Ion conducting membrane

Abstract

An anionic polymer conductive membrane includes vinylbenzyl-Rs, vinylbenzyl-Rx, and styrene. In some embodiments, Rs is a tetramethylimidazolium, and Rs is a positively charged amine. In some embodiments, the total weight of the vinylbenzyl-Rs groups is greater than 20% of the total weight of the film.

Description

Cross Reference to Related Applications

[0001] This application is related to and claims priority from U.S. Patent Application Serial No. 18 / 453,011 filed August 21, 2023, entitled “Ionically Conducting Membranes.” The ‘011 application is hereby incorporated by reference in its entirety. TECHNICAL FIELD

[0002] The field of the invention is electrochemistry. These devices, systems, compositions, and membranes can be used in the fields of water and carbon dioxide electrolysis, batteries, power generation using fuel cells, water purification, and carbon dioxide capture systems, among others. BACKGROUND

[0003] Processes for chemical transformations using electrochemical cells have been known for many years. Typically, an electrochemical cell comprises an anode, a cathode, and an electrolyte. Catalysts can be placed in the anode, cathode, and / or electrolyte to promote the desired chemical reactions. During operation, a reactant or a solution containing a reactant is fed into the cell. A voltage is then applied between the anode and the cathode to promote the desired electrochemical reactions. In the case of water electrolysis devices, hydrogen is produced at the cathode and oxygen is produced at the anode.

[0004] For many years, various ionically conductive membranes have been discussed for use in these cells. Some of these ionically conductive membranes have been disclosed in U.S. Patent Nos. 9,012,345; 9,370,773; 9,464,359; 9,481,939; 9,580,824; 9,555,367; 9,815,021; 9,849,450; 9,943,841; 9,945,040; 9,957,624; 9,982,353; 10,023,967; 10,047,446; 10,975,480; 10,147,974; 10,173,169; 10,396,329; 10,428,432; 10,724,142; 10,774,431; and U.S. Patent Application Serial Nos. 15 / 922,883; 16 / 024,827; 16 / 552,952; and 16 / 429,868.

[0005] U.S. Patent Nos. 9,982,353 and 10,724,142 disclose membranes that are particularly suitable for use in anion exchange membrane (AEM) water electrolysis devices. The membranes disclosed in Patent Nos. 9,982,353 and 10,724,142 were tested in a manner in which a 1 M KOH solution flowed in the anode and the cathode.

[0006] Recently, there has been interest in operating AEM water electrolysis units using a "dry cathode" (where KOH solution is supplied to the anode but not to the cathode). Currently, commercially available membranes operate poorly under dry cathode conditions, likely due to insufficient water transport. Summary of the Invention

[0007] The anion-conductive membrane disclosed in this application has higher mechanical strength and improved water transport compared to the membranes disclosed in U.S. Patent Nos. 9,982,353 and 10,724,142.

[0008] In some preferred embodiments, the anion-conducting film comprises a polymer containing vinylbenzyl-R s Vinylbenzyl-R x The reaction products with styrene, among which (a)R s It is a positively charged amine or phosphine; (b) Vinylbenzyl-R x The reaction product includes benzyl-X with at least one of sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidineethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, and N-methyl-1-D-glucosamine, wherein X is a halogen; (c) Vinylbenzyl-R x With vinylbenzyl-R s They are different chemical substances; (d) Vinylbenzyl-R s The total weight is at least 10% of the polymer weight; and / or (e) Vinylbenzyl-R x The total weight is at least 1% of the polymer weight.

[0009] In some preferred embodiments, the anion-conducting film comprises a polymer including vinylbenzyl-R s Vinylbenzyl-R x The reaction products with styrene, wherein: (a) Vinylbenzyl-R s The reaction products include tetramethylimidazolium and benzyl chloride; (b) Vinylbenzyl-R x Including the reaction product of benzyl chloride with at least one of the following compounds: sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidineethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, N-methyl-D-glucosamine; (c) Vinylbenzyl-R s The total weight is at least 20% of the polymer weight; (d) Vinylbenzyl-Rx The total weight is at least 10% of the polymer weight; and / or (e) The total weight of styrene shall be at least 20% of the weight of the polymer.

[0010] In some embodiments, vinylbenzyl-R x The total weight is at least 20% of the polymer weight.

[0011] In some embodiments, the step of preparing the anion-conducting membrane includes exposing the anion-conducting membrane to sodium ethoxide.

[0012] In some embodiments, vinylbenzyl-R x This includes the reaction products of benzyl chloride and N-methyl-D-glucosamine.

[0013] In some embodiments, the anion-conducting membrane comprises vinylbenzyl-R s Vinylbenzyl-R x1 Vinylbenzyl-R x2 The reaction products with styrene also include: (a) Vinylbenzyl-R x1 Including the reaction product of benzyl chloride with at least one of the following compounds: sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidineethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, N-methyl-D-glucosamine; (b) Vinylbenzyl-R x1 Including the reaction products of benzyl chloride and sodium ethoxylate; (c) The polymer contains at least 1% vinylbenzyl-R x1 ; (d) The polymer contains at least 10% vinylbenzyl-R x2 .

[0014] In some embodiments, the molecular weight of the polymer is between 1,000 and 10,000,000 atomic units (AU).

[0015] In some embodiments, the thickness of the anion-conductive film is between 10 and 300 micrometers.

[0016] In some embodiments, the membrane has an area resistivity of 0.1 ohms / cm² or less in a 1 M KOH solution at 60°C.

[0017] In some embodiments, a battery, fuel cell, electrolyzer, water purification system, or CO2 capture system may include the anion-conducting membrane described in this disclosure.

[0018] In some preferred embodiments, vinylbenzyl-R sThe reaction product includes benzyl-X (where X is a halogen) with at least one of the following: 1,2,2,6,6-pentamethylpiperidine, 1,2,2,5,5-pentamethylpyrrolidine, tetramethylimidazolium, triethylamine, tripropylamine, trimethylamine, N-methylpiperidine, 1-ethylpiperidine, piperidine, 1,4'-bipiperidine, 1-methylpyrrolidine, 2,2,6,6-tetramethylpiperidine, pyrrolidine, 1-pyrrolidineethylamine, 2,3,5-trimethylpyridine, 2 4,6-Trimethylpyridine, 2,6-Dimethylpyridine, 2,4-Dimethylpyridine, 2,3,5-Trimethylpyridine, 4-Methyl-2-(1-pyrrolyl)pyridine, 2-Methylpyridine, 3-Methylpyridine, 4-Methylpyridine, Pyridine, 4,4'-Bipyridine, 2,2'-Bipyridine, Tributylamine, N,N-Diisopropylethylamine, Triphenylamine, N,N-Dimethylcyclohexylamine, N,N-Dicyclohexylmethylamine, Triphenyl Phosphorus, 1,2-dimethylindole, indole, 1-methylindole, hexamethylenetetramine, 2,3,5,6-tetramethylpyrazine, 2,3,5-trimethylpyrazine, 2,3-dimethylpyrazine, 3-methylpyridazine, 2-methylpyrazine, 2,3-diethylpyrazine, ethylpyrazine, pyrazine, 1-methylimidazolium, pyrimidine, 4-methylpyrimidine, pyridazine, triazole, 3,5-dimethyl-1,2,4-triazole, 1,2-dimethyl Imidazole, 2,4,5-triphenylimidazole, 1-decyl-2-methylimidazole, 1-(2-hydroxyethyl)imidazole, guanidine, tetramethylguanidine, dipiperidine, dipyridine, ethylenediamine, propylenediamine, N,N,N'-trimethylethylenediamine, ethylenediaminetetraacetic acid, alkyldiamines, other diamines, ethanolamine, triethanolamine, methylethanolamine, dimethylethanolamine, propanolamine, 3-butenylmagnesium, isobutylmagnesium bromide, cyclohexylmagnesium chloride, and amino acids.

[0019] In some preferred embodiments, vinylbenzyl-R s This includes the reaction product of tetramethylimidazolium and benzyl-X, where X is a halogen.

[0020] In some preferred embodiments, the polymer has a molecular weight of 1,000 to 10,000,000 atomic units (AU), preferably 10,000 to 1,000,000 AU, and most preferably 25,000 to 250,000 AU.

[0021] In some preferred embodiments, the polymer composition is in the form of a film. The thickness of the film is preferably 10-300 micrometers.

[0022] In some preferred embodiments, the membrane has an area resistivity of 0.1 ohms / cm² or less in a 1 M KOH solution at 60°C. Attached Figure Description

[0023] Figure 1 It is a nuclear magnetic resonance spectrum.

[0024] Figure 2 It is another nuclear magnetic resonance spectrum. Detailed Implementation

[0025] It should be understood that the process is not limited to the specific methods, procedures, and reagents described herein, as those skilled in the art will recognize that these may vary. It should also be understood that the terminology used herein is for describing particular embodiments only and is not intended to limit the scope of the process. It should also be noted that, as used herein and in the appended claims, the singular forms “a,” “an,” and “the” include plural references unless the context clearly specifies otherwise. Thus, for example, reference to “connector” refers to one or more connectors and their equivalents known to those skilled in the art. Similarly, the phrase “and / or” is used to indicate that one or both of the described conditions may occur, for example, A and / or B includes (A and B) and (A or B).

[0026] Unless otherwise defined, the technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this process pertains. Embodiments of this process, along with their various features and advantageous details, will be described in detail with reference to non-limiting embodiments and / or in the accompanying drawings and in the following description. It should be noted that the features shown in the drawings are not necessarily drawn to scale, and as will be recognized by those skilled in the art, features of one embodiment may be used with other embodiments, even if not explicitly stated herein.

[0027] Any numerical range described herein includes all values ​​from lower to higher values ​​in one-unit increments, provided that there is at least a two-unit interval between any lower and any higher value. For example, if the numerical values ​​for component concentrations or process variables (e.g., dimensions, angles, pressures, times, etc.) are stated as 1 to 98, specifically 20 to 80, more specifically 30 to 70, then it is intended that this specification explicitly list values ​​such as 15 to 85, 22 to 68, 43 to 51, 30 to 32, etc. For values ​​less than one, one unit is considered as 0.0001, 0.001, 0.01, or 0.1, depending on the circumstances. These are merely examples of a particular intent, and all possible combinations of values ​​between the lowest and highest values ​​should be treated similarly.

[0028] Furthermore, a "Definitions" section follows, which explicitly defines certain terms related to this process. Specific methods, apparatus, and materials are described, but any methods and materials similar to or equivalent to those described herein may be used in the practice or testing of this process.

[0029] definition As used herein, the term "polymer electrolyte membrane" refers to both cation exchange membranes, which typically contain a polymer with multiple covalently linked negatively charged groups, and anion exchange membranes, which typically contain a polymer with multiple covalently linked positively charged groups. Typical cation exchange membranes include proton-conducting membranes, such as the perfluorosulfonic acid polymer available under the trade name NAFION® from DuPont, Wilmington, Delaware.

[0030] The term "anion exchange membrane electrolysis device" as used in this article refers to an electrolysis device having an anion-conducting polymer electrolyte membrane that separates the anode and cathode.

[0031] The term “EMIM” used in this article refers to 1-ethyl-3-methylimidazolium cation.

[0032] The term "CV" refers to cyclic voltammetry.

[0033] The term "Millipore water" refers to water with a resistivity of at least 18.2 megohms-cm produced by a Millipore® filtration system.

[0034] As used herein, the term "imidazolium" refers to a positively charged ligand containing an imidazolium group. This includes naked imidazolium or substituted imidazolium. Specifically, it includes the following forms of ligands:

[0035] R1-R5 are each independently selected from hydrogen, halides, straight-chain alkyl, branched alkyl, cyclic alkyl, heteroalkyl, aryl, heteroaryl, alkylaryl, heteroalkylaryl and their polymers, such as the vinyl benzyl copolymers described herein, which are explicitly included.

[0036] As used herein, the term "pyridine" refers to a positively charged ligand containing a pyridine group. This includes bare pyridines or substituted pyridines. Specifically, it includes ligands in the following forms:

[0037] Among them, R6-R 11 Each of the following is independently selected from hydrogen, halides, straight-chain alkyl, branched alkyl, cyclic alkyl, heteroalkyl, aryl, heteroaryl, alkylaryl, heteroalkylaryl and their polymers, such as the vinyl benzyl copolymers described herein, is explicitly included.

[0038] As used in this article, the term "phosphorus" refers to a phosphorus-containing, positively charged ligand. This includes substituted phosphorus. The ligand forms are as follows:

[0039] Where R 12 -R 15Each of the following is independently selected from hydrogen, halides, straight-chain alkyl, branched alkyl, cyclic alkyl, heteroalkyl, aryl, heteroaryl, alkylaryl, heteroalkylaryl and their polymers, such as the vinyl benzyl copolymers described herein, is explicitly included.

[0040] As used herein, the term "positively charged cyclic amine" refers to a positively charged ligand containing a cyclic amine. This specifically includes imidazolium, pyridinium, pyrazolium, pyrrolidineonium, pyrroloinium, pyrimidineonium, piperidinium, indolineonium, triazineonium, and their polymers, such as the vinyl benzyl copolymers described herein.

[0041] As used in this article, the term "simple amine" refers to substances in the following forms: N(R 16 R 17 R 18 ) Where R 16 R 17 and R 18 Each is independently selected from hydrogen, straight-chain alkyl, branched alkyl, cyclic alkyl, heteroalkyl, aryl, heteroaryl, alkylaryl, heteroalkylaryl, but is not a polymer.

[0042] As used in this article, the term "substituted ethylene" refers to monomers in the following forms:

[0043] R1-R4 are each independently selected from hydrogen, halides, straight-chain alkyl, branched alkyl, cyclic alkyl, heteroalkyl, aryl, heteroaryl, alkylaryl, heteroalkylaryl, including polymers.

[0044] The term "TMIM" used in this article refers to tetramethylimidazole.

[0045] The term "water purification system" as used here refers to a device that removes unwanted components from water. In the case of membrane-based devices, the device uses a membrane as a barrier that allows certain substances to pass through while blocking others.

[0046] As used in this article, the term "battery" refers to a device that generates electrical energy through electrochemical reactions between substances stored inside the battery.

[0047] As used in this article, the term "fuel cell" refers to a device that generates electrical energy through an electrochemical reaction between substances supplied to the fuel cell from an external source.

[0048] As used in this article, the term "electrolysis device" refers to an electrochemical device that uses electrical energy to convert substances into constituent substances. Taking a water electrolysis device as an example, this device uses electricity to convert water into hydrogen and oxygen.

[0049] The term "CO2 capture system" as used here refers to a device capable of separating CO2 from a gas or liquid stream.

[0050] Detailed description The examples provided herein are merely illustrative and are not intended to be an exhaustive list of all possible embodiments, applications, or modifications of this electrochemical device. Therefore, various modifications and variations of the methods and systems described herein will be apparent to those skilled in the art without departing from the scope of the invention. Although the invention has been described in conjunction with specific embodiments, it should be understood that the claimed invention should not be unduly limited to these specific embodiments. Indeed, various modifications to the manner in which the invention is practiced will be apparent to those skilled in the art of chemistry or related fields and are intended to fall within the scope of the appended claims.

[0051] Example 1: Preparation of Alternative Membranes The purpose of Example 1 is to provide a variety of alternative membranes that can be used for water and carbon dioxide electrolysis, batteries, fuel cell power generation, and water purification.

[0052] Typically, the membrane synthesis procedure in Example 1 begins with the procedure listed in U.S. Patent No. 9,370,773, but additional steps 5 and 6 are subsequently added.

[0053] Step 1: Prepare inhibitor-free styrene by washing styrene (Sigma Aldrich, Saint Louis, MO) with two equal volumes of 7.5% sodium hydroxide aqueous solution. Then wash the inhibitor-free styrene with four equal volumes of water to ensure neutralization, and then dry with anhydrous magnesium sulfate. Remove the tert-butylcatechol (TBC) inhibitor from vinylbenzyl chloride (VBC) by extraction with 0.5% potassium hydroxide solution until a colorless extract is obtained. Wash the extract with water until neutral, and then dry with anhydrous magnesium sulfate.

[0054] Step 2: Then, the polymer (vinylbenzyl chloride-co-styrene) was synthesized by heating a solution of inhibitor-free styrene (Sigma-Aldrich) (440 g) and vinylbenzyl chloride (Dupont) (360 g) in 2 L of chlorobenzene (Sigma-Aldrich) for 12-18 hours in a water-jacketed reactor at 60-65 °C under a nitrogen atmosphere using AIBN (a,a'-azoisobutyronitrile, Sigma-Aldrich) (8 g) as an initiator. The resulting copolymer was precipitated in ethanol and dried under vacuum.

[0055] Step 3: Dissolve the copolymer sample obtained in Step 2 in 1-methoxy-2-propanol (Sigma Aldrich) to form a solution with a polymer weight content of 27-32%.

[0056] Step 4: Heat the solution from Step 3 to 60°C, add tetramethylimidazole, and continue stirring the solution for 48 hours. Nuclear magnetic resonance (NMR) analysis showed that approximately 40% of the vinylbenzyl chloride (VBC) remained unreacted at this point. Figure 1 The NMR spectrum after step 4 is shown.

[0057] Step 5: Add 5 mL of the solution from Step 4 to a series of 20 mL vials. Add one of the following amines to each vial: triethylamine, tripropylamine, ethanolamine, 3-(dimethylamino)-1-propylamine, hexylamine, 1-methylpiperidine, 1-piperidineethanol, 1-benzylimidazole, 4-(dimethylamino)pyridine, N-methyl-D-glucosamine, or decylamine (all purchased from Sigma-Aldrich). Heat the vials in a shaker water bath to 45°C for 48 hours.

[0058] Step 6: Prepare a second set of vials identical to those in Step 5. Cool the vials to room temperature and add 2.4 mL of 21% sodium ethoxylate (also known as sodium ethoxide) (C2H5ONa) (Sigma Aldrich) ethanol solution to each vial. Also add 2 mL of 21% sodium ethoxylate ethanol solution to the vial containing the solution from Step 4. In each case, place the vial in a shaker water bath for 5–10 minutes. NMR indicates that the amount of unreacted VBC remaining at this point is less than 1%. Figure 2 shows the NMR spectrum after Step 5.

[0059] Step 7: Attempt to directly cast each solution prepared in Steps 5 and 6 onto a polyethylene terephthalate (PET) substrate to prepare a film. The solution thickness on the substrate was controlled using a coating machine with an adjustable doctor blade (MTI Corporation, Richmond, California). The films were then dried in an oven at 60°C for 120–150 minutes. Each resulting film was immersed in 1 molar KOH overnight and then rinsed with deionized water (DI water). At this point, the film thickness was between 40 and 100 micrometers.

[0060] Next, the water permeability of each membrane was measured as follows: Step 8: Install each membrane sheet on the 25cm section of the Dioxide Materials® membrane. 2 The anode and cathode of the electrolysis unit are supported by a polyether ether ketone (PEEK) mesh.

[0061] Step 9: Circulate 1 mole of KOH through the anode of the battery hardware, while simultaneously introducing 1 L / min of dry nitrogen gas into the cathode. Heat the electrolysis device hardware to 60°C and allow it to reach equilibrium.

[0062] Step 10: The gas leaving the electrolysis unit is introduced into a cold trap and cooled with dry ice for 20 minutes. The cold trap is then weighed, and the weight of the water condensed in the trap is calculated as the difference between the initial weight of the flask and the weight with the condensate. The results are listed in Table 1.

[0063]

[0064] The results in Table 1 show that membranes with a water conductivity more than 20% higher than that prepared in Example 1 can be prepared. This provides sufficient additional permeation for the membrane to be used in a water electrolysis device with a dry cathode. In all examples, the addition of sodium ethoxylate in step 6 increased the water conductivity of the membrane compared to similar membranes without step 6.

[0065] The data in Table 1 also revealed an unexpected finding: the membranes in Examples 3, 5, 6, 7, and 8 were too soft to use, but when sodium ethoxide was added to the solution before casting, fairly robust membranes were obtained.

[0066] When the solution from step 6 was left to stand overnight, it gelled. This indicates that the sodium ethoxide solution did not simply react with the unreacted chlorine in the membrane. Instead, sodium ethoxide catalyzed the crosslinking of the membrane in some way. Previously, examples of sodium ethoxide or related compounds catalyzing membrane crosslinking were not known.

[0067] Membranes prepared using the procedures described in Li et al., “Novel anion exchange membranes based on polymerizable imidazolium salts for alkaline fuel cell applications,” *Journal of Materials Chemistry* 21 (2011), pp. 11340-11346; and Lin et al., “Alkaline-stable C2-substituted imidazolium anion exchange membranes,” *Journal of Materials Chemistry* 25 (2013), p. 1858, were also tested. The polymers prepared using these procedures exhibited low mechanical strength.

[0068] Example 2: Changing the concentration The data in Example 1 were obtained under conditions where VBC comprised 43-46% of the total weight of the copolymer prepared in step 2. However, U.S. Patent 9,370,773 indicates that useful polymers can be prepared using copolymers containing 10, 20, 30, 40, 40, 60, 70, 80, or 90% (±5% for each value) of VBC by weight. Similarly, the data in Example 1 were obtained when 58-62% of the VBC in the copolymer was reacted with TMIM in step 4. By varying the reaction time, 1, 5, 10, 20, 30, 40, 50, or 60% (±5% for each value) of VBC can be reacted with TMIM in step 4.

[0069] The results also showed that if 1-methoxy-2-propanol was replaced with dimethylformamide in step 3, at least 70%, at least 80%, at least 90%, or at least 95% (each value ± 5%) of VBC could react with TMIM. The resulting polymer may contain all or at least a portion of styrene by weight, ranging from approximately 10, 20, 30, 40, 50, 60, 70, or 80%; and all or at least a portion of vinylbenzyl-R by weight, ranging from approximately 10, 20, 30, 40, 50, 60, 70, 80, or 90%. s ; and / or all or at least a portion, ranging from approximately 1, 5, 10, 20, 30, 40, 50, 60, 70% by weight, of vinylbenzyl-R x .

[0070] The examples above are merely illustrative and do not constitute an exhaustive list of all possible embodiments, applications, or modifications of this electrochemical device. Therefore, various modifications and variations of the methods and systems described herein will be apparent to those skilled in the art without departing from the scope and spirit of the invention. Although the invention has been described in conjunction with specific embodiments, it should be understood that the claimed invention should not be unduly limited to these specific embodiments. Indeed, various modifications to the manner in which the invention is practiced will be apparent to those skilled in the art of chemistry or related fields and are intended to fall within the scope of the appended claims.

[0071] All publicly available information from the references and publications cited above is explicitly incorporated as a whole, as if each reference and publication were incorporated individually.

[0072] Especially 9,012,345, 9,370,773, 9,464,359, 9,481,939; 9,580,824; 9,555,367; 9,815,021; 9,849,450; 9,943,841; 9,945,040; 9,957,624; 9,982,353; 10,023,967; 10,047,446; 10,975,480; 10,147,974; 10,173,169; 10,396,329; 10,428,432; 10,724,142; 10,774,431 The contents of the patents and applications 15 / 922,883; 16 / 024,827; 16 / 552,952; and 16 / 429,868 are incorporated herein by reference in their entirety.

[0073] Although specific elements, embodiments, and applications of the invention have been shown and described, it should be understood that the invention is not limited thereto, as modifications can be made by those skilled in the art without departing from the scope of this disclosure, especially in light of the foregoing teachings.

Claims

1. An anion-conducting membrane comprising a polymer, the polymer comprising the reaction product of: ethylene benzyl-R s , ethylene benzyl-R x , and styrene, wherein: R is a C1-C20 alkyl group; and the polymer has a weight average molecular weight of 50,000 to 500,000 g / mole.​​​​ (a) the vinylbenzyl-R s including the reaction product of tetramethylimidazolium with benzyl chloride; (b) the vinylbenzyl-R x including the reaction product of benzyl chloride with at least one of the following: sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidine ethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, N-methyl-D-glucamine; (c) the vinylbenzyl-R s is at least 20% of the weight of the polymer; (d) the vinylbenzyl-R x is at least 10% of the weight of the polymer; and (e) the total weight of the styrene is at least 20% of the weight of the polymer.

2. The anion-conducting membrane of claim 1, wherein the total weight of ethyl vinyl benzyl-R x is at least 20% of the weight of the polymer.

3. The anion conductive membrane of claim 1, wherein the preparation step of the anion conductive membrane comprises exposing the anion conductive membrane to sodium ethoxide.

4. The anion-conducting membrane of claim 1, wherein the vinylbenzyl-R x comprises the reaction product of benzyl chloride and N-methyl-D-glucamine.

5. The anion conductive membrane of claim 1, wherein the anion conductive membrane comprises the reaction product of the vinyl benzyl-R s , vinyl benzyl-R x1 , vinyl benzyl-R X2 , and the styrene, further comprising: (a) the vinylbenzyl-R x1 a reaction product comprising benzyl chloride and at least one of the following: sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidine ethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, N-methyl-D-glucamine; (b) the vinylbenzyl-R x1 including the reaction product of benzyl chloride with sodium ethoxide; (c) the polymer comprises at least 1% of the vinylbenzyl-R x1 ; and (d) the polymer comprises at least 10% of the vinylbenzyl-R x2 .

6. The anion conductive membrane of claim 1, wherein the molecular weight of the polymer is between 1000 and 10,000,000 atomic units (A.U.).

7. The anion conductive membrane of claim 1, wherein the thickness of the anion conductive membrane is between 10 and 300 microns.

8. The anion conductive membrane of claim 1, wherein the area specific resistance of the anion conductive membrane is 0.1 ohm / cm2 or less in 1M KOH solution at 60°C.

9. A battery, fuel cell, electrolytic device, water purification system, or carbon dioxide capture system comprising the anion conductive membrane of claim 1.

10. An anion conductive membrane.

11. A method of operating an anion conductive membrane.

12. An electrolytic device comprising an anion conductive membrane.

13. A fuel cell comprising an anion conductive membrane.

14. A water purification system comprising an anion conductive membrane.

15. A carbon dioxide capture system comprising an anion conductive membrane.

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