Method of depolymerising phenolic polymers

Patent metadata

Field	Value
Publication number	US-12275697-B2
Application number	US-202017605769-A
Country	US
Kind code	B2
Filing date	Apr 23, 2020
Priority date	Apr 25, 2019
Publication date	Apr 15, 2025
Grant date	Apr 15, 2025

Abstract

The invention provides a method for depolymerising a phenolic polymer, the method comprising reacting the phenolic polymer with dimethylsulphoxide (DMSO) and a hydrogen halide. The phenolic polymer may be selected from the group consisting of lignin and derivatives thereof. The hydrogen halide may be HBr. The quantity of hydrogen halide per gram of phenolic polymer may be from 30 mmoles to 70 mmoles. The quantity of DMSO per gram of phenolic polymer may be from 0.1 mole to 1 mole. The reaction may be performed at a temperature of from 100 to 120° C. The reaction may be carried out for between 10 h and 14 h. The product of the reaction may comprise vanillin.

First claim

The invention claimed is:

1. A method for depolymerising a phenolic polymer, the method comprising reacting the phenolic polymer with dimethylsulphoxide and a hydrogen halide, wherein the product of the reaction comprises at least one compound selected from monomeric and oligomeric forms of vanillin, syringaldehyde, benzaldehyde, p-hydroxybenzaldehyde, eugenol, phenol, phloroglucinol, and 2,4-dihydroxybenzaldehyde.

2. The method as claimed in claim 1 wherein the phenolic polymer is lignin.

3. The method as claimed in claim 2 , wherein the lignin is selected from kraft lignin, softwood kraft lignin, hardwood kraft lignin, Brauns' lignin, cellulolytic enzyme lignin, dioxane acidolysis lignin, Klason lignin, milled wood lignin, periodate lignin, lignosulphates, lignosulphonates, organosolv lignin, steam explosion lignin, lignocellulosic biomass, lignin residue, and any combination thereof.

4. The method as claimed in claim 1 wherein the hydrogen halide is HBr.

5. The method as claimed in claim 1 wherein the quantity of hydrogen halide per gram of phenolic polymer is from 30 mmoles to 70 mmoles.

6. The method as claimed in claim 1 wherein the quantity of dimethylsulphoxide per gram of phenolic polymer is from 0.1 mole to 1 mole.

7. The method as claimed in claim 1 wherein the reaction is performed at a temperature of from 100° C. to 120° C. for between 10 h and 14 h.

8. The method as claimed in claim 1 , which includes isolating a product of the reaction at least in part by vacuum distillation performed at one or more temperatures between 100° C. and 180° C.

9. A method of producing an aromatic compound from a phenolic polymer, the method comprising reacting the phenolic polymer with dimethylsulphoxide and a hydrogen halide to form a reaction mixture, and isolating the aromatic compound from the reaction mixture, wherein the aromatic compound is selected from monomeric and oligomeric forms of vanillin, syringaldehyde, benzaldehyde, p-hydroxybenzaldehyde, eugenol, phenol, phloroglucinol, and 2,4-dihydroxybenzaldehyde.

10. The method as claimed in claim 9 wherein the phenolic polymer is lignin.

11. The method as claimed in claim 10 wherein the lignin is selected from kraft lignin, softwood kraft lignin, hardwood kraft lignin, Brauns' lignin, cellulolytic enzyme lignin, dioxane acidolysis lignin, Klason lignin, milled wood lignin, periodate lignin, lignosulphates, lignosulphonates, organosolv lignin, steam explosion lignin, lignocellulosic biomass, lignin residue, and any combination thereof.

12. The method as claimed in claim 9 wherein the quantity of hydrogen halide per gram of phenolic polymer is from 30 mmoles to 70 mmoles.

13. The method as claimed in claim 9 wherein the hydrogen halide is HBr.

14. The method as claimed in claim 9 wherein the quantity of dimethylsulphoxide per gram of phenolic polymer is from 0.1 mole to 1 mole.

15. The method as claimed in claim 9 wherein the reaction is performed at a temperature of from 100° C. to 120° C. for between 10 h and 14 h.

16. A method of producing vanillin from lignin, the method comprising reacting the lignin with dimethylsulphoxide and a hydrogen halide to form a reaction mixture, and isolating vanillin from the reaction mixture.

17. The method as claimed in claim 16 wherein the quantity of hydrogen halide per gram of lignin is from 30 mmoles to 70 mmoles.

18. The method as claimed in claim 16 wherein the quantity of dimethylsulphoxide per gram of lignin is from 0.1 mole to 1 mole.

19. The method as claimed in claim 16 wherein the hydrogen halide is HBr.

20. The method as claimed in claim 16 wherein the reaction is performed at a temperature of from 100° C. to 120° C. for between 10 h and 14 h.

Assignees

• Univ Stellenbosch

Inventors

• Sibanda Ndumiso
• Pasch Harold
• Pfukwa Helen

Classifications

• C08L97/005

  Lignin · CPC title

• C07C45/59

  in five-membered rings (from ozonides C07C45/40) · CPC title

• C07C27/00 Primary

  Processes involving the simultaneous production of more than one class of oxygen-containing compounds · CPC title

• C08J11/28

  by treatment with organic compounds containing nitrogen, sulfur or phosphorus · CPC title

• C07G1/00

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