Reactions of carbon monoxide with unsaturated fatty acids and derivatives: A review

The important reactions of carbon monoxide with unsaturated fatty derivatives that are reviewed in this paper include hydroformylation (the oxo reaction), Koch carboxylation and Reppe carbonylation. With oleic acid as a substrate, the products are C19 bifunctional compounds e.g., formyl‐ or carboxy‐stearic acid. Double bond isomerization before carbon monoxide addition is characteristic of these catalytic reactions; additionally, rearrangement to introduce methyl branching occurs in the Koch carboxylation. Isomerization does not occur when a rhodium‐triphenylphosphine catalyst replaces cobalt in the oxo reaction. Properties of the C19 dicarboxylic acids differ and depend upon method of preparation: Many areas of application have been reported for C19 compounds‐lubricants, plasticizers, polyurethanes, epoxy resins, leather and other coatings, unsaturated polyester resins and transparent polyamide plastics.