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

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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)

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.

Suggested Citation

  • Meenakshisundaram Sankar & Ewa Nowicka & Emma Carter & Damien M. Murphy & David W. Knight & Donald Bethell & Graham J. Hutchings, 2014. "The benzaldehyde oxidation paradox explained by the interception of peroxy radical by benzyl alcohol," Nature Communications, Nature, vol. 5(1), pages 1-6, May.
    • Handle: RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms4332
    DOI: 10.1038/ncomms4332
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    Cited by:

    1. Joachim Nikl & Kamil Hofman & Samuel Mossazghi & Isabel C. Möller & Daniel Mondeshki & Frank Weinelt & Franz-Erich Baumann & Siegfried R. Waldvogel, 2023. "Electrochemical oxo-functionalization of cyclic alkanes and alkenes using nitrate and oxygen," Nature Communications, Nature, vol. 14(1), pages 1-11, December.

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