Method for preparing low-molecular lignin derivative

Patent metadata

Field	Value
Publication number	US-10100073-B2
Application number	US-201414892947-A
Country	US
Kind code	B2
Filing date	May 22, 2014
Priority date	May 23, 2013
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

A method of preparing a low-molecular lignin derivative comprises the step of: preparing lignin by hydrolyzing lignocellulosic biomass with an acid; preparing a first mixture by mixing 100 parts by weight of the lignin and 500 parts or more by weight of a phenolic compound; preparing a second mixture by mixing the first mixture with a solvent including the hydrophobic polar solvent; and recovering a low-molecular lignin derivative from the second mixture.

First claim

The invention claimed is:

1. A preparation method of a low-molecular lignin derivative, the method comprising:
preparing lignin by hydrolyzing a hydrophilic carbohydrate of lignocellulosic biomass with an acid;
preparing a first mixture by mixing 100 parts by weight of the lignin and 500 parts by weight or more of a phenolic compound, and a second acid;
preparing a second mixture by mixing the first mixture with a solvent including a hydrophobic polar solvent; and
recovering a low-molecular lignin derivative from the second mixture,

wherein the mixing of the lignin with the phenolic compound is performed at 25° C. to 160° C. for 1 hour or longer to react the lignin and the phenolic compound.

2. The preparation method according to claim 1 , wherein the acid hydrolyzing lignocellulosic biomass comprises hydrochloric acid.

3. The preparation method according to claim 1 , wherein the lignin comprises a dry lignin powder obtained by neutralizing, drying, and pulverizing a lignin separated from a hydrolysate of lignocellulosic biomass.

4. The preparation method according to claim 1 , wherein the phenolic compound is one or more selected from the group consisting of phenol, o-cresol, m-cresol, p-cresol, catechol, resorcinol, hydroquinone, and pyrogallol.

5. The preparation method according to claim 1 , wherein 550 to 2000 parts by weight of the phenolic compound is mixed, based on 100 parts by weight of lignin.

6. The preparation method according to claim 1 , wherein the mixing of the lignin with the phenolic compound is performed at 70° C. to 160° C.

7. The preparation method according to claim 1 , wherein the second acid is one or more selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, and Lewis acid.

8. The preparation method according to claim 1 , wherein the hydrophobic polar solvent is one or more selected from the group consisting of alkyl ketone, alkyl amide, ether, aromatic hetero rings, and aliphatic alcohols.

9. The preparation method according to claim 8 , wherein the hydrophobic polar solvent comprises diethyl ether.

10. The preparation method according to claim 1 , wherein the hydrophobic polar solvent has a dipole moment of 1 debye or higher.

11. The preparation method according to claim 1 , wherein the solvent including the hydrophobic polar solvent further includes a poor solvent.

12. The preparation method according to claim 1 , wherein a precipitate in the second mixture is recycled and added to the first mixture.

13. The preparation method according to claim 1 , wherein a content of the precipitate in the second mixture is 30% or less of the total weight of lignin.

14. A preparation method of a low-molecular lignin derivative, the method comprising:
preparing lignin by hydrolyzing lignocellulosic biomass with an acid;
preparing a first mixture by mixing 100 parts by weight of the lignin and 500 parts by weight or more of a phenolic compound;
preparing a second mixture by mixing the first mixture with a solvent including a hydrophobic polar solvent; and
recovering a low-molecular lignin derivative from the second mixture,

wherein the mixing of the lignin with the phenolic compound is performed at 25° C. to 160° C. to react the lignin and the phenolic compound,
wherein the recovering the low-molecular lignin derivative from the second mixture comprises:
separating a hydrophobic polar solvent layer from the second mixture;
preparing a third mixture by mixing the separated hydrophobic polar solvent layer with a hydrophobic non-polar solvent; and

recovering the precipitated low-molecular lignin derivative from the third mixture.

15. The preparation method according to claim 14 , wherein the hydrophobic non-polar solvent is one or more selected from the group consisting of aromatic hydrocarbons and aliphatic hydrocarbons.

16. The preparation method according to claim 14 , wherein the hydrophobic non-polar solvent is one or more selected from the group consisting of benzene, toluene, xylene, n-hexane, cyclohexane, heptane, and octane.

17. The preparation method according to claim 14 , wherein the hydrophobic non-polar solvent has a dipole moment of less than 0.5 debye.

Assignees

• Cj Cheiljedang Corp

Inventors

• Jung Min Ho
• Moon Sun Joo
• Park Jeung Yil
• Lee Sang Mok
• Kim Da Eun
• Kim Young Ran
• Kim Jung Min
• Chang Jin Hwa

Classifications

• C07G1/00 Primary

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