[Emim]Cl-AlCl_3离子液体催化蒽与草酰氯的Friedel-Crafts酰基化反应  

Acylation of anthracene with oxalyl chloride catalyzed by [Emim]Cl-AlCl_3 ionic liquid system

作　　者：陈敏[1] 张春燕[1] 袁新华[2] 张燕[1] 刘华[1] 程晓农[2] 

机构地区：[1]江苏大学化学化工学院,江苏镇江212013 [2]江苏大学材料科学与工程学院,江苏镇江212013

出　　处：《化学试剂》2007年第10期628-630,632,共4页Chemical Reagents

基　　金：国家自然科学基金资助项目(20207003);江苏大学高级人才基金资助项目(6810000019)

摘　　要：合成了重要的功能高分子中间体1,2-蒽乙二酮,最佳反应条件为:AlCl3在[Emim]Cl-AlCl3离子液体中的摩尔分数为0.67,离子液体与蒽的物质的量比为2,草酰氯与蒽物质的量比为2,反应温度为40℃,反应时间6h,1,2-蒽乙二酮产率可达91.5%,选择性达98.3%。且[Emim]Cl-AlCl3离子液体对环境污染小,并可循环使用。在相同实验条件下,对等物质的量的AlCl3、FeCl3、[Emim]Cl-AlCl3及[Emim]Cl-FeCl3的催化作用进行了对比,结果表明[Emim]Cl-AlCl3的效果最好。通过萃取、重结晶等方法得到了1,2-蒽乙二酮纯品,通过熔点测定、GC、GC/MS、FT-IR和1HNMR对反应产物进行定性和定量分析。[Bmim] Cl-AlCl3 ionic liquid was used as catalyst in the Ffiedel-Crafts acylation of anthracene with oxalyl chloride to synthesize the important macromolecular intermediate 1,2-acean- thrylenedione. The results showed that the suitable synthesis conditions of the acylation reaction were as follows ： the molar ratio of AlCl3 in [Emim]Cl-AlCl3 ionic Uquid was 0.67 ,the mass ratio of [ Emim] Cl-AlCl3 versus anthracene was 2, the mass ratio of oxalyl chloride versus anthracene was 2, the reaction temperature was 40 ℃, and the reaction time was 6 h. Under these conditions, the yield of 1,2-aceanthrylenedione was 91.5% with the selectivity reaching 98.3 % . Furthermore, [ Emim] Cl-AlCl3 showed less pollution to the environment and could be recycled. Under the same reaction conditions, the effects of AlCl3, FeCl3, [ Emim] Cl-AlCl3 and [Emim]Cl-FeCl3 at the same tool quantity on the yield and selectivity of 1,2-aeanthrylenedione were studied and the results indicated that [Emim] Cl-AlCl3 was the most effective catalyst. Pure 1,2-aceanthrylenedione was prepared by extraction and recrystallization and the structure of 1,2-aceanthrylenedione was identified by melting point measurement, GC/MS, Fr-IR and 1HNMR analyses.

关 键 词：离子液体 蒽 草酰氯 1 2-蒽乙二酮 合成 酰基化 高分子中间体 

分 类 号：O625.15[理学—有机化学]