Processes of preparing estolide compounds that include removing sulfonate residues

Patent metadata

Field	Value
Publication number	US-9346900-B2
Application number	US-201514705729-A
Country	US
Kind code	B2
Filing date	May 6, 2015
Priority date	Jun 18, 2012
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

Provided herein are processes of preparing sulfonated estolide compounds, and the removal of sulfonate residues from those compounds to provide desulfonated estolide base oils. Exemplary sulfonated estolide compounds include those selected from the formula:

wherein z is an integer selected from 0 to 15; q is an integer selected from 0 to 15; x is, independently for each occurrence, an integer selected from 0 to 20; y is, independently for each occurrence, an integer selected 0 to 20; n is equal to or greater than 0; R 6 is selected from —OH, optionally substituted alkyl, and optionally substituted aryl; 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 compounds is independently optionally substituted.

First claim

The invention claimed is:

1. At least one compound of Formula I:

wherein
W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , and W 7 , independently for each occurrence, are selected from —CH 2 —, —CH═CH—, and —CHR 5 —;
Q 1 , Q 2 , and Q 3 , independently for each occurrence, are selected from —CH 3 , —CH═CH 2 , —CH(R 5 )CH 3 , and —CH 2 R 5 , provided that at least one of W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , or W 7 is —CHR 5 —, or at least one of Q 1 , Q 2 , or Q 3 is —CH 2 R 5 ;
R 5 , independently for each occurrence, is selected from —OS(O) 2 R 6 , wherein R 6 is selected from —OH, optionally substituted alkyl, and optionally substituted aryl;
z is an integer selected from 0 to 15;
p is an integer selected from 0 to 15;
q is an integer selected from 0 to 15;
x is, independently for each occurrence, an integer selected from 0 to 20;
y is, independently for each occurrence, an integer selected from 0 to 20;
n is equal to or greater than 0; 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 at least one compound according to claim 1 , wherein
x is, independently for each occurrence, an integer selected from 1 to 10;
y is, independently for each occurrence, an integer selected from 1 to 10;
n is an integer selected from 0 to 8; and
R 2 is an 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 at least one compound according to claim 1 , wherein x is, independently for each occurrence, an integer selected from 7 and 8.

4. The at least one compound according to claim 3 , wherein y is, independently for each occurrence, an integer selected from 7 and 8.

5. The at least one compound according to claim 1 , wherein R 2 is an unsubstituted alkyl that is saturated or unsaturated, and branched or unbranched.

6. The at least one compound according to claim 5 , wherein R 2 is selected from C 6 to C 12 alkyl.

7. The at least one compound according to claim 6 , wherein R 2 is saturated.

8. The at least one compound according to claim 6 , wherein R 2 is branched.

9. The at least one compound according to claim 1 , wherein at least one of W 1 , W 2 , or W 3 is —CHR 5 —.

10. The at least one compound according to claim 1 , wherein R 6 , independently for each occurrence, is selected from optionally substituted alkyl.

11. The at least one compound according to claim 10 , wherein R 6 , independently for each occurrence, is selected from unsubstituted alkyl.

12. The at least one compound according to claim 1 , wherein the at least one compound is selected from compounds of Formula III:

13. The at least one compound according to claim 12 , wherein z is an integer selected from 7 and 8.

14. The at least one compound according to claim 13 , wherein q is an integer selected from 7 and 8.

15. The at least one compound according to claim 12 , wherein n is an integer selected from 0 to 12.

16. The at least one compound according to claim 12 , wherein R 6 is —OH.

17. The at least one compound according to claim 12 , wherein q is 0.

18. The at least one compound according to claim 12 , wherein R 6 , independently for each occurrence, is selected from optionally substituted alkyl.

19. The at least one compound according to claim 18 , wherein R 6 , independently for each occurrence, is selected from unsubstituted alkyl.

20. The at least one compound according to claim 12 , wherein R 6 , independently for each occurrence, is selected from optionally substituted aryl.

Assignees

• Biosynthetic Technologies Llc

Inventors

• Likhotvorik Igor
• Arnold Chris
• Thompson Travis
• Hoglen Dean Kent
• Williams Eric Lee
• Lutz Marlon

Classifications

• C07C69/604

  Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups · CPC title

• C07C67/303

  by hydrogenation of unsaturated carbon-to-carbon bonds · CPC title

• C07C303/02

  of sulfonic acids or halides thereof · CPC title

• C11C3/14

  by isomerisation {(isomerisation induced by hydrogenation C11C3/12)} · CPC title

• C07C67/327

  by elimination of functional groups containing oxygen only in singly bound form · CPC title