BAI Yong¹, WANG Zhiqiang¹, FU Biao¹, LIU Haiyan¹, WANG Zhijia², ZHANG Zhongbiao^1*

(1. Tianjin Key Laboratory of Water Resources and Environment, Tianjin Normal University, Tianjin 300387, China; 2. The Fifth Project Offices of Huabei Foundation Building Co., Ltd., Renqiu 062552, China)

Abstract: 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.

Key words: N-(bis(4-fluorophenyl)methylene)aniline; solid acid catalysis; HZSM-5; ketimine

E-mail: zqwang@mail.tjnu.edu.cn 

Journal of Molecular Catalysis, Vol. 26, Issue 2, 2012, 121-126