Production of monomers from lignin during depolymerization of lignocellulose-containing composition

Patent metadata

Field	Value
Publication number	US-11639324-B2
Application number	US-202017129862-A
Country	US
Kind code	B2
Filing date	Dec 21, 2020
Priority date	Apr 13, 2016
Publication date	May 2, 2023
Grant date	May 2, 2023

Abstract

The present invention relates to a method for preparing monomers via depolymerisation from lignocellulose-containing biomass.

First claim

The invention claimed is:

1. A method for producing fragments of lignin comprising the steps of:
a) providing a lignocellulose-containing composition, suspended in an organic solvent comprising less than 50% v/v of water;
b) heating the composition of step a) under acidic conditions together with an aldehyde, boronic acid or a compound selected from 2-methoxypropene, dimethyl carbonate and 2,2-dimethoxypropane to achieve a mixture; and
c) separating fragments of lignin from the mixture of step b),

wherein the aldehyde, boronic acid or compound selected from 2-methoxypropene, dimethyl carbonate, and 2,2-dimethoxypropane is present in a weight ratio of at least 1:25 relative to the lignocellulose-containing composition, wherein the aldehyde, the boronic acid or the compound selected from 2-methoxypropene, dimethyl carbonate and 2,2-dimethoxypropane weight is based on the weight of formaldehyde.

2. The method according to claim 1 , wherein in a step d) the fragments of lignin of step c) are converted into monomers.

3. The method according to claim 2 , wherein the organic solvent is selected from the group consisting of alcohols with 1 to 6 carbon atoms, cyclic ethers, and lactones.

4. The method according to claim 2 , wherein the lignocellulose-containing composition has a lignin content of 20-40 wt. %.

5. The method according to claim 2 , wherein the monomers are selected from Formulae M1 to M24

6. The method according to claim 1 , wherein the acidic conditions of step b) are achieved by adding one or more acidic components to the composition of step a) and wherein the acidic components are selected from the group consisting of organic carboxylic acids or mineral acids.

7. The method according to claim 6 , wherein the acidic conditions of step b) are achieved by adding 1 to 10 mmol of the acidic components per gram of lignocellulose-containing composition.

8. The method according to claim 1 , wherein in step b) the composition is heated under acidic conditions together with an aldehyde according to formula (I)

wherein R is a hydrogen or an organic residue with 1 to 10 carbon atoms.

9. The method according to claim 8 , wherein R is an aromatic residue being substituted with one or more substituents selected from the group consisting of alkyl groups with 1 to 4 carbon atoms, halogen, nitro, nitrile, carboxylic group, carboxylic esters, carboxylic amide, methoxy and ethoxy.

10. The method according to claim 9 , wherein in step b) the composition is heated under acidic conditions together with an aldehyde according to formula (I)

wherein R is selected from the group consisting of phenyl, o-tolyl and p-tolyl.

11. The method according to claim 8 , wherein R is an aliphatic substituted or unsubstituted residue.

12. The method according to claim 11 , wherein in step b) the composition is heated under acidic conditions together with an aldehyde according to formula (I)

wherein R is selected from the group consisting of methyl, ethyl, propyl and butyl.

13. The method according to claim 11 , wherein in step b) the composition is heated under acidic conditions together with an aldehyde according to formula (I)

wherein R is selected from the group consisting of cyclopropyl, isopropyl and tert-butyl.

14. The method according to claim 1 , wherein in step b) a temperature of 50 to 120° C. is applied for 1 to 8 hours.

15. The method according to claim 1 , wherein the lignocellulose-containing composition and aldehyde, boronic acid or compound selected from 2-methoxypropene, dimethyl carbonate and 2,2-dimethoxypropane are present in a weight ratio of 25:1 to 1:1, wherein the aldehyde, the boronic acid or the compound selected from 2-methoxypropene, dimethyl carbonate and 2,2-dimethoxypropane weight is based on the weight of formaldehyde.

16. The method according to claim 1 , wherein the organic solvent is selected from the group consisting of alcohols with 1 to 6 carbon atoms, cyclic ethers, and lactones.

17. The method according to claim 1 , wherein in step b) the composition is heated under acidic conditions together with an aldehyde according to formula (I)

wherein R is selected from the group consisting of methyl, ethyl, propyl and butyl.

18. The method according to claim 1 , wherein in step b) the composition is heated under acidic conditions together with an aldehyde according to formula (I)

wherein R is selected from the group consisting of cyclopropyl, isopropyl and tert-butyl.

19. The method according to claim 1 , wherein in step b) the composition is heated under acidic conditions together with an aldehyde according to formula (I)

wherein R is selected from the group consisting of phenyl, o-tolyl and p-tolyl.

20. The method according to claim 1 , wherein the lignocellulose-containing composition has a lignin content of 20-40 wt. %.

21. A method for producing fragments of xylan via depolymerization comprising the steps of:
a) providing a lignocellulose-containing composition,
b) heating the composition of step a) under acidic conditions together with an aldehyde, boronic acid or a compound selected from 2-methoxypropene, dimethyl carbonate and 2,2-dimethoxypropane to obtain a mixture,
c′) separating the fragments of xylan from the mixture of step b),

wherein the aldehyde, boronic acid or compound selected from 2-methoxypropene, dimethyl carbonate, and 2,2-dimethoxypropane is present in a weight ratio of at least 1:25 relative to the lignocellulose-containing composition, wherein the aldehyde, the boronic acid or the compound selected from 2-methoxypropene, dimethyl carbonate and 2,2-dimethoxypropane weight is based on the weight of formaldehyde.

22. The method according to claim 21 , wherein step b) involves heating the composition of step a) under acidic conditions together with an aldehyde, according to formula (I)

wherein R is selected from the group consisting of methyl, ethyl, propyl and butyl.

23. The method according to claim 21 , wherein step b) involves heating the composition of step a) under acidic conditions together with an aldehyde, according to formula (I)

wherein R is selected from the gro

Assignees

• Ecole Polytechnique Fed Lausanne Epfl

Inventors

• Luterbacher Jeremy Scott
• Shuai Li

Classifications

• C07H9/04

  Cyclic acetals · CPC title

• C07C41/01 Primary

  Preparation of ethers · CPC title

• C07C43/23

  containing hydroxy or O-metal groups · CPC title

• C08B37/0057

  beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof · CPC title

• C07G1/00

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