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Chitosan carbanilate-carbamido derivative preparation method

A technology of phenyl carbamate and phenyl isocyanate, which is applied in the field of synthesis of chitosan derivatives, can solve problems such as poor solubility, and achieve the effects of improving solubility, good chiral recognition ability, and good industrialization prospects

Active Publication Date: 2014-12-31
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solubility of such chitosan derivatives in tetrahydrofuran is very poor, so DMSO was used as a coating solvent in the preparation of chiral stationary phases

Method used

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  • Chitosan carbanilate-carbamido derivative preparation method
  • Chitosan carbanilate-carbamido derivative preparation method
  • Chitosan carbanilate-carbamido derivative preparation method

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preparation example Construction

[0052] Specifically, the preparation method of the present invention may comprise the following steps:

[0053] (1) add reaction solvent in chitosan raw material and carry out swelling,

[0054] (2) adding the phenyl isocyanate or phenyl isocyanate with side chains, reacting at a reaction temperature of 40-150°C, and a reaction time of 0.5-24 hours, and

[0055] (3) The reaction product is dropped into the isolation solvent to form chitosan derivatives to precipitate out.

[0056] For example, the preparation method of the present invention can be carried out as follows: under vacuum high temperature, stir the chitosan raw material of complete deacetylation for 4-6 hours, add anhydrous dimethyl sulfoxide to swell chitosan under the protection of inert gas 24- For 48 hours, add anhydrous lithium chloride at room temperature for 4-12 hours, and add phenylisocyanate with different side chains to react for 1-24 hours under high-temperature inactive gas. Afterwards, the chitosan ...

Embodiment 1

[0067] The synthetic steps of chitosan 4-methoxyphenyl carbamate-ureido derivative (a):

[0068] 1) At 80°C, 0.20g of chitosan (molecular weight: 50,000-300,000) is completely deacetylated, stirred and vacuum-dried for 4 hours.

[0069] 2) Under nitrogen protection, add 8 mL of anhydrous dimethyl sulfoxide (DMSO), and swell for 48 h.

[0070] 3) At 80°C, under nitrogen protection, add 1.60 mL of 4-methoxyphenyl isocyanate (the molar mass is 3.0 times that of hydroxyl and amino groups), and react for 24 hours.

[0071] 4) Add the above solution dropwise into 160 mL of methanol solvent with a dropper, and precipitate chitosan derivatives.

[0072] 5) Vacuum drying at 60° C. for 48 hours to obtain chitosan 4-methoxyphenylcarbamate-ureido derivatives with a yield of 63.16%.

Embodiment 2

[0074] The synthetic steps of chitosan 4-ethylphenyl carbamate-ureido derivative (b):

[0075] 1) At 80°C, 0.20g of chitosan (molecular weight: 50,000-300,000) is completely deacetylated, stirred and vacuum-dried for 4 hours.

[0076] 2) Under nitrogen protection, add 8 mL of anhydrous dimethyl sulfoxide (DMSO), and swell for 48 hours.

[0077] 3) At room temperature, add 0.40g of lithium chloride and stir for 12h.

[0078] 4) At 80°C, under nitrogen protection, add 1.06 mL of 4-ethylphenyl isocyanate (the molar mass is 2.0 times that of the hydroxyl and amino groups), and react for 1 h.

[0079] 5) Add the above solution dropwise into 160mL of methanol solvent with a dropper, and precipitate the chitosan derivative precipitate.

[0080] 6) Vacuum drying at 60°C for 48 hours, the yield of chitosan was 73.20% chitosan-4-ethylphenylcarbamate-ureido derivatives.

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Abstract

The invention provides a novel chitosan carbanilate-carbamido derivative synthetic method, the method employs chitosan and phenyl isocyanate with different groups to react, and then the hydroxy and amino on chitosan can be completely conversed to the chitosan carbanilate-carbamido derivative of carbamate and carbamido. According to the invention, a coating process is employed to prepare the derivative to a chiral stationary phase, and high performance liquid chromatography is used for resolution of various enantiomers, and the chiral stationary phase has high chiral identification capability.

Description

technical field [0001] The invention relates to a novel synthesis method of chitosan derivatives, in particular to a chitosan derivative with smaller structure and better chiral recognition ability which can be used as chiral stationary phase of high performance liquid chromatography. method of synthesis. Background technique [0002] The chiral separation of enantiomers by high performance liquid chromatography has become one of the most effective methods for the separation of enantiomers. The preparation of chiral stationary phase with high chiral recognition ability is the key content of this separation technology. So far, more than 200 chiral stationary phases have been commercialized. Among them, derivatives of polysaccharides (mainly cellulose and starch) are one of the most efficient and widely used chiral stationary phases. [0003] Chitosan is the product of deacetylation of chitin. Because it is non-toxic, harmless, environmentally friendly, and has good biocomp...

Claims

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Application Information

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IPC IPC(8): C08B37/08B01J20/24
Inventor 张丽丽左文丽沈军冈本佳男
Owner DAICEL CHEM IND LTD
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