CN111253426A - 4- (trimethylsilyloxy) -3-pentene-2-ketone additive and lithium ion battery electrolyte thereof - Google Patents

4- (trimethylsilyloxy) -3-pentene-2-ketone additive and lithium ion battery electrolyte thereof Download PDF

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CN111253426A
CN111253426A CN202010061777.4A CN202010061777A CN111253426A CN 111253426 A CN111253426 A CN 111253426A CN 202010061777 A CN202010061777 A CN 202010061777A CN 111253426 A CN111253426 A CN 111253426A
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carbonate
lithium
ion battery
lithium ion
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王健
朱学全
王建斌
唐明明
潘立宁
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Shanshan Advanced Materials Quzhou Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0894—Compounds with a Si-O-O linkage
    • 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
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/058—Construction or manufacture
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
    • H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
    • 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
    • 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
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    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

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Abstract

The invention discloses a 4- (trimethylsiloxy) -3-pentene-2-ketone additive and a lithium ion battery electrolyte containing the additive, wherein the 4- (trimethylsiloxy) -3-pentene-2-ketone additive has dual-functional activity of an HF scavenger and a protective film precursor, and the electrolyte containing the 4- (trimethylsiloxy) -3-pentene-2-ketone additive improves the coulombic efficiency and the cycle retention rate of a Li/LiNi0.5Mn1.5O4(LNMO) half battery and a graphite/LNMO full battery.

Description

4- (trimethylsilyloxy) -3-pentene-2-ketone additive and lithium ion battery electrolyte thereof
Technical Field
The invention relates to the technical field of lithium ion batteries, and particularly relates to a 4- (trimethylsiloxy) -3-penten-2-one additive and a lithium ion battery electrolyte thereof.
Background
With the rapid development of the lithium ion battery market, improving the energy density and power density of the lithium ion battery encounters some technical bottlenecks in development. For example, it is difficult to find electrode materials and electrolyte systems compatible with them that operate at high voltages. Novel positive electrode material such as LiCuxMn2-xO4(4.9V vs.Li+/Li)、LiNi0.5Mn1.5O4(4.7V vs.Li+/Li)、LiNixCo1-xPO4(4.8-5.1V vs.Li+/Li) and Li2CoPO4F(5.1V vs.Li+/Li) has attracted the researchers' attention as having a higher operating voltage. Although these electrode materials can operate at high voltages, the voltages exceed the electrochemical stability window of conventional carbonates. The development of high energy density positive electrode materials is restricted by the stability of the electrolyte under high voltage, so that the development of 5V class high voltage electrolyte is urgent.
Disclosure of Invention
In view of the problems in the prior art, the invention aims to provide a 4- (trimethylsiloxy) -3-penten-2-one additive and a lithium ion battery electrolyte thereof. The 4- (trimethylsiloxy) -3-pentene-2-one additive has the dual-function activity of an HF scavenger and a protective film precursor, and the electrolyte containing the 4- (trimethylsiloxy) -3-pentene-2-one additive improves Li/LiNi0.5Mn1.5O4Coulombic efficiency and cycle retention for (LNMO) half cells and graphite/LNMO full cells.
In order to achieve the purpose, the invention adopts the technical scheme that: a4- (trimethylsilyloxy) -3-penten-2-one additive having the formula:
Figure BDA0002374740130000021
wherein R1, R2 and R3 are respectively selected from substituted or unsubstituted straight-chain alkyl with 1-5 carbon atoms, alkenyl containing five-membered cyclic carbonate, carbonate with part of hydrogen substituted by halogen, phenyl and cyano.
As a preferred embodiment of the present invention, the 4- (trimethylsiloxy) -3-penten-2-one additive is selected from at least one of the compounds represented by the following structural formula:
Figure BDA0002374740130000022
the invention also provides a lithium ion battery electrolyte containing the 4- (trimethylsiloxy) -3-pentene-2-ketone additive, which comprises the following components in percentage by mass in the lithium ion battery electrolyte:
5 to 19 percent of lithium salt
80-94% of organic solvent
4- (trimethylsiloxy) -3-penten-2-one additive 0.05-2%
In a preferred embodiment of the present invention, the lithium salt is at least one selected from the group consisting of lithium hexafluorophosphate, lithium bis (oxalato) borate, lithium tetrafluoroborate, lithium perchlorate, lithium bis (trifluoromethylsulfonyl) imide, lithium methylsulfonate and lithium trifluoromethylsulfonate.
In a preferred embodiment of the present invention, the organic solvent is selected from one or more of esters, amines, sulfones and nitriles. The esters are selected from at least one of ethylene carbonate, propylene carbonate, butylene carbonate, gamma-butyrolactone, dipropyl carbonate, dimethyl sulfite, vinylene carbonate, methyl propyl carbonate, ethyl acetate, methyl butyrate, ethyl butyrate, methyl propionate, ethyl propionate, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate and propyl acetate; the amine is selected from at least one of N-methylacetamide, N-methylformamide, dimethylformamide and diethylformamide; the sulfones are selected from at least one of dimethyl sulfoxide, sulfolane, diphenyl sulfoxide, thionyl chloride and dipropyl sulfone; the nitrile is at least one of acetonitrile, succinonitrile, adiponitrile and glutaronitrile. The organic solvent is more preferably a mixture of Ethylene Carbonate (EC), diethyl carbonate (DEC), Ethyl Methyl Carbonate (EMC).
In a preferred embodiment of the present invention, the oxidation potential of the lithium ion battery electrolyte is 4.5 to 5V.
Siloxane groups and lithium hexafluorophosphate (LiPF) in the 4- (trimethylsiloxy) -3-penten-2-one additive of the invention6) The Hydrogen Fluoride (HF) generated by hydrolysis reacts to generate 4-hydroxy-3-en-2-one (HPO). The HPO generated by electrochemical oxidation reaction and carbon-carbon (C ═ C) double bond initiate free radical polymerization to form a protective surface film. The surface film obtained from the electrolyte added with the 4- (trimethylsiloxy) -3-penten-2-one additive has better passivation capability, inhibits the decomposition of the electrolyte through excellent passivation capability, and provides favorable characteristics for the electrochemical performance of the lithium ion battery.
The 4- (trimethylsilyloxy) -3-penten-2-one additives of the invention are commercially available or can be prepared by the following method:
(1) according to molar ratio of acrylic acid: 1-propylene sulfuric anhydride is 1:1, acrylic acid and 1-propylene sulfuric anhydride are taken to be stirred and mixed evenly, then the mixture is refluxed for 6 to 8 hours at the temperature of 80 to 100 ℃, and the obtained mixed liquid A is subjected to rotary evaporation and purification at the temperature of 60 ℃ to obtain a reaction product;
(2) adding trimethoxy silane into the product obtained in the step (1) according to a molar ratio to obtain a mixed liquid B, and then mixing the mixed liquid B: adding toluene as solvent, adding 5mg of platinum as hydrosilylation catalyst, refluxing at 40-80 deg.C for 6h, and removing solvent by rotary evaporation at 80 deg.C to obtain the structure of R1, R2 and R3 all being methyl.
For grafting of R1, R2 and R3 with different structures, the substance obtained in the step (2) can be uniformly mixed with R1-OH, R2-OH and R3-OH, a solvent toluene is added according to the volume ratio of 1:10, reflux is carried out for 2-4h for dehydration at the temperature of 80-100 ℃, and the obtained mixed solution is subjected to rotary evaporation and purification at the temperature of 60-80 ℃ to obtain the additives with different structures of R1, R2 and R3.
Compared with the prior art, the invention has the advantages that:
1. the 4- (trimethylsiloxy) -3-pentene-2-one additive contains abundant electron-withdrawing groups, the surface film of the additive has better passivation capability, the oxidation of electrolyte is inhibited through the excellent passivation capability, and the generation and the deposition of HF (hydrogen fluoride) on the surface film are inhibited, so that the electrolyte containing the 4- (trimethylsiloxy) -3-pentene-2-one additive has high oxidation potential (more than 4.5V).
2. The electrolyte containing the 4- (trimethylsiloxy) -3-pentene-2-ketone additive has high oxidation potential, can obviously improve the voltage of a lithium ion battery by matching with a high-voltage anode material, thereby achieving the purpose of improving the energy density of the lithium ion battery, and meanwhile, the electron-withdrawing group of the additive has better passivation capability, thereby prolonging the cycle performance of the battery.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments.
It is to be understood that the following description is only illustrative of the present invention and is not to be construed as limiting the present invention.
Examples the structural formula of the 4- (trimethylsilyloxy) -3-penten-2-one additive is characterized as follows:
compound 1 junction
Formula (II):
Figure BDA0002374740130000041
compound 2 structural formula:
Figure BDA0002374740130000042
compound 3 structural formula:
Figure BDA0002374740130000043
compound 4 structural formula:
Figure BDA0002374740130000044
some of the materials in the comparative examples are illustrated below:
VC: vinylene carbonate
ES: vinyl sulfite example 1
The performance and the application prospect in a high-voltage battery system are better.
Preparing an electrolyte:
uniformly mixing Ethylene Carbonate (EC), diethyl carbonate (DEC) and methyl ethyl carbonate (EMC) in a mass ratio of 5: 2: 3 in a glove box filled with argon (the oxygen content is less than or equal to 1ppm and the water content is less than or equal to 1ppm) to obtain a mixed solvent, and then adding lithium hexafluorophosphate (LiPF) into the mixed solvent6) And dissolving to obtain a solution containing lithium hexafluorophosphate. Thereafter, compound 1 was added to the lithium hexafluorophosphate-containing solution, and stirred to be completely dissolved, thereby obtaining an electrolytic solution of example 1. Wherein, the mass percent of lithium hexafluorophosphate in the electrolyte is 14%, the mass percent of the compound 1 in the electrolyte is 0.5%, and the mass percent of the mixed solvent in the electrolyte is 85.5%. The electrolyte formulation is shown in table 1.
Examples 2 to 8
Examples 2 to 8 are also specific examples of the electrolyte preparation, and the parameters and preparation method are the same as those of example 1 except for the parameters shown in Table 1. The electrolyte formulation is shown in table 1.
Comparative examples 1 to 3
Comparative examples 1 to 3 the parameters and preparation method were the same as in example 1 except for the parameters shown in Table 1. The electrolyte formulation is shown in table 1.
TABLE 1 electrolyte compositions of examples 1 to 8 and comparative examples 1 to 3
Figure BDA0002374740130000051
Figure BDA0002374740130000061
Note: the concentration of the lithium salt is the mass percentage content in the electrolyte;
the content of the 4- (trimethylsiloxy) -3-penten-2-one additive is the mass percentage content in the electrolyte;
the proportion of each component in the solvent is mass ratio.
Lithium ion battery performance testing
Preparing a lithium ion battery:
mixing ternary material (LiNi) of positive electrode active material0.5Mn1.5O4) The conductive agent acetylene black and the binder polyvinylidene fluoride (PVDF) are mixed according to the mass ratio of 95.5: 2.5: 2, fully stirring and uniformly mixing in an N-methyl pyrrolidone solvent system, coating on an aluminum foil, drying, and cold pressing to obtain the positive plate. Preparing negative active material artificial graphite, conductive agent acetylene black, binder Styrene Butadiene Rubber (SBR), and thickener carboxymethylcellulose sodium (CMC) according to a mass ratio of 96: 2: 1:1, fully stirring and uniformly mixing in a deionized water solvent system, coating on a copper foil, drying, and cold pressing to obtain the negative plate. Polyethylene (PE) is used as a base film, and a nano aluminum oxide coating is coated on the base film to be used as an isolating film. And (3) sequentially laminating the positive plate, the isolating membrane and the negative plate, winding the positive plate, the isolating membrane and the negative plate along the same direction to obtain a bare cell, placing the bare cell in an outer package, injecting the electrolyte prepared in each embodiment and comparative example, and carrying out procedures of packaging, shelving at 45 ℃, high-temperature clamp formation, secondary packaging, capacity grading and the like to obtain the lithium ion battery, and carrying out battery performance test, wherein the results are shown in table 2. Wherein:
(1) and (3) testing the normal-temperature cycle performance of the battery: and (3) charging the battery after capacity grading to 4.5V at a constant current and a constant voltage of 1C and stopping the current to 0.02C at 25 ℃, then discharging to 3V at a constant current of 1C, and calculating the capacity retention rate of the 100 th cycle after the battery is cycled according to the cycle and the charge/discharge cycles of 100 times. The calculation formula is as follows:
the 100 th cycle capacity retention (%) was (100 th cycle discharge capacity/first cycle discharge capacity) × 100%.
First efficiency (%) — (1 st cycle discharge capacity/first cycle discharge capacity) × 100%.
TABLE 2 results of cell performance test of examples 1 to 8 and comparative examples 1 to 3
Figure BDA0002374740130000062
Figure BDA0002374740130000071
From the results, it can be seen that the addition of the 4- (trimethylsiloxy) -3-penten-2-one derivative to the electrolyte improved Li/LiNi0.5Mn1.5O4Coulombic efficiency and cycle retention of (LNMO) half cells and graphite/LNMO full cells and improved cycling at 4.5V operation.

Claims (8)

1. A4- (trimethylsilyloxy) -3-penten-2-one additive, characterized in that it has the following structural formula:
Figure FDA0002374740120000011
wherein R1, R2 and R3 are respectively selected from substituted or unsubstituted straight-chain alkyl with 1-5 carbon atoms, alkenyl containing five-membered cyclic carbonate, carbonate with part of hydrogen substituted by halogen, phenyl and cyano.
2. The additive of claim 1 wherein the additive of the 4- (trimethylsiloxy) -3-penten-2-one type is selected from at least one of the compounds of the following structural formula:
Figure FDA0002374740120000012
3. the lithium ion battery electrolyte containing the 4- (trimethylsiloxy) -3-penten-2-one additive of claim 1, which is characterized by comprising the following components in percentage by mass in the lithium ion battery electrolyte:
5 to 19 percent of lithium salt
80-94% of organic solvent
0.05-2% of 4- (trimethylsiloxy) -3-pentene-2-one additive.
4. The lithium ion battery electrolyte of claim 3 wherein the lithium salt is selected from at least one of lithium hexafluorophosphate, lithium bis (oxalato) borate, lithium tetrafluoroborate, lithium perchlorate, lithium bis (trifluoromethylsulfonyl) imide, lithium methylsulfonate, and lithium trifluoromethylsulfonate.
5. The lithium ion battery electrolyte of claim 3, wherein the organic solvent is selected from one or more of esters, amines, sulfones, and nitriles.
6. The lithium ion battery electrolyte of claim 5, wherein the esters are selected from at least one of ethylene carbonate, propylene carbonate, butylene carbonate, γ -butyrolactone, dipropyl carbonate, dimethyl sulfite, vinylene carbonate, methyl propyl carbonate, ethyl acetate, methyl butyrate, ethyl butyrate, methyl propionate, ethyl propionate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, propyl acetate; the amine is selected from at least one of N-methylacetamide, N-methylformamide, dimethylformamide and diethylformamide; the sulfones are selected from at least one of dimethyl sulfoxide, sulfolane, diphenyl sulfoxide, thionyl chloride and dipropyl sulfone; the nitrile is at least one of acetonitrile, succinonitrile, adiponitrile and glutaronitrile.
7. The lithium ion battery electrolyte of claim 6 wherein the organic solvent is selected from the group consisting of ethylene carbonate, diethyl carbonate, and ethyl methyl carbonate.
8. The lithium ion battery electrolyte of claim 3, wherein the oxidation potential of the lithium ion battery electrolyte is 4.5-5V.
CN202010061777.4A 2020-01-20 2020-01-20 4- (trimethylsilyloxy) -3-pentene-2-ketone additive and lithium ion battery electrolyte thereof Pending CN111253426A (en)

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Cited By (2)

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CN111668551A (en) * 2020-07-01 2020-09-15 河南电池研究院有限公司 High-temperature high-pressure electrolyte matched with silicon-carbon negative electrode material lithium ion battery
CN112563505A (en) * 2020-12-09 2021-03-26 北京理工大学重庆创新中心 High-nickel anode material capable of resisting corrosion of HF in LiPF 6-based electrolyte and preparation method thereof

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN111668551A (en) * 2020-07-01 2020-09-15 河南电池研究院有限公司 High-temperature high-pressure electrolyte matched with silicon-carbon negative electrode material lithium ion battery
CN112563505A (en) * 2020-12-09 2021-03-26 北京理工大学重庆创新中心 High-nickel anode material capable of resisting corrosion of HF in LiPF 6-based electrolyte and preparation method thereof
CN112563505B (en) * 2020-12-09 2021-10-22 北京理工大学重庆创新中心 High-nickel anode material capable of resisting corrosion of HF in LiPF 6-based electrolyte and preparation method thereof

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Application publication date: 20200609