Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 2/15/2006
Publication Date: 4/30/2006
Citation: Ngo, H., Jones, K.C., Foglia, T.A. 2006. Catalytic synthesis of value-added products from unsaturated fatty acids [abstract]. Annual Meeting and Expo of the American Oil Chemists' Society. p. 73.
Technical Abstract: Renewable agricultural products such as fats and oils are receiving increased attention as feedstocks in the production of biobased products. Over the past decades, numerous chemical methods including electrophilic, nucleophilic, and oxidative reactions and transitional metal-catalyzed reactions have been developed that convert the common fatty acids present in fats and oils to novel oleochemical compounds with improved and/or new properties over the starting fatty acid. In this study we have used both homogeneous and heterogeneous catalysts to convert unsaturated fatty acids to dicarboxylic acid and branched-chain monosaturated acid that may be potentially useful for the production of biodegradable polyesters and lubricants. First, homogeneous ruthenium-based Grubbs catalyst was used to catalyze the solvent-free self-metathesis of monounsaturated fatty acids 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 fatty acids containing additional functional groups such as ricinoleic acid. Reactions were conducted at catalyst loadings as low as 0.005 mol% and turnover numbers as high as 10,800 were achieved. In parallel studies unsaturated fatty acids such as oleic acid were converted to branched-chain fatty acids using solid Brönsted acid catalysts with high conversions (>95%) and selectivity (>80%). Branched-chain fatty acids are important in the production of lubricants since they have better oxidative stability than unsaturated fatty acids and lower melting point than saturated fatty acids. The solid acid catalysts were reusable for at least three cycles.