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Preparation method of bonded chiral stationary phase

A chiral stationary phase, bonding type technology, applied in chemical instruments and methods, other chemical processes, etc., can solve the problems of low sample loading, low grafting rate, troublesome operation, etc., to facilitate large-scale production. , the reaction operation is simple, the effect of less side reactions

Inactive Publication Date: 2010-12-15
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, the polysaccharide derivative chiral stationary phase bonding method mainly uses conventional methods to synthesize chiral polymers with few types, molecular structure cannot be designed, molecular weight and molecular weight distribution are very wide, etc.; when bonded to the surface of silica particles, grafting The efficiency is low, the operation is troublesome, the distribution of the junction point of the chiral polymer is uneven and difficult to control, etc., which lead to the low sample loading of the stationary phase and affect the resolution efficiency.

Method used

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  • Preparation method of bonded chiral stationary phase
  • Preparation method of bonded chiral stationary phase
  • Preparation method of bonded chiral stationary phase

Examples

Experimental program
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Embodiment 1

[0037] Embodiment one: the synthesis of diacetone-D-galactose styrene (VBPG)

[0038] Drop 2.36g of p-chloromethylstyrene into a mixed aqueous solution (30mL) of 12g NaOH and 0.3g tetrabutylammonium bromide, and stir at room temperature for several minutes; dissolve 2.89g of diacetone-D-galactose (PG) In 30 mL of tetrahydrofuran, slowly drop the above mixed aqueous solution, stir at room temperature, and react for 24 h. After the reaction was completed, the reaction solution was washed with chloroform and distilled water until the solution was neutral, and the crude product was a yellow liquid in chloroform, and then purified with a chromatographic column (silica gel column, sherwood oil / ethyl acetate=8 / 1 (volume ratio)). The final product, VBPG, was a white snowflake solid with a yield of 46%.

Embodiment 2

[0039] Example two: α-butynyl bromoisobutyrate (BEiB)

[0040] At 0°C, 103g, 0.45mol bromoisobutyryl bromide in anhydrous ethyl acetate solution 200mL, was added dropwise to 150mL ethyl acetate solution containing 37.1g (0.53mol) n-butynol and 43g (0.53mol) pyridine , Stir the reaction for 2 h, and then react overnight at room temperature. After the reaction, wash with water, sodium bicarbonate hydrochloric acid solution and saturated brine twice respectively, dry and distill to obtain 70.0 g of butynyl α-bromoisobutyrate.

Embodiment 3

[0041] Example 3: Synthesis of functional P(VBPG) chiral chains using BEiB as an initiator

[0042] According to the ratio n(VBPG):n(BEiB):n(CuBr):n(PMDETA)=75:1:1:3. Add CuBr, PMDETA, BEiB, VBPG and toluene (5 mL) in sequence to a 10 mL ampoule, and seal the tube after argon gas for 10 minutes. The sealed ampoule was placed in an oil bath at a constant temperature (75° C.) for a predetermined time to react (6-18 days). After the reaction is over, take out the sealed tube, immediately cool it with cold water, open the sealed tube, precipitate in an appropriate amount of petroleum ether, and dry to obtain the chiral polymer.

[0043] Using bifunctional initiator (BEiB) and VBPG as monomers, the data of chiral polymer chains synthesized at different polymerization times are shown in Table 1. As can be seen from the data in the table, the chiral polymer molecular weight obtained by solution polymerization increases linearly with the polymerization time, and the molecular weight...

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Abstract

The invention belongs to the field of chiral stationary phases, and particularly relates to a preparation method of a polysaccharide chiral stationary phase which is suitable for a high-efficiency liquid phase chromatography and uses silicon dioxide as a carrier. The preparation method specifically comprises the following steps of: (1) synthesizing a chiral polymer chain, namely using para-diacetone-D-galactose styrene as a monomer, and performing atom transfer free radical polymerization reaction to synthesize the chiral polymer chain poly-diacetone-D-galactose styrene; (2) preparing the silicon dioxide carrier, namely synthesizing silicon dioxide granules by adopting a Stober method, performing chloromethylation by using a chloromethylation silane coupling agent to obtain chloromethylation silicon dioxide granules, and reacting the chloromethylation silicon dioxide granules with sodium azide to obtain silicon dioxide azide granules; and (3) forming a covalent bond connection for bonding by performing click chemical reaction on the chiral polymer chain prepared in the step (1) and the chloromethylation silicon dioxide granules obtained in the step (2) so as to obtain the bonded chiral stationary phase. The preparation method can be used for designing chiral polymer chains with different molecular weight and silicon dioxide granules with different grain size so as to obtain chiral stationary phases with different performance.

Description

technical field [0001] The invention belongs to the field of chiral stationary phases, in particular to a polysaccharide chiral stationary phase with silicon dioxide as a carrier suitable for high performance liquid chromatography (HPLC). Background technique [0002] The chiral stationary phase is obtained by reacting or coating optically active small molecules or chiral polymers on the surface of the silica gel carrier through chemical bonding. During resolution, the separation is achieved by the difference in the binding ability of the enantiomeric sample and the bonded or coated chiral molecule to form a diastereomeric complex. The separation efficiency and elution order depend on the relative strength. The main types of chiral stationary phases are protein bonded phases, polysaccharide bonded phases, chiral polymer bonded phases, cyclodextrin bonded phases, and macrocyclic antibodies. Among them, polysaccharides have a good and fine structure, and after modification, ...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30
Inventor 朱秀林程振平许文亮张丽芬周年琛张正彪
Owner SUZHOU UNIV
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