Limiting chiral chromatography stationary phase material and preparation method thereof

A chiral chromatography and stationary phase technology, which is used in the synthesis of new chromatographic separation materials to reduce losses, improve efficiency and accuracy

Inactive Publication Date: 2011-07-27
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, limited-access materials that can perform chiral separations have not yet been commercialized

Method used

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  • Limiting chiral chromatography stationary phase material and preparation method thereof
  • Limiting chiral chromatography stationary phase material and preparation method thereof
  • Limiting chiral chromatography stationary phase material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1. Synthesis of methyl butynyl methacrylate

[0024] Methylbutynol (21.0 mL, 217 mmol), triethylamine (29.8 mL, 207 mmol) were dissolved in dry dichloromethane (120 mL) and stirred, and the solution was placed in an ice-water bath and lowered to 0°C, Methacryloyl chloride (20.0 mL, 207 mmol) was added dropwise, and after reacting for 0.5 hours, the mixture was stirred at room temperature for 20 hours. The solution was washed twice with 1% HCl (weight percent concentration), saturated sodium bicarbonate solution and water respectively, the organic phase was dried with anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to obtain methyl butynyl methacrylate (MBMA for short) , the yield is 74%.

[0025] 2. Grafting ATRP initiator on the surface of silicon spheres

[0026] Pretreatment of matrix silica gel: porous silica gel microspheres (particle size 10 μm, pore size ) 6.0 g was added to the hydrochloric acid / water (1:1, V / V) solution, stirred ...

Embodiment 2

[0029] 1. Initiate ATRP on the surface of silica gel and graft poly(methyl butynyl methacrylate) (the product is abbreviated as pMBMA-sil)

[0030] Weigh 2.1 g of Br-sil prepared in Example 1 into a round-bottomed three-necked flask, add 0.83 ml (5.49 mmol) of methylbutynyl methacrylate and 30 ml of cyclohexanone, pass N 2 After 10 minutes, add 2,2'-bipyridine 0.0343 g (0.22 mmol) and CuBr 0.0158 g (0.11 mmol), N 2 The reaction was carried out at room temperature for 4 hours under protection. After the reaction is completed, the reaction solution is poured into ethanol to stop the polymerization reaction, and the copper ions adsorbed on the surface of the silicon spheres are washed away with a saturated aqueous solution of disodium EDTA, and then the unreacted substances are washed away with ethanol and acetone, and vacuum dried. , to obtain pMBMA-sil, and the number of repeating units n of grafted pMBMA was calculated to be 4.0 according to the increase in carbon content fro...

Embodiment 3

[0039] The chiral separation material (CD-sil) synthesized in Example 2 was loaded into a stainless steel chromatographic column of 150mm × 4.6mm i.d. by homogenization method, and the HPLC method was used to investigate the chiral drugs chlorthalidone and mandelic acid of this material. , chlorpheniramine and benzoin separation ability. The chromatographic conditions and separation results are shown in Table 1, and the chromatographic separation diagram is shown in Table 1. Figure 1-4 . The chiral selectivity alpha values ​​for the four drugs were >1.1.

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Abstract

The invention relates to a limiting chiral chromatography stationary phase material and a preparation method thereof. An atom transfer radical polymerization method and a click chemistry method are applied, a terpenes compound containing triazo is taken as a monomer, block polymerization is conducted on a silicon surface, a chiral separation layer with the inner layer bonded with cyclodextrin is prepared, and a limiting chiral separation material capable of removing protein is arranged on the outer layer. The limiting chiral chromatography stationary phase material has a multi-layer structure and mixing functions, can be used as a stationary phase, and is applied to the direct test on chromatograph of a sample containing protein, and simultaneously, the chiral separation can be conducted. By being taken as the new material for analysis of a chiral sample, the limiting chiral chromatography stationary phase material is applied to omitting the pretreatment of precipitated protein in the analysis of a biological sample, and the analyzing efficiency and accuracy are improved.

Description

technical field [0001] The invention belongs to the synthesis of novel chromatographic separation materials, in particular to an access-limited chiral chromatographic stationary phase material and a preparation method thereof. The multifunctional separation material prepared by atom transfer radical polymerization and click chemistry can be applied to the separation and analysis of chiral compounds in biological or environmental samples. Background technique [0002] Biological sample analysis is an important application area of ​​liquid chromatography. In the analysis of biological samples, the protein in the sample is easily denatured and adsorbed on the chromatographic column after contacting with the stationary phase, resulting in the rapid decline of the column performance and the blockage of the column, which has become a serious problem in the analysis of biological samples. In order to avoid the precipitation of protein on the chromatographic column, it is necessary...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30
Inventor 董襄朝王怀松
Owner NANKAI UNIV
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