High-and low-viscosity estolide base oils and lubricants

Abstract

Provided herein are compounds of the formula: 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 1 , R 3 , and R 4 , independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, wherein compositions comprising the compounds are characterized by particular combinations of values for estolide number, kinematic viscosity, and pour point. Also provided are compositions containing the compounds and methods of making both the compounds and compositions thereof.

1 - 178 . (canceled) 
     
     
         179 . A composition consisting essentially of at least one estolide compound, said composition having:
 an EN that is an integer or fraction of an integer selected from 1.0 to 1.6, wherein the EN is the average number of estolide linkages in compounds according to Formula I; and   a kinematic viscosity within the ranges of about 28 cSt to about 38 cSt at when measured at 40° C., and about 5 cSt to about 9 cSt at when measured at 100° C.,
 wherein the at least one estolide compound is selected from compounds of Formula I: 
   
       
         
           
           
               
               
           
         
         wherein 
         x is, independently for each occurrence, an integer selected from 7 and 8; 
         y is, independently for each occurrence, an integer selected from 7 and 8; 
         n is an integer selected from 0 to 4; 
         R 1  is an unsubstituted C 1  to C 18  alkyl that is saturated or unsaturated, and branched or unbranched; and 
         R 2  is an unsubstituted C 1  to C 18  alkyl that is saturated or unsaturated, and branched or unbranched,
 wherein each fatty acid chain residue of said at least one compound is unsubstituted. 
 
       
     
     
         180 . The composition according to  claim 179 , wherein R 1  is selected from C 7  to C 17  alkyl. 
     
     
         181 . The composition according to  claim 179 , wherein R 1  is selected from C 5  alkyl, C 7  alkyl, C 9  alkyl, C 11  alkyl, C 13  alkyl, and C 15  alkyl. 
     
     
         182 . The composition according to  claim 179 , wherein R 1  is saturated. 
     
     
         183 . The composition according to  claim 182 , wherein R 1  is selected from C 5  alkyl, C 7  alkyl, C 9  alkyl, C 11  alkyl, C 13  alkyl, and C 15  alkyl. 
     
     
         184 . The composition according to  claim 183 , wherein R 1  is unbranched. 
     
     
         185 . The composition according to  claim 184 , wherein R 2  is saturated. 
     
     
         186 . The composition according to  claim 185 , wherein R 2  is branched. 
     
     
         187 . The composition according to  claim 186 , wherein R 2  is a C 6  to C 12  alkyl. 
     
     
         188 . The composition according to  claim 187 , wherein R 2  is 2-ethylhexyl. 
     
     
         189 . A composition consisting essentially of at least one estolide compound, said composition having:
 an EN that is an integer or fraction of an integer selected from 1.0 to 1.6, wherein the EN is the average number of estolide linkages in compounds according to Formula I;   an iodine value (IV) of 0; and   a kinematic viscosity within the ranges of about 28 cSt to about 38 cSt at when measured at 40° C., and about 5 cSt to about 9 cSt at when measured at 100° C.,
 wherein the at least one estolide compound is selected from compounds of Formula I: 
   
       
         
           
           
               
               
           
         
         wherein 
         x is, independently for each occurrence, an integer selected from 7 and 8; 
         y is, independently for each occurrence, an integer selected from 7 and 8; 
         n is an integer selected from 0 to 4; 
         R 1  is an unsubstituted C 1  to C 18  alkyl that is saturated, and branched or unbranched; and 
         R 2  is an unsubstituted C 1  to C 18  alkyl that is saturated, and branched or unbranched,
 wherein each fatty acid chain residue of said at least one compound is unsubstituted. 
 
       
     
     
         190 . The composition according to  claim 189 , wherein R 1  is selected from C 5  alkyl, C 7  alkyl, C 9  alkyl, C 11  alkyl, C 13  alkyl, and C 15  alkyl. 
     
     
         191 . The composition according to  claim 190 , wherein R 1  is unbranched. 
     
     
         192 . The composition according to  claim 191 , wherein R 2  is branched. 
     
     
         193 . The composition according to  claim 192 , wherein R 2  is a C 6  to C 12  alkyl. 
     
     
         194 . The composition according to  claim 193 , wherein R 2  is 2-ethylhexyl. 
     
     
         195 . The composition according to  claim 193 , wherein the composition exhibits an acid value of about 0.08 mg KOH/g.