CN109126477A - A kind of preparation method of chiral separation film - Google Patents
A kind of preparation method of chiral separation film Download PDFInfo
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- CN109126477A CN109126477A CN201811068305.0A CN201811068305A CN109126477A CN 109126477 A CN109126477 A CN 109126477A CN 201811068305 A CN201811068305 A CN 201811068305A CN 109126477 A CN109126477 A CN 109126477A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0079—Manufacture of membranes comprising organic and inorganic components
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/46—Impregnation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
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Abstract
The present invention discloses a kind of preparation method of chiral separation film.The preparation method of the chiral separation film is the following steps are included: being dipped into polymer film in the aqueous solution containing metal ion, it is taken out after a period of time, it is transferred in the aqueous solution containing reducing agent, it shakes, the metal ion for being adsorbed on film surface is made to be converted into metal simple-substance, by load have metal film be immersed in containing sulfydryl, diphenol structure chiral molecules solution in, it is taken out after a period of time, unadsorbed chiral molecules is washed with deionized water, that is, form chiral separation film.The preparation method of the chiral separation film of the disclosure of the invention is simple, efficiently, mild condition is, it can be achieved that scale application.
Description
Technical field
The invention belongs to new separation material field, in particular to a kind of preparation method of chiral separation film.
Background technique
Chirality is the important feature of compound, and highly relevant with many important bioprocess.Chirality is in medicine, life
The influence of the equal own profound in the fields such as object, food additives and material.Due to limited, the synthetic technology of natural chiral amount of material
At high cost, the difficulties such as low yield, the hot subject that chiral resolution is studied at people are faced again.The chiral separation method of early stage is
Gas, liquid Chromatographic resolution method, but its derivation cumbersome is time-consuming, and it is possible to it can make analyte that racemization occur to shadow
Ring analysis result.People go back research and utilization crystallisation later, and chemical method and enzyme process carry out chiral resolution, but because its efficiency
It is low, complex steps and can not efficiently use.In recent years, UF membrane was because be considered as most possibly realizing industrialized fractionation skill
Art and by extensive concern.
Membrane separating method utilizes identification of the chiral selector to enantiomer, is coupled with membrane process and realizes chiral separation.Often
Chiral selector has: protein (BSA), amino acid, polysaccharide, super molecular compound etc..This kind of selective agent is usually and mapping
Body has specific binding site, because from the different mesh isolated to realization of enantiomer binding site number or binding ability
's.In the Patent right requirement, we utilize polymer surfaces functional group by adsorption of metal ions to film surface, with reduction
The metal ion for being adsorbed on film surface is reduced to metal simple-substance by agent, recycles the affinity interaction of sulfydryl, diphenol group and metal
Chiral molecules is fixed on film surface, the ultrafiltration membrane with chirality function is prepared with this.This patent can also be by changing gold
Belong to ion concentration to realize the regulation of membrane aperture, reaches chiral material height in conjunction with the adjusting in aperture and the chiral Recognition of chiral molecules
Imitate the purpose split.
Summary of the invention
The purpose of the invention is to overcome the shortage of prior art, a kind of side by absorption preparation chiral separation film is provided
Method, with the disadvantage for overcoming chiral separation film preparation cumbersome.
The present invention adopts the following technical scheme: a kind of preparation method of chiral separation film, comprising the following steps:
(1) dissolving metal salts are formed into homogeneous phase solution into deionized water；
(2) film is immersed in the aqueous solution of metal salt, adsorption of metal ions is in film surface；
(3) by film transfer into the aqueous solution containing reducing agent, the metal ion for being adsorbed on film surface is reduced to metal list
Matter；
(4) it dissolves the chiral molecules containing sulfydryl or catechol to form solution；
(5) film is moved on in the solution containing chiral molecules from the Transfer in Aqueous Solution containing reducing agent, adsorbs chiral molecules
To film surface
(6) it takes the film out, unadsorbed chiral molecules is washed with deionized water, form chiral separation film.
Further, the metal salt include silver nitrate, iron chloride, frerrous chloride, gold chloride, zinc chloride, nickel sulfate,
Copper sulphate；
Further, the concentration of the metal salt is 0.1 milligram every milliliter to 100 milligrams every milliliter, preferred concentration model
It encloses for 1~10mg/mL.
Further, the film is the blend film containing imidazoles, carboxyl, sulfonic group, pyridine, amino, hydroxyl group, or
It is the self-assembled micelle film that is formed by the polymer containing imidazoles, carboxyl, sulfonic group, pyridine, amino, hydroxyl group, homopore membrane, right
Claim film, non-to film forming.
Further, the reducing agent includes sodium borohydride, sodium citrate, lithium borohydride, ethamine, ethylenediamine, the third two
Amine, diethylene triamine, dipropylene diamine, Lithium Aluminium Hydride, amino acid.
Further, the chiral molecules containing sulfydryl is cystine, cysteine, lipoic acid, 5- sulfydryl-d- grape
Sugar and containing light propylhomoserin, cysteine, lipoic acid chiral polymer.
Further, the chiral molecules containing catechol is DOPA, dopamine, tannic acid, tea polyphenols, 3,4- bis-
Hydroxy phenylpropionic acid, different rosemary glycoside and the chiral polymer containing diphenol structure.
Further, the concentration of the chiral molecules containing catechol or sulfydryl in the solution be preferably 1~
100mg/mL。
The present invention has the advantages that compared with prior art
(1) chirality is prepared in the strong suction-operated of metal surface using sulfydryl or diphenol group the present invention provides a kind of
The method of seperation film.Compared to before this chemical graft, the methods of be blended, the scheme of the disclosure of the invention has easy to operate, general
The significant advantages such as adaptive is strong, adsorption strength is high, absorption is stable.
(2) preparation method for a kind of chiral separation film that this patent provides, related step can be in aqueous solution
It carries out, mild condition, is not necessarily to starvation, do not need using organic solvent, preparation process is environmentally protective, does not generate chemical dirt
Dye,
(3) implementation steps of this method are simple, do not need to be transformed existing equipment chiral separation film can be realized
Quantifying it is standby.
Detailed description of the invention
Fig. 1: the electronic photo of chiral caudacoria before modified；
Fig. 2: the surface chemical composition of chiral separation film；
Fig. 3: chiral separation film before modified after microstructure；
Fig. 4: the separating property of chiral separation film.
Specific embodiment
The present invention is further described with reference to embodiments, but described embodiment is not constituted to limit of the invention
System.In following embodiment, the structure and performance measurement of prepared chiral separation film: before and after scanning electron microscope opponent's sexual function
Structure is measured, and is analyzed by chemical component of the x-ray photoelectron spectroscopy to film surface；Pass through diffusion or filtration experiment opponent
The performance of property seperation film is measured.
Embodiment 1
A kind of surface layer is fine and close, and the preparation method of the chiral separation film of aperture 7nm, steps are as follows:
(1) prepare the two big small identical self-assembled micelle film formed by the polymer containing carboxyl, be with concentration
0.5mg/ml tetra chlorauric acid homogeneous phase solution；
(2) two big small identical ultrafiltration membrane is put into above-mentioned tetra chlorauric acid solution, 6h is adsorbed in room temperature concussion；
(3) then the film adsorbed is cleaned with deionized water；
(4) sodium borohydride solution for being 0.1mg/ml with concentration, cleaned film is put into the solution, room temperature concussion,
Carry out reduction reaction 8h；
(5) film is taken out, two films are respectively put into two culture dishes by deionized water cleaning；
(6) match the L-cysteine solution and D-Cys solution that concentration is 5mg/ml, it is molten by prepare two kinds
Liquid is poured into respectively in above-mentioned two culture dish remittance, is put into shaking table, absorption is for 24 hours；
(7) film that above-mentioned steps are cleaned with PBS, washes away extra cysteine；After tested, cysteine is successfully adsorbed on
Film surface, and remain the structure of former film.
(8) above-mentioned film is fitted into disperser, carries out Protein transport test, the final film for adsorbing L-cysteine turns
Fortune flux is 2.4nmol/cm2, the transhipment flux for adsorbing the film of D-Cys is 1.83nmol/cm2, chirality selection coefficient
(αL/D) it is 1.31.
Embodiment 2
A kind of micellar structure, the chiral separation membrane preparation method of aperture 11nm, steps are as follows:
(1) prepare the two big small identical self-assembled micelle film formed by the polymer containing pyridine, be with concentration
0.5mg/ml tetra chlorauric acid homogeneous phase solution；
(2) above-mentioned two equal-sized micella films are put into above-mentioned tetra chlorauric acid solution, 6h is adsorbed in room temperature concussion；
(3) then the film adsorbed is cleaned with deionized water；
(4) sodium citrate solution for being 0.1mg/ml with concentration, cleaned film is put into the solution, room temperature concussion,
Carry out reduction reaction 8h；
(5) film is taken out, two films are respectively put into two culture dishes by deionized water cleaning；
(6) match the L-cysteine solution and D-Cys solution that concentration is 5mg/ml, it is molten by prepare two kinds
Liquid is poured into respectively in above-mentioned two culture dish remittance, is put into shaking table, absorption is for 24 hours；
(7) film that above-mentioned steps are cleaned with PBS, washes away extra cysteine；
Fig. 1 be chiral separation film prepared by embodiment 2 before modified after electronic photo.Wherein Fig. 1 a is before modified
The electronic photo of micella film, Fig. 1 b be it is gold-plated after electronic photo, Fig. 1 c be adsorb cysteine after electronic photo.It can see
Out, with the progress of preparation process, different colors can be presented in film.
Fig. 2 is the surface chemical composition of chiral separation film.Wherein Fig. 2 a1,a2, b1,b2Illustrate film uniform adsorption gold, half Guang
Propylhomoserin.a3The Au of absorption L-cysteine caudacoria is represented, the content of S element shows that L-cysteine is successfully adsorbed on film surface.
Similarly, b3The Au of absorption D-Cys caudacoria is represented, the content of S element shows that cysteine is successfully adsorbed on film surface.
Fig. 3 be in embodiment 2 chiral separation film before modified after microstructure；Micella film is microcosmic after illustrating before modified
Structure does not change.This preparation method has been effectively maintained the structure of former film.
(8) above-mentioned film is fitted into disperser, carries out Protein transport test, the final film for adsorbing L-cysteine turns
Fortune flux is 6.33nmol/cm2, the transhipment flux for adsorbing the film of D-Cys is 3.56nmol/cm2, chirality selection coefficient
(αL/D) it is 1.78.As shown in figure 4, L-cysteine is more advantageous to the transhipment of BSA than D-Cys, and micella film have it is good
Good selectivity.
Embodiment 3
A kind of micellar structure, the chiral separation membrane preparation method of aperture 6.8nm, steps are as follows:
(1) prepare the two big small identical blend film containing sulfonic group, be that 1mg/ml tetra chlorauric acid is equal with concentration
Phase solution；
(2) above-mentioned two equal-sized micella films are put into above-mentioned tetra chlorauric acid solution, room temperature concussion, absorption is for 24 hours；
(3) then the film adsorbed is cleaned with deionized water；
(4) ethylenediamine solution for being 0.1mg/ml with concentration, cleaned film is put into the solution, room temperature concussion, into
Row reduction reaction 8h；
(5) film is taken out, two films are respectively put into two culture dishes by deionized water cleaning；
(6) match the L-3,4 dihydroxyphenylalanine amine and D- dopamine solution that concentration is 5mg/ml, prepare two kinds of solution are fallen respectively
Enter in above-mentioned two culture dish remittance, is put into shaking table, absorption is for 24 hours；
(7) film that above-mentioned steps are cleaned with PBS, washes away extra dopamine；After tested, dopamine is successfully adsorbed on film table
Face, and remain the structure of former film.
(8) above-mentioned film is fitted into disperser, carries out Protein transport test, the transhipment of the final film for adsorbing L-3,4 dihydroxyphenylalanine amine
Flux is 1.51nmol/cm2, the transhipment flux for adsorbing the film of D- dopamine is 1.87nmol/cm2, chirality selection coefficient (αL/D)
It is 0.81.
Embodiment 4
A kind of equal pore structure, aperture 14nm chiral separation film preparation method, steps are as follows:
(1) prepare the two big small identical blend film containing amino group, be that 3mg/ml tetra chlorauric acid is homogeneous with concentration
Solution；
(2) above-mentioned two equal-sized homopore membranes are put into above-mentioned tetra chlorauric acid solution, 2h is adsorbed in room temperature concussion；
(3) then the film adsorbed is cleaned with deionized water；
(4) sodium borohydride solution for being 0.1mg/ml with concentration, cleaned film is put into the solution, room temperature concussion,
Carry out reduction reaction 8h；
(5) film is taken out, two films are respectively put into two culture dishes by deionized water cleaning；
(6) match the L-3,4 dihydroxyphenylalanine amine and D- dopamine solution that concentration is 5mg/ml, prepare two kinds of solution are fallen respectively
Enter in above-mentioned two culture dish remittance, is put into shaking table, absorption is for 24 hours；
(7) film that above-mentioned steps are cleaned with PBS, washes away extra dopamine；；After tested, dopamine is successfully adsorbed on film
Surface, and remain the structure of former film.
(8) above-mentioned film is fitted into disperser, carries out Protein transport test, the transhipment of the final film for adsorbing L-3,4 dihydroxyphenylalanine amine
Flux is 4.98nmol/cm2, the transhipment flux for adsorbing the film of D- dopamine is 3.25nmol/cm2, chirality selection coefficient (αL/D)
It is 1.53.
Embodiment 5
A kind of preparation method of the polysulfones chiral separation film of aperture 7nm, steps are as follows:
(1) prepare the two big small identical blend film containing imidazole group, be that 0.5mg/ml tetra chlorauric acid is equal with concentration
Phase solution；
(2) above-mentioned two equal-sized commercial membranes are put into above-mentioned tetra chlorauric acid solution, 12h is adsorbed in room temperature concussion；
(3) then the film adsorbed is cleaned with deionized water；
(4) sodium borohydride solution for being 0.1mg/ml with concentration, cleaned film is put into the solution, room temperature concussion,
Carry out reduction reaction 8h；
(5) film is taken out, two films are respectively put into two culture dishes by deionized water cleaning；
(6) match the l-cysteine and D- cystine solution that concentration is 5mg/ml, prepare two kinds of solution are fallen respectively
Enter in above-mentioned two culture dish remittance, is put into shaking table, absorption is for 24 hours；
(7) film that above-mentioned steps are cleaned with PBS, washes away extra cystine；After tested, cystine is successfully adsorbed on film table
Face, and remain the structure of former film.
(8) above-mentioned film is fitted into disperser, carries out Protein transport test, the transhipment of the final film for adsorbing l-cysteine
Flux is 4.02nmol/cm2, the transhipment flux for adsorbing the film of D- cystine is 4.93nmol/cm2, chirality selection coefficient (αL/D)
It is 0.82.
Claims (8)
1. a kind of preparation method of chiral separation film, which comprises the following steps:
(1) dissolving metal salts are formed into homogeneous phase solution into deionized water；
(2) film is immersed in the aqueous solution of metal salt, adsorption of metal ions is in film surface；
(3) by film transfer into the aqueous solution containing reducing agent, the metal ion for being adsorbed on film surface is reduced to metal simple-substance；
(4) it dissolves the chiral molecules containing sulfydryl or catechol to form solution；
(5) film is moved on in the solution containing chiral molecules from the Transfer in Aqueous Solution containing reducing agent, chiral molecules is made to be adsorbed onto film
Surface
(6) it takes the film out, unadsorbed chiral molecules is washed with deionized water, form chiral separation film.
2. a kind of preparation method of chiral separation film according to claim 1, which is characterized in that the metal salt includes
Silver nitrate, iron chloride, frerrous chloride, gold chloride, zinc chloride, nickel sulfate, copper sulphate.
3. a kind of preparation method of chiral separation film according to claim 1, which is characterized in that the metal salt it is dense
Degree is 0.1 milligram every milliliter to 100 milligrams every milliliter, and preferred concentration range is 1~10mg/mL.
4. a kind of preparation method of chiral separation film according to claim 1, which is characterized in that the film is to contain miaow
The blend film of azoles, carboxyl, sulfonic group, pyridine, amino, hydroxyl group, or by containing imidazoles, carboxyl, sulfonic group, pyridine, amino,
It is self-assembled micelle film that the polymer of hydroxyl group is formed, homopore membrane, symmetric membrane, non-to film forming.
5. a kind of preparation method of chiral separation film according to claim 1, which is characterized in that the reducing agent includes
Sodium borohydride, sodium citrate, lithium borohydride, ethamine, ethylenediamine, propane diamine, diethylene triamine, dipropylene diamine, Lithium Aluminium Hydride, amino
Acid.
6. a kind of preparation method of chiral separation film according to claim 1, which is characterized in that the hand containing sulfydryl
Property molecule be cystine, cysteine, lipoic acid, 5- sulfydryl-d- glucose and contain light propylhomoserin, cysteine, lipoic acid
Chiral polymer.
7. a kind of preparation method of chiral separation film according to claim 1, which is characterized in that described contains catechol
Chiral molecules be DOPA, dopamine, tannic acid, tea polyphenols, 3,4- dihydroxy benzenes propionic acid, different rosemary glycoside and contain two
The chiral polymer of phenol structure.
8. a kind of preparation method of chiral separation film according to claim 1, which is characterized in that described contains catechol
Or the concentration of the chiral molecules of sulfydryl in the solution is preferably 1~100mg/mL.
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Cited By (4)
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| CN111701467A (en) * | 2020-05-26 | 2020-09-25 | 浙江工业大学 | Method for improving pollution resistance of homogeneous pore membrane by utilizing covalent bond layer-by-layer self-assembly |
| CN112546884A (en) * | 2020-11-18 | 2021-03-26 | 国网山东省电力公司电力科学研究院 | Preparation method of polyvinylidene fluoride modified membrane, polyvinylidene fluoride modified membrane and application |
| CN113499693A (en) * | 2021-08-05 | 2021-10-15 | 四川华造宏材科技有限公司 | Chemical stimulus response anti-pollution reverse osmosis membrane and preparation method thereof |
| CN113828171A (en) * | 2021-10-08 | 2021-12-24 | 山东大学 | Preparation of mercapto compound functionalized graphene oxide film and application of mercapto compound functionalized graphene oxide film in chiral separation |
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| CN111701467B (en) * | 2020-05-26 | 2022-05-10 | 浙江工业大学 | Method for improving pollution resistance of homogeneous pore membrane by utilizing covalent bond layer-by-layer self-assembly |
| CN112546884A (en) * | 2020-11-18 | 2021-03-26 | 国网山东省电力公司电力科学研究院 | Preparation method of polyvinylidene fluoride modified membrane, polyvinylidene fluoride modified membrane and application |
| CN113499693A (en) * | 2021-08-05 | 2021-10-15 | 四川华造宏材科技有限公司 | Chemical stimulus response anti-pollution reverse osmosis membrane and preparation method thereof |
| CN113828171A (en) * | 2021-10-08 | 2021-12-24 | 山东大学 | Preparation of mercapto compound functionalized graphene oxide film and application of mercapto compound functionalized graphene oxide film in chiral separation |
| CN113828171B (en) * | 2021-10-08 | 2022-11-04 | 山东大学 | Preparation of mercapto compound functionalized graphene oxide film and application of mercapto compound functionalized graphene oxide film in chiral separation |
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Application publication date: 20190104 |