Application-specific finished lubricant compositions comprising a bio-derived ester component and methods of making same

Abstract

The present invention is generally directed to methods of making application-specific finished lubricant compositions comprising bio-derived diester species. In some embodiments, bio-derived fatty acid moieties are reacted with Fischer-Tropsch/gas-to-liquids reaction products and/or by-products (e.g., gas-to-liquids-produced α-olefins) to yield bio-derived diester species that can then be selectively blended with base oil and one or more additive species to yield an application-specific finished lubricant product having a biomass-derived component.

1 . A process for making lubricant compositions, said process comprising the steps of:
 a) preparing a quantity of epoxidized olefins, wherein said step of preparing comprises the sub-steps of:
 i) isolating α-olefins made from a gas-to-liquids process to yield isolated α-olefins; 
 ii) isomerizing at least a majority of the isolated α-olefins to yield a quantity of internalized olefins; and 
 iii) epoxidizing at least a majority of the internalized olefins to form a quantity of epoxidized olefins comprising an epoxide ring; and 
   b) obtaining a quantity of esterification agents, the esterification agents being derived from triglyceride-borne fatty acid moieties, whereby said derivation yields esterification agents selected from the group consisting of carboxylic acids, acyl halides, acyl anhydrides, and combinations thereof; wherein the step of obtaining comprises the sub-steps of:
 i′) selecting a biomass source comprising triglycerides, said triglycerides comprising fatty acid moieties of appropriate length; 
 ii′) liberating a majority of the fatty acid moieties from the triglyceride molecules of which they are a component so as to yield esterification agents; 
   c) esterifying at least a majority of the epoxidized olefins with the esterification agents so as to yield a quantity of diester species; and   d) combining the quantity of diester species with a quantity of base oil and an additive component comprising at least one additive selected from the group consisting of antioxidants, detergents, anti-wear agents, metal deactivators, corrosion inhibitors, rust inhibitors, friction modifiers, anti-foaming agents, viscosity index improvers, demulsifying agents, emulsifying agents, tackifiers, complexing agents, extreme pressure additives, pour point depressants, and combinations thereof;   
       wherein selection of the at least one additive is directed largely by the end-use of the lubricant composition being made, wherein said lubricant composition can be of a type selected from the group consisting of turbine oils, metalworking fluids, hydraulic fluids, compressor oils, chain oils, farm equipment engine oils, tractor hydraulic fluids, marine oils, paper machine oils, spindle and textile oils, trailer wheel bearing greases, and combinations thereof. 
     
     
         2 . The process of  claim 1 , wherein the sub-step of isolating the α-olefins comprises their separation from a largely paraffinic GTL product. 
     
     
         3 . The process of  claim 1 , wherein the sub-step of isomerizing involves use of an olefin isomerization catalyst. 
     
     
         4 . The process of  claim 1 , wherein the sub-step of epoxidizing is enzymatically-facilitated. 
     
     
         5 . The process of  claim 1 , wherein the sub-step of liberating triglyceride-borne fatty acid moieties comprises hydrolyzing the triglycerides to yield carboxylic acids as esterification agents. 
     
     
         6 . The process of  claim 5 , further comprising a sub-step of substantially separating the carboxylic acids on the basis of their degree of unsaturation so that the esterification agents used in the subsequent step of esterifying are substantially homogeneous in terms of their degree of unsaturation. 
     
     
         7 . The process of  claim 1 , wherein the step of esterifying the epoxidized olefins proceeds through a dihydroxide intermediate. 
     
     
         8 . The process of  claim 7 , wherein the dihydroxide intermediate is reacted with the esterification agent in the presence of an acid catalyst. 
     
     
         9 . The process of  claim 1 , wherein the step of esterifying the epoxidized olefins is carried directly via reaction between the epoxidized olefin and the esterification agent. 
     
     
         10 . The process of  claim 9 , wherein the step of esterifying the epoxidized olefins is carried out in the presence of an acid catalyst. 
     
     
         11 . The process of  claim 10 , 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. 
     
     
         12 . The process of  claim 1 , wherein, in the step of combining, the base oil is selected from the group consisting of GTL base oils, mineral base oils, diester-based base oils, and mixtures thereof. 
     
     
         13 . 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-cecanoyloxy-1-pentyl-heptyl ester and its isomers, dodecanoic acid-2-dodecanoyloxy-1-pentyl-heptyl ester and isomers, tetradecanoic acid 1-penty-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-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. 
     
     
         14 . The process of  claim 12 , wherein the base oil is a GTL base oil, and wherein the quantity of diester component serves to facilitate dispersion of the additive component in the base oil. 
     
     
         15 . The process of  claim 1 , wherein the sub-step of selecting a biomass source comprising triglycerides is based on identification and sufficient content of triglyceride molecules bearing fatty acid moieties of length more desirably suitable for use as a particular lubricant composition. 
     
     
         16 . The process of  claim 1 , wherein the lubricant composition is a hydraulic fluid having a pour point of from about −80° C. to about 0° C. 
     
     
         17 . The process of  claim 1 , wherein the lubricant composition is a turbine oil having a VI of from at least 90 to at most 130, and having an RPVOT oxidative stability of from at least 250 minutes to at most 2300 minutes. 
     
     
         18 . The process of  claim 1 , wherein the lubricant composition is a metalworking fluid having a pour point of from about −20° C. to about 0° C. 
     
     
         19 . The process of  claim 1 , wherein the lubricant composition is a compressor oil having a VI of from at least 90 to at most 130, and having a pour point of from at least −60° C. to at most 0° C. 
     
     
         20 . The process of  claim 1 , wherein the lubricant composition is a chain oil having a VI in the range of from at least 50 to at most 130, and having an aniline point in the range of from at least 0° C. to at most 130° C.