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

The United States of America As Represented by the Secretary of

Other

Thomas A Foglia

Helen Ngo

William N Marmer

Alberto Nunez

George Piazza

Ki-Teak Lee

Michael J Haas

Richard D Ashby

Daniel Solaiman

Donald D Brillhart

Jonathan A Zerkowski

Gerhard Maerker

Yoshio Nakano

Theodore Perlstein

Siyuan Shen

Shu-I Tu

An-Fei Hsu

Lloyd A Nelson

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 sophorolid produced by a method involving reacting a compound of formula I with a compound of formula II wherein

Charged sophorolipids and sophorolipid containing compounds

The present invention relates to a method for producing fatty acid alkyl esters, involving transesterifying a feedstock containing lipid-linked fatty acids with an alcohol and an alkaline catalyst to form fatty acid alkyl esters. The feedstock has not been previously treated to release the lipid components of said feedstock, or the feedstock has been previously treated to release lipid components and the feedstock contains residual lipids (e.g., &#x3c;about 30% of the original content of lipids).

Production of fatty acid alkyl esters

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.

Method of producing dicarboxylic acids

A method has been discovered for the epoxidation of a compound having at least one carbon-carbon double bond, the method involves reacting a compound having at least one carbon-carbon double bond, a solvent, an oxidant, and membrane bound peroxygenase. Also discovered is a method for preparing the membrane bound peroxygenase involving grinding seeds containing peroxygenase to produce ground seeds, homogenizing the ground seeds in a buffer to form a slurry, centrifuging the slurry to produce a first supernatant, centrifuging the first supernatant to produce a second supernatant, and filtering said second supernatant through a protein-binding membrane filter to produce membrane bound peroxygenase; optionally the second supernatant is filtered through a hydrophilic membrane filter prior to filtering the second supernatant through a protein-binding membrane filter.

Epoxidation of carbon-carbon double bond with membrane bound peroxygenase

Lipid compositions enriched in unsaturated fatty acid-containing triacylglycerols are made from menhaden oil (MO) and partially hydrogenated menhaden oil (PHMO) to provide a lipid composition containing enriched monounsaturated fatty acid esters (MUFAs) and polyunsaturated fatty acid esters (PUFAs).

Solvent fractionation of menhaden oil and partially hydrogenated menhaden oil for making lipid compositions enriched in unsaturated fatty acid-containing triacylglycerols

Lipid compositions enriched in unsaturated fatty acid-containing triacylglycerols are made from chicken fat. The method involves solvent fractionation of chicken fat to provide a lipid composition containing enriched monounsaturated fatty acid esters (MUFAs) and polyunsaturated fatty acid esters (PUFAs).

Solvent fractionation of chicken fat for making lipid compositions enriched in unsaturated fatty acid-containing triacylglycerols

Immobilized bioactive protein compositions are prepared containing a bioactive protein such as an enzyme intercalated into galleries of a phyllosilicate, and a crosslinking compound crosslinking the phyllosilicate and the bioactive protein. The phyllosilicate may contain sodium or alkylammonium ions and be montmorillonite. The protein may be lipoxygenase, and crosslinking compounds include tetramethyl orthosilicate, tetraethoxy silicate, propyltrimethoxy silicate, polydimethylortho silicate and methyltrimethoxy silicate. The composition is prepared by delaminating a sodium-saturated phyllosilicate, mixing a bioactive protein with the delaminated phyllosilicate and crosslinking with a crosslinking compound. After crosslinking, the composition may be vacuum dried and ground. The composition can also be prepared by delaminating a montmorillonite, saturating the delaminated montmorillonite with sodium ions, mixing the resultant montmorillonite with an enzyme, adding tetramethyl orthosilicate, allowing crosslinking, and drying. Activities of up to 170% of free protein are achieved using the immobilized bioactive protein compositions, and the compositions retain up to 98% original activity after being stored at room temperature for two weeks.

Immobilization of bioactive protein in phyllosilicates

A method is described which utilizes lipases to transesterify triglyceride-containing substances and to esterify free fatty acids to alkyl esters using short chain alcohols. The alkyl esters are useful as alternatives or additives to automotive fuels and lubricants. The method is particularly advantageous because it utilizes inexpensive feedstocks such as animal fats, vegetable oils, rendered fats and restaurant grease as substrates.

Production of biodiesel, lubricants and fuel and lubricant additives

Complex mixtures of branched chain fatty acids or esters in which the yield of monomeric branched chain products are substantially increased and the yield of polymeric products substantially decreased are prepared by heating monounsaturated fatty acids or esters in the presence of certain combinations of catalysts.

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Lafayette Hill, PA, United States of America

Thomas A Foglia