Synthesis of Diester-Based Lubricants from Enzymatically-Directed Epoxides

Abstract

The present invention is generally directed to methods of making diester-based lubricant compositions, wherein formation of diester species proceeds via esterification of epoxide intermediates, and wherein the epoxide intermediates are generated via an enzymatically-driven mechanism. In some embodiments, the methods for making such diester-based lubricants utilize a biomass precursor and/or low value (e.g., Fischer-Tropsch (FT) olefins and/or alcohols) so as to produce high value diester-based lubricants. In some embodiments, such diester-based lubricants are derived from FT olefins and fatty acids. The fatty acids can be from a bio-based source (i.e., biomass, renewable source) or can be derived from FT alcohols via oxidation.

What is claimed: 
     
         1 . A process comprising:
 a) epoxidizing an olefin having a carbon number of from 8 to 18 to form an epoxide comprising an epoxide ring, wherein said epoxidizing is enzymatically-driven in the presence of a carboxylic acid and a hydrogen peroxide initiator and said epoxidizing converts greater than 99% of the olefin to the epoxide;   b) opening the epoxide ring of the epoxide to form a diol; and   c) esterifying the diol with a C 2  to C 18  esterification agent to form a diester species having viscosity in the range of 3.8 to 6.0 cSt at 100° C. and a pour point of less than −12° C., and wherein said esterification agent is selected from the group consisting of carboxylic acids, acyl chlorides, and combinations thereof.   
     
     
         2 . The process of  claim 1 , wherein said epoxidizing is performed using a lipase. 
     
     
         3 . The process of  claim 2 , wherein said epoxidizing is performed using a lipase in the presence of a carboxylic acid and a hydrogen peroxide initiator. 
     
     
         4 . The process of  claim 3 , wherein the lipase is an immobilized lipase product based on a lipase from  Candida Antarctica.    
     
     
         5 . The process of  claim 1 , wherein the step of esterifying is catalyzed by the presence of an acid catalyst. 
     
     
         6 . The process of  claim 5 , wherein the acid catalyst is selected from the group consisting of H 3 PO 4 , H 2 SO 4 , sulfonic acid, Lewis acids, silica and alumina-based solid acids, Amberlyst, tungsten oxide, and combinations thereof. 
     
     
         7 . The process of  claim 1 , wherein the step of esterifying additionally comprises the presence of a carboxylic acid anhydride. 
     
     
         8 . The process of  claim 1 , wherein the olefin is a Fischer-Tropsch reaction product. 
     
     
         9 . The process of  claim 1 , wherein the olefin is derived from the pyrolysis of waste plastic. 
     
     
         10 . The process of  claim 1 , wherein the carboxylic acid is derived from biomass. 
     
     
         11 . The process of  claim 1 , wherein the diester species formed 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-decanoyloxy-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-hexyl 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-octanoyloxy-hexyl 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. 
     
     
         12 . The process of  claim 1 , wherein the diester species formed has a viscosity index in the range of 120 to 170. 
     
     
         13 . The process of  claim 1 , wherein the diester species formed has a pour point of less than −18° C. 
     
     
         14 . The process of  claim 1 , wherein the diester species formed has a pour point of less than −20° C. 
     
     
         15 . The process of  claim 1 , wherein the diester species formed has an oxidator BN value of greater than 12 hours. 
     
     
         16 . The process of  claim 1 , wherein the diester species formed has an oxidator BN value of greater than 20 hours. 
     
     
         17 . The process of  claim 1 , wherein the olefin is isomerized from an α-olefin to an internal olefin. 
     
     
         18 . The process of  claim 17 , wherein the olefin is double bond isomerized with an olefin isomerization catalyst. 
     
     
         19 . The process of  claim 1 , further comprising a step of blending the diester species with one or more other species selected from the group consisting of other diester species, Group I oils, Group II oils, Group III oils, and mixtures thereof. 
     
     
         20 . A process of  claim 1 , wherein the carboxylic acid is lauric acid.