CN109301329A - Two oxime derivatives are preparing the application in lithium-ion battery electrolytes - Google Patents
Two oxime derivatives are preparing the application in lithium-ion battery electrolytes Download PDFInfo
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- CN109301329A CN109301329A CN201811167148.9A CN201811167148A CN109301329A CN 109301329 A CN109301329 A CN 109301329A CN 201811167148 A CN201811167148 A CN 201811167148A CN 109301329 A CN109301329 A CN 109301329A
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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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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Abstract
The invention discloses two oxime derivatives to prepare the application in lithium-ion battery electrolytes, additive one of of the present invention using two oxime derivatives as lithium-ion battery electrolytes, complex precipitating can be formed with the positive electrode transition metal ions for being dissolved into electrolyte in cyclic process, slow down metal ion in the deposition of negative terminal surface and the growth of cathode SEI, it is obviously improved lithium ion battery, especially using nickel-containing material as the cycle performance of the lithium ion battery of positive electrode.
Description
Technical field
The invention belongs to technical field of lithium ion, and in particular to two oxime derivatives are preparing lithium ion battery electrolysis
Application in liquid.
Background technique
Lithium ion battery has been widely used in portable due to having many advantages, such as energy density height and having extended cycle life
Electronic product.Compared with cobalt acid lithium with LiFePO 4 material, nickeliferous positive electrode due to specific capacity with higher, at
For the mainstream of new-energy automobile field lithium-ion-power cell.For example, nickeliferous ternary material and NCA material is most to be closed at present
The new-energy automobile power battery positive electrode of note, and rich lithium material is generally considered follow-on power battery anode material
Material.
Lithium battery main problem existing for use process of nickeliferous positive electrode production is that cycle performance is not ideal enough, main
Reason is wanted to be the decay of nickel-containing material crystal structure in cyclic process, the accumulation of second particle internal stress and transition metal
The problems such as dissolution of element.Improving cycle performance of battery on the one hand can be by carrying out material modification, such as element to nickel-containing material
Bulk phase-doped and surface cladding, on the other hand can also develop suitable electrolysis additive, be improved by electrolyte nickeliferous
The cycle performance of material.
In the prior art, using two oxime derivatives as lithium-ion battery electrolytes additive, and electrolyte is prepared with this
It not yet appears in the newspapers to improve the relevant technologies of nickeliferous positive electrode cycle performance.
Summary of the invention
It is an object of the invention to overcome prior art defect, two oxime derivatives are provided and are preparing lithium ion battery electrolysis
Application in liquid.
Another object of the present invention is to provide a kind of lithium-ion battery electrolytes.
A further object of the present invention is to provide a kind of lithium ion batteries.
Technical scheme is as follows:
Two oxime derivatives are preparing the application in lithium-ion battery electrolytes, and the material of the anode of the lithium ion battery contains
The structural formula of nickel, two oxime derivatives isWherein,
The alkyl or halogenated alkyl that R1 is H, halogen, carbon atom number are 1-5,
The alkyl or halogenated alkyl that R2 is H, halogen, carbon atom number are 1-5,
X1 be H or alkali metal,
X2 is H or alkali metal.
In a preferred embodiment of the invention, in the lithium-ion battery electrolytes, two oxime derivatives
Content be 0.01-10wt%.
It in a preferred embodiment of the invention, further include lithium salts, You Jirong in the lithium-ion battery electrolytes
Agent and additive.
It is further preferred that the lithium salts includes lithium hexafluoro phosphate (LiPF6), LiBF4 (LiBF4), double oxalic acid boron
At least one of sour lithium (LiBOB) and difluorine oxalic acid boracic acid lithium (LiODFB)；The organic solvent includes ethylene carbonate
(EC), dimethyl carbonate (DMC), diethyl carbonate (DEC), methyl ethyl carbonate (EMC), methyl propyl carbonate
(MPC) and at least one of butylene (BC)；The additive include vinylene carbonate, fluorinated ethylene carbonate,
Vinyl vinylene carbonate, ethylene sulfite, vinyl ethylene sulfite, propylene sulfite, dimethyl suflfate and
At least one of sulfuric acid acrylic ester.
Another technical solution of the invention is as follows:
The material of a kind of lithium-ion battery electrolytes, the anode of the lithium ion battery is nickeliferous, contains two oxime derivatives, should
The structural formula of two oxime derivatives isWherein,
The alkyl or halogenated alkyl that R1 is H, halogen, carbon atom number are 1-5,
The alkyl or halogenated alkyl that R2 is H, halogen, carbon atom number are 1-5,
X1 be H or alkali metal,
X2 is H or alkali metal.
In a preferred embodiment of the invention, the content of two oxime derivatives is 0.01-10wt%.
It in a preferred embodiment of the invention, further include lithium salts, organic solvent and additive.
It is further preferred that the lithium salts includes lithium hexafluoro phosphate (LiPF6), LiBF4 (LiBF4), double oxalic acid boron
At least one of sour lithium (LiBOB) and difluorine oxalic acid boracic acid lithium (LiODFB)；The organic solvent includes ethylene carbonate
(EC), dimethyl carbonate (DMC), diethyl carbonate (DEC), methyl ethyl carbonate (EMC), methyl propyl carbonate
(MPC) and at least one of butylene (BC)；The additive include vinylene carbonate, fluorinated ethylene carbonate,
Vinyl vinylene carbonate, ethylene sulfite, vinyl ethylene sulfite, propylene sulfite, dimethyl suflfate and
At least one of sulfuric acid acrylic ester.
Yet another aspect of the invention is as follows:
The material of a kind of lithium ion battery, anode is nickeliferous, has above-mentioned lithium-ion battery electrolytes.
The beneficial effects of the present invention are: additive of the present invention using two oxime derivatives as lithium-ion battery electrolytes it
One, complex precipitating can be formed with the positive electrode transition metal ions for being dissolved into electrolyte in cyclic process, slow down metal
Ion is in the deposition of negative terminal surface and the growth of cathode SEI, hence it is evident that improves lithium ion battery, is especially anode with nickel-containing material
The cycle performance of the lithium ion battery of material.
Detailed description of the invention
Fig. 1 is the circulation volume conservation rate comparison diagram of the embodiment of the present invention 6, comparative example 1 and comparative example 2.
Specific embodiment
Technical solution of the present invention is further explained and described below by way of specific embodiment.
In following embodiments, affiliated organic solvent is selected from well known to a person skilled in the art organic solvent, in order to facilitate this
EC+EMC, the two mass ratio 3: 7 are selected in the elaboration of invention.
In following embodiments, the electrolyte lithium salt selects lithium hexafluoro phosphate (LiPF6), it is of the invention for convenience to explain
It states, fixed lithium salts LiPF6Concentration be 1mol/L.
Embodiment 1
Electrolyte quota step: in the argon atmosphere glove box of water content < 5ppm, by 3.00g EC and 7.00g EMC
Mixed, backward mixed solution in be slowly added to the 1.39g LiPF sufficiently dried6, to LiPF6After being completely dissolved, then plus
Enter 0.115g dimethylglyoxime, obtains electrolyte after mixing.
Electrolyte composition is as follows: lithium salts LiPF6Concentration 1.0molL-1, organic solvent EC: EMC=3: 7 (mass ratio) adds
Adding agent dimethylglyoxime to account for the mass percentage of electrolyte total amount is 1%.
The flexible-packed battery of the non-fluid injection of Selection of Battery purchase, injects above-mentioned electrolyte up to lithium ion battery.Battery institute
The positive electrode used is nickel-cobalt lithium manganate material, and negative electrode material is modified natural graphite material, and battery design capacity is
1000mAh, battery liquid-filling amount are 4.0g.Above-mentioned battery is subjected to charge and discharge cycles test on charge and discharge instrument, test temperature is
25 DEG C, circulating ratio 1C, charging/discharging voltage 3.0-4.2V.Calculate the capacity retention ratio of battery after recycling.Calculation formula is such as
Under:
N-th circulation volume conservation rate (%)=(n-th cyclic discharge capacity/for the first time cyclic discharge capacity) * 100%.
Embodiment 2
Additive uses dimethylglyoxime list lithium salts in the present embodiment, and two ketoxime list lithium salts account for the quality percentage of electrolyte total amount
Content is 1%.Other are same as Example 1.
Embodiment 3
Additive accounts for the quality hundred of electrolyte total amount using the double lithium salts of dimethylglyoxime, the double lithium salts of dimethylglyoxime in the present embodiment
Dividing content is 1%.Other are same as Example 1.
Embodiment 4
Additive uses dimethylglyoxime list lithium salts in the present embodiment, and dimethylglyoxime list lithium salts accounts for the quality hundred of electrolyte total amount
Dividing content is 0.01%.Other are same as Example 1.
Embodiment 5
Additive uses dimethylglyoxime list lithium salts in the present embodiment, and dimethylglyoxime list lithium salts accounts for the quality hundred of electrolyte total amount
Dividing content is 10%.Other are same as Example 1.
Embodiment 6
Additive uses dimethylglyoxime list lithium salts and vinylene carbonate in the present embodiment, and wherein dimethylglyoxime list lithium salts accounts for
The mass percentage of electrolyte total amount is 1%, and the mass percentage that vinylene carbonate accounts for electrolyte total amount is 1%.Its
He is same as Example 1.
Embodiment 7
Additive uses dimethylglyoxime mono-sodium salt in the present embodiment, and dimethylglyoxime mono-sodium salt accounts for the quality hundred of electrolyte total amount
Dividing content is 1%.Other are same as Example 1.
Comparative example 1
Electrolyte selects the basic electrolyte not containing any additive, electrolyte composition are as follows: lithium salts LiPF in this comparative example6
Concentration 1.0molL-1, organic solvent EC: EMC=3: 7 (mass ratio).Other are same as Example 1.
Comparative example 2
Use vinylene carbonate for additive in this comparative example, vinylene carbonate accounts for the quality percentage of electrolyte total amount
Content is 2%.Other are same as Example 1.
1~2 the performance test results of 1 Examples 1 to 7 of table and comparative example:
| 400 circulation volume conservation rates (%) | |
| Embodiment 1 | 78.3 |
| Embodiment 2 | 92.5 |
| Embodiment 3 | 88.4 |
| Embodiment 4 | 82.3 |
| Embodiment 5 | 92.3 |
| Embodiment 6 | 95.9 |
| Embodiment 7 | 90.3 |
| Comparative example 1 | 68.4 |
| Comparative example 2 | 86.6 |
From comparative example 1 as can be seen that cycle performance is bad without the electrolyte battery using additive, battery after 400 circles
Capacity retention ratio there was only 68.4%.It is compared with comparative example 1, two oxime derivatives is added as electrolysis additive, battery follows
Ring performance has different degrees of improvement, wherein the improvement of single lithium carbonate is preferable.From embodiment 4, additive is dense
Degree is unsuitable too low, and the additive for crossing low concentration is not enough to precipitate the transition metal ions in electrolyte.From embodiment 2 and embodiment
5 see, when additive reaches suitable concentration, circulating battery just has improving significantly, and continue to improve the dense of additive
Degree, circulating battery will not be promoted further.
From embodiment 6 as can be seen that two oxime derivatives additives can be with existing common additive such as carbonic acid Asia second
Enester is used in combination, and can achieve better effect, and cycle performance of battery is further promoted.As shown in Figure 1, carbonic acid is used alone
For vinylene as additive, battery will appear the phenomenon that loop attenuation is accelerated after being recycled to a fixing turn, and be added simultaneously
The battery of vinylene carbonate and dimethylglyoxime list lithium salts as additive, circulation volume keep highly stable.
Those of ordinary skill in the art still are able to it is found that when technical solution of the present invention changes in following ranges
To same as the previously described embodiments or similar technical effect, protection scope of the present invention is still fallen within:
The structural formula of two oxime derivatives isWherein,
The alkyl or halogenated alkyl that R1 is H, halogen, carbon atom number are 1-5,
The alkyl or halogenated alkyl that R2 is H, halogen, carbon atom number are 1-5,
X1 be H or alkali metal,
X2 is H or alkali metal.
In lithium-ion battery electrolytes, the content of two oxime derivatives is 0.01-10wt%, lithium ion battery electrolysis
It further include lithium salts, organic solvent and additive in liquid.The lithium salts includes lithium hexafluoro phosphate (LiPF6), LiBF4
(LiBF4), at least one of di-oxalate lithium borate (LiBOB) and difluorine oxalic acid boracic acid lithium (LiODFB)；The organic solvent
Including ethylene carbonate (EC), dimethyl carbonate (DMC), diethyl carbonate (DEC), methyl ethyl carbonate (EMC), first
At least one of base propyl carbonate (MPC) and butylene (BC)；The additive includes vinylene carbonate, fluoro
Ethylene carbonate, vinyl vinylene carbonate, ethylene sulfite, vinyl ethylene sulfite, propylene sulfite, sulphur
At least one of dimethyl phthalate and sulfuric acid acrylic ester.
The foregoing is only a preferred embodiment of the present invention, the range that the present invention that therefore, it cannot be limited according to is implemented, i.e.,
Equivalent changes and modifications made in accordance with the scope of the invention and the contents of the specification should still be within the scope of the present invention.
Claims (9)
1. two oxime derivatives are preparing the application in lithium-ion battery electrolytes, the material of the anode of the lithium ion battery contains
Nickel, it is characterised in that: the structural formula of two oxime derivatives isWherein,
The alkyl or halogenated alkyl that R1 is H, halogen, carbon atom number are 1-5,
The alkyl or halogenated alkyl that R2 is H, halogen, carbon atom number are 1-5,
X1 be H or alkali metal,
X2 is H or alkali metal.
2. application as described in claim 1, it is characterised in that: in the lithium-ion battery electrolytes, two oximes is derivative
The content of object is 0.01-10wt%.
3. application as described in claim 1, it is characterised in that: further include lithium salts in the lithium-ion battery electrolytes, organic
Solvent and additive.
4. application as claimed in claim 3, it is characterised in that: the lithium salts includes lithium hexafluoro phosphate, LiBF4, double grass
At least one of sour lithium borate and difluorine oxalic acid boracic acid lithium；The organic solvent include ethylene carbonate, dimethyl carbonate,
At least one of diethyl carbonate, methyl ethyl carbonate, methyl propyl carbonate and butylene；The additive
Including vinylene carbonate, fluorinated ethylene carbonate, vinyl vinylene carbonate, ethylene sulfite, vinyl sulfurous acid
At least one of vinyl acetate, propylene sulfite, dimethyl suflfate and sulfuric acid acrylic ester.
5. the material of a kind of lithium-ion battery electrolytes, the anode of the lithium ion battery is nickeliferous, it is characterised in that: contain two oximes
The structural formula of derivative, two oxime derivatives isWherein,
The alkyl or halogenated alkyl that R1 is H, halogen, carbon atom number are 1-5,
The alkyl or halogenated alkyl that R2 is H, halogen, carbon atom number are 1-5,
X1 be H or alkali metal,
X2 is H or alkali metal.
6. a kind of lithium-ion battery electrolytes as claimed in claim 5, it is characterised in that: the content of two oxime derivatives
For 0.01-10wt%.
7. a kind of lithium-ion battery electrolytes as claimed in claim 5, it is characterised in that: further include lithium salts, organic solvent and
Additive.
8. a kind of lithium-ion battery electrolytes as claimed in claim 7, it is characterised in that: the lithium salts includes hexafluorophosphoric acid
At least one of lithium, LiBF4, di-oxalate lithium borate and difluorine oxalic acid boracic acid lithium；The organic solvent includes carbonic acid second
In enester, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, methyl propyl carbonate and butylene
It is at least one；The additive includes vinylene carbonate, fluorinated ethylene carbonate, vinyl vinylene carbonate, sulfurous acid
At least one of vinyl acetate, vinyl ethylene sulfite, propylene sulfite, dimethyl suflfate and sulfuric acid acrylic ester.
9. the material of a kind of lithium ion battery, anode is nickeliferous, it is characterised in that: have such as any right in claim 5 to 8
It is required that the lithium-ion battery electrolytes.
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| CN201811167148.9A CN109301329B (en) | 2018-10-08 | 2018-10-08 | Application of dioxime derivatives in preparation of lithium ion battery electrolyte |
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| CN201811167148.9A CN109301329B (en) | 2018-10-08 | 2018-10-08 | Application of dioxime derivatives in preparation of lithium ion battery electrolyte |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110165299A (en) * | 2019-05-06 | 2019-08-23 | 中南大学 | A kind of lithium-sulfur cell, electrolyte and its application |
| CN111129597A (en) * | 2019-12-27 | 2020-05-08 | 惠州市豪鹏科技有限公司 | Electrolyte and lithium ion battery |
| CN111244547A (en) * | 2020-01-21 | 2020-06-05 | 四川虹微技术有限公司 | Electrolyte containing aromatic oxime additive and preparation method and application thereof |
| CN111463444A (en) * | 2020-04-09 | 2020-07-28 | 西安交通大学 | Water system organic oximes/zinc composite flow battery and assembling method thereof |
| CN111934012A (en) * | 2020-08-19 | 2020-11-13 | 四川虹微技术有限公司 | Lithium ion battery electrolyte, preparation method and application thereof |
| CN113764730A (en) * | 2020-06-01 | 2021-12-07 | 比亚迪股份有限公司 | Lithium ion battery electrolyte and lithium ion battery |
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| JP2009117081A (en) * | 2007-11-02 | 2009-05-28 | Asahi Kasei Chemicals Corp | Electrolyte solution for lithium-ion secondary battery and lithium-ion secondary battery |
| EP2463950B1 (en) * | 2010-12-07 | 2013-08-28 | Samsung Electronics Co., Ltd. | Lithium air battery |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110165299A (en) * | 2019-05-06 | 2019-08-23 | 中南大学 | A kind of lithium-sulfur cell, electrolyte and its application |
| CN110165299B (en) * | 2019-05-06 | 2022-02-01 | 中南大学 | Lithium-sulfur battery, electrolyte and application thereof |
| CN111129597A (en) * | 2019-12-27 | 2020-05-08 | 惠州市豪鹏科技有限公司 | Electrolyte and lithium ion battery |
| CN111244547A (en) * | 2020-01-21 | 2020-06-05 | 四川虹微技术有限公司 | Electrolyte containing aromatic oxime additive and preparation method and application thereof |
| CN111244547B (en) * | 2020-01-21 | 2021-09-17 | 四川虹微技术有限公司 | Electrolyte containing aromatic oxime additive and preparation method and application thereof |
| CN111463444A (en) * | 2020-04-09 | 2020-07-28 | 西安交通大学 | Water system organic oximes/zinc composite flow battery and assembling method thereof |
| CN111463444B (en) * | 2020-04-09 | 2021-03-16 | 西安交通大学 | Water system organic oximes/zinc composite flow battery and assembling method thereof |
| CN113764730A (en) * | 2020-06-01 | 2021-12-07 | 比亚迪股份有限公司 | Lithium ion battery electrolyte and lithium ion battery |
| CN113764730B (en) * | 2020-06-01 | 2023-11-14 | 比亚迪股份有限公司 | Lithium ion battery electrolyte and lithium ion battery |
| CN111934012A (en) * | 2020-08-19 | 2020-11-13 | 四川虹微技术有限公司 | Lithium ion battery electrolyte, preparation method and application thereof |
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