柠檬烯的绿色环氧化  

Green Epoxidation of Limonene

作　　者：张茗雨 吕佳潼 张海波 王博[1] 宋志光[1] 朱万春[1] 郭玉鹏[1] Mingyu Zhang;Jiatong Lv;Haibo Zhang;Bo Wang;Zhiguang Song;Wanchun Zhu;Yupeng Guo(College of Chemistry,Jilin University,Changchun 130012,China)

机构地区：[1]吉林大学化学学院,长春130012

出　　处：《大学化学》2023年第4期177-183,共7页University Chemistry

基　　金：2021年教育部拔尖计划2.0研究课题(20212019);2021吉林省教育科学“十四五”规划2021年度重点课题(JF2101);2021年吉林省高等教育教学改革研究课题(JLJY2021180223925);2022年吉林省高等教育教学改革研究课题(JLJY202241289021);2021年吉林大学本科教学改革研究重点资助项目(2021XZD018,2021XZD019)。

摘　　要：现代化学合成对原料来源的可持续性,工艺过程的原子经济性、安全性、节能性和环境友好性愈发重视,这也是高校化学教育的重点内容。遵循绿色可持续化学的理念,本文介绍了基于生物质原料的系列绿色化学实验中适用于有机化学基础实验教学的柠檬烯环氧化方案,以过氧磷钨杂多酸四正丁基铵盐为可回收的VPTC型催化剂,30%过氧化氢水溶液作为绿色、安全、原子经济的氧化剂,将柠檬烯选择性氧化为可用于合成可降解聚合物材料的单体分子1,2-柠檬烯环氧化物。本实验训练学生有机化学实验基本技能,加强学生对烯烃亲电加成反应中结构与活性关系的理解,相转移催化和基于红外光谱、核磁共振氢谱、气相色谱的分析方面的理论学习与实践相结合,起到巩固知识、提高学习兴趣的作用;同时还向学生传递了绿色、可持续的有机化学理念,提升对化学学科发展的信心和对科研的兴趣。Today,more attention is paid to the production of fine chemicals from sustainable raw materials via atom efficient,safe,and energy-efficient processes in modern organic synthesis.Teaching these“green”concepts also becomes a central task in chemistry education.Herein,we introduce our efforts for developing a series of teaching experiments on the chemistry of renewable substances from biomass and providing an organic chemistry module on the catalytic green epoxidation of limonene.Limonene is a monoterpene isolated from orange peels,and its 1,2-epoxide is found to copolymerize with CO_(2) leading to a high-performance biodegradable polymer.In our design,with 30%H2O2 as a safe and atom efficient oxidant,and recyclable tetrabutylammonium polyphosphotungstate as a phase transfer catalyst,limonene is efficiently oxidized to its 1,2-epoxide in a regioselective fashion.This experiment not only boosts the students’enthusiasm toward learning a structural based activity in electrophilic addition of alkenes along with 1H NMR and GC directed structural analysis,but also encourages students toward creative thinking and research in green and sustainable chemistry by demonstrating the potential of this epoxidation method on industrial production of biodegradable materials.

关 键 词：环氧化 绿色化学 柠檬烯 有机合成 

分 类 号：G64[文化科学—高等教育学] O6[文化科学—教育学]