Hydroxy estolides, poly-capped estolides, and methods of making the same
Provided herein are poly-capped estolides, including those of the Formula IV in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 2; R 1 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. Hydroxy estolides are also described herein, which may be suitable end products, or serve as intermediates to provide poly-capped estolides. Also provided are compositions containing poly-capped estolides and methods of making both said poly-capped estolides and compositions thereof.
1. At least one compound according to Formula VI:
wherein
z is an integer selected from 7 and 8;
p is 0;
q is 0;
R 5 and R 6 are independently selected from —C(O)R 1 and an unsubstituted alkyl that is saturated or unsaturated, and branched or unbranched;
R 1 is an unsubstituted alkyl that is saturated or unsaturated, and branched or unbranched; and
R 2 is selected from unsubstituted alkyl that is saturated or unsaturated, and branched or unbranched, and a substituent represented by Formula II:
wherein
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 0 to 20;
R 3 is selected from hydrogen and unsubstituted alkyl that is saturated or unsaturated, and branched or unbranched;
W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , and W 7 , independently for each occurrence, are selected from —CH 2 — and —CH═CH—; and
Q 1 , Q 2 , and Q 3 , independently for each occurrence, are selected from hydrogen and —CH 3 ,
wherein each fatty acid chain residue of said at least one compound is unsubstituted.
2. The at least one compound according to claim 1 , wherein R 5 and R 6 are independently selected from —C(O)R 1 .
3. The at least one compound according to claim 2 , wherein R 1 , independently for each occurrence, is selected from an unsubstituted C 1 to C 18 alkyl that is saturated or unsaturated, and branched or unbranched.
4. The at least one compound according to claim 2 , wherein R 1 , independently for each occurrence, is selected from C 5 to C 11 alkyl.
5. The at least one compound according to claim 3 , wherein R 1 is saturated and unbranched for each occurrence.
6. The at least one compound according to claim 1 , wherein R 5 and R 6 are independently selected from C 1 -C 10 alkyl.
7. The at least one compound according to claim 1 , wherein W 3 , W 5 , and W 7 for each occurrence are —CH 2 —.
8. The at least one compound according to claim 7 , wherein W 4 and W 6 for each occurrence are —CH 2 —.
9. The at least one compound according to claim 1 , wherein z is 7.
10. The at least one compound according to claim 1 , wherein R 2 is a substituent represented by Formula II:
11. The at least one compound according to claim 10 , wherein R 3 is selected from optionally substituted C 1 to C 20 alkyl that is saturated or unsaturated and branched or unbranched.
12. The at least one compound according to claim 1 , wherein Q 1 is hydrogen.
13. The at least one compound according to claim 1 , wherein W 3 is —CH 2 — for each occurrence.
14. The at least one compound according to claim 1 , wherein z is 8.
15. The at least one compound according to claim 1 , wherein R 2 is an unsubstituted C 1 -C 18 alkyl that is saturated or unsaturated, and branched or unbranched.
16. The at least one compound according to claim 15 , wherein R 2 is saturated.
17. The at least one compound according to claim 16 , wherein R 2 is an unsubstituted C 6 to C 12 alkyl that is branched.
18. The at least one compound according to claim 13 , wherein R 2 is an unsubstituted C 1 -C 18 alkyl that is saturated or unsaturated, and branched or unbranched.
19. The at least one compound according to claim 18 , wherein Q 1 is hydrogen.