Compositions comprising estolide compounds and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-10240025-B2
Application number	US-201715831916-A
Country	US
Kind code	B2
Filing date	Dec 5, 2017
Priority date	Jun 17, 2011
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

Provided herein are compositions comprising at least one estolide compound of formula:

in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 1; R 1 , independently for each occurrence, is selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; 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 uses of the compositions described herein.

First claim

The invention claimed is:

1. A purified, optically active form of a compound of Formula I:

wherein
x is, independently for each occurrence, an integer selected from 2 to 8;
y is, independently for each occurrence, an integer selected from 2 to 8;
n is 0;
R 1 is an unsubstituted C 1 -C 20 alkyl that is saturated or unsaturated, and branched or unbranched; and
R 2 is hydrogen,
wherein each fatty acid chain residue of the compound is unsubstituted.

2. The compound of claim 1 , wherein x is 3.

3. The compound of claim 2 , wherein y is 12.

4. The compound of claim 1 , wherein x is 7.

5. The compound of claim 4 , wherein y is 8.

6. The compound of claim 5 , wherein R 1 is an unsubstituted C 13 -C 17 alkyl.

7. The compound of claim 6 , wherein R 1 is saturated.

8. The compound of claim 7 , wherein R 1 is unbranched.

9. The compound of claim 5 , wherein R 1 is an unsubstituted C 15 alkyl that is unbranched.

10. The compound of claim 9 , wherein R 1 is saturated.

11. A composition comprising the compound of claim 10 and at least one additive.

12. The compound of claim 1 , wherein the compound is enantiomerically pure.

13. A composition comprising at least one optically-active estolide compound of Formula I:

wherein
x is, independently for each occurrence, an integer selected from 2 to 8;
y is, independently for each occurrence, an integer selected from 2 to 8;
n is 0;
R 1 is an unsubstituted C 1 -C 20 alkyl that is saturated or unsaturated, and branched or unbranched; and
R 2 is hydrogen,
wherein each fatty acid chain residue of the compound is unsubstituted; and

at least one additive.

14. The composition of claim 13 , wherein the at least one additive is selected from an antioxidant, a surfactant, and a stability enhancer.

15. A composition comprising at least one compound of claim 1 , and at least one additive.

16. The composition of claim 15 , wherein the at least one additive selected from an antioxidant, a surfactant, or a stability enhancer.

17. A composition comprising at least one compound of claim 6 , and at least one additive.

18. The composition of claim 17 , wherein the at least one additive selected from an antioxidant, a surfactant, or a stability enhancer.

19. A method comprising:
providing first estolide compound of Formula I:

wherein
x is, independently for each occurrence, an integer selected from 2 to 8;
y is, independently for each occurrence, an integer selected from 2 to 8;
n is 0;
R 1 is an unsubstituted C 1 -C 20 alkyl that is saturated or unsaturated, and branched or unbranched; and
R 2 is hydrogen,
wherein each fatty acid chain residue of the compound is unsubstituted; and

resolving the first estolide compound to provide a second estolide compound having optical activity.

20. The method of claim 19 , wherein the first estolide compound comprises a racemate.

21. The method of claim 20 , wherein the second estolide compound is enantiomerically pure.

22. The method of claim 20 , wherein resolving the first estolide compound comprises the use of chiral chromatography.

23. The composition of claim 11 , wherein the at least one additive selected from an antioxidant, a surfactant, or a stability enhancer.

Assignees

• Biosynthetic Technologies Llc

Inventors

• Forest Jeremy
• Bredsguard Jakob
• Thompson Travis

Classifications

• C10N2040/20

  Metal working · CPC title

• C10N2020/02

  Viscosity; Viscosity index · CPC title

• C10N2020/105

  Containing Ammonia · CPC title

• C10N2020/106

  Containing Carbon dioxide · CPC title

• C10N2020/103

  Containing Hydrocarbons · CPC title