Renewable aromatics from lignocellulosic lignin

Patent metadata

Field	Value
Publication number	US-12012429-B2
Application number	US-202117189998-A
Country	US
Kind code	B2
Filing date	Mar 2, 2021
Priority date	Dec 7, 2012
Publication date	Jun 18, 2024
Grant date	Jun 18, 2024

Abstract

The present invention provides novel and improved processes for treating a lignocellulosic biomass or technical lignin using ionic liquids to obtain lignin breakdown products and polysaccharide biomass components. Recycling of ionic liquids can be included in the methods of the invention.

First claim

What is claimed is:

1. A method comprising:
(i) contacting a starting material comprising a technical lignin with an ionic liquid to generate a solubilized material;
(ii) precipitating at least a fraction of the solubilized material with a precipitant to generate a precipitated fraction and a supernatant, wherein the precipitant is selected from the group consisting of octanol, hexanol, and mixtures thereof,
(iii) separating the precipitated fraction from the supernatant;
(iv) adding a solvent to the separated supernatant comprising the ionic liquid and the precipitant, wherein the solvent promotes phase separation of the ionic liquid and the precipitant, thereby separating the supernatant into an ionic liquid phase and a precipitant phase; and
(v) isolating the ionic liquid from the ionic liquid phase of step (iv).

2. The method of claim 1 , further comprising isolating the precipitant phase of step (iv).

3. The method of claim 1 , further comprising reusing the ionic liquid, the precipitant, or the ionic liquid and the precipitant.

4. The method of claim 1 , wherein the ionic liquid, wherein the ionic liquid is selected from the group consisting of [C 2 mim][OAc], EMIM Cl, EMIM HOSO 3 , EMIM MeOSO 3 , EMIM EtOSO 3 , EMIM MeSO 3 , EMIM AlCl 4 , EMIM SCN, BMIM Acetate, BMIM Cl, BMIM HOSO 3 , BMIM MeSO 3 , BMIM MeOSO 3 , BMIM AlCl 4 , BMIM SCN, EDIM EtOSO 3 , MTEOA MeOSO 3 , MIM Cl, MIM HOSO 3 , 1,2,4-trimethylpyrazolium methylsulfate, tributylmethylammonium methylsulfate, choline acetate, and choline salicylate.

5. The method of claim 1 , wherein the ionic liquid is [C 2 mim][OAc].

6. The method of claim 1 , wherein the solvent that promotes phase separation of the ionic liquid and the precipitant is selected from the group consisting of water, ethanol, acetone, and combinations thereof.

7. The method of claim 1 , further comprising extracting low molecular weight or monomeric non-polar aromatic lignin compounds from the supernatant with an extractant.

8. The method of claim 7 , wherein the aromatic lignin compounds are phenols, guaicols, syringols, eugenol, conyferols, catechols, or combinations thereof.

9. The method of claim 7 , wherein the extractant is a non-polar solvent.

10. The method of claim 9 , wherein the non-polar solvent is selected from the group consisting of benzene, hexane, and pentane.

11. The method of claim 1 , wherein from about 0.1 volumes to about 10 volumes of precipitant, with respect to the ionic liquid, are added to the mixture containing the solubilized material in step (ii).

12. The method of claim 1 , wherein the solvent that promotes phase separation of the ionic liquid and the precipitant in step (iv) is added to the supernatant in an amount of from about 1% (v/v) to about 50% (v/v).

13. The method of claim 1 , wherein the technical lignin comprises kraft lignin, a lignosulfate, alkali lignin, low sulfonate alkali lignin, or a combination thereof.

Assignees

• Nat Tech & Eng Solutions Sandia Llc

Inventors

• Sathitsuksanoh Noppadon
• Sun Ning
• Shi Jian
• George Anthe
• Sawant Manali
• Singh Seema
• Simmons Blake

Classifications

• D21C11/0007

  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 title

• D21C3/20

  with organic solvents {or in solvent environment} · CPC title

• C07G1/00 Primary

  Low-molecular-weight derivatives of lignin (high-molecular-weight derivatives of lignin {C08H6/00}) · CPC title