An ester compound which can be used as the additive of the lubricating oil or the base oil of the lubricating oil, and a process for preparing the same and use thereof are provided. The ester has excellent viscosity-temperature properties and low-temperature properties and can be used as the base oil of the lubricating oil. In addition, the ester compound has excellent viscosity-temperature properties and low-temperature properties as the viscosity index improver, can significantly reduce the wear scar diameter of the base oil as the anti-wear agent, can significantly reduce the friction coefficient of the base oil as the friction modifier, and exhibits excellent anti-wear and anti-friction properties.

The present invention describes a process for obtaining a biolubricant from vegetable oil, which comprises the steps of (a) esterification reaction of the product of vegetable oil hydrolysis using a branched aliphatic alcohol; (b) epoxidation reaction of the esters obtained in step (a); and (c) nucleophilic substitution reaction of the epoxidated esters obtained in step (b) using a branched aliphatic alcohol. The present invention also describes a biolubricant obtained from the process. More specifically, a biolubricant is described that is produced from a ricinoleic fatty acid, whose formula is illustrated in FIG. 1 of the present invention, and where R.sub.1 is a hydroxyl or it is from the formula R.sub.3COO.sup.−, with R.sub.3 being an alkyl radical C.sub.1-C.sub.3, preferably a methyl radical; and R.sub.2 consists of a straight chain of hydrocarbons C.sub.4-C.sub.8 and a branched chain of hydrocarbons C.sub.1-C.sub.3.

The use as an anti-wear additive and/or friction modifier in a non-aqueous lubricant composition and/or in a fuel composition of at least one long chain fatty acid ester of a hydroxy carboxylic acid in which the long chain fatty acid has at least 4 carbon atoms and the ester is an oil-soluble ester of a mono- or poly-hydroxy carboxylic acid having 1 to 4 groups which are independently carboxylic acid groups or lower hydrocarbyl esters thereof and in which, when the hydroxy carboxylic acid is a mono-hydroxy carboxylic acid, the ester has a long chain fatty acid ester moiety of the hydroxy group of the hydroxy carboxylic acid and, when the hydroxy carboxylic acid is a poly-hydroxy carboxylic acid, the ester has independently long chain fatty acid ester moieties of one or two of the hydroxy groups of the poly-hydroxy carboxylic acid. Also, a non-aqueous lubricant composition and a fuel composition for an internal combustion engine which comprises at least one of said long chain fatty acid esters.

The use as an anti-wear additive and/or friction modifier in a non-aqueous lubricant composition and/or in a fuel composition of at least one long chain fatty acid ester of a hydroxy carboxylic acid in which the long chain fatty acid has at least 4 carbon atoms and the ester is an oil-soluble ester of a mono- or poly-hydroxy carboxylic acid having 1 to 4 groups which are independently carboxylic acid groups or lower hydrocarbyl esters thereof and in which, when the hydroxy carboxylic acid is a mono-hydroxy carboxylic acid, the ester has a long chain fatty acid ester moiety of the hydroxy group of the hydroxy carboxylic acid and, when the hydroxy carboxylic acid is a poly-hydroxy carboxylic acid, the ester has independently long chain fatty acid ester moieties of one or two of the hydroxy groups of the poly-hydroxy carboxylic acid. Also, a non-aqueous lubricant composition and a fuel composition for an internal combustion engine which comprises at least one of said long chain fatty acid esters.

The present techniques relate to facilitating conversion of biosourced triglycerides into fatty acid esters by combining the biosourced triglycerides with a carbonate ester in presence of an alcohol, under catalytic transesterification conditions. A reaction mixture can be heated to a reaction temperature to operate a transesterification of the biosourced triglyceride with the carbonate ester under catalysis of the alcohol thereby forming a single-phase composition comprising the fatty acid esters. The reaction mixture can have a molar ratio of the biosourced triglyceride over the carbonate ester between 1:0.1 and 1:20. Compositions comprising the produced single-phase composition, and optionally an additive, can be used as diesel, jet fuel or lubricant.

The present techniques relate to facilitating conversion of biosourced triglycerides into fatty acid esters by combining the biosourced triglycerides with a carbonate ester in presence of an alcohol, under catalytic transesterification conditions. A reaction mixture can be heated to a reaction temperature to operate a transesterification of the biosourced triglyceride with the carbonate ester under catalysis of the alcohol thereby forming a single-phase composition comprising the fatty acid esters. The reaction mixture can have a molar ratio of the biosourced triglyceride over the carbonate ester between 1:0.1 and 1:20. Compositions comprising the produced single-phase composition, and optionally an additive, can be used as diesel, jet fuel or lubricant.

The present invention describes a process for obtaining a biolubricant from vegetable oil, which comprises the steps of (a) esterification reaction of the product of vegetable oil hydrolysis using a branched aliphatic alcohol; (b) epoxidation reaction of the esters obtained in step (a); and (c) nucleophilic substitution reaction of the epoxidated esters obtained in step (b) using a branched aliphatic alcohol. The present invention also describes a biolubricant obtained from the process. More specifically, a biolubricant is described that is produced from a ricinoleic fatty acid, whose formula is illustrated in FIG. 1 of the present invention, and where R.sub.1 is a hydroxyl or it is from the formula R.sub.3COO.sup.−, with R.sub.3 being an alkyl radical C.sub.1-C.sub.3, preferably a methyl radical; and R.sub.2 consists of a straight chain of hydrocarbons C.sub.4-C.sub.8 and a branched chain of hydrocarbons C.sub.1-C.sub.3.

Disclosed are compositions containing at least one of the following: (1) estolide polyethylene glycol diesters; (2) hydroxy derived estolide polyethylene glycol diesters; (3) unsaturated hydroxy derived estolide polyethylene glycol diesters; (4) estolide trimetholpropane diesters; (5) hydroxy derived estolide trimetholpropane diesters; (6) unsaturated hydroxy derived estolide trimetholpropane diesters; (7) estolide epoxide polyethylene glycol diesters; (8) estolide dihydroxide polyethylene glycol diesters; (9) mono-capped hydroxy derived estolide epoxide polyethylene glycol diesters; (10) mono-capped hydroxy derived estolide dihydroxide polyethylene glycol diesters;
and mixtures thereof; and optionally a carrier. All the compounds can be used as a viscosity index improver thereby improving a lubricant's performance.

Disclosed are compositions containing at least one of the following: (1) estolide polyethylene glycol diesters; (2) hydroxy derived estolide polyethylene glycol diesters; (3) unsaturated hydroxy derived estolide polyethylene glycol diesters; (4) estolide trimetholpropane diesters; (5) hydroxy derived estolide trimetholpropane diesters; (6) unsaturated hydroxy derived estolide trimetholpropane diesters; (7) estolide epoxide polyethylene glycol diesters; (8) estolide dihydroxide polyethylene glycol diesters; (9) mono-capped hydroxy derived estolide epoxide polyethylene glycol diesters; (10) mono-capped hydroxy derived estolide dihydroxide polyethylene glycol diesters;
and mixtures thereof; and optionally a carrier. All the compounds can be used as a viscosity index improver thereby improving a lubricant's performance.

This disclosure provides a method for improving or maintaining antioxidant performance of a lubricating oil in an engine or other mechanical component lubricated with the lubricating oil by using as the lubricating oil a formulated oil. The formulated oil has a composition including a lubricating oil base stock as a major component, and at least one functionalized quercetin antioxidant, as a minor component. The at least one functionalized quercetin antioxidant is soluble in the lubricating oil. Antioxidant performance is improved or maintained as compared to antioxidant performance achieved using a lubricating oil containing a phenolic or aminic antioxidant, as determined by Lubricant Oxidation Test as described herein or Catalytic Oxidation Test as described herein. This disclosure also relates to lubricating oils having at least one functionalized quercetin antioxidant. The lubricating oils are useful as passenger vehicle engine oils (PVEO), commercial vehicle engine oils (CVEO), and other mechanical industrial applications.