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Preparation method of cyclodextrin bonded stationary phase

A technology of cyclodextrin and stationary phase, which is applied in the field of chromatographic stationary phase, can solve the problems of complex preparation process, difficult operation and harsh reaction conditions of bonded cyclodextrin stationary phase, achieve high column efficiency and separation selectivity, and avoid side effects The effect of simple reaction and preparation method

Inactive Publication Date: 2010-06-23
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation process of these selective bonded cyclodextrin stationary phases is relatively complicated, the reaction conditions are relatively harsh, and the operation is difficult.
There is no report on the preparation of cyclodextrin bonded stationary phase using "click chemistry"

Method used

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  • Preparation method of cyclodextrin bonded stationary phase
  • Preparation method of cyclodextrin bonded stationary phase
  • Preparation method of cyclodextrin bonded stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] In a 1000ml three-necked flask, add 500ml of anhydrous DMF, 45mmol (about 10ml) of 3-chloropropyltriethoxysilane, 60mmol (about 4.0g) of sodium azide, and then add 3.0mmol of sodium iodide (about 0.5g) As a catalyst, react at 80°C for 24h, then add 20g of spherical silica gel particles with a particle size of 5μm, react at 80°C for another 24h, and then wash with dichloromethane, ethanol, water, and acetone twice, each time 200ml, 60 °C and vacuum-dried for 12 hours to obtain (3-propyl)azido silica gel.

[0047] In a 50ml three-neck flask under the protection of nitrogen, 15ml of propargylamine was added, and then 6g of mono-6-p-toluenesulfonyl-β-cyclodextrin was added, and heated to reflux for 12 hours. After cooling to room temperature under nitrogen protection, the reaction system was poured into acetonitrile to precipitate a solid. The solid was recrystallized from methanol to obtain the product mono-6-deoxy-N-propargylamino-β-cyclodextrin.

[0048] Take 2.5g of d...

Embodiment 2

[0051] Add 500ml of anhydrous toluene, 120mmol (about 30ml) of 3-isocyanatotriethoxysilane, 160mmol of propargyl amine (about 9g) into a 1000ml three-necked flask, react at 80°C for 12h, and then add Spherical silica gel particles 40g were reacted at 80°C for 48h, then washed twice with dichloromethane, ethanol, water, and acetone, 200ml each time, and vacuum-dried at 60°C for 12 hours to obtain alkynyl silica gel derivatives.

[0052] A 50ml three-neck flask was under nitrogen protection, 15ml of DMF was added, and then 10g of mono-6-p-toluenesulfonyl-β-cyclodextrin was added, and heated to 65°C for 24 hours. The solvent DMF was concentrated to 5ml, poured into acetone to precipitate a solid. The solid is recrystallized with water to obtain the product mono-6-deoxy-β-azidocyclodextrin.

[0053] Take 2.5g of dried alkynyl silica gel derivatives, add 60ml of water, 60ml of ethanol, 4g of mono-6-deoxy-azido-cyclodextrin into the reactor, then add 0.05g of copper sulfate and 0.1...

Embodiment 3

[0055] The difference from Example 1 is that mono-6-p-toluenesulfonyl-α-cyclodextrin is used instead of mono-6-p-toluenesulfonyl-β-cyclodextrin, according to the synthesis of Example 1 Steps can get another cyclodextrin bonded stationary phase, the structure of which is:

[0056]

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Abstract

The invention relates to preparation of cyclodextrin bonded stationary phase, in particular to a method for preparing cyclodextrin bonded stationary phase by taking click chemistry as bonding reaction process. The preparation method comprises two steps: firstly introducing triazo- or alkynyl onto the surface of silica gel by silane coupling agent to prepare triazo-silica gel derivative or alkynyl silica gel derivative, then carrying out 1,3-cycloaddition reaction on triazo- and alkynyl, namely, click chemistry, in aqueous solution at 20-80 DEG C for 24-72 hours, and binding cyclodextrin decorated with alkynyl or triazo- onto the surface of silica gel. The bonding reaction provided in the invention has high selectivity, can maintain cyclodextrin structure well, so that the preparation method is simple and broad in application range, the surface binding amount of the prepared cyclodextrin bonded stationary phase is high, is suitable to be as high performance liquid chromatography separation material, and especially suitable for separating strongly polar compound in hydrophilic liquid chromatography mode.

Description

technical field [0001] The invention relates to a chromatographic stationary phase, specifically adopting click chemistry as a bonding reaction method to prepare a cyclodextrin bonded stationary phase. technical background [0002] Cyclodextrins are a type of cyclic oligosaccharides linked by glucose units through 1,4-α glycosidic bonds. They have a special cavity structure and can interact with many molecules in a "supramolecular" manner to form an "inclusive complex". Substances", known as the "second-generation host molecule" after the crown ether. With the rapid development of chromatographic separation technology, cyclodextrin has been widely used in the field of chromatographic separation (including capillary electrophoresis and electrochromatography) [Song Li and William C. Purdy, Chem. Rev. 1992, 92, 1457-1470]. Cyclodextrin or its derivatives are immobilized on the surface of silica gel and other substrates by chemical bonding as a liquid chromatography separation ...

Claims

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Application Information

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IPC IPC(8): B01J20/286
CPCB01D15/305
Inventor 梁鑫淼赵艳艳郭志谋
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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