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