Abstract: Conjugated diene acids and derivatives thereof, are disclosed herein. In some embodiments, the conjugated diene acids and derivatives thereof are derived from the metathesis of a natural oil followed by isomerization. Uses of conjugated diene acids and derivatives thereof in various compositions are also disclosed herein.

Abstract: This invention relates to unsaturated polyol esters that can be used in hydraulic fluid applications, including fire-resistant hydraulic fluid applications, marine hydraulic fluid applications, metalworking fluid applications, food grade fluid applications, and transformer fluid applications, and methods for making the same.

Abstract: Low-color ester compositions and methods of making low-color ester compositions are generally disclosed. In certain embodiments, methods of making low-color ester compositions from a biorefinery bottoms stream are disclosed. In some other embodiments, methods for recovering esters of 1,18-octadecanedioic acid are disclosed.

Abstract: A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent selected from the group consisting of (i) a salt and/or an ester of a phosphorous oxo acid, (ii) a derivative of the phosphorous oxo acid in which at least one P—H bond has been replaced by a P—C bond, (iii) a salt and/or an ester of the derivative, and (iv) combinations thereof; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product.

Abstract: The oligomerization of certain carboxylic acids and alkyl esters derived from natural oils is disclosed. This includes the oligomerization of C10-17 unsaturated carboxylic acids such as 9-decenoic acid, where the oligomerization yields a mixture of mono-, di- and tri-carboxylic acids. This also includes the oligomerization of certain alkyl esters, including the oligomerization of C10-17 unsaturated alkyl esters such as methyl 9-decenoate (9-DAME), where the oligomerization yields a mixture of mono-, di- and tri-carboxylic acid esters. Various end use applications for the oligomerized carboxylic acids and oligomerized alkyl esters are also disclosed.

Abstract: Various methods are provided for metathesizing a feedstock. In one aspect, a method includes providing a feedstock including a natural oil, chemically treating the feedstock under conditions sufficient to diminish catalyst poisons in the feedstock, and, following the treating, combining a metathesis catalyst with the feedstock under conditions sufficient to metathesize the feedstock.

Abstract: Aqueous compositions of carboxylic acids, carboxylate esters, and carboxylate salts are generally disclosed, including methods of using such compounds to make various polymers, including, but not limited to, polyesters, polyamides, and polycarbamates. In certain embodiments, the carboxylic acids, carboxylate esters, and carboxylate salts are derived from a renewable source, such as a natural oil.

Abstract: Low-color ester compositions and methods of making low-color ester compositions are generally disclosed. In certain embodiments, methods of making low-color ester compositions from a biorefinery bottoms stream are disclosed. In some other embodiments, methods for recovering esters of 1,18-octadecanedioic acid are disclosed.

Abstract: Polyester polyols are generally disclosed, including methods of making and using them. In some embodiments, the polyester polyols are incorporated into a block copolymer, such as a polyurethane block copolymer. In some embodiments, at least a portion of the polyurethane block copolymer is derived from a renewable source.

Abstract: A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent selected from the group consisting of phosphorous acid, phosphinic acid, and a combination thereof; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product. Methods for suppressing isomerization of olefin metathesis products produced in a metathesis reaction, and methods of producing fuel compositions are described.

Abstract: 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.

Abstract: A method is disclosed for making an unsaturated glycitan ester by reacting intramolecular condensates of glycitols having four or more carbons with a metathesis-derived unsaturated fatty acid in the presence of an alkaline catalyst and under conditions sufficient to form the aforesaid unsaturated glycitan fatty ester. A composition is also disclosed comprising a compound of the following structure: wherein R1 is hydrogen, alkyl, aryl or (CH2)1-9—COOR5; wherein R5 is wherein R2, R3 and R4 are hydrogen, or —(O)C—(CH2)m—CH?CH—R1 or —(CH2CH2O)nH or mixtures thereof; wherein m is 1 to 9; and wherein n is 1 to 100.

Abstract: A method for suppressing isomerization of an olefin metathesis product produced in a metathesis reaction includes adding an isomerization suppression agent that includes nitric acid to a mixture that includes the olefin metathesis product and residual metathesis catalyst from the metathesis reaction under conditions that are sufficient to passivate at least a portion of the residual metathesis catalyst. Methods of refining a natural oil are described.

Abstract: A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent that comprises nitric acid; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product. Methods for suppressing isomerization of olefin metathesis products produced in a metathesis reaction, and methods of producing fuel compositions are described.

Abstract: Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

Abstract: Unsaturated alcohol compositions are obtained by reducing a metathesis-derived hydrocarbyl unsaturated ester. Also disclosed is a process for preparing an unsaturated alcohol composition, where a metathesis derived hydrocarbyl carbonyl compound is reacted in the presence of a silane compound, an organic solvent, and a catalyst system prepared from a metallic complex and a reducing agent. This mixture is then hydrolyzed with a metallic base, and then mixed with organic solvent. The resultant mixture is then separated, washed, dried, and/or purified to produce the unsaturated alcohol composition. The unsaturated alcohol derivatives are useful in many end-use applications, including, for example, lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, plasticizers, asphalt additives, friction reducing agents, plastics, and adhesives.

Abstract: High-purity dibasic acid compositions are generally disclosed. In some embodiments, the dibasic acid compositions are solutions or suspensions. In some other embodiments, the compositions are solid-state compositions. In some such embodiments, the solid-state compositions comprise a dibasic acid as a crystalline solid and further comprise a low quantity of certain impurities, such as monobasic acids, various esters, and the like. Methods and systems for making such high-purity dibasic acid compositions are also disclosed.

Abstract: Systems and methods are disclosed for refining natural oil feedstocks. In some embodiments, the methods comprise transesterifying glycerides in a natural oil feedstock to provide a transesterified product comprising monounsaturated fatty acid esters and polyunsaturated fatty acid esters. In some embodiments, the methods comprise separating the polyunsaturated fatty acid esters from the monounsaturated fatty acid esters (or vice versa), to provide a separated monounsaturated fatty acid ester composition having a ratio of at least 10 parts by weight of monounsaturated fatty acid esters for every 1 part by weight of polyunsaturated fatty acid esters.

Abstract: A method for suppressing isomerization of an olefin metathesis product produced in a metathesis reaction includes adding an isomerization suppression agent to a mixture that includes the olefin metathesis product and residual metathesis catalyst from the metathesis reaction under conditions that are sufficient to passivate at least a portion of the residual metathesis catalyst. The isomerization suppression agent is phosphorous acid, a phosphorous acid ester, phosphinic acid, a phosphinic acid ester or combinations thereof. Methods of refining natural oils are described.

Abstract: Metallic soap compositions for use in various applications, including as adhesives, as having anti-corrosion properties on certain surfaces or materials, and as asphalt modifiers to reduce viscosity in an asphalt mixture, and process for making the same, are disclosed. The processes comprise at least a partial saponification of a mixture of an oil, often a natural oil which may be hydrogenated and/or metathesized, and a metal compound via a fusion process, or may comprise at least a partial saponification of a mixture of a similar oil and a metal compound, or optionally a fatty acid derived from a similar oil, via an aqueous process, with an optional addition of an inorganic metal salt via at least one ion exchange reaction.