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

Meenakshisundaram, Sankar, Nowicka, Ewa, Carter, Emma, Murphy, Damien Martin, Knight, David William, Bethell, Donald and Hutchings, Graham John 2014. The benzaldehyde oxidation paradox explained by the interception of peroxy radical by benzyl alcohol. Nature Communications 5 , 3332. 10.1038/ncomms4332

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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: Published Online
Status: Published
Schools: Cardiff Catalysis Institute (CCI)
Additional Information: Publisher PDF uploaded in accordance with policy at [accessed 22/04/16]
Publisher: Nature Publishing Group
ISSN: 2041-1723
Date of First Compliant Deposit: 22 April 2016
Last Modified: 17 May 2019 21:21

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