CN113457460A - Selective molecular filtration membrane material and preparation method and application thereof - Google Patents
Selective molecular filtration membrane material and preparation method and application thereof Download PDFInfo
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- CN113457460A CN113457460A CN202110740524.4A CN202110740524A CN113457460A CN 113457460 A CN113457460 A CN 113457460A CN 202110740524 A CN202110740524 A CN 202110740524A CN 113457460 A CN113457460 A CN 113457460A
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- 239000000463 material Substances 0.000 title claims abstract description 32
- 239000012528 membrane Substances 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000001914 filtration Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 150000001923 cyclic compounds Chemical class 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 11
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- -1 polyethylene Polymers 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 238000007731 hot pressing Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002033 PVDF binder Substances 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 7
- 239000000758 substrate Substances 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 1
- 150000002678 macrocyclic compounds Chemical class 0.000 abstract description 6
- 238000013329 compounding Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/26—Polyalkenes
-
- 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
- B01D67/0002—Organic membrane manufacture
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
- B01D71/34—Polyvinylidene fluoride
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
- B01D71/36—Polytetrafluoroethene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/48—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
- Y02A20/131—Reverse-osmosis
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a selective molecular filter membrane material and a preparation method and application thereof, belonging to the technical field of filter membrane materials. The invention firstly provides a compound for preparing a molecular filtration membrane material, which is prepared by reacting polyvinyl alcohol with a cyclic compound under the action of a catalyst, and then compounding the compound with a base material to prepare the molecular filtration membrane material. The invention prepares the nonpolar macrocyclic compound with stable structure, when the radius of the nonpolar molecule is smaller than the aperture of the macrocyclic compound, the nonpolar molecule can well pass through the annular hole, and the molecule with the radius larger than the aperture and the polar molecule can not pass through, thereby achieving the purpose of selectively separating the nonpolar molecule.
Description
Technical Field
The invention belongs to the technical field of filter membrane materials, and particularly relates to a molecular filter membrane material and a preparation method and application thereof.
Background
At present, the membrane separation technology is mainly applied to exchange and filtration of metal ions, filtration of biological cells and separation of suspended matters, the molecular-level filtration is mainly realized by a chromatographic column, the use of a molecular filtration membrane for separating molecules with different polarities is rarely reported, and the membrane separation has great advantages in application compared with the chromatographic column separation, so that the development of the molecular filtration membrane has important significance.
Disclosure of Invention
In order to solve the problems in the prior art, the invention firstly provides a compound for preparing a selective molecular filter membrane material, wherein the compound is used as the main component of a filter layer of the filter membrane material, is prepared by reacting polyvinyl alcohol and a cyclic compound PBCD under the action of a catalyst, is marked as PVA-PBCD and has the following structure
Wherein the cyclic compound PBCD has the following structure
Wherein R is-OH, -CH2OH or-C2H4OH。
The invention further provides a preparation method of the compound, which takes PVA and PBCD as raw materials, and the reaction temperature is 70-110 ℃ and the reaction time is 60-300min under the action of a catalyst, and the preparation route is as follows:
wherein, the catalyst of the reaction is benzenesulfonic acid, benzenesulfonic acid derivatives, concentrated sulfuric acid, concentrated phosphoric acid or oxalic acid.
Wherein the amount of PVA is 6: 1-3: 2 according to the mass ratio of-CHOH-to PBCD in the PVA.
Preferably, PVA1799 is used as PVA, in amounts corresponding to 180g of PVA1799 and 1.03mol of PBCD.
Wherein the cyclic compound PBCD is prepared by reacting a compound HQ-R with formaldehyde under the action of a template agent and a catalyst at 50-150 ℃ for 30-240 min, and the compound HQ-R has the following structure
Wherein R is-OH, -CH2OH or-C2H4OH, the synthetic route is as follows:
wherein, the catalyst in the preparation reaction of the cyclic compound PBCD is benzenesulfonic acid, benzenesulfonic acid derivatives, strongly acidic ion exchange resin, concentrated sulfuric acid, concentrated phosphoric acid or oxalic acid.
Wherein the template agent in the preparation reaction of the cyclic compound PBCD is calcium carbonate or football alkene with the particle size of 100-200 nm.
Wherein the molar ratio of the compound HQ-R to formaldehyde in the preparation reaction of the cyclic compound PBCD is 1: 1-1: 1.1.
The invention further provides a molecular filter membrane material, which comprises a filter layer and a base material, wherein the filter layer and the base material take a compound PVA-PBCD as a main component, and the base material is a polyethylene fiber membrane, a polyester PET fiber membrane, a polyvinylidene fluoride PDVF membrane or a polytetrafluoroethylene PTEF membrane.
The invention further discloses a preparation method of the molecular filter membrane material, which comprises the steps of dispersing PVA-PBCD in a solvent, coating the solvent on the surface of a base material, drying, and adhering the base material to the surface of the base material through hot-pressing and hot-melting.
Wherein, DMF, acetone or DMSO can be used as the solvent.
Preferably, 1 part of PVA-PBCD is dissolved in 3-10 parts of DMF, acetone or DMSO.
Preferably, the thickness of the coating on the surface of the base material is controlled to be 0.1-1.2 mm.
Preferably, the drying condition is drying at 50-110 ℃ for 30-150 min.
Preferably, the hot pressing condition is 120-180 ℃ for 5-15 min.
The invention further discloses application of the molecular filter membrane material, which is used for separating non-polar molecules and polar molecules in mixed liquor.
The invention has the beneficial effects that:
the invention prepares a nonpolar macrocyclic compound with stable structure, when the radius of a nonpolar molecule is smaller than the aperture of the macrocyclic compound, the nonpolar molecule can well pass through a ring hole, and the molecule with the radius larger than the aperture and a polar molecule can not pass through the macrocyclic compound, thereby achieving the purpose of selectively separating the nonpolar or weakly polar molecules;
the invention makes nonpolar macrocyclic compound with certain radius react with PVA, thus increasing density and uniformity of cyclic compound, after compounding with base material, the compound can be used as filtering membrane material for selective separation of molecular level, and has good application prospect.
Drawings
FIG. 1 shows the preparation of the cyclic compound of example 11H NMR spectrum;
FIG. 2 is a schematic view of a molecular filtration membrane according to example 3.
Detailed Description
Example 1
With a compound HQ-R (R is-CH)2OH) and formaldehyde are taken as raw materials, the dosage is 1 part and 1.05 part by weight, the heating temperature is controlled to be 50-150 ℃ under the condition of 1.1 part of template agent and 0.25 catalyst, the reaction time is controlled to be 30-120 min to prepare a cyclic compound (1,3,5,7,9(1,4) -pentabenzacyclodechane), the template agent adopts calcium carbonate microspheres, and the catalyst adopts benzenesulfonic acid to obtain the cyclic compound with the following structureThe substance (A) is a mixture of (B),1the H NMR spectrum is shown in FIG. 1.
Example 2
Polyvinyl alcohol PVA1799(180g) and the cyclic compound (1.03mol) prepared in example 1 are used as raw materials to produce a compound PVA-PBCD under the catalysis of concentrated sulfuric acid, the reaction temperature is controlled to be 70-110 ℃, and the reaction time is controlled to be 60-120 min.
Example 3
The PVA-PBCD prepared in the embodiment 2 is dispersed in a solvent, then coated on the surface of a base material, the thickness of the coating is 0.1-1.2 mm, the coating is dried at 50-110 ℃ for 30-150 min, then hot pressed at 120-180 ℃ for 5-15 min, and the PVA-PBCD and the base material are tightly adhered together through hot melting, so that the mechanical property of the material is improved, and the service life of the material is prolonged.
Application test example
The molecular filtration membrane prepared in example 3 was used for the selective separation of ethyl acetate from a mixture containing ethyl acetate, acetic acid, ethanol and water, and the test results were as follows:
1. separating a mixture of ethyl acetate, acetic acid, ethanol and water in a ratio of 90:2:5:3 to obtain a weak-polarity ethyl acetate liquid and a polar solution, wherein the purity of the weak-polarity ethyl acetate liquid is 99.26%.
2. A mixture of butyl acetate, butanol acetate, water 84:5:8:3 was separated to obtain a weakly polar ethyl acetate liquid with a purity of 98.82% and a polar solution.
3. Separating a mixture of ethyl formate, ethanol and water in a ratio of 88:2:6:4 to obtain a weak-polarity ethyl acetate liquid and a polar solution, wherein the purity of the weak-polarity ethyl acetate liquid is 99.11%.
The foregoing is a more detailed description of the invention in connection with specific/preferred embodiments and is not intended to limit the practice of the invention to those descriptions. Several alternatives or modifications to the described embodiments may be made without departing from the inventive concept and such alternatives or modifications should be considered as falling within the scope of the present invention.
Claims (10)
1. A compound for use in the preparation of a selective molecular filtration membrane material, characterized in that: the compound is used as the main component of a filter layer of a filter membrane material, is prepared by the reaction of polyvinyl alcohol and a cyclic compound PBCD under the action of a catalyst, is marked as PVA-PBCD and has the following structure
The cyclic compound PBCD has the following structure
Wherein R is-OH, -CH2OH or-C2H4OH。
2. A process for the preparation of a compound according to claim 1, characterized in that: PVA and PBCD are used as raw materials, the reaction temperature is 70-110 ℃ and the reaction time is 60-300min under the action of a catalyst, and the preparation route is as follows
3. A process for the preparation of a compound according to claim 2, characterized in that: the reaction is carried out under the action of a catalyst, wherein the catalyst is benzenesulfonic acid, benzenesulfonic acid derivatives, concentrated sulfuric acid, concentrated phosphoric acid or oxalic acid.
4. A process for the preparation of a compound according to claim 2 or 3, characterized in that: the mass ratio of-CHOH-to PBCD in the PVA is 6: 1-3: 2.
5. A process for the preparation of a compound according to any one of claims 2 to 4, characterized in that: the cyclic compound PBCD consists ofThe compound HQ-R and formaldehyde react for 30-240 min under the action of a catalyst and a template agent at the temperature of 50-150 ℃, and the compound HQ-R has the following structure
Wherein R is-OH, -CH2OH or-C2H4OH。
6. The process for the preparation of a compound according to claim 5, characterized in that: the catalyst is benzene sulfonic acid, benzene sulfonic acid derivatives, strong acid ion exchange resin, concentrated sulfuric acid, concentrated phosphoric acid or oxalic acid; the template agent is 100-200 nm calcium carbonate or football alkene.
7. A process for the preparation of a compound according to claim 5 or 6, characterized in that: the molar ratio of the HQ-R compound to the formaldehyde is 1: 1-1: 1.1.
8. A selective molecular filtration membrane material, characterized by: comprises a filter layer and a substrate, wherein the filter layer and the substrate are mainly composed of the PVA-PBCD compound of claim 1, and the substrate is a polyethylene fiber film, a polyester PET fiber film, a polyvinylidene fluoride PDVF film or a polytetrafluoroethylene PTEF film.
9. A method for preparing a molecular filtration membrane material according to claim 8, wherein: the PVA-PBCD is dispersed in a solvent, then coated on the surface of a substrate, dried and attached to the surface of the substrate through hot-pressing and hot-melting.
10. Use of a molecular filtration membrane material according to claim 8 for separating non-polar molecules from polar molecules in a mixed liquor.
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| CN202110740524.4A CN113457460B (en) | 2021-06-30 | 2021-06-30 | Selective molecular filtering membrane material and preparation method and application thereof |
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| CN202110740524.4A CN113457460B (en) | 2021-06-30 | 2021-06-30 | Selective molecular filtering membrane material and preparation method and application thereof |
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| US4846977A (en) * | 1986-10-21 | 1989-07-11 | The Dow Chemical Company | Method and device for separating polar from non-polar liquids using membranes |
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