Conversion of oligomeric starch, cellulose, hydrolysates or sugars to hydrocarbons

Patent metadata

Field	Value
Publication number	US-9751815-B2
Application number	US-201615284378-A
Country	US
Kind code	B2
Filing date	Oct 3, 2016
Priority date	Jul 10, 2012
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

Embodiments of the present invention are directed to the conversion of a source material (e.g., a depolymerized oligosaccharide mixture, a monomeric sugar, a hydrolysate, or a mixture of monomeric sugars) to intermediate molecules containing 7 to 26 contiguous carbon atoms. These intermediates may also be converted to saturated hydrocarbons. Such saturated hydrocarbons are useful as, for example, fuels.

First claim

What is claimed is:

1. A process of preparing a saturated hydrocarbon comprising:
combining a source material with a dicarbonyl under conditions suitable to form an intermediate mixture, the source material comprising a depolymerized oligosaccharide mixture, a monomeric sugar, a hydrolysate, or a mixture of monomeric sugars; and
adding hydrogen and a hydrogenation catalyst to the intermediate mixture under conditions suitable to form the saturated hydrocarbon.

2. The process of claim 1 , wherein the dicarbonyl is methyl acetoacetate, ethyl acetoacetate, i-propyl acetoacetate, 2,4-pentanedione, n-propyl acetoacetate, malonate esters, cyanoacetates, or a mixture thereof.

3. The process of claim 2 , wherein the dicarbonyl is 2,4-pentanedione.

4. The process of claim 1 , wherein the saturated hydrocarbon is 3-ethylnonane.

5. The process of claim 1 , wherein the hydrogenation catalyst is palladium/carbon or nickel.

6. The process of claim 1 , wherein the source material comprises a depolymerized oligosaccharide mixture, and the depolymerized oligosaccharide mixture is prepared by heating an oligosaccharide for a time sufficient to form the depolymerized oligosaccharide mixture.

7. The process of claim 6 , wherein the heating is achieved using microwave radiation.

8. The process of claim 6 , wherein the heating of the oligosaccharide to form the depolymerized oligosaccharide mixture is under acidic conditions.

9. The process of claim 8 , wherein the acidic conditions are achieved using hydrochloric acid, triflic acid, acetic acid, trifluoroacetic acid, or a combination thereof.

10. The process of claim 6 , wherein the heating of the oligosaccharide to form the depolymerized oligosaccharide mixture is conducted in the presence of a Lewis acid catalyst or a Bronsted acid catalyst.

11. The process of claim 10 , wherein the Lewis acid catalyst or the Bronsted acid catalyst is cerium chloride, iron chloride, lanthanum triflate, iron triflate, or a mixture thereof.

12. The process of claim 1 , wherein the combining of the source material with the dicarbonyl is conducted in the presence of a Lewis acid catalyst or a Bronsted acid catalyst.

13. The process of claim 12 , wherein the Lewis acid catalyst or the Bronsted acid catalyst is cerium chloride, iron chloride, lanthanum triflate, iron triflate, or a mixture thereof.

14. The process of claim 1 , wherein the source material comprises a hydrolysate, the hydrolysate comprising a mixture of two or more sugars.

15. The process of claim 14 , wherein the mixture of two or more sugars comprises a mixture of two or more of glucose, xylose, arabinose, cellobiose, galactose and/or fructose.

16. The process of claim 14 , wherein the hydrolysate further comprises one or more acids.

17. The process of claim 16 , wherein the one or more acids comprises one or more of lactic acid, glycerol, ethanol, acetic acid, ethanol, furfural and/or hydroxymethylfurfural (HMF).

18. The process of claim 1 , wherein the monomeric sugar comprises glucose or xylose.

19. The process of claim 1 , wherein the mixture of monomeric sugars comprises at least glucose and xylose.

Assignees

• Los Alamos Nat Security Llc

Inventors

• Silks Louis A
• Sutton Andrew
• Kim Jin Kyung
• Gordon John Cameron
• Wu Ruilian
• Kimball David B

Classifications

• C07D407/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07C2523/755

  Nickel · CPC title

• C07C2521/18

  Carbon · CPC title

• C07C1/2076 Primary

  by a transformation in which at least one -C(=O)- moiety is eliminated · CPC title

• C07C2523/44

  Palladium · CPC title