Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (9): 1451-1460.DOI: 10.1016/S1872-2067(16)62506-8

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Aerobic oxidative coupling of alcohols and amines to imines over iron catalysts supported on mesoporous carbon

Longlong Geng, Jinling Song, Bin Zheng, Shujie Wu, Wenxiang Zhang, Mingjun Jia, Gang Liu   

  1. Key Laboratory of Surface and Interface Chemistry of Jilin Province, College of Chemistry, Jilin University, Changchun 130012, Jilin, China
  • Received:2016-05-30 Revised:2016-07-12 Online:2016-09-21 Published:2016-09-21
  • Contact: Gang Liu
  • Supported by:

    This work was supported by the National Natural Science Foundation of China(21473073, 21473074) and the "13th Five-Year" Science and Technology Research of the Education Department of Jilin Province(2016403).

Abstract:

Direct oxidative coupling of an alcohol and amine, with air or molecular oxygen as the oxygen source, is an environmentally friendly method for imine synthesis. We developed an Fe catalyst supported on mesoporous carbon(denoted by FeOx/HCMK-3) for this reaction with excellent activity and recyclability. FeOx/HCMK-3 was prepared by impregnating HNO3-treated mesoporous carbon(CMK-3) with iron nitrate solution. The highly dispersed FeOx species give FeOx/HCMK-3 high reducibility and are responsible for the high catalytic performance. Imine synthesis over FeOx/HCMK-3 follows a redox mechanism. The oxygen species in FeOx/HCMK-3 participate in the reaction and are then regenerated by oxidation with molecular O2. The reaction involves two consecutive steps: oxidative dehydrogenation of an alcohol to an aldehyde and coupling of the aldehyde with an amine to give an imine. Oxidative dehydrogenation of the alcohol is the rate-determining step in the reaction.

Key words: Iron catalyst, Imine synthesis, Oxidative coupling, Mesoporous carbon, Molecular oxygen