Elevance Renewable Sciences, Inc.

Wilmar Trading Pte Ltd.

Hiroki Kaido

Michael John Tupy

Richard L Pederson

Yann Schrodi

Timothy Walter Abraham

Choon Woo Lee

Kevin D Uptain

Charles M Tanger

James C Anderson

William H Sperber

Xiangsheng Meng

Francis Amore

Jill Louise Zullo

Alexandre A Pletnev

Earl H Wagener

Charles Tanger

Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.

Methods of making organic compounds by metathesis

Various methods are provided for metathesizing a feedstock. In one aspect, a method includes providing a feedstock comprising a natural oil, heating the feedstock to a temperature greater than 100&#xb0; C. in the absence of oxygen, holding the feedstock at the temperature for a time sufficient to diminish catalyst poisons in the feedstock, and, following the heating and holding, combining a metathesis catalyst with the feedstock under conditions sufficient to metathesize the feedstock.

Thermal methods for treating a metathesis feedstock

The invention is directed to methods of making organic compounds by metathesis and hydrocyanation. The method of the invention may be used, for example, to make industrial important organic compounds such as diacids, diesters, acid-amines, acid-alcohols, acid-nitriles, ester-amines, ester-alcohols, and ester-nitriles.

Methods of making organic compounds by metathesis and hydrocyanation

Disclosed are improved methods for conducting metathesis utilizing polyunsaturated fatty acid compositions (e.g., polyunsaturated fatty acid polyol esters, polyunsaturated fatty acids, polyunsaturated fatty esters, and mixtures), such as those found in naturally occurring oils and fats, as the starting material. The inventive methods involve hydrogenation of polyunsaturated fatty acid compositions prior to metathesis, thereby providing partially-hydrogenation compositions having a relatively higher amount of monounsaturated fatty acid species. The partially hydrogenated composition can then be subjected to metathesis to provide a metathesis product composition containing industrially useful compounds.

Metathesis methods involving hydrogenation and compositions relating to same

This disclosure relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by an olefin metathesis catalyst. According to one aspect, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with a cross metathesis partner comprised of an alpha olefinic reactant, under reaction conditions effective to allow cross-metathesis to occur, wherein the reaction conditions include a reaction temperature of at least 35&#xb0; C. The methods, compositions, reactions and reaction systems herein disclosed have utility in the fields of catalysis, organic synthesis, and industrial chemistry.

Synthesis of terminal alkenes from internal alkenes via olefin metathesis

Disclosed is a method of making hydrogenated metathesis products comprising the steps of: (a) providing a metathesis composition; (b) providing a metathesis catalyst comprising a transition metal; (c) metathesizing at least a portion of the metathesis composition in the presence of the metathesis catalyst to form a first composition comprising one or more metathesis products and a transition metal; (d) hydrogenating at least a portion of the first composition in the presence of a hydrogenation catalyst to form a second composition comprising one or more hydrogenated metathesis products, transition metal, and hydrogenation catalyst; and (e) removing at least a portion of the hydrogenation catalyst from the second composition, wherein the removal of the hydrogenation catalyst removes at least a portion of the transition metal of the metathesis catalyst from the second composition.

Method of making hydrogenated metathesis products

The invention provides surface coating compositions comprising a preservative comprising 9-decenoic acid, salts of 9-decenoic acid, esters of 9-decenoic acid, or combinations thereof. The surface coating compositions may be water-based coatings (e.g., a latex paint) or solvent-based coatings (e.g., a solvent-based paint). The surface coating compositions may be paints, stains, varnishes, concrete coatings, anti-graffiti coatings, and the like. Methods for protecting a surface coating composition from in-can spoilage and protecting a coating of the surface coating composition from deterioration by the action of microorganisms are also described.

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Eden Prairie, MN, United States of America

Hiroki Kaido