IP Library Granted Patent US 9,657,146
Granted Patent B2
US 9,657,146 · App. 14/787,755 · Granted May 23, 2017

Methods for treating lignocellulosic materials

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Quick Facts
Patent No.
US 9,657,146
App. No.
14/787,755
Granted
May 23, 2017
Kind
B2
Abstract

The present invention relates to methods of processing lignocellulosic material to obtain hemicellulose sugars, cellulose sugars, lignin, cellulose and other high-value products such as asphalt and bio oils. Also provided are hemicellulose sugars, cellulose sugars, lignin, cellulose, and other high-value products such as asphalt and bio oils.

Claims (48)

1. A lignin composition having a degree of condensation of less than 0.9 and nitrogen in an amount up to 0.5% weight/weight and further characterized by at least four characteristics selected from the group consisting of:

(i) lignin aliphatic hydroxyl groups in an amount up to 2 mmole/g;

(ii) at least 2.5 mmole/g lignin phenolic hydroxyl groups;

(iii) less than 0.40 mmole/g lignin carboxylic hydroxyl groups;

(iv) sulfur in an amount up to 1% weight/weight;

(v) 5% degradation temperature higher than 220° C.;

(vi) 10% degradation temperature higher than 260° C.;

(vii) less than 1% ash weight/weight;

(viii) a formula of C a H b O c ; wherein a is 9, b is less than 12 and c is less than 3.5;

(ix) a methoxyl content of at least 0.8;

(x) an O/C weight ratio of less than 0.4; and

(xi) a glass transition elevation between a first and a second heat cycle as measured by differential scanning calorimetry according to DIN 53765 in the range of 10 to 30° C.

2. The composition of claim 1 , further characterized by at least one additional characteristic selected from the group consisting of:

(i) less than 1% carbohydrates weight/weight;

(ii) solubility in DMSO is >100 g/L;

(iii) solubility in THF is >35 g/L;

(iv) solubility in 0.1 N NaOH aqueous solution is >8 g/L;

(v) less than 1% water by weight;

(vi) less than 1% volatile components at 200° C. by weight;

(vii) a sulfur concentration of less than 0.1% weight/weight;

(viii) soluble sugar content of less than 1% weight/weight;

(ix) a phosphorus concentration of less than 100 PPM; and

(x) less than 0.1 times the amount of volatile sulfur compounds found in Kraft lignin.

3. The composition of claim 1 , prepared from a substrate comprising hardwood, softwood, or bagasse.

4. The composition of claim 1 , further comprising an organic solvent.

5. The composition of claim 4 , wherein the organic solvent is selected from the group consisting of an alcohol, a ketone, an aldehyde, an alkane, an organic acid and a furan of 6 carbons or less.

6. The composition of claim 5 , wherein the organic solvent is methylethyl ketone.

7. The composition of claim 1 , further comprising less than 20% cellulose weight/weight.

8. The composition of claim 1 , comprising ash in an amount less than 0.5% weight/weight.

9. The composition of claim 1 , further comprising a marker molecule.

10. The composition of claim 9 , wherein the marker molecule is selected from the group consisting of furfural, hydroxy-methyl furfural, 2,3,5 trimethyl furan, products of their condensation, color compounds, acetic acid, p-hydroxyphenoxyacetic acid, 4-hydroxy-3,5-dimethoxyphenyl acetic acid, methylethyl ketone, methylpropenyl ketone, 3-(2-furyl)-3-penten-2-one, 3-methyl-2-penten-4-one, 3,4-dimethyl-4-hexene-one, 5-ethyl-5-hexene-3-one, 5-methyl-4-heptene-3-one, o-hydroxyanisole, 3-ethyl-4-methyl-3-penten-2-one, 3,4,4-trimethyl-2-cyclohexene-1-one, 2′-hydroxy-4′,5′-dimethylacetophenone, 1-(4-hydroxy-3-methoxyphenyl)propane methanol, galacturonic acid, dehydroabietic acid, glycerol, fatty acids and resin acids.

11. The composition of claim 1 , comprising the formula of C a H b O c , wherein a is 9, b is between 8.0 and 11.0, and c is less than 3.5.

12. The composition of claim 1 , comprising:

(i) lignin aliphatic hydroxyl groups in an amount up to 2 mmole/g;

(ii) at least 2.5 mmole/g lignin phenolic hydroxyl groups; and

(iii) less than 0.40 mmole/g lignin carboxylic hydroxyl groups.

13. The composition of claim 1 , comprising:

(i) less than 0.40 mmole/g lignin carboxylic hydroxyl groups;

(ii) sulfur in an amount up to 1% weight/weight;

(iii) less than 1% ash weight/weight;

(iv) the formula of C a H b O c ; wherein a is 9, b is between 8.0 and 11.0, and c is less than 3.5; and

(v) a degree of condensation of less than 0.9.

14. The composition of claim 13 , further comprising less than 1% carbohydrates weight/weight.

15. The composition of claim 1 , further comprising less than 1000 ppm each of sulfur, calcium, iron, potassium, magnesium, and sodium.

16. The composition of claim 15 , comprising less than 1% ash and less than 1% carbohydrates weight/weight.

17. The composition of claim 1 , wherein the composition is provided as fibers.

18. The composition of claim 1 , comprising lignin aliphatic hydroxyl groups in an amount in the range of 0.5 mmole/g to 2 mmole/g.

19. The composition of claim 1 , comprising a methoxyl content of at least 0.9.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 20, 2024
From: VIRDIA, LLC
To: STORA ENSO OYJ
Reel/Frame 069652/0111 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2016
From: BAUER, TIMOTHY ALLEN
To: VIRDIA, INC.
Reel/Frame 037804/0411 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2016
From: JANSEN, ROBERT; TRAVISANO, PHILIP; MADSEN, LEE R., II; MATIS, NETA; PERRY, ROTEM; LAWSON, JAMES ALAN; LAPIDOT, NOA; BAUER, TIMOTHY ALLEN; HALLAC, BASSEM; ZVIELY, MICHAEL
To: VIRDIA, INC.
Reel/Frame 037596/0214 →