Low viscosity low volatility benzoate monoester lubricating oil base stocks and methods of use thereof

Abstract

A composition including one or more benzoate monoester compounds represented by the formulae (I), (II), (III), (IV) and (V) as defined herein. The composition has a viscosity (KV100) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800. A process for producing the composition, a lubricating oil base stock and lubricating oil containing the composition, and a method for improving one or more of thermal and oxidative stability, solubility and dispersancy of polar additives, deposit control and traction control in a lubricating oil by using as the lubricating oil a formulated oil containing the composition.

1 . A composition comprising one or more compounds represented by the formula selected from the group consisting of 
       
         
           
           
               
               
           
         
         wherein R 2  is a H, F, methoxy, methyl or ethyl group; R 3  is a H, F, methoxy or methyl group; R 4  is a H, F methoxy or methyl group; R 5  is H and R 6  is H or a methyl group
 wherein said composition has a viscosity (K V100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800. 
 
       
     
     
         2 . The composition of  claim 1  which has a viscosity (K V100 ) from about 2 cSt to about 8 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about 25 to about 150 as determined by ASTM D2270, and a Noack volatility of no greater than 25 percent as determined by ASTM D5800. 
     
     
         3 . The composition of  claim 1 , wherein the composition is selected from the group consisting of 2-butyloctyl 4-butyl benzoate, 2-ethylhexyl 4-heptylbenzoate, butyloctyl 4-cyano benzoate, 2-hexyldecyl 4-methyl benzoate, 2-hexyldecyl 2-methyl benzoate, 2-hexyldecyl 3-methyl benzoate, 2-hexyldecyl 2,6 dimethyl benzoate, 2-hexyldecyl 2-ethylbenzoate, 2-hexyldecyl 2-methoxybenzoate, 2-hexyldecyl 3-methoxybenzoate, 2-hexyldecyl 4-methoxybenzoate, 2-hexyldecyl 2-fluorobenzoate, 2-hexyldecyl 3-fluorobenzoate, 2-hexyldecyl 4-fluorobenzoate, and combinations thereof. 
     
     
         4 . A composition comprising one or more compounds represented by the formula selected from the group consisting of 
       
         
           
           
               
               
           
         
         wherein R 2  is a H, F, methoxy, methyl or ethyl group; R 3  is a H, F, methoxy or methyl group; R 4  is a H, F methoxy or methyl group; R 5  is H and R 6  is H or a methyl group
 wherein said composition has a viscosity (K V100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800; 
 wherein said compound of formula (I) is produced by a process comprising reacting 2-butyloctanol with 4-butylbenzoic acid, optionally in the presence of a catalyst and a solvent, under reaction conditions sufficient to produce the compound of formula (I); or wherein said compound of formula (II) is produced by a process comprising reacting 2-ethylhexanol with 4-heptylbenzoic acid, optionally in the presence of a catalyst and a solvent, under reaction conditions sufficient to produce the compound of formula (II); or wherein said compound of formula (III) is produced by a process comprising reacting 2-butyloctanol with 4-nitrilebenzoic acid, optionally in the presence of a catalyst and a solvent, under reaction conditions sufficient to produce the compound of formula (III); or wherein said compound of formula (IV) is produced by a process comprising reacting 2-hexyldecan-1-ol with 4-methylbenzoic acid, optionally in the presence of a catalyst and a solvent, under reaction conditions sufficient to produce the compound of formula (IV). 
 
       
     
     
         5 . The composition of  claim 4  which has a viscosity (K V100 ) from about 2 cSt to about 8 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about 25 to about 150 as determined by ASTM D2270, and a Noack volatility of no greater than 25 percent as determined by ASTM D5800. 
     
     
         6 . A lubricating oil base stock comprising one or more compounds represented by the formula selected from the group consisting of 
       
         
           
           
               
               
           
         
         wherein R 2  is a H, F, methoxy, methyl or ethyl group; R 3  is a H, F, methoxy or methyl group; R 4  is a H, F methoxy or methyl group; R 5  is H and R 6  is H or a methyl group
 wherein said lubricating oil base stock has a viscosity (K V100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800. 
 
       
     
     
         7 . The lubricating oil base stock of  claim 6  which has a viscosity (K V100 ) from about 2 cSt to about 8 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about 25 to about 150 as determined by ASTM D2270, and a Noack volatility of no greater than 25 percent as determined by ASTM D5800. 
     
     
         8 . The lubricating oil base stock of  claim 6 , wherein the lubricating oil base stock is selected from the group consisting of 2-butyloctyl 4-butyl benzoate, 2-ethylhexyl 4-heptylbenzoate, butyloctyl 4-cyano benzoate, 2-hexyldecyl 4-methyl benzoate, 2-hexyldecyl 2-methyl benzoate, 2-hexyldecyl 3-methyl benzoate, 2-hexyldecyl 2,6 dimethyl benzoate, 2-hexyldecyl 2-ethylbenzoate, 2-hexyldecyl 2-methoxybenzoate, 2-hexyldecyl 3-methoxybenzoate, 2-hexyldecyl 4-methoxybenzoate, 2-hexyldecyl 2-fluorobenzoate, 2-hexyldecyl 3-fluorobenzoate, 2-hexyldecyl 4-fluorobenzoate, and combinations thereof. 
     
     
         9 . The lubricating oil base stock of  claim 6  further comprising one or more of a viscosity improver, antioxidant, detergent, dispersant, pour point depressant, corrosion inhibitor, metal deactivator, seal compatibility additive, anti-foam agent, inhibitor, and anti-rust additive. 
     
     
         10 . A lubricating oil comprising a lubricating oil base stock component, and a monoester cobase stock component; wherein said monoester cobase stock comprises one or more compounds represented by the formula selected from the group consisting of 
       
         
           
           
               
               
           
         
         wherein R 2  is a H, F, methoxy, methyl or ethyl group; R 3  is a H, F, methoxy or methyl group; R 4  is a H, F methoxy or methyl group; R 5  is H and R 6  is H or a methyl group
 wherein said lubricating oil has a viscosity (K V100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800. 
 
       
     
     
         11 . The lubricating oil of  claim 10  wherein the lubricating oil base stock comprises a Group I, II, III, IV or V base oil stock. 
     
     
         12 . The lubricating oil of  claim 10  wherein the lubricating oil base stock comprises a polyalphaolefin (PAO) or gas-to-liquid (GTL) oil base stock. 
     
     
         13 . The lubricating oil of  claim 10  wherein the lubricating oil base stock is present in an amount from about 1 weight percent to about 99 weight percent, and the monoester cobase stock is present in an amount from about 1 weight percent to about 99 weight percent, based on the total weight of the lubricating oil. 
     
     
         14 . The lubricating oil of  claim 10  which has a viscosity (K V100 ) from about 2 cSt to about 8 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about 25 to about 150 as determined by ASTM D2270, and a Noack volatility of no greater than 25 percent as determined by ASTM D5800. 
     
     
         15 . The lubricating oil of  claim 10 , wherein the monoester cobase stock is is selected from the group consisting of 2-butyloctyl 4-butyl benzoate, 2-ethylhexyl 4-heptylbenzoate, butyloctyl 4-cyano benzoate, 2-hexyldecyl 4-methyl benzoate, 2-hexyldecyl 2-methyl benzoate, 2-hexyldecyl 3-methyl benzoate, 2-hexyldecyl 2,6 dimethyl benzoate, 2-hexyldecyl 2-ethylbenzoate, 2-hexyldecyl 2-methoxybenzoate, 2-hexyldecyl 3-methoxybenzoate, 2-hexyldecyl 4-methoxybenzoate, 2-hexyldecyl 2-fluorobenzoate, 2-hexyldecyl 3-fluorobenzoate, 2-hexyldecyl 4-fluorobenzoate, and combinations thereof. 
     
     
         16 . The lubricating oil of  claim 10  further comprising one or more of a viscosity improver, antioxidant, detergent, dispersant, pour point depressant, corrosion inhibitor, metal deactivator, seal compatibility additive, anti-foam agent, inhibitor, and anti-rust additive. 
     
     
         17 . A method for improving one or more of thermal and oxidative stability, solubility and dispersancy of polar additives, deposit control and traction control in a lubricating oil comprising:
 providing a lubricating oil including a lubricating oil base stock component, and a monoester cobase stock component; wherein said monoester cobase stock comprises one or more compounds represented by the formula selected from the group consisting of   
       
         
           
           
               
               
           
         
       
       wherein R 2  is a H, F, methoxy, methyl or ethyl group; R 3  is a H, F, methoxy or methyl group; R 4  is a H, F methoxy or methyl group; R 5  is H and R 6  is H or a methyl group
 wherein said lubricating oil has a viscosity (K V100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800, and 
 using the lubricating oil in a formulated oil to improve one or more of thermal and oxidative stability, solubility and dispersancy of polar additives, deposit control and traction control. 
 
     
     
         18 . The method of  claim 17  wherein the lubricating oil base stock comprises a Group I, II, III, IV or V base oil stock. 
     
     
         19 . The method of  claim 17  wherein the lubricating oil base stock comprises a polyalphaolefin (PAO) or gas-to-liquid (GTL) oil base stock. 
     
     
         20 . The method of  claim 17  wherein the lubricating oil base stock is present in an amount from about 1 weight percent to about 99 weight percent, and the monoester cobase stock is present in an amount from about 1 weight percent to about 99 weight percent, based on the total weight of the lubricating oil. 
     
     
         21 . The method of  claim 17  wherein the lubricating oil has a viscosity (K V100 ) from about 2 to about 8 at 100° C. as determined by ASTM D445, a viscosity index (VI) from about 25 to about 150 as determined by ASTM D2270, and a Noack volatility of no greater than 25 percent as determined by ASTM D5800. 
     
     
         22 . The method of  claim 17 , wherein the monoester cobase stock is selected from the group consisting of 2-butyloctyl 4-butyl benzoate, 2-ethylhexyl 4-heptylbenzoate, butyloctyl 4-cyano benzoate, 2-hexyldecyl 4-methyl benzoate, 2-hexyldecyl 2-methyl benzoate, 2-hexyldecyl 3-methyl benzoate, 2-hexyldecyl 2,6 dimethyl benzoate, 2-hexyldecyl 2-ethylbenzoate, 2-hexyldecyl 2-methoxybenzoate, 2-hexyldecyl 3-methoxybenzoate, 2-hexyldecyl 4-methoxybenzoate, 2-hexyldecyl 2-fluorobenzoate, 2-hexyldecyl 3-fluorobenzoate, 2-hexyldecyl 4-fluorobenzoate, and combinations thereof. 
     
     
         23 . The method of  claim 17  wherein the lubricating oil further comprises one or more of a viscosity improver, antioxidant, detergent, dispersant, pour point depressant, corrosion inhibitor, metal deactivator, seal compatibility additive, anti-foam agent, inhibitor, and anti-rust additive. 
     
     
         24 . A composition comprising one or more compounds represented by the formula: 
       
         
           
           
               
               
           
         
         wherein X is a C 1 -C 7  alkyl group, a C 1 -C 7  alkoxy group, a C 1 -C 7  haloalkyl group, a C 1 -C 7  haloalkoxy group, a halogen, a cyano group or a nitro group; n is from 1 to 5; P is from 1 to 12; Q is from 0 to 12; and P+Q is greater than 4, and
 wherein the composition has a viscosity (K V100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800. 
 
       
     
     
         25 . The composition of  claim 24  which has a viscosity (K V100 ) from about 2 cSt to about 8 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about 25 to about 150 as determined by ASTM D2270, and a Noack volatility of no greater than 25 percent as determined by ASTM D5800.