Processes for preparing estolide base oils and oligomeric compounds that include cross metathesis
Provided herein are estolide base oils and oligomeric compounds prepared from processes that include cross metathesis. Exemplary processes include the preparation of terminally-unsaturated fatty acids by cross metathesis, and the subsequent oligomerization of terminally-unsaturated fatty acids to provide estolide compounds, such as the process set forth below:
1. At least one compound according to Formula III:
wherein
n is an integer selected from 0 to 20;
R 1 is an unsubstituted, branched or unbranched C 7 to C 17 alkyl that is saturated or unsaturated;
R 2 is hydrogen; and
R 3 and R 4 , independently for each occurrence, are selected from
wherein R 3 and R 4 are unsubstituted and z is 7.
2. The at least one compound according to claim 1 , wherein R 1 is selected from the structure of Formula IV:
wherein w is an integer selected from 5 to 7.
3. The at least one compound according to claim 2 , wherein w is 7.
4. The at least one compound according to claim 1 , wherein R 1 is saturated and unbranched.
5. The at least one compound according to claim 1 , wherein n is an integer selected from 1 to 20.
6. At least one compound according to Formula III:
wherein
n is an integer selected from 1 to 20;
R 1 is an unsubstituted, branched or unbranched C 1 to C 22 alkyl that is saturated or unsaturated;
R 2 is an unsubstituted, branched or unbranched C 1 to C 22 alkyl that is saturated or unsaturated; and
R 3 and R 4 , independently for each occurrence, are selected from
wherein R 3 and R 4 are unsubstituted and z is, independently for each occurrence, an integer selected from 7 and 8.
7. The at least one compound according to claim 6 , wherein R 1 is selected from the structure of Formula IV:
wherein w is an integer selected from 0 to 13.
8. The at least one compound according to claim 7 , wherein w is an integer selected from 5 to 7.
9. The at least one compound according to claim 8 , wherein w is 7.
10. The at least one compound according to claim 6 , wherein R 1 is saturated and unbranched.
11. The at least one compound according to claim 6 , wherein z is 7.
12. The at least one compound according to claim 11 , wherein R 1 is an unsubstituted, branched or unbranched C 7 to C 17 alkyl that is saturated or unsaturated.
13. The at least one compound according to claim 12 , wherein R 1 is saturated and unbranched.
14. The at least one compound according to claim 13 , wherein R 1 is a C 9 alkyl.
15. The at least one compound according to claim 6 , wherein z is 8.
16. The at least one compound according to claim 15 , wherein R 1 is an unsubstituted, branched or unbranched C 7 to C 17 alkyl that is saturated or unsaturated.
17. The at least one compound according to claim 16 , wherein R 1 is saturated and unbranched.
18. The at least one compound according to claim 17 , wherein R 1 is a C 10 alkyl.
19. The at least one compound according to claim 6 , wherein R 2 is a branched C 6 to C 12 alkyl that is saturated.
20. At least one compound according to Formula III:
wherein
n is an integer selected from 0 to 20;
R 1 is an unsubstituted, branched or unbranched C 7 to C 17 alkyl that is saturated or unsaturated;
R 2 is an unsubstituted, branched or unbranched C 1 to C 22 alkyl that is saturated or unsaturated; and
R 3 and R 4 , independently for each occurrence, are selected from
wherein R 3 and R 4 are unsubstituted and z is 8.
21. The at least one compound according to claim 20 , wherein R 1 is a C 7 to C 17 alkyl having at least one terminal site of unsaturation.
22. The at least one compound according to claim 21 , wherein R 1 is a C 10 alkyl.
23. The at least one compound according to claim 20 , wherein R 1 is saturated and unbranched.
24. The at least one compound according to claim 20 , wherein n is 0.
25. The at least one compound according to claim 20 , wherein n is 1.
26. The at least one compound according to claim 20 , wherein R 2 is a branched C 6 to C 12 alkyl that is saturated.
27. A composition comprising:
an additive selected from at least one of a polyalphaolefin, a polyalkylene glycol, a mineral oil, a pour point depressant, a viscosity modifier, an anti-corrosive agent, an antiwear agent, a detergent, an antifoaming agent, or a demulsifier; and
at least one compound selected from compounds of Formula III:
wherein
n is an integer selected from 0 to 20;
R 1 is an unsubstituted, branched or unbranched C 1 to C 22 alkyl that is saturated or unsaturated;
R 2 is selected from hydrogen and an unsubstituted, branched or unbranched C 1 to C 22 alkyl that is saturated or unsaturated; and
R 3 and R 4 , independently for each occurrence, are selected from
wherein R 3 and R 4 are unsubstituted and z is, independently for each occurrence, an integer selected from 7 and 8.
28. The composition according to claim 27 , wherein R 1 is a C 7 to C 17 alkyl having at least one terminal site of unsaturation.
29. The composition according to claim 28 , wherein R 1 is a C 9 alkyl.
30. The composition according to claim 28 , wherein R 1 is a C 10 alkyl.
31. The composition according to claim 27 , wherein R 1 is saturated and unbranched.
32. The composition according to claim 27 , wherein R 1 is an unsubstituted, branched or unbranched C 7 to C 17 alkyl that is saturated.
33. The composition according to claim 27 , R 2 is an unsubstituted, branched or unbranched C 1 to C 22 alkyl that is saturated or unsaturated.
34. The composition according to claim 27 , wherein R 2 is a branched C 6 to C 12 alkyl that is saturated.
35. The composition according to claim 27 , wherein n is 0.
36. The composition according to claim 27 , wherein n is 1.
37. The composition according to claim 33 , wherein R 2 is saturated.