The production of tyramine via the selective hydrogenation of 4-hydroxybenzyl cyanide over a carbon-supported palladium catalyst

McAllister, M. I., Boulho, C., McMillan, L., Gilpin, L., Wiedbrauk, S., Brennan, C. and Lennon, D. (2018) The production of tyramine via the selective hydrogenation of 4-hydroxybenzyl cyanide over a carbon-supported palladium catalyst. RSC Advances, 8(51), pp. 29392-29399. (doi: 10.1039/C8RA05654D)

Abstract

The selective production of primary amines is a problem that plagues heterogeneously catalysed nitrile hydrogenation reactions. Whilst the target amine tyramine (HOC6H4CH2CH2NH2) is biochemically available through the action of enzymes, synthetic routes to this species are not widely reported. Here, a heterogeneously catalysed method is proposed that utilises a Pd/C catalyst to effect the selective hydrogenation of 4-hydroxybenzyl cyanide within a three-phase reactor. The aforementioned selectivity issues are overcome by adjustment of various experimental parameters (hydrogen supply, agitation rate, temperature, use of an auxiliary agent) that result in improved catalytic performance, such that the desired tyramine salt (tyramine hydrogen sulphate) can be produced in quantitative yield. Accordingly, through consideration of the interconnectivity of hydrogenation and hydrogenolysis processes, a selective synthetic strategy is achieved with the findings suitable for extension to other substrates of this nature.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Boulho, Dr Cedric and McAllister, Mairi and McMillan, Mr Liam and Gilpin, Miss Lauren and Lennon, Professor David
• Authors: McAllister, M. I., Boulho, C., McMillan, L., Gilpin, L., Wiedbrauk, S., Brennan, C., and Lennon, D.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: RSC Advances
• Publisher: Royal Society of Chemistry
• ISSN: 2046-2069
• ISSN (Online): 2046-2069
• Published Online: 20 August 2018
• Copyright Holders: Copyright © 2018 The Royal Society of Chemistry
• First Published: First published in RSC Advances 8(51): 29392-29399
• Publisher Policy: Reproduced under a Creative Commons License

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
55785	1	KTA - EPSRC: Development of a reaction scheme and kinetic model for the hydrogenation of aromatic nitriles over supported palladium catalysts.	David Lennon	Engineering and Physical Sciences Research Council (EPSRC)	EP/H500138/1	CHEM - CHEMISTRY