# US 2018/0022832 A1 · Method for producing polysaccharide derivative and lignin derivative

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- Number: US 2018/0022832 A1
- Document ID: US20180022832A1
- Status: Published application
- Kind: A1
- Application number: 15/521,200
- Filed: 2015-10-23
- Published: 2018-01-25
- Earliest claimed: 2014-10-27
- Assignees: National University Corporation Kanazawa University; Kanazawa Institute of Technology
- Applicants: National University Corporation Kanazawa University; Kanazawa Institute of Technology
- Inventors: Ryohei KAKUCHI; Kazuaki NINOMIYA; Yoshiki SHIBATA; Kiyoshi UZAWA; Tomoki OGOSHI; Katsuhiro MAEDA; Tomoyuki IKAI; Kenji TAKAHASHI
- Web page: https://patentgrep.com/patent/US20180022832A1

## CPC

- C08B 3/06: Cellulose acetate {, e.g. mono-acetate, di-acetate or tri-acetate}
- C07G 1/00: Low-molecular-weight derivatives of lignin (high-molecular-weight derivatives of lignin {C08H6/00})
- C08B 3/00: Preparation of cellulose esters of organic acids {(rendering cellulose suitable for esterification C08B1/02)}
- C08B 3/18: Aceto-butyrates
- C08B 11/00: Preparation of cellulose ethers {(rendering cellulose suitable for etherification C08B1/06)}
- C08B 11/02: Alkyl or cycloalkyl ethers
- C08H 6/00: {Macromolecular compounds derived from lignin, e.g. tannins, humic acids}
- C08L 97/005: {Lignin}
- C08L 97/02: Lignocellulosic material, e.g. wood, straw or bagasse {(manufacture of articles made from lignocellulosic material by dry processes B27N)}
- Y02P 20/54: using solvents, e.g. supercritical solvents or ionic liquids
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- C07G: COMPOUNDS OF UNKNOWN CONSTITUTION (sulfonated fats, oils or waxes of undetermined constitution C07C309/62)
- C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

An object is to provide a method for producing a polysaccharide derivative without using a catalyst, a cocatalyst, or an active compound by esterification, etherification, or the like, from a polysaccharide such as cellulose as a source material, while maintaining a high molecular weight. Another object is to provide a method for producing a cellulose derivative in a separated condition directly from biomass containing lignocellulose. A method for producing a polysaccharide derivative of the present invention is characterized in that a reaction is carried out in a mixture comprising: a source material comprising a polysaccharide; an ionic liquid for which the pKa of a conjugate acid of an anion in DMSO is 12 to 19 and which is capable of producing a carbene; and a chain or cyclic ester compound or an epoxy compound. Preferably as a source material containing a polysaccharide, a biomass source material containing lignocellulose is used.

## Claims

### Claim 1

A method for producing a cellulose derivative, wherein a reaction is carried out without particularly using a catalyst in a mixture comprising: a biomass source material comprising cellulose as lignocellulose; an ionic liquid in which a cation is represented by the following Formula (1):
wherein, R1 and R2 each independently are an alkyl group, an alkenyl group, an alkoxyalkyl group, or a substituted or unsubstituted phenyl group, and R3 to R5 each independently are hydrogen, an alkenyl group, an alkoxyalkyl group, or a substituted or unsubstituted phenyl group,
for which the pKa of a conjugate acid of an anion in DMSO is 12 to 19 and which is capable of producing a carbene; and a chain or cyclic ester compound.

### Claim 2

(canceled)

### Claim 3 (depends on 1)

The method for producing a cellulose derivative according to claim 1, wherein a cellulose derivative is produced in a condition separated from a lignin.

### Claim 4 (depends on 3)

The method for producing a cellulose derivative according to claim 3, wherein the cellulose derivative is produced, and also a lignin derivative is produced.

### Claim 5 (depends on 1)

The method for producing a cellulose derivative according to claim 1, wherein the ionic liquid is included in the mixture as a cosolvent system with an organic solvent.

### Claim 6 (depends on 1)

The method for producing a cellulose derivative according to claim 1, wherein the weight of the ionic liquid is two times or more of the weight of the cellulose.

### Claim 7 (depends on 1)

The method for producing a cellulose derivative according to claim 1, wherein 2 or more chain or cyclic ester compounds are included in the mixture.

### Claim 8 (depends on 1)

The method for producing a cellulose derivative according to claim 1, wherein the chain ester compound is a carboxylate ester selected from the group consisting of isopropenyl carboxylate, vinyl carboxylate, and methyl carboxylate.

### Claim 9

(canceled)

### Claim 10 (depends on 1)

The method for producing a cellulose derivative according to claim 1, wherein an anion of the ionic liquid is a carboxylate anion.

### Claim 11

A method for producing a lignin derivative, wherein a reaction is carried out without particularly using a catalyst in a mixture comprising: a source material comprising a lignin; an ionic liquid in which a cation is represented by the following Formula (1):
wherein, R1 and R2 each independently are an alkyl group, an alkenyl group, an alkoxyalkyl group, or a substituted or unsubstituted phenyl group, and R3 to R5 each independently are hydrogen, an alkenyl group, an alkoxyalkyl group, or a substituted or unsubstituted phenyl group,
for which the pKa of a conjugate acid of an anion in DMSO is 12 to 19 and which is capable of producing a carbene; and a chain or cyclic ester compound.

### Claim 12 (depends on 11)

The method for producing a lignin derivative according to claim 11, wherein 2 or more chain or cyclic ester compounds are included in the mixture.

### Claim 13 (depends on 11)

The method for producing a lignin derivative according to claim 11, wherein the chain ester compound is a carboxylate ester selected from the group consisting of isopropenyl carboxylate, vinyl carboxylate, and methyl carboxylate.

### Claim 14

(canceled)

### Claim 15 (depends on 11)

The method for producing a lignin derivative according to claim 11, wherein an anion of the ionic liquid is a carboxylate anion.
