Metathesis of unsaturated fatty acids: Synthesis of long‐chain unsaturated‐α,ω‐dicarboxylic acids

• DOI: 10.1007/s11746-006-1249-0
• Publication Date: 2006-11-28T17:58:37Z
• Authors: Helen L. Ngo; Kerby Jones; Thomas A. Foglia
• Keywords: Salt metathesis reaction; Acyclic diene metathesis

Abstract The self‐metathesis of readily available monounsaturated FA has the potential being an important pathway for synthesis symmetrical long‐chain unsaturated‐α,ω‐dicarboxylic acids (C 18 −C 26 ). Previous studies on esters using ruthenium catalysts in solution, however, suffered from low conversions as a result thermodynamic control reaction. We have found that second‐generation Grubbs catalyst can effectively catalyze solvent‐free varying purity (from 90 to 99%) afford two products—monounsaturated dicarboxylic and hydrocarbons—in very high molar (>80%). This reaction also works containing additional functional groups. Reactions were conducted at loadings 0.005 mol%, turnover numbers 10,800 could be obtained. discovery represents attractive approach large‐scale production useful monounsaturated‐α,ω‐dicarboxylic unsaturated hydrocarbons by means this ruthenium‐catalyzed FA.