Methods for treating lignocellulosic materials

• US 9,493,851 B2
• Filed: 05/03/2013
• Issued: 11/15/2016
• Est. Priority Date: 05/03/2012
• Status: Active Grant

• Current Assignee: Virdia Ltd
• Original Assignee: Virdia, Inc. (Stora Enso Oyj)
• Inventors: Jansen, Robert, Gregoire, Claire, Travisano, Philip, Madsen, Lee, Matis, Neta, Har-Tal, Yael, Eliahu, Shay, Lawson, James Alan, Lapidot, Noa, Eyal, Aharon M., Bauer, Timothy Allen, Sade, Hagit, McWilliams, Paul, Zviely, Michael, Carden, Adam
• Primary Examiner(s): Mayes, Melvin C
• Assistant Examiner(s): COHEN, STEFANIE J
• Application Number:
  US14/398,444
• Publication Number:
  US 20150087031A1
• Time in Patent Office: 1,292 Days
• US Class Current: 1/1
• CPC Class Codes: C07G 1/00 Lignin; Lignin derivatives
• CPC Class Codes: C10L 1/02 essentially based on components consisting of carbon, hydrogen, and oxygen only
• CPC Class Codes: C10L 1/023 for spark ignition
• CPC Class Codes: C10L 1/026 for compression ignition
• CPC Class Codes: C12P 19/02 Monosaccharides 2-ketogulonic acid C12P7/60
• CPC Class Codes: C12P 19/14 produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase , e.g. by cellulase, hemicellulase
• CPC Class Codes: C12P 2201/00 Pretreatment of cellulosic or lignocellulosic material for subsequent enzymatic treatment or hydrolysis
• CPC Class Codes: C12P 2203/00 Fermentation products obtained from optionally pretreated or hydrolyzed cellulosic or lignocellulosic material as the carbon source ethanol C12P7/10
• CPC Class Codes: C13K 1/02 obtained by saccharification of cellulosic materials manufacture of fodder A23K10/32
• CPC Class Codes: C13K 1/04 Purifying
• CPC Class Codes: C13K 13/002 Xylose
• CPC Class Codes: C13K 13/007 Separation of sugars provided for in subclass C13K C13K3/00 takes precedence
• CPC Class Codes: D21C 11/0007 Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for volatile compounds obtained by decomposition of spent liquors in order to regenerate them D21C11/125; compounds obtained by fractionating the liquors in order to regenerate them D21C11/0042
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel

Abstract

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

Claims

1. A method of refining a sugar stream, comprising:

(i) contacting the sugar stream with an amine extractant to form a mixture;

(ii) separating from the mixture a first stream comprising the amine extractant and an acid or an impurity; and

a second stream comprising one or more sugars; and

(iii) contacting the first stream with a base to form a neutralized amine extractant.

2. The method of claim 1, wherein the first stream is an organic stream and the second stream is an aqueous stream.

3. The method of claim 1, wherein the first stream comprises less than 0.5% w/w sugars.

4. The method of claim 1, wherein the second stream comprises less than 0.5% w/w acid.

5. The method of claim 1, wherein the second stream comprises less than 0.5% w/w amine.

6. The method of claim 1, wherein the second stream comprises less than 0.5% w/w impurities.

7. The method of claim 1, wherein impurities are extracted from the sugar stream into the amine extractant.

8. The method of claim 1, further comprising, prior to step (i), contacting the sugar stream with a strong acid cation exchanger to remove residual cations.

9. The method of claim 1, wherein the amine extractant comprises an amine and a diluent.

10. The method of claim 9, wherein the ratio of the amine and the diluent is between 3:

7 and 6;

4.

11. The method of claim 9, wherein the diluent comprises a C6, C8, C10, C12, C14, or C16 alcohol or kerosene.

12. The method of claim 9, wherein the diluent comprises n-hexanol or 2-ethyl-hexanol.

13. The method of claim 9, wherein the amine is an amine comprising at least 20 carbon atoms.

14. The method of claim 1, further comprising:

contacting the second stream with a strong acid cation exchanger to remove residual amines, thereby forming an amine-removed hydrolysate; and

contacting the amine-removed hydrolysate with a weak base anion exchanger to form a neutralized hydrolysate.

15. The method of claim 1, further comprising:

contacting the second stream with a strong acid cation exchanger to remove residual amines, thereby forming an amine-removed hydrolysate; and

fractionating the amine-removed hydrolysate into a monomeric sugar stream and an oligomeric sugar stream.

16. The method of claim 1, prior to contacting the first stream with the base, further comprising washing the first stream with an aqueous stream to remove sugar from the first stream.

17. The method of claim 16, wherein the washed first stream comprises less than 0.1% weight/weight sugar.

18. The method of claim 1, further comprising washing at least a portion of the neutralized amine extractant with water and recycling the washed amine extractant.

19. The method of claim 1, wherein the first stream comprises the amine extractant, a mineral acid, an organic acid and furfural.

20. The method of claim 1, wherein the sugar stream is a lignocellulosic hydrolysate.

21. A method of refining a sugar stream, comprising:

(i) contacting the sugar stream with an amine extractant to form a mixture; and

(ii) separating from the mixture a first stream comprising the amine extractant and an acid or an impurity; and

a second stream comprising one or more sugars, wherein the amine extractant comprises tri-laurylamine and a diluent.

22. The method of claim 21, wherein the first stream comprises less than 0.5% w/w sugars.

23. The method of claim 21, wherein the second stream comprises less than 0.5% w/w acid, less than 0.5% w/w amine, or less than 0.5 w/w impurities.

24. The method of claim 21, wherein the diluent comprises a C6, C8, C10, C12, C14, or C16 alcohol or kerosene.

25. The method of claim 21, wherein the diluent comprises n-hexanol or 2-ethyl-hexanol.

26. The method of claim 21, wherein the first stream comprises the amine extractant, a mineral acid, an organic acid and furfural.

35. The method of claim 21, further comprising contacting the first stream with a base to form a neutralized amine extractant.

36. The method of claim 35, prior to contacting the first stream with the base, further comprising washing the first stream with an aqueous stream to remove sugar from the first stream.

37. The method of claim 36, wherein the washed first stream comprises less than 0.1% weight/weight sugar.

38. The method of claim 35, further comprising washing at least a portion of the neutralized amine extractant with water and recycling the washed amine extractant.

27. A method of refining a sugar stream, comprising:

(i) contacting the sugar stream with an amine extractant to form a mixture;

(ii) separating from the mixture a first stream comprising the amine extractant and an acid or an impurity; and

a second stream comprising one or more sugars; and

(iii) contacting the second stream with a strong acid cation exchanger to remove residual amines, thereby forming an amine-removed hydrolysate.

28. The method of claim 27, wherein the first stream comprises less than 0.5% w/w sugars.

29. The method of claim 27, wherein the second stream comprises less than 0.5% w/w acid, less than 0.5% w/w amine, or less than 0.5% w/w impurities.

30. The method of claim 27, wherein the amine extractant comprises an amine and a diluent.

31. The method of claim 30, wherein the diluent comprises n-hexanol or 2-ethyl-hexanol.

32. The method of claim 30, wherein the amine is tri-laurylamine.

33. The method of claim 27, wherein the first stream comprises the amine extractant, a mineral acid, an organic acid and furfural.

39. The method of claim 27, further comprising contacting the first stream with a base to form a neutralized amine extractant.

40. The method of claim 39, prior to contacting the first stream with the base, further comprising washing the first stream with an aqueous stream to remove sugar from the first stream.

41. The method of claim 40, wherein the washed first stream comprises less than 0.1% weight/weight sugar.

42. The method of claim 39, further comprising washing at least a portion of the neutralized amine extractant with water and recycling the washed amine extractant.

34. A method of refining a sugar stream, comprising:

(i) contacting the sugar stream with an amine extractant to form a mixture;

(ii) separating from the mixture a first stream comprising the amine extractant and an acid or an impurity; and

a second stream comprising one or more sugars;

(iii) contacting the first stream with a base to form a neutralized amine extractant; and

(iv) contacting the second stream with a strong acid cation exchanger to remove residual amines, thereby forming an amine-removed hydrolysate,

wherein the amine extractant comprises tri-laurylamine and a diluent.