Preparation method and application of ethanediamine-bridged double-beta-cyclodextrin bonded SBA-15 chiral stationary phase

A technology of chiral stationary phase and ethylenediamine bridge, which is applied in separation methods, chemical instruments and methods, solid adsorbent liquid separation, etc., can solve the problems that the separation function of chiral chromatography has yet to be developed and utilized, and achieve the improvement of chirality Separation ability, high practicality, low price effect

Inactive Publication Date: 2015-01-21
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the research on bicycline as an artificial imitation enzyme has been relatively in-depth, but its chiral chromatographic separation function has yet to be developed and utilized.

Method used

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  • Preparation method and application of ethanediamine-bridged double-beta-cyclodextrin bonded SBA-15 chiral stationary phase
  • Preparation method and application of ethanediamine-bridged double-beta-cyclodextrin bonded SBA-15 chiral stationary phase
  • Preparation method and application of ethanediamine-bridged double-beta-cyclodextrin bonded SBA-15 chiral stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Take SBA-15 (400 m 2 / g) 4.0 g of activated silica gel is the substrate;

[0031] (1) Under a nitrogen atmosphere, according to the ratio of β-cyclodextrin (mmol): anhydrous pyridine A (mL): p-toluenesulfonyl chloride (mmol): anhydrous pyridine B (mL) 1:10:0.6:2.5 Dissolve β-cyclodextrin and p-toluenesulfonyl chloride in the corresponding amount of anhydrous pyridine, and add the solution of p-toluenesulfonyl chloride in anhydrous pyridine B dropwise to β-cyclodextrin within 2 h under stirring. Pyridine A solution in water, stirred and reacted at room temperature for 11 h to obtain a yellow solution, removed pyridine in vacuo, added anhydrous ether to obtain a white solid, filtered the solid and recrystallized several times with ultrapure water to obtain (6-oxo-p-toluene Sulfonyl)-β-cyclodextrin intermediate (I);

[0032] (2) Under nitrogen atmosphere, according to (6-oxo-p-toluenesulfonyl)-β-cyclodextrin intermediate (I) (mmol): anhydrous pyridine (mL): ethylenediami...

Embodiment 2

[0039] Take SBA-15 (500 m 2 / g) 4.0 g of activated silica gel is the substrate;

[0040] (1) Under a nitrogen atmosphere, according to the ratio of β-cyclodextrin (mmol): anhydrous pyridine A (mL): p-toluenesulfonyl chloride (mmol): anhydrous pyridine B (mL) at 1:12:0.9:3.0 Dissolve β-cyclodextrin and p-toluenesulfonyl chloride in the corresponding amount of anhydrous pyridine, and add the solution of p-toluenesulfonyl chloride in anhydrous pyridine B dropwise to β-cyclodextrin within 3 h under stirring. Pyridine A solution in water, stirred and reacted at room temperature for 13 h to obtain a yellow solution, removed pyridine in vacuo, added anhydrous ether to obtain a white solid, filtered the solid and recrystallized several times with ultrapure water to obtain (6-oxo-p-toluene Sulfonyl)-β-cyclodextrin intermediate (I);

[0041] (2) Under nitrogen atmosphere, according to (6-oxo-p-toluenesulfonyl)-β-cyclodextrin intermediate (I) (mmol): anhydrous pyridine (mL): ethylenedi...

Embodiment 3

[0048] Take SBA-15 (465 m 2 / g) 4.0 g of activated silica gel is the substrate;

[0049] (1) Under nitrogen atmosphere, according to β-cyclodextrin (mmol): anhydrous pyridine A (mL): p-toluenesulfonyl chloride (mmol): anhydrous pyridine B (mL) is 1:11:0.7:2.7 Dissolve β-cyclodextrin and p-toluenesulfonyl chloride in the corresponding amount of anhydrous pyridine, and add the solution of p-toluenesulfonyl chloride in anhydrous pyridine B dropwise to β-cyclodextrin within 2.5 h under stirring. Pyridine A solution in water, stirred and reacted at room temperature for 12 h to obtain a yellow solution, removed pyridine in vacuo, added anhydrous ether to obtain a white solid, filtered the solid and recrystallized several times with ultrapure water to obtain (6-oxo-p-toluene Sulfonyl)-β-cyclodextrin intermediate (I);

[0050] (2) Under nitrogen atmosphere, according to (6-oxo-p-toluenesulfonyl)-β-cyclodextrin intermediate (I) (mmol): anhydrous pyridine (mL): ethylenediamine (mL) as...

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Abstract

The invention relates to a chiral stationary phase. The chiral stationary phase is prepared by the steps: in an anhydrous solvent, preparing a (6-oxy-p-toluenesulfonyl)-beta-cyclodextrin intermediate (I) from beta-cyclodextrin; reacting the (6-oxy-p-toluenesulfonyl)-beta-cyclodextrin with ethidenediamine so as to obtain a (6-deoxy-ethanediamine)-beta-cyclodextrin intermediate (II) by adopting anhydrous pyridine as a solvent; bonding the (I) onto the surface of ordered mesoporous SBA-15 silica gel by adopting anhydrous N, N-dimethylformamide as a solvent and using 3-carbimide triethoxypropylsilane as a coupling agent, so as to obtain a (6-oxy-p-toluenesulfonyl)-beta-cyclodextrin bonded SBA-15 silica gel intermediate (III); and dispersing the (III) in the anhydrous N, N-dimethylformamide by adopting a continuous reaction method and adding the (II) for reaction so as to obtain the chiral stationary phase. The preparation method is simple, relatively low in cost and wide in applicability.

Description

technical field [0001] The invention relates to a preparation method and application of a bonded SBA-15 silica gel chiral stationary phase, especially a bonded SBA-15 silica gel chiral stationary phase with ethylenediamine bridged double β-cyclodextrin as a ligand Preparation method and chiral separation application. Background technique [0002] Chirality is a basic property of nature, which refers to the property that a substance and its mirror image cannot overlap. Chirality is closely related to our daily life and health, because there are often significant differences in the metabolism and pharmacological effects of chiral drug enantiomers in organisms. Among the clinically used drugs, chiral drugs account for the vast majority, but most of the chiral drugs are still produced, sold and used as racemates, and the safety of drugs cannot be guaranteed. For example, β-blockers are a common class of important drugs for the treatment of arrhythmia, angina pectoris, myocardi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/26B01J20/30B01D15/38C08B37/16
CPCB01J20/26B01D15/3833B01J20/3085B01J2220/54C08B37/0012
Inventor 李来生周仁丹程彪平李良聂桂珍张宏福
Owner NANCHANG UNIV
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