CN115732731A - Water-phase-organic redox flow battery - Google Patents
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- CN115732731A CN115732731A CN202211361575.7A CN202211361575A CN115732731A CN 115732731 A CN115732731 A CN 115732731A CN 202211361575 A CN202211361575 A CN 202211361575A CN 115732731 A CN115732731 A CN 115732731A
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Abstract
The invention provides a water phase-organic redox flow battery, which comprises electrodes, a diaphragm, electrolyte, a pump for conveying the electrolyte, a pipeline, a pile control management system and the like; the electrolyte also comprises a negative active material and a positive active material, wherein the negative active material is a bipyridine-quaternary ammonium salt derivative, and the positive active material is a Tempo-quaternary ammonium salt derivative; the active material in the negative electrode electrolyte is a compound of a formula (1) and/or a formula (2) and/or a formula (3), and the active material in the positive electrode electrolyte is a compound of a formula (4) and/or a formula (5) and/or a formula (6); the solvent in the electrolyte is water, and the diaphragm is an ionic membrane or a porous membrane; compared with the existing Tempo/MV organic flow battery, the battery has the advantages that the water solubility of the active substance is higher, the battery performance is more stable, the structural types of the Tempo and bipyridyl derivatives are effectively expanded, the requirements of the flow battery on the membrane are reduced, and more choices are provided for the organic active substance of the flow battery.
Description
Technical Field
The invention belongs to the technical field of flow batteries, and particularly relates to a water phase-organic redox flow battery.
Background
Redox flow batteries that utilize flowing liquid electrolytes to store energy are receiving increasing attention due to their great potential in fixed energy storage applications, and are currently one of the most promising large-scale energy storage technologies, and have been extensively studied for their advantages of high safety, high efficiency, long cycle life, and the like.
Vanadium flow batteries, in which a number of MW class systems have been implemented, fully demonstrate the availability of flow batteries; however, their further development is limited by the relatively high cost and low energy density; therefore, in recent years, organic redox-active materials have received much attention due to their potential advantages of low cost, chemical tunability, and resource sustainability.
Tempo and viologen derivatives have good redox activity and are two types of substances which are more researched in the field of organic flow batteries, and CN108140864B makes many researches on derivatives and applications of the two types of active substances, and specifically protected structures are bipyridine derivatives substituted by electroneutral groups and derivatives containing Tempo groups.
At present, the water system organic flow battery is in the beginning stage of commercialization, the unified conclusion that the active substance with which structure can better meet the market demand is not formed, and the market urgently needs to present a stable organic electrolyte with good performance to promote the development of the water system organic flow battery, so that more economic, safer and more efficient energy storage means is sought.
According to the invention, the structures of the two types of commonly used active substances are adjusted, so that the derivative with more stable structure, better water solubility and more excellent electrochemical performance is obtained; according to the invention, the bipyridyl and Tempo are connected with the positively charged quaternary ammonium salt group, so that higher water solubility is obtained, the energy density and the power density of the flow battery are effectively improved, and the key performance index of the battery is improved.
Disclosure of Invention
To solve the above problems, the present invention discloses an aqueous-organic redox flow battery.
In order to achieve the purpose, the technical scheme of the invention is as follows:
the invention relates to a water phase-organic redox flow battery, which comprises electrodes, a diaphragm, electrolyte, a pump for conveying the electrolyte, a pipeline and a pile control management system, wherein the diaphragm is arranged on the top of the electrode; the electrolyte comprises a negative electrode active substance and a positive electrode active substance, wherein the negative electrode active substance is an asymmetric bipyridyl-quaternary ammonium salt derivative, and the positive electrode active substance is a Tempo-quaternary ammonium salt derivative.
The asymmetric bipyridyl-quaternary ammonium salt derivative of the negative active material has a structure represented by formula (1) to formula (3):
wherein, the first and the second end of the pipe are connected with each other,
R 1 organic bridging groups such as covalent bonds, aromatic rings, aromatic heterocycles and the like;
R 2 and R 3 Organic bridging groups such as saturated alkyl chains, substituted alkyl chains, heteroatom-containing alkyl chains, substituted heteroatom-containing alkyl chains and the like;
R 4 and R 5 Independently of one another, represents hydrogen, alkyl, alkoxy, haloalkyl, cycloalkyl, aryl, aralkyl, heterocyclyl, halogen, hydroxyl, amino, nitro or cyano;
R 6 is alkyl, hydroxyalkyl, carboxyalkyl, aryl, alkylene ether, alkoxyalkyl, aralkyl, amino, ureoyl, carboxyalkylene;
R 7 and R 9 Organic bridging groups such as saturated alkyl chains, alkyl chains containing substituents, alkyl chains containing heteroatoms, alkyl chains containing substituents and heteroatoms and the like;
R 8 is a covalent bond, C 6 -C 18 Arylene radical, C 3 -C 20 Cycloalkylene or condensed C 3 -C 10 Cycloalkylene radical, said C 6 -C 18 Arylene radical, C 3 -C 20 Cycloalkylene or condensed C 3 -C 10 Cycloalkylene groups may also contain substituents and/or contain heteroatoms;
x represents an inorganic and/or organic anion charged q times negatively;
a and b are independently an integer of 0 to 4;
c is a number having a value of 4/q;
d is a number having a value of 3/q;
e is a number having a value of 6/q;
the positive electrode active material Tempo-quaternary ammonium salt derivative has a structure represented by formula (4) to formula (6):
wherein the content of the first and second substances,
R 11 、R 12 、R 13 is a covalent bond, C 6 -C 18 Arylene radical, C 1 -C 10 Alkylene radical, C 3 -C 20 Cycloalkylene or condensed C 3 -C 10 Cycloalkylene, or the arylene, alkylene, cycloalkylene, or fused cycloalkylene may further contain substituents and/or contain heteroatoms;
x, q, c, d have the meanings given in claim 2.
Further, the negative electrode active material may be
wherein, the first and the second end of the pipe are connected with each other,
x, q, c, d have the meanings defined in claim 2;
m is an integer of 0 to 10;
n is an integer from 2 to 10;
l is an integer from 1 to 10;
further, the negative electrode active material may be
further, the positive electrode active material and the negative electrode active material are respectively directly dissolved or dispersed in a system using water as a solvent in a bulk form, and the system further comprises a supporting electrolyte.
Further, the molar concentration of the active substance is 0.05 mol/L-3.0 mol/L.
Further, the electrolyte is NaCl, KCl, liCl, na 2 SO 4 、K 2 SO 4 、MgCl 2 、MgSO 4 、CaCl 2 、NH 4 Cl、KNO 3 、NaNO 3 、KClO 4 、NaClO 4 The molar concentration of the electrolyte is 0.1-8.0 mol/L.
Further, the q-times negatively charged inorganic and/or organic anions are F-, cl-, br-, SO 4 2 ˉ、HSO 4 ˉ、NO 3 ˉ、S 2 ˉ、HSˉ、HCO 3 ˉ、CO 3 2 -ClO-or a combination of any one or more of them.
Further, the separator includes an ion exchange membrane or an ion conductive porous membrane.
Further, the electrode is a carbon material electrode, the carbon material electrode includes any one or more of carbon felt, carbon paper, carbon cloth, carbon black, activated carbon fiber, activated carbon particles, graphene, graphite felt, and glassy carbon material, and other electrodes known in the art may also be used.
The invention has the beneficial effects that:
according to the invention, the structure of two common active substances, namely Tempo and viologen, is adjusted, so that the derivative with more stable structure, better water solubility and more excellent electrochemical performance is obtained; according to the invention, the bipyridyl and the Tempo are connected with the positively charged quaternary ammonium salt group, so that higher water solubility is obtained, and the energy density and the power density of the flow battery are effectively improved, thereby improving the key performance index of the battery.
Drawings
FIG. 1 is a graph of cyclic voltammetry for an electrolyte prepared in example 5 of the present invention;
FIG. 2 is a charge/discharge test chart of a battery prepared in example 5 of the present invention;
fig. 3 is a structural diagram of the positive electrode active material and the negative electrode active material of the present invention.
Detailed Description
The present invention will be further illustrated with reference to the accompanying drawings and specific embodiments, which are to be understood as merely illustrative of the invention and not as limiting the scope of the invention.
The room temperature in the following examples is 25-30 ℃.
Example 1: synthesizing (3) 1-methyl-1 '- [3- (trimethyl ammonium) propyl ] -4,4' -bipyridine trichloride;
bipyridine (1 eq.,20 g) and methyl iodide (0.95 eq.,17.27 g) were added to acetone and reacted at room temperature for 24 hours, and after the reaction was completed, the yellow precipitate that had precipitated was filtered and dried to obtain (2) 4-pyridine-1 '-methyl-4' -pyridyliodide (30.8 g, yield 85%).
Adding (2) 4-pyridine-1 '-methyl-4' -pyridine iodide (1 eq, 20 g) and (3-bromopropyl) trimethyl ammonium bromide (1.1 eq, 19.26 g) into DMF (200 mL), heating to 95 ℃ under the protection of nitrogen for 24 hours for reaction, cooling the reaction liquid to room temperature after the reaction is finished, filtering an orange yellow precipitate, and washing with diethyl ether; the resulting product was exchanged with chloride ion to give (3) 1-methyl-1 '- [3- (trimethylammonium) propyl ] -4,4' -bipyridine trichloride (20.33 g, yield 80%).
Example 2: synthesizing (5) 1-propanol-1 '- [3- (trimethyl ammonium) propyl ] -4,4' -dipyridine trichloride;
bipyridine (1 eq.,20 g) and 3-chloro-1-propanol (1 eq.,17.8 g) were added to acetonitrile (200 mL), and the mixture was refluxed and stirred for 24 hours, and after the reaction was completed, the reaction solution was cooled to room temperature, and filtered to obtain the product (4), 1- (2-hydroxyethyl) - [4,4' -bipyridine ] bromide (30.2 g, yield 83.9%).
Adding (4) 1- (2-hydroxyethyl) - [4,4' -bipyridine ] bromide (1 eq, 20 g) and (3-bromopropyl) trimethyl ammonium bromide (1.1 eq, 20.43 g) into DMF (200 mL), heating to 95 ℃ under the protection of nitrogen for 24 hours for reaction, cooling the reaction liquid to room temperature after the reaction is finished, filtering the product, and washing the product with diethyl ether; the resulting product was exchanged with chloride ion to give (5) 1-propanol-1 '- [3- (trimethylammonium) propyl ] -4,4' -bipyridine trichloride (25.33 g, yield 84.4%).
Example 3: synthesis of (7) 2,2 '-bis (1- (3- (trimethylammonio) propyl) - [4,4' -bipyridine ] -diethyl ether hexachloride;
bipyridine (1 eq.,20 g) and (3-bromopropyl) trimethylammonium bromide (1 eq.,33.42 g) were added to DMF (200 mL), heated to 95 ℃ under nitrogen protection for 24 hours, and after the reaction was completed, the reaction liquid was cooled to room temperature, and the product was filtered and washed with diethyl ether to obtain (6) 1- [3- (trimethylammonium) propyl ] -4,4' -bipyridine bromide (36.37 g, yield 84.21%).
Adding (6) 1- [3- (trimethylammonium) propyl ] -4,4 '-bipyridine bromide (2 eq, 20 g) and 2,2' -dibromodiethyl ether (1.1 eq, 7.57 g) into MeCN (200 mL), refluxing and reacting for 24 hours under the protection of nitrogen, cooling the reaction solution to room temperature after the reaction is finished, filtering the product and washing the product with diethyl ether; the resulting product was exchanged with chloride ion to give (7) 2,2 '-bis (1- (3- (trimethylammonio) propyl) - [4,4' -bipyridine ] -diethyl ether hexachloride (19.13 g, yield 80.68%).
Example 4: synthesizing (7) Tempo-4- [3- (trimethylammonium) propoxy ] salt; 4- [3- (trimethylammonium) propoxy ] -2, 6-tetramethylpiperidin-1-yloxy
To toluene (400 mL) were added Tempo (1 eq.,20 g), 1-bromo-3-chloropropane (1.2 eq.,21.94 g), tetrabutylammonium bromide (1 eq.,37.43 g), and an aqueous sodium hydroxide solution (11.6 g, 40%), followed by reaction at room temperature for 48 hours, washing the reaction mixture with water after the reaction was completed, drying the organic layer over anhydrous sodium sulfate, and distilling off the solvent under reduced pressure. The column was eluted with hexane/ether (7.
Adding (9) 4- [ 3-chloro-propoxy ] -2, 6-tetramethylpiperidine-1-oxyl (1 eq.,20 g) and tetramethylammonium chloride (1.2 eq.,10.57 g) into tetrahydrofuran (200 mL), reacting at room temperature for 48 hours, removing the solvent by distillation under reduced pressure after the reaction is finished, recrystallizing the product twice from ethanol/water (6/1) and drying under vacuum to obtain (10) Tempo-4- [3- (trimethylammonium) propoxy ] salt (20.54 g, yield 83%).
Example 5: synthesizing (11) Tempo-4- [3- (trimethylammonium) propoxy ] salt; 4- [3- (trimethylammonium) propoxy ] -2, 6-tetramethylpiperidin-1-yloxy
Bipyridine (1 eq.,20 g) and 3-chloro-2-hydroxypropyltrimethylammonium chloride (2 eq.,47.94 g) were added to DMF (200 mL), heated to 120 ℃ under nitrogen protection for 24 hours to react, after the reaction was completed, the reaction solution was cooled to room temperature, and the filtered product was washed with a mixture of ethanol and acetone (1).
Example 6: synthesis of (15) N, N, N ', N ' -tetramethyl-N, N ' -bistetra-ethylammonium chloride
4-oxo-2, 6-tetramethylpiperidine-1-oxyl (2 eq.,10 g) and 1, 2-diaminoethane (1.1 eq.,1.94 g) were added to methanol (100 mL), acetic acid (0.4 eq.,0.76 g) was added, and the mixture was reacted at room temperature for 12 hours, and sodium borohydride (0.55 eq.,0.61 g) was added and the reaction was reacted at room temperature for 12 hours. After the reaction was completed, the solvent was spin-dried and recrystallized with water and ethanol, and the intermediate was dried to obtain (13) 4,4' - (ethane-1, 2-diylbis (azepinyl)) bis (2, 6-tetramethylpiperidine-1-oxyl) (10.13 g, yield 93.6%).
The intermediate (13) (1 eq.,6 g) and paraformaldehyde (4 eq.,5.87 g) were added to methanol (60 mL), formic acid (4 eq.,3 g) was added, and the mixture was refluxed for 6 hours. After the reaction, the reaction mixture was cooled to room temperature, extracted with ether and water, the separated aqueous phase was adjusted to pH 12 with aqueous sodium hydroxide (10%), extracted with ether, the organic phase was dried, and the solvent was removed to obtain intermediate (14), N '-dimethyl-N, N' -bistempo ethylenediamine (5.57 g, yield 86.3%).
Intermediate (14) (1 eq, 4 g) was dissolved in acetonitrile (40 mL), iodomethane (10 eq, 14.32 g) was added, the reaction was refluxed for 2h, cooled and the precipitate was filtered, washed with ether, and the solid was ion exchanged to give the chloride product (15) N, N '-tetramethyl-N, N' -bistetrapo ethylammonium chloride (4.62 g, yield 92.3%).
Example 7: synthesis of (16) N- (3-Tempo oxypropyl) -N, N-dimethyl-N-Tempo ammonium chloride
Adding the intermediate (9), 4- [ 3-chloro-propoxy ] -2, 6-tetramethylpiperidine-1-oxyl (1 eq, 5 g) and 4- (N, N-dimethylamino) -2, 6-tetramethylpiperidine-1-oxyl (1.05 eq, 4.21 g) into ethanol (50 mL), refluxing for 5h, after the reaction is finished, spin-drying the solvent, recrystallizing the crude product with ethyl acetate and ethanol, and drying to obtain the product (16), namely N- (3-Tempo oxypropyl) -N, N-dimethyl-N-Tempo ammonium chloride (8.03 g, yield 92%).
Example 8: compound (3)/compound (10) redox flow battery
Adding the compound (3) into water for dissolving, preparing 1mol/L electrolyte, taking 20mL as anolyte, adding the compound (10) into water for dissolving, preparing 1mol/L electrolyte, taking 20mL as catholyte, selecting a carbon felt with the thickness of 4mm, adding a layer of carbon paper, wherein the membrane electrode distance is 3mm, and the effective reaction area is 5cm 2 (ii) a Selecting an anion exchange membrane, and carrying out charge and discharge tests; as shown in fig. 1 and 2, the coulombic efficiency is 99.62%, the energy efficiency is 81.35%, the discharge capacity is about 380mAh, and the charge-discharge cycle is 100 times and is basically stable.
It should be noted that the above-mentioned contents only illustrate the technical idea of the present invention, and the protection scope of the present invention is not limited thereby, and it will be apparent to those skilled in the art that several modifications and embellishments can be made without departing from the principle of the present invention, and these modifications and embellishments fall within the protection scope of the claims of the present invention.
Claims (10)
1. An aqueous-organic redox flow battery is characterized by comprising electrodes, a diaphragm, electrolyte, a pump for conveying the electrolyte, a pipeline and a pile control management system; the electrolyte comprises a negative electrode active substance and a positive electrode active substance, wherein the negative electrode active substance is a bipyridine-quaternary ammonium salt derivative, and the positive electrode active substance is a Tempo-quaternary ammonium salt derivative.
2. An aqueous-organic redox flow battery as claimed in claim 1, wherein the negative active material bipyridyl-quaternary ammonium salt derivative comprises a group represented by formula (1) to formula (3):
wherein R is 1 Organic bridging groups such as covalent bonds, aromatic rings, aromatic heterocycles and the like; r 2 And R 3 Organic bridging groups such as saturated alkyl chains, substituted alkyl chains, heteroatom-containing alkyl chains, substituted heteroatom-containing alkyl chains and the like; r is 4 And R 5 Independently of one another, represents hydrogen, alkyl, alkoxy, haloalkyl, cycloalkyl, aryl, aralkyl, heterocyclyl, halogen, hydroxyl, amino, nitro or cyano; r 6 Is alkyl, hydroxyalkyl, carboxyalkyl, aryl, alkylene ether, alkoxyalkyl, aralkyl, amino, ureoyl, carboxyalkylene; r 7 And R 9 Organic bridging groups such as saturated alkyl chains, alkyl chains containing substituents, alkyl chains containing heteroatoms, alkyl chains containing substituents and heteroatoms and the like; r is 8 Is a covalent bond, C 6 -C 18 Arylene radical, C 3 -C 20 Cycloalkylene or condensed C 3 -C 10 Cycloalkylene radical, said C 6 -C 18 Arylene radical, C 3 -C 20 Cycloalkylene or condensed C 3 -C 10 Cycloalkylene groups may also contain substituents and/or contain heteroatoms; x represents an inorganic or organic anion with q times negative charge(ii) a a and b are independently an integer of 0 to 4; c is a number having a value of 4/q; d is a number having a value of 3/q; e is a number having a value of 6/q.
3. An aqueous-organic redox flow battery as claimed in claim 1, wherein the positive electrode active material Tempo-quaternary ammonium salt derivative comprises the structures of formulae (4) to (6):
wherein R is 11 、R 12 、R 13 Is a covalent bond, C 6 -C 18 Arylene radical, C 1 -C 10 Alkylene radical, C 3 -C 20 Cycloalkylene or condensed C 3 -C 10 Cycloalkylene, the arylene, alkylene, cycloalkylene, or fused cycloalkylene may further contain substituents and/or contain heteroatoms; x, q, c, d have the meaning defined in claim 2.
4. The negative active material bipyridine-quaternary ammonium salt derivative structure according to claim 2, wherein the negative active material comprises:
wherein X, q, c, d have the meaning defined in claim 2; m is an integer of 0 to 10; n is an integer of 2 to 10; l is an integer of 1 to 10.
5. The positive active material Tempo-quaternary ammonium salt derivative structure according to claim 3, wherein the positive active material comprises:
6. An aqueous-organic redox flow battery as claimed in claim 1, wherein the positive and negative active materials are directly dissolved or dispersed in bulk form in a water-based solvent system, and the system further comprises a supporting electrolyte, wherein the supporting electrolyte is NaCl, KCl, liCl, na 2 SO 4 、K 2 SO 4 、MgCl2、MgSO 4 、CaCl 2 、NH 4 Cl、KNO 3 、NaNO 3 The molar concentration of the electrolyte is 0.1-2.0 mol/L.
7. An aqueous-organic redox flow battery as claimed in claim 1, wherein the molar concentration of the active material is 0.05mol/L to 3.0mol/L.
8. An aqueous-organic redox flow battery as claimed in claim 2, wherein the q-times negatively charged inorganic or organic anions are F-, cl-, br-, SO-, or 4 2 ˉ、HSO 4 ˉ、NO 3 ˉ、HCO 3 ˉ、CO 3 2 Any one of them.
9. An aqueous-organic redox flow battery as claimed in claim 1 wherein the membrane comprises an ion exchange membrane and/or an ion conducting porous membrane.
10. An aqueous-organic redox flow battery as claimed in claim 1, wherein the electrode is a carbon material electrode comprising any one or more of carbon felt, carbon paper, carbon cloth, carbon black, activated carbon fiber, activated carbon particle, graphene, graphite felt, glassy carbon material.
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