Acetic acid-capped estolide base oils and methods of making the same

Abstract

Provided herein are compounds, including those of the Formula II in which n is an integer equal to or greater than 1; R 2 , is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R 3 , and R 4 , independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Also provided are compositions containing such compounds and methods of making both compounds and compositions thereof.

1 . A composition comprising at least one compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein 
         x is, independently for each occurrence, an integer selected from 7 and 8; 
         y is 0; 
         n is an integer selected from 1 to 12; and 
         R 2  is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; 
         wherein each fatty acid chain residue of said at least one compound is independently optionally substituted. 
       
     
     
         2 . The composition according to  claim 1 , wherein
 n is an integer selected from 1 to 8; and   R 2  is optionally substituted C 1  to C 22  alkyl that is saturated or unsaturated, and branched or unbranched,   wherein each fatty acid chain residue is unsubstituted.   
     
     
         3 . The composition according to  claim 2 , wherein
 n is an integer selected from 1 to 6.   
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . The composition according to  claim 1 , wherein R 2  is a branched or unbranched C 1  to C 20  alkyl that is saturated or unsaturated. 
     
     
         7 . The composition according to  claim 6 , wherein R 2  is selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, undecanyl, dodecanyl, tridecanyl, tetradecanyl, pentadecanyl, hexadecanyl, heptadecanyl, octadecanyl, nonadecanyl, and icosanyl, which are saturated or unsaturated and branched or unbranched. 
     
     
         8 . The composition according to  claim 1 , wherein R 2  is selected from C 6  to C 12  alkyl. 
     
     
         9 . The composition according to  claim 8 , wherein R 2  is 2-ethylhexyl. 
     
     
         10 . The composition according to  claim 1 , wherein R 2  is optionally substituted C 1  to C 18  alkyl that is saturated or unsaturated, and branched or unbranched. 
     
     
         11 . The composition according to  claim 1 , wherein R 2  is optionally substituted C 3  to C 20  alkyl that is saturated or unsaturated, and branched or unbranched. 
     
     
         12 . The composition according to  claim 1 , wherein R 2  is a branched or unbranched C 3  to C 20  alkyl that is saturated and unsubstituted. 
     
     
         13 . The composition according to  claim 1 , wherein said composition has an EN selected from an integer or fraction of an integer that is equal to or greater than 2, wherein the EN is the average number of estolide linkages in compounds according to Formula I, a kinematic viscosity equal to or less than 5 cSt when measured at 100° C. and/or equal to or less than 20 cSt when measured at 40° C., and a pour point equal to or lower than −36° C. 
     
     
         14 . The composition according to  claim 1 , wherein said composition has an EN that is an integer or fraction of an integer selected from 2 to 3, wherein the EN is the average number of estolide linkages in compounds according to Formula I. 
     
     
         15 . The composition according to  claim 1 , wherein said composition has a kinematic viscosity within a range from 18 cSt to 20 cSt at 40° C., and/or 4 cSt to 5 cSt at 100° C. 
     
     
         16 . The composition according to  claim 1 , wherein said composition exhibits a pour point of −38° C. to −42° C. 
     
     
         17 . The composition according to  claim 1 , wherein said composition comprises two or more compounds of Formula I. 
     
     
         18 . The composition according to  claim 1 , wherein said composition consists essentially of two or more compounds of Formula I. 
     
     
         19 - 51 . (canceled)