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.
|Title of host publication||ACS Division of Fuel Chemistry, Preprints|
|Number of pages||5|
|Publication status||Published - 1999|
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