Non-particulate organic porous material having optical resolution capability and method for manufacturing same

a non-particulate organic porous material and optical resolution technology, applied in the direction of filtration separation, other chemical processes, separation processes, etc., can solve the problems of deterioration of separation performance during continuous operation, small adsorption capacity, and difficult to achieve precise separation, etc., to achieve excellent optical separation capability, limited separation performance, and high physical stability

Inactive Publication Date: 2005-07-21
ORGANO CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013] The present invention (4) provides a method for manufacturing the second non-particulate organic porous material comprising preparing a mixture of an oil-soluble monomer containing optically active groups, a surfactant, and water, stirring the mixture to prepare a water-in-oil-type emulsion, allowing the mixture to stand to polymerize the monomer, and causing a part or all of the optically active groups to be eliminated.
[0014] Since the non-particulate organic porous material of the present invention has high physical stability, can be used under a wide variety of separating conditions, and possesses an excellent capability of separating optically active substances, the material is free from the shortcomings to the conventional optical resolution column

Problems solved by technology

This use of fine particles requires a significantly high operating pressure that may lead to deterioration of the separation performance during continuous operation for a long period of time as these adsorbents exhibit poor physical stability.
However, the chiral sorbent having a molded porous ceramic as a substrate disclosed in the Published Japanese translation of PCT Application No. 2000-515627 has a drawback of

Method used

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  • Non-particulate organic porous material having optical resolution capability and method for manufacturing same
  • Non-particulate organic porous material having optical resolution capability and method for manufacturing same

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

Preparation of 4-(−)-pinanyldimethyl silylstyrene (Abbreviated to (−)-PSSt)

[0043] 28.4 g of p-dibromobenzene was dissolved in diethyl ether, and 51.3 g n-butyl lithium was added to react with p-dibromobenzene at 0° C. Then, 31.2 g of (−)-pinanyldimethylsilyl chloride was added and reacted. A mixture obtained after a routine process was purified by distillation under reduced pressure to obtain 1-bromo-4-(−)-pinanyldimethylsilylbenzene. After dissolving 34.85 g of the obtained 1-bromo-4-(−)-pinanyldimethylsilylbenzene in diethyl ether, 42.4 g of n-butyl lithium and 6.9 g of dimethylformamide were successively added and the mixture was reacted. After processing by a routine method, the reaction mixture was purified by silica gel column chromatography to obtain 27.4 g of 4-(−)-pinanyldimethylsilylbenzaldehyde. After dissolving the obtained aldehyde in 200 ml of tetrahydrofuran, the solution was added to a solution of 36.9 g of methyltriphenyl iodide and 40.0 g of n-butyl lithium to ob...

preparation example 2

Preparation of (−)-menthyl 4-vinylbenzoate (Abbreviated to (−)-MtSt)

[0044] 14.8 g of 4-vinylbenzoic acid was dissolved in methylene chloride and reacted with 15.6 g of (−)-menthol, using an N,N′-dicyclohexyl carbodiimide as a condensing agent to obtain (−)-MtSt. The (−)-MtSt was purified by silica gel column chromatography using a hexane / ethyl acetate mixture (19 / 1) as a developing solvent to obtain 20.3 g of purified (−)-MtSt. The structure was confirmed using NMR and IR.

example 1

Preparation of Non-Particulate Organic Porous Material having Optically Active Groups by Introducing (−)-pinanyldimethylsilyl Groups.

[0045] 6.8 g of (−)—PSSt, 2.9 g of divinylbenzene, 1.1 g of sorbitan monooleate, and 0.10 g of azobis-iso-butylonitrile were mixed. A container for emulsion preparation was charged with the mixture and 97 g of deionized water. The resultant mixture was stirred using a sun-and-planettype stirrer (vacuum agitation defoaming mixer, manufactured by EME Co., Ltd.) at a reduced pressure of 13.3 kPa, at a revolution rate (rotation around a revolution axis) of 2,000 rpm, and at a rotation of 600 rpm for 2.5 minutes to obtain a water-in-oil emulsion. After the emulsification, the reaction system ambience was sufficiently replaced with nitrogen and the emulsion was sealed and allowed to stand to polymerize at 60° C. for 24 hours. After the polymerization, the reaction mixture was extracted with isopropanol for 18 hours using a Soxhlet extractor to remove unrea...

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Abstract

A non-particulate organic porous material with optical resolution capability, the non-particulate organic porous material having a continuous pore structure, which comprises macropores and mesopores, the macropores being interconnected forming mesopores with a radius of 0.01-100 μm in the interconnected parts, and optically active groups uniformly introduced therein possesses high physical stability, can be used under wide separating conditions, and has a large capacity for separating optically active substances (enantiometers).

Description

TECHNICAL FIELD [0001] The present invention relates to a non-particulate organic porous material having optical resolution capability that can separate enantiomers, and a method for manufacturing the same. BACKGROUND ART [0002] Many compounds with a chiral molecular structure that contain enantiomers are physiologically active and important as raw materials of drugs, agricultural chemicals, and food additives. In general, many enantiomers have completely different physiology activities from enantiomers of the same constituent elements in the same proportion by weight. For example, in the case of thalidomide, the R(−) enantiomer has a sedative effect and the S(−) enantiomer is teratogenic. For this reason, there has recently been an increasing demand for optical resolution of enantiomers, particularly in the pharmaceutical industry. [0003] As the method for optical resolution of enantiomers, a preferential crystallization method in which one of the enantiomers is preferentially crys...

Claims

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Application Information

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IPC IPC(8): B01J20/26B01D39/00B01D39/16
CPCB01D39/1676B01D15/3852B01D15/3833C08J9/36
Inventor TERAGUCHI, MASAHIROKANEKO, TAKASHIAOKI, TOSHIKIINOUE, HIROSHIYOSHIDA, AKIKO
Owner ORGANO CORP
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