Industrial oil comprising a bio-derived ester

Abstract

An industrial oil composition comprises a major amount of an ester base oil comprised of at least one diester or triester species having a vicinal diester substituent and at least one additive. The use of such esters can provide biodegradable industrial oils having improved viscosity index, additive solvency, or both.

1 . An industrial oil comprising:
 a) a major amount of an ester base oil comprised of at least one diester or triester species having a vicinal diester substituent; and   b) at least one additive,   
       wherein the industrial oil is selected from the group consisting of a hydraulic oil, a rock drill oil, a saw guide oil, and a way oil. 
     
     
         2 . The industrial oil of  claim 1 , having a viscosity index of at least 140. 
     
     
         3 . The industrial oil of  claim 1 , which is substantially free of any viscosity index improver. 
     
     
         4 . The industrial oil of  claim 1 , having a pour point of −10° C. or lower. 
     
     
         5 . The industrial oil of  claim 1 , wherein at least a portion of the ester base oil is bio-derived. 
     
     
         6 . The industrial oil of  claim 1 , wherein the diester species has a following structure: 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , and R 4  are independently selected from hydrocarbon groups having from 2 to 17 carbon atoms. 
     
     
         7 . The industrial oil of  claim 1 , wherein the diester species is derived from a process comprising:
 a) epoxidizing an olefin having from 8 to 16 carbon atoms to form an epoxide;   b) hydrolyzing the epoxide to form a diol; and   c) esterifying the diol with an esterifying agent having from 2 to 18 carbon atoms to form the diester species, wherein the esterifying agent is selected from the group consisting of carboxylic acids, acyl halides, acid anhydrides, and combinations thereof.   
     
     
         8 . The industrial oil of  claim 1 , wherein the diester species is derived from a process comprising:
 a) epoxidizing an olefin having from 8 to 16 carbon atoms to form an epoxide; and   b) reacting the epoxide with an esterifying agent having from 2 to 18 carbon atoms to form the diester species, wherein the esterifying agent is selected from the group consisting of carboxylic acids, acyl halides, acid anhydrides, and combinations thereof.   
     
     
         9 . The industrial oil of  claim 1 , wherein the triester species has a following structure: 
       
         
           
           
               
               
           
         
       
       wherein R 5 , R 6 , R 7 , and R 8  are independently selected from hydrocarbon groups having from 2 to 20 carbon atoms and “n” is an integer from 2 to 20. 
     
     
         10 . The industrial oil of  claim 1 , wherein the triester species is derived from a process comprising:
 a) esterifying a mono-unsaturated fatty acid having from 10 to 22 carbon atoms with an alcohol to form an unsaturated ester;   b) epoxidizing the unsaturated ester to form an epoxy-ester species comprising an epoxide ring;   c) hydrolyzing the epoxide ring of the epoxy-ester species to form a dihydroxy-ester species; and   d) esterifying the dihydroxy-ester species with an esterifying agent having from 2 to 18 carbon atoms to form the triester species, wherein the esterifying agent is selected from the group consisting of carboxylic acids, acyl halides, acid anhydrides, and combinations thereof.   
     
     
         11 . The industrial oil of  claim 1 , wherein the ester base oil comprises a triester species having a following structure: 
       
         
           
           
               
               
           
         
       
       wherein R 9 , R 10 , R 11 , and R 12  are independently selected from hydrocarbon groups having from 2 to 20 carbon atoms, and wherein “n” is an integer from 2 to 20. 
     
     
         12 . The industrial oil of  claim 1 , wherein the triester species is derived from a process comprising:
 a) reducing a mono-unsaturated fatty acid to form an unsaturated alcohol;   b) epoxidizing the unsaturated alcohol to form an epoxy-alcohol species comprising an epoxide ring;   c) hydrolyzing the epoxide ring of the epoxy-alcohol species to form a triol; and   d) esterifying the triol with an esterifying agent having from 2 to 18 carbon atoms to form the triester species, wherein the esterifying agent is selected from the group consisting of carboxylic acids, acyl halides, acid anhydrides, and combinations thereof.   
     
     
         13 . The industrial oil of  claim 1 , wherein the triester species is derived from a process comprising:
 a) reducing a mono-unsaturated fatty acid to form an unsaturated alcohol;   b) epoxidizing the unsaturated alcohol to form an epoxy-alcohol species comprising an epoxide ring; and   c) esterifying the epoxy-alcohol species with an esterifying agent having from 2 to 18 carbon atoms to form the triester species, wherein the esterifying agent is selected from the group consisting of carboxylic acids, acyl halides, acid anhydrides, and combinations thereof.   
     
     
         14 . The industrial oil of  claim 1 , wherein the at least one additive is selected from the group consisting of pour point depressants, anti-wear agents, EP agents, detergents, dispersants, antioxidants, viscosity index improvers, friction modifiers, demulsifiers, foam inhibitors, corrosion inhibitors, rust inhibitors, seal swell agents, emulsifiers, wetting agents, lubricity improvers, metal deactivators, gelling agents, tackiness agents, bactericides, fungicides, thickeners, fluid-loss additives, and colorants. 
     
     
         15 . A method for improving an industrial oil, comprising:
 a) selecting an ester base oil comprised of at least one diester or triester species having a vicinal diester substituent; and   b) replacing at least a portion of an original base oil in an original industrial oil with the ester base oil to produce an improved industrial oil, wherein viscosity index, additive solvency or both of the improved industrial oil is higher compared to an original viscosity index, an original additive solvency or both of the original industrial oil without the ester base oil.   
     
     
         16 . The method of  claim 15 , wherein the original base oil is a naphthenic base oil. 
     
     
         17 . The method of  claim 15 , wherein the improved industrial oil is substantially free of any viscosity index improver. 
     
     
         18 . The method of  claim 15 , wherein the viscosity index of the improved industrial oil is at least 50 greater than the original viscosity index of the original industrial oil. 
     
     
         19 . The method of  claim 15 , wherein the viscosity index of the improved industrial oil is at least 70 greater than the original viscosity index of the original industrial oil.