Compositions containing recyclable ionic liquids for use in biomass processing

• US 9,394,375 B2
• Filed: 03/23/2012
• Issued: 07/19/2016
• Est. Priority Date: 03/25/2011
• Status: Active Grant

• Current Assignee: Board of Trustees of The University of Alabama (University of Alabama System)
• Original Assignee: Board of Trustees of The University of Alabama (University of Alabama System)
• Inventors: Daly, Daniel T., Rogers, Robin D., Qin, Ying
• Primary Examiner(s): Nguyen, Nam
• Assistant Examiner(s): PERRIN, CLARE M
• Application Number:
  US13/428,786
• Publication Number:
  US 20120245336A1
• Time in Patent Office: 1,579 Days
• US Class Current: 1/1
• CPC Class Codes: C08B 1/00 Preparatory treatment of cellulose for making derivatives thereof , e.g. pre-treatment, pre-soaking, activation
• CPC Class Codes: C08B 37/0003 General processes for their isolation or fractionation, e.g. purification or extraction from biomass
• CPC Class Codes: C08B 37/003 Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
• CPC Class Codes: C08H 8/00 Macromolecular compounds derived from lignocellulosic materials pretreatment thereof B27N

Abstract

Compositions containing biomass, an ionic liquid, and an amide are described herein. Methods of their preparation and use in extracting and processing biomass are also described herein. Further described herein are films and fibers prepared from the compositions. Methods of recovering the ionic liquids used to process the biomass are also provided.

Claims

1. A method of precipitating a biomass, comprising:

a. providing a composition comprising a biomass, an ionic liquid, and an amine, wherein the composition is substantially free from water; and

b. contacting the composition with carbon dioxide in an amount effective to react with the amine to form an amine carbamate effective to substantially precipitate the biomass from the composition, thereby forming a precipitated biomass.

2. The method of claim 1, wherein the biomass is a lignocellulosic biomass.

3. The method of claim 1, wherein the biomass is derived from softwood, hardwood, or a combination thereof.

4. The method of claim 1, wherein the biomass is a crustacean biomass.

5. The method of claim 1, wherein providing the composition comprises dissolving the biomass in the ionic liquid at a temperature of from about 0°

C. to about 250°

C.

6. The method of claim 1, wherein providing the composition comprises dissolving the biomass in the ionic liquid and the amine at a temperature of from about 0°

C. to about 250°

C.

7. The method of claim 1, wherein contacting the composition comprises bubbling the carbon dioxide into the composition at a temperature of from about 20°

C. to about 50°

C.

8. The method of claim 1, further comprising separating at least a portion of cellulose or chitin from the composition.

9. The method of claim 1, further comprising recovering at least a portion of the ionic liquid from the composition.

10. The method of claim 9, wherein the recovering comprises separating the precipitated biomass from the composition and heating the composition at a temperature of from about 30°

C. to about 150°

C.

11. The method of claim 1, wherein the ionic liquid comprises one or more cations and one or more anions and wherein the cations comprise one or more compounds having the formula:

12. The method of claim 1, wherein the ionic liquid comprises one or more cations and one or more anions and wherein the one or more cations comprise one or more compounds having the formula:

13. The method of claim 12, wherein the one or more cations comprise an imidazolium ion having the formula:

14. The method of claim 1, wherein the ionic liquid comprises 1-(C₁-C₆ alkyl)-3-methyl-imidazolium halide or 1-(C₁-C₆ alkyl)-3-methyl-imidazolium acetate.

15. The method of claim 1, wherein the amine is selected from the group consisting of primary amines, secondary amines, tertiary amines, cyclic amines, or mixtures thereof.

16. The method of claim 1, wherein the amine is an alkanolamine.

17. The method of claim 1, wherein the amine is selected from the group consisting of ethylenediamine, butylamine, pentylamine, or mixtures thereof.

18. The method of claim 1, wherein the amine is a monoamine, a diamine, or a polyamine.

19. The method of claim 1, wherein the ionic liquid and the amine are present in a ratio from 9:

1 to 1;

9.

20. A composition, comprising:

biomass;

an ionic liquid;

an amine;

CO₂; and

an amine carbamate;

wherein the composition is substantially free from water.

21. The composition of claim 20, wherein the biomass is a lignocellulosic biomass.

22. The composition of claim 20, wherein the biomass is derived from softwood, hardwood, or a combination thereof.

23. The composition of claim 20, wherein the biomass is a crustacean biomass.

24. The composition of claim 20, wherein the ionic liquid comprises one or more cations and one or more anions and wherein the cations comprise one or more compounds having the formula:

25. The composition of claim 20, wherein the ionic liquid comprises one or more cations and one or more anions and wherein the one or more cations comprise one or more compounds having the formula:

26. The composition of claim 25, wherein the one or more cations comprise an imidazolium ion having the formula:

27. The composition of claim 20, wherein the ionic liquid comprises 1-(C₁-C₆ alkyl)-3-methyl-imidazolium halide or 1-(C₁-C₆ alkyl)-3-methyl-imidazolium acetate.

28. The composition of claim 20, wherein the amine is selected from the group consisting of primary amines, secondary amines, tertiary amines, cyclic amines, or mixtures thereof.

29. The composition of claim 20, wherein the amine is an alkanolamine.

30. The composition of claim 20, wherein the amine is selected from the group consisting of ethylenediamine, butylamine, pentylamine, or mixtures thereof.

31. The composition of claim 20, wherein the amine is a monoamine, a diamine, or a polyamine.