Unlock instant, AI-driven research and patent intelligence for your innovation.

Separating agent for optical isomer

a technology of optical isomers and separation agents, which is applied in the field of separation agents for optical isomers, can solve the problems of difficult separation of large amounts of optical isomers in one stroke with the filler, low mechanical strength of the separation agent for optical isomers, and limited amount of polymer compound derivatives which the inorganic carrier can carry on itself, etc., and achieve excellent solvent resistance, suppress swelling and contraction of the separation agent, and high mechanical strength

Inactive Publication Date: 2010-04-22
NAGOYA UNIVERSITY +1
View PDF16 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0022]The complex according to the present invention obtained by the following procedure is extremely useful as a high-performance material, and is effectively used particularly in the production of a separating agent for use in the separation of optical isomers: a polymer compound derivative modified with a compound represented by the above general formula (I) and one or more kinds of compounds represented by the above general formulae (II) to (V) are caused to react with each other.
[0023]When the complex of the present invention is used in a separating agent for use in the separation of optical isomers, the separating agent can separate large amounts of the optical isomers in one stroke because a ratio of the molecules of the polymer compound derivative that contribute to the separation of the optical isomers in the complex is large.
[0024]In addition, when the complex of the present invention is used in a separating agent for use in the separation of optical isomers, the separating agent shows a high mechanical strength because the complex contains a three-dimensionally crosslinked inorganic substance.
[0025]In addition, the polymer compound derivative and the three-dimensionally crosslinked inorganic substance are chemically bonded to each other in the complex of the present invention, so even a solvent that may dissolve the polymer compound derivative can be used, and the complex is excellent in solvent resistance.
[0026]In addition, when the complex of the present invention is used in a separating agent for use in the separation of optical isomers, the swelling and contraction of the separating agent are suppressed, and the separating agent is suitable not only for the analysis of the optical isomers but also for an application where the optical isomers are separated because the complex contains a compound having a functional group that reacts with an alkoxysilyl group.

Problems solved by technology

In addition, it is difficult to separate large amounts of optical isomers in one stroke with the filler because only the molecules of the polymer compound present at the surface on the inorganic carrier contribute to optical resolution.
However, the amount of the polymer compound derivative which the inorganic carrier can carry on itself is limited, and there has been room for further development of a separating agent optimum for the separation of large amounts of optical isomers.
However, any such separating agent for optical isomers has a low mechanical strength, and its use under high pressures at high flow rates is restricted because the separating agent is formed only of an organic compound.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Separating agent for optical isomer
  • Separating agent for optical isomer
  • Separating agent for optical isomer

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0125](1-1) Synthesis of Cellulose 3,5-dimethylphenylcarbamate having Alkoxysilyl Groups

[0126]First, 4.00 g (24.7 mmol) of dried cellulose were dissolved in a mixed solution of 120 ml of dehydrated N,N-dimethylacetamide, 60 ml of dehydrated pyridine, and 8.00 g of lithium chloride.

[0127]Then, 9.08 g (61.8 mmol) of 3,5-dimethylphenyl isocyanate were added to the resultant solution, and the mixture was subjected to a reaction at 80° C. for 15 hours. After that, 0.52 g (2.1 mmol) of 3-isocyanatepropyltriethoxysilane was added to the resultant, and the mixture was subjected to a reaction at 80° C. for 12 hours. Further, 9.08 g (61.8 mmol) of 3,5-dimethylphenyl isocyanate were added to the resultant, and the mixture was subjected to a reaction at 80° C. for 11 hours. A pyridine soluble portion was dropped into methanol and recovered as an insoluble portion. After that, the portion was dried in a vacuum. As a result, 13.13 g of a cellulose 3,5-dimethylphenylcarbamate derivative A into whi...

example 2

[0142](2-1) Synthesis of Cellulose 3,5-dimethylphenylcarbamate having Alkoxysilyl Groups

[0143]First, 4.00 g (24.7 mmol) of dried cellulose were dissolved in a mixed solution of 120 ml of dehydrated N,N-dimethylacetamide, 60 ml of dehydrated pyridine, and 8.00 g of lithium chloride.

[0144]Then, 9.08 g (61.8 mmol) of 3,5 -dimethylphenyl isocyanate were added to the resultant solution, and the mixture was subjected to a reaction at 80° C. for 15 hours. After that, 0.34 g (1.4 mmol) of 3-isocyanatepropyltriethoxysilane was added to the resultant, and the mixture was subjected to a reaction at 80° C. for 12 hours. Further, 9.08 g (61.8 mmol) of 3,5-dimethylphenyl isocyanate were added to the resultant, and the mixture was subjected to a reaction at 80° C. for 11 hours. A pyridine soluble portion was dropped into methanol and recovered as an insoluble portion. After that, the portion was dried in a vacuum. As a result, 13.29 g of a cellulose 3,5-dimethylphenylcarbamate derivative B into wh...

example 3

[0153](3-1) Synthesis of Cellulose 3,5-dimethylphenylcarbamate having Alkoxysilyl Groups

[0154]First, 0.50 g (3.09 mmol) of dried cellulose was dissolved in a mixed solution of 15 ml of dehydrated N,N-dimethylacetamide, 7.5 ml of dehydrated pyridine, and 1.00 g of lithium chloride.

[0155]Then, 1.13 g (7.72 mmol) of 3,5-dimethylphenyl isocyanate were added to the resultant solution, and the mixture was subjected to a reaction at 80° C. for 6 hours. After that, 84 mg (0.34 mmol) of 3-isocyanatepropyltriethoxysilane was added to the resultant, and the mixture was subjected to a reaction at 80° C. for 13 hours. Further, 1.36 g (9.26 mmol) of 3,5-dimethylphenyl isocyanate were added to the resultant, and the mixture was subjected to a reaction at 80° C. for 7 hours. A pyridine soluble portion was dropped into methanol and recovered as an insoluble portion. After that, the portion was dried in a vacuum. As a result, 1.65 g of a cellulose 3,5-dimethylphenylcarbamate derivative C into which a...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Fractionaaaaaaaaaa
Ratioaaaaaaaaaa
Optical activityaaaaaaaaaa
Login to View More

Abstract

Provided is a complex obtained by reacting a polymer compound derivative obtained by modifying part of hydroxy groups or amino groups of a polymer compound having the hydroxy groups or amino groups with a compound represented by the following general formula (I) with one or more kinds of compounds represented by the following general formulae (II) to (V): (I) A-X—Si(Y)nR3-n (where A, X, Y, R, and n are as defined in claim 1) ; (II) M(OR1)nR24-n; (III) Al(OR1)pR23-p; (IV) Mg(OR1)gR22-q (where M, R1, R2, n, p, and q are as defined in claim 1); and (V) (where R3, R4, R5, and R6 are as defined in claim 1).

Description

TECHNICAL FIELD[0001]The present invention relates to a complex used in a separating agent for optical isomers.BACKGROUND ART [0002]It has recently become more and more important to obtain large amounts of optical isomers in a short time period with ease in terms of the research and development of drugs and high-performance materials.[0003]Optical resolution by chromatography has conventionally been attracting attention remarkably in various fields including analytical chemistry, organic chemistry, medicine, and pharmacy, and a large number of chiral stationary phases have been reported in the world. In particular, for example, an ester derivative or carbamate derivative obtained by chemically modifying a polysaccharide such as cellulose or amylose as an optically active polymer serves as a chiral stationary phase having a high optical resolution, and a filler for chromatography using such derivative has been known to the public. A filler for chromatography using such polymer compou...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C08B3/14C08B1/00C08B33/00
CPCB01J20/265B01J20/285C08B33/00B01J20/29C08B15/05B01J20/286C08B3/14C08B33/02G01N30/88
Inventor OKAMOTO, YOSHIOYAMAMOTO, CHIYOIKAI, TOMOYUKIKAMIGAITO, MASAMI
Owner NAGOYA UNIVERSITY