IP Library Granted Patent US 10,532,990
Granted Patent B2
US 10,532,990 · App. 15/527,597 · Granted Jan 14, 2020

Methods for converting cellulose to furanic products

Inventors: Robert Jansen (Collinsville, IL); James Alan Lawson (Ellsworth, ME); Philip Travisano (Danville, VA); Brendon Christopher Stout (Burlington, NC); Allison Jean Hulchanski (Chapel Hill, NC); Neta Matis (Danville, VA); Noa Lapidot (Mevaserat Zion, IL); Michael Zviely (Haifa, IL); Adam Tyler Carden (Henderson, NC); Michael Andrew Faison (Danville, VA); Bassem Hallac (Jersualem, IL); Sterling Alexander White (Rocky Mount, VA)
Assignee: VIRDIA, INC.
C07D307/50C07D233/58C13K1/04C13K11/00
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Quick Facts
Patent No.
US 10,532,990
App. No.
15/527,597
Granted
Jan 14, 2020
Kind
B2
Abstract

The present invention relates to systems, methods, and processes for the production of conversion products such as furanic products from biomass such as lignocellulosic materials.

Claims (30)

1. A process for conversion of cellulose pulp to hydroxymethyl furfural, the process comprising:

separating a lignin-depleted hydrolysate stream comprising glucose, hydroxymethyl furfural, an organic acid, and water to thereby produce:

a first stream comprising the hydroxymethyl furfural, the organic acid, and water; and

a second stream comprising the glucose and water;

isomerizing the glucose in the second stream to thereby produce a fructose stream;

dehydrating fructose in the fructose stream to thereby produce a reaction product comprising hydroxymethyl furfural: and

recycling the reaction product, the recycling comprising introducing the reaction product from the dehydrating step to the separating step.

2. The process of claim 1 , wherein the separating further produces a third stream comprising water and cellobiose.

3. The process of claim 1 , wherein the lignin-depleted hydrolysate stream further comprises sodium ions, wherein the sodium ions are present in an amount not greater than 5% weight/weight.

4. The process of claim 1 , wherein the concentration of the glucose in the lignin-depleted hydrolysate stream is ≥6% weight/weight.

5. The process of claim 1 , wherein the concentration of the hydroxymethyl furfural in the lignin-depleted hydrolysate stream is ≤3% weight/weight.

6. The process of claim 1 , wherein the separating comprises simulated moving bed chromatography or sequential simulated moving bed chromatography.

7. The process of claim 6 , wherein the separating comprises a strong acid cation exchange resin.

8. The process of claim 1 , wherein the isomerizing comprising increasing the pH to at least 8.

9. The process of claim 8 , wherein the increasing the pH comprises adding an ionic liquid in hydroxide form.

10. The process of claim 1 , wherein the isomerizing comprises 0.5 to 10 hours of stirring at a temperature between 45 to 80° C.

11. The process of claim 1 , wherein the dehydrating comprises a strong acid cation resin.

12. The process of claim 11 , wherein the strong acid cation resin is a macroporous strong acid cation resin.

13. The process of claim 1 , wherein the fructose stream comprises fructose and glucose.

14. The process of claim 13 , wherein the dehydrating comprises converting at least 50% of the fructose to hydroxymethyl furfural, wherein at least 60% of the glucose is not converted to hydroxymethyl furfural.

15. The process of claim 13 , wherein the fructose stream comprises 4-10% glucose weight/weight and 1-4% fructose weight/weight.

16. The process of claim 1 , wherein the reaction product comprises 3-10% glucose weight/weight, ≤0.2% fructose weight/weight, and 1-3% hydroxymethyl furfural weight/weight.

17. The process of claim 1 , further comprising capturing the hydroxymethyl furfural from the first stream, the capturing comprising adsorbing on a non-functional polymeric resin the hydroxymethyl furfural from the first stream.

18. The process of claim 17 , further comprising recovering the captured hydroxymethyl furfural, the recovering comprising solvent desorption.

19. The process of claim 17 , wherein the capturing further comprises controlling the pH of the reaction product to be above the pKa of the organic acid.

20. The process of claim 17 , further comprising increasing the pH of the first stream prior to the capturing.

21. The process of claim 20 , wherein the increasing the pH comprises adding an ionic liquid in hydroxide form.

22. The process of claim 18 , wherein the solvent desorption comprises addition of a solution of a solvent and water to the non-functional polymeric resin.

23. The process of claim 22 , wherein the solvent is selected from ethyl acetate, methanol, ethanol, isopropanol, 1-butanol, 2-butanol, and combinations thereof.

24. The process of claim 1 , wherein the first stream comprises ≤5% weight/weight hydroxymethyl furfural.

Assignments (2)
CHANGE OF NAME Recorded Mar 18, 2021
From: VIRDIA, INC.
To: VIRDIA, LLC
Reel/Frame 055633/0305 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 18, 2017
From: JANSEN, ROBERT; LAWSON, JAMES ALAN; TRAVISANO, PHILIP; STOUT, BRENDON; HULCHANSKI, ALLISON JEAN; MATIS, NETA; LAPIDOT, NOA; ZVIELY, MICHAEL; CARDEN, ADAM TYLER; FAISON, MICHAEL ANDREW; HALLAC, BASSEM; WHITE, STERLING ALEXANDER
To: VIRDIA, INC.
Reel/Frame 043614/0499 →