The benzaldehyde oxidation paradox explained by the interception of peroxy radical by benzyl alcohol

Meenakshisundaram, Sankar ORCID: https://orcid.org/0000-0002-7105-0203, Nowicka, Ewa ORCID: https://orcid.org/0000-0001-7449-2720, Carter, Emma ORCID: https://orcid.org/0000-0001-6691-2377, Murphy, Damien M. ORCID: https://orcid.org/0000-0002-5941-4879, Knight, David W., Bethell, Donald and Hutchings, Graham J. ORCID: https://orcid.org/0000-0001-8885-1560 2014. The benzaldehyde oxidation paradox explained by the interception of peroxy radical by benzyl alcohol. Nature Communications 5 , .. 10.1038/ncomms4332

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Abstract

Benzaldehyde readily undergoes autoxidation to form benzoic acid on exposure to air at room temperature. Yet it can be formed in high yield from, for example, benzyl alcohol by oxidation using a variety of procedures and catalysts. Here we report the evidence to resolve this apparent paradox. It is confirmed that benzyl alcohol (and a number of other alcohols), even at low concentrations in benzaldehyde, inhibits the autoxidation. Furthermore we report on the structural features required for inhibition. Electron paramagnetic resonance spin trapping experiments demonstrate that benzyl alcohol intercepts, by hydrogen atom transfer, the benzoylperoxy radicals that play a key role in benzaldehyde autoxidation. A similar inhibition effect has also been observed for the aliphatic octanal/1-octanol system.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Additional Information:	Publisher PDF uploaded in accordance with policy at http://www.sherpa.ac.uk/romeo/issn/2041-1723/ [accessed 22/04/16]
Publisher:	Nature Research
ISSN:	2041-1723
Date of First Compliant Deposit:	22 April 2016
Date of Acceptance:	28 January 2014
Last Modified:	07 Nov 2024 22:20
URI:	https://orca.cardiff.ac.uk/id/eprint/61931

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