Beta-cyclodextrin grafted polymer chiral separation membrane and preparation method thereof

A high molecular polymer, chiral separation technology, applied in the direction of semi-permeable membrane separation, chemical instruments and methods, membrane technology, etc., can solve the problems affecting the membrane flux, limiting the immobilization capacity of chiral substances, etc.

Inactive Publication Date: 2015-08-12
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned patent reports all immobilize β-cyclodextrin on the surface of the membrane. On the one hand, it limits the amount of immobilized chiral substances, and on the other hand, it also affects the flux of the membrane.

Method used

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  • Beta-cyclodextrin grafted polymer chiral separation membrane and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] (1) Weigh 10g of β-cyclodextrin and dissolve it in 100mL of 0.8mol / L NaOH solution, add 4g of p-toluenesulfonyl chloride at a controlled temperature of 5°C, stir vigorously, react for 10h, and filter with 1mol / L hydrochloric acid neutralized to neutral, put it in the refrigerator for crystallization at 10°C for 12 hours, filter, and the filter cake is p-toluenesulfonyl-β-cyclodextrin intermediate;

[0027] (2) Weigh 6g p-toluenesulfonyl-β-cyclodextrin intermediate and 4g triethylamine, dissolve in 50mL dimethyl sulfoxide, stir magnetically and heat up to 120°C for 10h, pour the reacted solution Precipitate in ethanol, filter with suction, and vacuum-dry the filter cake to obtain aldylated β-cyclodextrin;

[0028] (3) Dissolve 1g of aldylated β-cyclodextrin and 3g of polyvinyl alcohol in 100mL of dimethyl sulfoxide, react at 60°C for 10h, pour the material into excess ethanol to precipitate after the reaction, and filter , after drying, β-cyclodextrin grafted polyvinyl...

Embodiment 2

[0031] (1) Weigh 10g of β-cyclodextrin and dissolve it in 100mL of 1mol / L NaOH solution, add 6g of p-toluenesulfonyl chloride at a controlled temperature of 8°C, stir vigorously, react for 18h, and filter with 0.2mol / L hydrochloric acid neutralized to neutral, put it in the refrigerator for crystallization at 4°C for 24 hours, filter, and the filter cake is p-toluenesulfonyl-β-cyclodextrin intermediate;

[0032] (2) Weigh 10g of p-toluenesulfonyl-β-cyclodextrin intermediate and 15g of triethylamine, dissolve in 80mL of dimethyl sulfoxide, stir magnetically and raise the temperature to 150°C for 6 hours, pour the reacted solution Precipitate in acetone, filter with suction, and vacuum-dry the filter cake to obtain aldylated β-cyclodextrin;

[0033] (3) Dissolve 6g of aldylated β-cyclodextrin and 6g of chitosan in 150mL of 10% acetic acid aqueous solution, react at 70°C for 24h, evaporate the solvent after the reaction, and obtain β-cyclodextrin after drying. Cyclodextrin graf...

Embodiment 3

[0036] (1) Weigh 10g of β-cyclodextrin and dissolve it in 100mL of 1mol / L NaOH solution, add 6g of p-toluenesulfonyl chloride at a controlled temperature of 8°C, stir vigorously, react for 18h, and filter with 0.2mol / L hydrochloric acid neutralized to neutral, put it in the refrigerator for crystallization at 4°C for 24 hours, filter, and the filter cake is p-toluenesulfonyl-β-cyclodextrin intermediate;

[0037] (2) Weigh 10g of p-toluenesulfonyl-β-cyclodextrin intermediate and 15g of triethylamine, dissolve them in 80mL of dimethyl sulfoxide, stir them magnetically and raise the temperature to 150°C for 6 hours, pour the reacted solution Precipitate in acetone, filter with suction, and vacuum-dry the filter cake to obtain aldylated β-cyclodextrin;

[0038] (3) Dissolve 6g of aldylated β-cyclodextrin and 6g of cellulose in 100mL of 50% acetic acid aqueous solution, react at 70°C for 24h, evaporate the solvent after the reaction, and obtain β-cyclodextrin after drying. Dextri...

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Abstract

The invention belongs to the technical filed of polymer membrane separation and discloses a beta-cyclodextrin grafted polymer chiral separation membrane and a preparation method thereof. The method comprises the following steps: (1) with beta-cyclodextrin as the raw materials, preparing aldehyde cyclodextrin by reacting the beta-cyclodextrin with toluene sulfochloride and triethylamine in sequence; (2) performing aldolization with the aldehyde cyclodextrin and a polymer containing hydroxyl or Schiff base reaction with the aldehyde cyclodextrin and a polymer containing amidogen, so as to obtain a beta-cyclodextrin grafted polymer; and (3) dissolving the beta-cyclodextrin grafted polymer in a solvent to prepare a casting membrane liquid and preparing the beta-cyclodextrin grafted polymer chiral separation membrane by adopting a phase conversion method. The prepared beta-cyclodextrin grafted polymer chiral separation membrane can be applied for separating raceme, so as to realize green and efficient separation of chiral medicines.

Description

technical field [0001] The invention belongs to the technical field of polymer membrane chiral separation, and in particular relates to a β-cyclodextrin grafted polymer chiral separation membrane and a preparation method thereof. Background technique [0002] Chiral drugs refer to the introduction of a chiral center into the molecular structure of a drug, resulting in a pair of enantiomers that are mirror images of each other. Due to the different pharmacokinetic processes of the two enantiomers in chiral drugs, the There are often significant differences between the two enantiomers in terms of pharmacological activity, metabolic process, metabolic rate and toxicity in vivo. Under normal circumstances, only one enantiomer has pharmacological effects, while the other enantiomer not only has no pharmacological effects, but also produces certain side effects. After the U.S. Food and Drug Safety Administration promulgated regulations on chiral drugs, relevant certification agen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01D71/78B01D67/00
Inventor 严峰李俊平曲玉宁王明霞王真姬宇
Owner TIANJIN POLYTECHNIC UNIV
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