2,6-二甲基喹啉的一锅法合成  

One-pot Synthesis of 2,6-Dimethylquinoline

作　　者：汪小华 苏倡[2] WANG Xiaohua SU Chang(Elementary Education,Tongji Zhejiang College,Jiaxing Zhejiang 314000,China ,Institute of Chemical Technology,Ningbo Polytechnic,Ningbo Zhejiang 315800,China)

机构地区：[1]同济大学浙江学院基础部,浙江嘉兴314000 [2]宁波职业技术学院化工学院,浙江宁波315800

出　　处：《太原理工大学学报》2017年第5期728-734,746,共8页Journal of Taiyuan University of Technology

摘　　要：在Cu-Pd/γ-Al_2O_3催化剂作用下,用对硝基甲苯、乙醇和水一锅法合成2,6-二甲基喹啉,考察了反应条件(包括反应时间、反应温度、反应压力、乙醇和水用量)的影响规律。结果表明,在温度453K,压力3.5MPa,对硝基甲苯18g,乙醇60mL,水30mL,催化剂1g,反应时间12h时,反应效果最佳;此时,对硝基甲苯转化率为100%,2,6-二甲基喹啉选择性为68.97%.在最佳反应条件下,添加不同的金属助剂(包括锌、锡、铁、钴、镍、钼和镧)对Cu-Pd/γ-Al_2O_3催化剂进行改性;结果显示,以铁助剂效果为最佳,此时2,6-二甲基喹啉的选择性由68.97%提升至71.08%.该合成工艺实现了转移加氢、羟醛缩合、加成反应、脱水成环、脱氢等多步反应的耦合,简化了工艺路线,有望解决产品分离和催化剂回收等问题,为含多取代基的喹啉类化合物的合成提供了新路径。The effects of reaction conditions including reaction time,temperature,pressure,ethanol and water content on one-pot synthesis of 2,6-dimethylquinoline（2,6-DiMeQ）from 4-nitrotoluene and ethanol over Cu-Pd/γ-Al_2O_3 catalyst were studied.The conversion of p-nitrotoluene and the selectivity of 2,6-dimethylquinoline reached 100% and 68.97%respectively,after 12 h under the optimal reaction conditions of T=453K,p=3.5 MPa,18 g of p-nitrotoluene,60 mL of ethanol,30 mL of water and 1g of Cu-Pd/γ-Al_2O_3.With iron promoted Cu-Pd/γ-Al_2O_3 catalyst,the selectivity of 2,6-dimethylquinoline was increased to 71.08%.The reaction realizes the coupling of multi-reactions including hydrogen transfer hydrogenation from ethanol to 4-nitrotoluene,aldol-condensation of aldehyde,Michael-addition of 4-methylaniline and unsaturated aldehydes,dehydration-cyclization and dehydrogenation.Therefore,such one-pot process significantly simplifies the procedure for 2,6-dimethylquinoline production,as well as solves the problems of product separation and catalyst recovery,thus providing a new path for synthesis of quinoline and its derivatives.

关 键 词：喹啉 一锅法 多相催化 双金属催化剂 AL2O3催化剂 金属助剂 2 6-二甲基喹啉 Cu-Pd/γ-Al2O3 

分 类 号：TQ25[化学工程—有机化工]