Compounds and methods for the production of long chain hydrocarbons from biological sources
The present invention is directed to the preparation of oxygenated, unsaturated hydrocarbon compounds, such as derivatives of furfural or hydroxymethyl furfural produced by aldol condensation with a ketone or a ketoester, as well as methods of deoxidatively reducing those compounds with hydrogen under acidic conditions to provide saturated hydrocarbons useful as fuels.
1. A compound of formula I:
wherein
R 1 is H or C 1-6 alkyl;
each R 2 is independently hydrogen or C 1-6 alkyl;
R 3 is H or C 1-6 alkyl;
R 4 is C 1-6 alkyl or substituted C 1-6 alkyl;
n is 1, 2, 3, or 4; and
m is 1, 2, 3, or 4.
2. The compound of claim 1 , wherein R 1 is H.
3. The compound of claim 1 , wherein R 1 is methyl or ethyl.
4. The compound of claim 1 , wherein each R 2 is hydrogen.
5. The compound of claim 1 , wherein R 4 is substituted C 1-6 alkyl.
6. The compound of claim 5 , wherein R 4 is —CH 2 —OH.
7. The compound of claim 1 , wherein R 1 is C 1-3 alkyl.
8. The compound of claim 1 , wherein R 1 is C 1-4 alkyl.
9. The compound of claim 1 , wherein R 2 is C 1-4 alkyl.
10. The compound of claim 1 , wherein R 2 is C 1-3 alkyl.
11. The compound of claim 1 , wherein R 2 is C 1-2 alkyl.
12. The compound of claim 1 , wherein R 2 is methyl.
13. The compound of claim 1 , wherein R 4 is C 1-4 alkyl or substituted C 1-4 alkyl.
14. The compound of claim 1 , wherein R 4 is C 1-3 alkyl or substituted C 1-3 alkyl.
15. The compound of claim 1 , wherein R 4 is C 1-2 alkyl or substituted C 1-2 alkyl.
16. The compound of claim 1 , wherein R 4 is methyl or substituted methyl.
17. The compound of claim 5 , wherein R 4 is C 1-6 alkyl substituted with —OH.
18. The compound of claim 17 , wherein R 4 is —CH 2 —OH or —CH 2 —CH 2 —OH.
19. The compound of claim 5 , wherein R 4 is C 1-6 alkyl substituted with oxo or —COOH.
20. A compound of formula I:
wherein:
R 1 is H or C 1-6 alkyl;
each R 2 is independently hydrogen or C 1-6 alkyl;
R 3 is H or C 1-6 alkyl;
R 4 is H, C 1-6 alkyl, or substituted C 1-6 alkyl;
n is 2, 3, or 4; and
m is 1, 2, 3, or 4,
with the proviso that when R 1 is H, R 4 is C 1-6 alkyl or substituted C 1-6 alkyl.
21. The compound of claim 20 , wherein R 1 is H.
22. The compound of claim 20 , wherein R 1 is methyl or ethyl.
23. The compound of claim 20 , wherein R 1 is C 1-3 alkyl.
24. The compound of claim 20 , wherein R 1 is C 1-4 alkyl.
25. The compound of claim 20 , wherein each R 2 is hydrogen.
26. The compound of claim 20 , wherein R 2 is C 1-4 alkyl.
27. The compound of claim 20 , wherein R 2 is C 1-3 alkyl.
28. The compound of claim 20 , wherein R 2 is C 1-2 alkyl.
29. The compound of claim 20 , wherein R 2 is methyl.
30. The compound of claim 20 , wherein R 4 is hydrogen.
31. The compound of claim 20 , wherein R 4 is substituted C 1-6 alkyl.
32. The compound of claim 20 , wherein R 4 is C 1-6 alkyl substituted with —OH.
33. The compound of claim 32 , wherein R 4 is —CH 2 —OH or —CH 2 —CH 2 —OH.
34. The compound of claim 20 , wherein R 4 is C 1-4 alkyl or substituted C 1-4 alkyl.
35. The compound of claim 20 , wherein R 4 is C 1-3 alkyl or substituted C 1-3 alkyl.
36. The compound of claim 20 , wherein R 4 is C 1-2 alkyl or substituted C 1-2 alkyl.
37. The compound of claim 20 , wherein R 4 is methyl or substituted methyl.
38. The compound of claim 31 , wherein R 4 is C 1-6 alkyl substituted with oxo or —COOH.