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 r

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0014] Example 1

[0015] Take 1 g of cyclodextrin and put it into a reactor containing 30 mL of pyridine, then add 3,5-dichlorophenyl isocyanate equivalent to 1.5 times the amount of cyclodextrin, 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 50%; under other conditions unchanged, change 3, The amount of 5-dichlorophenyl isocyanate used is 1.87 times that of cyclodextrin, that is, the polysaccharide derivative (II) whose hydroxyl substitution degree is 60% is obtained.

[0016] Take 1 g of polyacrylic acid into a round-bottomed flask, add 10 mL of pyridine, swell for 1 hour, add 1.5 mL of thionyl chloride, react at 50°C for 8 hours, remove the unreacted sulfoxide chloride, and then add 1 g of polysaccharide derivative Compound (I) and 10 mL of ac...

Example Embodiment

[0018] Example 2

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

[0020] Take 1 g of carboxymethyl cellulose into a round-bottomed flask, add 10 mL of tetrahydrofuran, swell for 8 hours, add 4 mL of thionyl chloride, react at 50°C for 8 hours, remove the unreacted sulfoxide chloride, and then add 1 g The polysaccharide derivative (I) and 10 mL of tetrahydrofuran were stirred to disperse uniformly, and reacted...

Example Embodiment

[0022] Example 3

[0023] Take 1 g of cellulose and add it to a reactor containing 15 mL of pyridine, then add phenyl isocyanate 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 a constant weight to obtain the polysaccharide derivative (I) whose hydroxyl substitution degree was 39%; When the amount of isocyanate is 5 times that of cellulose, the polysaccharide derivative (II) is obtained with a hydroxyl substitution degree of 95%.

[0024] Take 1 g of carboxylated polystyrene into a round-bottomed flask, add 10 mL of dichloromethane, swell for 12 hours, add 0.75 mL of thionyl chloride, and react at 40°C for 8 hours. 1 g of the polysaccharide derivative (I) and 10 mL of pyridine were sequentially added, stirred to disperse uniformly, and reacted at 80° C. for 12 hours. After cooling, the product is ...

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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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