One-pot synthesis of imines from benzyl alcohol and amines on Au/ZrO2 catalyst

Cui, Wenjing, Zhu, Huaiyong, Jia, Meilin, Ao, Wulan, Zhang, Yulin, & Zhaorigetu, Bao (2013) One-pot synthesis of imines from benzyl alcohol and amines on Au/ZrO2 catalyst. Reaction Kinetics, Mechanisms and Catalysis, 109(2), pp. 551-562.

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Abstract

Imines were synthesized from benzyl alcohol and amines by using catalysts of gold nanoparticles supported on ZrO2 (Au/ZrO2). The effects of reaction time, temperature, gold loadings and base were investigated. High yields were achieved under moderate conditions (60 °C) in the presence of KOCH3. For instance, the yield of N-benzylidenebenzylamine produced from benzyl alcohol and benzylamine on 3 wt% Au/ZrO2 is 87 %. The synthesis of imine involves two reaction steps: selective oxidation of benzyl alcohol to benzaldehyde and the coupling reaction of amines with benzaldehyde. In the first step, the base promotes the selective oxidation. The reactions of benzyl alcohol with three different amines, aniline, n-butylamine and benzylamine, were conducted to produce corresponding imines. The results show that the amine with stronger nucleophilicity has better ability to react with benzaldehyde in the second step, resulting in higher yield of the corresponding imine. We proposed a tentative mechanism for the synthesis process.

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ID Code: 70926
Item Type: Journal Article
Refereed: Yes
Keywords: Imines, Catalytic synthesis, Gold nanoparticles, Benzyl alcohol, Amine
DOI: 10.1007/s11144-013-0576-z
ISSN: 1878-5204
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2013 Akade´miai Kiado´, Budapest, Hungary
Deposited On: 02 May 2014 00:52
Last Modified: 02 May 2014 01:08

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