Improved processes for making glyceride oligomers are generally disclosed herein. In some embodiments, the disclosed processes provide improved methods of using olefin metathesis to oligomerize unsaturated glycerides to make novel branched-chain polyester compositions. In some aspects, the disclosure also provides compositions formed by such processes.
C11C 3/02 - Fats, oils or fatty acids obtained by chemical modification of fats, oils or fatty acids, e.g. by ozonolysis by esterification of fatty acids with glycerol
C11C 1/00 - Preparation of fatty acids from fats, fatty oils, or waxesRefining the fatty acids
C08G 63/06 - Polyesters derived from hydroxy carboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxy carboxylic acids
2.
FUNCTIONALIZED SILICONE POLYMERS AND METHODS OF MAKING AND USING THE SAME
Functionalized silicone polymers incorporating segments formed from medium-chain fatty acids are generally disclosed herein. Methods of using such compounds, for example, as surfactants, are also disclosed herein, as well as methods of making such compounds, for example, from medium-chain fatty acids derived from natural oils.
C08G 77/14 - Polysiloxanes containing silicon bound to oxygen-containing groups
C08G 77/20 - Polysiloxanes containing silicon bound to unsaturated aliphatic groups
C08G 77/26 - Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen nitrogen-containing groups
C08G 77/24 - Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen halogen-containing groups
3.
SEGMENTED SILICONE POLYMERS AND METHODS OF MAKING AND USING THE SAME
Segmented silicone polymers incorporating segments formed from medium-chain fatty acids are generally disclosed herein. Methods of using such compounds, for example, as surfactants, are also disclosed herein, as well as methods of making such compounds, for example, from medium-chain fatty acids derived from natural oils.
Silane compounds derived from medium-chain fatty acids are generally disclosed herein. Methods of using such compounds, for example, as compatibilizing agents, are also disclosed herein, as well as methods of making such compounds, for example, from medium-chain fatty acids derived from natural oils.
C07F 7/18 - Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
C09D 4/00 - Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond
Alkoxylated fatty acids are disclosed herein, as well as methods of making and using such compounds. In some embodiments, the alkoxylated fatty acids are formed from monomers derived from natural oils. In some embodiments, the alkoxylated fatty acids are used as surfactants for making synthetic latex by emulsion polymerization. In some other embodiments, the alkoxylated fatty acids are used as surfactants for making synthetic rubber, such as styrene-butadiene rubber. In some other embodiments, the alkoxylated fatty acids are used as surfactants in a composition for treatment of gas or oil wells, for cleaning applications, for use in various laundry-related applications, for use in personal care compositions, or for use as solvents for coating applications, such as reactive and non-reactive waterborne coating applications.
Compositions for stimulating hydrocarbon production from a subterranean formation are generally disclosed. In some embodiments, such compositions include olefinic ester compounds, such as alkyl esters of C10-18 unsaturated fatty acids. In some embodiments, the olefinic ester compounds are derived from a natural oil or a natural oil derivative, for example, by catalytic olefin metathesis. Uses of such compounds, such as in oil- and gas-production methods are also generally disclosed.
C09K 8/58 - Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
C09K 8/52 - Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
C10G 1/04 - Production of liquid hydrocarbon mixtures from oil shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction
E21B 43/22 - Use of chemicals or bacterial activity
E21B 43/26 - Methods for stimulating production by forming crevices or fractures
7.
RENEWABLY DERIVED POLYAMIDES AND METHODS OF MAKING THE SAME
Methods of making polyamides from renewable materials, such as natural oils, are generally disclosed herein. In some embodiments, the polyamides are nylon-10. In some such embodiments, nylon-10 is made by polymerizing 10-aminodecanoic acid, or esters thereof. In some further such embodiments, the 10-aminodecanoic acid monomers (or esters thereof) are derived from natural oils via the metathesis of unsaturated fatty acid moieties of the natural oil.
C07C 227/06 - Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
C07C 227/18 - Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
C07C 229/08 - Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
8.
HIGH-WEIGHT GLYCERIDE OLIGOMERS AND METHODS OF MAKING THE SAME
Oligomers of certain glyceride compounds are generally disclosed herein. In some embodiments, the glyceride compounds include natural oil glycerides, such as glycerides derived from natural oils, such as palm oil, soybean oil, canola oil, and the like. Compositions containing such glyceride oligomers are also disclosed herein. Processes for making such glyceride oligomers are also disclosed herein. In some embodiments, the processes for making such compounds include reacting a plurality of unsaturated glyceride compounds in the presence of a metathesis catalyst.
Polyester compositions are disclosed herein, as well as methods of making and using such polyesters. In some embodiments, the polyesters are formed from monomers derived from natural oils. In some embodiments, the polyesters have lower glass transition temperatures than polyesters of comparable molecular weight.
C08G 63/06 - Polyesters derived from hydroxy carboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxy carboxylic acids
Polyester compositions are disclosed herein, as well as methods of making and using such polyesters. In some embodiments, the polyesters are formed from monomers derived from natural oils. In some embodiments, the polyesters are highly branched polymers, such as highly branched polymers that have low viscosity at higher molecular weights.
C08G 63/06 - Polyesters derived from hydroxy carboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxy carboxylic acids
A61K 47/50 - Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additivesTargeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
C08L 67/02 - Polyesters derived from dicarboxylic acids and dihydroxy compounds
11.
RENEWABLY DERIVED POLYESTERS AND METHODS OF MAKING AND USING THE SAME
Polyester compositions are disclosed herein, as well as methods of making and using such polyesters. In some embodiments, the polyesters are formed from monomers derived from natural oils.
C08G 63/664 - Polyesters containing oxygen in the form of ether groups derived from hydroxycarboxylic acids
C08G 63/06 - Polyesters derived from hydroxy carboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxy carboxylic acids
C08G 63/91 - Polymers modified by chemical after-treatment
Alkoxylated fatty acids are disclosed herein, as well as methods of making and using such compounds. In some embodiments, the alkoxylated fatty acids are formed from monomers derived from natural oils. In some embodiments, the alkoxylated fatty acids are used as surfactants for making synthetic latex by emulsion polymerization. In some other embodiments, the alkoxylated fatty acids are used as surfactants for making synthetic rubber, such as styrene-butadiene rubber. In some other embodiments, the alkoxylated fatty acids are used as surfactants in a composition for treatment of gas or oil wells, for cleaning applications, for use in various laundry-related applications, for use in personal care compositions, or for use as solvents for coating applications, such as reactive and non-reactive waterborne coating applications.
Polyurethane compositions are disclosed herein, as well as methods of making and using such polyesters. In some embodiments, the polyurethanes are formed from monomers derived from natural oils. In some embodiments, the polyurethanes are formed without the use of monomers bearing isocyanate groups.
C08G 63/06 - Polyesters derived from hydroxy carboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxy carboxylic acids
C08G 65/00 - Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
C09D 167/02 - Polyesters derived from dicarboxylic acids and dihydroxy compounds
C09D 171/00 - Coating compositions based on polyethers obtained by reactions forming an ether link in the main chainCoating compositions based on derivatives of such polymers
14.
NATURAL OIL-DERIVED WELLBORE COMPOSITIONS AND METHODS OF USE
Compositions useful as wellbore fluids are generally disclosed. In some embodiments, the compositions include polymerizable olefinic surfactant compositions, which, under certain conditions, can polymerize via free-radical polymerization to form surfactant polymers. In some embodiments, the compositions are introduced to an oil well as part of the drilling or extraction process, e.g., to assist in flushing hydrocarbon material out of subterranean formations.
Compounds that stabilize ultraviolet (UV) light are generally disclosed herein. Methods of making and using such compounds are also generally disclosed. Compositions, such as sunscreen compositions, containing such UV-stabilizing compounds are also generally disclosed herein. In some embodiments, UV-stabilizing compounds disclosed herein are derived from a natural oil, such as by metathesis.
Compositions including olefinic compounds are generally disclosed. In some embodiments, such compositions are cleaning compositions, and can be used to clean various surfaces and/or materials. In some embodiments, the olefinic compounds are derived from a natural oil or a natural oil derivative, for example, by catalytic olefin metathesis.
Aliphatic materials and their use in passive heating and cooling applications are generally disclosed. In some embodiments, dibasic acids and esters (diesters) thereof and their use in passive heating and cooling applications are disclosed. In some embodiments, C18 dibasic acids and esters thereof are disclosed, including their use in passive heating and cooling applications. In some embodiments, various olefins, including alkenes and olefinic acids and esters, are disclosed, including their use in passive heating and cooling applications.
Polyol esters of metathesized fatty acids are generally disclosed herein. Methods of using such compounds, for example, as cleaning agents, solvents, and coalescents for paints and coatings, are also disclosed.
Methods of making branched isoparaffin compositions derived from natural oil based linear internal olefins are disclosed. Uses of branched isoparaffins formed by such methods are also disclosed.
Methods of making azelaic acid, or derivatives thereof, from unsaturated monobasic acids or esters are disclosed herein. In some embodiments, the unsaturated monobasic acids or esters are C10-17 unsaturated monobasic acids or esters.
C07C 67/05 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
C07C 67/08 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Methods of carrying out metathesis reactions of natural oil-derived polyenes (e.g., dienes and trienes), including functionalized polyenes, are generally disclosed herein. In some embodiments, the dienes or trienes contain a terminal carbon-carbon double bond, and the metathesis reaction is selective toward reaction of the terminal carbon-carbon double bonds in the polyene. Compounds made by such methods are also generally disclosed herein.
Compositions including certain olefinic ester compounds are generally disclosed. In some embodiments, such compositions are compositions having low toxicity, such as low aquatic toxicity. Therefore, in some embodiments, such compositions can be suitable used as solvents or as part of a solvent system for applications where low toxicity is desirable. Such uses include, but are not limited to, cleaning applications on or near waterways, use in oil or gas recovery, and the like. In some other embodiments, such compositions are treatment fluids for oil wells, and can therefore be introduced into an oil well to remove buildup and other deposits. In some embodiments, the olefinic ester compounds are derived from a natural oil or a natural oil derivative.
C07C 69/347 - Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom esterified with unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
C07C 69/52 - Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
C09K 8/54 - Compositions for in situ inhibition of corrosion in boreholes or wells
23.
POLYESTER POLYOLS AND USE THEREOF IN POWDER COATINGS
Powder coating compositions containing polyester polyols are generally disclosed, including methods of making and using them. In some embodiments, powder coating compositions are disclosed that include a polyester polyol and a cross-linking agent.
This invention related 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 of making the same.
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.
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.
C08J 3/03 - Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
C08L 67/00 - Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chainCompositions of derivatives of such polymers
C08L 77/00 - Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chainCompositions of derivatives of such polymers
27.
LOW-COLOR ESTER COMPOSITIONS AND METHODS OF MAKING AND USING THE SAME
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.
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.
Dibasic esters (diesters) and their use in plasticizer compositions are generally disclosed. In some embodiments, the diesters are branched-chain esters of long-chain alkanedioic acids, such as octadecanedioic acid. In some embodiments, such plasticizer compositions are used to increase the plasticity of a polymer resin, such as a vinyl chloride resin or poly vinyl butyral. In some other embodiments, such plasticizer compositions are used to lower the glass transition temperature of a polymer resin. In some embodiments, at least a portion of the plasticizer is derived from a renewable source, such as a natural oil.
This application relates to branched diester compositions that can be used as a base stock for lubricant applications, or as a base stock blend component for use in a finished lubricant or for particular applications, and methods for making the same.
C10M 105/42 - Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
Methods for making specialty chemical products and chemical intermediates using hydroformylation are generally disclosed. Further, compositions and compounds formed using such methods are also disclosed. In some embodiments, methods are disclosed for refining a renewably sourced material, such as a natural oil, to form compositions, which can be further reacted employing the methods disclosed herein to form certain specialty chemical products or chemical intermediates.
C07C 45/50 - Preparation of compounds having C=O groups bound only to carbon or hydrogen atomsPreparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
Compositions having low quantities of volatile organic compounds (VOCs) and uses thereof are generally disclosed. In some embodiments, the compositions are aqueous compositions, such as aqueous suspensions, suitable for use as coating or paint compositions. In some embodiments, the compositions are aqueous compositions that include, among other components, a film-forming polymer and a coalescing aid. In some embodiments, the coalescing aids are derived from a renewable feedstock. Methods and systems for making such compositions are also disclosed. Novel coalescing aids are also disclosed.
Branched-chain esters and methods of making branched-chain esters are generally disclosed. Various uses of such compounds are also disclosed, including uses in personal care compositions and lubricant compositions. In some embodiments, the branched-chain esters are at least partially derived from a renewable source, such as a natural oil.
Methods and systems for treating an aqueous effluent from a metathesis reactor, such as a metathesis-based biorefinery, are generally disclosed. In some embodiments, the aqueous effluent is generated from washing the metathesized product with an aqueous medium. In some embodiments, such wash streams are chemically treated to reduce their toxicity and to facilitate disposal. In some embodiments, such wash streams are treated to recover at least a portion of the catalyst residue, so as to facilitate catalyst recovery.
Compositions for treating high-molecular-weight components of a petroleum fluid are generally disclosed. In some embodiments, such compositions include olefinic ester compounds, such as alkyl esters of C10-18 unsaturated fatty acids. In some embodiments, such compositions are added to a petroleum fluid to improve the rheological properties, e.g., breaking up or inhibiting the precipitation of high-molecular-weight components of petroleum fluids. In some other embodiments, such compositions are used for removing deposits of such high-molecular-weight components from the surfaces of equipment used for extracting or transporting petroleum or natural gas.
A grease composition is disclosed, having from 50 to 99 weight percent of a lubricating base oil, from 1 to 30 weight percent of a thickener component including one or more of (i) one or more natural oil derivatives selected from the group consisting of triglycerides, diglycerides, monoglycerides, or oligomers therefrom, fatty acid methyl esters and corresponding fatty acids, salts, and dibasic esters therefrom, and C10-C15 esters, C15-C18 esters, or C18+ esters, or diesters therefrom, (ii) one or more carboxylic acids and/or derivatives thereof, and (iii) one or more of a metal base compound, and from 1 to 15 weight percent of one or more optional additives. Processes for making grease compositions are also disclosed.
C10M 117/00 - Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof
C10M 117/06 - Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having more than one carboxyl group bound to an acyclic carbon atom or cycloaliphatic carbon atom
C10N 50/10 - Form in which the lubricant is applied to the material being lubricated semi-solidForm in which the lubricant is applied to the material being lubricated greasy
Compositions including olefinic ester compounds are generally disclosed. In some embodiments, such compositions are cleaning compositions, and can be used to clean various surfaces (e.g., hard surfaces, etc.) and/or materials (e.g., textiles, fibers, etc.). In some embodiments, the olefinic ester compounds are derived from a natural oil or a natural oil derivative, for example, by catalytic olefin metathesis.
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, the polyurethane block copolymers can be used as compatibilizing agents, which can be used, for example, in polymer blends, polymer alloys, solutions, emulsions, as well as in extruded and injection molded articles. In some embodiments, at least a portion of the polyurethane block copolymer is derived from a renewable source.
B32B 27/08 - Layered products essentially comprising synthetic resin as the main or only constituent of a layer next to another layer of a specific substance of synthetic resin of a different kind
39.
HIGH PURITY DIBASIC ACID COMPOSITIONS AND METHODS OF MAKING THE SAME
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 include a dibasic acid as a crystalline solid and further include 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.
C07C 67/303 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
C07C 67/475 - Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
C07C 69/34 - Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
C07C 69/593 - Dicarboxylic acid esters having only one carbon-to-carbon double bond
40.
POLYESTERS CONTAINING METATHESIZED NATURAL OIL DERIVATIVES AND METHODS OF MAKING
A polymeric composition includes the reaction product of monomers, where the monomers include a first monomer having at least two carboxylate functional groups, and a second monomer having at least two hydroxy! functional groups. The second monomer is a reaction product of a metathesized natural oil and a bis(hydroxyalkyl) amine.
Natural oil based fatty acid wax compositions and their methods of making are provided. The methods comprise providing a natural oil, and hydrogenating and metathesizing the natural oil, and then converting the hydrogenated metathesized natural oil to obtain a fatty acid wax comprising free fatty acids and/or salts of fatty acids, glycerol and/or alcohol, and paraffin, wherein the fatty acid wax has at least 50 wt% of carbon chain compositions with at least 18 carbon atoms. The compositions may comprise 85-100 wt% long-chain fatty acids, 0-15 wt% esters, wherein the fatty acid comprises between 15-60 wt% long chain di-acids and 40-85 wt% long chain mono-acids. The compositions may comprise about 50-100 wt% long-chain fatty acids and about 0-50 wt% esters, wherein the fatty acid may comprise between about 15-80 wt% long chain di-acids and about 20-85 wt% long chain monoacids.
This disclosed invention relates to a maleinated ester derivative derived from an unsaturated linear aliphatic carboxylic acid methyl ester, maleic anhydride, and a monohydric alcohol. Lubricants and functional fluids containing the maleinated esters are disclosed.
C10M 169/04 - Mixtures of base-materials and additives
C10M 129/78 - Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic acids
43.
NATURAL OIL DERIVATIVES INCLUDING PRIMARY AMINE FUNCTIONAL GROUPS
A compound represented by Structure 1, which may be used to form a dendritic molecule. Preferably the compound is derived from a natural oil. More preferably the compound is derived from a metathesized natural oil. The compound represented by Structure I, also may be used in a polymerization reaction where R1 and R2 independently are C2 - C12 alkyl groups, X1 is a C4 - C28 alkyl or alkenyl group, and R3 is selected from the group consisting of H and a bis (aminoalkyl) amide group having Structure II where R4 and R5 independently are C2 - C12 alkyl groups.
C07C 231/02 - Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
44.
NATURAL OIL DERIVATIVES INCLUDING (METH)ACRYLATE FUNCTIONAL GROUPS
A compound having a plurality of (meth)acrylate functional groups may be a ((meth)acryloylalkyl)amide. Preferably the compound having a plurality of (meth)acrylate functional groups is derived from a natural oil. More preferably the compound having a plurality of (meth)acrylate functional groups is derived from a metathesized natural oil. A compound having a plurality of (meth)acrylate functional groups may be used in a polymerization reaction. Monomers having a plurality of (meth)acrylate functional groups may be used as chain extenders, as crosslinkers, or as branching points in a polymer. A compound having a plurality of (meth)acrylate functional groups, such as the reaction product of a metathesized natural oil and a bis(aminoalkyl) amine and/or a compound represented by Structure I above, also may be used to form a dendritic molecule.
C07C 233/18 - Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
C07C 233/20 - Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
C11C 3/00 - Fats, oils or fatty acids obtained by chemical modification of fats, oils or fatty acids, e.g. by ozonolysis
45.
DIENE-SELECTIVE HYDROGENATION OF METATHESIS-DERIVED OLEFINS AND UNSATURATED ESTERS
Methods are provided for refining natural oil feedstocks and partially hydrogenating polyunsaturated olefins and polyunsaturated esters. The methods comprise reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters. In certain embodiments, the methods further comprise separating the polyunsaturated olefins from the polyunsaturated esters in the metathesized product. In certain embodiments, the methods further comprise partially hydrogenating the polyunsaturated olefins in the presence of a hydrogenation catalyst, wherein at least a portion of the polyunsaturated olefins are converted to monounsaturated olefins. In other embodiments, the methods further comprise partially hydrogenating the polyunsaturated esters in the presence of a hydrogenation catalyst, wherein at least a portion of the polyunsaturated esters are converted to monounsaturated esters.
An alkenyl glycoside is prepared by reacting a metathesis-derived unsaturated fatty alcohol containing 10 to 30 carbon atoms with either (1 ) a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide, or (2) a hydrocarbyl glycoside produced by reacting an alcohol containing up to 6 carbon atoms with a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide. Each of these reactions is performed in the presence of an acid catalyst and under conditions sufficient to form the alkenyl glycoside or hydrocarbyl glycoside. The preferred alkenyl glycosides are 9-decen-1 -yl glycoside; 9-dodecen-1 -yl glycoside; 9-tridecen-1 -yl glycoside; 9-pentadecen-1 -yl glycoside; 9- octadecen-yl glycoside; or 9-octadecen-1,18-diyl glycoside.
C07H 15/10 - Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of a saccharide radical containing unsaturated carbon-to-carbon bonds
C07H 1/00 - Processes for the preparation of sugar derivatives
47.
GLYCITAN ESTERS OF UNSATURATED FATTY ACIDS AND THEIR PREPARATION
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 including a compound of the following structure: wherein R1 is hydrogen, alkyl, aryl or (CH2)i.g-COOR5; wherein R5 is wherein R2, R3 and R4 are hydrogen, or -(0)C-(CH2)m-CH=CH-R1 or - (CH2CH20)nH or mixtures thereof; wherein m is 1 to 9; and wherein n is 1 to 100.
A lubricant composition may include a copolymer having constitutional units formed from monomers including an alpha-olefin and an α-ester-alk-ω-ene molecule, where the composition has a kinematic viscosity at 100 °C of at most 20 centistokes, or of at least 40 centistokes. A lubricant composition may include a copolymer having constitutional units formed from monomers including an alpha-olefin, an α-ester-alk-ω-ene molecule and an cc- (carboxylic acid)-alk-ω-ene molecule, where the composition has a viscosity that varies as the molar ratio of the α-ester-alk-ω-ene molecule α-(carboxylic acid)-alk-ω-ene molecule in the monomers varies.
Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is 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 transestehfying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.
C07C 67/333 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton
C07C 67/475 - Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
C07C 51/353 - Preparation of carboxylic acids or their salts, halides, or anhydrides by reactions not involving formation of carboxyl groups by isomerisationPreparation of carboxylic acids or their salts, halides, or anhydrides by reactions not involving formation of carboxyl groups by change of size of the carbon skeleton
A method for treating a substrate prior to a metathesis reaction includes treating the substrate with a first agent configured to mitigate potentially adverse effects of one or more contaminants in the substrate on a catalyst used to catalyze the metathesis reaction. The treating reduces a level of the one or more contaminants by an amount sufficient to enable the metathesis reaction to proceed at a substrate-to-catalyst molar ratio of at least about 7,500 to 1. Methods for metathesizing substrates are described.
Copolymers of alpha-olefins are generally disclosed, including methods of making such copolymers. In some embodiments, copolymers of alpha-olefins and certain unsaturated ester compounds are also disclosed, including methods of making such copolymers. Lubricant compositions including copolymers of alpha-olefins are also disclosed, as well as methods of using such compositions in certain lubricant applications.
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.
C07C 67/347 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
C07C 69/593 - Dicarboxylic acid esters having only one carbon-to-carbon double bond
C07C 69/602 - Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
C07C 69/604 - Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups
C07C 69/608 - Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
C07C 51/353 - Preparation of carboxylic acids or their salts, halides, or anhydrides by reactions not involving formation of carboxyl groups by isomerisationPreparation of carboxylic acids or their salts, halides, or anhydrides by reactions not involving formation of carboxyl groups by change of size of the carbon skeleton
Various methods are provided for treating and reacting a metathesis feedstock. In one embodiment, the method includes providing a feedstock comprising a natural oil, chemically treating the feedstock with a metal alkoxide 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.
A grease composition is disclosed, having from 50 to 99 weight percent of a lubricating base oil, from 1 to 30 weight percent of a thickener component including one or more of (i) one or more natural oil derivatives, (ii) one or more hydrogenated metathesized natural oils and/or natural oil derivatives, (iii) one or more amidated metathesized natural oils and/or natural oil derivatives, (iv) one or more, or two or more, carboxylic acids and/or derivatives thereof, and (v) one or more of a metal base compound, and from 1 to 15 weight percent of one or more optional additives. Processes for making grease compositions are also disclosed.
C10M 169/02 - Mixtures of base-materials and thickeners
C10M 177/00 - Special methods of preparation of lubricating compositionsChemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
55.
WAX COMPOSITIONS AND THE EFFECT OF METALS ON BURN RATES
A wax composition is disclosed, comprising a hydrogenated natural oil with (i) at least about 50 wt% of a triacylglycerol component having a fatty acid composition from about 14 to about 25 wt% C16:0 fatty acid, about 45 to about 60 wt% C18:1 fatty acid and about 20 to about 30 wt% C18:0 fatty acid, (ii) a nickel content of less than 1 ppm, and (iii) a melt point of about 49 °C to about 57 °C. The hydrogenated natural oil is filtered and/or bleached to obtain a nickel content of less than 0.5ppm. A candle is also disclosed, comprising a wick and the above described wax.
Methods of preparing ruthenium carbene complex precursors are disclosed herein. In some embodiments, the methods include reacting a ruthenium refinery salt with an L-type ligand and a reducing agent to form the ruthenium carbene complex precursor. Methods of preparing a ruthenium vinylcarbene complex are also disclosed. In some embodiments, preparing a ruthenium carbene complex includes converting a ruthenium carbene complex precursor into a ruthenium carbene complex having a structure (PR1R2R3)2CI2Ru=CH-R4, wherein R1, R2, R3, and R4 are defined herein.
A method of isomerizing a substance includes combining a substance including a terminal alkenyl group and a substance including a fluorosulfonic acid group in a reaction mixture, and forming a substance including a 2-alkenyl group from the substance including a terminal alkenyl group in the reaction mixture. The method may be used to functionalize a substance, as the substance including a 2-alkenyl group can be reacted with a functionalizing agent to form a substance including a first functional group. The methods may be used to form a dicarboxylic acid, such as suberic acid, from a renewable feedstock.
C07C 67/333 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton
C07C 67/475 - Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
C07C 5/25 - Migration of carbon-to-carbon double bonds
C07C 51/09 - Preparation of carboxylic acids or their salts, halides, or anhydrides from carboxylic acid esters or lactones
C07C 51/285 - Preparation of carboxylic acids or their salts, halides, or anhydrides by oxidation with peroxy-compounds
58.
METHODS OF REFINING AND PRODUCING DIBASIC ESTERS AND ACIDS FROM NATURAL OIL FEEDSTOCKS
Methods and systems for making dibasic esters and/or dibasic acids using metathesis are generally disclosed. In some embodiments, the methods comprise reacting a terminal olefin ester with an internal olefin ester in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In some embodiments, the terminal olefin ester or the internal olefin ester are derived from a renewable feedstock, such as a natural oil feedstock. In some such embodiments, the natural oil feedstock, or a transesterified derivative thereof, is metathesized to make the terminal olefin ester or the internal olefin ester.
C07C 67/475 - Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
C07C 67/303 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
Methods and compositions are provided for refining natural oils and for producing high-weight esters, high-weight acids, and/or high-weight derivatives thereof, wherein the compositions are made by cross-metathesizing low-weight unsaturated esters or low-weight unsaturated acids having hydrocarbon chain lengths less than or equal to C24 with an olefin feedstock, thereby forming a metathesized product composition comprising high-weight esters or high-weight acids having hydrocarbon chain lengths greater than C18, wherein at least a portion of the hydrocarbon chain lengths in the metathesized product are larger than the hydrocarbon chain lengths in the starting feedstock. In certain embodiments, the low-weight unsaturated esters or low-weight unsaturated acids are derived by reacting a natural oil feedstock in a metathesis reactor in the presence of a metathesis catalyst to form a metathesized product composition comprising olefins and low-weight unsaturated esters, and then separating the olefins from the low-weight unsaturated esters. In some embodiments, the low-weight unsaturated ester compositions may be hydrolyzed to form the low-weight unsaturated acid compositions.
C10G 45/00 - Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
C07C 67/333 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton
C07C 67/343 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton by increase in the number of carbon atoms
C07C 69/533 - Monocarboxylic acid esters having only one carbon-to-carbon double bond
C10G 3/00 - Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
Polymers containing natural oil derivatives are generally disclosed. Methods of forming such polymers are also generally disclosed. In some embodiments, the polymer is a polyurethane. In some embodiments, the natural oil derivative is a cross-linking group that links two or more polymer chains together.
C07C 229/02 - Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
A metathesized natural oil composition comprising (i) a mixture olefins and/or esters, or (ii) a metathesized natural oil, is disclosed. The metathesized natural oil composition has a number average molecular weight in the range from about 100 g/mol to about 150,000 g/mol, a weight average molecular weight in the range from about 1,000 g/mol to about 100,000 g/mol, a z-average molecular weight in the range from about 5,000 g/mol to about 1,000,000 g/mol, and a polydispersity index of about 1 to about 20. The metathesized natural oil composition is metathesized at least once.
A method for suppressing dehydrogenation includes reacting an optionally functionalized olefin reactant in a metathesis reaction to form an olefin metathesis product; and providing a dehydrogenation suppression agent in admixture with (a) the olefin metathesis product and/or the optionally functionalized olefin reactant, and (b) a metal-containing material selected from the group consisting of residual metathesis catalyst, a hydrogen transfer agent, and a combination thereof, under conditions that are sufficient to passivate at least a portion of the metal-containing material. Methods of refining natural oils and methods of producing fuel compositions are also described.
C10G 45/00 - Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
C11C 3/00 - Fats, oils or fatty acids obtained by chemical modification of fats, oils or fatty acids, e.g. by ozonolysis
C10G 3/00 - Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
C07C 6/04 - Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
C07C 67/333 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton
C07C 7/20 - Use of additives, e.g. for stabilisation
A method for suppressing dehydrogenation includes reacting an optionally functionalized olefin reactant in a metathesis reaction to form an olefin metathesis product; and providing a dehydrogenation suppression agent in admixture with (a) the olefin metathesis product and/or the optionally functionalized olefin reactant, and (b) a metal-containing material selected from the group consisting of residual metathesis catalyst, a hydrogen transfer agent, and a combination thereof, under conditions that are sufficient to passivate at least a portion of the metal-containing material. Methods of refining natural oils and methods of producing fuel compositions are also described.
Unsaturated alcohol compositions are obtained by reducing a metathesis- derived hydrocarby! unsaturated ester. Also disclosed is a process for preparing an unsaturated alcohol composition, where a metathesis derived hydrocarby! 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.
C07C 29/147 - Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen-containing functional group of C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
C07C 33/025 - Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
65.
Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
This invention 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 a selected olefin metathesis catalyst. In one embodiment of the invention, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting an olefinic substrate comprised of at least one internal olefin with ethylene, in the presence of a metathesis catalyst, wherein the catalyst is present in an amount that is less than about 1000 ppm relative to the olefinic substrate, and wherein the metathesis catalyst has the structure of formula (II)
wherein the various substituents are as defined herein. The invention has utility, for example, in the fields of catalysis, organic synthesis, and industrial chemistry.
C07C 6/04 - Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
C07C 67/333 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton
This invention relates to terpene derived compounds and farnesene derived compounds, and to the use of such terpene derived compounds and farnesene derived compounds in lubricants, detergents, dispersants, functional fluids, fuels, polymer compositions,cold flow improvers, and the like.
C10M 145/12 - Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
C10L 1/196 - Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof
67.
METHODS FOR SUPPRESSING ISOMERIZATION OF OLEFIN METATHESIS PRODUCTS, METHODS OF REFINING NATURAL OILS, AND METHODS OF PRODUCING FUEL COMPOSITIONS
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 and methods of producing fuel compositions are described.
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 and methods of producing fuel compositions are described.
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 includes (i) a salt and/or an ester of a phosphorous oxo acid, and/or (ii) a derivative of the phosphorous oxo acid in which at least one P-H bond has been replaced by a P-C bond, and/or (iii) a salt and/or an ester of the derivative. Methods of refining natural oils and methods of producing fuel compositions are described.
A method for preparing a ruthenium carbene complex precursor includes reacting a ruthenium refinery salt with a hydrogen halide to form a ruthenium intermediate, and reacting the ruthenium intermediate with an L-type ligand to form the ruthenium carbene complex precursor. A method for preparing a ruthenium vinylcarbene complex includes converting a ruthenium carbene complex precursor into a ruthenium hydrido halide complex, and reacting the ruthenium hydrido halide complex with a propargyl halide to form the ruthenium carbene complex. A method for preparing a ruthenium carbene complex includes converting a ruthenium carbene complex precursor into a ruthenium carbene complex having a structure (PR1 R2R3)2CI2Ru=CH-R4, wherein R1, R2, R3, and R4 are alike or different, and wherein covalent bonds may optionally exist between two or more of R1, R2, and R3 and/or two of R1, R2, and R3 taken together may optionally form a ring with phosphorous.
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.
This invention relates to a fuel composition, comprising: (A) a normally liquid fuel; and (B) a cold flow improving amount of (i) a metathesized natural oil; (ii) a metathesized natural oil derivative; or (iii) a mixture of (i) and (ii). The invention also relates to metathesized derivatives formed by the reaction of a metathesized natural oil with a nucleophile, oxidizer, aromatic compound, enophilic acid reagent, or a mixture of two or more thereof.
This invention relates to a composition, comprising: an unsaturated functionalized monomer of from about 5 to about 30 carbon atoms, which is: (a) polymerized to form a functionalized polymer; (b) copolymerized with a comonomer to form a functionalized copolymer; or (c) reacted with an enophilic reagent to form a polyfunctionalized monomer. The polyfunctionalized monomer may be polymerized to form a polyfunctionalized polymer which may be further reacted with one or more additional reagents. The invention relates to lubricants, functional fluids, fuels, dispersants, detergents and polymeric resins.
Lipid-based wax compositions and their methods of making are provided for compositions substantially free of fat bloom. The compositions comprise 0.1 -10 percent by weight triacylglycerides, 30-95 percent by weight monoacylglycerides and diacylglycerides combined, and 0.1 -65 percent by weight fatty acids. The methods comprise blending the monoacylglycerides, diacylglycerides, triacylglycerides, and fatty acids by heating the lipid-based wax composition at a sufficiently high temperature to destroy substantially all crystal structure within the lipid-based wax composition. The methods further comprise pouring the lipid-based wax composition into a mold or a container having a surface and a core, wherein the pouring is conducted at a temperature at least 15°C greater than the congeal point of the lipid- based wax composition. The methods further comprise cooling the lipid-based wax composition under conditions sufficient to cool the core to at least 5°C below the congeal point of the lipid-based wax composition in 30-90 minutes.
This invention 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 a selected olefin metathesis catalyst. In one embodiment of the invention, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting an olefinic substrate comprised of at least one internal olefin with ethylene, in the presence of a metathesis catalyst, wherein the catalyst is present in an amount that is less than about 1000 ppm relative to the olefinic substrate, and wherein the metathesis catalyst has the structure of formula (II)
wherein the various substituents are as defined herein. The invention has utility, for example, in the fields of catalysis, organic synthesis, and industrial chemistry.
Wax compositions derived from metathesized natural oils and amines and methods of making wax compositions from metathesized natural oils and amines are provided. The wax compositions comprise amidated metathesized natural oils formed from a metathesized natural oil and at least one amine. The methods comprise providing an amine and providing a metathesized natural oil. The methods further comprise mixing the amine and the metathesized natural oil in the presence of a basic catalyst or heat, causing a reaction between the amine and metathesized natural oil, therein forming the amidated metathesized natural oil.
C10G 50/02 - Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation of hydrocarbon oils for lubricating purposes
77.
NATURAL OIL BASED MARKING COMPOSITIONS AND THEIR METHODS OF MAKING
Natural oil based marking compositions and their methods of making are provided. The compositions comprise a lipid-based wax having approximately 0-90 percent by weight triacylglycerides and approximately 10-99 percent by weight monoacylglycerides and diacylglycerides combined. The compositions also comprise approximately 1-40 percent by weight of a structuring agent. The methods comprise blending the composition by heating the lipid-based wax and structuring agent at a sufficiently high temperature to destroy substantially all crystal structure within the lipid-based wax. The methods further comprise pouring the composition into a mold having a surface and a core, wherein the pouring is conducted at a temperature at least 5°C greater than the congeal point of the lipid-based wax. The methods further comprise cooling the lipid-based wax under conditions sufficient to cool the core to at least 5°C below the congeal point of the lipid-based wax in approximately 30-90 minutes.
Lipid-based wax compositions and their methods of making are provided for compositions substantially free of fat bloom. The compositions comprise approximately 7-80 percent by weight triacylglycerides and approximately 20-93 percent by weight monoacylglycerides and diacylglycerides combined. The methods comprise blending the monoacylglycerides, diacylglycerides, and triacylglycerides in the lipid-based wax composition by heating the lipid-based wax composition at a sufficiently high temperature to destroy substantially all crystal structure within the lipid-based wax composition. The methods further comprise pouring the lipid-based wax composition into a mold or a container having a surface and a core, wherein the pouring is conducted at a temperature at least 15°C greater than the congeal point of the lipid-based wax composition. The methods further comprise cooling the lipid-based wax composition under conditions sufficient to cool the core to at least 5°C below the congeal point of the lipid-based wax composition in approximately 30-90 minutes.
Methods are provided for refining natural oil feedstocks. The methods comprise reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters. In certain embodiments, the methods further comprise separating the olefins from the esters in the metathesized product. In certain embodiments, the methods further comprise hydrogenating the olefins under conditions sufficient to form a fuel composition. In certain embodiments, the methods further comprise transesterifying the esters in the presence of an alcohol to form a transesterified product.
Methods are provided for producing a jet fuel composition from a feedstock comprising a natural oil. The methods comprise reacting the feedstock with a low-weight olefin in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product. The methods further comprise hydrogenating the metathesized product under conditions sufficient to form a jet fuel composition.
Methods are provided for producing a jet fuel composition from a feedstock comprising a natural oil. The methods comprise reacting the feedstock with oxygen under conditions sufficient to form an oxygen-cleaved product. The methods further comprise hydrogenating the oxygen-cleaved product under conditions sufficient to form a jet fuel composition.
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°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.
A hybrid wax compositions that are suitable for use in manufacturing wax articles (e.g., candles) by compression molding. The combination of a hydrogenated natural oil- based wax and a paraffin wax having a select distribution of hydrocarbon chain lengths provides the hybrid wax compositions with improved properties, such as improved compressive strength and improved de-molding characteristics, for example, as evidenced by reduced scarring and/or flashing. The hybrid wax compositions comprise: (a) a wax comprising a hydrogenated natural oil; and (b) a paraffin wax, wherein the paraffin wax comprises less than about 50% by weight of the hybrid wax composition, and wherein about 52% or greater of hydrocarbons in the paraffin wax have carbon chain lengths ranging from C25 to C29.
A hybrid wax compositions that are suitable for use in manufacturing wax articles (e.g., candles) by compression molding. The combination of a hydrogenated natural oil- based wax and a paraffin wax having a select distribution of hydrocarbon chain lengths provides the hybrid wax compositions with improved properties, such as improved compressive strength and improved de-molding characteristics, for example, as evidenced by reduced scarring and/or flashing. The hybrid wax compositions comprise: (a) a wax comprising a hydrogenated natural oil; and (b) a paraffin wax, wherein the paraffin wax comprises less than about 50% by weight of the hybrid wax composition, and wherein about 52% or greater of hydrocarbons in the paraffin wax have carbon chain lengths ranging from C25 to C29.
A candle and process for making it are disclosed. The candle comprises prilled wax particles, comprising hydrogenated natural oil and wherein at least 75 % of the prilled wax particles less than 800 µm in diameter. The candle includes a compressed core and a thermally fused outer layer.
A candle and process for making it are disclosed. The candle comprises prilled wax particles, comprising hydrogenated natural oil and wherein at least 75 % of the prilled wax particles less than 800 &mgr;m in diameter. The candle includes a compressed core and a thermally fused outer layer.
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.
Antimicrobial compositions comprising a combination of a first antimicrobial agent of Formula I and a second antimicrobial agent of Formula IV are reported. The antimicrobial compositions including a combination of antimicrobial agents of Formula (I) and Formula (IV) are effective as an antimicrobial agent with MIC levels of about 0.1% or less against certain fungi. Also reported are antimicrobial products such as consumer products, industrial preparations, and food and feed formulations.
A01N 37/00 - Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
A01N 43/16 - Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atom with one hetero atom six-membered rings with oxygen as the ring hetero atom
89.
WAX COMPOSITIONS AND METHODS OF PREPARING WAX COMPOSITIONS
Described are morphology stable wax composition comprising the (trans)esterification product of a wax-forming composition comprising: (a) a triglyceride stock, a fatty acid stock, or a mixture thereof; and (b) a glycerol-based composition comprising glycerol, polyglycerol, or a mixture thereof. Methods of making the waxes are also described. The wax compositions may be used in candles, stack waxes, jell candles, cosmetics, food coatings, adhesives, board manufacturing (e.g., particle board and oriented strand board), urethane foams or coatings, alkyd coatings, coating formulation additives, printing additives, polymer processing agents, extrusion processing aids, polymer plasticizers, mold releases, polishes, and stick markers.
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.
The invention is directed to methods of making organic compounds (e.g., organic acid or aldehyde compounds) by metathesis followed by oxidation and either oxidative or reductive cleavage. The methods may be used to make certain industrially important organic acid compounds, for example, azelaic acid. The methods of the invention make use of a cross-metathesis step with a short-chain olefin to chemically modify the starting composition in order to produce a functionalized alkene intermediate that has a pre-determined carbon-carbon double bond position. Upon separation of the functionalized alkene intermediate from the other cross-metathesis products, it is oxidized and then may be oxidatively cleaved to form an organic acid or reductively cleaved to form an aldehyde.
C07C 51/34 - Preparation of carboxylic acids or their salts, halides, or anhydrides by oxidation with ozonePreparation of carboxylic acids or their salts, halides, or anhydrides by hydrolysis of ozonides
C07C 51/353 - Preparation of carboxylic acids or their salts, halides, or anhydrides by reactions not involving formation of carboxyl groups by isomerisationPreparation of carboxylic acids or their salts, halides, or anhydrides by reactions not involving formation of carboxyl groups by change of size of the carbon skeleton
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.
Described is a method of chemically modifying a starting composition comprising polyunsaturated alkene compounds in order to convert at least a portion of the polyunsaturated alkene compounds into functionalized monounsaturated alkene compounds. The separated monounsaturated alkene compounds may be useful, for example, as a starting material in the synthesis of organic chemicals such as diacids, diesters, and the like.
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 °C. The methods, compositions, reactions and reaction systems herein disclosed have utility in the fields of catalysis, organic synthesis, and industrial chemistry.
C08F 4/26 - Metallic compounds other than hydrides and other than metallo-organic compoundsBoron halide or aluminium halide complexes with organic compounds containing oxygen of manganese, iron group metals, or platinum group metals
95.
SYNTHESIS OF TERMINAL ALKENES FROM INTERNAL ALKENES AND ETHYLENE VIA OLEFIN METATHESIS
This invention 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 a selected olefin metathesis catalyst. In one embodiment of the invention, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting an olefinic substrate comprised of at least one internal olefin with ethylene, in the presence of a metathesis catalyst, wherein the catalyst is present in an amount that is less than about 1000 ppm relative to the olefinic substrate, and wherein the metathesis catalyst has the structure of formula (II), wherein the various substituents are as defined herein. The invention has utility, for example, in the fields of catalysis, organic synthesis, and industrial chemistry.
C07C 67/333 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton
C07C 69/587 - Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
C07C 69/58 - Esters of straight chain acids with eighteen carbon atoms in the acid moiety
C07C 69/533 - Monocarboxylic acid esters having only one carbon-to-carbon double bond
96.
HOT MELT ADHESIVE COMPOSITIONS COMPRISING METATHESIZED UNSATURATED POLYOL ESTER WAX
Disclosed are hot melt adhesive compositions comprising a metathesized unsaturated polyol ester wax. Typically, the metathesized unsaturated polyol ester wax is derived from renewable starting materials such as vegetable oils or animal fats. The metathesized unsaturated polyol ester wax typically replaces a portion or all of a petroleum-derived wax or synthetic wax in various hot melt adhesive compositions. The hot melt adhesives may be conventional hot melt adhesives or hot melt pressure-sensitive adhesives.
C09J 191/00 - Adhesives based on oils, fats or waxesAdhesives based on derivatives thereof
C09J 5/04 - Adhesive processes in generalAdhesive processes not provided for elsewhere, e.g. relating to primers involving separate application of adhesive ingredients to the different surfaces to be joined
97.
RING OPENING CROSS-METATHESIS REACTION OF CYCLIC OLEFINS WITH SEED OILS AND THE LIKE
This invention relates generally to olefin metathesis, and more particularly relates to the ring-opening, ring insertion cross-metathesis of cyclic olefins with internal olefins such as seed oils and the like. In one embodiment, a method is provided for carrying out a catalytic ring-opening cross-metathesis reaction, comprising contacting at least one olefinic substrate with at least one cyclic olefin as a cross metathesis partner, in the presence of a ruthenium alkylidene olefin metathesis catalyst under conditions effective to allow ring insertion cross metathesis whereby the cyclic olefin is simultaneously opened and inserted into the olefinic substrate. The invention has utility in the fields of catalysis, organic synthesis, and industrial chemistry.
C07C 67/475 - Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
C07C 69/58 - Esters of straight chain acids with eighteen carbon atoms in the acid moiety
C07C 69/608 - Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
Disclosed are petrolatum-like compositions that comprise metathesized unsaturated polyol esters. Also disclosed are emulsions comprising metathesized unsaturated polyol esters. The petrolatum-like compositions may be used as substitutes for petroleum-based petrolatum. The emulsions may be water-in-oil or oil-in-water emulsions and may be suitable for a variety of end uses.
Disclosed are improved colorant compositions that are suitable for encapsulation in an impact-rupturable casing that is adapted for intact projectile motion and rupture upon contact with a target surface. In many embodiments, the colorant compositions comprise (a) a carrier comprising: (i) a metathesized unsaturated polyol ester; and (ii) a polyol ester; and (b) a colorant. The colorant compositions are useful in paint balls for use in conjunction with projectile devices, such as paint ball markers.
The invention provides methods for treating a surface, the method including steps of applying a surface treatment composition to a surface, wherein the surface treatment composition includes a substantially phenol-free cleansing agent and an antimicrobial agent, the antimicrobial agent comprising 9-decenoic acid, a salt of 9-decenoic acid, an ester of 9-decenoic acid, or a combination thereof, wherein the antimicrobial agent is present in an amount sufficient to control microbial growth. Also described are methods for treating a surface that include the step of applying a surface treatment composition having a pH in the range of 4.1 to 8.5 to a surface, wherein the surface treatment composition includes a cleansing agent and an antimicrobial agent, the antimicrobial agent comprising 9-decenoic acid, a salt of 9-decenoic acid, an ester of 9-decenoic acid, or a combination thereof, wherein the antimicrobial agent is present in an amount sufficient to control microbial growth. Also described are surface treatment compositions including the antimicrobial agents.
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