# US 9,751,815 B2 · Conversion of oligomeric starch, cellulose, hydrolysates or sugars to hydrocarbons

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- Number: US 9,751,815 B2
- Document ID: US9751815B2
- Status: Granted
- Kind: B2
- Application number: 15/284,378
- Filed: 2016-10-03
- Published: 2017-01-26
- Granted: 2017-09-05
- Earliest claimed: 2012-07-10
- Assignees: Los Alamos National Security, LLC
- Applicants: Los Alamos National Security, LLC
- Inventors: Louis A. Silks; Andrew Sutton; Jin Kyung Kim; John Cameron Gordon; Ruilian Wu; David B. Kimball
- Web page: https://patentgrep.com/patent/US9751815B2

## CPC

- C07C 1/2076: {by a transformation in which at least one -C(=O)- moiety is eliminated}
- C07C 1/20: starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C 5/03: of non-aromatic carbon-to-carbon double bonds
- C07C 45/60: in six-membered rings
- C07D 407/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07C 2521/18: Carbon
- C07C 2523/10: of rare earths
- C07C 2523/44: Palladium
- C07C 2523/745: Iron
- C07C 2523/755: Nickel
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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.

## Claims

### Claim 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 2)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 6)

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

### Claim 8 (depends on 6)

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

### Claim 9 (depends on 8)

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

### Claim 10 (depends on 6)

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.

### Claim 11 (depends on 10)

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.

### Claim 12 (depends on 1)

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.

### Claim 13 (depends on 12)

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.

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 14)

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.

### Claim 16 (depends on 14)

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

### Claim 17 (depends on 16)

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).

### Claim 18 (depends on 1)

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

### Claim 19 (depends on 1)

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