IP Library Granted Patent US 10,752,878
Granted Patent B2
US 10,752,878 · App. 15/933,210 · Granted Aug 25, 2020

Sugar mixtures and methods for production and use thereof

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Quick Facts
Patent No.
US 10,752,878
App. No.
15/933,210
Granted
Aug 25, 2020
Kind
B2
Abstract

A sugar mixture comprising: monosaccharides; oligosaccharides in a ratio≥0.06 to total saccharides; disaccharides in a ratio to total saccharides≥0.05; pentose in a ratio to total saccharides≥0.05; at least one alpha-bonded di-glucose; and at least one beta-bonded di-glucose. Also disclosed are methods to make and/or use such mixtures.

Claims (35)

1. A method comprising:

(a) hydrolyzing a lignocellulosic material in a medium containing a mineral acid to form a hydrolyzate;

(b) de-acidifying the hydrolyzate to form a de-acidified hydrolyzate comprising:

monosaccharides;

a ratio of higher oligosaccharides to total saccharides of≤0.2 weight/weight;

a ratio of pentose to total saccharides of≥0.05 weight/weight;

at least one alpha-bonded di-glucose;

at least one beta-bonded di-glucose; and

a ratio of mineral acid to total saccharides of≤0.03 weight/weight.

2. The method of claim 1 , wherein the hydrolyzing is conducted in a counter-current mode of operation.

3. The method of claim 1 , wherein the hydrolyzing is conducted at a temperature of less than 50° C.

4. The method of claim 1 , wherein the ratio of the mineral acid to total mineral acid and water in the medium is≥0.37 by weight.

5. The method of claim 1 , wherein the mineral acid is HCl.

6. The method of claim 1 , wherein the de-acidifying is conducted at a temperature of less than 80° C.

7. The method of claim 1 , wherein the de-acidifying comprises:

(i) extracting the hydrolyzate with a first extractant comprising an S1 solvent to form a mineral acid-carrying first extract and a mineral acid-depleted sugar solution, and

(ii) removing residual mineral acid in the mineral acid-depleted sugar solution by at least one of:

(ii-a) chromatographic separation, and

(ii-b) extraction with a second extractant comprising the S1 solvent and an S2 solvent;

wherein the S1 solvent is an organic solvent with a water solubility of less than 15% and is characterized by one or more of a polarity related component of Hoy's cohesion parameter (delta-P) between 5 and 10 MPa 1/2 and a hydrogen bonding related component of Hoy's cohesion parameter (delta-H) between 5 and 20 MPa 1/2 ; and

wherein the S2 solvent is an organic solvent with a water solubility of at least 30% and is characterized by one or more of a delta-P greater than 8 MPa 1/2 and a delta-H greater than 12 MPa 1/2 .

8. The method of claim 7 , wherein the S1 solvent is selected from an alcohol, a ketone, and an aldehyde having at least 5 carbon atoms.

9. The method of claim 8 , wherein the S1 solvent is selected from hexanol and 2-ethyl hexanol.

10. The method of claim 7 , wherein the S2 solvent is selected from a C 1 -C 4 mono-alcohol, a C 1 -C 4 poly-alcohol, an aldehyde, and a ketone.

11. The method of claim 7 , comprising removing residual mineral acid in the mineral acid-depleted sugar solution by (ii-a) chromatographic separation.

12. The method of claim 1 , wherein the de-acidifying comprises chromatographic separation.

13. The method of claim 1 , wherein the hydrolyzing of (a) forms the hydrolyzate and residual lignin, wherein the method further comprises:

(a-2) separating the hydrolyzate from the residual lignin before the de-acidifying of (b).

14. The method of claim 1 , further comprising:

(c) converting the saccharides in the de-acidified hydrolyzate to a conversion product.

15. The method of claim 14 , wherein the conversion product is selected from a detergent, polyethylene-based products, polypropylene-based products, polyolefin-based products, polylactic acid-based products, polyhydroxyalkanoate-based products and polyacrylic-based products.

16. The method of claim 14 , wherein the conversion product is selected from carboxylic acids, fatty acids, dicarboxylic acids, hydroxycarboxylic acids, hydroxy di-carboxylic acids, hydroxy-fatty acids, methylglyoxal, mono-, di-, or poly-alcohols, alkanes, alkenes, aromatics, aldehydes, ketones, esters, biopolymers, proteins, peptides, amino acids, vitamins, antibiotics, and pharmaceuticals.

17. The method of claim 14 , wherein the conversion product is selected from ethanol, butanol, isobutanol, a fatty acid, a fatty acid ester, a fatty alcohol and biodiesel.

18. The method of claim 1 , wherein the ratio of total saccharides to total saccharides and water in the hydrolyzate is≥0.20 by weight.

19. The method of claim 1 , wherein the ratio of at least one of the alpha-bonded di-glucose and the beta-bonded di-glucose to total saccharides in the de-acidified hydrolyzate is≥0.01 weight/weight.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 4, 2024
From: VIRDIA LLC
To: INTERNATIONAL N&H DENMARK APS
Reel/Frame 069873/0615 →
CHANGE OF NAME Recorded Mar 18, 2021
From: VIRDIA, INC.
To: VIRDIA, LLC
Reel/Frame 055633/0305 →
RELEASE OF SECURITY INTEREST Recorded Mar 12, 2021
From: TRIPLEPOINT CAPITAL LLC
To: VIRDIA, INC.
Reel/Frame 055599/0793 →
CHANGE OF NAME Recorded May 19, 2020
From: HCL CLEANTECH LTD
To: VIRDIA LTD
Reel/Frame 052704/0254 →
CHANGE OF NAME Recorded Sep 18, 2018
From: HCL TECH LTD
To: HCL CLEANTECH LTD
Reel/Frame 046897/0606 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2018
From: EYAL, AHARON MEIR; MALI, REVITAL; JANSEN, ROBERT P.; VITNER, ASHER
To: HCL CLEANTECH LTD
Reel/Frame 045694/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2018
From: VIRDIA LTD
To: VIRDIA, INC.
Reel/Frame 045694/0783 →