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Hybridization chirality stationary phase based on cellulose derivative and preparation method thereof

A technology of cellulose derivatives and chiral stationary phases, applied in chemical instruments and methods, and other chemical processes, can solve the problems of reduced chromatographic processing capacity, limited application, loss of cellulose derivatives, etc., and achieve good chirality Resolving power and mechanical strength, high content of cellulose derivatives, easily controllable effect

Active Publication Date: 2012-07-11
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, due to the limitation of the pore volume of the silica gel used for coating or bonding, generally only about 20 wt% of cellulose derivatives can be bonded or coated, so that the loading capacity of the sample during the preparative chromatographic separation process cannot be further increased, limiting Its Application in Industrial Chromatography
At the same time, the coated cellulose stationary phase can only use a mixture of n-hexane and alcohol organic solvents as the mobile phase, so there may be problems such as low solubility of the enantiomer to be separated in the mobile phase, which greatly reduces the processing capacity of the preparative chromatography , and even greatly reduce the economics of the chromatographic separation process; if organic solvents such as acetone, tetrahydrofuran, and chloroform are added to the mobile phase to improve solubility, it will lead to the loss of cellulose derivatives and the loss of chiral recognition ability
Although bonded cellulose is not easily dissolved or swelled by solvents such as tetrahydrofuran, due to the larger molecular size of cellulose derivatives and the pore structure characteristics of the silica gel carrier itself, the density of chiral functional groups is lower than that of the coated type. Quantity and separation efficiency are not as good as coating type

Method used

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  • Hybridization chirality stationary phase based on cellulose derivative and preparation method thereof
  • Hybridization chirality stationary phase based on cellulose derivative and preparation method thereof
  • Hybridization chirality stationary phase based on cellulose derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] 1) Synthesis of phenylisocyanate cellulose derivative chiral silane monomer

[0031] Put 0.2 g of cellulose, appropriate amount of N, N-dimethylacetamide and appropriate amount of lithium chloride in a three-necked flask, stir and reflux for 1 hour, after the cellulose is dissolved, add 2 ml of anhydrous pyridine, and then add 0.62 g (0.005 mol) a mixture of phenyl isocyanate and 0.05 g (0.0002 mol) tris-(silicon ethoxy) propyl isocyanate, stirred at 80°C for derivatization reaction for 24 hours, and then precipitated the reaction product with 200 ml of methanol, filtered and dried Obtain cellulose derivatives;

[0032] 2) Synthesis of organic-inorganic hybrid silicon balls

[0033] After dissolving 0.1 g of cellulose derivative in tetrahydrofuran at 70°C, adding 2 ml of ethyl orthosilicate and 1 ml of water successively, adding acid to adjust the pH to 2, cross-linking reaction at 60°C for 2 hours, and the resulting mixture Drop into 500 ml of an aqueous solution of sodium ...

Embodiment 2

[0035] 1) Synthesis of 4-chlorophenylisocyanate cellulose derivative chiral silane monomer

[0036] Place 0.2 g of cellulose, appropriate amount of N,N-dimethylacetamide and appropriate amount of lithium chloride in a three-necked flask, stir and reflux at 70°C for 1 hour, and add 2 ml of anhydrous pyridine after the cellulose is dissolved. Then add 1.23 g of 4-chlorophenyl isocyanate (0.008 mol) and 0.05 g (0.0002 mol) of tris-(silicon ethoxy) propyl isocyanate mixture, stir at 80 ℃ for derivatization reaction for 24 hours, then use 200 ml of ethanol The reaction product is precipitated, filtered and dried to obtain a cellulose derivative;

[0037] 2) Synthesis of organic-inorganic hybrid silicon balls

[0038] After dissolving 0.11 g of cellulose derivative in tetrahydrofuran at 70°C, add 4 ml of ethyl orthosilicate and 1 ml of water successively, adjust the pH to 3, cross-link the reaction at 60°C for 2 hours, and drop the reaction mixture into In 500 ml of an aqueous solution o...

Embodiment 3

[0040] 1) Synthesis of chiral silane monomer of p-methylphenyl isocyanate cellulose derivative

[0041] Place 0.2 g of cellulose, appropriate amount of N,N-dimethylacetamide and appropriate amount of lithium chloride in a three-necked flask, stir and reflux at 70°C for 1 hour, and add 2 ml of anhydrous pyridine after the cellulose is dissolved. Then add 0.85 g of p-methylphenyl isocyanate (0.0064 mol) and 0.05 g (0.0002 mol) of tris-(ethoxy silicon) propyl isocyanate mixture, stir at 80 ℃ for derivatization reaction for 24 hours, and then use 200 ml Methanol precipitates the reaction product, filtered and dried to obtain a cellulose derivative;

[0042] 2) Synthesis of organic-inorganic hybrid silicon balls

[0043] After dissolving 0.09 g of cellulose derivative in tetrahydrofuran at 70°C, add 3 ml of ethyl orthosilicate and 1 ml of water successively, adjust the pH to 7, and cross-link the reaction at 60°C for 2 hours. Drop the reaction mixture into 500 ml of an aqueous solution ...

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Abstract

The invention discloses a preparation method of a hybridization chirality stationary phase based on cellulose derivative, which cross-links non-replaced or replaced phenyl isocyanate cellulose derivative with silane coupling agents to prepare hybridization chirality silicon ball stationary phase in a sol-gel method and is simple in operation and easy to control. The prepared cellulose derivative of the hybridization chirality stationary phase is high in content, has good chirality resolution capability and mechanical strength, is good in solvent resistant property, has strong loading capability and is suitable for preparing chromatograph chairality stationary phase.

Description

Technical field [0001] The invention relates to the field of preparation of chiral stationary phases, in particular to a hybrid chiral stationary phase based on cellulose derivatives and a preparation method thereof. Background technique [0002] With the progress and development of medical science, the chromatographic resolution of chiral drugs and the analysis of optical purity have become more and more important. Chiral stationary phase is a chromatographic separation material with enantiomeric resolution and is currently commercially available. There are more than 100 types of chiral stationary phases. Among them, the cellulose-derivatized chiral stationary phase has high resolution performance and chromatographic upload capacity, and is widely used in enantiomeric analysis and separation preparation. [0003] The existing cellulose derivative chiral stationary phase is prepared by derivatizing the cellulose hydroxyl group and coating or bonding it on the surface of a carrier s...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30
Inventor 任其龙翁西伦鲍宗必苏宝根邢华斌杨亦文
Owner ZHEJIANG UNIV
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