Abstract: Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfitated. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.

Abstract: Surfactant compositions comprising an alkoxylate, a sulfate, or ether sulfate of a C10-C12 monounsaturated alcohol are disclosed. The alkoxylate, sulfate, or ether sulfate may derive from undecylenic acid or undecylenic alcohol. Compared with their saturated analogs, the monounsaturated alkoxylates, sulfates, and ether sulfates are less irritating, making them valuable for personal care, laundry, cleaners, and other household applications. Microscopy studies show that the alkoxylates, sulfates, and ether sulfates have favorable phase behavior over a wide range of actives levels, expanding opportunities for products with greater compaction. When combined with cationic surfactants, the alkoxylates, sulfates, and ether sulfates exhibit synergy, and they have improved solubility compared with their saturated analogs. The surfactants find value for the personal care, laundry and cleaning, emulsion polymerization, agricultural products, oilfield applications, and specialty foams industries.

Abstract: Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a primary or secondary amine. Derivatives made by reducing, quaternizing, sulfonating, alkoxylating, sulfating, and sulfitating the fatty amide are also included. The amine reactant can be diethylenetriamine or (2-aminoethyl)ethanolamine, which provide imidazoline amides or esters, respectively. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The compositions are valuable for cleaners, fabric treatment, hair conditioning, personal care, antimicrobial compositions, agricultural uses, and oil field applications.

Abstract: Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfated. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.

Abstract: Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfating the esteramines are also disclosed. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The esteramines and derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

Abstract: Alkoxylated fatty ester compositions are disclosed. In one aspect, the compositions comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with one or more alkylene oxides in the presence of an insertion catalyst to give an alkoxylated fatty ester. In another aspect, the metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or its ester derivative is reacted with a glycol ether or a glycol ether alkoxylate, to give an alkoxylated fatty ester. In yet another aspect, the metathesis-derived C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is reacted with one or more alkylene oxides to give a fatty acid alkoxylate, followed by etherification of the fatty acid alkoxylate.

Abstract: Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a primary or secondary amine. Derivatives made by reducing, quaternizing, sulfonating, alkoxylating, sulfating, and sulfitating the fatty amide are also included. The amine reactant can be diethylenetriamine or (2-aminoethyl)ethanolamine, which provide imidazoline amides or esters, respectively. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The compositions are valuable for cleaners, fabric treatment, hair conditioning, personal care, antimicrobial compositions, agricultural uses, and oil field applications.

Abstract: Fatty amine compositions made from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. In another aspect, fatty amidoamines made by reacting a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with an aminoalkyl-substituted tertiary amine are disclosed. The fatty amines or amidoamines are advantageously sulfonated, sulfitated, oxidized, or reduced. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.

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: Aqueous glyphosate formulations comprising a surfactant derived from metathesized natural oil feedstocks are disclosed. The formulations comprise a glyphosate salt, water, and a surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives. The surfactant is selected from C10 or C12 amine oxides, C10 or C12 quats, C10, C12, or C16 amidoamines, C10 or C12 amidoamine oxides, C10 imidazoline quats, C10 or C12 amidoamine quats, C10, C12, or C16 betaines, C16 amidoamine betaines, C18 diamidoamines, C18 diamidoamine oxides, C18 diamidoamine diquats, C18 diamidoamine oxide quats, C18 diamidoamine oxide betaines, Cis diamidoamine monobetaines, C18 diamidoamine monobetaine quats, C18 ester amidoamine quats, and amidoamines and their oxidized or quaternized derivatives made from self- or cross-metathesized palm or soybean oil.

Abstract: Synergistic surfactant blends are disclosed. In one aspect, the blend comprises an anionic surfactant and a metathesis-based cationic surfactant comprising a quaternized derivative. The quaternized derivative is a quaternized fatty amine, quaternized fatty amidoamine, imidazoline quat, or esteramine quat made from a metathesis-derived C10-C17 monounsaturated acid or its ester derivative. Also disclosed are synergistic surfactant blends comprising a cationic surfactant and a metathesisbased anionic surfactant comprising a sulfonated derivative. The sulfonated derivative is a fatty ester sulfonate, fatty acid sulfonate, sulfoestolide, fatty amide sulfonate, sulfonated fatty ester alkoxylate, imidazoline quat sulfonate, sulfonated amidoamine oxide, or sulfonated amidoamine betaine. The synergistic blends have a negative value or a reduced interfacial tension (IFT) when compared with an expected IFT value calculated from the individual surfactant components.

Abstract: Unsaturated fatty alcohol alkoxylates, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol alkoxylate is made by reducing a metathesis-derived monounsaturated alkyl ester, followed by alkoxylation of the resulting monounsaturated alcohol. Microscopy reveals that the monounsaturated alkoxylates have isotropic and lamellar phases over a wider range of actives levels compared with their saturated analogs. This attribute expands formulating latitude for many end-use applications. The unsaturated fatty alcohol alkoxylates are valuable in, for example, agricultural solvents, nonionic emulsifiers for agricultural compositions, hard surface cleaners, laundry detergents, specialty foams, additives or surfactants for paints or coatings, and surfactant compositions for enhanced oil recovery.

Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.

Abstract: Surfactants and solvents containing derivatized adducts formed from Diels-Alder reactions of terpenes and unsaturated carboxylic acids or their derivatives are disclosed. Processes for making and derivatizing the Diels-Alder adducts are also disclosed.

Abstract: Esterquats (reaction products of a fatty acid source and a trialkanolamine) having a desirable distribution of mono-, di-, and tri-quat esters, such as at least 55 wt. % of the diester and at most 25% of the triester, can be produced by heating a trialkanolamine and a fatty acid source at a temperature ramp rate of 0.4° C. per minute or less. This result can be achieved, for example, by reducing the amount of catalyst to a suboptimal amount for rapid formation of the quat diester.

Abstract: Light-duty liquid detergents derived from metathesized natural oil feedstocks are disclosed. The detergents comprise water, at least one anionic surfactant, and at least one secondary surfactant derived from a metathesis-derived C10-C17 monounsaturated acid or its ester derivatives. In particular, the secondary surfactant is selected from C10 amidoamines, quaternized C10 or C12 amidoamines, C12 amidoamine oxides, C12 sulfobetaines, C12 amidoamine sulfobetaines, and C12 alkanolamides. The detergents noted above rival or outperform commercial baselines in standard foam tests for liquid detergents, particularly those used for dishwashing.

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: Liquid cleaning compositions are described that comprise sulfo-estolide (SE) salts, particular sodium, lithium or ammonium salts of sulfo-estolides, and alkyl ester sulfonates. The liquid cleaning compositions are clear, stable and substantially free of precipitates due to the use of sodium, lithium or ammonium salts of sulfo-estolide rather than a potassium sulfo-estolide salt in the composition. The liquid cleaning compositions also have a total combined amount of saturated C16 and C18 fatty acids of less than about 5% by weight to prevent the formation of precipitates in the composition.

Abstract: Aqueous glyphosate formulations comprising a surfactant derived from metathesized natural oil feedstocks are disclosed. The formulations comprise a glyphosate salt, water, and a surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives. The surfactant is selected from C10 or C12 amine oxides, C10 or C12 quats, C10, C12, or C16 amidoamines, C10 or C12 amidoamine oxides, C10 imidazoline quats, C10 or C12 amidoamine quats, C10, C12, or C16 betaines, C16 amidoamine betaines, C18 diamidoamines, C18 diamidoamine oxides, C18 diamidoamine diquats, C18 diamidoamine oxide quats, C18 diamidoamine oxide betaines, Cis diamidoamine monobetaines, C18 diamidoamine monobetaine quats, C18 ester amidoamine quats, and amidoamines and their oxidized or quaternized derivatives made from self- or cross-metathesized palm or soybean oil.

Abstract: Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfitating the esteramines are also disclosed. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The esteramines and derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.