Method for preparing bonding type cyclodextrin stationary phase with click chemistry reaction

A technology of cyclodextrin and stationary phase, which is applied in the field of chromatographic stationary phase, can solve the problems of harsh reaction conditions, difficult operation, complex preparation process of bonded cyclodextrin stationary phase, etc., achieves simple preparation method, avoids side reactions, Effect of High Column Efficiency and Separation Selectivity

Active Publication Date: 2008-10-01
浙江华谱新创科技有限公司
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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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  • Method for preparing bonding type cyclodextrin stationary phase with click chemistry reaction
  • Method for preparing bonding type cyclodextrin stationary phase with click chemistry reaction
  • Method for preparing bonding type cyclodextrin stationary phase with click chemistry reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] 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.

[0050] 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.

[0051] Take 2.5g of d...

Embodiment 2

[0054] 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.

[0055] 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.

[0056] 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

[0059] 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:

[0060]

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Abstract

The invention relates to a preparation of cyclodextrin bonded stationary phase, in particular to a method which prepares bonding-typed cyclodextrin stationary phase by adopting click chemistry reaction; the preparation method comprises two steps: an azid group or alkyne group is led in the surface of silica gel by a silane coupling agent to prepare azide group silica gel derivatives or alkyne group silica gel derivatives; a 1, 3-ring addition reaction of the azid group and the alkyne group which is also the click chemistry is then carried out for 24-72 hours under the temperature of 20-80 DEG C; the cyclodextrin where the alkyne group or azid group is decorated is bonded onto the surface of the silica gel. The bonding reaction provided by the invention has high selectivity, can excellently keeps the structure of the cyclodextrin, and has simple preparation method and wide applicable range; the prepared cyclodextrin bonded stationary phase has high surface bonding quantity, which is suitable for being used for high-effect liquid phase chromatography separation material and is especially applicable for separating strong polar compounds under the mode of hydrophilic liquid phase chromatography.

Description

technical field [0001] The invention relates to a chromatographic stationary phase, in particular to a method for preparing a bonded cyclodextrin stationary phase by adopting a click chemistry reaction. 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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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/286
CPCB01D15/305
Inventor 梁鑫淼郭志谋雷爱文张永平丰加涛徐青
Owner 浙江华谱新创科技有限公司
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