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Electrochemical conversion of fatty acids

Schäfer, Hans J.
European journal of lipid science and technology 2012 v.114 no.1 pp. 2-9
ambient temperature, couplings, electrochemistry, electrodes, electron transfer, fatty acids, free radicals, green chemistry, pheromones, wastes
Electrochemical conversions combine an electron transfer with a chemical reaction, which allows conversions that are not available in non‐electrochemical reactions. Electrochemical conversions usually need fewer steps, produce less waste, provide a cheaper reagent, require less auxiliaries, and allow often an easier scale‐up than non‐electrochemical syntheses. In addition, they can be conducted at ambient temperature and pressure. All these qualities agree well with the rules of green chemistry. Electroactive sites for fatty acids are the carboxyl group, the CC double bond and the activated CH bond. The deprotonated carboxyl group is anodically decarboxylated to afford an alkyl radical. The radical can couple or add to a CC double bond. Radical coupling provides diesters, pheromones, or C‐glycosides. At the anode the double bond can be substituted in allylic position, add two nucleophiles or can be cleaved. Cathodic reduction of fatty acids with an enone group affords dimer fatty acids in a hydrodimerization. Non‐activated CH bonds in fatty acids can be oxygenated at the anode; the conversion occurs preferentially at the remote CH bonds.