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A kind of chiral polyamide membrane and its preparation method and application

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

Active Publication Date: 2022-07-22
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

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  • A kind of chiral polyamide membrane and its preparation method and application
  • A kind of chiral polyamide membrane and its preparation method and application
  • A kind of chiral polyamide membrane and its preparation method and application

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Embodiment 1

[0036] First, an ethylenediamine-β-cyclodextrin chiral polyamide membrane was prepared by the following steps, and then the concentration ratio of the two configurations in the filtrate filtered by the chiral membrane and the The concentration ratio of the two configurations in the stock solution was used to evaluate the 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 added dropwise to the above suspension within 10min under magnetic stirring conditions. After the dropwise addition was completed, the suspension became a uniform and slightly yellow solution. Weigh p-toluenesulfonyl chloride (p-TsCl, 16.82 g, 0.09 mol) and dissolve it in 50 mL of acetonitrile, and add the solution dropwise to the light yellow reaction solution containing β-cyclodextrin. A large ...

Embodiment 2

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

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

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

[0056] (3) The above reaction system was vigorously stirred at room temperature for 2h, and then used 2mol·L -1 The hydrochloric acid was adjusted to near neutral, and plac...

Embodiment 3

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

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

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

[0071] (3) The above reaction system was vigorously stirred at room temperature for 3h, and then used 2mol·L -1 The hydrochloric acid was adjusted to near neutral, and placed in a refrigerator at 4°C overnigh...

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Abstract

The invention discloses a chiral polyamide membrane and its preparation method and application in the separation of chiral drugs. The chiral polyamide membrane is based on a cellulose acetate membrane, and a chiral resolving agent ethylenediamine-β-cyclodextrin is immobilized on the surface of the chiral polyamide membrane through a linking agent trimesyl chloride. The specific preparation method is that β-cyclodextrin is separately prepared with p-toluenesulfonyl chloride and anhydrous ethylenediamine by a two-step synthesis method to obtain ethylenediamine-modified-β-cyclodextrin, which is used as a chiral selector to mechanically The commercial cellulose acetate material with high strength, strong compression resistance, good chemical stability and low price is used as the base film material, and trimesyl chloride is selected as the linking agent. Interfacial Polyamide Cellulose Acetate Membrane for Splitting Capability. The chiral polyamide membrane of the invention has the advantages of low cost, simple preparation process and wide separation objects.

Description

technical field [0001] The invention belongs to the technical field of chiral separation, and in particular relates to a chiral polyamide membrane and a preparation method thereof and application in the separation of chiral drugs. Background technique [0002] Membrane technology separation method is to use the specific separation function sites contained in the membrane or outside the membrane to separate the vortex mixture. The membrane technology splitting method has the advantages of low energy consumption, simple operation, large batch volume, easy continuous operation, easy industrial scale-up, flexible device design and system application, and room temperature operation in most cases. [0003] According to the shape of the membrane, the membrane technology splitting method is divided into two types: liquid membrane splitting method and solid membrane splitting method. Chiral liquid membranes have a common disadvantage that is difficult to overcome, that is, poor stab...

Claims

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Application Information

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Patent Type & Authority Patents(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