大学化学 >> 2023, Vol. 38 >> Issue (2): 177-184.doi: 10.3866/PKU.DXHX202205011

化学实验 上一篇    下一篇

格氏试剂的合成实验改进

张恒, 幸志荣, 刘冬, 周志彬, 冯文芳()   

  • 收稿日期:2022-05-06 录用日期:2022-06-16 发布日期:2022-06-29
  • 通讯作者: 冯文芳 E-mail:fengwenfang@mail.hust.edu.cn
  • 基金资助:
    中央高校基本科研业务费HUST(2020kfyXJJS095)

Improvement on Synthesis of Grignard Reagent

Heng Zhang, Zhirong Xing, Dong Liu, Zhibin Zhou, Wenfang Feng()   

  • Received:2022-05-06 Accepted:2022-06-16 Published:2022-06-29
  • Contact: Wenfang Feng E-mail:fengwenfang@mail.hust.edu.cn

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摘要：

采用二异丁基氢化铝(DIBAH)替代分子碘，对格氏试剂的合成实验进行了改进，系统研究了DIBAH引发对反应体系安全性的影响，以及不同结构卤代烃底物在DIBAH引发下对格氏反应速率的影响。结果表明，添加2% (摩尔分数，以卤代烃的摩尔量为基础)的DIBAH，可以在温和(20 ℃)条件下，高效合成苯基溴化镁、正丁基溴化镁等两种典型的格氏试剂，并能获得比分子碘引发体系更高产率的格氏反应产物。本工作通过提高格氏试剂合成反应的安全性，加强学生对实验安全的重视，引导学生关注化工产业实践中的实际问题。通过对反应体系的优化和结构解析，引导学生将基础知识活学活用、融会贯通。

关键词: 实验安全, 格氏试剂, 三苯甲醇, 2-甲基-2-己醇

Abstract:

In this work, the synthesis of Grignard reagent is improved by replacing molecular iodine with diisobutylaluminum hydride (DIBAH). Systematic investigations on the influence of DIBAH initiation on the safety of the reaction system and the chemical structure of haloalkanes are performed. It has been demonstrated that the addition of 2 mol% DIBAH (vs. the molar content of haloalkanes) allows the reaction to take place under mild condition (20 ℃), yielding phenyl magnesium bromide and n-butyl magnesium bromide with high efficiency. With the improved safety on modified Grignard reactions, the students could get a deeper understanding on the importance of safety in chemical reactions. In particular, the present work could also help students to pay attention to safety of organic experiments and the dilemmas encountered by practical applications, and better cope with the gap between fundamental research and industrial applications.

Key words: Experimental safety, Grignard reagent, Triphenylmethanol, 2-Methyl-2-hexanol