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Preparation of bonding- affinity composite type polysaccharides chiral stationary phase

A chiral stationary phase, composite technology, applied in chemical instruments and methods, other chemical processes, etc., can solve the problems of low solubility of chiral substances, weak physical coating binding force, low resolution ability, etc., to avoid The loss of chiral selector, the effect of overcoming the low chiral resolution and expanding the scope of use

Inactive Publication Date: 2008-09-10
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The commercial polysaccharide derivative stationary phase uses physical coating method to immobilize polysaccharide derivatives on the chromatographic matrix, but the binding force of physical coating is not strong, and the mobile phase selection range is small, resulting in the separation of chiral substances in the mobile phase. Disadvantages such as low solubility limit its application
In addition, polysaccharide derivatives are also immobilized on the chromatographic matrix by chemical bonding. Although this method improves the solvent resistance of the stationary phase, it reduces the orderly arrangement of polysaccharide derivatives, and the resolution is lower than that of the coating-type chiral phase. Stationary phase (Tomoyuki Ikai, Chiyo Yamamoto, Masami Kamigaito, Yoshio Okamoto., 2007, 1157: 151-158. Bezhan Chankvetadze, Tomoyuki Ikai, Chiyo Yamamoto, Yoshio Okamoto.. Journal of Chromatography A, 2004, 1042: 55-60. Natsuki Kasuyal, Yuko Kusakal, Naoto Habu and Atsushi Ohnishi. Cellulose 9: 263-269, 2002. X M Chen, Y Q Liu, F Qinetal. J. Chromatogr. A, 2003, 1010: 185-19)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Take 1g of cyclodextrin and add it into a reactor filled with 30mL of pyridine, then add 3,5-dichlorophenylisocyanate equivalent to 1.5 times of cyclodextrin, and react at 80°C for 24 hours. After cooling, a large amount of methanol is added to precipitate the product, and after filtration and washing, the product is vacuum-dried to constant weight to obtain the polysaccharide derivative (I), whose hydroxyl substitution degree is 50%; under other conditions unchanged, change 3, The amount of 5-dichlorophenyl isocyanate is 1.87 times that of cyclodextrin to obtain polysaccharide derivative (II) whose hydroxyl substitution degree is 60%.

[0016] Take 1g of polyacrylic acid in a round-bottomed flask, add 10mL of pyridine, swell for 1 hour, add 1.5mL of thionyl chloride, react at 50°C for 8 hours, remove unreacted thionyl chloride, then add 1g of polysaccharides to derivatize Compound (I) and 10mL of acetone, stirred to disperse evenly, and reacted at 80°C for 12 hours. A...

Embodiment 2

[0019] Take 1 g of starch and add it to a reactor containing 20 mL of pyridine, then add 3,5-dimethylphenylisocyanate equivalent to 1.3 times the amount of starch, and react at 100 ° C for 24 hours. After cooling, a large amount of ethanol is added to precipitate the product, and after filtration and washing, the product is vacuum-dried to constant weight to obtain the polysaccharide derivative (I), whose hydroxyl substitution degree is 45%; under other conditions unchanged, change 3, The amount of 5-dimethylphenyl isocyanate is 3.0 times that of starch, and the polysaccharide derivative (II) with a hydroxyl substitution degree of 80% is obtained.

[0020] Take 1g of carboxymethyl cellulose in a round bottom flask, add 10mL of tetrahydrofuran, swell for 8 hours, add 4mL of thionyl chloride, react at 50°C for 8 hours, remove unreacted thionyl chloride, then add 1g of Stir the polysaccharide derivative (I) and 10 mL of tetrahydrofuran to disperse evenly, and react at 50° C. for ...

Embodiment 3

[0023] Take 1g of cellulose and put it into a reactor filled with 15mL of pyridine, then add phenylisocyanate equivalent to 0.9 times the amount of cellulose, and react at 80°C for 24 hours. After cooling, a large amount of methanol was added to precipitate the product, and after filtration and washing, the product was vacuum-dried to constant weight to obtain the polysaccharide derivative (I), whose hydroxyl substitution degree was 39%; The amount of isocyanate used is 5 times that of cellulose, and the polysaccharide derivative (II) with a hydroxyl substitution degree of 95% is obtained.

[0024] Take 1g of carboxylated polystyrene in a round bottom flask, add 10mL of dichloromethane, swell for 12 hours, add 0.75mL of thionyl chloride, react at 40°C for 8 hours, remove unreacted thionyl chloride, and then Add 1 g of polysaccharide derivative (I) and 10 mL of pyridine in sequence, stir to disperse evenly, and react at 80° C. for 12 hours. After cooling, the product was washe...

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PUM

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Abstract

The invention relates to a preparation method for the chiral stationary phase of a bonding-affinity compound polysaccharide. The invention is suitable for the separation and preparation of a chiral enantiomer by liquid chromatography, enlarges the using range of a moving phase and overcomes the defect of poor chiral splitting capacity of a bonding stationary phase. The preparation method is mainly characterized by: 1) chemically bonding a polysaccharide derivatvie I on the stroma of the chiral stationary phase to obtain the bonding stationary phase; 2) coating a polysaccharide derivatvie II on the bonding stationary phase to obtain the chiral stationary phase of a bonding-affinity compound polysaccharide.

Description

technical field [0001] The invention relates to a method for preparing a chiral stationary phase, in particular to a method for synthesizing a bonding-affinity composite polysaccharide chiral stationary phase. Background technique [0002] In the past 20 years, chiral structural compounds have been one of the research hotspots in pharmacology and analytical chemistry. Chiral resolution of enantiomers is an effective means to obtain optically pure substances. Chiral chromatography, especially chiral high-performance liquid chromatography Chromatography is a chiral resolution method developed rapidly in recent years. The core of chiral chromatography is chiral stationary phase (CSPs), so the design and development of CSPs with strong recognition ability, large loading capacity and wide application range has always been the research frontier of chiral chromatography. Among a large number of chiral stationary phases, polysaccharide chiral stationary phases have been proven to h...

Claims

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Application Information

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IPC IPC(8): B01J20/29
Inventor 刘晓宁魏荣卿张晓晓
Owner NANJING UNIV OF TECH
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