Au-catalyzed epoxidation of linear alkene with molecular oxygen

Jian Jiang, Sean M. Oxford, Baosong Fu, Mayfair C. Kung, Harold H Kung

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

Selective oxidation of alkenes that possess allylic hydrogen typically requires the use of expensive and/or environmentally unfriendly oxidants such as peroxides, hydroperoxides, nitrous oxide, oxychlorides, and oxometal complexes. A much more desirable oxidant is molecular oxygen, which, however, only achieves good yield with alkenes without allylic hydrogen or by use with H2, which is potentially explosive. Highly selective epoxidation of propene and butene can be achieved using molecular oxygen in a dilute solution of water in methanol, catalyzed by a suspension of supported Au catalyst and titanium silicalite (TS-1), and using CO as the sacrificial reductant. Results of isotope labeling experiments further infer that the dominant reaction pathway proceeds via the formation of methyl hydroperoxide. The results can be explained with Au-support interface being the active site, where molecular oxygen is adsorbed as a peroxy, which reacts to form an alkyl peroxide that migrates to TS-1 to effect epoxidation.

Original languageEnglish
Title of host publicationACS National Meeting Book of Abstracts
Publication statusPublished - 2010
Event239th ACS National Meeting and Exposition - San Francisco, CA, United States
Duration: Mar 21 2010Mar 25 2010

Other

Other239th ACS National Meeting and Exposition
CountryUnited States
CitySan Francisco, CA
Period3/21/103/25/10

Fingerprint

Epoxidation
Molecular oxygen
Alkenes
Olefins
Peroxides
Oxidants
Hydrogen Peroxide
Hydrogen
Reducing Agents
Nitrous Oxide
Carbon Monoxide
Titanium
Butenes
Catalyst supports
Isotopes
Labeling
Propylene
Methanol
Suspensions
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Jiang, J., Oxford, S. M., Fu, B., Kung, M. C., & Kung, H. H. (2010). Au-catalyzed epoxidation of linear alkene with molecular oxygen. In ACS National Meeting Book of Abstracts

Au-catalyzed epoxidation of linear alkene with molecular oxygen. / Jiang, Jian; Oxford, Sean M.; Fu, Baosong; Kung, Mayfair C.; Kung, Harold H.

ACS National Meeting Book of Abstracts. 2010.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Jiang, J, Oxford, SM, Fu, B, Kung, MC & Kung, HH 2010, Au-catalyzed epoxidation of linear alkene with molecular oxygen. in ACS National Meeting Book of Abstracts. 239th ACS National Meeting and Exposition, San Francisco, CA, United States, 3/21/10.
Jiang J, Oxford SM, Fu B, Kung MC, Kung HH. Au-catalyzed epoxidation of linear alkene with molecular oxygen. In ACS National Meeting Book of Abstracts. 2010
Jiang, Jian ; Oxford, Sean M. ; Fu, Baosong ; Kung, Mayfair C. ; Kung, Harold H. / Au-catalyzed epoxidation of linear alkene with molecular oxygen. ACS National Meeting Book of Abstracts. 2010.
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