The Anodic Oxidation of a Propionate-Propionic Acid Solution in the Presence of Several Organic Compounds

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The anodic oxidation of the propionate anion in aqueous solutions of propionic acid at a platinum electrode has been studied in the presence of several organic compounds in order to demonstrate the formation of both propionoxy and ethyl radicals as the reaction intermediates. One of the following organic compounds was added to each solution: two vinyl monomers (acrylic acid and acrylamide), two alkylbenzenes (toluene and cumene), and two aliphatic alcohols (methanol and isopropanol). The electrooxidation of sodium propionate in the presence of acrylamide resulted in polymerization, which was confirmed to be initiated by the ethyl radical. Acrylic acid, unlike acrylamide, gave no polymers. In this case, both the current efficiency for the formation of carbon dioxide and the yield ratio of ethylene to carbon dioxide were always less than those observed in the absence of acrylic acid. While the addition of alcohols gave no definite results, the addition of toluene or cumene resulted in an appreciable decrease in the yield ratio of ethylene to carbon dioxide, but affecting neither the ratio of ethane to carbon dioxide nor the current efficiency for the carbon-dioxide evolution. These results indicate that the anodic oxidation of the propionate anion proceeds through the consecutive formation of propionoxy and ethyl radicals as the reaction intermediates.
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