High purity lignin, lignin compositions, and higher structured lignin

• US 10,059,730 B2
• Filed: 03/14/2014
• Issued: 08/28/2018
• Est. Priority Date: 03/15/2013
• Status: Active Grant

• Current Assignee: Renmatix, Inc.
• Original Assignee: Renmatix, Inc.
• Inventors: Capanema, Ewellyn A., Balakshin, Mikhail Y.
• Primary Examiner(s): Heincer, Liam J
• Application Number:
  US14/213,680
• Publication Number:
  US 20140275501A1
• Time in Patent Office: 1,628 Days
• CPC Class Codes: C07G 1/00 Lignin; Lignin derivatives

Abstract

Disclosed are lignins and lignin compositions having high purity. Also disclosed are lignins having unique structural characteristics, including less structural degradation than conventional lignins.

Claims

1. A technical lignin comprising:

a methoxyl content of 102 units to 120 units, per 100 aromatic units; and

an oxygenated aliphatic content of 100 units to about 150 units, per 100 aromatic units.

2. The technical lignin of claim 1, wherein:

the methoxyl content is 104 units to 120 units, per 100 aromatic units;

or

the oxygenated aliphatic content is 100 units to 148 units, per 100 aromatic units.

3. The technical lignin of claim 1, further comprising:

a degree of condensation of about 30 to about 50.

4. The technical lignin of claim 1, further comprising:

a ratio of syringyl to guaiacyl of about 1 to about 1.5.

5. The technical lignin of claim 1, further comprising:

a phenolic hydroxyl content of about 30 units to about 100 units, per 100 aromatic units.

6. The technical lignin of claim 1, further comprising:

an aliphatic hydroxyl content of about 35 units to about 70 units, per 100 aromatic units.

7. The technical lignin of claim 1, further comprising:

a total COOR content of about 5 units to about 25 units, per 100 aromatic units.

8. The technical lignin of claim 1, further comprising:

a total carbonyl content of about 10 units to about 25 units, per 100 aromatic units.

9. The technical lignin of claim 1,

wherein the technical lignin is derived from hardwood biomass.

10. The technical lignin of claim 1,

wherein the technical lignin is derived from biomass selected from the group consisting of softwood, annual fiber, municipal solid waste, agricultural residue, manufacturing waste, and any combination thereof.

11. A technical lignin comprising:

a methoxyl content of 102 units to 138 units, per 100 aromatic units; and

an oxygenated aliphatic content of 100 units to 120 units, per 100 aromatic units.

12. The technical lignin of claim 11, wherein:

the methoxyl content is 104 units to 138 units, per 100 aromatic units;

or

the oxygenated aliphatic content is 100 units to 118 units, per 100 aromatic units.

13. The technical lignin of claim 11, further comprising:

a degree of condensation of about 30 to about 50.

14. The technical lignin of claim 11, further comprising:

a ratio of syringyl to guaiacyl of about 1 to about 1.5.

15. The technical lignin of claim 11, further comprising:

a phenolic hydroxyl content of about 30 units to about 100 units, per 100 aromatic units.

16. The technical lignin of claim 11, further comprising:

aliphatic hydroxyl content of about 35 units to about 70 units, per 100 aromatic units.

17. The technical lignin of claim 11, further comprising:

a total COOR content of about 5 units to about 25 units, per 100 aromatic units.

18. The technical lignin of claim 11, further comprising:

a total carbonyl content of about 10 units to about 25 units, per 100 aromatic units.

19. The technical lignin of claim 11,

wherein the technical lignin is derived from hardwood biomass.

20. The technical lignin of claim 11,

wherein the technical lignin is derived from biomass selected from the group consisting of softwood, annual fiber, municipal solid waste, agricultural residue, manufacturing waste, and any combination thereof.

21. A technical lignin comprising:

a methoxyl content of 102 units to 114 units, per 100 aromatic units; and

an oxygenated aliphatic content of about 80 units to about 150 units, per 100 aromatic units.

22. The technical lignin of claim 21, wherein:

the methoxyl content is 104 units to 114 units, per 100 aromatic units;

or

the oxygenated aliphatic content is 85 units to 145 units, per 100 aromatic units.

23. The technical lignin of claim 21, further comprising:

a degree of condensation of about 30 to about 50.

24. The technical lignin of claim 21, further comprising:

a ratio of syringyl to guaiacyl of about 1 to about 1.5.

25. The technical lignin of claim 21, further comprising:

a phenolic hydroxyl content of about 30 units to about 100 units, per 100 aromatic units.

26. The technical lignin of claim 21, further comprising:

an aliphatic hydroxyl content of about 35 units to about 70 units, per 100 aromatic units.

27. The technical lignin of claim 21, further comprising:

a total COOR content of about 5 units to about 25 units, per 100 aromatic units.

28. The technical lignin of claim 21, further comprising:

a total carbonyl content of about 10 units to about 25 units, per 100 aromatic units.

29. The technical lignin of claim 21,

wherein the technical lignin is derived from hardwood biomass.

30. The technical lignin of claim 21,

wherein the technical lignin is derived from biomass selected from the group consisting of softwood, annual fiber, municipal solid waste, agricultural residue, manufacturing waste, and any combination thereof.

31. A technical lignin having a ¹H—

¹³C HSQC NMR spectrum comprising the cross peaks shown in FIG. 4.

32. A technical lignin having a ¹³C NMR spectrum comprising the spectrum shown in FIG. 5.