Conversion of oligomeric starch, cellulose, or sugars to hydrocarbons

Patent metadata

Field	Value
Publication number	US-9469574-B2
Application number	US-201214413552-A
Country	US
Kind code	B2
Filing date	Sep 14, 2012
Priority date	Jul 10, 2012
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

The present invention is directed to the one step selective conversion of starch, cellulose, or glucose to molecules containing 7 to 26 contiguous carbon atoms. The invention is also directed to the conversion of those intermediates to saturated hydrocarbons. Such saturated hydrocarbons are useful as, for example, fuels.

First claim

What is claimed:

1. A process of preparing a saturated hydrocarbon comprising:
heating an oligosaccharide for time sufficient to form a depolymerized oligosaccharide mixture;
combining the depolymerized oligosaccharide mixture with a dicarbonyl under conditions suitable to form an intermediate mixture; 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.

6. The process of claim 1 , wherein the heating is achieved using microwave radiation.

7. The process of claim 1 , wherein the heating of the oligosaccharide to form the depolymerized oligosaccharide mixture is under acidic conditions.

8. The process of claim 7 , wherein the acid conditions are achieved using hydrochloric acid, triflic acid, acetic acid, trifluoroacetic acid, or a combination thereof.

9. The process of claim 1 , wherein the heating of the oligosaccharide to form the depolymerized oligosaccharide mixture is conducted in the presence of a Lewis acid catalyst or a Brønsted acid catalyst.

10. The process of claim 9 , wherein the Lewis acid catalyst or the Brønsted acid catalyst is cerium chloride, iron chloride, lanthanum triflate, iron triflate, or a mixture thereof.

11. The process of claim 1 , wherein the combining of the depolymerized oligosaccharide mixture with the dicarbonyl is conducted in the presence of a Lewis acid catalyst or a Brønsted acid catalyst.

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

Assignees

• Silks Louis A
• Sutton Andrew
• Kim Jin Kyung
• Gordon John Cameron
• Wu Ruilian
• Kimball David B
• Los Alamos Nat Security Llc

Inventors

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

Classifications

• C07D307/46

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

• C07C2531/28

  of the platinum group metals, iron group metals or copper · CPC title

• C07C2521/18

  Carbon · CPC title

• C07C2523/42

  Platinum · CPC title

• C07C1/2076 Primary

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