Cu(I)/TEMPO体系催化空气氧化苄醇——一个有机化学综合实验设计  

Air Oxidation of Benzyl Alcohol Catalyzed by Cu(I)/TEMPO System:An Comprehensive Experiment Design of Organic Chemistry

作　　者：奉强 王思宇 李倩意 王晓月 何冰 Qiang Feng;Siyu Wang;Qianyi Li;Xiaoyue Wang;Bing He(Chemical Basis and Innovation Sichuan Experimental Teaching Demonstration Center,College of Chemistry and Life Sciences,Chengdu Normal University,Chengdu 611130,China)

机构地区：[1]成都师范学院化学与生命科学学院,化学基础与创新四川省实验教学示范中心,成都611130

出　　处：《大学化学》2023年第11期195-205,共11页University Chemistry

基　　金：四川省科技计划资助(2023NSFSC0101);四川省大学生创新创业项目(S202114389166)。

摘　　要：苄醇氧化制备苯甲醛在有机化学教学中占有重要地位,但其易于操作的合成方法常因环境不友好而难以进入大学有机化学基础实验教学课堂。本文介绍一个有机化学综合实验,以氯化亚铜、2,2’-联吡啶(bpy)、N-甲基咪唑(NMI)和2,2,6,6-四甲基哌啶氧化物(TEMPO)作催化剂,空气作氧化剂,丙酮作溶剂,室温下将苄醇在少于30 min的时间内高效氧化得到苯甲醛。优选得到的组合催化体系,能通过颜色突变指示反应终点;可使实验微型化,缩短反应时间,节约实验成本;对不同电性的苄醇化合物进行拓展实验,反应具有广泛适应性。该实验一定程度上弥补了大学化学教学实验中芳醛合成实验教学资源的匮乏。The oxidation of benzyl alcoyhol to benzaldehyde plays an important role in teaching organic chemistry.However,it is often difficult to enter basic university organic chemistry experimental teaching classes because of the unfriendly environment.In this paper,a comprehensive experiment in organic chemistry is introduced.Benzyl alcohol was efficiently oxidized to benzaldehyde in less than 30 min at room temperature using cuprous chloride,2,2’-bipyridine(bpy),N-methylimidazole(NMI),and 2,2,6,6-tetramethylpiperidine oxide(TEMPO)as catalysts,air as oxidant,and acetone as solvent.The optimized combined catalytic system can indicate the endpoint of the reaction through color mutation;it can miniaturize the experiment,shorten the reaction time,and reduce experimental cost.Extensive experiments were conducted on benzyl alcohol compounds with different electrical properties,and the reaction exhibited wide adaptability.To some extent,this experiment compensates for the lack of experimental teaching resources for aromatic aldehyde synthesis in college chemistry teaching experiments.

关 键 词：有机化学综合实验 空气氧化 芳香醛 结构表征 

分 类 号：G64[文化科学—高等教育学] O6[文化科学—教育学]