CN110085912B - Lithium/sodium ion battery electrolyte additive and preparation method thereof - Google Patents
Lithium/sodium ion battery electrolyte additive and preparation method thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- C07C333/14—Dithiocarbamic acids; Derivatives thereof
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
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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
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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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
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/054—Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
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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
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
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- 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
- Y02E60/10—Energy storage using batteries
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Abstract
The invention discloses an electrolyte additive of a lithium/sodium ion battery and a preparation method thereof, and the structural formula of the effective components is
The structure of the invention has the existence of thiocarbonate ions, and the alternate existence of single and double bonds leads pi bonds to be formed in the compound and can generate a complexing effect with nickel ions dissolved out of the anode material, thereby playing a role in protecting the battery and finally improving the cycle performance of the battery.
Description
Technical Field
The invention belongs to the technical field of ternary system electrolyte, and particularly relates to an electrolyte additive of a lithium/sodium ion battery and a preparation method thereof.
Background
Lithium ion batteries, which have been the highest specific energy secondary batteries up to now, are widely used as power sources or power batteries for portable electronic devices, such as: mobile phones, notebook computers, digital cameras and even new energy vehicles. The lithium ion battery mainly comprises a positive electrode, a negative electrode, electrolyte, a diaphragm and other accessories, wherein the research of the positive electrode material is a current focus, and the research of lithium iron phosphate and ternary materials is mainly carried out.
The ternary material has high energy density and a high voltage platform, and has a good application prospect in power batteries at present, so that the research of the ternary material becomes a hot spot. However, the ternary material has its disadvantages, and studies have shown that the ternary material is accompanied by a phenomenon of elution of metal ions during the charge and discharge of the battery, wherein elution of nickel is most significant, and free nickel ions migrate to the surface of the negative electrode to be deposited, which accelerates the decay of the battery capacity. Similarly, in the case of a lithium ion battery or a sodium ion battery, when a transition metal ion is eluted, the battery is damaged to some extent. At present, no better solution exists for the problem in the ternary material.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides an electrolyte additive of a lithium/sodium ion battery.
The invention also aims to provide a preparation method of the electrolyte additive of the lithium/sodium ion battery.
The technical scheme of the invention is as follows:
the lithium/sodium ion battery electrolyte additive is characterized in that: the structural formula of the effective components is
The addition amount of the electrolyte is 0.1-5% of the total mass of the lithium/sodium ion battery electrolyte, wherein M is Li or Na, and R is1Is hydrogen, alkyl with 1-5 carbon atoms, halogenated alkyl with 1-5 carbon atoms, unsaturated alkyl with 1-5 carbon atoms or unsaturated halogenated alkyl with 1-5 carbon atoms, R2Is hydrogen, alkyl with 1-5 carbon atoms, halogenated alkyl with 1-5 carbon atoms, alkyl with 1-5 carbon atoms and double bond, halogenated alkyl with 1-5 carbon atoms, and R1 and R2 can be mutually connected to form a saturated or double bond-containing five-membered ring or six-membered ring.
In a preferred embodiment of the present invention, the active ingredient has the formula
In a preferred embodiment of the invention, it is added in an amount of 0.1 to 1% of the total mass of the lithium/sodium ion battery electrolyte.
The preparation method of the electrolyte additive of the lithium/sodium ion battery comprises the following steps:
(1) nitrogen-containing organic matter, inorganic base and carbon disulfide are mixed according to a molar ratio of 0.8-1.2: adding 0.8-1.2: 0.8-1.2 into the first solvent, stirring and reacting at 10-20 ℃ for 3-5h, then adding 55-65 ℃, removing part of the first solvent, cooling to room temperature to precipitate crystals, filtering and drying the crystals to obtain a crude product;
(2) and (3) putting the crude product into a second solvent, heating to 45-55 ℃ for dissolution, cooling to 0-5 ℃ for crystallization for 20-25h, and filtering and drying to obtain the lithium/sodium ion battery electrolyte additive, wherein the first solvent and the second solvent are different from each other.
In a preferred embodiment of the invention, the nitrogen-containing organic is pyrrolidine, pyrrole or diethylamine.
In a preferred embodiment of the invention, the inorganic base is sodium hydroxide or lithium hydroxide.
In a preferred embodiment of the present invention, the first solvent is at least one of water, methanol and ethanol.
Further preferably, the first solvent is water.
In a preferred embodiment of the present invention, the second solvent is at least one of methanol, ethanol, acetonitrile and dimethyl carbonate.
Further preferably, the second solvent is ethanol.
The invention has the beneficial effects that: the structure of the invention has the existence of thiocarbonate ions, and the alternate existence of single and double bonds leads pi bonds to be formed in the compound and can generate a complexing effect with nickel ions dissolved out of the anode material, thereby playing a role in protecting the battery and finally improving the cycle performance of the battery.
Drawings
FIG. 1 is a drawing of the present inventionNuclear magnetism of the product obtained in example 41And H, spectrum.
FIG. 2 is a comparative graph showing the cycle of the product obtained in example 4 of the present invention applied to a sodium ion battery.
Detailed Description
The technical solution of the present invention will be further illustrated and described below with reference to the accompanying drawings by means of specific embodiments.
Example 1
The reaction formula of this example is as follows:
the method comprises the following specific steps:
a total of 83g of 99% pure lithium hydroxide monohydrate solid was added to the reaction flask, 800mL of water was added thereto and the lithium hydroxide was dissolved with stirring, and the system was cooled to 15 ℃ and a total of 146g of diethylamine was weighed and slowly added to the reaction flask while controlling the temperature not to exceed 20 ℃ and stirred for 1 hour after the addition. Weighing 152g of carbon disulfide in total, dropwise adding the carbon disulfide into a reaction bottle through a constant-pressure dropping funnel, controlling the temperature not to exceed 20 ℃ during the adding period, maintaining the temperature at 20 ℃ after the adding is finished, stirring and reacting for 2.5h, heating the system to 60 ℃, rotationally evaporating to remove 400mL of water, then placing the residual solution at room temperature for natural crystallization for 24h, filtering after 24h to obtain a solid, pumping out the solid, heating the solid to 50 ℃ by using 600mL of absolute ethyl alcohol for dissolution, slowly cooling the solid to 0-5 ℃ after the complete dissolution, naturally crystallizing for 24h, filtering to obtain the solid, pumping out the solid to obtain 281g of a product in total, wherein the yield is 90.5%, and the purity of the product is 99.2% through nuclear magnetism characterization. The nuclear magnetic characterization data of the product prepared in this example are:1H-NMR(C3D6O)，δ4.08ppm(q，4H，CH2)，δ1.20ppm(t，6H，CH3)。
the final product obtained in example 1 was used as an additive in an electrolyte consisting of lithium hexafluorophosphate solids and ethylene carbonate, in comparison with a base electrolyte without the addition of the additive. The anode adopts ternary material NCM811, the cathode adopts metal lithium to assemble the lithium ion battery, and the lithium ion battery is subjected to a charge and discharge performance test of 0.5C, the limit voltage is 2.7-4.5V at room temperature, and finally, the battery cycle performance containing the additive is found to be superior to the basic electrolyte without the additive.
Example 2
The reaction formula of this example is as follows:
the method comprises the following specific steps:
a total of 83g of 99% pure lithium hydroxide monohydrate solid was added to the reaction flask, 800mL of water was added thereto and stirred to dissolve lithium hydroxide, and the system was cooled to 15 ℃ and a total of 142g of pyrrolidine was weighed and slowly added to the reaction flask while controlling the temperature not to exceed 20 ℃ and stirred for 1 hour after the addition. Weighing 152g of carbon disulfide in total, dropwise adding the carbon disulfide into a reaction bottle through a constant-pressure dropping funnel, controlling the temperature not to exceed 20 ℃ during the adding period, maintaining the temperature at 20 ℃ after the adding is finished, stirring and reacting for 2.5h, heating the system to 60 ℃, rotationally evaporating to remove 400mL of water, then placing the residual solution at room temperature for natural crystallization for 24h, filtering after 24h to obtain a solid, pumping out the solid, heating the solid to 50 ℃ by using 600mL of absolute ethyl alcohol for dissolution, slowly cooling the solid to 0-5 ℃ after the complete dissolution, naturally crystallizing for 24h, filtering to obtain the solid, pumping out the solid to obtain 276g of the product in total, wherein the yield is 90.0%, and the purity of the product is 99.6% through nuclear magnetism characterization. The nuclear magnetic characterization data of the product prepared in this example are:1H-NMR(C3D6O)，δ3.8～3.6ppm(q，4H，CH2N)，δ2.0～1.9ppm(q，4H，CH2CH2N)。
example 3
The reaction formula of this example is as follows:
the method comprises the following specific steps:
into a reaction flaskA total of 83g of lithium hydroxide monohydrate solid with the purity of 99% is added, 800mL of water is added to be stirred to dissolve the lithium hydroxide, the system is cooled to 15 ℃, 134g of pyrrole in total is weighed and slowly added into a reaction bottle, the temperature is controlled not to exceed 20 ℃, and stirring is carried out for 1h after the addition is finished. Weighing 152g of carbon disulfide in total, dropwise adding the carbon disulfide into a reaction bottle through a constant-pressure dropping funnel, controlling the temperature not to exceed 20 ℃ during the adding period, maintaining the temperature at 20 ℃ for stirring and reacting for 2.5h after the adding is finished, heating the system to 60 ℃, rotationally evaporating to remove 400mL of water, then placing the residual solution at room temperature for natural crystallization for 24h, filtering after 24h to obtain a solid, pumping out the solid, heating the solid to 50 ℃ for dissolution by using 600mL of absolute ethyl alcohol, slowly cooling the solid to 0-5 ℃ for natural crystallization for 24h after all dissolution is finished, filtering to obtain the solid, pumping out the solid to obtain 264g of the product in total, wherein the yield is 88.5%, and the purity of the product is 99.4% through nuclear magnetism characterization. The nuclear magnetic characterization data of the product prepared in this example are:1H-NMR(C3D6O)，δ5.99ppm(s，2H，H(3)+H(4))，δ8.03ppm(s，2H，H(2)+H(5))。
example 4
The reaction formula of this example is as follows:
the method comprises the following specific steps:
a total of 83g of 96% pure sodium hydroxide solid was added to the reaction flask, 800mL of water was added and stirred to dissolve the sodium hydroxide, the system was cooled to 15 ℃ and a total of 146g of diethylamine was weighed and slowly added to the reaction flask while controlling the temperature not to exceed 20 ℃ and stirred for 1 hour after the addition. Weighing 152g of carbon disulfide in total, dropwise adding the carbon disulfide into a reaction bottle through a constant-pressure dropping funnel, controlling the temperature not to exceed 20 ℃ during the adding period, maintaining the temperature of 20 ℃ after the adding is finished, stirring and reacting for 2.5h, heating the system to 60 ℃, rotationally evaporating to remove 400mL of water, then naturally crystallizing the residual solution at room temperature for 24h, filtering after 24h to obtain a solid, draining the solid, heating to 50 ℃ by using 600mL of absolute ethyl alcohol to dissolve the solidAfter all the components are dissolved, slowly cooling the mixture to 0-5 ℃ for natural crystallization for 24 hours, filtering the mixture to obtain solid, and draining the solid to obtain a product of which the total weight is 321g, wherein the yield is 93.7 percent, and the purity is 99.6 percent through nuclear magnetic characterization. Nuclear magnetism1The result of the H spectrum is shown in figure 1, and the nuclear magnetic characterization data of the product prepared in the example are as follows:1H-NMR(C3D6O)，δ4.08ppm(q，4H，CH2)，δ1.20ppm(t，6H，CH3)。
the end product obtained in example 4 was used as an additive in an electrolyte at a 2% usage level (electrolyte composed of sodium hexafluorophosphate solids and ethylene carbonate) compared to a base electrolyte without the addition of the additive. The anode adopts ternary materials, the cathode adopts metal sodium to assemble the sodium ion battery, and the sodium ion battery is subjected to a charge-discharge performance test of 0.5C, the cut-off voltage at room temperature is 2.7-4.5V, and the result is shown in figure 2, and the cycle capacity retention rate and the coulombic efficiency of the battery containing 2% of the additive are superior to those of the basic electrolyte without the additive.
Example 5
The reaction formula of this example is as follows:
the method comprises the following specific steps:
adding 83g of 96% pure sodium hydroxide solid into a reaction bottle, adding 800mL of water, stirring to dissolve the sodium hydroxide, cooling the system to 15 ℃, weighing 142g of pyrrolidine in total, slowly adding into the reaction bottle, controlling the temperature to be not more than 20 ℃ during the period, and stirring for 1h after the addition is finished. Weighing 152g of carbon disulfide in total, dropwise adding the carbon disulfide into a reaction bottle through a constant-pressure dropping funnel, controlling the temperature not to exceed 20 ℃ during the adding period, maintaining the temperature of 20 ℃ after the adding is finished, stirring and reacting for 2.5h, heating the system to 60 ℃, rotationally evaporating to remove 400mL of water, then placing the residual solution at room temperature for natural crystallization for 24h, filtering after 24h to obtain a solid, pumping the solid, heating the solid to 50 ℃ by using 600mL of absolute ethyl alcohol for dissolution, slowly cooling the solid to 0-5 ℃ for natural crystallization for 24h after all dissolution is finished, and filtering to obtain the solidThe product obtained after drying was 322g in total, the yield was 95.1%, and the purity of the product was 99.5% by nuclear magnetic characterization. The nuclear magnetic characterization data of the product prepared in this example are:1H-NMR(C3D6O)，δ3.8～3.6ppm(q，4H，CH2N)，δ2.0～1.9ppm(q，4H，CH2CH2N)。
example 6
The reaction formula of this example is as follows:
the method comprises the following specific steps:
the solid sodium hydroxide with the purity of 96 percent is added into a reaction bottle for totally 83g, 800mL of water is added for stirring to dissolve the sodium hydroxide, the system is cooled to 15 ℃, 134g of pyrrole in total is weighed and slowly added into the reaction bottle, the temperature is controlled not to exceed 20 ℃ in the period, and the mixture is stirred for 1h after the addition is finished. Weighing 152g of carbon disulfide in total, dropwise adding the carbon disulfide into a reaction bottle through a constant-pressure dropping funnel, controlling the temperature not to exceed 20 ℃ during the adding period, maintaining the temperature at 20 ℃ after the adding is finished, stirring and reacting for 2.5h, heating the system to 60 ℃, rotationally evaporating to remove 400mL of water, then placing the residual solution at room temperature for natural crystallization for 24h, filtering after 24h to obtain a solid, pumping out the solid, heating the solid to 50 ℃ by using 600mL of absolute ethyl alcohol for dissolution, slowly cooling the solid to 0-5 ℃ after the complete dissolution, naturally crystallizing for 24h, filtering to obtain the solid, pumping out the solid to obtain 311g of the product in total, wherein the yield is 94.2%, and the purity of the product is 99.3% through nuclear magnetism characterization. The nuclear magnetic characterization data of the product prepared in this example are:1H-NMR(C3D6O)，δ5.99ppm(s，2H，H(3)+H(4))，δ8.03ppm(s，2H，H(2)+H(5))。
the above description is only a preferred embodiment of the present invention, and therefore should not be taken as limiting the scope of the invention, which is defined by the appended claims.
Claims (9)
1. An additive for lithium ion or sodium ion battery electrolyte, which is characterized in that: the structural formula of the effective components is
The addition amount of the electrolyte is 0.1-5% of the total mass of the lithium/sodium ion battery electrolyte, wherein M is Li or Na, and R is1Is hydrogen, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, unsaturated alkyl having 1 to 5 carbon atoms or unsaturated haloalkyl having 1 to 5 carbon atoms, R2Is hydrogen, alkyl with 1-5 carbon atoms, halogenated alkyl with 1-5 carbon atoms, alkyl with 1-5 carbon atoms and double bond, or halogenated alkyl with 1-5 carbon atoms and double bond, and R1 and R2 are mutually connected to form a saturated or double bond-containing five-membered ring or six-membered ring;
the preparation method comprises the following steps:
(1) nitrogen-containing organic matter, inorganic base and carbon disulfide are mixed according to a molar ratio of 0.8-1.2: 0.8-1.2: 0.8-1.2, adding the mixture into a first solvent, stirring and reacting for 3-5h at the temperature of 10-20 ℃, heating to 55-65 ℃, removing part of the first solvent, cooling to room temperature to precipitate crystals, and filtering and drying the crystals to obtain a crude product;
(2) and (3) putting the crude product into a second solvent, heating to 45-55 ℃ for dissolution, cooling to 0-5 ℃ for crystallization for 20-25h, and filtering and drying to obtain the lithium ion or sodium ion battery electrolyte additive, wherein the first solvent and the second solvent are different from each other.
2. The additive for the electrolyte of a lithium/sodium ion battery according to claim 1, wherein: the structural formula of the effective components is
、
Or
。
3. The additive for the electrolyte of a lithium or sodium ion battery according to claim 1 or 2, wherein: the addition amount of the electrolyte is 0.1-1% of the total mass of the lithium ion or sodium ion battery electrolyte.
4. The additive for the electrolyte of a lithium or sodium ion battery according to claim 1, wherein: the nitrogen-containing organic matter is pyrrolidine, pyrrole or diethylamine.
5. The additive for the electrolyte of a lithium or sodium ion battery according to claim 1, wherein: the inorganic alkali is sodium hydroxide or lithium hydroxide.
6. The additive for the electrolyte of a lithium or sodium ion battery according to claim 1, wherein: the first solvent is at least one of water, methanol and ethanol.
7. The additive for the electrolyte of a lithium or sodium ion battery according to claim 6, wherein: the first solvent is water.
8. The additive for the electrolyte of a lithium or sodium ion battery according to claim 1, wherein: the second solvent is at least one of methanol, ethanol, acetonitrile and dimethyl carbonate.
9. The additive for a lithium or sodium ion battery electrolyte of claim 8 wherein: the second solvent is ethanol.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4281672A (en) * | 1971-05-28 | 1973-11-29 | Diamond Shamrock Corporation | 2-chloroallyl 2,5-dimethyl-1-pyrrolidine-carbodithioate |
| CN108352573A (en) * | 2015-11-13 | 2018-07-31 | 锡安能量公司 | Additive for electrochemical cell |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7803568B2 (en) * | 2005-04-20 | 2010-09-28 | Purdue Research Foundation | Carbodithioate ligands for nanotechnology and biosensing applications |
| US10153510B2 (en) * | 2014-06-23 | 2018-12-11 | University Of Kentucky Research Foundation | Non-aqueous redox flow batteries including 3,7-perfluoroalkylated phenothiazine derivatives |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4281672A (en) * | 1971-05-28 | 1973-11-29 | Diamond Shamrock Corporation | 2-chloroallyl 2,5-dimethyl-1-pyrrolidine-carbodithioate |
| CN108352573A (en) * | 2015-11-13 | 2018-07-31 | 锡安能量公司 | Additive for electrochemical cell |
Non-Patent Citations (1)
| Title |
|---|
| 添加剂氟代乙烯碳酸酯对锂离子电池低温性能影响的机制研究;张忠如等;《电化学》;20130831;第19卷(第4期);第356-361页 * |
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