CN103236561B - Method for detecting alkylsilazane compounds in lithium hexafluorophosphate electrolyte - Google Patents
Method for detecting alkylsilazane compounds in lithium hexafluorophosphate electrolyte Download PDFInfo
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- CN103236561B CN103236561B CN201310107432.8A CN201310107432A CN103236561B CN 103236561 B CN103236561 B CN 103236561B CN 201310107432 A CN201310107432 A CN 201310107432A CN 103236561 B CN103236561 B CN 103236561B
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- lithium hexafluorophosphate
- electrolyte solution
- hexafluorophosphate electrolyte
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- lithium
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- -1 lithium hexafluorophosphate Chemical compound 0.000 title claims abstract description 61
- 239000003792 electrolyte Substances 0.000 title abstract description 22
- 238000000034 method Methods 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 238000001514 detection method Methods 0.000 claims abstract description 25
- 239000008151 electrolyte solution Substances 0.000 claims description 30
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 15
- 238000004451 qualitative analysis Methods 0.000 claims description 8
- ZSMNRKGGHXLZEC-UHFFFAOYSA-N n,n-bis(trimethylsilyl)methanamine Chemical compound C[Si](C)(C)N(C)[Si](C)(C)C ZSMNRKGGHXLZEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 22
- 229910052744 lithium Inorganic materials 0.000 abstract description 22
- 239000000654 additive Substances 0.000 abstract description 8
- 238000003908 quality control method Methods 0.000 abstract description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 35
- 238000003756 stirring Methods 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 229910003002 lithium salt Inorganic materials 0.000 description 7
- 159000000002 lithium salts Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- 229910013872 LiPF Inorganic materials 0.000 description 5
- 101150058243 Lipf gene Proteins 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 229910013870 LiPF 6 Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 229910013063 LiBF 4 Inorganic materials 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910001416 lithium ion 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
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- 229940029985 mineral supplement Drugs 0.000 description 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 239000005486 organic electrolyte Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 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
Abstract
The invention relates to the technical field of the detection of a lithium battery electrolyte, and concretely relates to a method for detecting the alkylsilazane compounds in a lithium hexafluorophosphate electrolyte. A GC-MS instrument is utilized to qualitatively analyze the gas components in the lithium hexafluorophosphate electrolyte in order to inversely conjecture that whether the alkylsilazane compounds are added in the lithium hexafluorophosphate electrolyte or not, so a new detection way is provided for the determination of a case that whether tiny amounts of additives of the above kind are used or not. The method has the advantages of fast and simple operation, good operationality and good practicality, and is of great significance to the quality control of lithium battery products and the control of suppliers.
Description
Technical field
The present invention relates to the detection technique field of lithium battery electrolytes, be specifically related to the detection method of alkyl silicon azane compounds in a kind of lithium hexafluorophosphate electrolyte solution.
Background technology
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 widely used at present in electronic digital product, be also the ideal chose of following electric automobile energy simultaneously.
Lithium battery electrolytes is generally made up of organic solvent and electrolyte (lithium salts).Electrolyte conventional at present has lithium perchlorate (LiClO
4), lithium hexafluoro phosphate (LiPF
6), LiBF4 (LiBF
4) etc., wherein lithium hexafluoro phosphate has good conductivity and electrochemical stability, and thus, lithium hexafluorophosphate electrolyte solution is the lithium battery electrolytes of current main flow.But also there is following defect in lithium hexafluoro phosphate: the first, thermal stability is poor, easily resolves into PF
5, PF
5existence can cause the polymerization of proton solvent impurity etc. in organic solvent ethylene carbonate, dimethyl carbonate or electrolyte, generate solubility list polymers, dimer, oligomer, along with the increase of conjugated system in polymer, polymer spectra red shift manifests color forming group, causes electrolyte colourity to increase; The second, to moisture and hydrofluoric acid (HF) sensitivity, easily there is decomposition reaction: LiPF
6+ H
2o → POF
3+ 2HF+LiF.
Some additive can be added on a small quantity to improve the performance of lithium battery in electrolyte.Such as, the trace impurity comprised in electrolyte, then affects huge for electrical property, and moisture is wherein a kind of common and important objectionable impurities, in order to suppress the moisture in electrolyte, usually adding a small amount of alkyl silicon azane compounds and suppressing as additive.Such as, common alkyl silicon azane compounds, as hexamethyldisiloxane and heptamethyldisilazane, utilizes the reaction of alkyl silicon azane compounds and moisture to eliminate water.But the performance of use amount to lithium battery product of silazane class additive is most important, thus, lithium battery manufacturer needs by detecting silazane class additive, thus realizes the quality control to lithium battery product.
In prior art, gas-chromatography is mostly adopted directly to detect the additive alkyl silicon azane compounds in sampling electrolyte, to judge the quality of lithium battery product.But, alkyl silicon azane compounds is due to addition extremely pettiness, usually in PPM rank, consume with reaction of moisture again after adding, its content is in the electrolytic solution greatly reduced, add the interference of other organic solvent or additive, make to be undertaken detecting by traditional gas-chromatography very difficult, detection time is long, be difficult to judge exactly whether to have in electrolyte added alkyl silicon azane compounds, and directly detection is carried out to sampling electrolyte and can cause corrosion to chromatographic column, add detection maintenance cost, thus the operability of the method and practicality poor, be unfavorable for that manufacturer and supplier are to the quality control of lithium battery product.
Summary of the invention
The object of the invention is to avoid weak point of the prior art and provide a kind of simple to operate fast, the detection method of alkyl silicon azane compounds in the high lithium hexafluorophosphate electrolyte solution of accuracy.
Object of the present invention is achieved through the following technical solutions:
The detection method of alkyl silicon azane compounds in a kind of lithium hexafluorophosphate electrolyte solution is provided, comprises the following steps:
Comprise the following steps:
1) sealing is preserved:
By lithium hexafluorophosphate electrolyte solution sample sealed storage in container, and make the volume of in closed container reserved 1/4 ~ 1/5 to hold escaping gas, 1 ~ 15 day standing time, the liquid phase in container is fully balanced;
2) gas chromatograph-mass spectrometer qualitative analysis:
Escaping gas in container is sampled, then carries out qualitative analysis with the gas ingredients of gas chromatograph-mass spectrometer to institute's sample drawing, confirm in lithium hexafluorophosphate electrolyte solution, whether to add alkyl silicon azane compounds.
Preferably, in described lithium hexafluorophosphate electrolyte solution, the detection addition of alkyl silicon azane compounds is 1 ~ 1000ppm.
Preferably, described alkyl silicon azane compounds is hexamethyldisiloxane or heptamethyldisilazane.
Preferably, in described step 1), standing time is 3 ~ 10 days.
detection side's ratio juris of the present invention is as follows:
In lithium hexafluorophosphate electrolyte solution, always there is the hydrofluoric acid of some, this is due to electrolyte lithium salt lithium hexafluoro phosphate (LiPF
6) and electrolyte in the reaction of impurity minor amount of water that contains, reaction equation is as follows:
If with the addition of alkyl silicon azane compounds in lithium hexafluorophosphate electrolyte solution, with hexamethyldisiloxane ([(CH
3)
3si]
2nH) be example, its reaction equation eliminating water is as follows:
The silanol ((CH that above-mentioned course of reaction generates
3)
3siOH), at H
+and F
-existence under, there is condensation reaction and substitution reaction, generate hexamethyldisiloxane ([(CH
3)
3si]
2and Trimethlyfluorosilane ((CH O)
3)
3siF), concrete reaction equation is as follows:
Hexamethyldisiloxane ([(the CH generated in above-mentioned course of reaction
3)
3si]
2and Trimethlyfluorosilane ((CH O)
3)
3siF) there is volatility, detected and qualitative analysis by the gas componant of gas chromatograph-mass spectrometer to lithium hexafluorophosphate electrolyte solution, from oppositely to infer lithium hexafluorophosphate electrolyte solution whether added hexamethyldisiloxane ([(CH
3)
3si]
2nH).
In like manner, by gas chromatograph-mass spectrometer, qualitative analysis is carried out to the gas componant in lithium hexafluorophosphate electrolyte solution, oppositely can infer in lithium hexafluorophosphate electrolyte solution the alkyl silicon azane compounds whether adding other.
beneficial effect of the present invention:
The invention provides the new detection method of alkyl silicon azane compounds in lithium hexafluorophosphate electrolyte solution, by gas chromatograph-mass spectrometer, qualitative analysis is carried out to the composition in the escaping gas of lithium hexafluorophosphate electrolyte solution, thus oppositely infer in lithium hexafluorophosphate electrolyte solution whether added alkyl silicon azane compounds, for judging whether this kind of trace mineral supplement is provided new detection means by use.Compared with traditional direct method of electrolyte being carried out to gas chromatographic detection: 1) the present invention analyzes escaping gas composition and avoids Direct Analysis lithium hexafluorophosphate electrolyte solution, thus prevent organic solution containing lithium salts to the corrosion of gas chromatograph-mass spectrometer splitter, reduce the maintenance cost of checkout equipment; 2) for lithium battery manufacturer, the present invention only needs extracting gases sample simply to carry out qualitative detection analysis, whether can judge from testing result fast, legibly in electrolyte containing alkyl silicon azane compounds alkane, and addition all can be detected at the alkyl silicon azane compounds of 1 ~ 1000ppm scope, there is operation simple advantage fast, this new detection method of the present invention has better operability and practicality, and the management and control meaning of this quality control for lithium battery product and supplier is very huge.
Accompanying drawing explanation
Fig. 1 is the gas chromatograph-mass spectrometer testing result figure of volatilization gas in the sample A of comparative example of the present invention.
Fig. 2 is the gas chromatograph-mass spectrometer testing result figure of volatilization gas in the sample A+H6DMS1 of embodiments of the invention 1.
Fig. 3 is the gas chromatograph-mass spectrometer testing result figure of volatilization gas in the sample A+H6DMS2 of embodiments of the invention 2.
Fig. 4 is the gas chromatograph-mass spectrometer testing result figure of volatilization gas in the sample A+H6DMS3 of embodiments of the invention 3.
Fig. 5 is the gas chromatograph-mass spectrometer testing result figure of volatilization gas in the sample A+H6DMS4 of embodiments of the invention 4.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
Following examples are all with the hexamethyldisiloxane ([(CH in alkyl silicon azane compounds
3)
3si]
2nH) as additive.
the lithium hexafluorophosphate electrolyte solution sample of comparative example preparation not containing hexamethyldisiloxane
(moisture < 10ppm in the glove box of inflated with nitrogen, oxygen part < 3ppm) in, take high-purity organic solvent dimethyl carbonate (DMC), account for 85% of total weight, stir the lithium hexafluoro phosphate (LiPF slowly adding 15% for 5 minutes in backward mixed solution
6), stir and namely obtain lithium hexafluorophosphate electrolyte solution sample until lithium salts all dissolves in about 10 minutes, be labeled as sample A.
embodiment 1
(moisture < 10ppm in the glove box of inflated with nitrogen, oxygen part < 3ppm) in, take high-purity organic solvent dimethyl carbonate (DMC), account for 85% of total weight, stir and add stabilizer hexamethyldisiloxane ([(CH in backward mixed solution in 5 minutes
3)
3si]
2nH) 400ppm, stirs after 2 minutes, slowly adds the lithium hexafluoro phosphate (LiPF of 15%
6), stir about 10 minutes until lithium salts all dissolves, be labeled as sample A+H6DMS1.
embodiment 2
(moisture < 10ppm in the glove box of inflated with nitrogen, oxygen part < 3ppm) in, take high-purity organic solvent dimethyl carbonate (DMC), account for 85% of total weight, stir and add stabilizer hexamethyldisiloxane ([(CH in backward mixed solution in 5 minutes
3)
3si]
2nH) 200ppm, stirs after 2 minutes, slowly adds the lithium hexafluoro phosphate (LiPF of 15%
6), stir about 10 minutes until lithium salts all dissolves, be labeled as sample A+H6DMS2.
embodiment 3
(moisture < 10ppm in the glove box of inflated with nitrogen, oxygen part < 3ppm) in, take high-purity organic solvent dimethyl carbonate (DMC), account for 85% of total weight, stir and add stabilizer hexamethyldisiloxane ([(CH in backward mixed solution in 5 minutes
3)
3si]
2nH) 100ppm, stirs after 2 minutes, slowly adds the lithium hexafluoro phosphate (LiPF of 15%
6), stir about 10 minutes until lithium salts all dissolves, be labeled as sample A+H6DMS3.
embodiment 4
(moisture < 10ppm in the glove box of inflated with nitrogen, oxygen part < 3ppm) in, take high-purity organic solvent dimethyl carbonate (DMC), account for 85% of total weight, stir and add stabilizer hexamethyldisiloxane ([(CH in backward mixed solution in 5 minutes
3)
3si]
2nH) 50ppm, stirs after 2 minutes, slowly adds the lithium hexafluoro phosphate (LiPF of 15%
6), stir about 10 minutes until lithium salts all dissolves, be labeled as sample A+H6DMS4.
gas chromatograph-mass spectrometer is adopted to carry out detections analysis to the gas componant in the sample of embodiment 1 to 4 and comparative example respectively:
Respectively by sample A, A+H6DMS1, A+H6DMS2, A+H6DMS3, A+H6DMS4, carry out at normal temperatures being sealed in different containers, and the volume of reserved 1/4 ~ 1/5 holds its escaping gas, store and after 10 days, escaping gas is sampled, then use gas chromatograph-mass spectrometer (CLARUS600 gas chromatograph-mass spectrometer) composition to volatilization gas in solution to carry out detection to analyze, testing result as shown in Figures 1 to 4;
Utilize MS picture library to identify its structure respectively, result is as shown in table 1:
From the analysis result of table 1, in the sample gas constituents of embodiment 1 to 4, be all tested with the hexamethyldisiloxane ([(CH of architectural feature
3)
3si]
2and Trimethlyfluorosilane ((CH O)
3)
3siF), exist with the lithium hexafluorophosphate electrolyte solution not adding hexamethyldisiloxane additive of comparative example 1 and obviously distinguish.
In like manner, by gas chromatograph-mass spectrometer, qualitative analysis is carried out to the gas componant in lithium hexafluorophosphate electrolyte solution, oppositely can infer in lithium hexafluorophosphate electrolyte solution the alkyl silicon azane compounds whether adding other.
Therefore, the present invention judges that whether adding alkyl silicon azane compounds in electrolyte provides new detection means, and detection time is short, fast simple to operate, has better operability and practicality, thus is conducive to the quality control to lithium battery product.
Finally should be noted that; above embodiment is only in order to illustrate technical scheme of the present invention; but not limiting the scope of the invention; although done to explain to the present invention with reference to preferred embodiment; those of ordinary skill in the art is to be understood that; can modify to technical scheme of the present invention or equivalent replacement, and not depart from essence and the scope of technical solution of the present invention.
Claims (3)
1. the detection method of alkyl silicon azane compounds in lithium hexafluorophosphate electrolyte solution, is characterized in that: comprise the following steps:
1) sealing is preserved:
By lithium hexafluorophosphate electrolyte solution sample sealed storage in container, and make the volume of in closed container reserved 1/4 ~ 1/5 to hold escaping gas, 1 ~ 15 day standing time, the liquid phase in container is fully balanced;
2) gas chromatograph-mass spectrometer qualitative analysis:
Escaping gas in container is sampled, then carries out qualitative analysis with the gas ingredients of gas chromatograph-mass spectrometer to institute's sample drawing, confirm in lithium hexafluorophosphate electrolyte solution, whether to add alkyl silicon azane compounds;
Described alkyl silicon azane compounds is hexamethyldisiloxane or heptamethyldisilazane.
2. the detection method of alkyl silicon azane compounds in lithium hexafluorophosphate electrolyte solution according to claim 1, is characterized in that: in described lithium hexafluorophosphate electrolyte solution, the detection addition of alkyl silicon azane compounds is 1 ~ 1000ppm.
3. the detection method of alkyl silicon azane compounds in lithium hexafluorophosphate electrolyte solution according to claim 1, it is characterized in that: in described step 1), standing time is 3 ~ 10 days.
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| KR101955288B1 (en) * | 2015-10-06 | 2019-03-08 | 주식회사 엘지화학 | A device for high speed analyzing of gas sample using gas-chromatograph and a method thereof |
| CN106596772B (en) * | 2016-12-14 | 2019-07-12 | 广州天赐高新材料股份有限公司 | The detection method of state double bond compound is built up in a kind of lithium hexafluoro phosphate electrolyte solution |
| CN111060608A (en) * | 2019-12-03 | 2020-04-24 | 合肥国轩高科动力能源有限公司 | Method for detecting alkyl silicon compounds in lithium ion battery electrolyte |
| CN113793975B (en) * | 2021-08-31 | 2023-02-03 | 湖南法恩莱特新能源科技有限公司 | Preparation method of fluorine-containing electrolyte |
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| CN101101279A (en) * | 2006-07-04 | 2008-01-09 | 深圳市比克电池有限公司 | Quantitative analysis method for battery electrolyte organic components |
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| CN101740788A (en) * | 2009-12-22 | 2010-06-16 | 中银（宁波）电池有限公司 | Electrolyte, preparing method thereof and primary lithium battery prepared from same |
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