CN106596772A - Method for detecting aggregated double-bone compounds in lithium hexafluorophosphate electrolyte solution - Google Patents
Method for detecting aggregated double-bone compounds in lithium hexafluorophosphate electrolyte solution Download PDFInfo
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- CN106596772A CN106596772A CN201611149293.5A CN201611149293A CN106596772A CN 106596772 A CN106596772 A CN 106596772A CN 201611149293 A CN201611149293 A CN 201611149293A CN 106596772 A CN106596772 A CN 106596772A
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- electrolyte solution
- double bond
- hexafluoro phosphate
- lithium hexafluoro
- bond compound
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- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
Abstract
The invention discloses a method for detecting aggregated double-bone compounds in a lithium hexafluorophosphate electrolyte solution. According to the method, a gas chromatograph-mass spectrometer is used for qualitatively analyzing trace impurity components in the lithium hexafluorophosphate electrolyte solution, standard impurity samples are subjected to sample injection validation with the help of a gas chromatograph, whether or not the aggregated double-bone compounds are added into the lithium hexafluorophosphate electrolyte solution is inferred reversely, and accordingly an effective method for indirect detection of the trace additives in the electrolyte solution is provided. The method has the advantages of simplicity in operation and high practicality, is of great significance to detection of other trace additives in the electrolyte solution and is beneficial to quality control of the electrolyte solution of lithium-ion batteries.
Description
Technical field
The present invention relates to the detection technique field of lithium ion battery electrolyte solution, and in particular to a kind of lithium hexafluoro phosphate electricity
The detection method of state double bond compound is built up in electrolyte solution.
Background technology
The advantages such as lithium ion battery has that specific energy is high, voltage is high, has extended cycle life, environmental friendliness, are widely used in
The fields such as number, energy storage, power, militay space flight and communication apparatus.
Electrolyte solution plays the work of transmission electric charge as the important component part of lithium ion battery between battery plus-negative plate
With.Electrolyte solution is typically made up of electrolyte lithium salt, organic solvent and additive, appearance of its product quality to lithium ion battery
The performances such as amount performance, circulation and high/low temperature are most important.At present commodity electrolyte lithium salts is mainly LiPF6, it is very quick to water
Sense, can react with moisture micro in electrolyte solution：LiPF6 + H2O → LiF+ 2HF+POF3, reaction generation
HF not only corrosion electrode active materials, and be easily destroyed solid electrolyte interface film SEI, deterioration.Therefore, lithium
Ion battery electrolyte solution will strictly control wherein H during production, transport, storage and use2The content of O and HF.
In order to avoid H in electrolyte solution2O and HF contents during transport and use are raised, in electrolyte solution
Micro eliminating water deacidification additive is added to be more typical method.Now there are some researches show, combined by elements such as carbon, nitrogen, oxygen and
Into accumulation state double bond compound, it is easy to H2There is additive reaction in O and HF, 50 ~ 1000ppm is added in electrolyte solution
Such compound can play significant eliminating water deacidification effect, be conducive to strengthening electrolyte solution stability.However, building up state double bond
Compound and H2There is certain impact, property of its amount ranges to lithium battery product on performance of lithium ion battery in the product of O
Can be most important, lithium battery manufacturer needs to build up state double bond compound to realize the quality pipe of electrolyte solution by detection
Control.
Due to building up state double bond compound addition extremely pettiness, the H in electrolyte solution in addition2O and HF reactions are consumed,
Cannot be detected substantially by conventional component analyzing method-gas chromatogram.Therefore, it is badly in need of a kind of lithium hexafluoro phosphate electricity of exploitation
The detection method of state double bond compound is built up in electrolyte solution, to help quality pipe of the cell production companies to electrolyte solution
Control.
The content of the invention
For a kind of not enough present in background above technology, hexafluoro phosphorus simple to operate, practical of present invention offer
The detection method of state double bond compound is built up in sour lithium electrolyte solution.
To realize object above, technical scheme is as follows：
The detection method of state double bond compound is built up in a kind of lithium hexafluoro phosphate electrolyte solution, is comprised the following steps：
A. electrolyte solution sealing preserve：
By lithium hexafluoro phosphate electrolyte solution sealing preserve to be detected in the steel cylinder of nitrogen atmosphere, 2 ~ 60 are placed under room temperature
My god, accumulation state double bond compound is fully reacted；
B. gas chromatograph-mass spectrometer qualitative analyses trace impurity composition：
Qualitative analyses are carried out to the electrolyte solution composition after placement by gas chromatograph-mass spectrometer, to confirm hexafluorophosphoric acid lithium electrolyte
Whether containing the trace impurity composition beyond conventional ingredient in solution；
C. gas chromatograph standard sample sample introduction checking：
By trace impurity standard sample difference sample introduction checking of the gas chromatograph to detecting in electrolyte solution and step b,
With impurity component reliability in verification step b, and it is double reversely to speculate whether lithium hexafluoro phosphate electrolyte solution added accumulation state
Key compound.
Preferably, state double bond compound is built up in the lithium hexafluoro phosphate electrolyte solution to have shown in Formulas I ~ formula III
Any one structure：
Formulas I
Formula II
Formula III
Wherein, R1~R4Independently represent that straight chained alkyl, branched alkyl, nitrogen that carbon number is 2 ~ 15 replace branched alkyl, ring
Shape alkyl or aromatic radical.
Preferably, it is N, N '-dicyclohexyl carbon two that state double bond compound is built up in the lithium hexafluoro phosphate electrolyte solution
Imines, N, N '-DIC and 1- (3- dimethylaminopropyls) -3- ethyl carbodiimides, benzene Carbimide.
Any one in ester, toluene di-isocyanate(TDI), '-diphenylmethane diisocyanate, hexamethylene diisocyanate.
Preferably, in the lithium hexafluoro phosphate electrolyte solution build up state double bond compound detection range be 50 ~
2000ppm。
Preferably, place 3 ~ 15 days under electrolyte solution room temperature in step a.
The detection method principle of the present invention is as follows：
In lithium hexafluoro phosphate electrolyte solution, always there is micro moisture, inevitably with electrolyte lithium salt hexafluorophosphoric acid
There is following reaction in lithium：
If adding in lithium hexafluoro phosphate electrolyte solution and building up state double bond compound, due to its unsaturation, carbodiimide
It is easy to and H in electrolyte solution with isocyanates2There is following additive reaction in O：
The product for generating above gives birth to other reactions in acidic electrolysis bath relaying supervention.
Below with N, as a example by N '-dicyclohexylcarbodiimide, its course of reaction in the electrolytic solution is described in detail：
Easily there is scission of link in the product that above-mentioned course of reaction is generated, generate cyclohexylamine in sour environment：
Cyclohexylamine is hydrolyzed with minor amount of water, generates corresponding Hexalin：
There is following substitution reaction or elimination reaction in sour environment in Hexalin：
Qualitative analyses are carried out to the electrolyte solution composition after placement by gas chromatograph-mass spectrometer, analysis wherein whether there is fluoro ring
Hexane and cyclohexene, you can preliminary to confirm whether added N, N '-dicyclohexyl carbon two in lithium hexafluoro phosphate electrolyte solution
Imines；
By gas chromatograph to electrolyte solution and fluoro hexamethylene, the difference sample introduction checking of cyclohexene standard sample, to confirm
Above two impurity component reliability, and reversely speculate that lithium hexafluoro phosphate electrolyte solution added N, N '-dicyclohexyl carbon
Diimine.
In the same manner, can reversely speculate in lithium hexafluoro phosphate electrolyte solution whether added other accumulations by same procedure
State double bond compound.
It is an advantage of the current invention that：
The invention provides the detection method of state double bond compound is built up in a kind of lithium hexafluoro phosphate electrolyte solution, by makings
Combined instrument carries out qualitative analyses to trace impurity composition in lithium hexafluoro phosphate electrolyte solution, by gas chromatograph to impurity mark
Quasi- sample carries out sample introduction checking, and then reversely speculates in lithium hexafluoro phosphate electrolyte solution whether added accumulation state double bond chemical combination
Thing, the indirect detection for such trace mineral supplement in electrolyte solution provides effective method.The present invention solves electricity
Build up in electrolyte solution state double bond compound because consumption is few, the reaction problem that consumes and cannot detect, with simple to operate and
Practical the features such as, lithium battery producer is conducive to realize effective management and control of lithium ion battery electrolyte solution.
Description of the drawings：
Fig. 1 is the electrolyte solution gas chromatograph testing result figure of comparative example of the present invention；
Fig. 2 is the electrolyte solution gas chromatograph testing result figure of the embodiment of the present invention 1；
Fig. 3 is the electrolyte solution gas chromatograph-mass spectrometer testing result figure of the embodiment of the present invention 1；
Fig. 4 is cyclohexene standard sample gas chromatograph testing result figure；
Fig. 5 is fluoro hexamethylene standard sample gas chromatograph testing result figure；
Fig. 6 is the electrolyte solution gas chromatograph testing result figure that the present invention implements embodiment 2.
Specific embodiment
Below by exemplary embodiment, the present invention will be further elaborated；But the scope of the present invention should not limit to
In the scope of embodiment, any change or change without departing from present subject matter can be understood by the person skilled in the art,
All within protection scope of the present invention.
Following examples are with N, N'- dicyclohexylcarbodiimides（DCC）It is added as state double bond compound is built up.
Comparative example
Preparation does not contain the lithium hexafluoro phosphate electrolyte solution for building up state double bond compound：
In the glove box full of argon, the high-purity organic solvent diethyl carbonate for accounting for electrolyte solution 90wt% is weighed, then
The lithium hexafluoro phosphate of 10wt% is added thereto to, is stirred to lithium salts and is completely dissolved, be transferred to the steel cylinder of nitrogen atmosphere
In, comparative example is labeled as in case detection.
Electrolyte solution gas chromatograph is detected：
Composition detection analysis is carried out to comparative example electrolyte solution using gas chromatograph, testing result is as shown in Figure 1.
Embodiment 1
Prepare the lithium hexafluoro phosphate electrolyte solution that state double bond compound is built up containing 700ppm：
In the glove box full of argon, the high-purity organic solvent diethyl carbonate for accounting for electrolyte solution 90wt% is weighed, then
Addition accounts for the N of electrolyte solution 700ppm mass fractions, and N'- dicyclohexylcarbodiimides add after stirring 5min to mixed solution
Enter the lithium hexafluoro phosphate of 10wt%, stir to lithium salts and be completely dissolved, in being transferred to the steel cylinder of nitrogen atmosphere, be labeled as
Embodiment 1 is in case detection.
Electrolyte solution gas chromatograph, gas chromatograph-mass spectrometer detection：
Composition detection analysis is carried out to the electrolyte solution of embodiment 1 using gas chromatograph, testing result is as shown in Figure 2.
The impurity component that GC in embodiment 1 is detected is analyzed using gas chromatograph-mass spectrometer, testing result such as Fig. 3 institutes
Show.
The impurity component standard sample that GC-MS in embodiment 1 is detected is verified using gas chromatograph, detection knot
Fruit is as shown in Figure 4 and Figure 5.
According to above-mentioned impurity component the result, reversely speculate in lithium hexafluoro phosphate electrolyte solution and build up state double bond chemical combination
Thing structure chart.
Embodiment 2
Prepare the lithium hexafluoro phosphate electrolyte solution that state double bond compound is built up containing 400ppm：
In the glove box full of argon, ethylene carbonate, Ethyl methyl carbonate and the carbonic acid diethyl of electrolyte solution 85wt% will be accounted for
Ester is EC in mass ratio：EMC：DEC=3：5：2 are mixed, and are subsequently adding the N for accounting for electrolyte solution 400ppm mass fractions,
N'- dicyclohexylcarbodiimides, stir 5min after to mixed solution add 15wt% lithium hexafluoro phosphate, stir to
Lithium salts is completely dissolved, and in being transferred to the steel cylinder of nitrogen atmosphere, is labeled as embodiment 2 in case detection.
Electrolyte solution gas chromatograph, gas chromatograph-mass spectrometer detection：
Composition detection analysis is carried out to the electrolyte solution of embodiment 2 using gas chromatograph, testing result is as shown in Figure 6.
Impurity component analysis is carried out using same procedure in embodiment 1, and speculates poly- in lithium hexafluoro phosphate electrolyte solution
Product state double bond compound structure chart.
Knowable to Fig. 1 and Fig. 2 compare, add in electrolyte solution and build up after state double bond compound, electrolyte solution gas phase
There are two impurity peaks in chromatograph testing result, and the time of staying is respectively 2.722 and 2.963, and it is molten that its composition should belong to electrolyte
The product that fractions mutual reactance is generated in liquid；In testing result Fig. 6 of embodiment 2, also occur in that near 2.865min
Same impurity peaks.
Qualitative analyses are carried out to the impurity component occurred in embodiment 1 by gas chromatograph-mass spectrometer, Fig. 3 shows two kinds of impurity point
Wei not cyclohexene and fluoro hexamethylene.
Verify by two kinds of contamination levels sample feedings that gas chromatograph is analyzed to Fig. 3, two kinds of marks in Fig. 4 and Fig. 5
The quasi- sample time of staying is respectively two impurity time of staying in 2.704 and 2.953, with Fig. 2 and just coincide, this result evidence
Two kinds of impurity component precisions of analysis.In wherein Fig. 5 the time of staying be 2.703 impurity peaks correspond to fluoro hexamethylene standard
A small amount of cyclohexene in sample.
According to testing result in figure 1 above ~ Fig. 6, understand with reference to the detection method principle of the present invention, embodiment 1 and implement
Electrolyte solution adds micro N, N'- dicyclohexylcarbodiimides in example 2.
It is more than illustrating for section Example of the invention, is not intended to limit the scope of the claims of the present invention,
All change or replacement without departing from present invention, all should be within protection scope of the present invention.
Claims (5)
1. in a kind of lithium hexafluoro phosphate electrolyte solution build up state double bond compound detection method, it is characterised in that include with
Lower step：
A. electrolyte solution sealing preserve：
By lithium hexafluoro phosphate electrolyte solution sealing preserve to be detected in the steel cylinder of nitrogen atmosphere, 2 ~ 60 are placed under room temperature
My god, accumulation state double bond compound is fully reacted；
B. gas chromatograph-mass spectrometer qualitative analyses trace impurity composition：
Qualitative analyses are carried out to the electrolyte solution composition after placement by gas chromatograph-mass spectrometer, to confirm hexafluorophosphoric acid lithium electrolyte
Whether containing the trace impurity composition beyond conventional ingredient in solution；
C. gas chromatograph standard sample sample introduction checking：
By trace impurity standard sample difference sample introduction checking of the gas chromatograph to detecting in electrolyte solution and step b,
With impurity component reliability in verification step b, and it is double reversely to speculate whether lithium hexafluoro phosphate electrolyte solution added accumulation state
Key compound.
2. the detection method of state double bond compound is built up in lithium hexafluoro phosphate electrolyte solution according to claim 1, its
It is characterised by, accumulation state double bond compound has any one shown in Formulas I ~ formula III in the lithium hexafluoro phosphate electrolyte solution
Plant structure：
Formulas I
Formula II
Formula III
Wherein, R1~R4Independently represent that straight chained alkyl, branched alkyl, nitrogen that carbon number is 2 ~ 15 replace branched alkyl, ring
Shape alkyl or aromatic radical.
3. the detection method of state double bond compound is built up in lithium hexafluoro phosphate electrolyte solution according to claim 1, its
It is characterised by, state double bond compound is built up in the lithium hexafluoro phosphate electrolyte solution for N, N '-dicyclohexylcarbodiimide,
N, N '-DIC and 1- (3- dimethylaminopropyls) -3- ethyl carbodiimides, phenylisocyanate, toluene
Any one in diisocyanate, '-diphenylmethane diisocyanate, hexamethylene diisocyanate.
4. the detection method of state double bond compound is built up in lithium hexafluoro phosphate electrolyte solution according to claim 1, its
It is characterised by, the detection range that state double bond compound is built up in the lithium hexafluoro phosphate electrolyte solution is 50 ~ 2000ppm.
5. the detection method of state double bond compound is built up in lithium hexafluoro phosphate electrolyte solution according to claim 1, its
It is characterised by, places 3 ~ 15 days under electrolyte solution room temperature in step a.
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