Process for Preparing a Turbine Oil Comprising an Ester Component

Abstract

Provided is a process for preparing a turbine oil formulation comprised of a base oil selected from the group consisting of Group II, III and IV base oils and mixtures thereof, and an ester component comprised of at least one diester or triester species having ester links on adjacent carbons. The formulation exhibits less than 6 mg of sludge/100 ml of turbine oil and is imminently suitable for use as a turbine oil.

1 . A process for making a turbine oil, comprising the steps of:
 a) epoxidizing an olefin having from about 8 to about 16 carbon atoms to form an epoxide comprising an epoxide ring;   b) opening the epoxide ring of step a) and forming a diol;   c) esterifying the diol of step b) with an esterifying species to form a diester species, wherein the esterifying species is selected from the group consisting of carboxylic acids, acyl halides, acyl anhydrides, and combinations thereof, wherein the esterifying species has a carbon number of from 2 to 18; and   d) combining a quantity of the diester species with a quantity of Group II, III and/or IV base oils and an antioxidant composition comprised of at least one antioxidant other than a phenolic antioxidant.   
     
     
         2 . A process for making a turbine oil, comprising the steps of:
 a) epoxidizing an olefin having from about 8 to about 16 carbon atoms to form an epoxide comprising an epoxide ring;   b) reacting the epoxide comprising the epoxide ring with an esterifying species to form a diester species, wherein the esterifying species is selected from the group consisting of carboxylic acids, acyl halides, acyl anhydrides, and combinations thereof, wherein the esterifying species has a carbon number of from 2 to 18, and   c) combining a quantity of the diester species with a quantity of Group II, III and/or IV base oils and an antioxidant composition comprised of at least one antioxidant other than a phenolic antioxidant.   
     
     
         3 . A process for making a turbine oil, comprising the steps of:
 a) esterifying a mono-unsaturated fatty acid having from 10 to 22 carbon atoms with an alcohol thereby forming an unsaturated ester;   b) epoxidizing the unsaturated ester in step a) thereby forming an epoxy-ester species comprising an epoxide ring;   c) opening the ring of the epoxy-ester species in step b) thereby forming a dihydroxy ester;   d) esterifying the dihydroxy ester in step c) with an esterifying species to form a triester species, wherein the esterifying species is selected from the group consisting of carboxylic acids, acyl halides, acyl anhydrides, and combinations thereof, and wherein the esterifying species has a carbon number of from 2 to 19; and   e) combining a quantity of the diester species with a quantity of Group II, III and/or IV base oils and an antioxidant composition comprised of at least one antioxidant other than a phenolic antioxidant.   
     
     
         4 . A process for making a turbine oil, comprising the steps of:
 a) reducing a monosaturated fatty acid to a corresponding unsaturated alcohol;   b) epoxidizing the unsaturated alcohol to an epoxy fatty alcohol;   c) opening a ring of the epoxy fatty alcohol to make a corresponding triol;   d) esterifying the triol of step c) with an esterifying species to form a triester species, wherein the esterifying species is selected from the group consisting of carboxylic acids, acyl halides, acyl anhydrides, and combinations thereof, and wherein the esterifying species has a carbon number of from 2 to 19; and   e) combining a quantity of the diester species with a quantity of Group II, III and/or IV base oils and an antioxidant composition comprised of at least one antioxidant other than a phenolic antioxidant.   
     
     
         5 . A process for making a turbine oil, comprising the steps of:
 a) reducing a monosaturated fatty acid to a corresponding unsaturated alcohol;   b) epoxidizing the unsaturated alcohol to form a fatty alcohol epoxide;   c) esterifying the fatty alcohol epoxide with an esterifying species to form a triester species, wherein the esterifying species is selected from the group consisting of carboxylic acids, acyl halides, acyl anhydrides, and combinations thereof, and wherein the esterifying species has a carbon number of from 2 to 19; and   d) combining a quantity of the diester species with a quantity of Group II, III and/or IV base oils and an antioxidant composition comprised of at least one antioxidant other than a phenolic antioxidant.   
     
     
         6 . A process for making a turbine oil, comprising combining a quantity of a diester species having the following structure: 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3  and R 4  are identical or independently selected from hydrocarbon groups having from 2 to 17 carbon atoms, 
         with a quantity of Group II, III and/or IV base oils and an antioxidant composition comprised of at least one antioxidant other than a phenolic antioxidant. 
       
     
     
         7 . A process for making a turbine oil, comprising combining a quantity of a triester species having the following structure: 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3  and R 4  are identical or independently selected from hydrocarbon groups having from 2 to 20 carbon atoms and wherein “n” is an integer from 2 to 20, 
         with a quantity of Group II, III and/or IV base oils and an antioxidant composition comprised of at least one antioxidant other than a phenolic antioxidant. 
       
     
     
         8 . A process for making a turbine oil, comprising combining a quantity of a triester species having the following structure: 
       
         
           
           
               
               
           
         
         wherein R 2 , R 3 , and R 4  are identical or independently selected from C 2  to C 20  hydrocarbon groups, 
         with a quantity of Group II, III and/or IV base oils and an antioxidant composition comprised of at least one antioxidant other than a phenolic antioxidant. 
       
     
     
         9 . The process of  claim 6 , wherein the diester is selected from the group consisting of decanoic acid 2-decanoyloxy-1-hexyl-octyl ester and its isomers, tetradecanoic acid-1-hexyl-2-tetradecanoyloxy-octyl esters and its isomers, dodecanoic acid 2-dodecanoyloxy-1-hexyl-octyl ester and its isomers, hexanoic acid 2-hexanoyloxy-1-hexy-octyl ester and its isomers, octanoic acid 2-octanoyloxy-1-hexyl-octyl ester and its isomers, hexanoic acid 2-hexanoyloxy-1-pentyl-heptyl ester and isomers, octanoic acid 2-octanoyloxy-1-pentyl-heptyl ester and isomers, decanoic acid 2-decanoyloxy-1-pentyl-heptyl ester and isomers, decanoic acid-2-cecanoyloxy-1-pentyl-heptyl ester and its isomers, dodecanoic acid-2-dodecanoyloxy-1-pentyl-heptyl ester and isomers, tetradecanoic acid 1-pentyl-2-tetradecanoyloxy-heptyl ester and isomers, tetradecanoic acid 1-butyl-2-tetradecanoyloxy-hexy ester and isomers, dodecanoic acid-1-butyl-2-dodecanoyloxy-hexyl ester and isomers, decanoic acid 1-butyl-2-decanoyloxy-hexyl ester and isomers, octanoic acid 1-butyl-2-octanoyloxyhexyl ester and isomers, hexanoic acid 1-butyl-2-hexanoyloxy-hexyl ester and isomers, tetradecanoic acid 1-propyl-2-tetradecanoyloxy-pentyl ester and isomers, dodecanoic acid 2-dodecanoyloxy-1-propyl-pentyl ester and isomers, decanoic acid 2-decanoyloxy-1-propyl-pentyl ester and isomers, octanoic acid 1-2-octanoyloxy-1-propyl-pentyl ester and isomers, hexanoic acid 2-hexanoyloxy-1-propyl-pentyl ester and isomers, and mixtures thereof. 
     
     
         10 . The process of  claim 6 , wherein the antioxidant comprises an amine antioxidant. 
     
     
         11 . The process of  claim 6 , wherein the antioxidant comprises a mixture of a phenolic antioxidant and at least one other non-phenolic antioxidant. 
     
     
         12 . The process of  claim 6 , wherein the diester species is prepared using an esterifying species which is a carboxylic acid. 
     
     
         13 . The process of  claim 12 , wherein the carboxylic acid is derived from a bio-derived fatty acid. 
     
     
         14 . The process of  claim 12 , wherein the carboxylic acid is derived from alcohols generated by a Fisher-Tropsch process. 
     
     
         15 . The process of  claim 7 , wherein the triester species is prepared using an esterifying species which is a carboxylic acid. 
     
     
         16 . The process of  claim 15 , wherein the carboxylic acid is derived from a bio-derived fatty acid. 
     
     
         17 . The process of  claim 15 , wherein the carboxylic acid is derived from alcohols generated by a Fisher-Tropsch process. 
     
     
         18 . The process of  claim 7 , wherein the antioxidant comprises an amine antioxidant. 
     
     
         19 . The process of  claim 8 , wherein the antioxidant comprises an amine antioxidant. 
     
     
         20 . The process of  claim 7 , wherein the antioxidant comprises a mixture of a phenolic antioxidant and at least one other non-phenolic antioxidant. 
     
     
         21 . The process of  claim 8 , wherein the antioxidant comprises a mixture of a phenolic antioxidant and at least one other non-phenolic antioxidant. 
     
     
         22 . The process of  claim 8 , wherein the triester species is prepared using an esterifying species which is a carboxylic acid.