固体酸催化二氟二苯甲酮和苯胺缩合合成N-(双(4-氟苯基)亚甲基)苯胺

以固体酸为催化剂,4,4’-二氟二苯甲酮与苯胺脱水缩合,合成了N-(双(4-氟苯基)亚甲基)苯胺.比较了不同固体酸催化剂H型ZSM-5、Na型ZSM-5、介孔分子筛MCM-41(Al)及强酸型离子交换树脂Amberlyst 15的催化效果.使用比表面、NH3-TPD对催化剂进行了表征,并与催化效果关联.考察了催化剂用量、原料摩尔比、浓度及溶剂等反应条件对产物收率的影响.产物通过熔点、核磁共振谱进行了表征.结果表明,HZSM-5固体酸催化剂具有优异的催化作用.在优化条件下,以对二甲苯为反应溶剂和脱水剂,4,4’-二氟二苯甲酮0.1 mol,苯胺0.2 mol,催化剂用量2.0 g,反应24 h,产物收率达91%.此外,催化剂易于分离,能够重复使用多次.

Synthesis of N-(bis(4-fluorophenyl)methylene)aniline from bifurobenzeketone and aniline over solid acid catalyst

N-(bis(4-fluorophenyl)methylene) was synthesized from 4,4'-bifurobenzeketone and aniline using the solid acid catalysts. The catalytic performances of different solid catalysts such as H-ZSM-5, Na-ZSM-5, MCM-41(Al) and strong ion-exchanged resin Amberlyst 15 were tested. The acidic properties of those catalysts were determined by NH3-TPD. The relationship between acidic property of catalyst and catalytic performance was explained. The reaction conditions such as the dosages of catalyst, solvents, mole ratio of aniline and bifuroenzeketone together with the concentration of reagents were investigated. The product N-(bis(4-fluorophenyl)methylene) was characterized by melting point measurement and NMR spectra. The catalytic results showed that HZSM-5 zeolite had better performance. Under the optimal conditions that dimethylbenze as solvent, 0.1 moles bifurobenzeketone, 0.2 moles aniline, and 2.0 g catalyst reacted for 12 hours, the yield of N-(bis(4-fluorophenyl)methylene) was 91%. Besides this, the solid catalyst can be easily separated and reused.