CN103346351B - A kind of Novel borate solvent for lithium-ion secondary battery - Google Patents
A kind of Novel borate solvent for lithium-ion secondary battery Download PDFInfo
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- CN103346351B CN103346351B CN201310267745.XA CN201310267745A CN103346351B CN 103346351 B CN103346351 B CN 103346351B CN 201310267745 A CN201310267745 A CN 201310267745A CN 103346351 B CN103346351 B CN 103346351B
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- solvent
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- ether
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- 239000002904 solvent Substances 0.000 title claims abstract description 24
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title abstract description 8
- 229910001416 lithium ion Inorganic materials 0.000 title abstract description 8
- 239000003792 electrolyte Substances 0.000 claims abstract description 25
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 claims description 5
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical group [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 claims description 5
- 229910003002 lithium salt Inorganic materials 0.000 claims description 3
- 159000000002 lithium salts Chemical class 0.000 claims description 3
- 239000008151 electrolyte solution Substances 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 abstract description 11
- -1 boric acid ester compound Chemical class 0.000 abstract description 11
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
- 125000001033 ether group Chemical group 0.000 abstract description 4
- 239000003063 flame retardant Substances 0.000 abstract description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000002931 mesocarbon microbead Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 238000005868 electrolysis reaction Methods 0.000 description 4
- 229910052493 LiFePO4 Inorganic materials 0.000 description 3
- 229910002097 Lithium manganese(III,IV) oxide Inorganic materials 0.000 description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- 229910001290 LiPF6 Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- WKFDWSVVMAKCDI-UHFFFAOYSA-N C(C=1C(C(=O)OCC)=CC=CC1)(=O)OCC.[C] Chemical compound C(C=1C(C(=O)OCC)=CC=CC1)(=O)OCC.[C] WKFDWSVVMAKCDI-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910013188 LiBOB Inorganic materials 0.000 description 1
- 229910010710 LiFePO Inorganic materials 0.000 description 1
- 229910015645 LiMn Inorganic materials 0.000 description 1
- 150000001485 argon Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011244 liquid electrolyte Substances 0.000 description 1
- 229910001540 lithium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Secondary Cells (AREA)
Abstract
The invention discloses a kind of novel dissolvent that can be used for lithium secondary cell electrolyte, the architectural feature of described solvent is the substituted boric acid ester compound of ether chain, and its skeleton symbol is R1OB(OR2) OR3, R in formula1、R2And R3Can be that monoether chain replaces, it is also possible to be double or three ether chains are substituted.Wherein, substituent R1、R2Or R3Ether chain in can contain aryl, haloalkyl, halogenated aryl, wherein: halogen is F, Cl or Br, and halo is partly or entirely to replace.Use and can automatically eliminate the moisture in electrolyte containing described borate solvent, reduce the moisture impact on battery performance；It addition, the product diboron trioxide of burning can be attached to electrode surface, there is the ability that solid-state is fire-retardant；And performance such as specific capacity, the cyclicity etc. of lithium ion battery are affected less by this solvent.
Description
Technical field
The present invention relates to a kind of secondary lithium batteries novel dissolvent.More particularly to a kind of borate ester containing ether chain
Compound is the electrolyte of solvent, belongs to electrochemistry and the technical field of electrochmical power source product.
Background technology
Lithium ion battery has the advantage of high-energy-density, long-life and environmental protection, ties up to alleviate the energy as storage bodies
Problem and environmental problem play very important effect.At present, lithium ion battery mainly uses liquid electrolyte as electrolysis
Matter.Wherein, solvent is the important component part of electrolyte.Solvent mainly uses low melting point, low viscous linear carbonate (carbonic acid
Dimethyl ester, diethyl carbonate and Ethyl methyl carbonate) and the cyclic carbonate (ethylene carbonate, Allyl carbonate) of high-k
Mixed solvent.Carbonic ester electrolyte has wider operating temperature range, high electrical conductivity and the excellent electrification to electrode material
Learn compatibility.But, organic carbonate solvents flash-point is low, there is the most incendive safety issue, limits lithium-ion electric
The large-scale application in pond.Therefore, the important directions that safety electrolyte is development lithium ion battery is found.
Boric acid ester compound has self and eliminates the characteristic of moisture, it is possible to reduce the moisture impact on battery performance；And
And the product diboron trioxide after boric acid ester compound burning can be attached to electrode material surface, isolation connects with air
Touch, there is the ability that solid-state is fire-retardant.Therefore, boric acid ester compound can improve to a certain extent as the solvent of electrolyte
The safety of electrolyte.
Summary of the invention
The technical problem to be solved is to provide a kind of novel secondary lithium batteries solvent.
The purpose of the present invention is achieved through the following technical solutions: a kind of secondary lithium batteries solvent, it is containing ether chain
Boric acid ester compound, structural formula is:
R in formula1、R2And R3Can be that monoether chain replaces, it is also possible to be double or three ether chains are substituted.Wherein, substituent R1、R2
Or R3Ether chain in can contain aryl, haloalkyl, halogenated aryl, wherein: halogen is F, Cl or Br, and halo is for partly or entirely to take
Generation.
The solvent form of the present invention is liquid.
By the boric acid ester compound containing ether chain above-mentioned for the present invention, individually or mixing is used as lithium rechargeable battery electricity
Solve the solvent in liquid.If be used in mixed way, in electrolyte, other solvents can be selected for linear carbonate (dimethyl carbonate DMC, carbon
Diethyl phthalate DEC, Ethyl methyl carbonate EMC etc.) and cyclic carbonate (ethylene carbonate EC, Allyl carbonate PC, gamma-butyrolacton
GBL etc.) in one or more.Solvent can be extended to ether solvent such as glycol dimethyl ether DME, 1,3-dioxolane
DOL and tetrahydrofuran THF etc..Available lithium salts is LiClO4、LiBF4、LiPF6、LiAsF6, in LiBOB and LiTFSI extremely
Few one, the concentration of lithium salts is 0.5-2M.
The present invention evaluation to lithium secondary battery charge-discharge performance: use the electrolyte group respectively that solvent described above is prepared
Fill 2016 button cells: MCMB/Li, LiFePO4/ Li, LiMn2O4/Li。
The beneficial effects of the present invention is: the electrolyte of the solvent containing the present invention has self except the character of water, reduces
The moisture impact on battery performance；It addition, the product diboron trioxide of burning can be attached to electrode surface, there is solid-state fire-retardant
Ability；And performance such as specific capacity, the cyclicity etc. of lithium ion battery are affected less by this solvent.
Accompanying drawing explanation
Accompanying drawing 1: the structure chart of boric acid ester compound used by the present invention.
Accompanying drawing 2: embodiment of the present invention 2-4 and comparative example 1 use containing described three (ethyoxyl ethylene) borate
The charge-discharge performance figure of the button cell that the electrolyte of solvent and blank electrolysis liquid assemble.
Accompanying drawing 3: the embodiment of the present invention 2 MCMB electrode is at three (ethyoxyl ethylene) borate containing film for additive
Cyclic voltammetry curve in the electrolyte of solvent.
Detailed description of the invention
Below in conjunction with embodiment and accompanying drawing, the invention will be further described, but these embodiments are not constituted the present invention
Any restriction.
Embodiment 1
Borate ester solvent of the present invention is used to prepare electrolyte, the lithium used in the glove box of full argon
Salt be LiTFSI, LiTFSI concentration in the electrolytic solution be 1M, the boric acid ester compound used is three (ethyoxyl ethylenes)
Borate, concrete structure is as follows:
Embodiment 2
In the glove box of full argon, assemble MCMB/Li 2016 button cell, use novel dissolvent described in embodiment 1
The electrolyte of preparation, charging/discharging voltage interval is 0～3 V, and electric current density is 40 mA/g.Test result is from accompanying drawing 2, right
In MCMB negative pole, first week charge specific capacity be 296 mAh/g(head week coulombic efficiencies be 63%), circulate charge specific capacity after 100 weeks
Being 181 mAh/g, capability retention is 61%.MCMB electrode at the electrolyte of the novel dissolvent preparation used with real in contrast
The performance executed in the blank electrolysis liquid of example 1 is compared, and difference is relatively big, illustrate to use electrolyte anticathode double of described novel dissolvent
Capacitive is poor.But from accompanying drawing 3 it will be seen that the circulation the described borate electrolyte containing film for additive of the MCMB electrode
Volt-ampere stability is preferable, illustrates that MCMB electrode performance in described novel dissolvent electrolyte has greatly improved space.
Embodiment 3
LiFePO is assembled in the glove box of full argon4/ Li 2016 button cell, uses described in embodiment 1 novel molten
The electrolyte of agent preparation, charging/discharging voltage interval is 3～4 V, and electric current density is 40 mA/g.Test result from accompanying drawing 3,
For LiFePO4Positive pole, first week specific discharge capacity be 103 mAh/g(head week coulombic efficiencies be 74%), discharge after circulating 100 weeks
Specific capacity is 107 mAh/g, and capacity is not the most decayed, but capacity is the most on the low side, illustrates to use the preparation of described novel dissolvent
Electrolyte is to LiFePO4The performance of positive pole has a certain impact.
Embodiment 4
LiMn is assembled in the glove box of full argon2O4/ Li 2016 button cell, uses described in embodiment 1 novel molten
The electrolyte of agent preparation, charging/discharging voltage interval is 3～4.3 V, and electric current density is 40 mA/g.As it is clear from fig. 2 that for
LiMn2O4Positive pole, first week specific discharge capacity be 109 mAh/g(head week coulombic efficiencies be 95%), circulate capability retention after 100 weeks
It is 86%, illustrates that the electrolyte using the preparation of described novel dissolvent is to LiMn2O4The performance impact of positive pole is less.
Embodiment 5
Selected novel dissolvent is R in the structure shown in accompanying drawing 11、R2And R3It is ethyoxyl ethylene group
(EtOCH2CH2-) substituted boric acid ester compound, i.e. three (ethyoxyl ethylene) borate, as follows:
The synthetic route of three (ethyoxyl ethylene) borate is as follows:
Using method prepared by classical borate, boric acid reacts with corresponding alcohol, is azeotroped off instead for solvent with toluene
The water generated during Ying, the extent of reaction is high.
Experimental procedure: add 24.7 g (0.4 mol) boric acid, 126 g (1.4 mol) second in 250 mL single port flasks
2-ethoxyethanol and 150 mL toluene, be placed in oil bath pan, install oil water separator successively, oil water separator is installed ball-type cold
Solidifying pipe and oil bubbler, pour part toluene in oil water separator.It is heated to 120 DEG C to be back in oil water separator no longer to have
The stopped reaction when globule drips, steams toluene, and the decompression distillation of remaining liq oil pump obtains 74-80 DEG C of (< 3.5 mmHg) fraction
93.9 g, yield is 84.4%.Product warp1H NMR nuclear-magnetism is identified.1H NMR (300 MHz, CDCl3) δ/ppm: 3.94
(t, 6H, -OCH2CH2O-), 3.49-3.55 (m, 12H, -CH2OCH2-), 1.20 (t, 9H, -CH2CH3)。
Comparative example 1
In the glove box of full argon, assemble MCMB/Li 2016 button cell, use 1mol/L LiPF6 DMC/EC/
EMC 1:1:1(volume ratio) it is blank electrolysis liquid, charging/discharging voltage interval is 0～3 V, and electric current density is 40 mA/g.
Claims (1)
1. a lithium secondary cell electrolyte, it is characterised in that the lithium salts used in described electrolyte is LiTFSI, LiTFSI
Concentration in the electrolytic solution is 1M, and the solvent used is three (ethyoxyl ethylene) borate, and concrete structure is as follows:
。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310267745.XA CN103346351B (en) | 2013-06-28 | 2013-06-28 | A kind of Novel borate solvent for lithium-ion secondary battery |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310267745.XA CN103346351B (en) | 2013-06-28 | 2013-06-28 | A kind of Novel borate solvent for lithium-ion secondary battery |
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| CN103346351A CN103346351A (en) | 2013-10-09 |
| CN103346351B true CN103346351B (en) | 2016-12-28 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105655633A (en) * | 2016-03-30 | 2016-06-08 | 龙能科技（苏州）有限责任公司 | Lithium ion battery electrolyte suitable for lithium titanate battery |
| CN108822172A (en) * | 2018-08-29 | 2018-11-16 | 上海兆维科技发展有限公司 | The novel processing step of 5 '-DMTr-2 '-EOE- thymus gland pyridine nucleosides of nucleosides modifier |
| CN109980287B (en) * | 2019-04-04 | 2021-10-19 | 常州创标新能源科技有限公司 | Electrolyte for lithium battery and preparation method thereof |
| CN111883845A (en) * | 2020-08-27 | 2020-11-03 | 湖北亿纬动力有限公司 | Electrolyte for lithium battery, lithium battery and application of bisborate solvent |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW432733B (en) * | 1997-10-02 | 2001-05-01 | Basf Ag | Esters as solvents in electrolyte systems for Li-ion storage cells |
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| WO2009153052A1 (en) * | 2008-06-20 | 2009-12-23 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | A non-aqueous electrolyte containing as a solvent a borate ester and/or an aluminate ester |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW432733B (en) * | 1997-10-02 | 2001-05-01 | Basf Ag | Esters as solvents in electrolyte systems for Li-ion storage cells |
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