Polysaccharide derivative, method for producing the same, and separating agent

Patent metadata

Field	Value
Publication number	US-9458186-B2
Application number	US-201113808717-A
Country	US
Kind code	B2
Filing date	Jul 5, 2011
Priority date	Jul 9, 2010
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

An object of the present invention is to provide a novel polysaccharide derivative used for a separating agent for optical isomers. The novel polysaccharide derivative contains a structure in which a hydrogen atom of a hydroxyl group or an amino group at the 2-position in a structural unit of the polysaccharide is substituted with a monovalent group represented by the following general formula (1), and a hydrogen atom of a hydroxyl group or an amino group at the 3-position in the structural unit is substituted with a monovalent group represented by the following general formula (2):

R 1 —NH—CO—  (1)

R 2 —NH—CO—  (2)

where R 1 and R 2 represent substituted or unsubstituted aryl groups which are different from each other.

First claim

The invention claimed is:

1. A method of producing a product polysaccharide derivative having a structure in which a hydrogen atom of a hydroxyl group or an amino group at the 2-position in a structural unit of a polysaccharide is substituted with a monovalent group represented by the following general formula (1) and a hydrogen atom of a hydroxyl group or an amino group at the 3-position in the structural unit is substituted with a monovalent group represented by the following general formula (2)
R 1 —NH—CO—  (1)

R 2 —NH—CO—  (2)

where R 1 and R 2 represent aryl groups substituted with one or more substituents selected from the group consisting of hydrocarbon groups that have 1 to 12 carbon atoms, which may optionally contain a hetero atom, a cyano group, halogen atoms, a hydroxy group, a nitro group, an amino group, and amino groups having alkyl groups having 1 to 8 carbon atoms as substituents or unsubstituted aryl groups, R 1 and R 2 being different from each other, comprising the steps of:
preparing a solvent mixture comprising a solvent, a raw material polysaccharide derivative in which hydrogen atoms of hydroxyl groups or amino groups at the 2-position, 3-position and 6-position in a structural unit of the polysaccharide are substituted with monovalent groups identical to each other represented by formula (1), and an ionic compound for promoting the dissolution of the raw material polysaccharide derivative in the solvent; and
bringing the solvent mixture into contact with a compound represented by the following general formula (3) to substitute one of the monovalent groups represented by general formula (1) with a monovalent group represented by general formula (2) to form the product polysaccharide derivative,
R 2 —NCO  (3).

Assignees

• Okamoto Yoshio
• Li Junqing
• Shen Xiande
• Shen Jun
• Qu Haitao
• Wu Guangshun
• Daicel Corp

Inventors

• Okamoto Yoshio
• Li Junqing
• Shen Xiande
• Shen Jun
• Qu Haitao
• Wu Guangshun

Classifications

• B01J20/29

  Chiral phases · CPC title

• C08B33/00

  Preparation of derivatives of amylose · CPC title

• C08B15/06

  containing nitrogen {, e.g. carbamates} · CPC title

• B01J20/285 Primary

  based on polymers · CPC title

• B01J2220/4825

  Polysaccharides or cellulose materials, e.g. starch, chitin, sawdust, wood, straw, cotton · CPC title