United States of America, As Represented by the Secretary of Agriculture

Helen Ngo

Thomas A Foglia

A process for preparing saturated branched chain fatty acids or alkyl esters thereof involving subjecting unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof to a skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of about 240&#xb0; C. to about 280&#xb0; C. using a combination of a sterically hindered Lewis base and zeolite as a Br&#xf6;nsted or Lewis acid catalyst, and isolating saturated branched chain fatty acids or alkyl esters thereof or mixtures thereof from the reaction mixture obtained by the skeletal isomerization reaction; wherein the process further comprises (a) recycling said catalyst by washing said catalyst with an acid solution at about 55&#xb0; C. for about 24 hours, recovering the catalyst followed by heating the catalyst at about 115&#xb0; C. for about 20 hours for the first four or five cycles of use and (b) in the next subsequent cycle recycling the catalyst by heating the catalyst at about 115&#xb0; C. for about 20 hours followed by adding Lewis base to the catalyst; steps (a) and (b) can be repeated in subsequent cycles. The yield of said saturated branched chain fatty acids is &#x2267;70 wt %. The sterically hindered Lewis base is a tertiary amine or phosphine with linear or branched C1 to C6 alkyl or phenyl groups attached thereto.

Process for preparing saturated branched chain fatty acids

A process for preparing saturated branched chain fatty acids or alkyl esters thereof involving subjecting unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof to a skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of about 240&#xb0; C. to about 280&#xb0; C. using a combination of a stericly hindered Lewis base and zeolite as a Br&#xf6;nsted or Lewis acid catalyst, and isolating saturated branched chain fatty acids or alkyl esters thereof or mixtures thereof from the reaction mixture obtained by the skeletal isomerization reaction. The yield of said saturated branched chain fatty acids is &#x2267;70 wt %. The stericly hindered Lewis base is a tertiary amine or phosphine with linear or branched C1 to C6 alkyl or phenyl groups attached thereto.

A method of producing dicarboxylic acids (e.g., &#x3b1;,&#x3c9; dicarboxylic acids) by reacting a compound having a terminal COOH (e.g., unsaturated fatty acid such as oleic acid) and containing at least one carbon-carbon double bond with a second generation Grubbs catalyst in the absence of solvent to produce dicarboxylic acids. The method is conducted in an inert atmosphere (e.g., argon, nitrogen). The process also works well with mixed unsaturated fatty acids obtained from soybean, rapeseed, tall, and linseed oils.

Growing community of inventors

North Wales, PA, United States of America

Helen Ngo