Continuous process for the ozonolysis of lignin to yield aromatic monomers

Patent metadata

Field	Value
Publication number	US-10745335-B2
Application number	US-201716317173-A
Country	US
Kind code	B2
Filing date	Jul 13, 2017
Priority date	Jul 14, 2016
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

A method for processing lignin may comprise flowing a lignin composition comprising a lignin polymer and a solvent through a reaction chamber of a continuous flow reactor, the lignin polymer comprising hydroxycinnamic groups bound to a polymeric backbone; flowing ozone through the reaction chamber containing the lignin composition under conditions to maximize oxidative cleavage of the hydroxycinnamic groups to produce one or more types of aromatic monomers while minimizing oxidative cleavage of the polymeric backbone; and collecting the one or more types of aromatic monomers, e.g., by a size-selective membrane separation device.

First claim

What is claimed is:

1. A method for processing lignin, the method comprising:
flowing a lignin composition comprising a lignin polymer and a solvent through a reaction chamber of a continuous flow reactor, the lignin polymer comprising hydroxycinnamic groups bound to a polymeric backbone;
flowing ozone through the reaction chamber containing the lignin composition under conditions to maximize oxidative cleavage of the hydroxycinnamic groups to produce one or more types of aromatic monomers while minimizing oxidative cleavage of the polymeric backbone; and
collecting the one or more types of aromatic monomers.

2. The method of claim 1 , wherein the lignin is extracted from herbaceous biomass.

3. The method of claim 2 , wherein the herbaceous biomass is corn stover.

4. The method of claim 1 , wherein the method is carried out at a flow rate of the lignin composition and a holdup volume selected to provide a reaction time of less than 10 minutes.

5. The method of claim 1 , wherein the solvent comprises a short chain carboxylic acid.

6. The method of claim 5 , wherein the short chain carboxylic acid is selected from acetic acid, formic acid, propionic acid, and combinations thereof.

7. The method of claim 5 , wherein the solvent further comprises water.

8. The method of claim 7 , wherein the amount of water is less than 20% by volume.

9. The method of claim 1 , wherein the method is carried out at a reaction temperature in the range of from 20° C. to 80° C.

10. The method of claim 1 , wherein the method is carried out at a flow rate of the lignin composition and a holdup volume selected to provide a reaction time of less than 5 minutes; the solvent is a short chain carboxylic acid or the short chain carboxylic acid combined with water; the method is carried out at a reaction temperature in the range of from 20° C. to 80° C.; and the lignin is extracted from herbaceous biomass.

11. The method of claim 10 , wherein the solvent is acetic acid or acetic acid combined with water.

12. The method of claim 1 , wherein the total yield of the one or more types of aromatic monomers, as measured by weight percent of the weight of the lignin in the lignin composition, is substantially the same as the amount of hydroxycinnamic groups on the lignin polymer, as measured by weight percent of the weight of the lignin in the lignin composition.

13. The method of claim 1 , wherein the conditions result in substantially no oxidative cleavage of the polymeric backbone.

14. The method of claim 1 , wherein the total yield of the one or more types of aromatic monomers is at least 7% by weight as compared to the weight of the lignin in the lignin composition.

15. The method of claim 14 , wherein the one or more types of aromatic monomers are selected from vanillin, 4-hydroxybenzaldehyde, vanillic acid, 4-hydroxybenzoic acid, and combinations thereof.

16. The method of claim 14 , wherein the conditions result in substantially no oxidative cleavage of the polymeric backbone.

17. The method of claim 16 , wherein the one or more types of aromatic monomers are selected from vanillin, 4-hydroxybenzaldehyde, vanillic acid, 4-hydroxybenzoic acid, and combinations thereof.

18. The method of claim 1 , further comprising separating the one or more types of aromatic monomers from the polymeric backbone by size-selective membrane filtration.

19. The method of claim 18 , wherein more than 95% of the polymeric backbone is retained by a membrane of the size-selective membrane filtration while selectively rejecting the one or more types of aromatic monomers.

20. The method of claim 18 , further comprising subjecting the separated polymeric backbone to an additional depolymerization process to depolymerize the polymeric backbone.

Assignees

• Univ Kansas

Inventors

• Subramaniam Bala
• Danby Andrew M
• Lundin Michael D

Classifications

• C07G1/00 Primary

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

• C07C37/70

  by physical treatment · CPC title

• C07C45/786

  by membrane separation process, e.g. pervaporation, perstraction, reverse osmosis · CPC title

• C07C37/60

  by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen · CPC title

• C08H6/00

  Macromolecular compounds derived from lignin, e.g. tannins, humic acids · CPC title