CN113376304B - Method for detecting carbonate organic matters and additives in lithium ion battery electrolyte by GC-MS (gas chromatography-Mass spectrometer) - Google Patents
Method for detecting carbonate organic matters and additives in lithium ion battery electrolyte by GC-MS (gas chromatography-Mass spectrometer) Download PDFInfo
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Abstract
The invention relates to the technical field of lithium ion battery electrolyte, and discloses a method for detecting carbonate organic matters and additives in the lithium ion battery electrolyte by GC-MS (gas chromatography-mass spectrometry). By pretreating the electrolyte, solid particles and hydrofluoric acid in the electrolyte are effectively prevented from causing the loss and corrosion of a supporter in a chromatographic column, the replacement frequency of the chromatographic column and a sample injection needle is reduced, and the maintenance cost of equipment is reduced; by adopting the mode full-spectrum scanning combining SCAN and SIM, the carbonate organic solvent with high concentration in the electrolyte can be detected, and a small amount of functional additive can be detected without omission; the linearity and the reproducibility of the components of the electrolyte are quantitatively analyzed by an external standard method, and the measurement accuracy is high.
Description
Technical Field
The invention relates to the technical field of lithium ion battery electrolyte, in particular to a method for detecting carbonate organic matters and additives in the lithium ion battery electrolyte by GC-MS.
Background
The electrolyte of the lithium ion battery consists of an organic solvent, a functional additive and electrolyte lithium salt, the performance of the electrolyte is closely related to the performance of the organic solvent, and the organic solvent widely used at the present stage comprises carbonates, ethers and carboxylates. Carbonates mainly include cyclic carbonates (e.g., ethylene carbonate EC and propylene carbonate PC) and chain carbonates (e.g., dimethyl carbonate DMC, diethyl carbonate DEC, ethyl methyl carbonate EMC). The functional additive can obviously improve certain performances of the lithium battery, such as SEI film performance improvement, lithium ion conductivity improvement, electrolyte thermal stability improvement, battery safety performance improvement and electrolyte stability improvement.
When the gas chromatography-mass spectrometer is used for testing and analyzing the lithium ion battery electrolyte, the electrolyte lithium salt is easy to form solid particles in a chromatographic column, the lithium salt is also easy to react with water to generate hydrofluoric acid (HF),such as: liPF 6 +H 2 O→POF 3 +2HF + LiF corrodes the sample injection needle, causes the supporter to run off in the chromatographic column, corrodes, has great destruction to the packing stability of gas chromatographic column, leads to the column loss serious in the test procedure, and the accuracy and the stability of test result reduce, influence the precision of instrument, on the other hand causes the life-span of chromatographic column to shorten, and the sample injection needle is changed frequently, has increased the fault rate of equipment, has improved the maintenance cost of detection maintenance equipment.
The method for detecting the carboxylic ester compounds in the lithium ion battery electrolyte is disclosed in Chinese patent with the authorization number of CN105467058B, published 2017, 5, month and 17, and qualitative and quantitative analysis is carried out on the carboxylic ester compounds by a gas chromatography-mass spectrometer by adopting an external standard method; impurities in the sample have no influence on the analysis result, and the method has good reproducibility and high accuracy; according to the invention, before a sample is analyzed, the sample to be detected is diluted to obtain a detection solution, and then the detection solution is detected and analyzed, so that the column loss is reduced, the corrosion of the sample to be detected on a chromatographic column is effectively prevented, and the maintenance cost of detection equipment is reduced; meanwhile, the influence of other impurities in the sample to be detected on the analysis result can be avoided.
In the patent, the sample to be detected is diluted, so that the corrosion of electrolyte to a chromatographic column cannot be effectively prevented, the diluted sample has low peak intensity due to too small concentration and is difficult to detect, and a full-spectrum scanning mode is adopted during operation, so that characteristic peaks of a target substance are easy to omit.
Disclosure of Invention
In order to solve the technical problems, the invention provides a method for detecting carbonate organic matters and additives in lithium ion battery electrolyte by GC-MS. And qualitatively analyzing the detection solution by combining an SCAN mode and an SIM mode in a full spectrum scanning mode of a gas chromatography-mass spectrometer, determining the types of the carbonate organic solvent and a small amount of additives, and then quantitatively determining by adopting an external standard method. The invention relates to pretreatment of electrolyte, selection of chromatographic column, a temperature-raising program and an external standard quantitative method.
The specific technical scheme of the invention is as follows: a GC-MS method for detecting carbonate organic matters and additives in lithium ion battery electrolyte comprises the following steps:
s1: adding an inorganic solution into the electrolyte, shaking up, centrifuging, and filtering to obtain a to-be-detected electrolyte;
s2: preparing a detection solution, measuring the detection solution in an SCAN and SIM mode, and determining characteristic qualitative ion peaks of all components in the detection solution;
s3: adding a solvent into the electrolyte to be detected in the step S1 to prepare a liquid to be detected, detecting the liquid to be detected according to the same method of the step S2, and performing qualitative detection on each component to be detected in the liquid to be detected;
s4: weighing at least three groups of pure substances of the components to be detected as S3, wherein the concentrations of the components to be detected in each group are different, the mass percentages of the components to be detected are consistent, and adding a solvent to obtain at least three groups of mixed standard solutions with different concentrations;
s5: detecting each standard solution by using an ion monitoring mode of a gas chromatography-mass spectrometer, recording the peak area corresponding to each standard solution, and drawing a standard curve according to the content and the peak area of each component to be detected in each standard solution to obtain a standard curve linear equation;
s6: and detecting the solution to be detected according to the same method of S5, recording peak areas, and calculating the concentration of each component to be detected in the lithium ion battery electrolyte according to the standard curve linear equation.
Preferably, the chromatographic measurement conditions in S3 and S3 are as follows: the chromatographic column is Rxi-5Sil MS30m multiplied by 0.25mm multiplied by 0.25um, the carrier gas is helium, the column flow is 1-1.5mL/min, the split ratio is (20: 1) - (50: 1), the injection port temperature is 240-250 ℃, the injection amount is 0.5-2uL, purging is 2-4mL/min, and the column temperature program: keeping the temperature at 35-45 deg.C for 3-8min, heating to 80-120 deg.C at a rate of 5-8 deg.C/min, heating to 240-260 deg.C at a rate of 15-25 deg.C/min, keeping the temperature for 1-3min, and heating to 270-300 deg.C at a rate of 10-50 deg.C/min, and keeping the temperature for 1-3min.
Determining the temperature of a sample inlet according to each component in the electrolyte, wherein the temperature of the sample inlet is higher than the highest boiling point of each component in the liquid to be detected, and the temperature cannot be too high, so that the decomposition and denaturation of the electrolyte are avoided, and the temperature of the sample inlet and the temperature rise rate ensure that each component can be well separated; the sample feeding amount and the split flow ratio are adjusted, so that the phenomenon that the chromatographic column is overloaded, excessive samples enter the chromatographic column and are overloaded, the separation efficiency is reduced, the peak is deformed and trailing, the corresponding component content cannot be detected due to the saturation of a detector, and the service life of the chromatographic column is influenced; the chromatographic column is thin, a sample to be detected cannot enter the chromatographic column instantly after being vaporized to generate gas expansion, a certain time is needed, and the time is too long to cause the spectral bandwidth, so that a part of the sample needs to be shunted in time.
Preferably, the solvent is one of acetone, methanol, ethanol or isopropanol.
Preferably, the inorganic solution in S1 is a saturated sodium carbonate solution.
Preferably, the centrifugation rate in S1 is 3000-5000r/min.
Adding saturated sodium carbonate solution into the electrolyte, centrifuging, collecting supernatant, and filtering to remove electrolyte lithium salt LiPF 6 And the lithium salt reacts with water in the storage process to generate hydrofluoric acid, so that the corrosion of the liquid to be detected on the sample injection needle is effectively prevented, the loss and the corrosion of a supporter in the chromatographic column are avoided, the maintenance cost of detection and maintenance equipment is reduced, and the qualitative and quantitative errors in the test caused by less additive content are reduced.
Preferably, the concentration of the detection solution in S2 and the concentration of the solution to be detected in S3 are 1500-2500ppm.
Preferably, the chromatographic column is a weakly polar column or a nonpolar column.
Preferably, the column temperature program sets the SIM mode fine scanning at 10.5-10.8min and 11.2-11.6min, and SCANs in SCAN mode at other times.
And the SCAN mode and the SIM mode in the full-spectrum scanning mode are mutually combined to carry out qualitative analysis on the detection liquid, so that each component to be detected in the detection liquid can be detected more comprehensively and accurately.
Compared with the prior art, the invention has the beneficial effects that:
(1) The electrolyte is pretreated, so that the carrier in the chromatographic column is effectively prevented from being lost and corroded due to solid particles and hydrofluoric acid, the replacement frequency of the chromatographic column and a sample injection needle is reduced, and the maintenance cost of equipment is reduced;
(2) By adopting a full spectrum scanning and qualitative mode combining SCAN and SIM, the method can ensure that the high-concentration carbonate organic solvent in the electrolyte can be detected, and a small amount of functional additive can be detected without omission;
(3) The components of the electrolyte are quantitatively analyzed by adopting an external standard method, the linearity and the reproducibility are good, and the measurement accuracy is high.
Drawings
FIG. 1 is a GC-MS chromatogram of example 1 of the present invention;
FIG. 2 is a GC-MS chromatogram of example 2 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantageous technical effects of the present invention more clearly understood, the present invention is further described in detail below with reference to the accompanying drawings and the detailed description. The devices, connections, and methods referred to in this disclosure are those known in the art, unless otherwise indicated.
Example 1
When the organic components in the electrolyte sample are known, 9 compounds, namely Ethylene Carbonate (EC), propylene Carbonate (PC), diethyl carbonate (DEC), dimethyl carbonate (DMC) and methyl ethyl carbonate (EMC), vinylene Carbonate (VC), fluoroethylene carbonate (FEC), phenylsulfone (PS) and Adiponitrile (ADN), are weighed according to the same mass, and acetone is used as a solvent to prepare a solution with the concentration of 2000ppm as a detection solution.
Adopting a GCMS-QP2010SE model gas chromatography-mass spectrometer, wherein the chromatographic conditions are as follows: the chromatographic column is Rxi-5Sil MS30m multiplied by 0.25mm multiplied by 0.25um (RESTEK chromatography), the carrier gas is helium, the column flow is 1.2mL/min, the split ratio is 50: 1, the sample inlet temperature is 240 ℃, the sample injection amount is 1uL, purging is 3mL/min, and the column temperature program: keeping the temperature at 40 deg.C for 5min, heating to 100 deg.C at a heating rate of 6 deg.C/min, heating to 260 deg.C at a heating rate of 20 deg.C/min, keeping the temperature for 2min, and heating to 280 deg.C at a heating rate of 40 deg.C/min, and keeping the temperature for 2min.
The gas chromatography-mass spectrometer is used for carrying out full spectrum scanning qualitative analysis on the detection liquid, SIM mode fine scanning is set at 10.5-10.8min and 11.2-11.6min, scanning is carried out in a SCAN mode at other time, the test result is shown in figure 1 (the ordinate in the figure is ion intensity, the unit of the ion intensity is not significant and is not marked), EC, PC, DEC, DMC, EMC, VC, FEC, PS and ADN are respectively detected, the peak intensities of 9 components are different, are not overlapped and are well separated, and the peak intensities of 3 components of VC, EC and PS are weaker.
Example 2
Putting 2g of electrolyte into a glass test tube, dropwise adding 0.2g of saturated sodium carbonate solution, shaking uniformly, putting the glass test tube into a tubular centrifuge, performing centrifugal separation at 3500r/min, and removing electrolyte lithium salt LiPF 6 And hydrofluoric acid generated by the reaction of the lithium salt with water during storage; and taking supernatant liquor in the glass test tube, filtering the supernatant liquor to be used as a sample to be detected, taking acetone as a solvent, and preparing solution with the concentration of 1500ppm to be used as liquid to be detected.
Adopting a GCMS-QP2010SE model gas chromatography-mass spectrometer, wherein the chromatographic conditions are as follows: the chromatographic column is Rxi-5Sil MS30m multiplied by 0.25mm multiplied by 0.25um (RESTEK chromatography), the carrier gas is helium, the column flow is 1.5mL/min, the split ratio is 50: 1, the sample injection amount is 1uL, the purging is 3mL/min, and the column temperature program: keeping the temperature at 40 deg.C for 5min, heating to 100 deg.C at a heating rate of 6 deg.C/min, heating to 280 deg.C at a heating rate of 30 deg.C/min, keeping the temperature for 2min, and heating to 300 deg.C at a heating rate of 50 deg.C/min, and keeping the temperature for 2min.
AND carrying out full spectrum scanning qualitative analysis on the liquid to be detected by a gas chromatography-mass spectrometer, setting SIM mode fine scanning at 10.5-10.8min AND 11.2-11.6min, scanning in a SCAN mode at other time, AND detecting EC, EMC, DEC, PC, PS AND AND in the electrolyte respectively as shown in figure 2 (the ordinate in the figure is the ionic strength, AND the unit does not have meaning AND is not marked) as the test result.
According toQualitatively analyzing the determined components of the carbonate organic solvent and the functional additive, weighing chromatographically pure chemicals of the components to be detected, taking acetone as a solvent to prepare three groups of mixed standard solutions with different concentrations, and knowing that the mass percentage of each organic matter component in the electrolyte sample is EC: EMC: and (4) DEC: PC: PS: AND: liPF (lithium ion particle Filter) 6 =25:40:15:4.5:2.5:0.5: 12.5, the component concentrations of the three sets of mixed standard solutions with different concentrations are shown in table 1:
TABLE 1 3 sets of mixed standard solutions of different concentrations
| Components | Standard solution A/ppm | Standard solution B/ppm | Standard solution C/ppm |
| EC | 20 | 100 | 1000 |
| EMC | 20 | 100 | 1000 |
| DEC | 3.75 | 75 | 750 |
| PC | 6 | 30 | 300 |
| | 5 | 25 | 250 |
| AND | 1.5 | 7.5 | 75 |
Example 3
Example 3 differs from example 2 in that: in the process of pretreating the electrolyte by using a saturated sodium carbonate solution, the reaction temperature is kept at 4 ℃, and then the solution to be tested is tested. The remaining test procedures and parameters were the same as in example 2.
Detecting the standard solution B by using an ion monitoring mode of a gas chromatography-mass spectrometer, recording peak areas corresponding to all components, drawing a standard curve corresponding to the concentration and the peak areas, wherein 6 components in the electrolyte have good linearity in the standard solution B, and the correlation coefficient is 0.9999. The sample introduction of the standard solution B is repeated for 5 times, the peak area reproducibility results of the components are shown in Table 2, the peak area relative standard deviation is less than 1%, and the reproducibility is good.
TABLE 2 reproducibility of peak area for each component in Standard solution B
| EC | EMC | DEC | PC | PS | ADN | |
| 1 | 2907 | 553 | 412 | 273 | 326 | 259 |
| 2 | 2900 | 552 | 410 | 272 | 329 | 257 |
| 3 | 2903 | 549 | 412 | 275 | 324 | 258 |
| 4 | 2899 | 548 | 415 | 276 | 327 | 255 |
| 5 | 2915 | 554 | 413 | 278 | 326 | 256 |
| Average | 2905 | 551 | 412 | 275 | 326 | 257 |
| RSD％ | 0.22 | 0.47 | 0.44 | 0.85 | 0.56 | 0.62 |
In example 3, the measured contents of the components in the electrolyte are more accurate than those in example 2, because the volatilization of the electrolyte can be reduced by the low-temperature reaction environment in the pretreatment process of the electrolyte by using the saturated sodium carbonate solution, so that the measured contents of the components are more accurate.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and all simple modifications, changes and equivalent structural changes made to the above embodiment according to the technical spirit of the present invention still belong to the protection scope of the technical solution of the present invention.
Claims (4)
1. A GC-MS method for detecting carbonate organic matters and additives in lithium ion battery electrolyte is characterized by comprising the following steps:
s1: adding an inorganic solution into the electrolyte, shaking up, centrifuging, and filtering to obtain a to-be-detected electrolyte; the inorganic solution is a saturated sodium carbonate solution;
s2: preparing a detection solution, wherein the detection solution is a mixed solution of 9 compounds including ethylene carbonate, propylene carbonate, diethyl carbonate, dimethyl carbonate and ethyl methyl carbonate, vinylene carbonate, fluoroethylene carbonate, phenylsulfone and adiponitrile, and the detection solution is measured in an SCAN and SIM mode to determine characteristic qualitative ion peaks of all components in the detection solution;
s3: adding a solvent into the electrolyte to be tested in the step S1 to prepare a solution to be tested, testing the solution to be tested according to the same method of the step S2, and performing qualitative determination on each component to be tested in the solution to be tested;
s4: weighing at least three groups of pure substances of the components to be detected as S3, wherein the concentrations of the components to be detected in each group are different, the mass percentages of the components to be detected are consistent, and adding a solvent to obtain at least three groups of mixed standard solutions with different concentrations;
s5: detecting each standard solution by using an ion monitoring mode of a gas chromatography-mass spectrometer, recording the peak area corresponding to each standard solution, and drawing a standard curve according to the content and the peak area of each component to be detected in each standard solution to obtain a standard curve linear equation;
s6: detecting the solution to be detected according to the same method of S5, recording peak areas, and calculating the concentration of each component to be detected in the lithium ion battery electrolyte according to the standard curve linear equation;
in S2 and S3, a chromatographic column is Rxi-5Sil MS30m multiplied by 0.25mm multiplied by 0.25um, carrier gas is helium, the column flow is 1-1.5mL/min, the split ratio is 20: 1-50: 1, the injection port temperature is 240-250 ℃, the sample injection amount is 0.5-2uL, purging is carried out for 2-4mL/min, and the column temperature program is as follows: keeping the temperature at 35-45 deg.C for 3-8min, heating to 80-120 deg.C at a rate of 5-8 deg.C/min, heating to 240-260 deg.C at a rate of 15-25 deg.C/min, keeping the temperature for 1-3min, and heating to 270-300 deg.C at a rate of 10-50 deg.C/min, and keeping the temperature for 1-3min; the column temperature program sets SIM mode fine scanning at 10.5-10.8min and 11.2-11.6min, and SCANs in SCAN mode at other times.
2. The method for detecting carbonate organic matters and additives in lithium ion battery electrolyte by GC-MS as claimed in claim 1, wherein the solvent in S3 and S4 is one of acetone, methanol, ethanol or isopropanol.
3. The method for detecting carbonate organic matters and additives in lithium ion battery electrolyte by GC-MS as claimed in claim 1, wherein the centrifugation rate in S1 is 3000-5000r/min.
4. The method for detecting carbonate organic matters and additives in lithium ion battery electrolyte by GC-MS according to claim 1, wherein the concentration of the detection solution in S2 and the concentration of the solution to be detected in S3 are 1500-2500ppm.
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