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

McAllister, Mairi I. ¹Boulho, Cedric ¹McMillan, Liam ¹Gilpin, Lauren F. ¹Wiedbrauk, Sandra ¹Brennan, Colin ²Lennon, David¹

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作者信息

1. Univ Glasgow, Sch Chem, Joseph Black Bldg, Glasgow G12 8QQ, Lanark, Scotland
2. Syngenta, Jeallots Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
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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.

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出版年

2018

RSC Advances

EIISTP

ISSN：

被引量8

参考文献量34

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