卤素交换法绿色合成1,3-二溴丙酮——推荐一个基础有机合成教学实验  

Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method:Recommending a Basic Organic Synthesis Teaching Experiment

作　　者：苏胤伍 郑绚文 杜江辉 李伯达 王涛[1] 黄治炎 Yinwu Su;Xuanwen Zheng;Jianghui Du;Boda Li;Tao Wang;Zhiyan Huang(School of Chemistry&Chemical Engineering,Shaanxi Normal University,Xi’an 710119,China)

机构地区：[1]陕西师范大学化学化工学院,西安710119

出　　处：《大学化学》2024年第5期307-314,共8页University Chemistry

基　　金：国家自然科学基金面上项目(21872090)。

摘　　要：基于有机合成方法学研究的一般过程,围绕“科学问题为目标导向”的实验教学指导原则,本文将1,3-二溴丙酮的绿色合成工艺开发为有机化学基础教学实验,首次将卤素交换反应应用于实验教学中。以1,3-二氯丙酮和溴化锂为原料,采用二氯甲烷和丙酮组成的混合溶剂(体积比10:1)打破卤素交换反应平衡,有效促进正向反应进行。在此基础上,本文使用3.5当量溴化锂,40℃回流反应1.5 h,以97%的分离产率实现了1,3-二溴丙酮的绿色合成,纯度高于97%,精制后纯度为98.8%。本实验所用试剂环境友好,安全性高,教学时长约为4 h,不仅涉及多种有机化学实验的基本操作,还包含反应监测、结构表征、纯度分析等重要环节,非常适合用于有机化学基础实验教学。同时,以本实验方案为蓝本,结合有关卤素交换反应发展历史和1,3-二溴丙酮应用发展的微课学习和拓展练习,实现理论知识与合成实践之间的互动,提升化学专业本科生解决有机合成问题的综合能力,夯实化学类人才的培养质量。Based on the general process of synthetic chemistry methodology and the“scientific problem-oriented”principle in laboratory teaching,this paper has developed a basic experiment of organic chemistry derived from the green synthesis of 1,3-dibromoacetone,and firstly applied halogen exchange reaction to laboratory teaching.Starting with 1,3-dichloroacetone and lithium bromide,the halogen exchange equilibrium was broken efficiently using mixture solvent of dichloromethane and acetone(10:1).Therefore,in the presence of 3.5 equivalents of lithium bromide,the green synthesis of 1,3-dibromoacetone was achieved with 97%isolated yield after refluxing 1.5 hours at 40℃.The purity of desired product was higher than 97%,and up to 98.8%after recrystallization.The all reagents used in this experiment are safe and environmentally benign.The teaching time is about 4 hours,which not only involves basic operations of various organic chemistry experiments,but also includes important aspects such as reaction monitoring,structure characterization,and purity analysis.It is very suitable for basic organic chemistry laboratory teaching.At the same time,based on this experimental scheme,combined with the micro-course learning and exercises on the development history of halogen exchange reaction in application and development of 1,3-dibromoacetone,the interaction between theoretical knowledge and synthetic practice was realized.This improved the comprehensive ability of undergraduate of chemistry majors to solve synthetic chemistry problems and solidified the quality of talent cultivation in the field of chemistry.

关 键 词：绿色化学 卤素交换 1 3-二氯丙酮 1 3-二溴丙酮 溴化锂 

分 类 号：G64[文化科学—高等教育学] O6[文化科学—教育学]