A zwitterionic hydrophilic chromatographic stationary phase and preparation method thereof

Abstract

The invention is a zwitterionic hydrophilic chromatographic stationary phase, the terminal of the bonded phase is a zwitterionic group modified by a dibasic acid anhydride to modify the polyamine, which first undergoes a silanization reaction (single-point / multi-point bonding or horizontal polymerization) Polyamino groups are bonded to the surface of silica gel to obtain polyamino silica gel, and then the polyamino silica gel is used as a carrier to prepare zwitterionic hydrophilic chromatographic stationary phase by amidation reaction of acid anhydride and amino group. Due to the wide range of polyamine compounds and acid anhydrides used, adjustable properties, and the simple and efficient amidation reaction between acid anhydrides and polyamines, the stationary phase provided by the invention can accurately and flexibly control the charge / potential and hydrophilicity of the filler surface , is very suitable as a new type of stationary phase for hydrophilic interaction chromatography, and can be widely used in the separation of various samples.

Description

technical field

[0001] The invention relates to a zwitterionic hydrophilic chromatographic stationary phase and a preparation method thereof, in particular to a novel hydrophilic interaction chromatographic stationary phase whose bonded phase terminal is a zwitterionic group.

[0002] technical background

[0003] Hydrophilic Interaction Liquid Chromatography (HILIC) is a new chromatographic separation technique developed in recent years for the separation of highly polar compounds, which was first proposed by Alpert in 1990 [Alpert, A.J.J. ]. Similar to normal phase chromatography (NPLC), HILIC uses a polar stationary phase and a relatively less polar water / organic solvent as the mobile phase, where water is the strong elution solvent. HILIC can use a solution system with a large water content as the mobile phase, which can solve the problems of poor solubility of water-soluble substances in the mobile phase of normal phase chromatography, retention time is very sensitive t...

Examples

Embodiment 1

[0040] Weigh 10g spherical silica gel (particle size is 5μm, pore size is 10nm, specific surface area is 305m 2 / g), placed in a 250mL glass flask, added 150mL of 10% hydrochloric acid solution by volume, heated to reflux for 12 hours, cooled to room temperature, filtered, washed with water until neutral, and dried at 150°C for 24 hours. Put the dried silica gel in a three-necked flask, and add 80 mL of dry toluene to the silica gel under the condition of nitrogen gas, stir well, and then add N-(β-aminoethyl-γ-aminopropyl)methyl Dimethoxysilane 1mL, stirred reaction at 110°C and refluxed for 3 hours, filtered under reduced pressure and washed with toluene, dichloromethane, water, tetrahydrofuran, methanol in sequence, and dried at 60°C to constant weight to obtain polyaminosilica gel . Weigh 10g of polyamino silica gel, add 50mL of N,N-dimethylformamide, 1g of succinic anhydride, 0.1g of 4-dimethylaminopyridine and 0.1g of pyridine, stir at room temperature for 3h, after the ...

Embodiment 2

[0042] Weigh 10g spherical silica gel (particle size is 5μm, pore size is 10nm, specific surface area is 305m 2 / g), placed in a 250mL glass flask, added 200mL of 20% hydrochloric acid solution, heated to reflux for 24 hours, cooled to room temperature, filtered, washed with water until neutral, and dried at 80°C for 24 hours. Put the dried silica gel in a three-necked flask, add 200mL of dry toluene to the silica gel under the condition of blowing nitrogen, stir evenly, and then add N-(β-aminoethyl-γ-aminopropyl)methyl Dimethoxysilane 50mL, stirred reaction at 120°C and refluxed for 24 hours, filtered under reduced pressure and washed with toluene, dichloromethane, water, tetrahydrofuran, methanol in sequence, and dried at 80°C to constant weight to obtain polyaminosilica gel . Weigh 10g polyamino silica gel, add 200mL N,N-dimethylformamide, 100g succinic anhydride, 10g 4-dimethylaminopyridine and 10mL pyridine, stir at room temperature for 3h, after reaction, filter under r...

Embodiment 3

[0044] Weigh 10g spherical silica gel (particle size is 5μm, pore size is 10nm, specific surface area is 305m 2 / g), placed in a 250mL glass flask, added 150mL of 10% hydrochloric acid solution by volume, heated to reflux for 12 hours, cooled to room temperature, filtered, washed with water until neutral, and dried at 150°C for 24 hours. Put the dried silica gel in a three-necked flask, and add 80 mL of dry toluene to the silica gel under the condition of nitrogen gas, stir evenly, and then add N-(β-aminoethyl-γ-aminopropyl) trimethoxy Silane 3mL, stirred at 110°C for reflux for 6 hours, filtered under reduced pressure and washed with toluene, dichloromethane, water, tetrahydrofuran, methanol, and dried at 60°C to constant weight to obtain polyaminosilica gel. Weigh 10g polyamino silica gel, add 60mL N,N-dimethylformamide, 8g succinic anhydride, 0.8g 4-dimethylaminopyridine and 2mL pyridine, stir and react at room temperature for 24h, vacuum filter after reaction and use Wash...

technical field

[0001] The invention relates to a zwitterionic hydrophilic chromatographic stationary phase and a preparation method thereof, in particular to a novel hydrophilic interaction chromatographic stationary phase whose bonded phase terminal is a zwitterionic group.

[0002] technical background

[0003] Hydrophilic Interaction Liquid Chromatography (HILIC) is a new chromatographic separation technique developed in recent years for the separation of highly polar compounds, which was first proposed by Alpert in 1990 [Alpert, A.J.J. ]. Similar to normal phase chromatography (NPLC), HILIC uses a polar stationary phase and a relatively less polar water / organic solvent as the mobile phase, where water is the strong elution solvent. HILIC can use a solution system with a large water content as the mobile phase, which can solve the problems of poor solubility of water-soluble substances in the mobile phase of normal phase chromatography, retention time is very sensitive t...

Examples

Embodiment 1

[0040] Weigh 10g spherical silica gel (particle size is 5μm, pore size is 10nm, specific surface area is 305m 2 / g), placed in a 250mL glass flask, added 150mL of 10% hydrochloric acid solution by volume, heated to reflux for 12 hours, cooled to room temperature, filtered, washed with water until neutral, and dried at 150°C for 24 hours. Put the dried silica gel in a three-necked flask, and add 80 mL of dry toluene to the silica gel under the condition of nitrogen gas, stir well, and then add N-(β-aminoethyl-γ-aminopropyl)methyl Dimethoxysilane 1mL, stirred reaction at 110°C and refluxed for 3 hours, filtered under reduced pressure and washed with toluene, dichloromethane, water, tetrahydrofuran, methanol in sequence, and dried at 60°C to constant weight to obtain polyaminosilica gel . Weigh 10g of polyamino silica gel, add 50mL of N,N-dimethylformamide, 1g of succinic anhydride, 0.1g of 4-dimethylaminopyridine and 0.1g of pyridine, stir at room temperature for 3h, after the ...

Embodiment 2

[0042] Weigh 10g spherical silica gel (particle size is 5μm, pore size is 10nm, specific surface area is 305m 2 / g), placed in a 250mL glass flask, added 200mL of 20% hydrochloric acid solution, heated to reflux for 24 hours, cooled to room temperature, filtered, washed with water until neutral, and dried at 80°C for 24 hours. Put the dried silica gel in a three-necked flask, add 200mL of dry toluene to the silica gel under the condition of blowing nitrogen, stir evenly, and then add N-(β-aminoethyl-γ-aminopropyl)methyl Dimethoxysilane 50mL, stirred reaction at 120°C and refluxed for 24 hours, filtered under reduced pressure and washed with toluene, dichloromethane, water, tetrahydrofuran, methanol in sequence, and dried at 80°C to constant weight to obtain polyaminosilica gel . Weigh 10g polyamino silica gel, add 200mL N,N-dimethylformamide, 100g succinic anhydride, 10g 4-dimethylaminopyridine and 10mL pyridine, stir at room temperature for 3h, after reaction, filter under r...

Embodiment 3

[0044] Weigh 10g spherical silica gel (particle size is 5μm, pore size is 10nm, specific surface area is 305m 2 / g), placed in a 250mL glass flask, added 150mL of 10% hydrochloric acid solution by volume, heated to reflux for 12 hours, cooled to room temperature, filtered, washed with water until neutral, and dried at 150°C for 24 hours. Put the dried silica gel in a three-necked flask, and add 80 mL of dry toluene to the silica gel under the condition of nitrogen gas, stir evenly, and then add N-(β-aminoethyl-γ-aminopropyl) trimethoxy Silane 3mL, stirred at 110°C for reflux for 6 hours, filtered under reduced pressure and washed with toluene, dichloromethane, water, tetrahydrofuran, methanol, and dried at 60°C to constant weight to obtain polyaminosilica gel. Weigh 10g polyamino silica gel, add 60mL N,N-dimethylformamide, 8g succinic anhydride, 0.8g 4-dimethylaminopyridine and 2mL pyridine, stir and react at room temperature for 24h, vacuum filter after reaction and use Wash...

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