CN102195091A - Ionic liquid electrolyte for lithium secondary battery - Google Patents
Ionic liquid electrolyte for lithium secondary battery Download PDFInfo
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- CN102195091A CN102195091A CN2010101209158A CN201010120915A CN102195091A CN 102195091 A CN102195091 A CN 102195091A CN 2010101209158 A CN2010101209158 A CN 2010101209158A CN 201010120915 A CN201010120915 A CN 201010120915A CN 102195091 A CN102195091 A CN 102195091A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Abstract
The invention provides an ionic liquid electrolyte for a lithium secondary battery, aiming at the potential safety hazard problem caused by the traditional lithium secondary battery. The electrolyte consists of a lithium salt, an ionic liquid and an organic solvent, wherein the ionic liquid comprises (1) amino-acid ester liquid, (2) alkylene or acyl substituted imidazole ionic liquid and (3) other types of ionic liquids. The electrolyte at least contains the first or second ionic liquid. The ionic liquid electrolyte has the advantages of simple preparation method, high safety, low viscosity, high conductivity, stable electrochemical property and the like, and can be widely applied to the lithium secondary batteries in which lithium manganate, lithium cobaltate, lithium iron phosphate and the like are used as the positive materials.
Description
Technical field
The present invention relates to a kind of electrolyte that is used for lithium secondary battery, particularly a kind of il electrolyte that is used for lithium secondary battery.
Background technology
Lithium ion battery occupies dominant position with advantages such as himself light weight, capacity height, life-span are long in the portable power source market of electronic products such as mobile phone, notebook, digital camera.Along with economic growth, people are to the enhancing of computer, mobile phone purchasing power, lithium ion battery, particularly high-performance, and the market demand of the lithium ion battery of high security increases year by year.Along with the continual renovation and the development of technology, the application of lithium-ion-power cell on main equipments such as Aero-Space, electric tool, stand-by power supply, electric bicycle, LEV (Light Electric Vehicle) receives publicity day by day.Particularly along with serious day by day, the old fossil energy approach exhaustion of world energy sources crisis and environmental pollution, the prematurity still of new energy technology.Comply with the demand in " low-carbon (LC) epoch ", lithium ion battery relies on the comprehensive advantage of himself coming into a more huge industrial colony---automobile power cell field.And these equipment requirements batteries possess big capacity, high power conditions.Can lithium-ion-power cell satisfy high safety high power, long-life basic demand, is this technology key in application.
At present, Shang Yong lithium secondary cell electrolyte mainly is the mixed solution of organic carbonate ester solvent and lithium salts.The carbonates material is volatile, flash-point is low, lithium secondary battery at high temperature, overcharge etc. that fail safe can not get guaranteeing when using under the specific condition.In order to satisfy the growth requirement of lithium secondary battery, it is extremely urgent to develop the higher novel electrolyte of fail safe.
Ionic liquid is to be made up of the yin, yang ion fully, the organic substance that is in a liquid state under the uniform temperature, have excellent chemical properties such as non-volatile, nonflammable, that conductivity is high, electrochemical window is wide, can significantly improve the fail safe of battery as the electrolyte use of lithium secondary battery.In various ionic liquids, the amino acid esters ionic liquid not only has the wide characteristic of electrochemical window, and the while can promote the lithium salts dissolving again and dissociate.In addition, according to the difference of the ion liquid amount that adds in the electrolyte, charge-discharge performance, the heat-resisting safety performance that can adjust electrolyte satisfy different requirements.
Summary of the invention
The invention provides a kind of il electrolyte that is used for lithium secondary battery, it is characterized in that: this electrolyte is made up of lithium salts, ionic liquid and organic solvent three parts.The ionic liquid of forming electrolyte comprises three kinds of ionic liquids: (1) amino acid esters ionic liquid; (2) glyoxaline ion liquid of alkylene or acyl substituted; (3) ionic liquid of other kind; At least contain first kind or second kind of ionic liquid in the electrolyte.
The ion liquid structural formula of the first seed amino acid ester class of forming electrolyte can be expressed as: [HACOOR]
+X
-, the synthetic selected amino acid of such ionic liquid is: glycine, D-, L-, the DL-alanine, D-, L-, DL-valine, D-, L-, the DL-leucine, D-, L-, the DL-isoleucine, D-, L-, the DL-phenylalanine, D-, L-, DL-cysteine, D-, L-, the DL-cystine, D-, L-, the DL-threonine, D-, L-, DL-glutamic acid, D-, L-, DL-paddy acyl ammonium, D-, L-, the DL-aspartic acid, D-, L-, the DL-asparagine, D-, L-, the DL-methionine, D-, L-, DL-serine, D-, L-, the DL-proline, D-, L-, DL-tyrosine, D-, L-, the DL-tryptophan, D-, L-, DL-lysine, D-, L-, the DL-arginine, D-, L-, DL-histidine, D-, L-, the DL-ornithine, Beta-alanine, o-, p-, the m-amino-benzene ethylformic acid; Connect alkyl, alkoxyl, alkylene, acyl group that group is hydrogen atom or carbon number 1-6 on the amino nitrogen atom, R is the alkyl of aryl or carbon number 1-4, X
-The expression anion.
Alkylene or acyl group that second kind of glyoxaline ion liquid substituting group forming electrolyte is carbon number 1-6.
The third ionic liquid of forming electrolyte comprises the ionic liquid of piperidines, pyroles, imidazoles, quaternary amines, quaternary phosphonium class, pyridines, guanidine class, sulphur cationic.
Forming three kinds of ion liquid anion is: nitrate anion, tetrafluoroborate, hexafluoro-phosphate radical, two (trifluoromethyl sulphonyl) imines root, two (fluorine sulphonyl) imines root, two oxalic acid borate, asccharin anion.
Lithium salts is one or more in LiBF4, lithium hexafluoro phosphate, two (trifluoromethyl sulphonyl) imines lithium, two (fluorine sulphonyl) imines lithium, di-oxalate lithium borate, lithium perchlorate, hexafluoroarsenate lithium, lithium fluoride, lithium chloride, lithium bromide, the chlorine lithium aluminate in the electrolyte.
Organic solvent is a methyl formate in the electrolyte, methyl acetate, methylchloroformate, ethyl acetate, ethyl propionate, ethyl butyrate, vinyl acetate, propionic acid propylene ester, the ring butyrolactone, bromine ring butyrolactone, methyl benzoate, methyl carbonic acid propylene ester, ethyl carbonate propylene ester, the methyl carbonic acid phenol ester, ethylene carbonate, halogenated ethylene carbonate, propene carbonate, butylene, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, carbonic acid first propyl ester, vinylene carbonate, ethylene sulfite, propylene sulfite, the sulfurous acid butene esters, dimethyl sulfite, sulfurous acid diethyl ester, methyl-sulfoxide, the second methyl sulfoxide, the trifluoropropyl methyl sulfoxide, 1, the 3-N-morpholinopropanesulfonic acid lactone, 1, the 4-butyl sultone, in dioxolanes and the dimethoxy propane one or more.
The mass percent of lithium salts is 5-50% in the electrolyte, and ion liquid mass percent is 0-95%, and the mass percent of organic solvent is 5-90%.
Ionic liquid composite electrolyte of the present invention, have excellent properties such as the preparation method is simple, safe, viscosity is low, conductivity is high, electrochemical properties is stable, can be used for LiMn2O4, cobalt acid lithium or LiFePO4 etc. and make the lithium secondary battery of positive electrode, have high market popularization value.
Description of drawings
Fig. 1 make for embodiment 11, two volume change and the cycle efficieny figures of (trifluoromethyl sulphonyl) imines ion liquid electrolyte in the lithium secondary battery charge-discharge test of 2-dimethyl-3-allyl imidazole.
Fig. 2 make for embodiment 21, volume change and the cycle efficieny figure of composite electrolyte in the lithium secondary battery charge-discharge test of two (trifluoromethyl sulphonyl) the imines ion liquid of 2-dimethyl-3-allyl imidazole and dimethyl carbonate composition.
Two (trifluoromethyl sulphonyl) the imines ion liquid and 1 of the methylalanine methyl esters that Fig. 3 makes for embodiment 3, volume change and the cycle efficieny figure of composite electrolyte in the lithium secondary battery charge-discharge test that two (trifluoromethyl sulphonyl) the imines ion liquid of 2-dimethyl-3-allyl imidazole are formed.
Fig. 4 make for embodiment 41, volume change and the cycle efficieny figure of composite electrolyte in the lithium secondary battery charge-discharge test of two (trifluoromethyl sulphonyl) the imines ion liquid of 2-dimethyl-3-allyl imidazole and two (trifluoromethyl sulphonyl) the imines ion liquid compositions of N-methyl-propyl piperidines.
Specific embodiments
The present invention illustrates with following example, but is not limited to following embodiment, in the scope of described aim, changes and implements to be included within the technical scope of the present invention before and after not breaking away from.
By 1, two (trifluoromethyl sulphonyl) the imines ion liquid of 2-dialkyl group-3-alkylene imidazoles prepare method of electrolyte and are: get 10mL 1, two (trifluoromethyl sulphonyl) imines of 2-dialkyl group-3-alkylene imidazoles, two 0.2-5g (trifluoromethyl sulphonyl) imines lithium, 0.5-1mL vinylene carbonate fully mixes and gets final product.The classical group of this electrolyte becomes: 10mL 1, two (trifluoromethyl sulphonyl) imines of 2-dimethyl-3-allyl imidazole, two (trifluoromethyl sulphonyl) the imines lithiums of 1.15g, 1mL vinylene carbonate.Fig. 1 volume change and the cycle efficieny figure of this typical case's electrolyte when carrying out button-shaped lithium secondary battery charge-discharge test that serve as reasons.The concrete processing method of button cell is: battery case model 2032, and directly be coated on the aluminum foil current collector after positive pole is sized mixing by commercially available LiFePO4 and acetylene black, adhesive PVDF and make, barrier film is Cellgard2325, negative pole is a metal lithium sheet.Adopt LAND charge-discharge test instrument to test under 25 ℃, charge-discharge magnification is 0.1C.Fig. 1 shows that the initial capacity of battery is 116.7mAh/g, is 84.1mAh/g through capacity after 50 charge and discharge cycles, and capability retention is 72.1%, and efficiency for charge-discharge remains on more than 90% substantially.
By 1, two (trifluoromethyl sulphonyl) the imines ion liquid of 2-dialkyl group-3-alkylene imidazoles prepare method of electrolyte and are: get 1-9mL 1, two (trifluoromethyl sulphonyl) imines of 2-dialkyl group 3-alkylene imidazoles, the 1-9mL dimethyl carbonate, two 0.2-5g (trifluoromethyl sulphonyl) imines lithium, 0.5-1mL vinylene carbonate fully mixes and gets final product.The classical group of this electrolyte becomes: 5mL 1, two (trifluoromethyl sulphonyl) imines of 2-dimethyl-3-allyl imidazole, 5mL dimethyl carbonate, two (trifluoromethyl sulphonyl) the imines lithiums of 1.15g, 0.5mL vinylene carbonate.Fig. 2 volume change and the cycle efficieny figure of this typical case's electrolyte when carrying out button-shaped lithium secondary battery charge-discharge test that serve as reasons.Battery processing is identical with embodiment 1 with method of testing.Fig. 2 shows that the initial capacity of battery is 134mAh/g, is 110.9mAh/g through capacity after 50 charge and discharge cycles, and capability retention is 82.8%, and efficiency for charge-discharge remains on more than 90% substantially.
Embodiment 3
By two (trifluoromethyl sulphonyl) imines and 1 of methylalanine methyl esters, the two two kinds of ionic liquids of (trifluoromethyl sulphonyl) imines of 2-dialkyl group-3-alkylene imidazoles prepare method of electrolyte: get two (trifluoromethyl sulphonyl) imines of 1-9mL methylalanine methyl esters, 1-9mL 1, two (trifluoromethyl sulphonyl) imines of 2-dialkyl group 3-alkylene imidazoles, two 0.2-5g (trifluoromethyl sulphonyl) imines lithium, 0.5-1mL vinylene carbonate, fully dissolving mixes and gets final product.Wherein typically consist of: two (trifluoromethyl sulphonyl) imines of 1mL methylalanine methyl esters, 9mL 1, two (trifluoromethyl sulphonyl) imines of 2-dimethyl-3-allyl imidazole, two (trifluoromethyl sulphonyl) the imines lithiums of 1.15g, 1mL vinylene carbonate.Fig. 3 volume change and the cycle efficieny figure of this typical case's electrolyte when carrying out the lithium secondary battery charge-discharge test that serve as reasons.Battery processing is identical with embodiment 1 with method of testing.Fig. 3 shows that the initial capacity of battery is 122.1mAh/g, is 84.3mAh/g through capacity after 50 charge and discharge cycles, and capability retention is 69%, and efficiency for charge-discharge remains on more than 90% substantially.
Embodiment 4
By 1, two (trifluoromethyl sulphonyl) imines of 2-dialkyl group-3-alkylene imidazoles and the two two kinds of ionic liquids of (trifluoromethyl sulphonyl) imines of piperidines prepare method of electrolyte: get 1-9mL 1, two (trifluoromethyl sulphonyl) imines of 2-dialkyl group-3-alkylene imidazoles, two (trifluoromethyl sulphonyl) imines of 1-9mL piperidines, two 0.2-5g (trifluoromethyl sulphonyl) imines lithium, 0.5-1mL vinylene carbonate, fully dissolving mixes and gets final product.Wherein typically consist of: 1mL 1, two (trifluoromethyl sulphonyl) imines of 2-dimethyl-3-allyl imidazole, two (trifluoromethyl sulphonyl) imines of 9mLN-methyl-propyl piperidines, two (trifluoromethyl sulphonyl) the imines lithiums of 1.15g, 1mL vinylene carbonate.Fig. 4 volume change and the cycle efficieny figure of this typical case's electrolyte when carrying out button-shaped lithium secondary battery charge-discharge test that serve as reasons.Battery processing is identical with embodiment 1 with method of testing.Fig. 4 shows that the initial capacity of battery is 133mAh/g, is 81.8mAh/g through capacity after 50 charge and discharge cycles, and capability retention is 61.5%, and discharging efficiency remains at more than 90%.
Claims (8)
1. il electrolyte that is used for lithium secondary battery is characterized in that this electrolyte is made up of lithium salts, ionic liquid and organic solvent, and wherein ionic liquid comprises following three kinds: (1) amino acid esters ionic liquid; (2) glyoxaline ion liquid of alkylene or acyl substituted; (3) ionic liquid of other kind; At least contain first kind or second kind of ionic liquid in the electrolyte.
2. the ion liquid structural formula of amino acid esters according to claim 1 can be expressed as: [HACOOR]
+X
-, the synthetic selected amino acid of this ionic liquid is: glycine, D-, L-, the DL-alanine, D-, L-, DL-valine, D-, L-, the DL-leucine, D-, L-, the DL-isoleucine, D-, L-, the DL-phenylalanine, D-, L-, DL-cysteine, D-, L-, the DL-cystine, D-, L-, the DL-threonine, D-, L-, DL-glutamic acid, D-, L-, DL-paddy acyl ammonium, D-, L-, the DL-aspartic acid, D-, L-, the DL-asparagine, D-, L-, the DL-methionine, D-, L-, DL-serine, D-, L-, the DL-proline, D-, L-, DL-tyrosine, D-, L-, the DL-tryptophan, D-, L-, DL-lysine, D-, L-, the DL-arginine, D-, L-, DL-histidine, D-, L-, the DL-ornithine, Beta-alanine, o-, p-, the m-amino-benzene ethylformic acid; Connect alkyl, alkoxyl, alkylene, acyl group that group is hydrogen atom or carbon number 1-6 on the amino nitrogen atom, R is the alkyl of aryl or carbon number 1-4, X
-The expression anion.
3. alkylene or acyl group that glyoxaline ion liquid substituting group according to claim 1 is carbon number 1-6.
4. the ionic liquid that comprises piperidines, pyroles, imidazoles, quaternary amines, quaternary phosphonium class, pyridines, guanidine class, sulphur cationic according to described the third ionic liquid of claim 1.
5. three kinds of ion liquid anion according to claim 1 are: nitrate anion, tetrafluoroborate, hexafluoro-phosphate radical, two (trifluoromethyl sulphonyl) imines root, two (fluorine sulphonyl) imines root, two oxalic acid borate, asccharin anion.
6. lithium salts according to claim 1 is one or more in LiBF4, lithium hexafluoro phosphate, two (trifluoromethyl sulphonyl) imines lithium, two (fluorine sulphonyl) imines lithium, di-oxalate lithium borate, lithium perchlorate, hexafluoroarsenate lithium, lithium fluoride, lithium chloride, lithium bromide, the chlorine lithium aluminate.
7. organic solvent according to claim 1 is a methyl formate, methyl acetate, methylchloroformate, ethyl acetate, ethyl propionate, ethyl butyrate, vinyl acetate, propionic acid propylene ester, the ring butyrolactone, bromine ring butyrolactone, methyl benzoate, methyl carbonic acid propylene ester, ethyl carbonate propylene ester, the methyl carbonic acid phenol ester, ethylene carbonate, halogenated ethylene carbonate, propene carbonate, butylene, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, carbonic acid first propyl ester, vinylene carbonate, ethylene sulfite, propylene sulfite, the sulfurous acid butene esters, dimethyl sulfite, sulfurous acid diethyl ester, methyl-sulfoxide, the second methyl sulfoxide, the trifluoropropyl methyl sulfoxide, 1, the 3-N-morpholinopropanesulfonic acid lactone, 1, the 4-butyl sultone, in dioxolanes and the dimethoxy propane one or more.
8. according to the described electrolyte of claim 1, wherein the mass percent of lithium salts is 5-50%, and ion liquid mass percent is 0-95%, and the mass percent of organic solvent is 5-90%.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102544636A (en) * | 2012-01-06 | 2012-07-04 | 中国科学院过程工程研究所 | Alkaline ion liquid electrolyte for zinc-air battery |
| US20120251895A1 (en) * | 2011-03-30 | 2012-10-04 | Samsung Electronics Co., Ltd. | Electrolyte for lithium secondary battery and lithium secondary battery including the same |
| CN103346349A (en) * | 2013-06-27 | 2013-10-09 | 宁德新能源科技有限公司 | Lithium ion battery and electrolyte thereof |
| CN103594735A (en) * | 2013-11-29 | 2014-02-19 | 湖南高远电池有限公司 | Preparation method for lithium titanate lithium ion battery |
| CN103682454A (en) * | 2013-11-29 | 2014-03-26 | 中南大学 | Preparation method of lithium ion battery adopting lithium titanate cathode |
| CN104681846A (en) * | 2013-11-29 | 2015-06-03 | 苏州宝时得电动工具有限公司 | Battery and electrolytic solution thereof |
| CN105185602A (en) * | 2015-10-12 | 2015-12-23 | 陕西科技大学 | Ionic liquid electrolyte system used for supercapacitor |
| US9799924B2 (en) | 2013-10-10 | 2017-10-24 | Samsung Electronics Co., Ltd. | Electrolyte solution for secondary lithium battery and secondary lithium battery using the same |
| CN110165298A (en) * | 2018-04-02 | 2019-08-23 | 宁波大学 | A kind of electrolyte |
| CN111224163A (en) * | 2018-11-27 | 2020-06-02 | 财团法人工业技术研究院 | Electrolyte composition and metal ion battery comprising same |
| CN112216871A (en) * | 2019-07-10 | 2021-01-12 | 比亚迪股份有限公司 | Lithium ion battery electrolyte, preparation method thereof, lithium ion battery and battery module |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20120251895A1 (en) * | 2011-03-30 | 2012-10-04 | Samsung Electronics Co., Ltd. | Electrolyte for lithium secondary battery and lithium secondary battery including the same |
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| CN102544636A (en) * | 2012-01-06 | 2012-07-04 | 中国科学院过程工程研究所 | Alkaline ion liquid electrolyte for zinc-air battery |
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| CN103682454A (en) * | 2013-11-29 | 2014-03-26 | 中南大学 | Preparation method of lithium ion battery adopting lithium titanate cathode |
| CN104681846A (en) * | 2013-11-29 | 2015-06-03 | 苏州宝时得电动工具有限公司 | Battery and electrolytic solution thereof |
| CN103682454B (en) * | 2013-11-29 | 2015-11-04 | 中南大学 | A kind of preparation method of lithium ion battery adopting lithium titanate anode |
| CN103594735B (en) * | 2013-11-29 | 2015-11-25 | 湖南高远电池有限公司 | A kind of preparation method of lithium titanate lithium ion battery |
| CN105185602A (en) * | 2015-10-12 | 2015-12-23 | 陕西科技大学 | Ionic liquid electrolyte system used for supercapacitor |
| CN110165298A (en) * | 2018-04-02 | 2019-08-23 | 宁波大学 | A kind of electrolyte |
| CN110165298B (en) * | 2018-04-02 | 2022-04-05 | 宁波大学 | Electrolyte solution |
| CN111224163A (en) * | 2018-11-27 | 2020-06-02 | 财团法人工业技术研究院 | Electrolyte composition and metal ion battery comprising same |
| US11258100B2 (en) | 2018-11-27 | 2022-02-22 | Industrial Technology Research Intitute | Electrolyte composition and metal-ion battery employing the same |
| CN112216871A (en) * | 2019-07-10 | 2021-01-12 | 比亚迪股份有限公司 | Lithium ion battery electrolyte, preparation method thereof, lithium ion battery and battery module |
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Application publication date: 20110921 |