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Selective hydrogenation of nitriles to imines over a multifunctional heterogeneous Pt catalyst

Authors

  • Jilan Long,

    1. Key Laboratory of Fuel Cell Technology of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China
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  • Biaolin Yin,

    1. Key Laboratory of Fuel Cell Technology of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China
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  • Yingwei Li,

    Corresponding author
    1. Key Laboratory of Fuel Cell Technology of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China
    • Correspondence concerning this article should be addressed to Y. Li at liyw@scut.edu.cn.

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  • Lianjie Zhang

    1. Key Laboratory of Specially Functional Materials of MoE, Inst. of Polymer Optoelectronic Materials & Devices, South China University of Technology, Guangzhou, China
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Abstract

Imines and their derivatives are versatile synthetic intermediates for the industrial preparation of both bulk and fine chemicals and for pharmaceuticals, but preparing these compounds efficiently through direct hydrogenation of nitriles are hindered by overhydrogenation to secondary amines. Here we report a highly efficient multifunctional catalyst system for selective hydrogenation coupling of nitriles to secondary imines using a heterogeneous Pt catalyst that was deposited on a nickel-based metal-organic framework (MOF) containing DABCO. The catalyst showed excellent synergy in promoting the hydrogenation of a variety of nitriles, giving significantly improved activity and selectivity (up to >99% yield) even under atmospheric pressure of H2. It is suggested that the Lewis base (DABCO) sites on the Ni-MOF inhibit further hydrogenation of the imines. The influence of H2 pressure, reactant concentration, stirring speed, and reaction temperature was investigated. The kinetics and mechanism of hydrogenation of benzonitrile (BN) by the Pt/Ni-MOF catalyst has been studied. The reaction showed a first-order dependence on both BN concentration and H2 pressure. A kinetic model was proposed based on the mechanism of nitriles hydrogenation and compared with experimental observations. © 2014 American Institute of Chemical Engineers AIChE J, 60: 3565–3576, 2014

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