Synthesis and application of large-grain diameter chiral stationary phase

A chiral stationary phase and large particle size technology, which is applied in the preparation of organic compounds, preparation of amino hydroxyl compounds, organic chemistry, etc., can solve the problems of undiscovered synthesis and application, and achieve the prevention of high column pressure, good application prospects, Good chiral separation effect

Inactive Publication Date: 2011-11-09
王荣
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above-mentioned patents are mainly based on silica gel, and the particle size is 5 μm, but there is no patent application for the synthesis and application of >5 μm fillers for chiral fillers.

Method used

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  • Synthesis and application of large-grain diameter chiral stationary phase
  • Synthesis and application of large-grain diameter chiral stationary phase
  • Synthesis and application of large-grain diameter chiral stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 A chiral stationary phase with a large particle size, the chiral stationary phase is a coated and bonded cellulose derivative chiral stationary phase with a coating volume ratio of 20%, which has the following structural formula,

[0034]

[0035] The synthetic method of this large particle size chiral stationary phase comprises the following steps:

[0036] (1) Synthesis of aminopropyl alkylated silica gel (APS) (see figure 1 ): Firstly, after the silica gel with a particle size of 40-60 μm is activated by hydrochloric acid with a mass concentration of 3.65%, it is placed in a 250mL three-necked bottle and dried in a BPZ-6033LC vacuum oven at 180°C for 5 hours to obtain activated silica gel; N 2 Under protection, add anhydrous benzene, anhydrous pyridine and 3-aminopropyltriethoxysilane in turn, and use a three-necked flask to reflux at 80°C for 22 hours; finally cool to room temperature, and use 500mL methanol, 500mL acetone, Wash it with n-hexane, and ...

Embodiment 2

[0056] Example 2 A chiral stationary phase with a large particle size, the chiral stationary phase is a coated and bonded cellulose derivative chiral stationary phase with a coating volume ratio of 18%, and its structural formula is the same as that of Example 1.

[0057] The synthetic method of this large particle size chiral stationary phase comprises the following steps:

[0058] (1) Synthesis of aminopropyl alkylated silica gel (APS): firstly, silica gel with a particle size of 40-60 μm was activated by hydrochloric acid with a mass concentration of 3.65%, and placed in a 250mL three-necked bottle at 150°C using BPZ- 6033LC vacuum drying oven vacuum drying 6h, get activated silica gel; then in N 2 Under protection, add anhydrous benzene, anhydrous pyridine and 3-aminopropyltriethoxysilane in sequence, and reflux reaction at 85°C for 20h; finally cool to room temperature, wash with 500mL methanol, 500mL acetone, and 500mL n-hexane respectively, Vacuum-dried at 60°C for 6 h...

Embodiment 3

[0066] Example 3 A chiral stationary phase with a large particle size, the chiral stationary phase is a coated and bonded cellulose derivative chiral stationary phase with a coating volume ratio of 25%, and its structural formula is the same as that of Example 1.

[0067] The synthetic method of this large particle size chiral stationary phase comprises the following steps:

[0068] (1) Synthesis of aminopropyl alkylated silica gel (APS): firstly, silica gel with a particle size of 40-60 μm was activated by hydrochloric acid with a mass concentration of 3.65%, and then placed in a 250 mL three-necked bottle and vacuum-dried at 200 ° C for 4 h , to get activated silica gel; then in N 2 Under protection, add anhydrous benzene, anhydrous pyridine and 3-aminopropyltriethoxysilane in sequence, and reflux at 75°C for 24 hours; finally cool to room temperature, wash with 500mL methanol, 500mL acetone, and 500mL n-hexane respectively, Vacuum-dried at 80°C for 4 hours to obtain 6.45 g...

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Abstract

The invention relates to the synthesis of a large-grain diameter chiral stationary phase, wherein a synthetic method uses silica gel with the grain diameter of 40-60mum to prepare coating type and bonding type cellulosic derivative chiral stationary phases with the coating volume ratio of 18-25 percent and obtaines better chiral separation for propranolole hydrochloride enantiomers under a positive-phase condition. Because the filling aperture is large, gaps among fillings are large, reducing the resistance for a mobile phase, thereby effectively preventing the defects of high column pressure, easy blockage, shorter life and the like of a small-grain diameter chiral column and simultaneously effectively lowering the raw material expense of a silica gel matrix in the preparation of the chiral column.

Description

technical field [0001] The invention relates to the field of synthesis and application of cellulose-based chiral stationary phase, in particular to the synthesis and application of a large particle size chiral stationary phase. Background technique [0002] With the continuous deepening of enantiochemical research, people are increasingly aware of the important role of chiral compounds in medicine, pesticides and other biological functional materials. The chiral resolution of enantiomers is an effective means to obtain optically pure substances. Chiral chromatography, especially chiral high performance liquid chromatography (chiral HPLC), is a chiral resolution method that has developed rapidly in recent years. It can be used either It can be used for analysis and separation, and can also be used for preparation and separation. It has broad application prospects in the research fields of medicine, natural products and asymmetric synthesis, and has been paid more and more att...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/30B01J20/29B01J20/30B01J20/32C08B15/06C07C213/10
Inventor 王荣贾正平谢华杨沛马骏武晓玉
Owner 王荣
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