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Solvent-Free Aerobic Epoxidation of Dec-1-ene Using Gold/Graphite as a Catalyst

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Abstract

The oxidation of dec-1-ene has been investigated using gold nanoparticles supported on graphite in the presence of a radical initiator (α,α-azobisisobutyronitrile) using oxygen from air as oxidant. We have investigated the influence of the reaction temperature (70–100 °C), catalyst mass and reaction time on the epoxide yield. In the absence of a radical initiator the reaction does not proceed, although auto-oxidation can occur at higher temperatures in the range studied. However, in the presence of an initiator, selective oxidation occurs and the initiator propagates the reaction through the formation of a peroxy-radical at the allylic C3 position. Graphite enhances the formation of the allylic products dec-1-en-3-ol, dec-1-en-3-one, and dec-2-en-1-ol; however, the addition of gold nanoparticles to the graphite, enhances formation of 1,2-epoxydecane. It is suggested that gold suppresses the formation of allylic products via a Russell termination.

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Acknowledgments

The authors thank Sasol, Mintek Cardiff University for funding this work.

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Author notes

  1. Nicholas F. Dummer

    Present address: Faculty of Science, University of Wollongong, Wollongong, NSW, 2522, Australia

Authors and Affiliations

  1. Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Park Place, Cardiff, CF10 3AT, UK

    Upendra Nath Gupta, Nicholas F. Dummer, Samuel Pattisson, Robert L. Jenkins, David W. Knight, Donald Bethell & Graham J. Hutchings

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  1. Upendra Nath Gupta
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Correspondence to Graham J. Hutchings.

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Gupta, U.N., Dummer, N.F., Pattisson, S. et al. Solvent-Free Aerobic Epoxidation of Dec-1-ene Using Gold/Graphite as a Catalyst. Catal Lett 145, 689–696 (2015). https://doi.org/10.1007/s10562-014-1425-z

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