Oxidative decarboxylation of unsaturated fatty acids

Abstract

Long-chain internal olefins were prepared by silver(II)-catalyzed oxidative decarboxylation of unsaturated fatty acids by sodium peroxydisulfate. Similar to saturated carboxylic acids, 1-alkenes were the major decarboxylation product in the additional presence of copper(II), whereas in the absence of copper(II) alkanes were predominantly formed. In both cases, the internal unsaturation of the fatty acids remained largely intact, although the moderate yields indicated that side reactions occurred to a significant extent. The simple procedure makes this multistep one-pot reaction useful for the synthesis of a variety of internally unsaturated hydrocarbons. The purified products, almost all of which are prepared for the first time, may serve as reference compounds for studies on the heterogeneously catalyzed decarboxylation of triglycerides and fatty acids in the absence of hydrogen. Practical applications: The products of the chemistry described in this contribution, i.e., unsaturated long-chain hydrocarbons, provide bio-based building blocks for further chemical modification toward products which may be applied as (bio)fuels, lubricants, solvents, and polymeric materials.