CN112290068A - Two quaternary ammonium side chain type anion exchange membranes for fuel cell and preparation method thereof - Google Patents
Two quaternary ammonium side chain type anion exchange membranes for fuel cell and preparation method thereof Download PDFInfo
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1025—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon and oxygen, e.g. polyethers, sulfonated polyetheretherketones [S-PEEK], sulfonated polysaccharides, sulfonated celluloses or sulfonated polyesters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1039—Polymeric electrolyte materials halogenated, e.g. sulfonated polyvinylidene fluorides
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
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- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Abstract
The invention provides two quaternary ammonium side chain type anion exchange membranes for a fuel cell and a preparation method thereof, belonging to the fields of polymer chemistry and anion exchange membrane fuel cells. The anion exchange membrane is characterized in that the molar ratio of two grafted quaternary ammonium groups is different: the molar ratio is as follows: a: b (a and b are both integers of 1-9, and a + b = 10); the invention also provides a preparation method of the two quaternary ammonium side chain type anion exchange membranes, which utilizes nucleophilic polycondensation reaction to carry out polymerization and grafts two quaternary ammonium groups to prepare the two quaternary ammonium side chain type anion exchange membranes. The ion conductivity of the two quaternary ammonium side chain type anion exchange membranes can reach 0.142S/cm at the temperature of 80 ℃.
Description
Technical Field
The invention belongs to the field of polymer chemistry and anion exchange membrane fuel cells, and particularly relates to two quaternary ammonium side chain type anion exchange membranes for a fuel cell and a preparation method thereof.
Background
In recent years, in order to pursue rapid economic development, fossil energy has been excessively used, and problems such as energy depletion and environmental pollution have been caused. At present, most of research focuses on the field of proton exchange membrane fuel cells, but because the catalysts of the proton exchange membrane fuel cells need to adopt expensive metals, the popularization and the development of the proton exchange membrane fuel cells are greatly limited. In contrast, the anion exchange membrane fuel cell has the advantages of fast fuel oxidation rate, low liquid alcohol fuel permeability, capability of using non-noble metal catalysts and the like, and has a wide application prospect, so that research on the anion exchange membrane fuel cell is widely concerned by researchers.
The performance of an anion exchange membrane as a core component of an anion exchange membrane fuel cell directly determines the performance of the anion exchange membrane fuel cell. The types of anion exchange membrane materials researched at present are quite various, and polyether sulfone, polyether ketone, polyvinyl alcohol, polyphenyl ether and the like can be used as the anion exchange membrane matrix materials. The anion exchange membrane also has a plurality of advantages, the catalyst with low price can be selected to replace the noble metal catalyst, the use cost of the fuel cell is greatly reduced, the application in a large range can not depend on the existing resource reserves, the popularization and the application in a large area are facilitated, and the anion exchange membrane is undoubtedly a great breakthrough for promoting the rapid development of the fuel cell.
Disclosure of Invention
The invention aims to provide two quaternary ammonium side chain type anion exchange membranes for a fuel cell and a preparation method thereof.
The invention firstly provides two quaternary ammonium side chain type anion exchange membranes for a fuel cell, and the anion exchange membranes are prepared according to different molar ratios of two grafted quaternary ammonium groups:
wherein the molar ratio of two grafted quaternary ammonium groups is as follows: a: b (a and b are both integers of 1-9, and a + b = 10);
the quaternary ammonium group functionalized polyaryletherketone has a structural formula shown in a formula I:
formula I
The invention also provides a preparation method of two quaternary ammonium side chain type anion exchange membranes for the fuel cell, which comprises the following steps:
the method comprises the following steps: dissolving the polymer in tetrachloroethane, adding benzoyl peroxide and N-bromosuccinimido into 80-DEG oil bath, stirring for 5 hours, and discharging in alcohol to obtain light yellow floccule;
step two: dissolving the light yellow floccule obtained in the first step into a solvent to obtain a clear orange solution;
step three: adding TMA and 1-methylpyrrolidine into the solution obtained in the step two, and stirring for 12-24 hours to obtain a dark yellow film forming solution, wherein an anion exchange membrane is prepared according to different molar ratios of two grafted quaternary ammonium groups, and the molar ratio of the two grafted quaternary ammonium groups is as follows: a: b (a and b are both integers of 1-9, and a + b = 10);
step four: and D, performing casting film forming on the film forming solution obtained in the step three by adopting a tape casting method to obtain two quaternary ammonium side chain type anion exchange membranes for the fuel cell.
2. Preferably, the preparation method of the functionalized polyaryletherketone comprises the following steps: under the protection of nitrogen, 0.02 mol of 4, 4' -difluorobenzophenone and 0.02 mol of methylhydroquinone are added into a three-necked bottle, after uniform mixing, a salt forming agent, a water carrying agent and a solvent are added, after refluxing with water at 125-145 ℃ for 3-5 hours, the water carrying agent is discharged, the temperature is raised to 165-170 ℃, and the reaction is continued for 2-3 hours, so that the polyaryletherketone polymer is obtained.
Preferably, the quaternary ammonium groups are 1-methylpyrrolidine and TMA.
Preferably, the monomers are 4, 4' -difluorobenzophenone and methylhydroquinone.
Preferably, the solvent is one of N, N-Dimethylformamide (DMF), N-dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), or Dimethylsulfoxide (DMSO).
Preferably, the water-carrying agent is toluene.
The invention has the advantages of
The invention firstly provides two quaternary ammonium side chain type anion exchange membranes for a fuel cell, and the anion exchange membranes are prepared according to different molar ratios of two grafted quaternary ammonium groups: because two kinds of quaternary ammonium groups on the branched chain can act as the donor of the ion in this anion exchange membrane, can act as the acceptor of ion again, both can accept the ion and can give the ion, the ion is transmitted with the mode of jumping between two kinds of quaternary ammonium groups, forms ion transmission channel, solves the problem that the dehydration leads to the ionic conductivity to descend under the membrane high temperature then, and the experimental result shows: the two quaternary ammonium side chain type anion exchange membranes have ion conductivity of 0.095S/cm-0.142S/cm at 80 ℃, and the thickness of the anion exchange membrane is 23-30 mu m.
The invention also provides a preparation method of the two quaternary ammonium side chain type anion exchange membranes for the fuel cell, which utilizes nucleophilic polycondensation to prepare the quaternary ammonium functionalized polyaryletherketone. The two quaternary ammonium side chain type anion exchange membranes have the advantages of simple preparation process, short production period, low cost and wide commercial prospect, and can be applied to the field of fuel cells.
Drawings
FIG. 1 is a nuclear magnetic spectrum of polymerization and bromination in the process of preparing functionalized polyaryletherketone in example 1 of the present invention.
FIG. 2 is an infrared spectrum of two quaternary ammonium side chain anion exchange membranes prepared in example 1 of the present invention.
Detailed Description
For a further understanding of the invention, preferred embodiments of the invention are described below in conjunction with the examples, but it should be understood that these descriptions are included merely to further illustrate the features and advantages of the invention and are not intended to limit the invention to the claims.
The invention firstly provides two quaternary ammonium side chain type anion exchange membranes for a fuel cell, and the anion exchange membranes are prepared by grafting two quaternary ammonium groups according to different molar ratios:
wherein the mole ratio of grafting two quaternary amine groups is as follows: a: b (a and b are both integers of 1-9, and a + b = 10);
the quaternary ammonium group functionalized polyaryletherketone has a structural formula shown in a formula I:
formula I
The invention also provides a preparation method of two quaternary ammonium side chain type anion exchange membranes for the fuel cell, which comprises the following steps:
the method comprises the following steps: dissolving the polymer in tetrachloroethane, adding benzoyl peroxide and N-bromosuccinimido into 80-DEG oil bath, stirring for 5 hours, and discharging in alcohol to obtain light yellow floccule;
step two: dissolving the light yellow floccule obtained in the first step into a solvent to obtain a clear orange solution;
step three: adding TMA and 1-methylpyrrolidine into the solution obtained in the step two, and stirring for 12-24 hours to obtain a dark yellow film forming solution, wherein an anion exchange membrane is prepared according to different molar ratios of two grafted quaternary ammonium groups, and the molar ratio of the two grafted quaternary ammonium groups is as follows: a: b (a and b are both integers of 1-9, and a + b = 10);
step four: and D, performing casting film forming on the film forming solution obtained in the step three by adopting a tape casting method to obtain two quaternary ammonium side chain type anion exchange membranes for the fuel cell.
The preparation method of the functionalized polyaryletherketone comprises the following steps: under the protection of nitrogen, 0.02 mol of 4, 4' -difluorobenzophenone and 0.02 mol of methylhydroquinone are added into a three-necked bottle, after uniform mixing, a salt forming agent, a water carrying agent and a solvent are added, after refluxing with water at 125-145 ℃ for 3-5 hours, the water carrying agent is discharged, the temperature is raised to 165-170 ℃, and the reaction is continued for 2-3 hours, so that the polyaryletherketone polymer is obtained. The salt forming agent is preferably anhydrous potassium carbonate, the water-carrying agent is preferably toluene, and the solvent is preferably a high boiling point solvent with a boiling point of 150 ℃ or higher, including but not limited to N, N-Dimethylformamide (DMF), N-dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), or Dimethylsulfoxide (DMSO).
The present invention will be described in further detail with reference to examples.
Example 1
(1) Dissolving the polymer in tetrachloroethane, adding benzoyl peroxide and N-bromosuccinimido into 80-DEG oil bath, stirring for 5 hours, and discharging in alcohol to obtain light yellow floccule;
(2) dissolving the light yellow floccule obtained in the step (1) in a solvent to obtain a clear orange solution;
(3) adding TMA and 1-methylpyrrolidine (molar ratio of TMA to 1-methylpyrrolidine is 5: 5) into the solution obtained in the step (2), stirring for 12-24 hours to obtain a deep yellow film forming solution, wherein an anion exchange membrane is prepared according to different molar ratios of two grafted quaternary amine groups, and the molar ratio of the two grafted quaternary amine groups is as follows: a: b (a and b are both integers of 1-9, and a + b = 10);
(4) and (4) performing film extension on the dark yellow film-forming solution obtained in the step (3) to form a film, then placing the film into a thermostat, drying the film for 48 hours at the temperature of 80 ℃, naturally cooling the film to 25 ℃, and removing the film in distilled water to obtain the two quaternary ammonium side chain type anion exchange membranes for the fuel cell.
Soaking the fuel cell in 1M NaOH solution for 24 hours by using two quaternary ammonium side chain type anion exchange membranes, then soaking the fuel cell in ionized water for 24 hours, changing water for washing for many times during the soaking period to wash out residual NaOH on the membrane surface, and soaking the two pretreated quaternary ammonium side chain type anion exchange membranes in deionized water for later use. The ionic conductivity of the two quaternary ammonium side chain type anion exchange membranes is 0.095S/cm and the film thickness is 27 mu m when tested at 80 ℃, the ionic conductivity of the two quaternary ammonium side chain type anion exchange membranes is 0.027S/cm when tested at 30 ℃, and the ionic conductivity is still 0.067S/cm at 80 ℃ after the membranes are soaked in alkali for 400 hours, so that good alkali resistance stability is reflected. The infrared spectra of the two quaternary ammonium side chain type anion exchange membranes obtained in example 1 are shown in fig. 2, and as can be seen from fig. 2, the two quaternary ammonium side chain type anion exchange membranes were successfully synthesized in the example.
Example 2
(1) Dissolving the polymer in tetrachloroethane, adding benzoyl peroxide and N-bromosuccinimido into 80-DEG oil bath, stirring for 5 hours, and discharging in alcohol to obtain light yellow floccule;
(2) dissolving the light yellow floccule obtained in the step (1) in a solvent to obtain a clear orange solution;
(3) adding TMA and 1-methylpyrrolidine (molar ratio of TMA to 1-methylpyrrolidine is 3: 7) into the solution obtained in the step (2), stirring for 12-24 hours to obtain a deep yellow film forming solution, wherein an anion exchange membrane is prepared according to different molar ratios of two grafted quaternary amine groups, and the molar ratio of the two grafted quaternary amine groups is as follows: a: b (a and b are both integers of 1-9, and a + b = 10);
(4) and (4) performing film extension on the dark yellow film-forming solution obtained in the step (3) to form a film, then placing the film into a thermostat, drying the film for 48 hours at the temperature of 80 ℃, naturally cooling the film to 25 ℃, and removing the film in distilled water to obtain the two quaternary ammonium side chain type anion exchange membranes for the fuel cell.
Soaking the fuel cell in 1M NaOH solution for 24 hours by using two quaternary ammonium side chain type anion exchange membranes, then soaking the fuel cell in ionized water for 24 hours, changing water for washing for many times during the soaking period to wash out residual NaOH on the membrane surface, and soaking the two pretreated quaternary ammonium side chain type anion exchange membranes in deionized water for later use. The ionic conductivity of the two quaternary ammonium side chain type anion exchange membranes is 0.123S/cm and the film thickness is 30 mu m when tested at 80 ℃, the ionic conductivity of the two quaternary ammonium side chain type anion exchange membranes is 0.033S/cm when tested at 30 ℃, and the ionic conductivity is still 0.097S/cm at 80 ℃ after the membranes are soaked in alkali for 400 hours, so that good alkali-resistant stability is embodied.
Example 3
(1) Dissolving the polymer in tetrachloroethane, adding benzoyl peroxide and N-bromosuccinimido into 80-DEG oil bath, stirring for 5 hours, and discharging in alcohol to obtain light yellow floccule;
(2) dissolving the light yellow floccule obtained in the step (1) in a solvent to obtain a clear orange solution;
(3) adding TMA and 1-methylpyrrolidine (molar ratio of TMA to 1-methylpyrrolidine is 1: 9) into the solution obtained in the step (2), stirring for 12-24 hours to obtain a deep yellow film forming solution, wherein an anion exchange membrane is prepared according to different molar ratios of two grafted quaternary amine groups, and the molar ratio of the two grafted quaternary amine groups is as follows: a: b (a and b are both integers of 1-9, and a + b = 10);
(4) and (4) performing film extension on the dark yellow film-forming solution obtained in the step (3) to form a film, then placing the film into a thermostat, drying the film for 48 hours at the temperature of 80 ℃, naturally cooling the film to 25 ℃, and removing the film in distilled water to obtain the two quaternary ammonium side chain type anion exchange membranes for the fuel cell.
Soaking the fuel cell in 1M NaOH solution for 24 hours by using two quaternary ammonium side chain type anion exchange membranes, then soaking the fuel cell in ionized water for 24 hours, changing water for washing for many times during the soaking period to wash out residual NaOH on the membrane surface, and soaking the two pretreated quaternary ammonium side chain type anion exchange membranes in deionized water for later use. The ionic conductivity of the two quaternary ammonium side chain type anion exchange membranes is 0.142S/cm and the film thickness is 17 mu m when tested at 80 ℃, the ionic conductivity of the two quaternary ammonium side chain type anion exchange membranes is 0.038S/cm when tested at 30 ℃, and the ionic conductivity is still 0.124S/cm at 80 ℃ after the membranes are soaked in alkali for 400 hours, so that good alkali resistance stability is embodied.
The above description of the embodiments is only for the purpose of assisting understanding of the method of the present invention and the core idea thereof, and it should be noted that those skilled in the art can make several improvements and modifications to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall into the protection scope of the claims of the present invention.
Claims (7)
1. The fuel cell uses two kinds of quaternary ammonium side chain type anion exchange membranes, characterized by that, this anion exchange membrane is prepared according to the different molar ratios of two kinds of quaternary ammonium groups:
wherein the molar ratio of two quaternary ammonium groups is: a: b (a and b are both integers of 1-9, and a + b = 10);
the quaternary ammonium group functionalized polyaryletherketone has a structural formula shown in a formula I:
formula I.
2. The method for preparing two quaternary ammonium side-chain anion exchange membranes for a fuel cell according to claim 1, comprising the following steps:
the method comprises the following steps: dissolving the polymer in tetrachloroethane, adding benzoyl peroxide and N-bromosuccinimido into 80-DEG oil bath, stirring for 5 hours, and discharging in alcohol to obtain light yellow floccule;
step two: dissolving the light yellow floccule obtained in the first step into a solvent to obtain a clear orange solution;
step three: adding TMA and 1-methylpyrrolidine into the solution obtained in the step two, and stirring for 12-24 hours to obtain a dark yellow film forming solution, wherein an anion exchange membrane is prepared according to different molar ratios of two grafted quaternary ammonium groups, and the molar ratio of the two grafted quaternary ammonium groups is as follows: a: b (a and b are both integers of 1-9, and a + b = 10);
step four: and D, performing casting film forming on the film forming solution obtained in the step three by adopting a tape casting method to obtain two quaternary ammonium side chain type anion exchange membranes for the fuel cell.
3. The method for preparing two quaternary ammonium side-chain anion exchange membranes for a fuel cell according to claim 2, wherein the method for preparing the functionalized polyaryletherketone comprises the following steps: under the protection of nitrogen, 0.02 mol of 4, 4' -difluorobenzophenone and 0.02 mol of methylhydroquinone are added into a three-necked bottle, after uniform mixing, a salt forming agent, a water carrying agent and a solvent are added, after refluxing with water at 125-145 ℃ for 3-5 hours, the water carrying agent is discharged, the temperature is raised to 165-170 ℃, and the reaction is continued for 2-3 hours, so that the polyaryletherketone polymer is obtained.
4. The method for preparing two quaternary ammonium side chain type anion exchange membranes for a fuel cell according to claim 3, wherein the quaternary ammonium groups are TMA and 1-methylpyrrolidine.
5. The method of preparing two quaternary ammonium side-chain anion exchange membranes for a fuel cell according to claim 3, wherein the monomers are 4, 4' -difluorobenzophenone and methylhydroquinone.
6. The method of claim 3, wherein the solvent is one of N, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, or dimethylsulfoxide.
7. The method for preparing two quaternary ammonium side chain type anion exchange membranes for a fuel cell according to claim 3, wherein the water-carrying agent is toluene.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113471498A (en) * | 2021-07-07 | 2021-10-01 | 长春工业大学 | Multi-quaternary ammonium side long-chain type polysulfone anion-exchange membrane and preparation method thereof |
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