-22
通讯作者: 任相伟 E-mail:xiangwei_ren@tju.edu.cn Xiangwei Ren
基金资助:
国家自然科学基金项目(22308249)；中国博士后科学基金项目(2023M732587,2024T170644)；天津市普通高等学校本科教学质量与教学改革研究计划(2025)重点项目(A251005608)

Precision control of nitration reactions based on flow chemistry: an integrated chemistry experiment

Zhide Li, Yihong Liu, Zhuqing Ma, Daofan Ma, Guangwei Wang, Wentao Zhao, Xiangwei Ren

Department of Chemistry, School of Science, Tianjin University, Tianjin 300354, China

Received:2026-05-11 Accepted:2026-07-22
Contact: Xiangwei Ren E-mail:xiangwei_ren@tju.edu.cn

摘要/Abstract

摘要： 针对本科实验教学中硝化反应安全风险高、实践长期缺失的难题，研究创新性地将连续流微反应技术引入本科实验教学，设计了本质安全、精准可控的连续流硝化反应实验。通过精准调控反应停留时间、甲苯与硝酸的摩尔比和反应温度，实现了单硝基甲苯及二硝基甲苯的选择性制备。实验教学内容高度集成有机合成实验操作、连续流微反应器技术与仪器分析方法，旨在系统训练学生的实验技能，并深化对芳香亲电取代反应机理与化工本质安全理念的理解。连续流微反应技术的引入成功解决了硝化反应在本科实验教学中长期缺失的关键问题，获得了良好的教学效果。实验有助于学生了解化工前沿技术，认识流动化学在提升过程安全中的价值，以期激发学生探索该领域未来发展的兴趣。

关键词: 流动化学, 连续流微反应器, 硝化反应, 本质安全, 实验教学

Abstract: This study addresses the persistent challenges of high safety risks and the resulting lack of hands-on practice in undergraduate nitration reaction teaching by innovatively incorporating continuous-flow microreactor technology into laboratory courses. A continuous-flow nitration experiment was designed to be inherently safe and precisely controllable, enabling the selective synthesis of mononitrotoluene and dinitrotoluene through fine-tuning of key parameters, including residence time, the molar ratio of toluene to nitric acid, and reaction temperature. The curriculum integrates organic synthesis operations, continuous-flow microreactor technology, and instrumental analysis methods, aiming to systematically enhance students’ experimental skills while deepening their comprehension of the aromatic electrophilic substitution mechanism and the principle of inherent safety in chemical engineering. The adoption of continuous-flow microreactor technology effectively resolved the critical gap of nitration experiments in undergraduate teaching and yielded favorable educational outcomes. This experiment familiarizes students with cutting-edge chemical engineering technologies and underscores the role of flow chemistry in improving process safety, with the goal of stimulating their interest in exploring future advancements in this field.

Key words: Flow chemistry, Continuous-flow microreactor, Nitration reaction, Intrinsic safety, Experimental teaching

李峙德, 刘一弘, 马竹清, 马道璠, 王光伟, 赵温涛, 任相伟. 基于流动化学的硝化反应精准调控——推荐一个综合化学实验[J]. 大学化学, 2026, (): 2605016.

Zhide Li, Yihong Liu, Zhuqing Ma, Daofan Ma, Guangwei Wang, Wentao Zhao, Xiangwei Ren. Precision control of nitration reactions based on flow chemistry: an integrated chemistry experiment[J]. University Chemistry, 2026, (): 2605016.

链接本文: https://www.dxhx.pku.edu.cn/CN/10.12461/PKU.DXHX202605016

https://www.dxhx.pku.edu.cn/CN/Y2026/V/I/2605016

参考文献

[1] K. Ju, R.E. Parales, Microbiol. Mol. Biol. Rev. 2010, 74 (2), 250.
[2] A.E.S. Nosseir, A. Cervone, A. Pasini, Aerospace 2021, 8 (1), 20.
[3] 邢其毅, 徐瑞秋, 裴伟伟, 裴坚. 基础有机化学. 第4版. 北京: 北京大学出版社, 2016.
[4] 天津大学有机化学教研室. 有机化学. 第6版. 北京: 高等教育出版社, 2019.
[5] 陈利平. 甲苯硝化反应热危险性的实验与理论研究[博士学位论文]. 南京: 南京理工大学, 2009.
[6] 安胜姬, 吕蕾, 郑松志. 实验室研究与探索, 2018, 37 (1), 150.
[7] 宋璟, 王玉军, 邓建, 陈光文, 骆广生. 化工学报, 2024, 75 (11), 3911.
[8] 马韶阳, 徐涵卓, 张亮亮, 孙宝昌, 邹海魁, 罗勇, 初广文. 化工学报, 2024, 75 (3), 727.
[9] F.A. Leibfarth, M.G. Russell, D.M. Langley, H. Seo, L.P. Kelly, D.W. Carney, J.K. Sello, T.F. Jamison, J. Chem. Educ. 2018, 95 (8), 1371.
[10] B. König, P. Kreitmeier, P. Hilgers, T. Wirth, J. Chem. Educ. 2013, 90 (7), 934.
[11] N. Emmanuel, G. Emonds-Alt, M. Lismont, G. Eppe, J.M. Monbaliu, J. Chem. Educ. 2017, 94 (6), 775.
[12] D. Perera, J.W. Tucker, S. Brahmbhatt, C.J. Helal, A. Chong, W. Farrell, P. Richardson, N.W. Sach, Science 2018, 359 (6374), 429.
[13] 工业和信息化部办公厅关于印发第一批先进适用技术名单的通知. [2025-09-21]. https://www.miit.gov.cn/zwgk/zcwj/wjfb/tz/art/2025/art_bfbaece3e3e04e0fbf074c46f8b7ae04.html
[14] L. Malet-Sanz, F. Susanne, J. Med. Chem. 2012, 55 (9), 4062.
[15] M.C. Ince, B. Benyahia, G. Vilé, ACS Sustainable Chem. Eng. 2025, 13 (7), 2864.
[16] 教育部等五部门关于印发《普通高等教育学科专业设置调整优化改革方案》的通知. [2025-09-21]. http://www.moe.gov.cn/srcsite/A08/s7056/202304/t20230404_1054230.html?eqid=d6976592000a990800000004643e7ae5
[17] G. Aridoss, K.K. Laali, J. Org. Chem. 2011, 76 (19), 8088.