CN101425610A - Alkylthiophene ionic liquid electrolysis solution used for lithium secondary battery - Google Patents
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Abstract
The invention discloses alkylthiophene ionic liquid electrolyte used for a lithium secondary battery, which is composed of alkylthiophene ionic liquid, lithium salt and organic electrolyte solvent, wherein the chemical structural formula of the alkylthiophene ionic liquid is as follows: the electrolyte composed of the alkylthiophene ionic liquid and the organic electrolyte solvent has the advantages that the production cost is low; the melting point is low, and the electrolyte can be applicable to the low temperature environment; the vapour pressure is very low, the electrolyte can not be volatilized when heated, and electrical chemistry devices can be prevented from being expanded and exploded; the electrolyte is noninflammable, and the security and the stability are high. In charge-discharge test of a button cell, which takes a lithium manganate electrode as the positive electrode, in the alkylthiophene ionic liquid electrolyte composed of butyl thiophene bis (trifluoromethane sulfone imide) imine salt ion liquid, 0.4mol/L lithium bis (trifluoromethane sulfone imide) and vinylene carbonate (the mass ratio of the vinylene carbonate to the ionic liquid is 1:10), the cell initial capacity is 148mAh/g and can still be kept above 110mAh/g after charge-discharge circulations for 50 times.
Description
Technical field
The present invention relates to a kind of electrolyte that is used for lithium secondary battery, particularly a kind of alkylthrophene il electrolyte that is used for lithium secondary battery.
Background technology
Lithium secondary battery since its voltage height, specific energy big, have extended cycle life and good battery performance such as memory-less effect, obtained using widely.Along with the continuous expansion of lithium secondary battery application, its potential safety hazard is also outstanding day by day.Electrolyte is as the important part of battery, and its character directly has influence on the characteristics such as operating current, operating voltage, useful life and fail safe of battery.
At present, business-like lithium secondary battery all adopts the mixed electrolytic solution that organic solvent and salt are formed.The heat-resistant quality of organic solvent and the vapour pressure of solvent, boiling point have great dependence.Generally under high-temperature condition, organic solvent gasification easily makes that its fail safe can not get guaranteeing.If merely utilize high boiling solvent, because of its common viscosity when the room temperature is very high, have in addition be solid, thereby can not fundamentally solve the thermal endurance problem of electrolyte; And under cryogenic conditions, this class electrolyte can be separated out lithium salts, makes the ion concentration that is in dissociated state in the electrolyte significantly descend, and causes normal charge and discharge process to be obstructed or performance degradation.In order to satisfy the needs of electrochemical device development, the electrolyte of development of new is extremely urgent.
When ionic liquid uses as electrolyte, its be solute be again that the characteristics of solvent can overcome above-mentioned deficiency comparatively simply.Patent CN 1123031A and CN1361716A disclose a kind of aromatic series quaternary amines il electrolyte respectively, and it is applied in the lithium battery.But above-mentioned ion liquid cost of material is higher, makes that the ion liquid production cost of this class is also higher.We adopt cheap thiophane to synthesize the alkylthrophene ionic liquid as raw material, the alkylthrophene il electrolyte of being made up of jointly alkylthrophene ionic liquid and organic electrolyte solvent not only possesses good thermal endurance of ionic liquid and anti-flammability, has also reduced production cost than aromatic series quaternary amines il electrolyte.The fusing point of alkylthrophene il electrolyte can be lower than subzero 60 ℃, be lower than the fusing point (about 0 ℃) of aromatic series quaternary amines il electrolyte, according to the difference of the ion liquid amount that adds in the electrolyte, charge-discharge performance, heat-resisting safety and the low-temperature working performance that can adjust electrolyte satisfy different requirements.
Summary of the invention
The object of the invention provides a kind of alkylthrophene il electrolyte that is used for lithium secondary battery.
The present invention is a kind of to be used for alkylthrophene il electrolyte composed as follows of lithium secondary battery:
Form jointly by alkylthrophene ionic liquid, lithium salts and organic electrolyte solvent; Wherein the molar concentration of lithium salts is 0.1mol/L to 1.5mol/L, and the ion liquid mass ratio of organic electrolyte solvent and thiophene is m, 0≤m＜100; Wherein the ion liquid chemical structural formula of alkylthrophene is
R is a kind of in the straight chain aliphatic alkyl of C2～C6 in the formula; A
-Be BF
4 -, PF
6 -Or CF
3SO
2)
2N
-
Lithium salts is tetrafluoro boric acid lithium salts, hexafluorophosphoric acid lithium salts or two (trifluoromethyl sulphonyl) imines lithium salts;
The organic electrolyte solvent 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, 1,3-propane sultone, 1,4-butyl sultone, dioxolanes or dimethoxy propane.
The alkylthrophene ionic liquid is the ethylthiophene tetrafluoroborate, propyl group thiophene tetrafluoroborate, the butyl thiophene tetrafluoroborate, the amylic thiophene tetrafluoroborate, the hexyl thiophene tetrafluoroborate, the ethylthiophene hexafluorophosphate, propyl group thiophene hexafluorophosphate, the butyl thiophene hexafluorophosphate, the amylic thiophene hexafluorophosphate, the hexyl thiophene hexafluorophosphate, ethylthiophene two (trifluoromethyl sulphonyl) inferior amine salt, propyl group thiophene two (trifluoromethyl sulphonyl) inferior amine salt, butyl thiophene two (trifluoromethyl sulphonyl) inferior amine salt, amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt or hexyl thiophene two (trifluoromethyl sulphonyl) inferior amine salt.
The present invention is a kind of, and to be used for the preparation method of alkylthrophene il electrolyte of lithium secondary battery as follows:
(1) the ion liquid preparation of alkylthrophene: thiophane is mixed with mol ratio 1:1 with halogenated alkane, and wherein halogenated alkane is ethane, propane, butane, pentane or the hexane of chloro, bromo or iodo.Add about 30 to 100mL anhydrous acetonitriles after stirring 1 to 5 hour under room temperature, the nitrogen protection, continue to react 7 to 20 days under nitrogen protection, reaction solution is rotary evaporation under 40 to 60 ℃ of water-baths, obtains white or light yellow solid.With absolute ether washing 3 to 5 times and suction filtration, 40 to 60 ℃ of vacuumize two to five days, intermediate product---haloalkyl thiophene.Again with mixed in molar ratio such as haloalkyl thiophene and tetrafluoro boric acid lithium salts, hexafluorophosphoric acid lithium salts or two (trifluoromethyl sulphonyl) imines lithium salts in deionized water, react and use CH after 12 to 24 hours
2Cl
2The extraction separatory keeps non-aqueous solution.Gained solution deionized water wash is up to the not halogen-containing ion of eluate (checking with silver nitrate).With the solution rotating evaporation, 40 to 80 ℃ of following vacuumizes promptly made the alkylthrophene ionic liquid more than 24 hours.
(2) be used for the preparation of the alkylthrophene il electrolyte of lithium secondary battery.Lithium salts, the organic electrolyte solvent of molar concentration 0.1mol/L to 1.5mol/L are mixed with a certain amount of alkylthrophene ionic liquid, and fully dissolving stirs, and obtains a kind of alkylthrophene il electrolyte that is used for lithium secondary battery.
The present invention is a kind of, and to be used for the characteristics of alkylthrophene il electrolyte of lithium secondary battery as follows:
The present invention adopts cheap thiophane to synthesize the alkylthrophene ionic liquid as raw material, ionic liquid and organic electrolyte solvent are used, in fail safe that has improved battery and low-temperature working performance, reduced the production cost of il electrolyte.Compare with the disclosed aromatic series quaternary amines of patent CN 1123031A il electrolyte, the alkylthrophene il electrolyte has reduced production cost when better electrochemical performance (higher conductivity, the electrochemical window of broad and lower viscosity) is provided.Compare with traditional organic electrolyte, alkylthrophene il electrolyte fusing point is lower, goes under the low temperature environment; Its vapour pressure is extremely low, is heated can not volatilize, and can avoid electrochemical device to expand blast; It is nonflammable, can improve the fail safe of electrochemical device greatly.Alkylthrophene ionic liquid fusing point increases with the alkyl carbon atoms number and reduces.For example, the fusing point of ethylthiophene two (trifluoromethyl sulphonyl) inferior amine salt is 66.2 ℃, the fusing point of propyl group thiophene two (trifluoromethyl sulphonyl) inferior amine salt is 24 ℃, and the fusing point of butyl thiophene (and amylic thiophene and hexyl thiophene) two (trifluoromethyl sulphonyl) inferior amine salt then is lower than subzero 60 ℃.The ion liquid viscosity of alkylthrophene is lower, and room-temperature conductivity is higher, and electrochemical window has reached more than the 4V.For example, the viscosity of (25 ℃) butyl thiophene two (trifluoromethyl sulphonyl) inferior amine salt is 80.4mPas under the room temperature, and ionic conductivity is 2.10mS/cm, and electrochemical window is 4.1V.A kind of alkylthrophene il electrolyte of the present invention mainly is to use butyl thiophene ionic liquid, amylic thiophene ionic liquid or hexyl thiophene ionic liquid under normal temperature and low temperature.
A kind of alkylthrophene il electrolyte of the present invention is applicable to the lithium secondary battery of anode material of lithium battery commonly used such as LiMn2O4, cobalt acid lithium or LiFePO4 as positive pole.
Description of drawings
Fig. 1 is that butyl thiophene two (trifluoromethyl sulphonyl) inferior amine salt of embodiment 1 preparation is ion liquid
1The HNMR nuclear magnetic spectrogram
Fig. 2 is the volume change figure of butyl thiophene two (trifluoromethyl sulphonyl) when the inferior amine salt il electrolyte is carried out the lithium secondary battery charge-discharge test of embodiment 1 preparation
Fig. 3 is that amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt of embodiment 2 and 3 preparations is ion liquid
1The HNMR nuclear magnetic spectrogram
Fig. 4 is capacity and the efficiency change figure of amylic thiophene two (trifluoromethyl sulphonyl) when the inferior amine salt il electrolyte is carried out the lithium secondary battery charge-discharge test of embodiment 2 preparations
Fig. 5 is the volume change figure of amylic thiophene two (trifluoromethyl sulphonyl) when the inferior amine salt il electrolyte is carried out the lithium secondary battery charge-discharge test of embodiment 3 preparations
Embodiment
The following examples are to further specify of the present invention, but do not limit the scope of the invention
Embodiment 1: a kind of electrolyte of being made up of butyl thiophene two (trifluoromethyl sulphonyl) imines ion liquid and the application in lithium secondary battery thereof
(1) butyl thiophene two (trifluoromethyl sulphonyl) imines ion liquid is synthetic: thiophane is mixed with mol ratio with butyl halide at 1: 1; after stirring 1 to 5 hour under room temperature, the nitrogen protection, add about 30 to 100mL anhydrous acetonitriles; continuation was reacted under nitrogen protection 7 to 20 days; reaction solution is rotary evaporation under 40 to 60 ℃ of water-baths, obtains light yellow solid.With absolute ether washing 3 to 5 times and suction filtration, 40 to 60 ℃ of vacuumize two to five days, intermediate product---halogenated butyl thiophene.Again halogenated butyl thiophene and two (trifluoromethyl sulphonyl) imines lithium salts equimolar amounts is mixed in the deionized water, reacts and use CH after 12 to 24 hours
2Cl
2The extraction separatory keeps non-aqueous solution.Gained solution deionized water wash is up to the not halogen-containing ion of eluate (checking with silver nitrate).With the solution rotating evaporation, 40 to 80 ℃ of following vacuumizes promptly made butyl thiophene two (trifluoromethyl sulphonyl) imines ion liquid more than 24 hours.Fig. 1 is that butyl thiophene two (trifluoromethyl sulphonyl) inferior amine salt is ion liquid
1H NMR nuclear magnetic spectrogram, nuclear magnetic data is
1H NMR, δ (CD
3COCD
3, ppm): 3.74-3.61 (m, 4H), 3.41-3.37 (t, 2H), 2.47-2.39 (m, 4H), 1.88-1.84 (m, 2H), 1.56-1.50 (m, 2H), (t 3H), illustrates that prepared is pure butyl thiophene two (trifluoromethyl sulphonyl) inferior amine salt ionic liquid to 0.99-0.94.
(2) get 10ml butyl thiophene two (trifluoromethyl sulphonyl) inferior amine salt ionic liquid, add two (trifluoromethyl sulphonyl) imines lithium salts (molar concentration is 0.4mol/L), add again vinylene carbonate (with ion liquid mass ratio be 1:10), fully dissolving mixes, and obtains a kind of butyl thiophene two (trifluoromethyl sulphonyl) imines ion liquid electrolyte that is used for lithium secondary battery.
(3) the volume change figure of butyl thiophene two (trifluoromethyl sulphonyl) when the inferior amine salt il electrolyte is carried out the lithium secondary battery charge-discharge test that make for embodiment 1 of Fig. 2.Make button-shaped lithium secondary battery and test, wherein: battery size is CR2016; LiMn2O4 electrode (the commercialization electrode is directly buied) just very, electrode current collecting body is an aluminium foil; Barrier film is a Whatman GF/A type fibreglass diaphragm; Negative pole is a metal lithium sheet.Adopt LAND charge-discharge test instrument to test under normal temperature (25 ℃), charge-discharge magnification is 0.1C.Fig. 2 has shown that the battery initial capacity is 148mAh/g, is 110mAh/g through capacity after 50 charge and discharge cycles, and capability retention is 74.3%.
Embodiment 2: a kind of electrolyte of being made up of amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt ionic liquid and the application in lithium secondary battery thereof
(1) thiophane is mixed with mol ratio 1:1 with the halo pentane; after stirring 1 to 5 hour under room temperature, the nitrogen protection, add about 30 to 100mL anhydrous acetonitriles; continuation was reacted under nitrogen protection 7 to 20 days, and reaction solution is rotary evaporation under 40 to 60 ℃ of water-baths, obtains white solid.With absolute ether washing 3 to 5 times and suction filtration, 40 to 60 ℃ of vacuumize two to five days, intermediate product---halo amylic thiophene.Again halo amylic thiophene and two (trifluoromethyl sulphonyl) imines lithium salts equimolar amounts is mixed in the deionized water, reacts and use CH after 12 to 24 hours
2Cl
2The extraction separatory keeps non-aqueous solution.Gained solution deionized water wash is up to the not halogen-containing ion of eluate (checking with silver nitrate).With the solution rotating evaporation, 40 to 80 ℃ of following vacuumizes promptly made amylic thiophene two (trifluoromethyl sulphonyl) imines ion liquid more than 24 hours.Fig. 3 is that amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt is ion liquid
1The HNMR nuclear magnetic spectrogram, nuclear magnetic data is
1H NMR, δ (CD
3COCD
3, ppm): 3.73-3.58 (m, 4H), 3.38-3.34 (t, 2H), 2.46-2.36 (m, 4H), 1.89-1.85 (m, 2H), 1.50-1.37 (m, 4H), (t 3H), illustrates that prepared is pure amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt ionic liquid to 0.92-0.88.
(2) get 10ml amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt ionic liquid, add hexafluorophosphoric acid lithium salts (concentration is 0.4mol/L), add again ethylene sulfite (with ion liquid mass ratio be 1: 30), fully dissolving mixes, and obtains a kind of amylic thiophene two (trifluoromethyl sulphonyl) imines ion liquid electrolyte that is used for lithium secondary battery.
(3) capacity and the efficiency change figure of amylic thiophene two (trifluoromethyl sulphonyl) when the inferior amine salt il electrolyte is carried out the lithium secondary battery charge-discharge test that make for embodiment 2 of Fig. 4.Make button-shaped lithium secondary battery and test, wherein: battery size is CR2016; LiMn2O4 electrode (the commercialization electrode is directly buied) just very, electrode current collecting body is an aluminium foil; Barrier film is a Whatman GF/A type fibreglass diaphragm; Negative pole is a metal lithium sheet.Adopt LAND charge-discharge test instrument to test under normal temperature (25 ℃), charge-discharge magnification is 0.1C.Fig. 4 has shown that the battery initial capacity is 70mAh/g, is 40mAh/g through capacity after 50 charge and discharge cycles, and capability retention is 57.1%, and efficiency for charge-discharge remains at more than 95%.
Embodiment 3: a kind of electrolyte of being made up of amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt ionic liquid and the application in lithium secondary battery thereof
(1) thiophane is mixed than 1:1 with amount with the halo pentane; after stirring 1 to 5 hour under room temperature, the nitrogen protection, add about 30 to 100mL anhydrous acetonitriles; continuation was reacted under nitrogen protection 7 to 20 days, and reaction solution is rotary evaporation under 40 to 60 ℃ of water-baths, obtains light yellow solid.With absolute ether washing 3 to 5 times and suction filtration, 40 to 60 ℃ of vacuumize two to five days, intermediate product---halo amylic thiophene.Again halo amylic thiophene and two (trifluoromethyl sulphonyl) imines lithium salts equimolar amounts is mixed in the deionized water, reacts and use CH after 12 to 24 hours
2Cl
2The extraction separatory keeps non-aqueous solution.Gained solution deionized water wash is up to the not halogen-containing ion of eluate (checking with silver nitrate).With the solution rotating evaporation, 40 to 80 ℃ of following vacuumizes promptly made amylic thiophene two (trifluoromethyl sulphonyl) imines ion liquid more than 24 hours.Fig. 3 is that amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt is ion liquid
1H NMR nuclear magnetic spectrogram, nuclear magnetic data is
1H NMR, δ (CD
3COCD
3, ppm): 3.73-3.58 (m, 4H), 3.38-3.34 (t, 2H), 2.46-2.36 (m, 4H), 1.89-1.85 (m, 2H), 1.50-1.37 (m, 4H), (t 3H), illustrates that prepared is pure amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt ionic liquid to 0.92-0.88.
(2) get 10ml amylic thiophene two (trifluoromethyl sulphonyl) inferior amine salt ionic liquid, add two (trifluoromethyl sulphonyl) imines lithium salts (concentration is 0.4mol/L), add again ethylene carbonate (with ion liquid mass ratio be 1:20), fully dissolving mixes.
(3) the volume change figure of amylic thiophene two (trifluoromethyl sulphonyl) when the inferior amine salt il electrolyte is carried out the lithium secondary battery charge-discharge test that make for embodiment 3 of Fig. 5.Make button-shaped lithium secondary battery and test, wherein: battery size is CR2016; LiMn2O4 electrode (the commercialization electrode is directly buied) just very, electrode current collecting body is an aluminium foil; Barrier film is a Whatman GF/A type fibreglass diaphragm; Negative pole is a metal lithium sheet.Adopt LAND charge-discharge test instrument to test under normal temperature (25 ℃), charge-discharge magnification is 0.5C.Fig. 5 has shown that the battery initial capacity is 49mAh/g, is 38mAh/g through capacity after 50 charge and discharge cycles, and capability retention is 77.6%.
Claims (1)
1, a kind of alkylthrophene il electrolyte that is used for lithium secondary battery is characterized in that composed as follows:
Form jointly by alkylthrophene ionic liquid, lithium salts and organic electrolyte solvent; The molar concentration of lithium salts is 0.1mol/L to 1.5mol/L in the base, and the ion liquid mass ratio of organic electrolyte solvent and thiophene is m, 0≤m＜100;
Wherein, the ion liquid chemical structural formula of alkylthrophene is
R is a kind of in the straight chain aliphatic alkyl of C2～C6; A
-Be BF
4 -, PF
6 -Or CF
3SO
2)
2N
-
Lithium salts is tetrafluoro boric acid lithium salts, hexafluorophosphoric acid lithium salts or two (trifluoromethyl sulphonyl) imines lithium salts;
The organic electrolyte solvent 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, 1,3-propane sultone, 1,4-butyl sultone, dioxolanes or dimethoxy propane.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102412418A (en) * | 2010-09-26 | 2012-04-11 | 比亚迪股份有限公司 | Lithium ion battery electrolyte and lithium ion battery containing same |
| CN104638299A (en) * | 2015-02-15 | 2015-05-20 | 山东大学 | Secondary battery electrolyte solution having overcharging prevention function |
| CN105655643A (en) * | 2016-03-31 | 2016-06-08 | 宁德时代新能源科技股份有限公司 | Electrolyte and lithium ion battery comprising same |
| CN105789701A (en) * | 2016-03-31 | 2016-07-20 | 宁德时代新能源科技股份有限公司 | Electrolyte and lithium ion battery comprising same |
-
2008
- 2008-10-30 CN CNA2008102019350A patent/CN101425610A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102412418A (en) * | 2010-09-26 | 2012-04-11 | 比亚迪股份有限公司 | Lithium ion battery electrolyte and lithium ion battery containing same |
| CN102412418B (en) * | 2010-09-26 | 2014-03-12 | 比亚迪股份有限公司 | Lithium ion battery electrolyte and lithium ion battery containing same |
| CN104638299A (en) * | 2015-02-15 | 2015-05-20 | 山东大学 | Secondary battery electrolyte solution having overcharging prevention function |
| CN105655643A (en) * | 2016-03-31 | 2016-06-08 | 宁德时代新能源科技股份有限公司 | Electrolyte and lithium ion battery comprising same |
| CN105789701A (en) * | 2016-03-31 | 2016-07-20 | 宁德时代新能源科技股份有限公司 | Electrolyte and lithium ion battery comprising same |
| CN105655643B (en) * | 2016-03-31 | 2018-06-05 | 宁德时代新能源科技股份有限公司 | Electrolyte and lithium ion battery comprising same |
| CN105789701B (en) * | 2016-03-31 | 2019-04-02 | 宁德时代新能源科技股份有限公司 | Electrolyte and lithium ion battery comprising same |
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