IP Library Granted Patent US 9,045,804
Granted Patent B2
US 9,045,804 · App. 13/736,550 · Granted Jun 2, 2015

Method to produce water-soluble sugars from biomass using solvents containing lactones

Inventors: James A. Dumesic (Verona, WI); Jeremy S. Luterbacher (Madison, WI)
Assignee: Wisconsin Alumni Research Foundation
C13K1/02C13K1/06C13K13/002
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Quick Facts
Patent No.
US 9,045,804
App. No.
13/736,550
Granted
Jun 2, 2015
Kind
B2
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 (22)

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.

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

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

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

5. The process 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.

6. The process 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.

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

8. The process 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.

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

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

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

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

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

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

15. The process 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.

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

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

18. The process 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.

19. The process 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.

20. The process 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.

Assignments (3)
CONFIRMATORY LICENSE Recorded Apr 10, 2018
From: UNIVERSITY OF WISCONSIN-MADISON
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 045913/0391 →
CONFIRMATORY LICENSE Recorded Dec 6, 2013
From: WISCONSIN ALUMNI RESEARCH FOUNDATION
To: ENERGY, UNITED STATES DEPARTMENT OF
Reel/Frame 031946/0699 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2013
From: DUMESIC, JAMES; LUTERBACHER, JEREMY
To: WISCONSIN ALUMNI RESEARCH FOUNDATION
Reel/Frame 029749/0586 →
Continuity (1)
Related Publication 20140194619A1 · Jul 10, 2014