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Chiral polyamide film and preparation method and application thereof

A polyamide membrane and chiral technology, applied in the field of chiral separation, can solve the problems of high energy consumption, low efficiency, and large pollution of the resolution method, and achieve wide tolerance to pH, wide range of resolution objects, and simple preparation process Effect

Active Publication Date: 2019-03-19
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to solve the problems of high energy consumption, low efficiency and large pollution of the chiral drug resolution method, to provide a chiral polyamide membrane and its preparation method and its application in the chiral drug resolution. Diamine-β-cyclodextrin is used as a chiral resolution agent, cellulose acetate is used as a base membrane material, and trimesyl chloride is used as a linking agent. Separation solid membrane, the chiral separation solid membrane has excellent effect on the chiral separation of warfarin and tryptophan

Method used

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  • Chiral polyamide film and preparation method and application thereof
  • Chiral polyamide film and preparation method and application thereof
  • Chiral polyamide film and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] First prepare the ethylenediamine-β-cyclodextrin chiral polyamide membrane by the following steps, and then detect the concentration ratio and The concentration ratio of the two configurations in the stock solution was used to evaluate its resolution performance.

[0037] Synthesis of ethylenediamine-β-cyclodextrin:

[0038]The recrystallized β-cyclodextrin (100 g, 88 mmol) was weighed into a 1000 mL beaker containing 833 mL of purified water. NaOH (10.95g, 0.27mol) was dissolved in 33mL of water, and was added dropwise to the above suspension within 10min under magnetic stirring. After the addition was complete, the suspension became a uniform and slightly yellow solution. Weigh p-toluenesulfonyl chloride (p-TsCl, 16.82g, 0.09mol) and dissolve it in 50mL of acetonitrile, and add the solution dropwise to the above-mentioned light yellow reaction solution containing β-cyclodextrin. After 75min, all the drops are completely added, and there is A large amount of white pr...

Embodiment 2

[0053] A preparation method of ethylenediamine-beta-cyclodextrin, comprising the following steps:

[0054] (1) Weigh the recrystallized β-cyclodextrin (90g, 79mmol) and add it into a 1000mL beaker containing 800mL of pure water, dissolve NaOH (10g, 0.25mol) in 30mL of water, and under magnetic stirring conditions, Add it dropwise to the above suspension within 8 minutes;

[0055] (2) After the β-cyclodextrin suspension turns into a clear light yellow solution, weigh p-toluenesulfonyl chloride (p-TsCl, 16g, 0.086mol) and dissolve it in 45mL of acetonitrile, and add the solution dropwise to the above In the light yellow reaction solution of β-cyclodextrin, after 70 minutes, all the drops were completed, and a large amount of white precipitate was formed;

[0056] (3) The above reaction system was vigorously stirred at room temperature for 2h, and then 2mol·L -1 The hydrochloric acid was adjusted to nearly neutral, and placed in a refrigerator at 4°C overnight; the next day, su...

Embodiment 3

[0068] A preparation method of ethylenediamine-beta-cyclodextrin, comprising the following steps:

[0069] (1) Weigh recrystallized β-cyclodextrin (110g, 96.8mmol) and add it into a 1000mL beaker containing 850mL of purified water, dissolve NaOH (12g, 0.3mol) in 40mL of water, and under magnetic stirring conditions, Add it dropwise to the above suspension within 11 minutes;

[0070] (2) After the β-cyclodextrin suspension turns into a clear light yellow solution, weigh p-toluenesulfonyl chloride (p-TsCl, 18g, 0.096mol) and dissolve it in 50mL of acetonitrile, and add the solution dropwise to the above In the light yellow reaction solution of β-cyclodextrin, after 80 minutes, all the drops were completely added, and a large amount of white precipitate was formed;

[0071] (3) The above reaction system was vigorously stirred for 3 hours at room temperature, and then 2mol L -1 The hydrochloric acid was adjusted to nearly neutral, and placed in a refrigerator at 4°C overnight; t...

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Abstract

The invention discloses chiral polyamide film and a preparation method and application thereof. The chiral polyamide film as an interfacial polyamide cellulose acetate film with a chiral resolving capacity is prepared by: supporting the chiral resolving agent ethanediamine-beta-dextrin to the surface of acetate cellulose film, as a base film, through the bonding agent trimesoyl chloride, to be specific, performing two-step synthesis on beta-dextrin respectively with p-toluene sulfonyl chloride and anhydrous ethylenediamine to obtain ethanediamine modified-beta-dextrin, and performing interfacial polymerizing with the ethanediamine modified-beta-dextrin acting as a chiral resolving agent, trimesoyl chloride as a bonding agent and commercial acetate cellulose material, which has high mechanical strength, high compressive compaction resistance, good chemical stability and low price, as a base film material. The chiral polyamide film herein has low cost, is simple to prepare and is suitable for a wide range of resolving objects.

Description

technical field [0001] The invention belongs to the technical field of chiral resolution, and in particular relates to a chiral polyamide membrane, its preparation method and its application in the resolution of chiral drugs. Background technique [0002] Membrane separation method is to use the specific separation functional sites contained in the membrane or outside the membrane to resolve the vortex mixture. Membrane separation method has the advantages of low energy consumption, simple operation, large batch capacity, easy continuous operation, easy industrial scale-up, flexible device design and system application, and room temperature operation in most cases. [0003] According to the morphology of the membrane, the membrane separation method can be divided into two types: liquid membrane separation method and solid film separation method. However, chiral liquid membranes have a common disadvantage that is difficult to overcome, that is, poor stability, and their indu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/56C07D209/20C07B57/00B01D15/38
CPCB01D15/3833C07B57/00C07D209/20C07D311/56C07B2200/07
Inventor 季一兵柯健张莹陈建秋
Owner CHINA PHARM UNIV
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