Compounds and methods for the production of long chain hydrocarbons from biological sources

Patent metadata

Field	Value
Publication number	US-9422207-B2
Application number	US-201214344178-A
Country	US
Kind code	B2
Filing date	Sep 14, 2012
Priority date	Sep 14, 2011
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

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.

First claim

What is claimed:

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.

Assignees

• Gordon John Cameron
• Silks Louis A
• Sutton Andrew D
• Wu Ruilian
• Schlaf Marcel
• Waldie Fraser
• West Ryan
• Collias Dimitris Ioannis
• Los Alamos Nat Security Llc
• Procter & Gamble

Inventors

• Gordon John Cameron
• Silks Louis A
• Sutton Andrew D
• Wu Ruilian
• Schlaf Marcel
• Waldie Fraser
• West Ryan
• Collias Dimitris Ioannis

Classifications

• C07D307/48 Primary

  Furfural · CPC title

• C07D307/46

  Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom · CPC title

• C07C2523/44

  Palladium · CPC title

• C10L2200/04

  Organic compounds · CPC title

• C10L1/04

  essentially based on blends of hydrocarbons · CPC title