CN109485628B - Chiral polyamide membrane and preparation method and application thereof - Google Patents
Chiral polyamide membrane and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a chiral polyamide membrane, a preparation method thereof and application thereof in chiral drug resolution. The chiral polyamide membrane takes a cellulose acetate membrane as a base membrane, and a chiral resolving agent ethylenediamine-beta-cyclodextrin is immobilized on the surface of the base membrane through a connecting agent trimesoyl chloride. The preparation method specifically comprises the steps of preparing the ethylenediamine modified-beta-cyclodextrin by respectively adopting a two-step synthesis method for beta-cyclodextrin, p-toluenesulfonyl chloride and anhydrous ethylenediamine, taking the ethylenediamine modified-beta-cyclodextrin as a chiral selector, taking a commercialized cellulose acetate material with high mechanical strength, strong compressive tightness, good chemical stability and low price as a base membrane material, selecting trimesoyl chloride as a connecting agent, and preparing the interface polyamide cellulose acetate membrane with chiral resolution capability by adopting an interface polymerization method. The chiral polyamide membrane has the advantages of low cost, simple preparation process and wide splitting objects.
Description
Technical Field
The invention belongs to the technical field of chiral resolution, and particularly relates to a chiral polyamide membrane, a preparation method thereof and application thereof in chiral drug resolution.
Background
The membrane technology resolution method is to use specific separation functional sites contained in or outside the membrane to resolve the racemic mixture. The membrane technology splitting method has the advantages of low energy consumption, simple operation, large batch processing amount, easy continuous operation, easy industrial amplification, flexible device design and system application, room temperature operation in most cases and the like.
The membrane technology splitting method is divided into a liquid membrane splitting method and a solid membrane splitting method according to the shape of a membrane. The chiral liquid film has a common defect which is difficult to overcome, namely poor stability, and the industrial application of the chiral liquid film is always greatly limited. The stability of the solid membrane for chiral separation is good, so that the method becomes a key research direction for chiral separation by a membrane method.
The chiral solid membrane is divided into three types, namely a body solid membrane, a modified solid membrane and a molecular imprinting solid membrane according to the characteristics of membrane materials and a preparation process. The solid film of the body has less film material and narrow use surface. The molecular engram membrane has strong specificity, each molecular engram membrane can only split one chiral substance, and the preparation process is complex. The modified solid membrane has good designability, high separation efficiency and wide application range, and becomes the focus research direction of chiral separation solid membranes. The method comprises the following steps of taking an alumina ceramic membrane as a passivation support, taking beta-CD as a solid membrane of a chiral selector, splitting D, L-phenylalanine, filtering the D-phenylalanine and the L-phenylalanine respectively through the membrane, and judging the two configurational truncations of the D-phenylalanine and the L-phenylalanine by using UV; the flow difference was used to preliminarily determine that the prepared membrane has a resolution effect on phenylalanine (Sucailian, Darongyo, 20319; and. cyclodextrin modified ceramic tube membranes split amino acid enantiomers. meeting paper of the second conference of membrane science and technology reports 2005, 09). Darongyi et al use beta-cyclodextrin as a chiral selector, a ceramic membrane as a base membrane material, epichlorohydrin as a cross-linking agent, the chiral recognition ability of a membrane prepared by splitting 1-methyl-6, 7-dihydroxy-1, 2,3, 4-tetrahydroisoquinoline gradually decreases with the increase of permeation time, and the balance is achieved after about 9 hours, and a permeation experiment of a membrane unit is carried out, so that the proportion of R-salsolenol to S-Salsolnol is changed from 0.87 to 1.55 (Darongyi, Sucai lotus, Wuhaiyan, Dengyelin. beta-cyclodextrin chiral membrane separation 1-methyl-6, 7-dihydroxy-1, 2,3, 4-tetrahydroisoquinoline. 2008, 06; reported by Beijing university of science and technology). Liu Shen and the like take beta-CD as chiral selection agents, respectively adopt Cellulose Acetate (CA) and Sodium Alginate (SA) as base membrane materials, and prepare CA/beta-CD and SA/beta-CD chiral membranes by a blending method. The chiral separation membrane is obtained by blending alpha-CD, benzyl cyclodextrin, p-methyl benzene sulfonic acid cyclodextrin, cyclodextrin water-soluble oligomer, 2, 4-dimethyl beta-CD and cellulose acetate, wherein the separation rates of tryptophan enantiomers are respectively 6.57%, 7.58%, 7.85%, 8.02% and 8.59%, and the separation rates of phenylalanine enantiomers are respectively 7.68%, 9.33%, 9.07%, 9.57% and 9.85%. The chemical cross-linked membrane is obtained by the reaction of CA and beta-CD, and the separation is carried out on tryptophan and phenylalanine, and the result shows that: the maximum separation rates of the chemical cross-linked membrane of CA and beta-CD to tryptophan and phenylalanine reach 9.9% and 10.9% respectively. (Liu Shen, gold Shimin, Wu Li Guang; Shuoshi paper for the preparation of chiral film based on beta-cyclodextrin and the resolution of tryptophan and phenylalanine enantiomers, Zhejiang university of industry; 2013, 06 months).
In general, the existing resolving agent has the problems of high preparation cost, harsh conditions and the like, and the rapid development of the resolving field is always restricted.
Disclosure of Invention
The chiral polyamide membrane is prepared by taking ethylenediamine-beta-cyclodextrin as a chiral resolving agent, cellulose acetate as a base membrane material and trimesoyl chloride as a connecting agent, and has the advantages of low cost, simple preparation process and wide resolving objects.
In order to solve the problems, the technical scheme adopted by the invention is as follows:
a chiral polyamide membrane uses a cellulose acetate membrane as a base membrane, and a chiral resolving agent ethylenediamine-beta-cyclodextrin is immobilized on the surface of the base membrane through a connecting agent of trimesoyl chloride.
Further, the preparation method of the ethylenediamine-beta-cyclodextrin comprises the following steps:
and 4, adding anhydrous ethylenediamine into the mono-6-tosyl-beta-cyclodextrin, wherein the mass ratio of the mono-6-tosyl-beta-cyclodextrin to the anhydrous ethylenediamine is (4-6) g: (24-36) mL, heating in an oil bath at 70-80 ℃ for 5-7h under the protection of nitrogen, carrying out reduced pressure evaporation to obtain unreacted ethylenediamine, then adding acetone, carrying out suction filtration, dissolving a filter cake in a water/methanol solution with the volume ratio of 3:1, then adding acetone, carrying out suction filtration to obtain white precipitate, repeatedly washing to remove residual ethylenediamine, and finally, carrying out vacuum drying on the filter cake at 50 ℃ for 72h to obtain ethylenediamine-beta-cyclodextrin.
The preparation method of the chiral polyamide membrane comprises the following steps:
and 2, soaking the pretreated and activated cellulose acetate membrane in 0.3-0.5 wt.% of trimesoyl chloride n-hexane for 20-24h, taking out, soaking in an aqueous solution containing 0.3-0.8 wt.% of ethylenediamine-beta-cyclodextrin and 0.1 wt.% of triethylamine for 20-24h, taking out, soaking in 0.5 wt.% of trimesoyl chloride n-hexane for 1min again, then carrying out curing treatment, taking out, and washing with purified water to remove residual solvent on the surface to obtain the chiral polyamide membrane.
Further, the mass fraction of the NaOH aqueous solution in the step 1 is 0.2-0.4%.
Further, in the step 2, the curing temperature is 50-70 ℃, and the curing time is 5-20 min.
The application of the chiral polyamide membrane in chiral drug resolution.
The application of the chiral polyamide membrane in the separation of chiral drugs warfarin.
The application of the chiral polyamide membrane in resolution of chiral drug tryptophan is provided.
Compared with the prior art, the invention has the following beneficial effects:
1. in the preparation process of the intermediate product of the mono-6-tosyl-beta-cyclodextrin, acetone is used as an organic solvent to remove unreacted p-toluenesulfonyl chloride in a crude product, so that the defect of long time consumption in the existing purification method is overcome.
2. The chiral separation solid membrane with low cost, simple preparation process and wide separation objects can be prepared by taking ethylenediamine-beta-cyclodextrin as a chiral resolving agent, cellulose acetate as a base membrane material and trimesoyl chloride as a connecting agent;
3. the chiral polyamide membrane prepared by the invention can be used for splitting warfarin and tryptophan enantiomers, and is less influenced by the environment in the membrane splitting process and good in stability.
4. The chiral polyamide membrane prepared by the invention has wide tolerance to pH value, and the tolerance range of pH is 3-9.
Drawings
FIG. 1 is a schematic diagram of the preparation process and structure of the chiral polyamide membrane of the present invention.
FIG. 2 is a surface electron micrograph of the cellulose acetate film and the chiral polyamide film prepared in example 1.
FIG. 3 is a cross-sectional electron microscope image of the cellulose acetate film and the prepared chiral polyamide film in example 1.
Fig. 4 is a result of resolution stability of the chiral polyamide membrane prepared in example 1.
Fig. 5 is a result of pH tolerance of the chiral polyamide film obtained in example 2, in which Sample is a test group and Control is a blank group.
Fig. 6 is a graph showing the results of the resolution of chiral polyamide membrane prepared in example 3 at different pH values for different drugs (a. nefopam, b. ketoprofen, c. ibuprofen, d. warfarin), where permate is the filtrate and Feed is the stock solution.
Detailed Description
The invention is further described with reference to specific examples.
The process and the structural schematic diagram of the preparation of the chiral polyamide membrane in the invention are shown in figure 1.
Example 1
Firstly, preparing an ethylenediamine-beta-cyclodextrin chiral polyamide membrane through the following steps, and then detecting the concentration ratio of two configurations in filtrate filtered by the chiral membrane and the concentration ratio of two configurations in stock solution through a verified HPLC method of chiral substances to be resolved to evaluate the resolution performance of the chiral polyamide membrane.
Synthesizing ethylenediamine-beta-cyclodextrin:
recrystallized beta-cyclodextrin (100g, 88mmol) was weighed into a 1000mL beaker containing 833mL of purified water. NaOH (10.95g, 0.27mol) was dissolved in 33mL of water and added dropwise to the suspension over 10min with magnetic stirring, and after completion of the addition, the suspension became a homogeneous and slightly yellowish solution. P-toluenesulfonyl chloride (p-TsCl, 16.82g, 0.09mol) was weighed and dissolved in 50mL of acetonitrile, and the solution was added dropwise to the above pale yellow reaction solution containing β -cyclodextrin, and after 75min, all the solution was added dropwise, and a large amount of white precipitate was formed. After stirring vigorously at 25 ℃ for 2.5 hours, 2mol/L aqueous HCl solution was added dropwise to the reaction mixture to reduce the pH to near neutrality. The suspension was then placed in a refrigerator at 4 ℃ overnight. The next day, the filter cake was filtered by suction, immersed in acetone to remove residual p-TsCl, after 24 hours, acetone was removed, the filter cake was recrystallized with water, and finally the filter cake was dried under vacuum at 70 ℃ overnight to give a white mono-6-tosyl- β -cyclodextrin product. Weighing 5g of mono-6-tosyl-beta-cyclodextrin into a 100mL round bottom flask, then adding 30mL of anhydrous ethylenediamine, heating in a 75 ℃ oil bath under the protection of nitrogen, ending the reaction after 6h, evaporating unreacted ethylenediamine under reduced pressure until the reaction liquid is in a syrup state, and cooling the reaction product to room temperature. Then 250mL of acetone was added, suction filtered, and the filter cake was dissolved in 60mL of a water/methanol (3:1, V/V) solution, followed by addition of 250mL of acetone, suction filtered to obtain a white precipitate, and this was repeated several times to remove the remaining ethylenediamine. Finally, the filter cake was dried under vacuum at 50 ℃ for 72h to give the final product.
Preparing an ethylenediamine-beta-cyclodextrin chiral polyamide membrane composite membrane:
(1) activating and pretreating a cellulose acetate membrane: the commercial cellulose acetate membrane with the aperture of 0.22 mu m is firstly soaked in purified water and cleaned, then the filter membrane is taken out and put into NaOH water solution to be heated in water bath at 35 ℃ for 40min, so that acetyl on the membrane is hydrolyzed. The membrane was then removed and rinsed 5 times with deionized water until the rinse was neutral.
(2) Soaking the pretreated activated cellulose membrane in 0.5 wt.% of trimesoyl chloride (TMC) n-hexane for 24 hours, taking out, soaking in an aqueous solution containing 0.3 wt.% of ethylenediamine-beta-cyclodextrin and 0.1 wt.% of Triethylamine (TEA), soaking in 50mL of 0.5 wt.% TMC n-hexane solution for 1min after 24 hours, oven-curing at 60 ℃ for 20min, taking out, repeatedly washing with purified water to remove residual solvent on the surface, and storing in deionized water at 4 ℃ for later use.
And (3) performance characterization:
the cellulose acetate film and the chiral polyamide composite film were observed by a scanning electron microscope, see fig. 2 and fig. 3. Two electron microscope photographs in fig. 2 are from left to right, which are surface electron microscope images of the cellulose acetate membrane of unmodified ethylenediamine-beta-cyclodextrin and the chiral polyamide membrane, respectively, and the magnification is 2000 times. The two electron micrographs in fig. 3 are cross-sectional electron micrographs from left to right of cellulose acetate film of unmodified ethylenediamine- β -cyclodextrin and chiral polyamide cellulose film, both at 2000-fold magnification.
As can be seen from the figure, the chiral polyamide cellulose membrane modified with the ethylenediamine-beta-cyclodextrin has a small pore size, which indicates that the ethylenediamine-beta-cyclodextrin is crosslinked and immobilized on the membrane through trimesoyl chloride.
Evaluation of film resolution stability:
selecting the tryptophan stock solution with the concentration of 0.025g/L, the filtration flow rate of 0.1mL/min, the pH value of the tryptophan solution of 6.5 and the filtration temperature of 25 ℃; filtering the chiral membrane for 12 hours, replacing a collector every 2 hours to collect filtrate, and detecting the resolution stability of the chiral membrane within 12 hours by an HPLC method. From fig. 4, the chiral polyamide membrane prepared has stable chiral resolution effect within 12h, and RSD is 4.8%.
Intra-and inter-membrane precision:
four batches of chiral polyamide membranes were prepared and the tryptophan solution was filtered through 8 layers of chiral membranes each time under optimal resolution conditions. The filtrate was checked for e.e% by HPLC. The resolution precision between different batches of chiral polyamide membranes prepared was explored. The precision of the resolution between membranes is shown in the following table:
TABLE 1 precision between films
As can be seen from the table, the prepared chiral polyamide membrane has stable chiral resolution effect.
Example 2
A method for preparing ethylenediamine-beta-cyclodextrin comprises the following steps:
(1) weighing recrystallized beta-cyclodextrin (90g, 79mmol), adding into a 1000mL beaker containing 800mL of purified water, dissolving NaOH (10g, 0.25mol) in 30mL of water, and adding dropwise into the suspension within 8min under magnetic stirring;
(2) after the beta-cyclodextrin suspension becomes a clear light yellow solution, weighing p-toluenesulfonyl chloride (p-TsCl, 16g, 0.086mol) to dissolve in 45mL of acetonitrile, dropwise adding the solution into the light yellow reaction solution containing the beta-cyclodextrin, and completely dropwise adding after 70min to generate a large amount of white precipitates;
(3) the reaction system is stirred vigorously for 2h at room temperature, and then 2 mol.L-1Adjusting the hydrochloric acid to be nearly neutral, and standing in a refrigerator at 4 ℃ for overnight; the next day, filtration was performed with suction, and the filter cake was immersed in acetone.
(5) And after 22 hours, removing acetone, adding water into the reaction crude product, recrystallizing a filter cake by using water, filtering to obtain filtrate, putting the filtrate into a refrigerator at the temperature of 4 ℃ to crystallize and separate out a product, performing suction filtration, and performing vacuum drying on the filter cake overnight at the temperature of 60 ℃ to obtain the mono-6-tosyl-beta-cyclodextrin product.
(6) Adding anhydrous ethylenediamine into a round-bottom flask containing mono-6-tosyl beta-cyclodextrin, wherein the addition mass ratio of the mono-6-tosyl beta-cyclodextrin to the anhydrous ethylenediamine is 4 g: 24mL of the reaction solution is heated in an oil bath at 80 ℃ for 5 hours under the protection of nitrogen, and then unreacted ethylenediamine is evaporated under reduced pressure.
(7) Then 200mL of acetone was added, suction filtered, and the filter cake was dissolved in 50mL of a water/methanol (3:1, V/V) solution, followed by addition of 200mL of acetone, suction filtered to obtain a white precipitate, and this was repeated several times to remove residual ethylenediamine. Finally, the filter cake is dried in vacuum for 72h at 50 ℃ to obtain the final product
Preparing ethylenediamine-beta-cyclodextrin chiral polyamide:
(1) activating and pretreating a cellulose acetate membrane: the commercial cellulose acetate membrane with the aperture of 0.22 mu m is firstly soaked in purified water and cleaned, then the filter membrane is taken out and put into NaOH aqueous solution to be heated in water bath at the temperature of 30 ℃ for 50min, so that acetyl on the membrane is hydrolyzed. The membrane was then removed and rinsed 6 times with deionized water until the rinse solution was neutral
(2) Soaking the pretreated activated cellulose membrane in 0.3 wt.% of trimesoyl chloride (TMC) n-hexane for 22 hours, taking out, soaking in an aqueous solution containing 0.5 wt.% of ethylenediamine-beta-cyclodextrin and 0.1 wt.% of Triethylamine (TEA), soaking in 50mL of a 0.5 wt.% TMC n-hexane solution for 1min after 22 hours, oven-curing at 50 ℃ for 30min, taking out, repeatedly washing with purified water to remove the surface residual solvent, and storing in deionized water at 4 ℃ for later use.
And (3) performance characterization:
evaluation of pH tolerance Range of chiral Polyamide Membrane
Selecting buffer solutions with pH values of 1, 3, 6, 9 and 11 as hydrolysis solutions, putting the prepared chiral polyamide membrane into the buffer solutions, simultaneously carrying out a blank control group, simultaneously putting the experimental group and the blank group into a constant-temperature oscillator to shake for 24 hours at 150 revolutions per hour, then respectively measuring the Total Organic Carbon (TOC) of the experimental group and the blank group, judging the hydrolysis conditions of the membrane under different pH values by comparing the TOC values of the experimental group and the blank group, and knowing that the prepared chiral polyamide membrane is stable in a pH value range of 3-9 within 24 hours as shown in FIG. 5.
The chiral polyamide membrane prepared in this example has a wide pH tolerance range.
Example 3
A method for preparing ethylenediamine-beta-cyclodextrin comprises the following steps:
(1) weighing recrystallized beta-cyclodextrin (110g, 96.8mmol), adding into a 1000mL beaker containing 850mL purified water, dissolving NaOH (12g, 0.3mol) in 40mL water, and adding dropwise into the suspension within 11min under magnetic stirring;
(2) after the beta-cyclodextrin suspension becomes a clear light yellow solution, weighing p-toluenesulfonyl chloride (p-TsCl, 18g, 0.096mol) to dissolve in 50mL of acetonitrile, dropwise adding the solution into the light yellow reaction solution containing beta-cyclodextrin, and after 80min, completely dropwise adding the solution, wherein a large amount of white precipitates are generated;
(3) the reaction system is stirred vigorously for 3 hours at room temperature, and then 2 mol.L-1Adjusting the hydrochloric acid to be nearly neutral, and standing in a refrigerator at 4 ℃ overnight; the next day, filtration was carried out, and the filter cake was immersed in acetone.
(5) After 30h, removing acetone, adding water into the reaction crude product, recrystallizing the filter cake with water, performing suction filtration, and drying the filter cake at 60 ℃ in vacuum overnight to obtain the mono-6-tosyl-beta-cyclodextrin product.
(6) Adding anhydrous ethylenediamine into a round-bottom flask containing mono-6-tosyl beta-cyclodextrin, wherein the addition mass of the mono-6-tosyl beta-cyclodextrin is 6 g: 36mL of the solution was heated in a 70 ℃ oil bath for 7 hours under nitrogen protection, and then unreacted ethylenediamine was distilled off under reduced pressure.
(7) Then 300mL of acetone was added, suction filtered, and the filter cake was dissolved in 70mL of a solution of water/methanol (3:1, V/V), then 300mL of acetone was added, suction filtered to obtain a white precipitate, and this was repeated several times to remove the remaining ethylenediamine. Finally, the filter cake is dried for 72h under vacuum at 50 ℃ to obtain the final product
Preparing ethylenediamine-beta-cyclodextrin chiral polyamide:
(1) activating and pretreating a cellulose acetate membrane: the commercial cellulose acetate membrane with the aperture of 0.22 mu m is firstly soaked in purified water and cleaned, then the filter membrane is taken out and put into NaOH water solution to be heated in water bath at 35 ℃ for 40min, so that acetyl on the membrane is hydrolyzed. The membrane was then removed and rinsed 6 times with deionized water until the rinse solution was neutral
(2) Soaking the pretreated activated cellulose membrane in 0.4 wt.% of trimesoyl chloride (TMC) n-hexane for 20 hours, taking out, soaking in an aqueous solution containing 0.8 wt.% of ethylenediamine-beta-cyclodextrin and 0.1 wt.% of Triethylamine (TEA), soaking in 50mL of a 0.5 wt.% TMC n-hexane solution for 1min after 20 hours, oven-curing at 60 ℃ for 20min, taking out, repeatedly washing with purified water to remove the surface residual solvent, and storing in deionized water at 4 ℃ for later use.
And (3) performance characterization:
evaluation of resolving power of chiral Polyamide Membrane
Selecting chiral medicament stock solution with the concentration of 0.025g/L, the filtration flow rate of 0.1mL/min, the pH values of the stock solutions of 4, 5 and 6 respectively, and the filtration temperature of 25 ℃; and (3) filtering the solution by using a chiral membrane for 3 hours, replacing a collector for collecting filtrate once every time of filtering, and detecting the e.e% of the filtrate and the stock solution by adopting an HPLC method. Fig. 6 is a resolution chart of the chiral polyamide film prepared in this example for chiral drugs such as ibuprofen, warfarin, nefopam, ketoprofen, and the like, and according to fig. 6, the resolution e.e% of the chiral polyamide film prepared in this example for warfarin is 9.7%.
Claims (3)
1. The application of the chiral polyamide membrane in the separation of chiral medicine warfarin is characterized in that:
the chiral polyamide membrane takes a cellulose acetate membrane as a base membrane, and a chiral resolving agent ethylenediamine-beta-cyclodextrin is immobilized on the surface of the base membrane through a connecting agent trimesoyl chloride;
the preparation method of the ethylenediamine-beta-cyclodextrin comprises the following steps:
step 1, adding NaOH solution into the beta-cyclodextrin suspension, wherein the mass ratio of NaOH to beta-cyclodextrin is (9-12) g: (90-110) g, adding p-toluenesulfonyl chloride after the suspension of the beta-cyclodextrin becomes clear light yellow solution, wherein the mass ratio of the p-toluenesulfonyl chloride to the beta-cyclodextrin is (16-18) g: (90-110) g;
step 2, stirring the reaction system obtained in the step 1 for 2-3h, and using 2 mol.L-1Adjusting the pH value to 7.0 by hydrochloric acid, standing at 4 ℃ for reaction for 12 hours, and immersing a filter cake into acetone for 24 hours after suction filtration;
step 3, removing acetone, adding water into the reaction crude product, recrystallizing, performing suction filtration, and performing vacuum drying on a filter cake at the temperature of 50-70 ℃ for 12 hours to obtain mono-6-tosyl-beta-cyclodextrin;
and 4, adding anhydrous ethylenediamine into the mono-6-tosyl-beta-cyclodextrin, wherein the volume ratio of the mass of the mono-6-tosyl-beta-cyclodextrin to the anhydrous ethylenediamine is (4-6) g: (24-36) mL, under the protection of nitrogen, heating in an oil bath at 70-80 ℃ for 5-7h, carrying out reduced pressure evaporation to obtain unreacted ethylenediamine, then adding acetone, carrying out suction filtration, dissolving a filter cake in a water/methanol solution with the volume ratio of 3:1, then adding acetone, carrying out suction filtration to obtain white precipitate, repeatedly washing to remove residual ethylenediamine, and finally, carrying out vacuum drying on the filter cake at 50 ℃ for 72h to obtain ethylenediamine-beta-cyclodextrin;
the preparation method of the chiral polyamide membrane comprises the following steps:
step 1, activating and pretreating a cellulose acetate membrane, namely soaking a commercial cellulose acetate membrane with the aperture of 0.22 mu m into purified water, cleaning the membrane, taking out the membrane, placing the membrane into a NaOH aqueous solution, heating the membrane in a water bath at 25-35 ℃ for 30-50min to hydrolyze acetyl on the membrane, taking out the membrane, and washing the membrane with deionized water until the pH value of washing liquor reaches 7.0;
and 2, soaking the pretreated activated cellulose acetate membrane in 0.3-0.5 wt.% of trimesoyl chloride n-hexane for 20-24h, taking out, soaking in an aqueous solution containing 0.3-0.8 wt.% of ethylenediamine-beta-cyclodextrin and 0.1 wt.% of triethylamine for 20-24h, taking out, soaking in 0.5 wt.% of trimesoyl chloride n-hexane for 1min again, carrying out curing treatment, taking out, and washing with purified water to remove residual solvent on the surface to obtain the chiral polyamide membrane.
2. Use according to claim 1, characterized in that: in the step 1, the mass fraction of the aqueous solution of NaOH is 0.2-0.4%.
3. Use according to claim 1, characterized in that: in the step 2, the curing temperature is 50-70 ℃, and the curing time is 5-20 min.
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