Abstract: Chemically-modified fatty acids prepared by reacting epoxidized fatty acids, their esters or triglyceride oils with borate compounds. The fatty acid derivatives produced are of the formula: wherein R is an H, branched or straight chain alkyl or alkenyl group, aromatic-containing group, glycerol, or glyceride, R? is a C3 to C29 aliphatic chain comprising one or more of the derivatized methylene groups of the formula: wherein m, n, and p are independently selected from 0 and 1; X is selected from O, NH, C(O)O, S, —C?N, —N?C?O, —N?C; and a borate of the formula: and R1 is selected from aryl, and straight, branched, cyclic or heterocyclic hydrocarbons or substituted hydrocarbons. These fatty acid derivatives have utility as antiwear/antifriction additives for industrial oils, fuels, and automotive applications.

Abstract: Chemically-modified fatty acids are prepared by reacting epoxidized fatty acids, their esters or triglyceride oils with amines of cyclic or aromatic hydrocarbons. The fatty acid derivatives produced are of the formula: wherein R is an H, branched or straight chain alkyl or alkenyl group, aromatic-containing group, glycerol, or glyceride, R? is a C3 to C29 aliphatic chain comprising one or more of the derivatized methylene groups of the formula: wherein R1 and R2 are independently selected from the group consisting of H, cyclic hydrocarbons, substituted cyclic hydrocarbons, and aryl groups, with the proviso that only one of said R1 and R2 may be H. These fatty acid derivatives have utility as antiwear/antifriction additives for industrial oils and automotive applications.

Abstract: Chemically-modified triglycerides are prepared by reacting epoxidized triglyceride oils with phosphorus-based acid hydroxide or esters. The phosphorus-containing triglyceride derivatives are of the formula: wherein R1?, R2? and R3? are independently selected from C3 to C29 aliphatic fatty acid residues, at least one of which comprising one or both of the derivatized methylene groups of the formula: wherein m is 0, 1 or 2, n is 0 or 1, q is 1, 2 or 3, and R and R? are independently selected from the group consisting of H, straight, branched or cyclic hydrocarbons and substituted hydrocarbons, and aryl groups. The phosphorus-containing triglyceride derivatives so produced have utility as antiwear/antifriction additives for industrial oils and automotive applications.

Abstract: Fatty acid ester derivatives and a process for their production from unsaturated fatty acids are disclosed. The process comprises: a) reacting an unsaturated fatty acid or an ester thereof having one or more sites of unsaturation, with an epoxidation reagent to form a fatty acid epoxide wherein at least one of the sites of unsaturation of the fatty acid or fatty acid ester is converted to an oxirane ring; and b) reacting the fatty acid epoxide produced in a) with a carboxylic acid to form a hydroxy fatty acid ester derivative wherein the oxirane ring is opened and converted to a hydroxy ester comprising a hydroxyl group at one carbon of the opened oxirane ring and an ester of the carboxylic acid at the other carbon of the opened oxirane ring.

Abstract: Chemically-modified fatty acids prepared by reacting epoxidized fatty acids, their esters or triglyceride oils with borate compounds. The fatty acid derivatives produced are of the formula: wherein R is an H, branched or straight chain alkyl or alkenyl group, aromatic-containing group, glycerol, or glyceride, R? is a C3 to C29 aliphatic chain comprising one or more of the derivatized methylene groups of the formula: wherein m, n, and p are independently selected from 0 and 1; X is selected from O, NH, C(O)O, S, —C?N, —N?C?O, —N?C; and a borate of the formula: and R1 is selected from aryl, and straight, branched, cyclic or heterocyclic hydrocarbons or substituted hydrocarbons. These fatty acid derivatives have utility as antiwear/antifriction additives for industrial oils, fuels, and automotive applications.

Abstract: Fatty acid ester derivatives and a process for their production from unsaturated fatty acids are disclosed. The process comprises: a) reacting an unsaturated fatty acid or an ester thereof having one or more sites of unsaturation, with an epoxidation reagent to form a fatty acid epoxide wherein at least one of the sites of unsaturation of the fatty acid or fatty acid ester is converted to an oxirane ring; and b) reacting the fatty acid epoxide produced in a) with a carboxylic acid to form a hydroxy fatty acid ester derivative wherein the oxirane ring is opened and converted to a hydroxy ester comprising a hydroxyl group at one carbon of the opened oxirane ring and an ester of the carboxylic acid at the other carbon of the opened oxirane ring.

Abstract: A novel class of chemically-modified vegetable oils is prepared by reacting epoxidized triglyceride oils with thiols. The resultant poly(hydroxy thioether) derivatives have utility as antiwear/antifriction additives for environmentally-friendly industrial oils and automotive applications.