CN108550915A - A kind of nickelic ternary lithium battery electrolytes of nitrile sulfone class and preparation method - Google Patents
A kind of nickelic ternary lithium battery electrolytes of nitrile sulfone class and preparation method Download PDFInfo
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- CN108550915A CN108550915A CN201810357149.3A CN201810357149A CN108550915A CN 108550915 A CN108550915 A CN 108550915A CN 201810357149 A CN201810357149 A CN 201810357149A CN 108550915 A CN108550915 A CN 108550915A
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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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
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- 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
- H01M10/058—Construction or manufacture
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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
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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- 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
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Abstract
The invention belongs to the technical field of lithium battery electrolytes, a kind of nickelic ternary lithium battery electrolytes of nitrile sulfone class and preparation method are provided.The electrolyte is made of organic solvent, lithium salts, additive, and the organic solvent contains nitrile sulfone.Preparation method is to remove excessive reactant by rotary evaporation, nitrile sulfone obtained is scattered in dimethyl carbonate and is uniformly mixed with lithium salts, additive using hydroxy sulfone, propylene cyanogen, solution of potassium carbonate and isobutanol Hybrid Heating back flow reaction.Compared with conventional method, the nitrile sulfone class lithium battery electrolytes of preparation of the invention, thermal stability is good, and electrochemical position is high, and viscosity is small, and chemical property is ideal, and overall performance is stablized, and safety is good, and preparation process is simple, of low cost, can be widely used for lithium battery industry.
Description
Technical field
The invention belongs to the technical fields of lithium battery electrolytes, provide a kind of nickelic ternary lithium battery electrolytes of nitrile sulfone class
And preparation method.
Background technology
Electrolyte is four big critical material of lithium ion battery（Anode, cathode, diaphragm, electrolyte）One of, it is known as lithium ion
" blood " of battery plays the role of conducting electronics in the battery between positive and negative anodes, is that lithium ion battery obtains high voltage, high ratio
The guarantee of the advantages that energy.Electrolyte is generally by the organic solvent of high-purity, electrolyte lithium salt（Lithium hexafluoro phosphate etc.）, necessary add
Add the raw materials such as agent, under certain condition, be formulated by a certain percentage.
Organic solvent is generally used in mixed way with high dielectric constant solvent in low viscosity solvent.Common electrolyte lithium salt has height
Lithium chlorate, lithium hexafluoro phosphate, LiBF4 etc. consider that lithium hexafluoro phosphate is commercialization lithium from cost, safety etc. are many-sided
The main electrolyte that ion battery uses.There are commonly solvents ethylene carbonate in lithium-ion battery electrolytes（EC）, carbon
Diethyl phthalate（DEC）, dimethyl carbonate（DMC）, methyl ethyl carbonate（EMC）, propene carbonate（PC）, ethyl acrylate（EA）、
Methyl acrylate（MA）Deng.
For lithium battery, the content of ternary material raising nickel can greatly promote the specific capacity of material, therefore nickelic three
A kind of ideal material of first material necessarily large-sized battery in future.But with the raising of nickel content, the Ni of positive electrode increases electricity
Pond performance declines.Therefore, the requirement to high performance electrolyte is also higher and higher.Sulfone class solvent has wider electrochemical window
Mouthful, therefore it can be used as functional electrolysis additive even solvent and uses, therefore receive significant attention.
It has been achieved in terms of lithium battery electrolytes technology of preparing, the especially preparation of sulfone class electrolyte both at home and abroad at present certain
Effect.Wherein rely to prolong and clear et al. has invented a kind of high-voltage lithium ion batteries electrolyte（Chinese invention patent application number
201510995274.3）, including organic solvent, lithium salts and lithium salts cosolvent, organic solvent include fluoro alkenyl 3- nitro -4- fluorine
Substituted alkyl phenylsulfone compounds and fluoro dintrile dialkyl ether compound；The high-voltage lithium ion batteries are improved with electrolysis liquid energy
Lithium battery energy density, and stability is good under high voltages, can significantly improve the service life and security performance of lithium battery.
In addition, Feng Shaowei et al. has invented a kind of electrolyte and the lithium ion battery including the electrolyte（Chinese invention patent application number
201610355485.5）, which includes organic solvent, lithium salts and additive, contains cyano sulfone compound in additive
With fluorophosphate lithium compound；When including simultaneously cyano sulfone compound and fluorophosphate lithium in electrolyte, cyano sulfone class
Passivating film will be formed on the surface of the pole piece of high-tension battery by closing object, and effective inhibition is obtained by the reaction in electrolyte and electrode, together
When, fluorophosphate lithium effectively can inhibit lithium salts to decompose, and improve the membrane impedance of pole piece；Under the common synergistic effect of the two, greatly
The big cycle performance for improving lithium ion battery；The storage performance of electrolyte is also significantly improved simultaneously.
As it can be seen that sulfone class electrolyte in the prior art is because its compound shows higher fusing point, can not on cathode shape
At stable SEI films, the decaying of battery performance is resulted in, while most sulfone compound is solid at room temperature, only
Liquid electrolyte could be constituted by being mixed with other solvents, limit its development and application.
Invention content
For such case, it is proposed that a kind of nickelic ternary lithium battery electrolytes of nitrile sulfone class and preparation method, it can be effective
The thermal stability in the application of sulfone class electrolyte is improved, and viscosity is small, intersolubility is good, has excellent performance.
To achieve the above object, specific technical solution of the present invention is as follows：
The component of a kind of nickelic ternary lithium battery electrolytes of nitrile sulfone class, the lithium battery electrolytes includes 75 ~ 83 weight of organic solvent
Measure part, 15 ~ 20 parts by weight of lithium salts, 2 ~ 5 parts by weight of additive;The organic solvent is nitrile sulfone and dimethyl carbonate with mass ratio 1:
3 disperse.
Preferably, the lithium salts is lithium hexafluoro phosphate, di-oxalate lithium borate, two（Fluorine sulphonyl）Imine lithium, lithium perchlorate, six
Fluorine closes at least one of arsenic acid lithium.
Preferably, the additive includes but not limited to film for additive, overcharge protection additives, infiltration additive.Root
It needs to select addition according to specific.As boracic class additive, organic phosphates additive, sulfur-containing additive, ion liquid addictive,
Crown ether, the anti-overcharge additive of dimethoxy nitrobenzene etc..
The electrolyte is made of organic solvent, lithium salts, additive, and the organic solvent is nitrile sulfone and dimethyl carbonate with matter
Measure ratio 1:3 disperse, and using hydroxy sulfone, propylene cyanogen, solution of potassium carbonate and isobutanol Hybrid Heating back flow reaction, pass through rotation
Evaporation removes excessive reactant, by nitrile sulfone and dimethyl carbonate with mass ratio 1:3 dispersions obtain organic solvent, be added lithium salts,
Additive is uniformly mixed, and has many advantages, such as that thermal stability is good, electrochemical position is high, viscosity is small, chemical property is ideal, and whole
Body performance is stablized, and safety is good, and preparation process is simple, of low cost, can be widely used for lithium battery industry.
The present invention also provides a kind of preparation method of the nickelic ternary lithium battery electrolytes of nitrile sulfone class, the specific steps of preparation
It is as follows：
（1）Hydroxy sulfone, propylene cyanogen, solution of potassium carbonate and isobutanol, 22 ~ 26h of heating reflux reaction are added into reaction kettle；
（2）Solution of potassium carbonate is added into reaction kettle, the reaction was continued 32 ~ 40h；
（3）Reaction system is cooled to room temperature, phosphoric acid neutralization reaction system is added, until pH value is 7；
（4）Excessive propylene cyanogen is removed by rotary evaporation, nitrile sulfone is made；
（5）By nitrile sulfone and dimethyl carbonate with mass ratio 1:3 are dispersed into organic solvent, and lithium salts and additive is added, and are uniformly mixed,
It can be prepared by the nickelic ternary lithium battery electrolytes of nitrile sulfone class.
Preferably, the mass concentration of the solution of potassium carbonate is 25 ~ 30%.
Preferably, step（1）The parts by weight of each raw material are 20 ~ 25 parts by weight of hydroxy sulfone, 18 ~ 22 weight of propylene cyanogen
Part, 15 parts by weight of solution of potassium carbonate, 38 ~ 47 parts by weight of isobutanol.
Preferably, step（2）The addition of the solution of potassium carbonate is 15 parts by weight.
Preferably, the reaction temperature is 120 ~ 140 DEG C.
Preferably, step（4）The heating temperature of the rotary evaporation is 80 ~ 85 DEG C.
The lithium salts such as widely used lithium hexafluoro phosphate of lithium battery electrolytes are generally especially sensitive to Determining Micro Acid and moisture content at present,
And then battery capacity is caused to decline, or even cause safety accident, and sulfone compound haves the shortcomings that fusing point height and viscosity are big.It grinds
Study carefully discovery, the addition of nitrile compounds can react with electrolyte under slightly sour environment and generate new compound amide, to
The effect of Determining Micro Acid and water in electrolyte is eliminated, and then lithium salts in sulfone class electrolyte can be inhibited to occur instead with Determining Micro Acid and water significantly
It answers, so as to improve battery performance.Meanwhile electrolyte thermal stability and electrochemical position also can be improved in nitrile compounds, with positive electrode
Surface metal atoms, which form strong coordination, which stablizes positive electrode and electrolyte interface, the high dipole moment of cyano, may pass through Li
Lithium salts is dissolved in+coordination help strong between cyano.
The present invention provides a kind of nickelic ternary lithium battery electrolytes of nitrile sulfone class and preparation methods, compared with prior art,
Its feature protruded and excellent effect are：
1. electrolyte prepared by the present invention, performance is stablized, and safety is good, can be widely used for lithium battery industry.
2. the preparation method of the present invention improves electrolyte thermal stability and electrochemical position by addition nitrile compounds, and
And inhibit lithium salts in the reaction of electrolyte, improve chemical property.
3. in the preparation of the present invention, nitrile compounds and the good intersolubility of conventional carbonate electrolyte are utilized so that electricity
Solution liquid can effectively reduce the viscosity of electrolyte with mixture linear carbonates.
4. the preparation method of the present invention, process is simple, of low cost, can promote production application.
Specific implementation mode
In the following, the present invention will be further described in detail by way of specific embodiments, but this should not be interpreted as to the present invention
Range be only limitted to example below.Without departing from the idea of the above method of the present invention, according to ordinary skill
The various replacements or change that knowledge and customary means are made, should be included in the scope of the present invention.
Embodiment 1
It is 27% solution of potassium carbonate and 43kg isobutyls that 23kg hydroxy sulfones, 19kg propylene cyanogen, 15kg mass concentrations are added into reaction kettle
Alcohol is heated to 132 DEG C of back flow reaction 23h；15kg solution of potassium carbonate, the reaction was continued 37h are added into reaction kettle；By reaction system
It is cooled to room temperature, phosphoric acid neutralization reaction system is added, until pH value is 7；At 83 DEG C excessive third is removed by rotary evaporation
Nitrile sulfone is made in alkene cyanogen；80kg nitriles sulfone is added with dimethyl carbonate with mass ratio in 17kg lithium hexafluoro phosphates and 3kg film for additive
1:It in organic solvent made of 3 dispersions, is uniformly mixed, you can the nickelic ternary lithium battery electrolytes of nitrile sulfone class are made.
Test method：
5mL electrolyte produced by the present invention is taken, using TDB-6A type computer closed mouth flash point testers, measures the flash-point of electrolyte；
Conductivity of the electrolyte at -20 DEG C, 30 DEG C and 80 DEG C is measured, to weigh influence of the temperature to viscosity.
The data obtained is as shown in table 1.
Embodiment 2
It is 25% solution of potassium carbonate and 47kg isobutyls that 20kg hydroxy sulfones, 18kg propylene cyanogen, 15kg mass concentrations are added into reaction kettle
Alcohol is heated to 120 DEG C of back flow reaction 26h；15kg solution of potassium carbonate, the reaction was continued 40h are added into reaction kettle；By reaction system
It is cooled to room temperature, phosphoric acid neutralization reaction system is added, until pH value is 7；At 80 DEG C excessive third is removed by rotary evaporation
Nitrile sulfone is made in alkene cyanogen；83kg nitriles sulfone and dimethyl carbonate is added in 15 kg di-oxalate lithium borates and 2kg overcharge protection additives
With mass ratio 1:It in organic solvent made of 3 dispersions, is uniformly mixed, you can the nickelic ternary lithium battery electrolytes of nitrile sulfone class are made.
Test method is consistent with embodiment 1, and the data obtained is as shown in table 1.
Embodiment 3
It is 30% solution of potassium carbonate and 38kg isobutyls that 25kg hydroxy sulfones, 22kg propylene cyanogen, 15kg mass concentrations are added into reaction kettle
Alcohol is heated to 140 DEG C of back flow reaction 22h；15kg solution of potassium carbonate, the reaction was continued 32h are added into reaction kettle；By reaction system
It is cooled to room temperature, phosphoric acid neutralization reaction system is added, until pH value is 7；At 85 DEG C excessive third is removed by rotary evaporation
Nitrile sulfone is made in alkene cyanogen；By 20 kg bis-（Fluorine sulphonyl）75kg nitriles sulfone and dimethyl carbonate is added in imine lithium and 5kg infiltration additives
With mass ratio 1:It in organic solvent made of 3 dispersions, is uniformly mixed, you can the nickelic ternary lithium battery electrolytes of nitrile sulfone class are made.
Test method is consistent with embodiment 1, and the data obtained is as shown in table 1.
Embodiment 4
It is 26% solution of potassium carbonate and 45kg isobutyls that 21kg hydroxy sulfones, 19kg propylene cyanogen, 15kg mass concentrations are added into reaction kettle
Alcohol is heated to 125 DEG C of back flow reaction 25h；15kg solution of potassium carbonate, the reaction was continued 38h are added into reaction kettle；By reaction system
It is cooled to room temperature, phosphoric acid neutralization reaction system is added, until pH value is 7；At 81 DEG C excessive third is removed by rotary evaporation
Nitrile sulfone is made in alkene cyanogen；80kg nitriles sulfone is added with dimethyl carbonate with mass ratio in 17 kg lithium perchlorates and 3kg film for additive
1:It in organic solvent made of 3 dispersions, is uniformly mixed, you can the nickelic ternary lithium battery electrolytes of nitrile sulfone class are made.
Test method is consistent with embodiment 1, and the data obtained is as shown in table 1.
Embodiment 5
It is 28% solution of potassium carbonate and 40kg isobutyls that 24kg hydroxy sulfones, 21kg propylene cyanogen, 15kg mass concentrations are added into reaction kettle
Alcohol is heated to 135 DEG C of back flow reaction 23h；15kg solution of potassium carbonate, the reaction was continued 35h are added into reaction kettle；By reaction system
It is cooled to room temperature, phosphoric acid neutralization reaction system is added, until pH value is 7；At 84 DEG C excessive third is removed by rotary evaporation
Nitrile sulfone is made in alkene cyanogen；18 kg hexafluoros are closed into the sour lithium of arsenic (V) and 78kg nitriles sulfone and carbonic acid diformazan is added in 4kg overcharge protection additives
Ester is with mass ratio 1:It in organic solvent made of 3 dispersions, is uniformly mixed, you can the nickelic ternary lithium battery electrolysis of nitrile sulfone class is made
Liquid.
Test method is consistent with embodiment 1, and the data obtained is as shown in table 1.
Embodiment 6
It is 28% solution of potassium carbonate and 43kg isobutyls that 22kg hydroxy sulfones, 20kg propylene cyanogen, 15kg mass concentrations are added into reaction kettle
Alcohol is heated to 130 DEG C of back flow reactions for 24 hours；15kg solution of potassium carbonate, the reaction was continued 36h are added into reaction kettle；By reaction system
It is cooled to room temperature, phosphoric acid neutralization reaction system is added, until pH value is 7；At 82 DEG C excessive third is removed by rotary evaporation
Nitrile sulfone is made in alkene cyanogen；79kg nitriles sulfone and carbonic acid two is added in 18 kg lithium hexafluoro phosphates and 3kg dimethoxy nitrobenzene additives
Methyl esters is with mass ratio 1:It in organic solvent made of 3 dispersions, is uniformly mixed, you can the nickelic ternary lithium battery electrolysis of nitrile sulfone class is made
Liquid.
Test method is consistent with embodiment 1, and the data obtained is as shown in table 1.
Comparative example 1
Replace nitrile sulfone as the organic solvent of lithium battery electrolytes, lithium salts, additive and proportioning and embodiment 6 using ethylene carbonate
Unanimously.
Test method is consistent with embodiment 1, and the data obtained is as shown in table 1.
Comparative example 2
Replace nitrile sulfone as the organic solvent of lithium battery electrolytes, lithium salts, additive and proportioning and embodiment 6 using dipropyl carbonate
Unanimously.
Test method is consistent with embodiment 1, and the data obtained is as shown in table 1.
Table 1：
Claims (9)
1. a kind of nickelic ternary lithium battery electrolytes of nitrile sulfone class, it is characterised in that：The component of the lithium battery electrolytes includes
75 ~ 83 parts by weight of solvent, 15 ~ 20 parts by weight of lithium salts, 2 ~ 5 parts by weight of additive;The organic solvent is nitrile sulfone and carbonic acid two
Methyl esters is with mass ratio 1:3 disperse.
2. the nickelic ternary lithium battery electrolytes of a kind of nitrile sulfone class according to claim 1, it is characterised in that：The lithium salts is six
Lithium fluophosphate, di-oxalate lithium borate, two（Fluorine sulphonyl）Imine lithium, lithium perchlorate, hexafluoro close at least one of arsenic acid lithium.
3. the nickelic ternary lithium battery electrolytes of a kind of nitrile sulfone class according to claim 1, it is characterised in that：The additive packet
Include but be not limited to film for additive, overcharge protection additives, infiltration additive.
4. a kind of any one of claim 1-3 preparation methods of the nickelic ternary lithium battery electrolytes of nitrile sulfone class, feature exist
In preparation is as follows：
（1）Hydroxy sulfone, propylene cyanogen, solution of potassium carbonate and isobutanol, 22 ~ 26h of heating reflux reaction are added into reaction kettle；
（2）Solution of potassium carbonate is added into reaction kettle, the reaction was continued 32 ~ 40h；
（3）Reaction system is cooled to room temperature, phosphoric acid neutralization reaction system is added, until pH value is 7；
（4）Excessive propylene cyanogen is removed by rotary evaporation, nitrile sulfone is made；
（5）By nitrile sulfone and dimethyl carbonate with mass ratio 1:3 are dispersed into organic solvent, and lithium salts and additive is added, and are uniformly mixed,
It can be prepared by the nickelic ternary lithium battery electrolytes of nitrile sulfone class.
5. the preparation method of the nickelic ternary lithium battery electrolytes of a kind of nitrile sulfone class according to claim 4, it is characterised in that：Step
Suddenly（1）The mass concentration of the solution of potassium carbonate is 25 ~ 30%.
6. the preparation method of the nickelic ternary lithium battery electrolytes of a kind of nitrile sulfone class according to claim 4, it is characterised in that：Step
Suddenly（1）The parts by weight of each raw material are 20 ~ 25 parts by weight of hydroxy sulfone, 18 ~ 22 parts by weight of propylene cyanogen, 15 weight of solution of potassium carbonate
Measure part, 38 ~ 47 parts by weight of isobutanol.
7. the preparation method of the nickelic ternary lithium battery electrolytes of a kind of nitrile sulfone class according to claim 4, it is characterised in that：Step
Suddenly（2）The addition of the solution of potassium carbonate is 15 parts by weight.
8. the preparation method of the nickelic ternary lithium battery electrolytes of a kind of nitrile sulfone class according to claim 4, it is characterised in that：Institute
It is 120 ~ 140 DEG C to state reaction temperature.
9. the preparation method of the nickelic ternary lithium battery electrolytes of a kind of nitrile sulfone class according to claim 4, it is characterised in that：Step
Suddenly（4）The heating temperature of the rotary evaporation is 80 ~ 85 DEG C.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110544795A (en) * | 2019-08-20 | 2019-12-06 | 大同新成新材料股份有限公司 | preparation method and preparation device of high-voltage lithium battery electrolyte |
| CN118054087A (en) * | 2024-04-16 | 2024-05-17 | 蜂巢能源科技股份有限公司 | Electrolyte, electrolyte injection method and lithium metal battery |
-
2018
- 2018-04-20 CN CN201810357149.3A patent/CN108550915A/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110544795A (en) * | 2019-08-20 | 2019-12-06 | 大同新成新材料股份有限公司 | preparation method and preparation device of high-voltage lithium battery electrolyte |
| CN118054087A (en) * | 2024-04-16 | 2024-05-17 | 蜂巢能源科技股份有限公司 | Electrolyte, electrolyte injection method and lithium metal battery |
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Application publication date: 20180918 |