Selective oxidation of alkanes promoted by copper ions

Donald M. Camaioni, Michael A. Lilga, Timothy Bays Bays, John Linehan, Wendy J. Shaw, Jerome C. Birnbaum

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

A system that uses the Cu(I)/Cu(II) couple and O2 oxidizes alkanes, including methane, to alkyl ester in trifluoroacetic acid (TFA). Formation of an ester in large part protects the alkyl group from further oxidation, and the esters may then be hydrolyzed to the corresponding alcohol. We show that the system can be adapted to operate electrocatalytically with oxidation of alkane occuring in the cathodic compartment of an electrolysis cell due to the activation of O2 by electrogcnerated Cu(I) ions. The mechanism of the oxidation appears to involve alkyl radicals. Trapping by Cu(II) ions converts the alkyl radicals to the ester product. Alkyl radicals with 2 or more carbons may first convert to olefins which subsequently add TFA to give ester products. The results are compared with oxidation of alkanes in Cu(II)-H2O2-TFA.

Original languageEnglish
Title of host publicationACS Division of Fuel Chemistry, Preprints
Pages516-520
Number of pages5
Volume44
Edition3
Publication statusPublished - 1999

Fingerprint

Paraffins
Esters
Trifluoroacetic acid
Copper
Oxidation
Ions
Electrolysis
Olefins
Methane
Alcohols
Chemical activation
Carbon

ASJC Scopus subject areas

  • Energy(all)

Cite this

Camaioni, D. M., Lilga, M. A., Bays, T. B., Linehan, J., Shaw, W. J., & Birnbaum, J. C. (1999). Selective oxidation of alkanes promoted by copper ions. In ACS Division of Fuel Chemistry, Preprints (3 ed., Vol. 44, pp. 516-520)

Selective oxidation of alkanes promoted by copper ions. / Camaioni, Donald M.; Lilga, Michael A.; Bays, Timothy Bays; Linehan, John; Shaw, Wendy J.; Birnbaum, Jerome C.

ACS Division of Fuel Chemistry, Preprints. Vol. 44 3. ed. 1999. p. 516-520.

Research output: Chapter in Book/Report/Conference proceedingChapter

Camaioni, DM, Lilga, MA, Bays, TB, Linehan, J, Shaw, WJ & Birnbaum, JC 1999, Selective oxidation of alkanes promoted by copper ions. in ACS Division of Fuel Chemistry, Preprints. 3 edn, vol. 44, pp. 516-520.
Camaioni DM, Lilga MA, Bays TB, Linehan J, Shaw WJ, Birnbaum JC. Selective oxidation of alkanes promoted by copper ions. In ACS Division of Fuel Chemistry, Preprints. 3 ed. Vol. 44. 1999. p. 516-520
Camaioni, Donald M. ; Lilga, Michael A. ; Bays, Timothy Bays ; Linehan, John ; Shaw, Wendy J. ; Birnbaum, Jerome C. / Selective oxidation of alkanes promoted by copper ions. ACS Division of Fuel Chemistry, Preprints. Vol. 44 3. ed. 1999. pp. 516-520
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