The application of supported palladium catalysts for the hydrogenation of aromatic nitriles

McMillan, L., Gilpin, L. F., Baker, J., Brennan, C., Hall, A., Lundie, D. T. and Lennon, D. (2016) The application of supported palladium catalysts for the hydrogenation of aromatic nitriles. Journal of Molecular Catalysis A: Chemical, 411, pp. 239-246. (doi: 10.1016/j.molcata.2015.10.028)

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Abstract

The use of a Pd/C catalyst in the liquid phase hydrogenation of various nitriles (benzonitrile, benzyl cyanide, 3-phenyl propionitrile and cinnamonitrile) has been studied in order to assess the effectiveness of this type of catalyst for this class of reaction. On modifying the nitrile substituent and upon introducing conjugation, varying degrees of conversion are observed. For benzyl cyanide and 3-phenylpropionitrile, incomplete mass balance profiles are linked to spill-over to the carbon support. In the case of benzonitrile hydrogenation, a hydrogenolytic step leads to a loss of selectivity to the primary amine to yield toluene with, ultimately, complete selectivity. Co-hydrogenation measurements on mixtures of benzonitrile and benzylamine indicate the presence of site-selective chemistry. Co-hydrogenation studies on mixtures of benzonitrile and benzyl cyanide highlight the competitive nature of the reaction system and, indirectly, establish a contribution from adsorbed imine species.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:McMillan, Mr Liam and Gilpin, Miss Lauren and Lennon, Professor David
Authors: McMillan, L., Gilpin, L. F., Baker, J., Brennan, C., Hall, A., Lundie, D. T., and Lennon, D.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Molecular Catalysis A: Chemical
Publisher:Elsevier
ISSN:1381-1169
ISSN (Online):1873-314X|
Copyright Holders:Copyright © 2015 Elsevier B.V.
First Published:First published in Journal of Molecular Catalysis A: Chemical 411:239-246
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher

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