The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding

A carbon supported Pd catalyst is used in the liquid phase hydrogenation of the aromatic cyanohydrin mandelonitrile (C(6)H(5)CH(OH)CH(2)CN) to afford the primary amine phenethylamine (C(6)H(5)CH(2)CH(2)NH(2)). Employing a batch reactor, the desired primary amine is produced in 87% selectivity at rea...

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Autores principales: McAllister, Mairi I., Boulho, Cédric, McMillan, Liam, Gilpin, Lauren F., Brennan, Colin, Lennon, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070305/
https://www.ncbi.nlm.nih.gov/pubmed/35531026
http://dx.doi.org/10.1039/c9ra04618f
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author McAllister, Mairi I.
Boulho, Cédric
McMillan, Liam
Gilpin, Lauren F.
Brennan, Colin
Lennon, David
author_facet McAllister, Mairi I.
Boulho, Cédric
McMillan, Liam
Gilpin, Lauren F.
Brennan, Colin
Lennon, David
author_sort McAllister, Mairi I.
collection PubMed
description A carbon supported Pd catalyst is used in the liquid phase hydrogenation of the aromatic cyanohydrin mandelonitrile (C(6)H(5)CH(OH)CH(2)CN) to afford the primary amine phenethylamine (C(6)H(5)CH(2)CH(2)NH(2)). Employing a batch reactor, the desired primary amine is produced in 87% selectivity at reaction completion. Detection of the by-product 2-amino-1-phenylethanol (C(6)H(5)CH(OH)CH(2)NH(2)) accounts for the remaining 13% and closes the mass balance. The reaction mechanism is investigated, with a role for both hydrogenation and hydrogenolysis processes established.
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spelling pubmed-90703052022-05-05 The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding McAllister, Mairi I. Boulho, Cédric McMillan, Liam Gilpin, Lauren F. Brennan, Colin Lennon, David RSC Adv Chemistry A carbon supported Pd catalyst is used in the liquid phase hydrogenation of the aromatic cyanohydrin mandelonitrile (C(6)H(5)CH(OH)CH(2)CN) to afford the primary amine phenethylamine (C(6)H(5)CH(2)CH(2)NH(2)). Employing a batch reactor, the desired primary amine is produced in 87% selectivity at reaction completion. Detection of the by-product 2-amino-1-phenylethanol (C(6)H(5)CH(OH)CH(2)NH(2)) accounts for the remaining 13% and closes the mass balance. The reaction mechanism is investigated, with a role for both hydrogenation and hydrogenolysis processes established. The Royal Society of Chemistry 2019-08-21 /pmc/articles/PMC9070305/ /pubmed/35531026 http://dx.doi.org/10.1039/c9ra04618f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
McAllister, Mairi I.
Boulho, Cédric
McMillan, Liam
Gilpin, Lauren F.
Brennan, Colin
Lennon, David
The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding
title The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding
title_full The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding
title_fullStr The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding
title_full_unstemmed The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding
title_short The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding
title_sort hydrogenation of mandelonitrile over a pd/c catalyst: towards a mechanistic understanding
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9070305/
https://www.ncbi.nlm.nih.gov/pubmed/35531026
http://dx.doi.org/10.1039/c9ra04618f
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