# US 10,118,883 B2 · Method for producing levulinic acid from lignocellulosic biomass

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- Number: US 10,118,883 B2
- Document ID: US10118883B2
- Status: Granted
- Kind: B2
- Application number: 14/384,548
- Filed: 2013-03-11
- Published: 2015-02-26
- Granted: 2018-11-06
- Earliest claimed: 2012-03-12
- Assignees: Georgia-Pacific Corporation
- Applicants: Georgia-Pacific LLC
- Inventors: William A. Frey; Jeffrey Wayne Brown; John Patrick Kelly; Michael Eugene Carroll; Peter Chester Guion
- Web page: https://patentgrep.com/patent/US10118883B2

## CPC

- C07C 51/00: Preparation of carboxylic acids or their salts, halides or anhydrides (of acids by hydrolysis of oils, fats or waxes C11C)
- C07C 51/42: Separation; Purification; Stabilisation; Use of additives
- C10L 5/403: {on paper and paper waste}
- D21C 3/022: {in presence of S-containing compounds}
- F23G 7/00: Incinerators or other apparatus for consuming industrial waste, e.g. chemicals (incinerator closets A47K11/02; oxidation of sludge C02F11/06; burners in general, burner details F23D; incinerating radioactive waste G21F9/00)
- C10L 2290/08: Drying or removing water
- Y02E 20/12: Heat utilisation in combustion or incineration of waste
- Y02E 50/10: Biofuels, e.g. bio-diesel
- Y02E 50/30: Fuel from waste, e.g. synthetic alcohol or diesel
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- D21C: PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- F23G: CREMATION FURNACES; CONSUMING WASTE PRODUCTS BY COMBUSTION
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A method for producing levulinic acid from lignocellulosic biomass comprising hemicellulose including one or more six carbon chain compound precursors comprises the steps of hydrolyzing the lignocellulosic biomass to form a first phase comprising partially hydrolyzed lignocellulosic biomass including cellulose and lignin and a second phase comprising one or more five carbon chain sugars and one or more six carbon chain sugars from degradation of the hemicellulose, separating the first phase from the second phase, and converting at least a portion of the one or more six carbon chain sugars to levulinic acid.

## Claims

### Claim 1

A method for producing levulinic acid from lignocellulosic biomass comprising hemicellulose including one or more six carbon chain compound precursors, the method comprising the steps of:
hydrolyzing the lignocellulosic biomass in a reactor at a temperature of about 170° C. to about 185° C. for about 35 minutes to about 60 minutes to form a first phase comprising partially hydrolyzed lignocellulosic biomass including cellulose and lignin and a second phase comprising one or more five carbon chain sugars and one or more six carbon chain sugars from degradation of the hemicellulose, wherein the hydrolyzing comprises contacting the lignocellulosic biomass with at least one acid, wherein the acid is present in an amount of up to 10 percent, by weight, of the lignocellulosic biomass;
separating the first phase from the second phase; and
converting at least a portion of the one or more five carbon chain sugars to furfural, a furfural reaction intermediate, tar, or a combination thereof in the presence of the one or more six carbon chain sugars, by contacting the one or more five carbon chain sugars with at least one acid, wherein the acid is present in an amount of up to 10 percent, by weight, of the reactor contents; and
separating at least a portion of the furfural, the furfural reaction intermediate, the tar, or the combination thereof from the one or more six carbon chain sugars, and thereafter
converting at least a portion of the one or more six carbon chain sugars to levulinic acid in a reactor at a temperature of about 190° C. to about 220° C. for a period of 20 minutes to 60 minutes.

### Claim 2 (depends on 1)

The method of claim 1 wherein the step of hydrolyzing the lignocellulosic biomass further comprises contacting the lignocellulosic biomass with steam, alcohol, or both.

### Claim 3 (depends on 1)

The method of claim 1 wherein the first phase further comprises one or more six carbon chain sugars or one or more six carbon chain sugar precursors and the method further comprises converting the at least a portion of the one or more six carbon chain sugars or one or more six carbon chain sugar precursors from the first phase to levulinic acid.

### Claim 4 (depends on 1)

The method of claim 1 wherein the second phase is liquid.

### Claim 5 (depends on 1)

The method of claim 1 wherein the second phase further comprises a solvent and the method further comprises the steps of separating at least a portion of the solvent from the second phase before the step of converting at least a portion of the one or more five carbon chain sugars to furfural, a furfural reaction intermediate, tar, or a combination thereof, and recycling the at least a portion of the solvent from the second phase for use in the step of hydrolyzing the lignocellulosic biomass.

### Claim 6 (depends on 1)

The method of claim 1 wherein the step of converting at least a portion of the one or more five carbon chain sugars to furfural, a furfural reaction intermediate, tar, or a combination thereof is carried out in a reactor at a temperature of about 130° C. to about 300° C. for about 35 minutes to about 60 minutes.

### Claim 7 (depends on 1)

The method of claim 1 wherein separating at least a portion of the furfural from the one or more six carbon chain sugars comprises introducing the mixture of furfural and the one or more six carbon chain sugars into a flash evaporator.

### Claim 8 (depends on 1)

The method of claim 1 wherein the step of converting at least a portion of the one or more six carbon chain sugars to levulinic acid comprises contacting the one or more six carbon chain sugars with at least one acid.

### Claim 9 (depends on 1)

The method of claim 1 wherein the step of converting at least a portion of the one or more six carbon chain sugars to levulinic acid also converts at least another portion of the one or more six carbon chain sugars to formic acid and char.

### Claim 10 (depends on 1)

The method of claim 1 further comprising converting at least a portion of the first phase to a wood pulp product.

### Claim 11 (depends on 10)

The method of claim 10 wherein the wood pulp product is pulp.

### Claim 12 (depends on 11)

The method of claim 11 wherein the step of converting at least a portion of the first phase to the pulp comprises converting the at least a portion of the first phase to pulp in a Kraft pulp making process.

### Claim 13 (depends on 10)

The method of claim 10 wherein the wood pulp product is fuel and the step of converting at least a portion of the first phase to the wood pulp product comprises drying the at least a portion of the first phase.

### Claim 14 (depends on 10)

The method of claim 10 wherein the wood pulp product is fuel and the step of converting at least a portion of the first phase to the wood pulp product comprises combusting the at least a portion of the first phase.

### Claim 15 (depends on 10)

The method of claim 10 wherein the wood pulp product is wood pellets or dissolving pulp.

### Claim 16 (depends on 10)

The method of claim 10 further comprising the steps of separating the five carbon chain sugars from the six carbon chain sugars and combining the five carbon chain sugars with the wood pulp product.
