Preparation method for beta-cyclodextrin chiral stationary phase

A chiral stationary phase, cyclodextrin technology, applied in chemical instruments and methods, other chemical processes, etc., can solve the problems of difficult purification of the reaction, tailing of high performance liquid chromatography peaks, shortened column life, etc. Elution, Ease of Derivatization, Ease of Operation

Inactive Publication Date: 2014-02-26
BEIJING UNIV OF CHEM TECH
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  • Application Information

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Problems solved by technology

Ning Zhong et al reported in "Tetrahedron Letters, 1998: 2919-2920" that "under the condition of 10% sodium hydroxide solution, a single-(6-O-tolylsulfonyl)-β-cyclodextrin was synthesized , the yield reaches 61%", the disadvantage is that the introduction of metal ions w...

Method used

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  • Preparation method for beta-cyclodextrin chiral stationary phase
  • Preparation method for beta-cyclodextrin chiral stationary phase
  • Preparation method for beta-cyclodextrin chiral stationary phase

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Add 7.5g of activated silica gel and 70mL of anhydrous toluene into a 100mL three-necked flask, heat and reflux with a water separator to remove water for 0.5h, then add 4.2mL of 3-aminopropyltriethoxysilane dropwise, and at 100°C The reaction was stirred for 4h. After cooling to room temperature and washing with anhydrous toluene for 5 times, 2.3 mL of trimethylchlorosilane was added dropwise, and the reaction was stirred at 50° C. for 4 h. Cool to room temperature, wash 5 times with anhydrous toluene, take samples and make elemental analysis. Calculate and weigh 3.0g 4,4'-diphenylmethane diisocyanate and add it to the reaction system, 2 , stirred and reacted at 80°C for 6h, cooled to room temperature, and washed 5 times with anhydrous toluene. Calculate and weigh 5.5g β-CD and add it to the reaction system, feed N 2 , Stir the reaction at 80°C for 8h. After cooling to room temperature, it was washed twice with anhydrous toluene, twice with acetone, and three times...

Embodiment 2

[0042] Add 5g of activated silica gel and 70mL of anhydrous toluene into a 100mL three-necked flask, heat and reflux with a water separator and stir to remove water for 0.5h, then add 3.4mL of 3-aminopropyltriethoxysilane dropwise, and stir at 100°C Reaction 4h. After cooling to room temperature and washing with anhydrous toluene for 5 times, 1.8 mL of trimethylchlorosilane was added dropwise, and the reaction was stirred at 50° C. for 4 h. Cool to room temperature, wash 5 times with anhydrous toluene, take samples and make elemental analysis. Calculate and weigh 1.1g 4,4'-diphenylmethane diisocyanate and join in the reaction system, pass into N 2 , stirred and reacted at 80°C for 6h, cooled to room temperature, and washed 5 times with anhydrous toluene. Calculate and weigh 3.9g β-CD and add it to the reaction system, feed N 2 , Stir the reaction at 80°C for 8h. After cooling to room temperature, it was washed twice with anhydrous toluene, twice with acetone, and three tim...

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Abstract

A disclosed preparation method for a beta-cyclodextrin chiral stationary phase comprises: taking SiO2 microballoons as a raw material, and bonding beta-cyclodextrin (beta-CD) to the surface of SiO2 microballoons by employing 3-aminopropyltriethoxysilane (KH550), trimethylchlorosilane and 4,4'-methylenediphenyl diisocyanate (MDI) to obtain the beta-cyclodextrin chiral stationary phase. The method has continuity, simple operation and short synthetic period, and the synthetic product is convenient to be subjected to derivatization; no metal ion-containing catalysts such as NaOH, NaN3, CuI(PPh3) and the like are introduced according to the method, so that the chiral stationary phase is prevented from pollution, and the method relatively accords with the separation requirement of high-purity liquid chromatogram. The method is applicable to separation of benzene ring-containing chiral medicament intermediates and pyrethroid pesticide compounds.

Description

technical field [0001] The invention relates to a preparation technology of a high-performance liquid chromatography (HPLC) column packing chiral stationary phase, in particular to a preparation method of a beta-cyclodextrin chiral stationary phase. Background technique [0002] From 1953 to 1961, the "thalidomide"-"reaction stop" teratogenic event resulted in the birth of about 12,000 seal babies. Chiral resolution and purification have entered the market. The "reactive stopping event" has attracted great attention from the international community, and has also triggered an upsurge in research on chiral separation in the scientific community. On January 5, 1992, the U.S. Food and Drug Administration (FDA) stipulated that when reporting chiral drugs, the quantity and relative content of each isomer in the samples used in pharmacological, toxicological and clinical research must be clearly stated . High-performance liquid chromatography (HPLC) using chiral stationary phase...

Claims

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Application Information

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IPC IPC(8): C08B37/16B01J20/29B01J20/30
Inventor 杨俊佼彭秋瑾
Owner BEIJING UNIV OF CHEM TECH
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