Fullerene cellulose derivative used as chiral stationary phase material and preparation method thereof

A cellulose derivative, chiral stationary phase technology, applied in chemical instruments and methods, other chemical processes, etc., can solve the problems of limited types of chiral compounds to be separated, shortened service life of chiral stationary phase materials, etc.

Inactive Publication Date: 2017-04-05
CHANGCHUN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when the existing cellulose derivatives are used as chiral stationary phase materials for the separation of chiral compounds, it is required that the solvent used in the organic solution of the chiral compound to be separated should be a non-polar solvent, which leads to the limited, and this also results in a shorter lifetime of the chiral stationary phase material, e.g. typically only 5000 hours

Method used

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  • Fullerene cellulose derivative used as chiral stationary phase material and preparation method thereof
  • Fullerene cellulose derivative used as chiral stationary phase material and preparation method thereof
  • Fullerene cellulose derivative used as chiral stationary phase material and preparation method thereof

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Embodiment Construction

[0025] The whole process of the preparation method of the fullerene cellulose derivative used as the chiral stationary phase material of the present invention is as follows:

[0026]

[0027] The preparation process of the fullerene cellulose derivatives of the present invention will now be described in detail with examples.

[0028] 1. Preparation of cellulose-6-triphenylmethyl ether

[0029] Take 2 g of microcrystalline cellulose in a 250 mL two-necked bottle, and dry it in vacuum at 80° C. for 4 hours. Fill with dry high-purity nitrogen, add 60 mL of purified N,N-dimethylacetamide under nitrogen protection, and stir at 80°C for 12 hours. Cool to room temperature, add 4g of anhydrous lithium chloride as a catalyst, stir vigorously until the solution turns from cloudy to clear, then add 28mL of pyridine and 10.8g of triphenylchloromethane in sequence. Raise the temperature to 80°C and react for 24 hours. After the reaction, the orange-yellow product solution was added d...

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Abstract

The invention relates to a fullerene cellulose derivative used as a chiral stationary phase material and a preparation method of the fullerene cellulose derivative and belongs to the technical field of organic polymer materials. A nonpolar solvent is required by using an existing cellulose derivative as the chiral stationary phase material. The preparation method provided by the invention is characterized by comprising the following steps: bonding a triphenylchloromethane protective group to 6-hydroxyl of cellulose; derivatizing 2, 3-hydroxyls of cellulose by virtue of one of 3, 5-dimethyl phenyl isocyanate, 3, 5-dichlorophenyl isocyanate and phenyl isocyanate; removing the triphenylchloromethane protective group by using hydrochloric acid; replacing the 6-hydroxyl of cellulose by using 6-bromohexanoic acid through esterification reaction; carrying out nucleophilic substitution on sodium azide and 6-bromine; and carrying out addition reaction on fullerene and azido to obtain the fullerene cellulose derivative used as the chiral stationary phase material. The structural formula of the derivative is shown in the description.

Description

technical field [0001] The invention relates to a fullerene cellulose derivative used as a chiral stationary phase material and a preparation method thereof. The chiral stationary phase material is used in high performance liquid chromatography and can separate two pairs of chiral compounds. Enantiomers, for example, the separation of enantiomers with medicinal effects and optically active opposite enantiomers with toxic side effects in chiral drugs belongs to the technical field of organic polymer materials. Background technique [0002] The physical and chemical properties of the two enantiomers of chiral compounds, such as melting point, boiling point, solubility, refractive index, etc., are exactly the same, but the optical activity is opposite. Metabolic reactions in living organisms are carried out in a chiral environment. Since the optical activity of the two enantiomers of chiral compounds is opposite, their reactions in living organisms are therefore very different....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B15/06B01J20/26B01J20/30B01J20/29
Inventor 沈贤德高波李岳沈相俊
Owner CHANGCHUN UNIV OF SCI & TECH
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