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

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

Authors :
Helen L. Ngo
Kerby C. Jones
Thomas A. Foglia
Source :
Journal of the American Oil Chemists' Society. 83:629-634
Publication Year :
2006
Publisher :
Wiley, 2006.

Abstract

The self-metathesis of readily available monounsaturated FA has the potential of being an important pathway for the synthesis of symmetrical long-chain unsaturated-α,ω-dicarboxylic acids (C18−C26). Previous studies on the self-metathesis of monounsaturated FA esters using ruthenium catalysts in solution, however, suffered from low conversions as a result of the thermodynamic control of the reaction. We have found that the second-generation Grubbs catalyst can effectively catalyze the solvent-free self-metathesis of monounsaturated FA of varying purity (from 90 to 99%) to afford two important products—monounsaturated dicarboxylic acids and hydrocarbons—in very high molar conversions (>80%). This solvent-free self-metathesis reaction also works for monounsaturated FA containing additional functional groups. Reactions were conducted at catalyst loadings as low as 0.005 mol%, and turnover numbers as high as 10,800 could be obtained. This discovery represents an attractive approach to the large-scale production of useful monounsaturated-α,ω-dicarboxylic acids and long-chain unsaturated hydrocarbons by means of this solvent-free ruthenium-catalyzed self-metathesis of readily available monounsaturated FA.

Details

ISSN :
0003021X
Volume :
83
Database :
OpenAIRE
Journal :
Journal of the American Oil Chemists' Society
Accession number :
edsair.doi...........594814830636781ea8c90d8627e9cbe2
Full Text :
https://doi.org/10.1007/s11746-006-1249-0