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Silica gel bonded double-chirality active center chromatogram filler, preparation method and use thereof

A technology of active center and chromatographic packing, which is applied in the field of preparation of microcrystalline cellulose derivatives bichiral high performance liquid chromatography chiral chromatographic packing, which can solve the problem of derivatization reagents with few chiral centers and bonded chiral stationary phases. Few, no bonded dual-chiral chromatography packing reported, to achieve short separation time, high column efficiency, good permeability

Inactive Publication Date: 2009-04-29
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Okamoto's research group abroad is the most representative and contributing to the research on chiral CSP. We tracked its research progress in high performance liquid chromatography cell polysaccharide chiral stationary phase and found that the currently studied polysaccharide chiral Most of the stationary phases are coating type. Although there are bonded chiral stationary phases synthesized, there are few commercially available bonded chiral stationary phases, and there are few chiral centers in the derivatization reagents, only polysaccharides The class itself has a chiral center, and there are reports abroad that briefly introduce the coated bichiral chromatography packing, but there is no report on the bonded bichiral chromatography packing, and there is no report on the bichiral chromatography packing in China.

Method used

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  • Silica gel bonded double-chirality active center chromatogram filler, preparation method and use thereof
  • Silica gel bonded double-chirality active center chromatogram filler, preparation method and use thereof
  • Silica gel bonded double-chirality active center chromatogram filler, preparation method and use thereof

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Experimental program
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Effect test

Embodiment 1

[0040] (1) Silica gel activation: According to the volume mass ratio of hydrochloric acid to silica gel 2ml / g, prepare a mixture of 20% hydrochloric acid and silica gel with a pore size of 30nm in volume percentage, heat at 90°C for reflux for 6 hours, suction filter, and wash with deionized water to medium properties, baked at 105°C for 4 hours, and vacuum-dried at 50°C for 6 hours to obtain activated silica gel for use;

[0041] (2) Microcrystalline cellulose 6-hydroxyl protection: 1.6g microcrystalline cellulose, 7.0g triphenylchloromethane, then add 50ml of anhydrous pyridine to react in a 100ml three-necked flask, at 80 ° C, mechanically stirred, Pass N 2 Reflux for 24 hours under certain reaction conditions, after the reaction is completed, filter and wash with methanol to obtain 6-hydroxyl-protected microcrystalline cellulose;

[0042] (3) Carboxylic acid chlorination: 10mlDL-2-phenylpropionic acid and 6ml sulfur oxychloride at 50°C, mechanically stirred, and N 2 Refl...

Embodiment 2

[0046](1) Silica gel activation: According to the mass ratio of hydrochloric acid to silica gel volume mass ratio 3ml / g, prepare a mixture of 20% hydrochloric acid by volume percentage and 100nm pore size of silica gel, heat at 93°C for reflux for 6 hours, suction filter and wash with deionized water To neutrality, bake at 105°C for 4 hours, and vacuum-dry at 50°C for 6 hours to obtain activated silica gel for use;

[0047] (2) Microcrystalline cellulose 6-hydroxyl protection: microcrystalline cellulose 2.0g, triphenylchloromethane 8.0g, with 50ml anhydrous pyridine as solvent, at 90 ℃, mechanical stirring, logical N 2 Reflux for 24 hours under certain reaction conditions, after the reaction is completed, filter and wash with methanol to obtain 6-hydroxyl-protected microcrystalline cellulose;

[0048] (3) Carboxylic acid chlorination: 12mlDL-2-phenylpropionic acid and 7.5ml thionyl chloride were placed at 50°C, mechanically stirred, and N 2 Reflux under reaction conditions fo...

Embodiment 3

[0052] (1) Silica gel activation: According to the volume mass ratio of hydrochloric acid to silica gel 2-6ml / g, prepare a mixture of 20% hydrochloric acid by volume and silica gel with a pore size of 200nm, heat at 90-100°C and reflux for 6 hours, filter with deionization Wash with water until neutral, bake at 105°C for 4 hours, and vacuum-dry at 50°C for 6 hours to obtain activated silica gel for use;

[0053] (2) Protection of the 6-position hydroxyl group of microcrystalline cellulose: 3.0 g of microcrystalline cellulose, 10.5 g of triphenylchloromethane and 50 ml of anhydrous pyridine, at 90 ° C, mechanically stirred, and nitrogen 2 Reflux for 24 hours under certain reaction conditions, after the reaction is completed, use methanol suction filtration and washing to obtain 6-hydroxyl-protected microcrystalline cellulose;

[0054] (3) Carboxylic acid chlorination: 12mlDL-2-phenylpropionic acid and 7ml thionyl chloride at 50°C, mechanically stirred, and N 2 Reflux under rea...

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Abstract

The invention provides silica-bonded dual-chiral active central chromatography filler, a preparation method and applications thereof, belonging to the field of column filling. The preparation method comprises the following steps of: (1) activation of silica gel; (2) protection of microcrystalline cellulose 6-hydroxyl group; (3) carbonyl acyl chlorination; (4) derivative process of microcrystalline cellulose 2, 3-hydroxyl group and protection removal of 6-hydroxyl group; and (5) obtaining bonded chiral fixed phase by silica-bonded 2, 3-bonded 6-protection removal microcrystalline cellulose reaction and passivation of activated silica gel unreacted silanol group. The dual-chiral bonded chiral fixed phase is used for separating asymmetric synthesized chiral compounds, and n-hexane-isopropanol is used as flowing phase so as to separate the phenylethyl alcohol and ethanethioic acid, thus obtaining chromatograms. The filler, the preparation method and the application have high column efficiency, short separation time, and good separation effect on chiral compounds. The filling material generates no swelling even when in solvent, has good permeability performance and low column pressure; under the conditions of 100 percent n-hexane, flowing speed of 1ml / min and the chromatographic column of 150 multiplied by 4.6mm i.d, the column pressure is only 3.3MPa.

Description

technical field [0001] The invention relates to the preparation of chromatographic column fillers, in particular to the preparation of microcrystalline cellulose derivatives bichiral high-performance liquid chromatography chiral chromatographic fillers bonded on silica gel substrates. Background technique [0002] Separation column is the core of chromatographic technology, and the research of stationary phase is the basis for the establishment and development of various high performance liquid chromatography. In the face of the demand for high-purity substances in scientific research and production, it is crucial to develop more effective preparative separation technologies, new packing materials for preparative chromatography, and packing materials for separation of chiral compounds. Research and development of stationary phases with high separation efficiency, good selectivity, good activity recovery and quality recovery, and long life, which are compatible with chiral co...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30
Inventor 魏芸张芳
Owner BEIJING UNIV OF CHEM TECH
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