CN115275353A - Fluorine-containing electrolyte for lithium battery - Google Patents

Fluorine-containing electrolyte for lithium battery Download PDF

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Publication number
CN115275353A
CN115275353A CN202110477949.0A CN202110477949A CN115275353A CN 115275353 A CN115275353 A CN 115275353A CN 202110477949 A CN202110477949 A CN 202110477949A CN 115275353 A CN115275353 A CN 115275353A
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fluorine
electrolyte
percent
containing electrolyte
polyethylene glycol
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唐旭东
刘沛石
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Tianjin University of Science and Technology
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Tianjin University of Science and Technology
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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
    • H01M10/0569—Liquid materials characterised by the solvents
    • 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
    • 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
    • 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
    • H01M10/0568—Liquid materials characterised by the solutes
    • 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
    • H01M10/058—Construction or manufacture
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H01M2300/0028—Organic electrolyte characterised by the solvent
    • 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
    • Y02E60/10—Energy storage using batteries

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  • Chemical & Material Sciences (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Secondary Cells (AREA)

Abstract

The invention discloses a preparation method of fluorine-containing electrolyte, which comprises the following components in percentage by mass: fluorine-containing additive: 1 to 20 percent; lithium salt: 1 to 30 percent; organic solvent: 80 to 99 percent. The preparation of the fluorine-containing additive comprises the following components in a molar ratio: polyethylene glycol: 1; hexafluoropropylene oxide dimer: 2.3; triethylamine: 2.2. the preparation method of the fluorine-containing electrolyte is characterized in that the fluorine-containing polyether electrolyte additive is prepared and prepared into the electrolyte according to a certain proportion. The fluorine-containing electrolyte combines the advantages of fluorine-containing materials and ether compounds, effectively reduces the problem of high viscosity of the lithium battery electrolyte, improves the production efficiency by optimizing the processing technology, has simpler preparation process method and cheap raw materials, successfully reduces the cost by using the electrolytes prepared in different proportions, and simultaneously improves the electrical property of the lithium battery.

Description

Fluorine-containing electrolyte for lithium battery
Technical Field
The invention belongs to the field of chemical materials and battery electrolyte additives, and relates to a fluorine-containing electrolyte additive which can be used as a lithium battery electrolyte additive to improve the electrical property and the safety property of a lithium battery.
Background
At present, the social economy is rapidly developed, the living standard of people is rapidly improved, the energy demand is increased, and the contradiction between energy and supply is further and further. Fossil energy such as petroleum, coal that use in a large number all belong to irreversible consumption resource at present, and use in a large number can destroy living environment, consequently need adjust the energy structure, use renewable green energy and new forms of energy, in order to solve this problem, utilize natural resources, just need a novel energy accumulator such as lithium cell.
After being converted by the electrochemical energy storage device, the new energy can be applied to various portable devices, but the energy density of the current main energy storage system is far lower than that of the traditional energy, and the dominant position of the traditional fossil energy still cannot be affected. Therefore, for a large-scale electrochemical material energy storage circulation system, the equipment is required to have the advantages of higher comprehensive energy density, longer cycle energy storage service life, high safety, low cost and the like. The lithium ion secondary battery has the advantages of higher battery power density, higher working voltage and the like as a secondary battery which is produced and applied most widely in China and in commerce.
When a lithium ion battery is used as a power source, the use temperature is usually higher than 55 ℃, which accelerates the loss of active materials in an electrode and an electrolyte, and forms a thick and unstable SEI film between the electrode and the electrolyte, thereby causing the rapid degradation of the capacity and cycle performance of the battery. The fluorine-containing material has good heat-conducting property, so that the fluorine-containing material is widely applied to the fields of new energy such as lithium batteries, fuel cells, wind energy, nuclear energy and the like. The outermost layer of the fluorine electron orbit has seven electrons, the electronegativity is strong, and the polarity is weak, so that the fluorine element has a strong electron-withdrawing effect, the introduction of the fluorine-containing material into the electrolyte is beneficial to improving the reduction potential of the electrolyte and the surface of the carbon cathode, optimizing the solid electrolyte interface film, improving the compatibility between the electrolyte and the active material, and further stabilizing the electrochemical performance of the electrode. Meanwhile, the flash point of the fluorine-containing compound is generally very high or has no flash point, so that the fluorine-containing compound can be tried to be introduced into an electrolyte system as an additive, the hydrogen content of solvent molecules is reduced, and the flammability is reduced, so that the thermal stability of the electrolyte and the safety of a lithium battery are greatly improved.
The electrolyte additives of the lithium battery are mainly divided into five types, namely, fluoro-carbonic ester, fluoro-alkyl ether, fluoro-phosphazene derivative, fluoro-phosphate ester and fluoro-ether. The fluorine element has strong electron-withdrawing effect, so that the reduction potential of solvent molecules on the surface of the negative electrode is improved, the solid electrolyte interface film is optimized, the compatibility between the electrolyte and the active material is improved, and the electrochemical performance of the electrode is stabilized. Meanwhile, the organic fluoride is an organic solvent with a high flash point or no flash point, and when the organic solvent forms an electrolyte, the hydrogen content of the molecule of the organic solvent is reduced, so that the flammability is reduced, and the safety of the battery is improved. In summary, based on the performance advantages of the fluorine-containing materials, attempts have been made to incorporate them into electrolytes in order to improve the electrolyte electrical properties.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides the preparation method of the fluorine-containing electrolyte, and the fluorine-containing electrolyte prepared by the method has the advantages of good ionic conductivity and lithium ion transference number.
In order to achieve the target effect, the preparation process of the invention is as follows:
1. the fluorine-containing electrolyte comprises a fluorine-containing additive, lithium salt and an organic solvent, and is prepared from the following components in percentage by mass:
fluorine-containing additive: 1 to 20 percent
Lithium salt: 1 to 30 percent
Organic solvent: 80 to 99 percent
2. Selection of lithium salt: the lithium salt is LiBF4、LiBOB、LiPF6、LiTFSI、LiClO4、LiFSI、LiBETI、LiNO3、LiSCN、LiB(CN)4LiDCTA, liTDI, and the like.
3. Selection of fluorine-containing additive: the fluorine-containing additive is perfluoropropionic alcohol ester and is selected from perfluoro (2-propoxy) propionic polyglycol ester prepared in a laboratory.
4. Selection of organic solvent: the organic solvent is one or two of ethylene carbonate, dimethyl carbonate, diethyl carbonate and methyl ethyl carbonate.
5. A preparation method of a fluorine-containing additive comprises the following steps:
(1) Raw materials required by the reaction are hexafluoropropylene oxide dimer, polyethylene glycol, triethylamine, trichlorotrifluoroethane, dichloromethane, 4-dimethylamino pyridine and the like.
(2) The reaction charge ratio is as follows: the feeding molar ratio of the hexafluoropropylene oxide dimer, the polyethylene glycol and the triethylamine is as follows: 2.3: 1: 2.2.
(3) The reaction temperature is 30-60 ℃, and the reaction time is 2-6h.
6. The preparation method of the fluorine-containing electrolyte comprises the following steps: the prepared fluorine-containing additive is mixed with lithium salt and organic solvent according to a certain proportion, so that the fluorine-containing additive, the lithium salt and the organic solvent are completely mixed to form a stable solution.
Detailed Description
The following description is only exemplary of the present invention and is not intended to limit the present invention in any way; those of ordinary skill in the art can readily practice the present invention as described herein; however, those skilled in the art can utilize the above disclosure without departing from the scope of the invention
Equivalent modifications, adaptations and variations of the present invention, as well as other equivalent embodiments thereof, are intended to be included within the scope of the present invention; meanwhile, any equivalent changes, modifications and evolutions made to the above embodiments according to the substantial technology of the present invention are still within the protection scope of the technical solution of the present invention.
The invention is further illustrated by the following specific examples:
the technical scheme of the invention is as follows:
example 1:
the preparation method of the fluorine-containing electrolyte additive comprises the following components in parts by mole:
polyethylene glycol: 1
Triethylamine: 2.2
Hexafluoropropylene oxide dimer: 2.3
The preparation process comprises the following steps:
(1) 10g of polyethylene glycol 200 was stirred with 11.1g of triethylamine, 10ml of dichloromethane and 0.1g of 4-dimethylaminopyridine in a three-necked flask at-5 ℃ for 10 minutes.
(2) 36.52g of hexafluoropropylene oxide dimer and 20ml of trichlorotrifluoroethane were taken in a dry glass bottle, shaken up and slowly added dropwise into a three-neck flask containing the reactants.
(3) Stirring for 2 hours at room temperature, and then heating to 60 ℃ for reaction for 4 hours to obtain the perfluoro (2-propoxy) propionic acid polyethylene glycol ester.
Example 2:
the preparation method of the fluorine-containing electrolyte additive comprises the following components in parts by mole:
polyethylene glycol: 1
Triethylamine: 2.2
Hexafluoropropylene oxide dimer: 2.3
The preparation process comprises the following steps:
(1) 10g of polyethylene glycol 200 was stirred with 11.1g of triethylamine, 10ml of dichloromethane and 0.1g of 4-dimethylaminopyridine in a three-necked flask at-5 ℃ for 10 minutes.
(2) 36.52g of hexafluoropropylene oxide dimer and 20ml of trichlorotrifluoroethane are put into a dry glass bottle, shaken up and slowly dropped into a three-neck flask containing reactants.
(3) Stirring at room temperature for 2 hours, and then heating to 40 ℃ for reaction for 4 hours to obtain the perfluoro (2-propoxy) propionic acid polyethylene glycol ester.
Example 3:
the preparation method of the fluorine-containing electrolyte additive comprises the following components in percentage by mole:
polyethylene glycol: 1
Triethylamine: 2.2
Hexafluoropropylene oxide dimer: 2.3
The preparation process comprises the following steps:
(1) 10g of polyethylene glycol 200 was taken together with 15.2g of potassium carbonate, 10ml of methylene chloride and 0.1g of 4-dimethylaminopyridine in a three-necked flask and stirred at-5 ℃ for 10 minutes.
(2) 36.52g of hexafluoropropylene oxide dimer and 20ml of trichlorotrifluoroethane are put into a dry glass bottle, shaken up and slowly dropped into a three-neck flask containing reactants.
(3) Stirring at room temperature for 2 hours, and then heating to 40 ℃ for reaction for 4 hours to obtain the perfluoro (2-propoxy) propionic acid polyethylene glycol ester.
Example 4:
the fluorine-containing electrolyte comprises the following components in percentage by mass:
polyethylene glycol perfluoro (2-propoxy) propionate: 0 percent
Lithium bis (trifluoromethanesulfonyl) imide: 15 percent
Ethylene carbonate: 42.5 percent
Dimethyl carbonate: 42.5 percent
The preparation process comprises the following steps:
(1) 4.25g of ethylene carbonate and 4.25g of dimethyl carbonate were mixed and mechanically stirred for 1 minute to form a stable system in the blended solution, and the blended solution was stored in a clean glass bottle under a sealed condition.
(2) In a vacuum glove box under nitrogen atmosphere, 1.5g of lithium bistrifluoromethanesulfonylimide was put into a glass bottle and placed in a vacuum drying box to be heated under vacuum at 110 ℃ for 12 hours.
(3) And after heating, cooling the fluorine-containing electrolyte to room temperature, and then placing the fluorine-containing electrolyte in a nitrogen glove box for storage.
Example 5:
the fluorine-containing electrolyte comprises the following components in percentage by mass:
polyethylene glycol perfluoro (2-propoxy) propionate: 1 percent
Lithium bis (trifluoromethanesulfonyl) imide: 15 percent
Ethylene carbonate: 42 percent
Dimethyl carbonate: 42 percent
The preparation process comprises the following steps:
(1) 0.1g of polyethylene glycol perfluoro (2-propoxy) propionate was mixed with 4.2g of ethylene carbonate and 4.2g of dimethyl carbonate and mechanically stirred for 1 minute to form a stable system in the blended solution, and the blended solution was hermetically stored in a clean glass bottle.
(2) In a vacuum glove box under nitrogen atmosphere, 1.5g of lithium bistrifluoromethanesulfonylimide was put into a glass bottle and placed in a vacuum drying box to be heated under vacuum at 110 ℃ for 12 hours.
(3) And after heating, cooling the fluorine-containing electrolyte to room temperature, and then placing the fluorine-containing electrolyte in a nitrogen glove box for storage.
Example 6:
the fluorine-containing electrolyte comprises the following components in percentage by mass:
polyethylene glycol perfluoro (2-propoxy) propionate: 3 percent of
Lithium bis (trifluoromethanesulfonyl) imide: 15 percent
Ethylene carbonate: 41 percent
Dimethyl carbonate: 41 percent
The preparation process comprises the following steps:
(1) 0.3g of polyethylene glycol perfluoro (2-propoxy) propionate was mixed with 4.1g of ethylene carbonate and 4.1g of dimethyl carbonate and mechanically stirred for 1 minute to form a stable system in the blended solution, and the blended solution was hermetically stored in a clean glass bottle.
(2) In a vacuum glove box under nitrogen atmosphere, 1.5g of lithium bistrifluoromethanesulfonylimide was put into a glass bottle and placed in a vacuum drying box to be heated under vacuum at 110 ℃ for 12 hours.
(3) And after heating, cooling the fluorine-containing electrolyte to room temperature, and then placing the fluorine-containing electrolyte in a nitrogen glove box for storage.
Example 7:
the fluorine-containing electrolyte comprises the following components in percentage by mass:
polyethylene glycol perfluoro (2-propoxy) propionate: 5 percent of
Lithium bis (trifluoromethanesulfonyl) imide: 15 percent of
Ethylene carbonate: 40 percent of
Dimethyl carbonate: 40 percent of
The preparation process comprises the following steps:
(1) 0.5g of polyethylene glycol perfluoro (2-propoxy) propionate was mixed with 4.0g of ethylene carbonate and 4.0g of dimethyl carbonate and mechanically stirred for 1 minute to form a stable system in the blended solution, and the system was hermetically stored in a clean glass bottle.
(2) In a vacuum glove box under nitrogen atmosphere, 1.5g of lithium bistrifluoromethanesulfonylimide was put into a glass bottle and placed in a vacuum drying box to be heated under vacuum at 110 ℃ for 12 hours.
(3) And after heating, cooling the fluorine-containing electrolyte to room temperature, and then placing the fluorine-containing electrolyte in a nitrogen glove box for storage.
Example 8:
the fluorine-containing electrolyte comprises the following components in percentage by mass:
polyethylene glycol perfluoro (2-propoxy) propionate: 7 percent of
Lithium bis (trifluoromethanesulfonyl) imide: 15 percent
Ethylene carbonate: 39 percent of
Dimethyl carbonate: 39 percent
The preparation process comprises the following steps:
(1) 0.7g of polyethylene glycol perfluoro (2-propoxy) propionate was mixed with 3.9g of ethylene carbonate and 3.9g of dimethyl carbonate and mechanically stirred for 1 minute to form a stable system in the blended solution, and the system was hermetically stored in a clean glass bottle.
(2) In a vacuum glove box under nitrogen atmosphere, 1.5g of lithium bistrifluoromethanesulfonylimide was put into a glass bottle and placed in a vacuum drying box to be heated under vacuum at 110 ℃ for 12 hours.
(3) And after heating, cooling the fluorine-containing electrolyte to room temperature, and then placing the fluorine-containing electrolyte in a nitrogen glove box for storage.
The data measured in examples 1 to 3 are as follows:
Figure BSA0000240722480000071
the data measured in examples 4 to 7 are as follows:
Figure BSA0000240722480000072
according to the data comparison of the examples 1 to 3, the yield is lower than that of potassium carbonate when triethylamine is used as an acid-binding agent, and tests show that the triethylamine is used as the acid-binding agent to obtain a product which is not clean enough and has the solid precipitation. And an increase in the reaction temperature can also increase the yield.
According to the data comparison of examples 4 to 8, as the addition amount of the polyethylene glycol perfluoro (2-propoxy) propionate is increased, the viscosity is gradually reduced, and the ionic conductivity and the lithium ion migration number are increased, but when the addition amount of the polyethylene glycol perfluoro (2-propoxy) propionate reaches 7%, the ionic conductivity and the lithium ion migration number are influenced, and the effect is obviously improved when the addition amount is from 3% to 5%. The result of the comprehensive electrical property test shows that the electrical property can be improved by introducing the perfluoro (2-propoxy) propionic acid polyethylene glycol ester as a fluorine-containing additive into the electrolyte.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the invention in any manner; those of ordinary skill in the art can readily practice the present invention as described herein; however, those skilled in the art should appreciate that they can readily use the disclosed conception and specific embodiments as a basis for designing or modifying other structures for carrying out the same purposes of the present invention; meanwhile, any changes, modifications, and evolutions of the equivalent changes of the above embodiments according to the actual techniques of the present invention are still within the protection scope of the technical solution of the present invention.

Claims (6)

1. A fluorine-containing electrolyte for a lithium battery is characterized in that: fluorine-containing additives, lithium salts and organic solvents are included.
2. The fluorine-containing electrolyte according to claim 1, wherein: the addition proportion is as follows according to the mass fraction:
fluorine-containing additive: 1 to 20 percent
Lithium salt: 1 to 30 percent
Organic solvent: 80 to 99 percent.
3. A fluorine-containing electrolyte according to claim 1, wherein: the lithium salt is LiBF4、LiBOB、LiPF6、LiTFSI、LiClO4、LiFSI、LiBETI、LiNO3、LiSCN、LiB(CN)4LiDCTA, liTDI, and the like.
4. The fluorine-containing electrolyte according to claim 1, wherein: the organic solvent is one or two of ethylene carbonate, dimethyl carbonate, diethyl carbonate and ethyl methyl carbonate.
5. A fluorine-containing electrolyte according to claim 1, wherein: the fluorine-containing additive is perfluoropropionic alcohol ester and is selected from perfluoro (2-propoxy) propionic acid polyethylene glycol ester prepared in a laboratory.
6. The method of claim 1, comprising the steps of:
(1) Raw materials required by the reaction are hexafluoropropylene oxide dimer, polyethylene glycol, triethylamine, trichlorotrifluoroethane, dichloromethane, 4-dimethylamino pyridine and the like.
(2) The reaction charge ratio is as follows: the mole ratio of the hexafluoropropylene oxide dimer, the polyethylene glycol and the triethylamine is as follows: 2.3: 1: 2.2.
(3) The reaction temperature is 30-60 ℃, and the reaction time is 2-6h.
CN202110477949.0A 2021-04-30 2021-04-30 Fluorine-containing electrolyte for lithium battery Pending CN115275353A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116120998A (en) * 2023-04-17 2023-05-16 甘肃华隆芯材料科技有限公司 Flushing composition and photoresist pattern forming method thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116120998A (en) * 2023-04-17 2023-05-16 甘肃华隆芯材料科技有限公司 Flushing composition and photoresist pattern forming method thereof

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