Solvent activated cyclodextrin membrane for chiral separation as well as preparation method and application of solvent activated cyclodextrin membrane

Abstract

The invention relates to the technical field of chiral resolution, in particular to a solvent activated cyclodextrin membrane for chiral separation and a preparation method and application thereof.The preparation method comprises the steps that beta-CD and CDI are mixed in DMSO and stirred at the room temperature in inert gas, then excessive EDA is added, continuous stirring is conducted, and a mixed solution is obtained; performing vacuum concentration, washing, precipitating, filtering, repeating for multiple times, and drying to obtain a white powdery compound; activating through an organic solvent, washing and drying to obtain solvent activated cyclodextrin; the method comprises the following steps: dissolving cyclodextrin in deionized water to obtain a water-phase solution, and preparing the solvent-activated cyclodextrin membrane by taking an n-hexane solution of trimesoyl chloride as an organic-phase solution through a free interface polymerization method. Compared with the prior art, the cyclodextrin membrane prepared by the invention has a good separation effect on various amino acids, overcomes the problem of single resolution object of a chiral membrane in the prior art, and has important significance on design and preparation of a chiral separation membrane.

Description

Technical Field

[0001] The present invention relates to the technical field of chiral resolution, and more particularly to a solvent-activated cyclodextrin membrane for chiral separation and a preparation method thereof. Background Art

[0002] Chirality is a fundamental property of nature and has a profound impact on human life. Molecules that cannot coincide with their mirror images are called chiral molecules. Although different enantiomers of chiral molecules have similar physical and chemical properties, they can produce different biological effects in organisms. One enantiomer will exert a therapeutic effect, while the other may be ineffective or have toxic side effects. Therefore, the resolution of enantiomers is of great significance for the development of the industries in the field of life and health. Amino acids, as essential physiological components of the human body, mostly have chiral characteristics. Among them, D-amino acids need to be converted into L-amino acids in the human body before they can be absorbed and utilized. Once the D-amino acids exceed the conversion limit of the human body, amino acid poisoning will occur. Therefore, chiral resolution treatment must be carried out after the synthesis of amino acids.

[0003] Membrane separation technology is a simple and efficient separation technology, which has the characteristics of environmental friendliness, low energy consumption, and easy large-scale continuous production. According to the morphology of the membrane, the membrane can be divided into liquid membranes and solid membranes. The essence of liquid membrane separation is a liquid-liquid extraction process, which has high selectivity, but its short lifespan and poor stability have always limited its industrial application. Chiral solid membranes have better stability and are generally considered to be a very promising method for large-scale chiral resolution, with good application prospects.

[0004] Cyclodextrin is currently the most active chiral selector and has been proven to be useful for the separation of various amino acids. Enantiomers can reversibly bind to the cavity of cyclodextrin to form host-guest complexes, and the abundant hydroxyl groups on the outer surface of cyclodextrin can be functionally modified (such as esterification, amination, and etherification) to improve its chirality. However, the trade-off between the selectivity and flux of cyclodextrin membranes is still a problem, and the objects to be resolved are relatively single.

[0005] In the prior art, cyclodextrin-immobilized cellulose membranes and cyclodextrin / antibiotic composite membranes have been successfully applied in the field of chiral resolution.

[0006] For example, CN104001431A discloses a method for chiral resolution of tryptophan based on a β-cyclodextrin-immobilized cellulose membrane. This method realizes the effective resolution of racemic tryptophan by chemically bonding cyclodextrin to the cellulose membrane, but its resolution efficiency and stability still need to be improved.

[0007] In addition, CN115845644A proposes a composite membrane constructed using cyclodextrin and aminoglycoside antibiotics. This membrane is deposited on the surface of a porous support membrane through host-guest supramolecular interactions and its stability is enhanced by chemical crosslinking. Although it can achieve efficient resolution of tryptophan, it has limitations in the generality of amino acid racemates.

[0008] In addition, for the chiral membrane separation technologies disclosed in CN108671773A and CN1094885628A, although they can achieve effective resolution of enantiomers, they face problems such as a single separation target and limited flux due to excessive membrane thickness.

[0009] CN108671773A uses a cellulose acetate membrane as the base membrane and β-cyclodextrin or hydroxypropyl-β-cyclodextrin as the chiral selector. Although it can achieve good resolution of tryptophan and mandelic acid, the excessive membrane thickness limits its flux.

[0010] CN1094885628A uses ethylenediamine-β-cyclodextrin as the chiral selector and also faces the problem of flux caused by excessive membrane layer thickness.

[0011] In the prior art, although the resolution effect has been improved by changing the chiral selector and membrane material, there is still a need to break through in improving the chiral recognition ability and flux of the membrane. In particular, enhancing the chiral recognition ability by changing the structure of the chiral selector while maintaining the ultrathin characteristics of the membrane to achieve highly selective and high-throughput enantiomer separation is the shortcoming of the current technology and urgently needs to be continuously improved by researchers. Summary of the Invention

[0012] The purpose of the present invention is to overcome the defects existing in the prior art and provide a cyclodextrin membrane for chiral separation prepared by free interface polymerization, which has ultrathin characteristics. The present invention combines the high selectivity of solvent-activated cyclodextrin with the ultrathin characteristics of the free interface polymerization membrane, providing a new approach for achieving highly selective and high-throughput enantiomer separation membranes, and it has good application prospects for the resolution of amino acid racemates.

[0013] In the conceptual logic of the present invention, importantly, during the preparation process, the aminated cyclodextrin is activated by the solvent, which can effectively improve the chiral recognition ability. At the same time, as a reaction monomer for the interfacial polymerization method, it can provide chiral recognition sites to a large extent and construct a highly selective chiral separation membrane.

[0014] The purpose of the present invention can be achieved by the following technical solutions:

[0015] The first aspect of the present invention provides a preparation method for a solvent-activated cyclodextrin membrane for chiral separation, including the following steps:

[0016] S1: Mix β-CD (β-cyclodextrin) and CDI (N,N'-carbonyldiimidazole) in DMSO (dimethyl sulfoxide), stir at room temperature under an inert gas, then add an excessive amount of EDA (ethylenediamine), and subsequently continue continuous stirring to obtain a mixed solution.

[0017] S2: Vacuum concentrate the mixed solution obtained in S1, then wash, precipitate, and filter it in ethanol for multiple times, collect the obtained precipitate and dry it to obtain a white powdery compound.

[0018] S3: Activate the white powdery compound obtained in S2 with an organic solvent, then wash and dry it to obtain a solvent-activated cyclodextrin.

[0019] S4: Dissolve the solvent-activated cyclodextrin obtained in S3 in deionized water to obtain an aqueous solution, use a n-hexane solution of trimesoyl chloride as the organic phase solution, and prepare a solvent-activated cyclodextrin membrane by the free interface polymerization method.

[0020] Further, in S1, the usage ratios of β-CD, CDI, DMSO, and EDA are respectively 5 - 7 mmol: 40 - 50 mmol: 50 - 70 ml: 60 - 80 ml.

[0021] Further preferably, in S1, the usage ratios of β-CD, CDI, DMSO, and EDA are respectively 6.0 mmol: 46.2 mmol: 60 ml: 70 ml.

[0022] Further, in S3, the organic solvent is selected from one of N,N-dimethylformamide, methanol, and ethanol.

[0023] In S3, the activation time is 6 h.

[0024] Further, in S4, the concentration of the solvent-activated cyclodextrin in the aqueous solution is 0.1 - 0.3 wt%, and the concentration of trimesoyl chloride in the organic phase is 0.01 - 0.3 wt%.

[0025] Further preferably, the concentration of the solvent-activated cyclodextrin in the aqueous solution is 0.08 g activated cyclodextrin / 40 ml deionized water.

[0026] Further preferably, the concentration of trimesoyl chloride in the organic phase is 0.025 g trimesoyl chloride / 50 ml n-hexane.

[0027] Further, in S4, the free interface polymerization conditions are room temperature and the reaction time is 0.5 - 5 min.

[0028] The second aspect of the present invention provides a solvent-activated cyclodextrin membrane for chiral separation prepared by the above method.

[0029] The third aspect of the present invention provides an application of the above-mentioned solvent-activated cyclodextrin membrane in chiral separation.

[0030] Further, the object of chiral separation is phenylalanine, and the feed concentration of phenylalanine is 0.25-0.4 mg·ml -1 .

[0031] Further, the carrier solvent of phenylalanine is selected from one of water, methanol, and ethanol.

[0032] Further, when the object of chiral separation is phenylalanine, the enantiomeric excess value exceeds 96%.

[0033] The present invention has the following beneficial effects:

[0034] 2) The cyclodextrin membrane obtained in the present invention has high selectivity and high throughput. The main reason is that it has excellent chiral ability and ultrathin characteristics. The solvent-activated cyclodextrin obtained in the present invention has a certain structural change compared with the unactivated cyclodextrin, and this structural change increases the chiral ability of cyclodextrin.

[0035] 3) The cyclodextrin membrane prepared in the present invention has good separation effects on various amino acids, and preferably overcomes the problem of single chiral separation object in the prior art. The present invention is of great significance for the design and preparation of chiral separation membranes.

[0036] 3) The present invention provides a preparation method of a solvent-activated cyclodextrin membrane for chiral separation. Taking phenylalanine as an example, compared with the chiral separation membranes of the prior art, the resolution effect on phenylalanine is more excellent, the enantiomeric excess value reaches 96.64%, and the flux is 1.01 mmol·m -2 ·h -1 . BRIEF DESCRIPTION OF THE DRAWINGS

[0037] Figure 1 It is a schematic diagram of enantiomeric separation of the separation membranes prepared in the examples and comparative examples;

[0038] Figure 2 It is an AFM diagram of the cyclodextrin membrane prepared in Example 1 of the present invention;

[0039] Figure 3 It is a result comparison diagram of chiral resolution of phenylalanine using the cyclodextrin membranes obtained in Example 2, Example 3, Comparative Example 1, Comparative Example 2, and Comparative Example 3;

[0040] Figure 4 It is a surface electrostatic potential distribution diagram before and after solvent activation of the cyclodextrin of the present invention;

[0041] Figure 5For Comparative Example 1 of the present invention, XPS spectrum of C1s of the cyclodextrin film prepared in Example 4;

[0042] Figure 6 It is a comparative diagram of the results of chiral separation of phenylalanine using the cyclodextrin films obtained in Example 1 and Example 4;

[0043] Figure 7 It is the high performance liquid chromatography diagram of the cyclodextrin film prepared in Example 1 of the present invention;

[0044] Figure 8 It is the 1 1H NMR spectrum activated by different organic solvents. Detailed implementation manners

[0045] Overall, the preparation method of the solvent-activated cyclodextrin film for chiral separation in the present invention includes the following steps:

[0046] S1: Mix β-CD (6.81 g, 6.0 mmol) and CDI (7.50 g, 46.2 mmol) in DMSO (60 ml), and stir at room temperature for 12 hours under argon. Then add an excessive amount of EDA (70 ml, 1050 mmol), and subsequently continue to stir continuously for 12 hours to obtain a mixed solution;

[0047] S2: Vacuum concentrate the mixed solution obtained in S1, wash it in 500 ml of ethanol, precipitate, filter, and repeat three times to ensure obtaining pure functionalized cyclodextrin. Collect the obtained precipitate and dry it in a vacuum drying oven at 120 °C to obtain a white powdery compound;

[0048] S3: Based on the functionalized cyclodextrin obtained in S2, after activation with an organic solvent, and then washing and drying, a solvent-activated cyclodextrin is obtained;

[0049] S4: Weigh a certain mass of the obtained solvent-activated cyclodextrin based on S3 and dissolve it in deionized water to obtain an aqueous solution, and trimellitic acid trichloride solution as an organic solution, and prepare a cyclodextrin film by the free interface polymerization method;

[0050] In S3, the organic solvent is one of N,N-dimethylformamide, methanol, and ethanol.

[0051] In S3, the activation time is 6 h.

[0052] In S4, the aqueous phase concentration is 0.1 - 0.3 wt%, and the organic phase concentration is 0.01 - 0.3 wt%.

[0053] In S4, the free interface polymerization conditions are room temperature, and the reaction time is 0.5 - 5 min.

[0054] To further understand the present invention, the present invention will be described below in conjunction with embodiments. These descriptions are only to further explain the features and advantages of the present invention and are not intended to limit the claims of the present invention.

[0055] The percentage content not specifically stated can all be regarded as mass percentage.

[0056] The present invention will be described in detail below in conjunction with the accompanying drawings and specific embodiments. Features such as preparation means, materials, structures, or composition ratios not clearly stated in this technical solution are all regarded as common technical features disclosed in the prior art.

[0057] Example 1

[0058] The preparation method of the solvent-activated cyclodextrin membrane for chiral separation in this example includes the following steps:

[0059] (1) Amination of cyclodextrin: Mix β-CD (6.81 g, 6.0 mmol) and CDI (7.50 g, 46.2 mmol) in DMSO (60 ml), and stir at room temperature for 12 hours under argon. Then add an excess of EDA (70 ml, 1050 mmol), and then continue to stir continuously for 12 hours to obtain a mixed solution; Concentrate the obtained mixed solution under vacuum, wash it in 500 ml of ethanol, precipitate, filter, and repeat three times to ensure obtaining pure functionalized cyclodextrin. Collect the obtained precipitate and dry it in a vacuum drying oven at 120 °C to obtain a white powdery compound.

[0060] (2) Solvent activation of cyclodextrin: Activate the obtained aminated cyclodextrin with N,N-dimethylformamide solvent for 6 h, and then wash and dry it to obtain solvent-activated cyclodextrin.

[0061] (3) Preparation of cyclodextrin membrane: Weigh 0.08 g of the solvent-activated cyclodextrin and dissolve it in 40 ml of deionized water to obtain an aqueous solution, and weigh 0.025 g of trimesoyl chloride and dissolve it in 50 ml of n-hexane to obtain an organic solution. Measure 10 ml each from the organic phase and the aqueous phase for free interface polymerization reaction. Pour the aqueous phase into a glass petri dish, and then carefully pour 10 ml of the organic phase along the inner wall of the petri dish. After 1 min of interface polymerization reaction, a thin film can be seen between the aqueous phase and the organic phase, which is called CCD1. Transfer the cyclodextrin membrane formed by free interface polymerization to the AAO substrate, dry it at room temperature, and then store it in deionized water for further testing and characterization.

[0062] Example 2

[0063] (1) Amination of cyclodextrin: The same as step (1) in Example 1.

[0064] (2) Solvent-activated cyclodextrin: The obtained aminated cyclodextrin was activated with methanol solvent for 6 h, followed by washing and drying to obtain solvent-activated cyclodextrin.

[0065] (3) Preparation of cyclodextrin membrane: The same as step (3) in Example 1. At this time, the cyclodextrin membrane is called CCD2.

[0066] Example 3

[0067] (1) Amination of cyclodextrin: The same as step (1) in Example 1.

[0068] (2) Solvent-activated cyclodextrin: The obtained aminated cyclodextrin was activated with ethanol solvent for 6 h, followed by washing and drying to obtain solvent-activated cyclodextrin.

[0069] (3) Preparation of cyclodextrin membrane: The same as step (3) in Example 1. At this time, the cyclodextrin membrane is called CCD3.

[0070] Example 4

[0071] (1) Amination of cyclodextrin: The same as step (1) in Example 1.

[0072] (2) Preparation of cyclodextrin membrane: 0.08 g of aminated cyclodextrin was weighed and dissolved in 40 ml of deionized water to obtain an aqueous solution. 0.15 g of trimesoyl chloride was weighed and dissolved in 50 ml of n-hexane to obtain an organic solution. 10 ml was taken from each of the organic and aqueous phases for free interface polymerization reaction. The aqueous phase was poured into a glass petri dish, and then 10 ml of the organic phase was carefully poured along the inner wall of the petri dish. After 1 min of interface polymerization reaction, a thin film could be seen between the aqueous and organic phases, called CCD4. The cyclodextrin membrane formed by free interface polymerization was transferred onto the AAO substrate, dried at room temperature, and then stored in deionized water for further testing and characterization.

[0073] Comparative Example 1

[0074] (1) Amination of cyclodextrin: The same as step (1) in Example 1

[0075] (2) Preparation of cyclodextrin membrane: 0.08 g of aminated cyclodextrin was weighed and dissolved in 40 ml of deionized water to obtain an aqueous solution. 0.025 g of trimesoyl chloride was weighed and dissolved in 50 ml of n-hexane to obtain an organic solution. 10 ml was taken from each of the organic and aqueous phases for free interface polymerization reaction. The aqueous phase was poured into a glass petri dish, and then 10 ml of the organic phase was carefully poured along the inner wall of the petri dish. After 1 min of interface polymerization reaction, a thin film could be seen between the aqueous and organic phases, called CD1. The cyclodextrin membrane formed by free interface polymerization was transferred onto the AAO substrate, dried at room temperature, and then stored in deionized water for further testing and characterization.

[0076] Comparative Example 2

[0077] (1) Weigh 0.08 g of piperazine and dissolve it in 40 ml of deionized water to obtain an aqueous solution. Weigh 0.025 g of trimesoyl chloride and dissolve it in 50 ml of n - hexane to obtain an organic solution. Measure 10 ml each from the organic and aqueous solutions for the free - interface polymerization reaction. Pour the aqueous solution into a glass petri dish, and then carefully pour 10 ml of the organic solution along the inner wall of the petri dish. After 1 min of interface polymerization reaction, a thin film can be seen between the aqueous and organic phases, called PIP1. Transfer the polyamide film formed by free - interface polymerization to the AAO substrate, dry it at room temperature, and then store it in deionized water for further testing and characterization.

[0078] Verification Example 1

[0079] (1) Rinse the AAO substrate 3 times with deionized water and use it as the base film, called AAO1.

[0080] Enantiomeric resolution of the racemate in Example 1

[0081] The chiral separation ability of the cyclodextrin membrane was investigated using a diffusion device. The schematic diagram of enantiomer separation is as Figure 1 shown. Using the concentration gradient as the driving force for permeation, and high - performance liquid chromatography (HPLC) was used to analyze the components in the solution. Place a chiral composite membrane in the center of the diffusion cell, with an effective area of 1.77 cm 2 . The connection between the membrane and the side wall of the device was sealed with a rubber gasket. Add 50 ml of racemate solutions with different concentrations to the feed side, and add 50 ml of blank solvent to the permeation side. Take samples every 1 h, and each enantiomer separation experiment was repeated at least three times. Flux and enantioselectivity are common methods to evaluate the enantiomer separation performance of the membrane. The flux is calculated by the following formula:

[0082]

[0083] where Flux is the membrane flux (mmol·m -2 ·h -1 ), n is the molar amount of the permeating liquid passing through the membrane, calculated by the external standard method (mmol), A is the effective filtration area of the membrane (m 2 ), and t is the experimental time (h).

[0084] The enantioselectivity is calculated by the following formula and expressed as the enantiomeric excess value (ee%) of the filtrate:

[0085]

[0086] where A D(R) and A L(S)They respectively represent the peak areas of the D / (R)-enantiomer and the L / (S)-enantiomer in the filtrate chromatogram.

[0087] Unless otherwise specified, in each of the examples and comparative examples, the above method was used for testing the separation performance of the solvent-activated cyclodextrin membrane for chiral separation.

[0088] The variation of the separation effect of phenylalanine in Example 1 with different feed concentrations is shown in Table 1.

[0089] Table 1

[0090]

[0091]

[0092] The variation of the separation effect of phenylalanine in Example 1 with different carrier solvents is shown in Table 2.

[0093] Table 2

[0094] Carrier solvent <![CDATA[Flux of phenylalanine (mmol·m -2 ·h -1 )]]> Enantiomeric excess (ee%) Water 3.91 39.47 Methanol 1.42 42.79 Ethanol 1.01 96.64

[0095] The separation effects of different amino acids in Example 1 are shown in Table 3.

[0096] Table 3

[0097] Amino acid category <![CDATA[Flux of amino acids (mmol·m -2 ·h -1 )]]> Enantiomeric excess (ee%) 4-Chloro-phenylalanine 0.19 34.06 4-Fluoro-phenylalanine 0.15 21 Phenylalanine 1.01 96.64 Mandelic acid 2.01 67.52 Tryptophan 0.71 52.22

[0098] In Example 1, ofloxacin was also resolved, with the enantiomeric excess value (ee%) being 60.85 and the flux being 1.17 mmol·m -2 ·h -1 .

[0099] Figure 2 This is the AFM surface topography and thickness diagram of the cyclodextrin membrane prepared in Example 1 of the present invention. From Figure 2 it can be seen that the cyclodextrin membrane prepared in Example 1 has a relatively smooth membrane surface and a relatively thin membrane thickness.

[0100] According to the method of Example 1, the resolution effects of cyclodextrin membranes CCD2, CCD3, CD1, PIP1, and AAO1 on phenylalanine were investigated, where the feed concentration of the phenylalanine solution was 0.25 mg·ml -1 , the carrier solvent was ethanol, and the resulting figure is shown in Figure 3 . From Figure 3It can be seen that the chirality of the cyclodextrin film comes from the chiral selector cyclodextrin. Cyclodextrin was activated with methanol and ethanol, and compared with the unactivated one, the separation effect did not change significantly. Combining Table 1, it can be found that the activation of cyclodextrin with N,N-dimethylformamide significantly improved the separation effect. The reason is attributed to the appropriate change in the structure of cyclodextrin during the activation process of N,N-dimethylformamide. The surface electrostatic potential distribution diagrams before and after the change are as Figure 4 shown. From Figure 4 it can be seen that the surface electrostatic potential inside the cyclodextrin gradually moves in the negative direction. This change promotes the further increase in the binding energy of cyclodextrin to phenylalanine. The schematic diagram is as Figure 1 .

[0101] Figure 5 This is Comparative Example 1 of the present invention, and the XPS diagram of C1s of the cyclodextrin film prepared in Example 4. According to the method of Example 1, the resolution effect of cyclodextrin films CCD1 and CCD4 on phenylalanine was investigated. The feed concentration of the phenylalanine solution was 0.25 mg·ml -1 , and the carrier solvent was a mixed solution of water and methanol. The obtained diagram is as Figure 6 shown. From Figure 6 it can be seen that the concentration of TMC will affect the performance of the cyclodextrin film. Combining Figure 5 it can be found that excessive TMC will hydrolyze during the reaction, thereby affecting the crosslinking degree.

[0102] Figure 7 This is the high-performance liquid chromatography diagram of the cyclodextrin film prepared in Example 1 of the present invention. From Figure 7 it can be seen that the CCD1 film has excellent chiral separation effect. After separation by the CCD1 film, compared with the peak area of L-phenylalanine, the peak area of D-phenylalanine decreased significantly, indicating that L-phenylalanine can preferentially permeate through the CCD1 film.

[0103] Figure 8 is the 1 H NMR diagram of different organic solvents-activated Figure 8 . It can be seen that compared with other solvent activations, DMF activation will produce a more obvious chemical shift, indicating that the amino-β-CD after DMF activation has a stronger interaction with D / L-phenylalanine.

[0104] From the above results, it can be seen that the cyclodextrin film activated by the solvent provided by the present invention has good chiral resolution ability for amino acids, especially for DL-phenylalanine.

[0105] The body performs chiral resolution. The above description of the embodiments is provided to enable those of ordinary skill in the art to understand and use the invention. It is obvious that those skilled in the art can easily make various modifications to these embodiments and apply the general principles described herein to other embodiments without creative effort. Therefore, the present invention is not limited to the above embodiments, and the improvements and modifications made by those skilled in the art without departing from the scope of the present invention according to the disclosure of the present invention should be within the protection scope of the present invention.

Claims

1. A preparation method of a solvent-activated cyclodextrin membrane for chiral separation, characterized in that, It includes the following steps: S1: Mix β-CD and CDI in DMSO, stir at room temperature under inert gas, then add an excessive amount of EDA, and subsequently continue continuous stirring to obtain a mixed solution; S2: Vacuum concentrate the mixed solution obtained in S1, then wash, precipitate, and filter it in ethanol for multiple times, collect the obtained precipitate and dry it to obtain a white powdery compound; S3: Activate the white powdery compound obtained in S2 with an organic solvent, then wash and dry it to obtain a solvent-activated cyclodextrin; S4: Dissolve the solvent-activated cyclodextrin obtained in S3 in deionized water to obtain an aqueous solution, use a hexane solution of trimesoyl chloride as the organic solution, and prepare a solvent-activated cyclodextrin membrane by the free interface polymerization method.

2. The preparation method of a solvent-activated cyclodextrin membrane for chiral separation according to claim 1, wherein In S1, the usage ratios of β-CD, CDI, DMSO, and EDA are respectively 5 - 7 mmol: 40 - 50 mmol: 50 - 70 ml: 60 - 80 ml.

3. The preparation method of a solvent-activated cyclodextrin membrane for chiral separation according to claim 2, characterized in that, In S1, the usage ratios of β-CD, CDI, DMSO, and EDA are respectively 6.0 mmol: 46.2 mmol: 60 ml: 70 ml.

4. The preparation method of a solvent-activated cyclodextrin membrane for chiral separation according to claim 1, characterized in that, In S3, the organic solvent is selected from one of N,N-dimethylformamide, methanol, and ethanol; In S3, the activation time is 6 h.

5. The preparation method of a solvent-activated cyclodextrin membrane for chiral separation according to claim 1, wherein In S4, the concentration of the solvent-activated cyclodextrin in the aqueous solution is 0.1 - 0.3 wt%, and the concentration of trimesoyl chloride in the organic phase is 0.01 - 0.3 wt%.

6. The preparation method of a solvent-activated cyclodextrin membrane for chiral separation according to claim 1, characterized in that, In S4, the free interface polymerization conditions are room temperature and the reaction time is 0.5 - 5 min.

7. A solvent-activated cyclodextrin membrane for chiral separation prepared by the method according to any one of claims 1 to 6.

8. An application of the solvent-activated cyclodextrin membrane according to claim 7 in chiral separation.

9. Use of a solvent-activated cyclodextrin membrane according to claim 8, characterized in that, The object of chiral separation is phenylalanine, and the feed concentration of the phenylalanine is 0.25 - 0.4 mg·ml -1 ; The carrier solvent of the phenylalanine is selected from one of water, methanol, and ethanol.

10. Use of a solvent-activated cyclodextrin membrane according to claim 9, characterized in that, When the object of chiral separation is phenylalanine, the enantiomeric excess value exceeds 96%.

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