Methods for treating lignocellulosic materials

• US 9,657,146 B2
• Filed: 11/06/2013
• Issued: 05/23/2017
• Est. Priority Date: 03/14/2013
• Status: Active Grant

• Current Assignee: Virdia Ltd
• Original Assignee: Virdia, Inc. (Stora Enso Oyj)
• Inventors: Jansen, Robert, Travisano, Philip, Matis, Neta, Perry, Rotem, Madsen, Lee, Lapidot, Noa, Lawson, James Allen, Bauer, Timothy Allen, Hallac, Bassem, Zviely, Michael
• Primary Examiner(s): SHIAO, REI TSANG
• Application Number:
  US14/787,755
• Publication Number:
  US 20160130408A1
• Time in Patent Office: 1,294 Days
• Field of Search: 4234472
• CPC Class Codes: C08H 6/00 Macromolecular compounds derived from lignin, e.g. tannins, humic acids
• CPC Class Codes: C08H 8/00 Macromolecular compounds derived from lignocellulosic materials pretreatment thereof B27N
• CPC Class Codes: C08L 97/005 Lignin

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

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_aH_bO_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_aH_bO_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_aH_bO_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.