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

Meenakshisundaram Sankar, Ewa Nowicka, Emma Carter, Damien M. Murphy, David W. Knight, Donald Bethell and Graham J. Hutchings ()
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Meenakshisundaram Sankar: Cardiff Catalysis Institute, School of Chemistry, Cardiff University
Ewa Nowicka: Cardiff Catalysis Institute, School of Chemistry, Cardiff University
Emma Carter: Cardiff Catalysis Institute, School of Chemistry, Cardiff University
Damien M. Murphy: Cardiff Catalysis Institute, School of Chemistry, Cardiff University
David W. Knight: Cardiff Catalysis Institute, School of Chemistry, Cardiff University
Donald Bethell: University of Liverpool
Graham J. Hutchings: Cardiff Catalysis Institute, School of Chemistry, Cardiff University

Nature Communications, 2014, vol. 5, issue 1, 1-6

Abstract: 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.

Date: 2014
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DOI: 10.1038/ncomms4332

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