CN110559878B - Covalent organic framework @ metal organic framework composite membrane and preparation method thereof - Google Patents
Covalent organic framework @ metal organic framework composite membrane and preparation method thereof Download PDFInfo
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
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- 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
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/12—Composite membranes; Ultra-thin membranes
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- 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
Abstract
The invention discloses a covalent organic framework @ metal organic framework composite membrane and a preparation method thereof, wherein the method comprises the following steps: dissolving p-benzaldehyde and tetra (4-aminophenyl) methane in anhydrous dioxane to obtain a mixed solution A, adding an acetic acid aqueous solution into the mixed solution A, and then reacting at 100-210 ℃ for 24-72 hours to obtain a covalent organic framework material; dissolving metal salt, ligand and the obtained covalent organic framework material in a solvent to obtain a mixed solution B, and reacting at 100-210 ℃ for 4-24 h to obtain a covalent organic framework @ metal organic framework material; dissolving polyether amide in ethanol to obtain an alcohol solution of polyether amide, stirring for 2-4H at 60-120 ℃, adding the obtained covalent organic framework @ metal organic framework material into the alcohol solution of polyether amide, stirring for 9-24H at room temperature to obtain a membrane casting solution, and then casting the membrane casting solution to form a membrane to obtain the covalent organic framework @ metal organic framework composite membrane applicable to H2/CO2Separation of (4).
Description
(I) technical field
The invention relates to a simple, efficient and excellent-performance covalent organic framework @ metal organic framework composite membrane and a preparation method thereof, and belongs to the technical field of gas separation.
(II) background of the invention
Carbon dioxide is a greenhouse gas, one of the main pollutants of atmospheric pollution, and can cause destructive consequences to the environment in the long run, thereby capturing the dioxideCarbon is a direct solution to suppress its harmful effects on the environment. Carbon capture prior to combustion includes syngas (including H)2And CO) with steam to form H2And CO2. During the past two decades, the development and application of membranes that selectively control the passage of different gases through it, often for separation purposes, has attracted extensive interest in research-oriented industrial applications, and the main advantages of membrane separation over other separation methods are energy/cost efficiency, for H2And CO2Has effective gas separation selectivity, and can be used in H2CO capture during combustion2Indicating its suitability as a clean fuel.
The research on the novel membrane material has been receiving attention from both academia and industry because the novel membrane material has important application value in many fields, especially in energy-saving separation technology. In recent years, covalent organic frameworks are novel porous materials consisting of strong covalent bonds, and due to excellent structural flexibility, large surface area, adjustable pore size, extremely high thermal stability and low density, covalent organic framework materials in various forms are widely researched in aspects of gas storage, separation, catalysis, energy storage and the like. However, the covalent organic framework material is easy to inactivate when meeting water vapor, and the application of the covalent organic framework material in separation is influenced, so that the effective solution of the problem is very important.
Disclosure of the invention
In order to overcome the defects in the prior art, the invention aims to provide a covalent organic framework @ metal organic framework composite membrane and a preparation method thereof. The composite membrane material obtained by the method is used for H2/CO2Has good selectivity.
The technical scheme of the invention is as follows:
a covalent organic framework @ metal organic framework composite membrane is prepared by the following steps:
(1) dissolving p-benzaldehyde and tetra (4-aminophenyl) methane in anhydrous dioxane to obtain a mixed solution A, adding an acetic acid aqueous solution with the concentration of 3-6 mol/L into the mixed solution A while violently stirring, uniformly stirring, placing into a high-pressure reaction kettle, reacting for 24-72 hours at 100-210 ℃, and after the reaction is completed, washing and drying the obtained reactant A to obtain a covalent organic framework material; the mass ratio of the p-benzaldehyde to the tetra (4-aminophenyl) methane is 0.4-0.8: 1, the volume consumption of the anhydrous dioxane is 70-90 mL/g based on the mass of the p-benzaldehyde; the addition amount of the acetic acid aqueous solution is 15-30 mL/g based on the mass of the p-benzaldehyde in the mixed solution A;
(2) dissolving metal salt, ligand and the covalent organic framework material obtained in the step (1) in a solvent, mixing, performing ultrasonic dispersion uniformly to obtain a mixed solution B, placing the mixed solution B in a high-pressure reaction kettle, reacting for 4-24 hours at 100-210 ℃, washing and drying a reactant B after complete reaction to obtain a covalent organic framework @ metal organic framework material; the ligand is 2-methylimidazole or trimesic acid; the mass ratio of the metal salt to the ligand to the covalent organic framework material is 2-8: 6.5-35: 1-2;
(3) dissolving polyether amide in ethanol to obtain an alcohol solution of polyether amide, stirring for 2-4 h at 60-120 ℃, adding the covalent organic framework @ metal organic framework material obtained in the step (2) into the alcohol solution of polyether amide, stirring for 9-24 h at room temperature to obtain a casting solution, and then casting the casting solution to form a film to obtain a covalent organic framework @ metal organic framework composite film; the adding amount of the ethanol is 10-25 mL/g based on the mass of the polyether amide; the mass ratio of the covalent organic framework @ metal organic framework material to the polyether amide is 1: 2 to 8.
Further, in the step (1), the washing and drying time is as follows: the obtained reactant A is washed with anhydrous dioxane and anhydrous tetrahydrofuran for multiple times and dried at room temperature to obtain the covalent organic framework material.
Further, in the step (2), the metal salt is a Zn salt, a Co salt, a Cu salt or an Fe salt.
Further, in the step (2), the solvent is methanol or N, N-dimethylformamide.
Further, in the step (2), the adding amount of the solvent is 50-100 mL/g based on the mass of the covalent organic framework material.
Further, in the step (2), the washing and drying processes are as follows: and washing the obtained reactant B with methanol for multiple times, and drying at room temperature to obtain the covalent organic framework @ metal organic framework material.
Further, in the step (3), the casting film-forming process comprises: and pouring the casting solution on a Teflon disc, drying for 24 hours at room temperature, and then removing residual solvent in a vacuum drying oven at 45 ℃ for 24 hours to obtain the covalent organic framework @ metal organic framework composite membrane.
The covalent organic framework @ metal organic framework composite membrane provided by the invention is applied to H2/CO2Separation of (4).
Compared with the prior art, the invention has the beneficial effects that:
(1) the operation method is simple and is suitable for industrial production;
(2) effectively improve H2/CO2Gas selectivity of (a);
(3) the metal organic framework material is combined with the covalent organic framework material, so that the problem of water vapor inactivation of the covalent organic framework material is effectively avoided.
(IV) detailed description of the preferred embodiments
The present invention will be described in detail below with reference to specific examples, but the present invention is not limited to the following examples, and various modifications and implementations are included within the technical scope of the present invention without departing from the content and scope of the present invention.
Example 1:
first, 24mg of p-benzaldehyde and 40mg of tetrakis (4-aminophenyl) methane were dissolved in 2mL of anhydrous dioxane, and 0.4mL of a 3M aqueous solution of acetic acid was added thereto with vigorous stirring, and the mixture was placed in a high-pressure reactor after being stirred uniformly and reacted at 100 ℃ for 3 days. And washing the obtained product for multiple times by using anhydrous dioxane and anhydrous tetrahydrofuran, and drying the product at room temperature to obtain the covalent organic framework material. 0.733 g of zinc acetate and 0.985g of 2-methylimidazole are respectively dissolved in 20mL of methanol, 0.1g of the covalent organic framework material prepared by the method is dissolved in 10mL of methanol, the covalent organic framework material and the methanol are uniformly dispersed by ultrasound after mixing, and the covalent organic framework material is placed in a high-pressure reaction kettle to react for 4 hours at the temperature of 120 ℃. And washing the solution with methanol for three times, and drying the solution at room temperature to obtain the covalent organic framework @ metal organic framework material. Dissolving 2.1g of polyether amide in 40mL of ethanol solution, stirring for 2h at 80 ℃, adding 0.4g of the covalent organic framework @ metal organic framework material, and stirring for 10h at room temperature to obtain the membrane casting solution. And pouring the casting solution on a Teflon disc, drying for 24 hours at room temperature, and then removing residual solvent in a vacuum drying oven at 45 ℃ for 24 hours to finally obtain the covalent organic framework @ metal organic framework composite membrane.
The covalent organic framework @ metal organic framework composite membrane is used for gas permeation test analysis. By using self-developed equipment to treat mixed gas H2/CO2(30/70 vol%) covalent organic framework @ metal organic framework composite membranes were evaluated at 30 ℃ and a feed pressure of 1bar, N2The sweep gas flow rate was 30mL (STP)/min, and the permeate was analyzed by gas chromatography. According to the result, H2/CO2The selectivity of (A) was 14.7.
Example 2:
first, 24mg of p-benzaldehyde and 40mg of tetrakis (4-aminophenyl) methane were dissolved in 2mL of anhydrous dioxane, and 0.4mL of a 3M aqueous solution of acetic acid was added thereto with vigorous stirring, and the mixture was placed in a high-pressure reactor after being stirred uniformly and reacted at 100 ℃ for 3 days. And washing the obtained product for multiple times by using anhydrous dioxane and anhydrous tetrahydrofuran, and drying the product at room temperature to obtain the covalent organic framework material. 0.96g of ferric chloride and 0.84g of trimesic acid are respectively dissolved in 20mL of N, N-dimethylformamide solvent, 0.1g of the covalent organic framework material prepared by the method is dissolved in 10mL of N, N-dimethylformamide solvent, the covalent organic framework material is uniformly dispersed by ultrasonic after mixing, and the mixture is placed in a high-pressure reaction kettle and reacts for 12 hours at the temperature of 150 ℃. And washing the solution with methanol for three times, and drying the solution at room temperature to obtain the covalent organic framework @ metal organic framework material. Dissolving 2.1g of polyether amide in 40mL of ethanol solution, stirring for 2h at 80 ℃, adding 0.4g of the covalent organic framework @ metal organic framework material, and stirring for 10h at room temperature to obtain the membrane casting solution. And pouring the casting solution on a Teflon disc, drying for 24 hours at room temperature, and then removing residual solvent in a vacuum drying oven at 45 ℃ for 24 hours to finally obtain the covalent organic framework @ metal organic framework composite membrane.
The covalent organic framework @ metal organic framework composite membrane is used for gas permeation test analysis. By using self-developed equipment to treat mixed gas H2/CO2(30/70 vol%) covalent organic framework @ metal organic framework composite membranes were evaluated at 30 ℃ and a feed pressure of 1bar, N2The sweep gas flow rate was 30mL (STP)/min, and the permeate was analyzed by gas chromatography. According to the result, H2/CO2The selectivity of (A) was 17.6.
Example 3:
first, 24mg of p-benzaldehyde and 40mg of tetrakis (4-aminophenyl) methane were dissolved in 2mL of anhydrous dioxane, and 0.4mL of a 3M aqueous solution of acetic acid was added thereto with vigorous stirring, and the mixture was placed in a high-pressure reactor after being stirred uniformly and reacted at 100 ℃ for 3 days. And washing the obtained product for multiple times by using anhydrous dioxane and anhydrous tetrahydrofuran, and drying the product at room temperature to obtain the covalent organic framework material. 0.4719 g of cobalt acetate and 0.985g of 2-methylimidazole are respectively dissolved in 20mL of methanol, 0.1g of the covalent organic framework material prepared by the method is dissolved in 10mL of methanol, the mixture is ultrasonically dispersed uniformly, and the mixture is placed in a high-pressure reaction kettle to react for 4 hours at the temperature of 120 ℃. And washing the solution with methanol for three times, and drying the solution at room temperature to obtain the covalent organic framework @ metal organic framework material. Dissolving 2.1g of polyether amide in 40mL of ethanol solution, stirring for 2h at 80 ℃, adding 0.4g of the covalent organic framework @ metal organic framework material, and stirring for 10h at room temperature to obtain the membrane casting solution. And pouring the casting solution on a Teflon disc, drying for 24 hours at room temperature, and then removing residual solvent in a vacuum drying oven at 45 ℃ for 24 hours to finally obtain the covalent organic framework @ metal organic framework composite membrane.
The covalent organic framework @ metal organic framework composite membrane is used for gas permeation test analysis. By using self-developed equipment to treat mixed gas H2/CO2(30/70 vol%) covalent organic framework @ metal organic framework composite membranes were evaluated at 30 ℃ and a feed pressure of 1bar, N2The sweep gas flow rate was 30mL (STP)/min, and the permeate was analyzed by gas chromatography. According to the result, H2/CO2The selectivity of (A) was 11.3.
Example 4:
first, 24mg of p-benzaldehyde and 40mg of tetrakis (4-aminophenyl) methane were dissolved in 2mL of anhydrous dioxane, and 0.4mL of a 3M aqueous solution of acetic acid was added thereto with vigorous stirring, and the mixture was placed in a high-pressure reactor after being stirred uniformly and reacted at 100 ℃ for 3 days. And washing the obtained product for multiple times by using anhydrous dioxane and anhydrous tetrahydrofuran, and drying the product at room temperature to obtain the covalent organic framework material. 0.966 g of copper nitrate and 0.84g of trimesic acid are respectively dissolved in 20mL of methanol solvent, 0.1g of the covalent organic framework material prepared by the method is dissolved in 10mL of methanol solvent, the covalent organic framework material is uniformly dispersed by ultrasonic after mixing, and the covalent organic framework material is placed in a high-pressure reaction kettle to react for 10 hours at the temperature of 100 ℃. And washing the solution with methanol for three times, and drying the solution at room temperature to obtain the covalent organic framework @ metal organic framework material. Dissolving 2.1g of polyether amide in 40mL of ethanol solution, stirring for 2h at 80 ℃, adding 0.4g of the covalent organic framework @ metal organic framework material, and stirring for 10h at room temperature to obtain the membrane casting solution. And pouring the casting solution on a Teflon disc, drying for 24 hours at room temperature, and then removing residual solvent in a vacuum drying oven at 45 ℃ for 24 hours to finally obtain the covalent organic framework @ metal organic framework composite membrane.
The covalent organic framework @ metal organic framework composite membrane is used for gas permeation test analysis. By using self-developed equipment to treat mixed gas H2/CO2(30/70 vol%) covalent organic framework @ metal organic framework composite membranes were evaluated at 30 ℃ and a feed pressure of 1bar, N2The scavenging flow was 30mL (STP)/min,the permeate gas composition was analyzed by gas chromatography. According to the result, H2/CO2The selectivity of (a) was 18.2.
Claims (7)
1. A covalent organic framework @ metal organic framework composite membrane is characterized in that: the covalent organic framework @ metal organic framework composite membrane is prepared by the following method:
(1) dissolving p-benzaldehyde and tetra (4-aminophenyl) methane in anhydrous dioxane to obtain a mixed solution A, adding an acetic acid aqueous solution with the concentration of 3-6 mol/L into the mixed solution A while violently stirring, uniformly stirring, placing into a high-pressure reaction kettle, reacting for 24-72 hours at 100-210 ℃, and after the reaction is completed, washing and drying the obtained reactant A to obtain a covalent organic framework material; the mass ratio of the p-benzaldehyde to the tetra (4-aminophenyl) methane is 0.4-0.8: 1, the volume consumption of the anhydrous dioxane is 70-90 mL/g based on the mass of the p-benzaldehyde; the addition amount of the acetic acid aqueous solution is 15-30 mL/g based on the mass of the p-benzaldehyde in the mixed solution A;
(2) dissolving metal salt, ligand and the covalent organic framework material obtained in the step (1) in a solvent, mixing, performing ultrasonic dispersion uniformly to obtain a mixed solution B, placing the mixed solution B in a high-pressure reaction kettle, reacting for 4-24 hours at 100-210 ℃, washing and drying a reactant B after complete reaction to obtain a covalent organic framework @ metal organic framework material; the ligand is 2-methylimidazole or trimesic acid; the mass ratio of the metal salt to the ligand to the covalent organic framework material is 2-8: 6.5-35: 1-2; the metal salt is Zn salt, Co salt, Cu salt or Fe salt;
(3) dissolving polyether amide in ethanol to obtain an alcohol solution of polyether amide, stirring for 2-4 h at 60-120 ℃, adding the covalent organic framework @ metal organic framework material obtained in the step (2) into the alcohol solution of polyether amide, stirring for 9-24 h at room temperature to obtain a casting solution, and then casting the casting solution to form a film to obtain a covalent organic framework @ metal organic framework composite film; the adding amount of the ethanol is 10-25 mL/g based on the mass of the polyether amide; the mass ratio of the covalent organic framework @ metal organic framework material to the polyether amide is 1: 2 to 8.
2. The covalent organic framework @ metal organic framework composite membrane of claim 1, wherein: in the step (1), the washing and drying processes are as follows: the obtained reactant A is washed with anhydrous dioxane and anhydrous tetrahydrofuran for multiple times and dried at room temperature to obtain the covalent organic framework material.
3. The covalent organic framework @ metal organic framework composite membrane of claim 1, wherein: in the step (2), the solvent is methanol or N, N-dimethylformamide.
4. The covalent organic framework @ metal organic framework composite membrane of claim 1, wherein: in the step (2), the adding amount of the solvent is 50-100 mL/g based on the mass of the covalent organic framework material.
5. The covalent organic framework @ metal organic framework composite membrane of claim 1, wherein: in the step (2), the washing and drying processes are as follows: and washing the obtained reactant B with methanol for multiple times, and drying at room temperature to obtain the covalent organic framework @ metal organic framework material.
6. The covalent organic framework @ metal organic framework composite membrane of claim 1, wherein: in the step (3), the casting film forming process comprises the following steps: and pouring the casting solution on a Teflon disc, drying for 24 hours at room temperature, and then removing residual solvent in a vacuum drying oven at 45 ℃ for 24 hours to obtain the covalent organic framework @ metal organic framework composite membrane.
7. Application of the covalent organic framework @ metal organic framework composite film as defined in claim 1 in H2/CO2Separation of (4).
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| CN111215148B (en) * | 2020-03-10 | 2022-06-14 | 辽宁大学 | ZIF @ TU-POP composite catalyst and preparation method and application thereof |
| CN111682208A (en) * | 2020-05-21 | 2020-09-18 | 上海大学 | Composite organic frame nano electrode material and preparation method thereof |
| CN112705179B (en) * | 2020-12-16 | 2022-12-09 | 南开大学 | Hierarchical heteroporous covalent organic framework material and preparation method and application thereof |
| CN113828169B (en) * | 2021-10-20 | 2023-10-20 | 苏州清李新材料科技有限公司 | PolyCOFs/bimetal MOFs composite film and preparation method thereof |
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