IP Library Granted Patent US 9,346,900
Granted Patent B2
US 9,346,900 · App. 14/705,729 · Granted May 24, 2016

Processes of preparing estolide compounds that include removing sulfonate residues

Inventors: Igor Likhotvorik (Willmette, IL); Chris Arnold (Mount Prospect, IL); Travis Thompson (Anaheim, CA); Dean Kent Hoglen (Baton Rouge, LA); Eric Lee Williams (Zachary, LA); Marlon Lutz (Grayslake, IL)
Assignee: Biosynthetic Technologies, LLC
C08F20/64C07C67/327C07C69/604C07C305/04C11C3/006C11C3/08C11C3/14
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Quick Facts
Patent No.
US 9,346,900
App. No.
14/705,729
Granted
May 24, 2016
Kind
B2
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.

Claims (37)

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.

Assignments (6)
ASSIGNMENT OF SECURITY INTEREST Recorded Mar 23, 2018
From: EVONIK OIL ADDITIVES USA, INC.
To: BIOSYN HOLDINGS, LLC
Reel/Frame 045684/0293 →
ASSIGNMENT OF SECURITY INTEREST Recorded Mar 23, 2018
From: BP TECHNOLOGY VENTURES INC.
To: BIOSYN HOLDINGS, LLC
Reel/Frame 045688/0600 →
ASSIGNMENT OF SECURITY INTEREST Recorded Mar 23, 2018
From: EVONIK CORPORATION
To: BIOSYN HOLDINGS, LLC
Reel/Frame 045860/0547 →
SECURITY INTEREST Recorded Jan 30, 2018
From: BIOSYNTHETIC TECHNOLOGIES, LLC
To: BP TECHNOLOGY VENTURES INC.
Reel/Frame 045196/0587 →
SECURITY INTEREST Recorded Mar 18, 2016
From: BIOSYNTHETIC TECHNOLOGIES, LLC
To: EVONIK OIL ADDITIVES USA, INC.
Reel/Frame 038146/0859 →
SECURITY INTEREST Recorded Nov 30, 2015
From: BIOSYNTHETIC TECHNOLOGIES, LLC
To: EVONIK CORPORATION
Reel/Frame 037162/0364 →
Continuity (4)
Continuation 14049101 · Oct 8, 2013
Continuation 13787556 · Mar 6, 2013
Provisional Application 61661010 · Jun 18, 2012
Related Publication 20150315306A1 · Nov 5, 2015