# US 2014/0194619 A1 · Method to produce water-soluble sugars from biomass using solvents containing lactones

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- Number: US 2014/0194619 A1
- Document ID: US20140194619A1
- Status: Published application
- Kind: A1
- Application number: 13/736,550
- Filed: 2013-01-08
- Published: 2014-07-10
- Earliest claimed: 2013-01-08
- Assignees: Wisconsin Alumni Research Foundation
- Applicants: Wisconsin Alumni Research Foundation
- Inventors: James A. Dumesic; Jeremy S. Luterbacher
- Web page: https://patentgrep.com/patent/US20140194619A1

## CPC

- C13K 1/02: obtained by saccharification of cellulosic materials (manufacture of fodder A23K10/32)
- C07D 307/46: Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D 307/50: Preparation from natural products
- C07H 3/06: Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
- C13K 1/00: Glucose (separation from invert sugar C13K3/00); Glucose-containing syrups
- C13K 1/06: obtained by saccharification of starch or raw materials containing starch
- C13K 13/002: {Xylose}
- Y02E 50/10: Biofuels, e.g. bio-diesel
- C13K: SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES (chemically synthesised sugars or sugar derivatives C07H; polysaccharides, e.g. starch, derivatives thereof C08B; malt C12C; fermentation or enzyme-using processes for preparing compounds containing saccharide radicals C12P19/00; production of sucrose C13B)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A process to produce an aqueous solution of carbohydrates that contains C6-sugar-containing oligomers, C6 sugar monomers, C5-sugar-containing oligomers, C5 sugar monomers, or any combination thereof is presented. The process includes the steps of reacting biomass or a biomass-derived reactant with a solvent system including a lactone and water, and an acid catalyst. The reaction yields a product mixture containing water-soluble C6-sugar-containing oligomers, C6-sugar monomers, C5-sugar-containing oligomers, C5-sugar monomers, or any combination thereof. A solute is added to the product mixture to cause partitioning of the product mixture into an aqueous layer containing the carbohydrates and a substantially immiscible organic layer containing the lactone.

## Claims

### Claim 1

A process to produce an aqueous solution of carbohydrates comprising C6-sugar-containing oligomers, C6-sugar monomers, C5-sugar-containing oligomers, C5-sugar monomers, or any combination thereof, the process comprising:
(a) reacting biomass or a biomass-derived reactant with a solvent system comprising (i) an organic solvent selected from the group consisting of beta-, gamma-, and delta-lactones, and combinations thereof, and (ii) at least about 1 wt % water; in the presence of an acid catalyst for a time and under conditions to yield a product mixture wherein at least a portion of water-insoluble C6-sugar-containing polymers or oligomers, or water-insoluble C5-sugar-containing polymers or oligomers, if present in the biomass or biomass-derived reactant, are converted to water-soluble C6-sugar-containing oligomers, C6-sugar monomers, C5-sugar-containing oligomers, C5-sugar monomers, or any combination thereof; and then
(b) adding a solute to the product mixture of step (a) in an amount sufficient to cause partitioning of the product mixture into an aqueous layer and a substantially immiscible organic layer.

### Claim 2 (depends on 1)

The method of claim 1, wherein the organic solvent is miscible with water.

### Claim 3 (depends on 1)

The method of claim 1, wherein the organic solvent can dissolve from 2 wt % to 40 wt % water.

### Claim 4 (depends on 1)

The method of claim 1, wherein the organic solvent is gamma-valerolactone (GVL).

### Claim 5 (depends on 1)

The method of claim 1, wherein the organic solvent is present in a mass ratio with water, organic solvent:water, selected from the group consisting of about 60:40, about 65:35, about 70:30, about 75:25, about 80:20, about 85:15, about 90:10, about 95:5, about 97:3, about 98:2, and about 99:1.

### Claim 6 (depends on 1)

The method of claim 1, wherein the acid catalyst is homogeneous or heterogeneous, and if the acid catalyst is homogeneous it is present in a concentration not greater than 100 mM based on volume of the solvent system, and if the acid catalyst is heterogeneous it is present in a concentration not greater than 1.0 wt % based on weight of the solvent system.

### Claim 7 (depends on 6)

The method of claim 6, wherein the acid catalyst is a mineral acid or an organic acid.

### Claim 8 (depends on 6)

The method of claim 6, wherein the acid catalyst is a solid acid catalyst selected from the group consisting of solid Brønsted acid catalysts, solid Lewis acid catalysts, and combinations thereof.

### Claim 9 (depends on 8)

The method of claim 8, wherein the solid acid catalyst is a heteropolyacid.

### Claim 10 (depends on 8)

The method of claim 8, wherein the solid acid catalyst is an amorphous or mesoporous silica, which may be unfunctionalized or functionalized with acidic modifier.

### Claim 11 (depends on 8)

The method of claim 8, wherein the solid acid catalyst is a zeolite.

### Claim 12 (depends on 1)

The method of claim 1, wherein the solute is a water-soluble, inorganic salt.

### Claim 13 (depends on 12)

The method of claim 12, wherein the salt is added to the product mixture in a saturating amount.

### Claim 14 (depends on 12)

The method of claim 12, wherein the salt is sodium chloride.

### Claim 15 (depends on 1)

The method of claim 1, wherein step (a) is conducted at a temperature range selected from the group consisting of from about 100° C. to about 300° C., about 140° C. to about 240° C., and about 150° C. to about 200° C.

### Claim 16 (depends on 1)

The method of claim 1, wherein step (a) is conducted at a dynamic temperature range.

### Claim 17 (depends on 16)

The method of claim 16, wherein the dynamic temperature range ramps from a first temperature to a second temperature that is higher than the first temperature.

### Claim 18 (depends on 16)

The method of claim 16, wherein the dynamic temperature range changes from a first temperature to a second temperature in a non-linear fashion, a discontinuous fashion or a combination thereof.

### Claim 19 (depends on 1)

The method of claim 1, wherein in step (a) the biomass or a biomass-derived reactant comprises water-insoluble glucose-containing polymers or oligomers, or water-insoluble xylose-containing polymers or oligomers, or any combination thereof, and these, if present, are converted to water-soluble glucose-containing oligomers, glucose monomers, water-soluble xylose-containing oligomers, xylose monomers, or any combination thereof.

### Claim 20 (depends on 1)

The method of claim 1, wherein in step (a), residence time of the reaction is selected from the group consisting of 1 min to 24 hours, 1 min to 20 hours, 1 min to 12 hours, 1 min to 6 hours, 1 min to 3 hours, 1 min to 2 hours, 1 min to 1 hour, and 1 min to 30 min.