CN103904363A - Phosphite ester stabilizer and non-aqueous electrolyte comprising stabilizer - Google Patents
Phosphite ester stabilizer and non-aqueous electrolyte comprising stabilizer Download PDFInfo
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- CN103904363A CN103904363A CN201210585505.XA CN201210585505A CN103904363A CN 103904363 A CN103904363 A CN 103904363A CN 201210585505 A CN201210585505 A CN 201210585505A CN 103904363 A CN103904363 A CN 103904363A
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- CN
- China
- Prior art keywords
- acid esters
- phosphorous acid
- stabilizer
- electrolytic solution
- phenyl
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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
-
- 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
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic 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
Abstract
The invention provides a phosphite ester stabilizer applicable to a non-aqueous electrolyte and the non-aqueous electrolyte comprising the stabilizer. The non-aqueous electrolyte comprises lithium salt, carbonic ester organic solvents, conventional additives and the phosphite ester stabilizer; the addition amount of the phosphite ester stabilizer in the non-aqueous electrolyte is 100ppm-1000ppm.
Description
Technical field
The present invention relates to nonaqueous electrolytic solution technical field, the nonaqueous electrolytic solution that particularly relates to a kind of phosphorous acid esters stabilizer and contain this phosphorous acid esters stabilizer.
Background technology
Because lithium ion battery has that energy density is high, specific power is large, good cycle, memory-less effect, the feature such as pollution-free, be used in widely in digital product at present, be also the ideal chose of following electric automobile energy simultaneously.
As electrolytical lithium hexafluoro phosphate (LiPF
6), its thermal stability is poor, easily resolves into phosphorus pentafluoride (PF
5), phosphorus pentafluoride existence can cause the polymerization of proton solvent impurity etc. in ethylene carbonate, dimethyl carbonate or electrolyte, generate solubility list polymers, dimer, oligomer, along with the increase of conjugated system in polymer, polymer spectral red shift appearss as color base group, causes electrolyte colourity to increase.Along with the increase of the degree of polymerization, electrolyte color is more and more darker.Phosphite ester compound has reproducibility, can be used as antioxidant is applied in lithium-ion battery electrolytes, infer that the mechanism of action of phosphite ester compound in lithium-ion battery electrolytes is as follows: phosphite ester compound acts on the solvent polymeric reaction under phosphorus pentafluoride catalysis, chain polymerization process capable of blocking, phosphorus pentafluoride was lost efficacy to the catalytic action of polymerization reaction, thereby stablized the colourity of electrolyte.
The stabilizer using in nonaqueous electrolytic solution is at present mainly the phosphorous acid esters of molecular weight, although this type of stabilizer can play stabilization, the smell is awful for the electrolyte that but its boiling point is low, volatility causes more greatly this class stabilizer, owing to having certain toxicity, larger to human injury.
Summary of the invention
Based on this, the invention provides the phosphorous acid esters stabilizer that a kind of performance is more stable and the nonaqueous electrolytic solution that contains this phosphorous acid esters stabilizer.
A kind of phosphorous acid esters stabilizer, for nonaqueous electrolytic solution, this phosphorous acid esters stabilizer is a kind of in the compound that represents of general formula (1) or (2) or multiple mixture wherein:
R in (1) formula of being somebody's turn to do
1, R
2, R
3for carbon number is C
16～C
20alkyl, aromatic radical; Alkyl is selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or its isomers and fluoro thing; Aromatic radical is selected from three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl, or its isomers and fluoro thing.
(2) in formula, R4, R5 are that carbon number is C
16～C
20alkyl, aromatic radical; Alkyl is selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or its isomers and fluoro thing; Aromatic radical is selected from three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl, or its isomers and fluoro thing.
A kind of nonaqueous electrolytic solution that contains phosphorous acid esters stabilizer, this nonaqueous electrolytic solution contains lithium salts, carbonates organic solvent, conventional additives and phosphorous acid esters stabilizer, and this phosphorous acid esters stabilizer is a kind of in the compound that represents of general formula (1) or (2) or multiple mixture wherein:
R in (1) formula of being somebody's turn to do
1, R
2, R
3for carbon number is C
16～C
20alkyl, aromatic radical; Alkyl is selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or its isomers and fluoro thing; Aromatic radical is selected from three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl, or its isomers and fluoro thing.
(2) in formula, R4, R5 are that carbon number is C
16～C
20alkyl, aromatic radical; Alkyl is selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or its isomers and fluoro thing; Aromatic radical is selected from three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl, or its isomers and fluoro thing.
Further, the percentage by weight 8.0%～20.0% of described lithium salts, the percentage by weight of carbonates organic solvent is 83.0%～91.0%, the percentage by weight of conventional additives is 1.0%～5.0%.
Further, the percentage by weight 10%～13% of described lithium salts, the percentage by weight of carbonates organic solvent is 85.5%～89%, the percentage by weight of conventional additives is 1.0%～4.0%
Further, described phosphorous acid esters stabilizer is 100ppm～1000ppm(ppm at the addition of nonaqueous electrolytic solution).
Further, described phosphorous acid esters stabilizer is 100ppm～300ppm(ppm at the addition of nonaqueous electrolytic solution).
Further, described lithium salts is selected from one or more in lithium hexafluoro phosphate, LiBF4, dioxalic acid lithium borate, two fluoroform sulfimide lithium.
In addition, described phosphorous acid esters stabilizer has larger molecular weight and lower volatility, it has more significantly stable and effect, has improved the ability of battery normal temperature circulation, has solved the current low-molecular-weight phosphite ester electrolyte problem that the smell is awful simultaneously.
Brief description of the drawings
Fig. 1 is the GC-MS(gas chromatograph-mass spectrometer (GC-MS) analysis of triphenyl phosphite stabilizer in phosphorous acid esters stabilizer of the present invention and comparative example) comparison diagram.
Fig. 2 is nonaqueous electrolytic solution and the comparative example electrolyte normal temperature circulation comparison diagram that the present invention contains phosphorous acid esters stabilizer.
Embodiment
For further understanding feature of the present invention, technological means and the specific purposes that reach, function, resolve the advantages and spirit of the present invention, by below in conjunction with accompanying drawing and embodiment, detailed description of the present invention being further understood.
The phosphorous acid esters stabilizer of nonaqueous electrolytic solution of the present invention is a kind of in the compound that represents of general formula (1) or (2) or multiple mixture wherein:
(1) R in formula
1, R
2, R
3for carbon number is C
16～C
20alkyl, aromatic radical, R
1, R
2, R
3can be identical can be not identical yet; Alkyl can be selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl or its isomers and halides one to three kind; Aromatic radical can select three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl or its isomers and halides one to three kind.The phosphite ester preferably with (1) structure is: tricresyl phosphite (octadecyl) ester, three (2,4,6-tri-tert phenyl) phosphite ester.
(2) in formula, R4, R5 are that carbon number is C
16～C
20alkyl, aromatic radical, R4, R5 can be identical can be not identical yet; Alkyl can be selected from one or both of cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl or its isomers and halides; Aromatic radical can select one or both of three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl or its isomers and halides.The phosphite ester preferably with (2) formula is: distearyl pentaerythritol diphosphite, two (2,4,6-tri-tert phenyl) pentaerythritol diphosphites.
Nonaqueous electrolytic solution of the present invention comprises lithium salts, carbonates organic solvent, conventional additives and described phosphorous acid esters stabilizer, the percentage by weight 8.0%～20.0% of described lithium salts, the percentage by weight of carbonates organic solvent is 83.0%～91.0%, and the percentage by weight of conventional additives is 1.0%～5.0%.Further, the percentage by weight 10%～13% of described lithium salts, the percentage by weight of carbonates organic solvent is 85.5%～89%, the percentage by weight of conventional additives is 1.0%～4.0%.
When described phosphorous acid esters stabilizer addition is lower than 100ppm(ppm) time, stablize the DeGrain of colourity, and during higher than 1000ppm, may cause stabilizer dissolve slowly or can not dissolve completely.Therefore the addition of described phosphorous acid esters stabilizer in nonaqueous electrolytic solution is 100ppm～1000ppm, and preferably addition is 100ppm～300ppm.
Described lithium salts can be selected from one or more in lithium hexafluoro phosphate, LiBF4, dioxalic acid lithium borate, two fluoroform sulfimide lithium; Described carbonates organic solvent be selected from (MA) in ethylene carbonate (EC), dimethyl carbonate (DMC), diethyl carbonate (DEC), methyl ethyl carbonate (EMC), propene carbonate (PC), methyl propyl carbonate (MPC), ethyl acetate two or three; Described conventional additives is selected from carbonic acid sub-ethene (VC), fluorinated ethylene carbonate (FEC), 1, one or more in 3-propane sultone (1,3-PS), Isosorbide-5-Nitrae-butane sultones (Isosorbide-5-Nitrae-BS).
Above-mentioned phosphorous acid esters stabilizer, lithium salts, carbonates organic solvent, conventional additives are obtained to nonaqueous electrolytic solution of the present invention after stirring.
For more clearly expressing the performance of nonaqueous electrolytic solution of the present invention and phosphorous acid esters stabilizer thereof, do following experiment and measure, wherein sample 1-1,1-2,1-3 are contrast sample, other samples are the invention process sample, prepare as table 1:
Table 1
Prepare sample according to table 1, ethylene carbonate (EC), dimethyl carbonate (DMC), methyl ethyl carbonate (EMC), vinylene carbonate (VC) are mixed and made, more slowly add lithium hexafluoro phosphate and dissolve completely in mixed solvent.Finally taking electrolyte weight as benchmark, to the phosphorous acid esters stabilizer that adds 100ppm of the present invention, 200ppm, 300ppm in electrolyte, finally obtain contrasting sample and implement sample.Wherein sample 4-1～4-3 is tricresyl phosphite (octadecyl) ester with two (2,4,6-tri-tert phenyl) pentaerythritol diphosphites according to the stable composition additive of weight ratio 1:1.
Experiment 1:
Contrast sample 1-1 and enforcement sample 2-1 stabilizer sealing used are deposited, extract the gas of stabilizer top, adopt gas chromatograph-mass spectrometer (GC-MS) test gas composition, in analytical gas mass spectrogram, whether there is stabilizer peak, and judgement contains the volatile size of stabilizer according to peak area, test result as shown in Figure 1.As shown in Figure 1, also there is phenol peak except detecting nitrogen peak in contrast sample 1-1, and this phenol peak is decomposed and obtained by triphenyl phosphite, and the invention process sample 2-1 only detects nitrogen peak, and free from extraneous odour.
Experiment 2:
To contrast sample and implement sample glass transparent seal of vessel used for electrolyte, being placed in normal temperature illumination deposits and ensures that the illumination condition of each sample is consistent, test at set intervals its change color, change color adopts GB GB/T3143-1982 liquid chemical colour measurement method (Hazen unit-platinum-cobalt look number) to measure.Test result is as shown in table 2:
Table 2
As can be seen from Table 2, compared with triphenyl phosphite stabilizer contrast sample, contain stabilizer of the present invention and keeping thering is obvious advantage aspect nonaqueous electrolytic solution colour stable.
Experiment 3:
Carrying out the test of normal temperature charge and discharge cycles containing the different electrolyte injection battery cores that have different stabilizers and variable concentrations, test battery adopts lithium cobaltate cathode, the aluminum hull battery core of graphite cathode material and polypropylene diaphragm composition is carried out cycle charge-discharge contrast test, and test result as shown in Figure 2.The circulation volume conservation rate that contains as can be seen from Figure 2 stabilizer of the present invention obviously promotes, and the cycle performance of battery is improved.
It should be noted that; for the person of ordinary skill of the art; without departing from the inventive concept of the premise; identical or similar component and formula described in employing the above embodiment of the present invention; or same or analogous method described in employing and the embodiment of the present invention; other phosphorous acid esters stabilizers that obtain and the nonaqueous electrolytic solution that contains this phosphorous acid esters stabilizer, these all belong to protection scope of the present invention.Therefore, the protection range of patent of the present invention should be as the criterion with claims.
Claims (7)
1. a phosphorous acid esters stabilizer, for nonaqueous electrolytic solution, is characterized in that, this phosphorous acid esters stabilizer is a kind of in the compound that represents of general formula (1) or (2) or multiple mixture wherein:
R in (1) formula of being somebody's turn to do
1, R
2, R
3for carbon number is C
16～C
20alkyl, aromatic radical; Alkyl is selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or its isomers and fluoro thing; Aromatic radical is selected from three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl, or its isomers and fluoro thing.
(2) R in formula
4, R
5for carbon number is C
16～C
20alkyl, aromatic radical; Alkyl is selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or its isomers and fluoro thing; Aromatic radical is selected from three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl, or its isomers and fluoro thing.
2. a nonaqueous electrolytic solution that contains phosphorous acid esters stabilizer, it is characterized in that, this nonaqueous electrolytic solution contains lithium salts, carbonates organic solvent, conventional additives and phosphorous acid esters stabilizer, and this phosphorous acid esters stabilizer is a kind of in the compound that represents of general formula (1) or (2) or multiple mixture wherein:
R in (1) formula of being somebody's turn to do
1, R
2, R
3for carbon number is C
16～C
20alkyl, aromatic radical; Alkyl is selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or its isomers and fluoro thing; Aromatic radical is selected from three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl, or its isomers and fluoro thing.
(2) in formula, R4, R5 are that carbon number is C
16～C
20alkyl, aromatic radical; Alkyl is selected from cetyl, heptadecyl, octadecyl, nonadecyl, eicosyl, or its isomers and fluoro thing; Aromatic radical is selected from three n-butylphenyl, three secondary butyl phenenyls, triisobutyl phenyl, tri-tert phenyl, three neopentyl phenyl, or its isomers and fluoro thing.
3. the nonaqueous electrolytic solution that contains phosphorous acid esters stabilizer according to claim 2, it is characterized in that, the percentage by weight 8.0%～20.0% of described lithium salts, the percentage by weight of carbonates organic solvent is 83.0%～91.0%, the percentage by weight of conventional additives is 1.0%～5.0%.
4. the nonaqueous electrolytic solution that contains phosphorous acid esters stabilizer according to claim 2, it is characterized in that, the percentage by weight 10%～13% of described lithium salts, the percentage by weight of carbonates organic solvent is 85.5%～89%, the percentage by weight of conventional additives is 1.0%～4.0%.
5. according to the nonaqueous electrolytic solution that contains phosphorous acid esters stabilizer described in any one in claim 2 to 4, it is characterized in that, described phosphorous acid esters stabilizer is 100ppm～1000ppm at the addition of nonaqueous electrolytic solution.
6. according to the nonaqueous electrolytic solution that contains phosphorous acid esters stabilizer described in any one in claim 2 to 4, it is characterized in that, described phosphorous acid esters stabilizer is 100ppm～300ppm at the addition of nonaqueous electrolytic solution.
7. the nonaqueous electrolytic solution that contains phosphorous acid esters stabilizer according to claim 2, is characterized in that, described lithium salts is selected from one or more in lithium hexafluoro phosphate, LiBF4, dioxalic acid lithium borate, two fluoroform sulfimide lithium.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210585505.XA CN103904363A (en) | 2012-12-28 | 2012-12-28 | Phosphite ester stabilizer and non-aqueous electrolyte comprising stabilizer |
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|---|---|---|---|
| CN201210585505.XA CN103904363A (en) | 2012-12-28 | 2012-12-28 | Phosphite ester stabilizer and non-aqueous electrolyte comprising stabilizer |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016095116A1 (en) * | 2014-12-17 | 2016-06-23 | Basf Corporation | Electrolyte compositions for rechargeable lithium ion batteries |
| CN105895954A (en) * | 2016-05-05 | 2016-08-24 | 东莞市凯欣电池材料有限公司 | High-stability power battery electrolyte |
| CN107171022A (en) * | 2017-06-14 | 2017-09-15 | 厦门首能科技有限公司 | A kind of lithium-ion electrolyte and its lithium ion battery |
| CN109546218A (en) * | 2018-12-19 | 2019-03-29 | 珠海光宇电池有限公司 | A kind of silicon-carbon lithium-ion battery electrolytes and the silicon-carbon lithium ion battery using the electrolyte |
| EP3993129A1 (en) * | 2020-11-03 | 2022-05-04 | SK Innovation Co., Ltd. | Electrolyte solution for lithium secondary battery and lithium secondary battery including the same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS593871A (en) * | 1982-06-29 | 1984-01-10 | Showa Denko Kk | Battery |
| CN101405912A (en) * | 2006-03-22 | 2009-04-08 | 费罗公司 | Stabilized nonaqueous electrolytes for rechargeable batteries |
| CN102326287A (en) * | 2009-12-29 | 2012-01-18 | 索尼公司 | Nonaqueous electrolyte and nonaqueous electrolyte battery |
-
2012
- 2012-12-28 CN CN201210585505.XA patent/CN103904363A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS593871A (en) * | 1982-06-29 | 1984-01-10 | Showa Denko Kk | Battery |
| CN101405912A (en) * | 2006-03-22 | 2009-04-08 | 费罗公司 | Stabilized nonaqueous electrolytes for rechargeable batteries |
| CN102326287A (en) * | 2009-12-29 | 2012-01-18 | 索尼公司 | Nonaqueous electrolyte and nonaqueous electrolyte battery |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016095116A1 (en) * | 2014-12-17 | 2016-06-23 | Basf Corporation | Electrolyte compositions for rechargeable lithium ion batteries |
| CN105895954A (en) * | 2016-05-05 | 2016-08-24 | 东莞市凯欣电池材料有限公司 | High-stability power battery electrolyte |
| CN107171022A (en) * | 2017-06-14 | 2017-09-15 | 厦门首能科技有限公司 | A kind of lithium-ion electrolyte and its lithium ion battery |
| CN109546218A (en) * | 2018-12-19 | 2019-03-29 | 珠海光宇电池有限公司 | A kind of silicon-carbon lithium-ion battery electrolytes and the silicon-carbon lithium ion battery using the electrolyte |
| EP3993129A1 (en) * | 2020-11-03 | 2022-05-04 | SK Innovation Co., Ltd. | Electrolyte solution for lithium secondary battery and lithium secondary battery including the same |
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Application publication date: 20140702 |