Beta-cyclodextrin functionalized chiral stationary phase, preparation and application thereof

A technology of chiral stationary phase and cyclodextrin, which is applied in chemical instruments and methods, organic chemistry, organic chemistry methods, etc., can solve problems such as reducing the amount of cyclodextrin bonds, and achieve fewer steps, high reaction efficiency and high reaction efficiency. The effect of mild conditions

Active Publication Date: 2016-02-10
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, since the amount of alkynyl groups on the silica is fixed, the presence of multiple triazole linkages reduces the amount of cyclodextrin linkages

Method used

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  • Beta-cyclodextrin functionalized chiral stationary phase, preparation and application thereof
  • Beta-cyclodextrin functionalized chiral stationary phase, preparation and application thereof
  • Beta-cyclodextrin functionalized chiral stationary phase, preparation and application thereof

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Embodiment Construction

[0031] EXAMPLES Separation of enantiomers using a stationary phase of β-cyclodextrin functionalized silica microspheres.

[0032] Preparation of β-cyclodextrin functionalized silica microsphere stationary phase:

[0033] 1) Dissolve 3.00g of β-cyclodextrin into 50mL of anhydrous pyridine, then slowly add 8mL of dry tetrahydrofuran (containing 3.279mL of undecylenoyl chloride) dropwise, stir at 50°C for 36h, and then add 12mL of phenylisocyanate , the final reactant was stirred at 90°C for 10 h; pyridine and phenyl isocyanate were removed under reduced pressure, the residue was dissolved in ethanol, and then poured into a beaker filled with 200 mL of water, a large amount of solids precipitated ; After filtration, the filter cake was recrystallized with ethanol to obtain khaki mono / bis(undecenoyl)perphenylcarbamoyl β-cyclodextrin, MALDI-TOFMS (m / z): 3704 and 3751 respectively Based on the molecular weight of [mono(undecyl)perphenylcarbamoyl β-cyclodextrin+Na+] and [bis(undecyl...

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Abstract

The invention relates to a beta-cyclodextrin functionalized silica gel microsphere chiral stationary phase, preparation, and application thereof in enantiomer separation. The preparation method comprises the following steps: introducing 3-mercapto into the surface of silica gel microspheres at first, and then adding beta-cyclodextrin derivative functional monomers and an initiator, wherein the functional monomers carry out mercapto-alkene addition reactions under the regulation of the initiator so as to obtain the surface modified beta-cyclodextrin functional monomer chiral stationary phase. The preparation of chiral stationary phase is simple, the reaction conditions are mild, and the chiral stationary phase is successfully applied to the enantiomer separation.

Description

technical field [0001] The invention relates to the separation of enantiomers, in particular to a β-cyclodextrin functionalized silica microsphere stationary phase and its preparation, as well as its application in enantiomer separation. Background technique [0002] Separation of enantiomers by high performance liquid chromatography is an important and challenging task. The chiral stationary phase based on cyclodextrin is a widely used chiral stationary phase (CSP), because the hollow structure of cyclodextrin can form strong inclusion complexes with enantiomeric guest molecules, and the enantiomeric guest molecules and The difference in the strength of inclusion complexes formed by cyclodextrin cavities allows this cyclodextrin-functionalized stationary phase to be used for the separation of enantiomers. Much research has focused on developing new methods for bonding functionalized cyclodextrins to silica microspheres. The amino linking group is the first linking group i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30C07B57/00
Inventor 邹汉法黄光欧俊杰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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