Maleinized ester derivatives

Abstract

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.

1 . A composition comprising a maleinized ester derivative made by the reaction of:
 (i) an unsaturated linear aliphatic carboxylic acid methyl ester comprising a linear hydrocarbon chain of about 8 to about 18 carbon atoms; and   (ii) maleic anhydride; and   (iii) a monohydric alcohol of 3 to about 12 carbon atoms;   wherein the maleinized ester derivative comprises at least two proximal ester groups and another ester group, the proximal ester groups and the another ester group containing straight chain alkyl groups of 3 to about 12 carbon atoms; the proximal ester groups being separated from the another ester group by at least about 8 carbon atoms.   
     
     
         2 . The composition of  claim 1  wherein the unsaturated linear aliphatic carboxylic acid methyl ester is reacted with the maleic anhydride to form a maleinized unsaturated carboxylic acid methyl ester, and the maleinized unsaturated carboxylic acid methyl ester is reacted with the monohydric alcohol to form the maleinized ester derivative. 
     
     
         3 . The composition of  claim 2  wherein prior to the reaction with the monohydric alcohol, the maleinized carboxylic acid methyl ester comprises a methyl ester group and a maleic anhydride group, the reaction with the monohydric alcohol comprising an esterification reaction with the maleic anhydride group and a transesterification reaction with the methyl ester group. 
     
     
         4 . The composition of  claim 2  wherein prior to the reaction with the monohydric alcohol, the maleinized carboxylic acid methyl ester comprises a methyl ester group and two maleic anhydride groups, the reaction with the monohydric alcohol comprising an esterification reaction with the maleic anhydride groups and a transesterification reaction with the methyl ester group. 
     
     
         5 . The composition of  claim 1  wherein the monohydric alcohol comprises a linear alcohol. 
     
     
         6 . The composition of  claim 1  wherein the maleinized ester derivative comprises a mono-triester, or a mixture of a mono-triester and a di-triester. 
     
     
         7 . The composition of  claim 1  wherein the maleinized ester derivative contains one or more carbon-carbon double bonds, the one or more carbon-carbon double bonds being hydrogenated to form saturated carbon bonds. 
     
     
         8 . The composition of  claim 1  claims wherein the unsaturated linear aliphatic carboxylic acid methyl ester comprises methyl 8-nonenoate, methyl 9-decenoate, methyl 10-undecenoate, methyl 9-dodecenoate, methyl 9-octadecenoate, or a mixture of two or more thereof. 
     
     
         9 . The composition of  claim 1  wherein the monohydric alcohol comprises 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, 1-decanol, 1-undecanol, 1-dodecanol, 2-methyl butanol, 3-methyl butanol, a C 10  branched alcohol, or a mixture of two or more thereof. 
     
     
         10 . The composition of  claim 1  wherein the unsaturated linear aliphatic carboxylic acid methyl ester comprises methyl 9-dodecenoate and the monohydric alcohol comprises 1-pentanol. 
     
     
         11 . The composition of  claim 1  wherein the unsaturated linear aliphatic carboxylic acid methyl ester is derived from a natural product. 
     
     
         12 . The composition of  claim 1  wherein the unsaturated linear aliphatic carboxylic acid methyl ester is derived from vegetable oil, algae oil, fungus oil, animal oil, animal fat, sucrose, lactose, glucose, fructose, canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower seed oil, tall oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, camellina oil, pennycress oil, castor oil, coriander oil, almond oil, wheat germ oil, bone oil, lard, tallow, poultry fat, algae oil, yellow grease, fish oil, sugar cane, sugar beet, corn syrup, or a mixture of two or more thereof. 
     
     
         13 . The composition of  claim 1  wherein the unsaturated linear aliphatic carboxylic acid methyl ester is derived from a natural product, the natural oil comprising a refined, bleached and/or deodorized natural product. 
     
     
         14 . The composition of  claim 13  wherein the refined, bleached and/or deodorized natural product comprises soybean oil. 
     
     
         15 . The composition of  claim 1  wherein the unsaturated linear aliphatic carboxylic acid methyl ester is derived from a metathesized natural product or a metathesized natural product derived unsaturated carboxylic acid and/or ester. 
     
     
         16 . The composition of  claim 15  wherein the metathesized natural product or metathesized natural product derived unsaturated carboxylic acid and/or ester is made by reacting one or more natural products and/or natural product derived unsaturated carboxylic acids and/or esters in the presence of a metathesis catalyst. 
     
     
         17 . The composition of  claim 15  wherein the metathesized natural product or metathesized natural product derived unsaturated carboxylic acid and/or ester is made by reacting one or more natural products and/or natural product derived unsaturated carboxylic acids and/or esters with another olefinic compound in the presence of a metathesis catalyst. 
     
     
         18 . The composition of  claim 16  wherein the metathesis catalyst comprises a metal carbene catalyst, the metal being ruthenium, molybdenum, osmium, chromium, rhenium, and/or tungsten. 
     
     
         19 . The composition of  claim 16  wherein the natural product or natural product derived unsaturated carboxylic acid and/or ester is partially hydrogenated prior to the reaction in the presence of the metathesis catalyst. 
     
     
         20 . A concentrate composition comprising from about 0.1% to about 99% by weight of the composition of  claim 1 , and a normally liquid diluent. 
     
     
         21 . A lubricant or functional fluid composition comprising the composition of  claim 1 . 
     
     
         22 . The lubricant or functional fluid composition of  claim 21  wherein the composition further comprises an API Group I oil, Group II oil, Group III oil, Group IV oil, Group V oil, natural oil, estolide, or a mixture of two or more thereof. 
     
     
         23 . The lubricant or functional fluid composition of  claim 21  wherein the lubricant or functional fluid composition further comprises a detergent, dispersant, corrosion inhibitor, oxidation inhibitor, antiwear agent, friction modifier, pourpoint depressant, anti-foam agent, metal deactivator, viscosity modifier, extreme pressure agent, demulsifier, seal swelling agent, or a mixture of two or more thereof. 
     
     
         24 . The lubricant or functional fluid composition of  claim 21  wherein the lubricant or functional fluid composition comprises a grease composition, the grease composition comprising lithium hydroxide, lithium hydroxide monohydrate, or a mixture thereof. 
     
     
         25 . A base oil for an engine oil comprising the composition of any of  claim 1  and a polyalphaolefin. 
     
     
         26 . The base oil of  claim 25  wherein the polyalphaolefin is PAO-4. 
     
     
         27 . The base oil of  claim 25  wherein the base oil comprises a maleinated ester derivative, the base oil comprising from about 10% to about 80% by weight of the maleinated ester derivative. 
     
     
         28 . The base oil of  claim 25  further comprising an antioxidant. 
     
     
         29 . An engine oil comprising a polyalphaolefin and a triester derived from maleinized methyl 9-dodecenoate and 1-pentanol. 
     
     
         30 . The engine oil of  claim 29  wherein the triester comprises a mixture of a mono-triester and a di-triester.