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

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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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Acknowledgments

Financial supports from the National Natural Science Foundation of China, No. 20966008 and Opening Project of Natural Science Foundation of Inner Mongolia, No. 2010KF02 are gratefully acknowledged.

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Authors and Affiliations

  1. College of Chemical Engineering, Inner Mongolia University of Technology, Hohhot, 010051, China

    Wenjing Cui

  2. School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology, Brisbane, QLD, 4001, Australia

    Huaiyong Zhu

  3. Inner Mongolia Key Laboratory of Green Catalysis, College of Chemistry and Environmental Science, Inner Mongolia Normal University, Hohhot, 010022, China

    Meilin Jia, Wulan Ao, Yulin Zhang & Bao Zhaorigetu

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  1. Wenjing Cui
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  2. Huaiyong Zhu
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  3. Meilin Jia
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  6. Bao Zhaorigetu
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Correspondence to Bao Zhaorigetu.

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Cui, W., Zhu, H., Jia, M. et al. One-pot synthesis of imines from benzyl alcohol and amines on Au/ZrO2 catalyst. Reac Kinet Mech Cat 109, 551–562 (2013). https://doi.org/10.1007/s11144-013-0576-z

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