CN100368801C - Method for measuring organic component in lithium ion cell electrolyte - Google Patents
Method for measuring organic component in lithium ion cell electrolyte Download PDFInfo
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Abstract
This is a test organic component method in lithium ion battery electrolyte. (1) Put DMC,EMC,DEC,EC,PC together into electrolyte and use absolute ethyl as thinner to get standard solution. Carry GC-MS test, get corresponding abundance value and protract standard curve according the content and abundance value of each solvent. (2) Add battery electrolyte into separating funnel and deionwater, surge the admixture for 1-5 minutes, add dichloromethane to surge for 8-12 minutes, eliminate lithium salt; extract the underlayer organic solution to filtrate in terrarium with absolute sodium carbonate. (3) Dilute the liquor got from step (2) into absolute ethyl, and keep its concentration accords with the standard curve range to step (1). (4) Carry GC-MS test in the condition as step (1), account the solvent compose and content of the original battery electrolyte in term of the standard curve to step (1). This method can avoid the cauterization to GC-MS test system by lithium salt component in electrolyte without affecting the fix quantify test to organic component.
Description
Technical field:
The present invention relates to the assay method of organic component in the battery electrolyte, especially a kind of assay method of lithium-ion battery electrolytes organic component.
Background technology:
Lithium-ion battery electrolytes is very responsive to performances such as the energy density of electrode and battery, cycle life, securities.Therefore selecting suitable organic electrolyte is one of key issue that obtains high-energy-density, long circulation life and cell safety.The initial charge/discharge capacity of battery has sizable difference owing to the combination of material with carbon element and electrolytic solution is different, so lay special stress on electrolytic solution will adapt with carbon anode when the design battery.In the commodity lithium ion battery, the lithium salts that electrolytic solution is commonly used is LiPF
6, solvent is that cyclic carbonate Arrcostab and chain alkyl carbonate etc. mix binary, ternary or the multicomponent system of forming mutually.The organic component of lithium-ion battery electrolytes mainly contains: dimethyl carbonate (DMC), diethyl carbonate (DEC), ethylene carbonate ester (EC), propylene glycol carbonate (PC), methyl ethyl carbonate (EMC).Organic electrolyte plays a part to carry lithium ion between the both positive and negative polarity of lithium ion battery, although can form electrolytic solution by a variety of organic solvents and lithium salts, but that really can use in lithium ion battery is few in number, and the composition of therefore analyzing battery electrolyte has important effect to the research and development battery electrolyte.
At present, to lithium-ion battery electrolytes organic component Study of test method, develop into the comparatively accurate quantitative analysis stage from initial qualitative analysis.Bradley A.Johnson and Ralph E.White propose to utilize GC/MS (gas chromatography and mass spectrum are online) method to analyze the lithium ion battery organic electrolyte at interim the 70th volume 48-54 page or leaf of J.ofPowerSour. in 1998.Steven E.Sloop, John B.Kerr and Kim Kinoshita 119-121 in J.of PowerSour. periodical in 2003 rolls up in the article of 330-337 page or leaf and uses GC/MS (Agilent6890/5973MSD) that lithium-ion battery electrolytes organic component DMC, EMC, DEC and the EC etc. of methylene chloride dissolving have been carried out qualitative analysis.(CN1712956A 2005.12.28) discloses the quantivative approach of utilizing gas chromatography and the online method of mass spectrum to measure organic component in the invention of Zhang Yingqiang " quantitative analysis method of lithium-ion battery electrolytes organic component ".
But in using GC-MS test lithium-ion battery electrolytes during organic component content, electrolyte lithium salt---lithium hexafluoro phosphate can cause corrosion and pollutes the GC system.This is because lithium hexafluoro phosphate is easy to decompose, generate LiF and HF, the LiF solid is deposited on bushing pipe and pillar port easily, HF then can cause expendable corrosivity effect to pillar, therefore before with the GC-MS system testing, lithium salt component should be removed, at present, still find no the report that closes these class methods.
Summary of the invention:
The purpose of this invention is to provide a kind of assay method of organic component of effective lithium-ion battery electrolytes, thereby avoid corrosion and the pollution of lithium salt component in electrolyte, do not influence the quantitative test of organic component simultaneously the GC-MS test macro.
A kind of method of measuring organic component in the lithium-ion battery electrolytes of the present invention, carry out according to following steps:
(1) prepares electrolytic solution with DMC, EMC, DEC, EC, PC, use absolute ethyl alcohol as thinning agent then, the standard solution of preparation variable concentrations is measured with GC-MS again, the abundance value that meets with a response, and according to mass content and the abundance value drawing standard curve of each solvent in total solvent;
(2) in separating funnel, add the battery electrolyte sample, add deionized water again; Mixed liquor was fully vibrated 1-5 minute, add methylene chloride again, fully vibrated again 8-12 minute, remove lithium salts; Take out lower floor's organic phase solution, in being filled with the glass container of natrium carbonicum calcinatum, filter, remove moisture wherein;
(3) solution that filters the back gained in the step (2) is diluted with absolute ethyl alcohol, its concentration is in the standard curve range described in the step (1);
(4) under the test condition identical, test, calculate the composition and the content of each solvent in the primary element electrolytic solution sample according to step (1) gained typical curve with GC-MS with step (1).
A kind of method of measuring organic component in the lithium-ion battery electrolytes of the present invention, the volume of the described deionized water in its step (2) is the 30%-70% of battery electrolyte sample volume, and the volume of described methylene chloride is the 80%-120% of battery electrolyte sample volume.
For battery to be tested, at first it is discharged, dissect then and obtain the electrode group, with 1,2-dimethoxy-ethane (DME) soaks utmost point group as extractant, and organic solvent component wherein is extracted among the DME.In order to guarantee test concentrations, the consumption of extractant can be advisable the complete submergence of electrode group with firm, soaks the extraction time at 12-24 hour.Gained extract filter paper filtering is removed impurity such as utmost point powder, is diluted to 1～50 times of initial volume with absolute ethyl alcohol, tests with GC-MS under the test condition identical with step (1).Calculate the composition and the content of each solvent of electrolytic solution in the primary element sample according to step (1) gained typical curve.
Beneficial effect of the present invention is:
1. with extraction of the present invention electrolytic solution is carried out pre-treatment, desalting efficiency can reach 99.85%, simultaneously, does not influence the quantitative test (relative error is in ± 1%) of solvent composition in the electrolytic solution.
2. for the test of bath composition in the battery, take extraction that the solvent composition in the battery is extracted into 1, in the 2-dimethoxy-ethane (DME), this method is not when influencing the solvent composition quantitative test, and desalting efficiency also can reach 99.97%.
3. chromatographic column is made of glass or quartz, and its filler is generally polysiloxane-based material, and HF is well-known to the corrosive attack of glass, quartz and other metal materials.Along with the prolongation of time, chromatographic column contaminated and corrosion slowly, thus disturb, influence the result of test even make chromatographic column lose separating power.And along with the accumulation of amount and the prolongation of time, HF can also cause corrosion and pollution to parts such as detecting devices.In the method for testing of the present invention, desalting efficiency is up to more than 99%, thereby avoids corrosion and the pollution of the decomposition product of lithium salts to the GC-MS test macro, increases the service life, and avoids polluting and corrosion.
Embodiment:
Further specify technical scheme of the present invention below by specific embodiment.The use instrument is: the Agilent6890N-5973N gas chromatograph-mass spectrometer; Dionex ICS-1500 chromatography of ions.
Embodiment 1
(1) prepares electrolytic solution with DMC, EMC, DEC, EC, PC, use absolute ethyl alcohol as thinning agent then, the standard solution of preparation variable concentrations is measured with GC-MS again, the abundance value that meets with a response, and according to mass content and the abundance value drawing standard curve of each solvent in total solvent;
(2) get 10ml electrolytic solution sample to be measured, to wherein adding the 5ml deionized water, 2min fully vibrates, then add the 10ml methylene chloride, the 10min that fully vibrates once more, standing demix takes out lower floor's organic phase solution, in being filled with the glass column of natrium carbonicum calcinatum, filter, to remove moisture wherein;
(3) solution that filters the back gained in the step (2) is diluted with absolute ethyl alcohol, its concentration is in the standard curve range described in the step (1);
(4) under the test condition identical, test, calculate the composition and the content of each solvent in the primary element electrolytic solution sample according to step (1) gained typical curve with GC-MS with step (1).
Embodiment 2
(1) prepares electrolytic solution with DMC, EMC, DEC, EC, PC, use absolute ethyl alcohol as thinning agent then, the standard solution of preparation variable concentrations is measured with GC-MS again, the abundance value that meets with a response, and according to mass content and the abundance value drawing standard curve of each solvent in total solvent;
(2) get 10ml electrolytic solution sample to be measured, to wherein adding the 3ml deionized water, 5min fully vibrates, then add the 8ml methylene chloride, the 12min that fully vibrates once more, standing demix takes out lower floor's organic phase solution, in being filled with the glass column of natrium carbonicum calcinatum, filter, to remove moisture wherein;
(3) solution that filters the back gained in the step (2) is diluted with absolute ethyl alcohol, its concentration is in the standard curve range described in the step (1);
(4) under the test condition identical, test, calculate the composition and the content of each solvent in the primary element electrolytic solution sample according to step (1) gained typical curve with GC-MS with step (1).
Embodiment 3
(1) prepares electrolytic solution with DMC, EMC, DEC, EC, PC, use absolute ethyl alcohol as thinning agent then, the standard solution of preparation variable concentrations is measured with GC-MS again, the abundance value that meets with a response, and according to mass content and the abundance value drawing standard curve of each solvent in total solvent;
(2) get 10ml electrolytic solution sample to be measured, to wherein adding the 7ml deionized water, 1min fully vibrates, then add the 12ml methylene chloride, the 8min that fully vibrates once more, standing demix takes out lower floor's organic phase solution, in being filled with the glass column of natrium carbonicum calcinatum, filter, to remove moisture wherein;
(3) solution that filters the back gained in the step (2) is diluted with absolute ethyl alcohol, its concentration is in the standard curve range described in the step (1);
(4) under the test condition identical, test, calculate the composition and the content of each solvent in the primary element electrolytic solution sample according to step (1) gained typical curve with GC-MS with step (1).
Embodiment 4
(1) prepares electrolytic solution with DMC, EMC, DEC, EC, PC, use absolute ethyl alcohol as thinning agent then, the standard solution of preparation variable concentrations is measured with GC-MS again, the abundance value that meets with a response, and according to mass content and the abundance value drawing standard curve of each solvent in total solvent;
(2) get 10ml electrolytic solution sample to be measured, to wherein adding the 4ml deionized water, 4min fully vibrates, then add the 11ml methylene chloride, the 10min that fully vibrates once more, standing demix takes out lower floor's organic phase solution, in being filled with the glass column of natrium carbonicum calcinatum, filter, to remove moisture wherein;
(3) solution that filters the back gained in the step (2) is diluted with absolute ethyl alcohol, its concentration is in the standard curve range described in the step (1);
(4) under the test condition identical, test, calculate the composition and the content of each solvent in the primary element electrolytic solution sample according to step (1) gained typical curve with GC-MS with step (1).
To carry out the mensuration of next step organic component in the specific embodiment 2 through the battery electrolyte of desalination:
1. the preparation of electrolytic solution standard solution: the quality of each solvent composition and adjuvant is as shown in table 1 respectively.Respectively it is diluted 10 times with absolute ethyl alcohol, 50 times, 100 times, 250 times.
Table 1 electrolytic solution standard solution preparation table
| Solvent | Quality/g | Mass content/ppm |
| DMC EMC DEC EC PC VC PS BP | 8.7345 7.6023 7.0503 9.8180 10.1402 0.4580 1.3582 0.9509 | 201510 175389 162654 226507 233940 10566 31334 21938 |
2. test the standard solution of above-mentioned variable concentrations with GC-MS, according to every kind of solvent strength and abundance response drawing standard curve thereof, gained typical curve equation is as shown in table 2 then, and the facies relationship number average illustrates to have good linear relationship more than 0.99.
Table 2 typical curve equation and related coefficient thereof
| Solvent | Working curve | Related coefficient |
| DMC EMC DEC EC PC VC PS BP | Area＝5530Amt+8.59000000 Area＝6340Amt+9910000 Area＝7210Amt+9740000 Area＝10400Amt+2520000 Area＝8570Amt+3700000 Area＝20600Amt-17800 Area＝6840Amt+75200 Area＝37700Amt+16800000 | 0.99984 0.99988 0.99805 0.99471 0.99998 0.99995 0.99988 0.99987 |
3. get 10ml electrolytic solution sample to be measured, to wherein adding the 5ml deionized water, 2min fully vibrates, then add the 10ml methylene chloride, the 10min that fully vibrates once more, standing demix, take out lower floor's organic phase solution, the glass container that is filled with natrium carbonicum calcinatum filters, to remove moisture wherein.
4. get step 3 gained organic phase solution, dilute 50 times, form and content with the GC-MS test solvent under the condition identical with step 2, concrete data see Table 3.
The test result of table 3 electrolytic solution sample
| Solvent Solvent | The % total solvent | Relative error Relative error | ||||
| Test result 1 | Test result 2 | Test result 3 | Mean value | Actual value | ||
| DMC EMC DEC EC PC VC PS BP | 20.0 17.5 16.4 22.8 23.3 1.1 3.0 2.2 | 20.1 17.4 16.4 22.8 23.3 1.0 3.0 2.2 | 20.1 17.5 16.3 22.7 23.4 1.0 3.0 2.2 | 20.07 17.47 16.35 22.77 23.33 1.05 2.98 2.19 | 20.15 17.54 16.27 22.65 23.39 1.06 3.13 2.19 | -0.4％ -0.4％ 0.5％ 0.5％ -0.3％ -0.7％ -4.8％ -0.2％ |
This shows, after the desalination pre-treatment, the relative error of lithium-ion battery electrolytes organic component quantitative test is in ± 1%, for the lower additive component of content, test error illustrates that this pre-treating method does not influence the quantitative test of electrolyte component about ± 5%.
5. getting step 3 gained organic phase solution, after contrary chloroazotic acid resolution process, is 174.7ppm with chromatography of ions test F content wherein, i.e. remaining LiPF in the electrolytic solution
6Concentration be 0.0015mol/L only, prove that this pre-treating method can reach effective desalination effect, concrete data such as table 4.
The desalination effect of table 4 electrolytic solution sample
| Original LiPF 6Concentration (mol/L) | F after the pre-treatment -Concentration (ppm) | LiPF after the pre-treatment 6Concentration (mol/L) | Desalting efficiency (%) |
| 1.00 | 174.7 | 0.0015 | 99.85 |
6. for mesuring battary, at first with its discharge, dissection, gained utmost point group is soaked extraction 12h with DME, 5 times of ethanol dilutions of gained solution, the composition and the content of test organic component under the condition identical with step 1, result such as table 5.
The test result of electrolytic solution in table 5 battery sample
| Solvent | The % total solvent | Relative error | ||||||
| Test result 1 | Test result 1 | Test result 1 | Mean value | Correction coefficient | Corrected value | Actual value | ||
| EMC EC PC VC | 43.9 48.8 6.3 1.0 | 45.3 47.5 6.1 1.0 | 44.1 48.6 6.3 1.0 | 44.5 48.3 6.2 1.0 | 1.581 1.000 1.000 1.000 | 56.3 38.7 5.0 1.0 | 55 40 5 1.2 | 2.4％ -3.3％ -0.2％ -16.7％ |
| PS | 1.9 | 1.9 | 1.9 | 1.9 | 1.000 | 1.9 | 3.6 | -47.2％ |
As shown in Table 5, test error for electrolytic solution in the battery is relatively large, its reason mainly is: in battery charge and discharge process, ester exchange reaction takes place in EMC, content significantly reduces (relative error of test is-31.9%), therefore introduce the reaction correction factor 1.581 (calculate and get) of EMC here, can find to proofread and correct the relative error reduction (all in ± 3.3%) of back solvent composition test by experimental result repeatedly.
For the lower additive component of content, in battery operated different phase corresponding reaction takes place according to the difference of its function, as film for additive (VC, PS etc.), promptly participate in film formation reaction at the first charge and discharge process of battery, therefore waste is bigger, causes the relative error of test result and original formulation bigger.
7. get step 6 gained electrolytic solution, use the method identical, test F-content wherein, concrete data such as table 6 with step 5.
The desalination effect of electrolytic solution in table 6 battery sample
| Original LiPF 6Concentration (mol/L) | F -Concentration (ppm) | LiPF 6Concentration (mol/L) | Desalting efficiency (%) |
| 1.00 | 38.4 | 0.0003 | 99.97 |
Hence one can see that, after used for electrolyte extraction of the present invention carries out the desalination pre-treatment, and its LiPF
6Concentration significantly reduces, and therefore can reach effective desalination effect, thereby avoid corrosion and pollution to the GC-MS test macro; Simultaneously, this pre-treating method does not influence the quantitative test of organic component.
The electrolyte of removing the salt front and back is carried out the organic component analysis of test results, and the present invention has following beneficial effect as can be known:
1. with extraction of the present invention electrolyte is carried out pre-treatment, desalting efficiency can reach 99.85%, simultaneously, does not affect the quantitative test (relative error is in ± 1%) of solvent composition in the electrolyte, thereby avoid corrosion and pollution to the GC-MS test macro, increase the service life.
2. for the test of bath composition in the battery, take extraction that the solvent composition in the battery is extracted in 1, the 2-dimethoxy-ethane (DME), this method is not when affecting the solvent composition quantitative test, and desalting efficiency also can reach 99.97%.
Claims (2)
1. a method of measuring organic component in the lithium-ion battery electrolytes is characterized in that, carries out according to following steps:
(1) prepares electrolytic solution with solvent dimethyl carbonate DMC, methyl ethyl carbonate EMC, diethyl carbonate DEC, ethylene carbonate ester EC, propylene glycol carbonate PC, use absolute ethyl alcohol as thinning agent then, the standard solution of preparation variable concentrations, measure with GC-MS again, the abundance value that meets with a response, and according to mass content and the abundance value drawing standard curve of each solvent in total solvent;
(2) in separating funnel, add the battery electrolyte sample, add deionized water again; Mixed liquor was fully vibrated 1-5 minute, add methylene chloride again, fully vibrated again 8-12 minute, remove lithium salts; Take out lower floor's organic phase solution, in being filled with the glass container of natrium carbonicum calcinatum, filter, remove moisture wherein;
(3) solution that filters the back gained in the step (2) is diluted with absolute ethyl alcohol, its concentration is in the standard curve range described in the step (1);
(4) under the test condition identical, test, calculate the composition and the content of each solvent in the battery electrolyte sample according to step (1) gained typical curve with GC-MS with step (1).
2. a kind of method of measuring organic component in the lithium-ion battery electrolytes according to claim 1, it is characterized in that, the volume of the deionized water in the described step (2) is the 30%-70% of battery electrolyte sample volume, and the volume of methylene chloride is the 80%-120% of battery electrolyte sample volume.
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| CN103235049B (en) * | 2013-03-29 | 2014-12-10 | 东莞市杉杉电池材料有限公司 | Detection method of lithium hexafluorophosphate solution |
| CN104090060B (en) * | 2014-07-28 | 2015-10-28 | 广州天赐高新材料股份有限公司 | The detection method of residual solvent in electrolyte lithium salt |
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| CN111257470B (en) * | 2020-03-03 | 2023-05-23 | 广州天赐高新材料股份有限公司 | Pretreatment method and detection method for detection of electrolyte organic solvent |
| CN112630334B (en) * | 2020-12-15 | 2022-09-27 | 厦门海辰储能科技股份有限公司 | Organic phase ratio detection method of electrolyte containing TMSP |
| CN112763291A (en) * | 2020-12-28 | 2021-05-07 | 江苏中兴派能电池有限公司 | Method for rapidly obtaining free electrolyte of battery |
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