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Bonding polysaccharide chiral stationary phase and preparation method thereof

A chiral stationary phase and polysaccharide technology, applied in the field of chiral separation of liquid chromatography, can solve the problems of self-crosslinking, difficult regulation, and high requirements for experimental operation, and achieve long service life, strong solvent resistance, and stable structure Effect

Inactive Publication Date: 2016-12-07
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A variety of bonding methods have been reported at present. However, during the use of the bonding methods reported in the prior art, due to the presence of similar bonding functional groups between polysaccharide derivatives and functionalized chromatographic stationary phase substrates, there are inevitably Problems such as self-crosslinking and difficult regulation, and the bonding methods reported so far have high requirements for experimental operations

Method used

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  • Bonding polysaccharide chiral stationary phase and preparation method thereof
  • Bonding polysaccharide chiral stationary phase and preparation method thereof
  • Bonding polysaccharide chiral stationary phase and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: Preparation of bonded starch benzoate chiral stationary phase

[0037] Take 1 g of starch (amylopectin extracted from corn), add it to a three-necked bottle filled with 10 g of 1-butyl-3-methylimidazolium chloride (BmimCl) ionic liquid, and stir mechanically at 60 °C for 2 hours to obtain a starch / ionic liquid solution . Add 5mL of benzoyl chloride and 0.1mL of acryloyl chloride at the same time, and react for 8 hours. After the reaction system is cooled to room temperature, pour the reaction solution into a large amount of isopropanol to precipitate, separate by filtration, collect the solid, and dry to obtain the bonded starch benzoate derivatives.

[0038] 5 g of pure silica (5 μm, ), dispersed in 50mL of toluene, added 1mL of pyridine, and added 3mL of γ-mercaptopropyltriethoxysilane at the same time, and reacted at 80°C for 12 hours. After the reaction system was cooled to room temperature, it was separated by filtration, and the solid was collecte...

Embodiment 2

[0039] Coat the prepared starch derivatives at 40% (w / w) on the mercapto-containing silica matrix, place it in a 50mL round bottom flask, add 30mL pyridine, 80mg tert-butyl hydroperoxide, 60°C React for 8 hours. After the reaction system is cooled to room temperature, it is separated by filtration, and the solid is collected, and then the solid is thoroughly washed with tetrahydrofuran and methanol, and dried in vacuum. The weight of the obtained product increases, which proves that the starch derivative has been bonded to the carbon dioxide On the silicon substrate, that is to say, a bonded starch benzoate chiral stationary phase was obtained. Example 2: Preparation of bonded cellulose phenyl carbamate chiral stationary phase

[0040] Take 1 g of cellulose (polymerization degree 650), add it into a three-necked flask filled with 20 g of 1-allyl-3-methylimidazolium chloride (AmimCl) ionic liquid, and mechanically stir at 80 ° C for 2 h to obtain a cellulose / ionic liquid solut...

example 3

[0043] Example 3: Preparation of bonded chitosan phenyl carbamate chiral stationary phase

[0044] Take 1g of chitosan (polymerization degree 600-1700), add it into a three-necked bottle filled with 20g of 1-ethyl-3-methylimidazole acetic acid (EmimAc) ionic liquid, and stir mechanically at 40°C for 2h to obtain chitosan / ion Liquid solution, add 0.5mL butylacryloyl chloride, react for 1h, then add 10mL phenylisocyanate, continue to react for 12 hours, wait for the reaction system to cool down to room temperature, pour the reaction solution into a large amount of ethanol, precipitate, separate by filtration, and collect the solid , and dried to obtain chitosan phenyl carbamate derivatives containing double bonds.

[0045] 5 g of pure silica (5 μm, ), dispersed in 50mL of toluene, added 2mL of pyridine, and simultaneously added 5mL of γ-mercaptopropyltrimethoxysilane, reacted at 90°C for 12 hours, cooled the reaction system to room temperature, separated by filtration, collect...

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Abstract

The invention discloses a bonding polysaccharide stationary phase. The bonding polysaccharide stationary phase comprises the following structural general formula (as shown in the description), wherein Q represents a stationary phase substrate; L is -R<2>SCH<2>CH<2>R<3>- or -R<3>CH<2>CH<2>SR<2>-; R<2> and R<3> are separately and independently selected from substituted or unsubstituted alkylidene groups and arylene; m and n are separately and independently selected from 0 and 1; p is an integer between 0 and 8; R<1> and R<5> are separately and independently selected from halogen, alkyl groups and alkoxy groups; and W represents polysaccharide. The bonding polysaccharide stationary phase disclosed by the invention is in chemical bond connection, so that a crosslinking reaction between polysaccharide molecules is avoided, the helical structure of the polysaccharide molecules is furthest reserved, exerting excellent chiral resolution capacity is facilitated, and besides, the solvent resistance is improved.

Description

technical field [0001] The invention belongs to the field of liquid chromatography chiral separation, in particular to a bonded polysaccharide chiral stationary phase prepared by a controllable and efficient method. Background technique [0002] Enantiomer molecules with different optical activities often exhibit different or even opposite biological activities. Therefore, obtaining optically pure single enantiomers is of great significance in the fields of medicine, biology, and materials. Chiral chromatography resolution is the most effective chiral resolution method developed in recent years, the key and core of which is the chromatographic stationary phase with chiral resolution function. Polysaccharide derivatives have good chiral recognition ability and are currently the most widely used, most effective and reliable chiral resolution materials. Loading it on the surface of the chromatographic stationary phase matrix by coating can obtain the currently most commonly us...

Claims

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Application Information

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IPC IPC(8): C08B31/00C08B15/00C08B37/08B01J20/29B01J20/30
Inventor 张军陈韦韦张金明
Owner INST OF CHEM CHINESE ACAD OF SCI
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