CN114591374A - Compound, synthesis method thereof and method for detecting hydrogen ion concentration in lithium battery - Google Patents

Compound, synthesis method thereof and method for detecting hydrogen ion concentration in lithium battery Download PDF

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CN114591374A
CN114591374A CN202210133752.XA CN202210133752A CN114591374A CN 114591374 A CN114591374 A CN 114591374A CN 202210133752 A CN202210133752 A CN 202210133752A CN 114591374 A CN114591374 A CN 114591374A
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裴锋
田旭
刘欣
贾蕗路
左曜
徐碧川
周世阳
邓辰星
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State Grid Corp of China SGCC
Electric Power Research Institute of State Grid Jiangxi Electric Power Co Ltd
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Electric Power Research Institute of State Grid Jiangxi Electric Power Co Ltd
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Abstract

The invention discloses a compound and a synthetic method thereof, and the structural formula is

Description

Compound, synthesis method thereof and method for detecting hydrogen ion concentration in lithium battery
Technical Field
The invention relates to the field of lithium battery detection, in particular to a compound, a synthetic method thereof and a method for detecting the concentration of hydrogen ions in a lithium battery.
Background
Nowadays, lithium ion batteries are widely applied in our lives, the application fields of the lithium ion batteries comprise mobile phones, computers, electric tools and the like, and with the increasingly wide application of intelligent living goods, the future intelligent living goods will also be important fields for applying the lithium ion batteries, so that various index tests of the lithium ion batteries are particularly important.
The components of the lithium ion battery non-aqueous electrolyte comprise hydrofluoric acid, and the trace amount of hydrofluoric acid in the lithium ion battery non-aqueous electrolyte has great influence on the capacity, the cycle life and the safety of the battery, so that the content of the hydrofluoric acid must be strictly monitored in the production, storage, transportation and manufacturing processes of the lithium battery electrolyte. At present, BTB is mainly used as an indicator for measuring hydrogen fluoride in a non-aqueous system, and a visual inspection method is used for judging an end point, so that a large error is brought to an indicator method.
In nature, certain bacteria, archaea and eukaryotes have a metalloenzyme known as hydrogenase, which catalyzes the reduction of protons to release hydrogen and the oxidation of hydrogen. Due to the compound [ Fe2(CO)6(μ-SR)2]And [ FeFe ]]The structure of the hydrogenase active center has a high degree of similarity,it has been found that such compounds are also capable of catalyzing the reduction of protons to release hydrogen.
Disclosure of Invention
The present invention is directed to at least one of the technical problems of the prior art, and provides a new method for detecting the hydrogen ion concentration in a lithium battery. The invention synthesizes [2Fe2S containing basic pyridine functional group]Nuclear hydrogenase model Compound 1{ Fe2(CO)5[(μ-SCH2)2C(CH3)(2-Py)]And (6) measuring the hydrogen ion concentration in the lithium ion battery non-aqueous electrolyte by using the catalyst through electrochemical cyclic voltammetry analysis.
The technical solution of the invention is as follows:
a compound having the formula:
Figure BDA0003503646730000011
the synthesis method of the compound comprises the following steps:
(1) under the protection of Ar, dissolving dodecacarbonyl ferroferric oxide in toluene, then adding the solution into a toluene solution containing 2-methyl-2-propyl bipyridyl-1, 3-dithiol, heating and refluxing for reaction for 3.5-4.5 h, and removing the solvent under reduced pressure to obtain residue;
(2) separating the residue by column chromatography, collecting to obtain dark green solution, and removing solvent under reduced pressure to obtain dark green solid;
(3) dissolving the dark green solid in acetonitrile, filtering to remove insoluble substances, removing part of solution under reduced pressure, and freezing at-15-25 ℃ for 1-3 days to obtain dark green crystals.
In a specific embodiment of the invention, in the step (1), under the protection of Ar, 0.35-0.45 mmol of ferroferric dodecacarbonyl is dissolved in 4-6 ml of dry toluene, then the solution is added into 8-12 ml of toluene solution containing 2-methyl-2-propyl bipyridyl-1, 3-dithiol, the temperature is heated to 105-115 ℃, and reflux reaction is carried out for 3.5-4.5 hours.
In the specific embodiment of the invention, in the step (1), 0.4mmol of ferroferric dodecacarbonyl is dissolved in 5ml of dry toluene, and then the solution is added into 10ml of toluene solution containing 2-methyl-2-propyl bipyridyl-1, 3-dithiol, heated to 110 ℃, and refluxed for 4 hours.
In a specific embodiment of the present invention, in the step (2), the developing agent for column chromatography is a mixed solution of n-hexane and ethyl acetate in a volume ratio of 4:1, and the stationary phase is silica gel.
In a specific embodiment of the present invention, in the step (3), the frozen food is frozen at-20 ℃ for 2 days.
The method for detecting the hydrogen ion concentration in the lithium battery by adopting the compound comprises the following steps:
s1, preparing electrolyte standard solutions containing hydrofluoric acid with different concentrations, adding the compound of claim 1 into the standard solutions, respectively performing electrochemical cyclic voltammetry scanning on each standard solution to respectively obtain cyclic voltammetry curves of each standard solution, and plotting the concentration of the hydrofluoric acid and corresponding points of peak current values of the cyclic voltammetry curves to obtain a linear equation between the concentration of the hydrofluoric acid and the current intensity;
s2, preparing a liquid to be tested, adding the compound of claim 1 into the liquid to be tested, performing electrochemical cyclic voltammetry scanning on the liquid to be tested to obtain a cyclic voltammetry curve of the liquid to be tested, and substituting the peak current value of the cyclic voltammetry curve of the liquid to be tested into a linear equation of a standard solution to calculate the concentration of hydrofluoric acid in the liquid to be tested.
In a specific embodiment of the invention, 3-5 mmol of the compound is added to the standard solution and the solution to be tested respectively.
In an embodiment of the present invention, in step S1, a linear equation between the concentration of the hydrofluoric acid and the current intensity is "y" is 8.23x +14.1, where x is the concentration of the hydrofluoric acid and y is the current intensity.
The invention has at least one of the following beneficial effects:
the invention synthesizes [2Fe2S containing basic pyridine functional group]Nuclear hydrogenase model compound { Fe2(CO)5[(μ-SCH2)2C(CH3)(2-Py)]Which is capable of catalyzing protonsReducing, namely, taking the compound as a catalyst, catalyzing the reduction of protons (namely hydrofluoric acid) in a lithium battery, testing the cyclic voltammetry curve of a standard solution containing HF by using an electrochemical cyclic voltammetry method, and plotting the concentration of the HF and the corresponding point of the peak current value of the cyclic voltammetry curve to obtain a linear equation, wherein the peak current and the HF concentration have a better linear relation, R is a linear relation299.6 percent, and the lowest detection limit is 0.3 mM; and then, testing the cyclic voltammetry curve of the solution to be tested by using an electrochemical cyclic voltammetry method, and substituting the peak current of the solution to be tested into a linear equation to calculate the detection value in the solution to be tested. The detection method is simple and convenient and has high accuracy.
Drawings
FIG. 1 is a cyclic voltammogram of each standard solution in example 1;
FIG. 2 is a graph of the concentration of hydrofluoric acid in the standard solution versus current intensity for example 1.
Detailed Description
A synthetic method of a compound for detecting hydrogen ion concentration in a lithium battery comprises the following steps:
(1) under the protection of Ar, dissolving 0.35-0.45 mmol of ferroferric dodecacarbonyl in 4-6 ml of dry toluene, then adding 8-12 ml of toluene solution containing 0.4mmol (0.079g) of 2-methyl-2-propyl bipyridine-1, 3-dithiol, heating to 105-115 ℃, carrying out reflux reaction for 3.5-4.5 h, and removing the solvent under reduced pressure to obtain residue; preferably, 0.4mmol of ferroferric dodecacarbonyl is dissolved in 5ml of dry toluene, then added into 10ml of toluene solution containing 2-methyl-2-propylbipyridine-1, 3-dithiol, heated to 110 ℃, refluxed for 4h, and the solvent is removed under reduced pressure to obtain residue.
(2) Separating the residue by column chromatography, collecting to obtain dark green solution, and removing solvent under reduced pressure to obtain dark green solid. Wherein, the developing agent for column chromatography is a mixed solution of normal hexane and ethyl acetate with the volume ratio of 4:1, and the stationary phase is silica gel.
(3) Dissolving the dark green solid in 5ml acetonitrile, filtering to remove insoluble substances, removing part of the solution under reduced pressure, freezing at-15-25 deg.C for 1-3 days, preferablyOptionally freezing at-20 deg.C for 2 days to obtain dark green crystal, analyzing the crystal components by element analysis and X-ray crystal diffraction technique to infer that the crystal is [2Fe2S ] containing basic pyridine functional group]Nuclear hydrogenase model Compound { Fe2(CO)5[(μ-SCH2)2C(CH3)(2-Py)]The structural formula is shown as follows:
Figure BDA0003503646730000031
the method for measuring the hydrogen ion concentration in the non-aqueous electrolyte of the lithium ion battery by using the compound as a catalyst and utilizing electrochemical cyclic voltammetry analysis specifically comprises the following steps:
s1, preparing electrolyte standard solutions containing hydrofluoric acid with different concentrations, adding the compound into the standard solutions as a catalyst, respectively performing electrochemical cyclic voltammetry scanning on each standard solution to respectively obtain cyclic voltammetry curves of each standard solution, and drawing corresponding points of the concentration (x) of the hydrofluoric acid contained in each standard solution and the peak current value (namely current intensity y) of the cyclic voltammetry curves to obtain a linear equation between x and y.
S2, preparing a liquid to be tested, adding the compound to be used as a catalyst into the liquid to be tested, respectively carrying out electrochemical cyclic voltammetry scanning on the liquid to be tested to obtain a cyclic voltammetry curve of the liquid to be tested, substituting the peak current value of the cyclic voltammetry curve of the liquid to be tested, namely the current intensity y into a linear equation, and calculating the value x to detect the hydrogen ion concentration in the liquid to be tested.
The present invention will be described in further detail with reference to the following examples, but the present invention is not limited to the following examples.
Example 1
Under the protection of Ar, 0.4mmol (0.216g) of ferroferric dodecacarbonyl is dissolved in 5ml of dry toluene, then 10ml of toluene solution containing 0.4mmol (0.079g) of 2-methyl-2-propyl bipyridine-1, 3-dithiol is added, the mixture is heated to 110 ℃, reflux reaction is carried out for 4h, and the solvent is removed under reduced pressure to obtain residue;
(2) separating the residue by column chromatography, collecting to obtain dark green solution, and removing solvent under reduced pressure to obtain dark green solid; wherein, the developing agent for column chromatography separation is a mixed solution of normal hexane and ethyl acetate with the volume ratio of 4:1, and the stationary phase is silica gel.
(3) The dark green solid was dissolved in 5ml of acetonitrile, insoluble matter was removed by filtration, a part of the solution was removed under reduced pressure, the mixture was frozen at-20 ℃ for two days to give dark green crystals, and the composition of the crystals was analyzed by elemental analysis and X-ray crystal diffraction technique, and the structure of the crystals was presumed to be as follows:
Figure BDA0003503646730000041
the method for measuring the hydrogen ion concentration in the non-aqueous electrolyte of the lithium ion battery by using the crystal as a catalyst and utilizing electrochemical cyclic voltammetry analysis specifically comprises the following steps:
s1, preparing a hydrofluoric acid standard solution: 50.00g of lithium ion battery (lithium salt: LiPF) was weighed6) The electrolyte solution of (1) is dissolved by 400ml of ethylene carbonate solvent, the volume is fixed to 1000ml of solution, 6 parts of 150ml of solution are transferred to an electrochemical experimental cell, 4.0mmol of catalyst is respectively added, hydrofluoric acid with different concentrations (1.00mM, 2.00mM, 3.00mM, 4.00mM and 5.00mM) is added to 5 parts of the solution, and hydrofluoric acid is not added to the other part of the solution to be used as a blank control group, so as to obtain standard solutions with different hydrofluoric acid concentrations.
Making a standard curve: electrochemical cyclic voltammetry scans were performed on each standard solution, and cyclic voltammetry curves of each solution were obtained as shown in fig. 1. As can be seen from fig. 1, as the HF concentration increases, the peak current of cyclic voltammetry also gradually increases.
Then, the concentration of hydrofluoric acid is plotted against the peak current value of the cyclic voltammogram, and as shown in fig. 2, a linear relation between the concentration (x) of hydrofluoric acid and the current intensity (y) is obtained, and the linear equation is that y is 8.23x + 14.1. It can be seen from FIG. 2 that the peak current is in a better linear relationship with the HF concentration, R299.6% with a minimum detection limit of 0.3mM, so that the method can test the electrolyte of a lithium ion battery (Non-aqueous) of different hydrogen ion concentrations.
S2, preparing a test solution: preparing a solution to be tested by the same method as the step S1, numbering the solution to be tested as No. 1 (hydrofluoric acid concentration 0.30mM), No. 2 (1.00mM), No. 3 (2.50mM), No. 4 (4.50mM), No. 5 (10.00mM) and No. 6 (15.00mM), adding 4.0mmol of catalyst, performing electrochemical cyclic voltammetry scanning on 5 parts of solution to be tested to obtain 5 parts of cyclic voltammetry curves of the solution to be tested, substituting the peak current value of the cyclic voltammetry curves of the 5 parts of solution to be tested, namely the current intensity y, into the linear equation of the standard solution to calculate the hydrogen ion concentration in the 5 parts of solution to be tested, wherein the results are shown in Table 1:
TABLE 1
Detection value of hydrogen ion concentration Actual value of hydrogen ion concentration Error of
No. 1 liquid to be tested 0.29mM 0.30mM -3.30%
No. 2 liquid to be tested 1.02mM 1.00mM +2.00%
No. 3 liquid to be tested 2.53mM 2.50mM +1.20%
No. 4 liquid to be tested 4.49mM 4.50mM -0.22%
No. 5 liquid to be tested 10.03mM 10.00mM +0.30%
No. 6 liquid to be tested 14.98mM 15.00mM -0.13%
As can be seen from table 1, the errors between the detected value of the hydrogen ion concentration in the test solutions No. 1 to No. 6 obtained by the method of the present invention and the actual value of the hydrogen ion concentration (hydrofluoric acid concentration) were all within a range of 5%, which indicates that the method of the present invention can accurately detect the hydrogen ion concentration in the nonaqueous electrolyte solution of the lithium ion battery.
The above are merely characteristic embodiments of the present invention, and do not limit the scope of the present invention in any way. All technical solutions formed by equivalent exchanges or equivalent substitutions fall within the protection scope of the present invention.

Claims (10)

1. A compound having the formula:
Figure FDA0003503646720000011
2. a method of synthesizing a compound as claimed in claim 1, comprising the steps of:
(1) under the protection of Ar, dissolving dodecacarbonyl ferroferric oxide in toluene, then adding the solution into a toluene solution containing 2-methyl-2-propyl bipyridyl-1, 3-dithiol, heating and refluxing for reaction for 3.5-4.5 h, and removing the solvent under reduced pressure to obtain residue;
(2) separating the residue by column chromatography, collecting to obtain dark green solution, and removing solvent under reduced pressure to obtain dark green solid;
(3) dissolving the dark green solid in acetonitrile, filtering to remove insoluble substances, removing part of solution under reduced pressure, and freezing at-15-25 ℃ for 1-3 days to obtain dark green crystals.
3. The method for synthesizing the compound according to claim 2, wherein in the step (1), under the protection of Ar, 0.35-0.45 mmol of ferroferric dodecacarbonyl is dissolved in 4-6 ml of dry toluene, then the solution is added into 8-12 ml of toluene solution containing 2-methyl-2-propyl bipyridyl-1, 3-dithiol, the temperature is heated to 105-115 ℃, and the reflux reaction is carried out for 3.5-4.5 hours.
4. The method for synthesizing the compound according to claim 2, wherein in the step (1), 0.4mmol of ferroferric carbonyl is dissolved in 5ml of dry toluene, and then the solution is added into 10ml of toluene solution containing 2-methyl-2-propyl bipyridyl-1, 3-dithiol, heated to 110 ℃, and refluxed and reacted for 4 hours.
5. The method for synthesizing the compound according to claim 2, wherein in the step (2), the developing solvent for column chromatography is a mixed solution of n-hexane and ethyl acetate in a volume ratio of 4:1, and the stationary phase is silica gel.
6. The method for synthesizing a compound according to claim 2, wherein in the step (3), the mixture is frozen at-20 ℃ for 2 days.
7. A method for detecting the concentration of hydrogen ions in a lithium battery using the compound of claim 1, comprising the steps of:
s1, preparing electrolyte standard solutions containing hydrofluoric acid with different concentrations, adding the compound of claim 1 into the standard solutions, respectively performing electrochemical cyclic voltammetry scanning on each standard solution to respectively obtain cyclic voltammetry curves of each standard solution, and plotting the concentration of the hydrofluoric acid and corresponding points of peak current values of the cyclic voltammetry curves to obtain a linear equation between the concentration of the hydrofluoric acid and the current intensity;
s2, preparing a liquid to be tested, adding the compound of claim 1 into the liquid to be tested, performing electrochemical cyclic voltammetry scanning on the liquid to be tested to obtain a cyclic voltammetry curve of the liquid to be tested, and substituting the peak current value of the cyclic voltammetry curve of the liquid to be tested into a linear equation of a standard solution to calculate the concentration of hydrofluoric acid in the liquid to be tested.
8. The method for detecting the hydrogen ion concentration in a lithium battery as claimed in claim 7, wherein 3 to 5mmol of the compound of claim 1 is added to the standard solution and the solution to be tested, respectively.
9. The method for detecting hydrogen ion concentration in a lithium battery as claimed in claim 7, wherein 4mmol of the compound according to claim 1 is added to each of the standard solution and the solution to be tested.
10. The method of claim 7, wherein in step S1, a linear equation between the concentration of hydrofluoric acid and the current intensity is "8.23 x +14.1, where x is the concentration of hydrofluoric acid and y is the current intensity.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2194127A1 (en) * 1996-12-30 1998-06-30 Christophe Michot Delocalized anions for use as electrolytic solutes
US20070039833A1 (en) * 2005-08-19 2007-02-22 Fih Co., Ltd Method for measuring corrosion inhibitor concentration
CN109651446A (en) * 2019-01-23 2019-04-19 广西师范大学 A kind of list phosphine replaces bridging azepine propane bridge iron iron hydrogenation catalator object and its synthetic method and application
CN116675721A (en) * 2023-06-07 2023-09-01 桂林师范高等专科学校 Carbon propane bridged iron-iron hydrogenase model, and synthetic method and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2194127A1 (en) * 1996-12-30 1998-06-30 Christophe Michot Delocalized anions for use as electrolytic solutes
US20070039833A1 (en) * 2005-08-19 2007-02-22 Fih Co., Ltd Method for measuring corrosion inhibitor concentration
CN109651446A (en) * 2019-01-23 2019-04-19 广西师范大学 A kind of list phosphine replaces bridging azepine propane bridge iron iron hydrogenation catalator object and its synthetic method and application
CN116675721A (en) * 2023-06-07 2023-09-01 桂林师范高等专科学校 Carbon propane bridged iron-iron hydrogenase model, and synthetic method and application thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
FENFEN XU,等: "Controlling carbon monoxide binding at di-iron units related to the iron-only hydrogenase sub-site", CHEMICAL COMMUNICATIONS, vol. 24, no. 05, pages 606 *
ZHIMEI LI,等: "Enhancement in catalytic proton reduction by an internal base in a diiron pentacarbonyl complex: its synthesis, characterisation, inter-conversion and electrochemical investigation", DALTON TRANSACTIONS, vol. 46, no. 06, pages 1865 *
ZHIYIN XIAO,等: "Synthesis, Characterization, Protonation and Electrochemical Investigation of Diiron Tetracarbonyl Complex as a Model of [FeFe]-Hydrogenase", ASIAN JOURNAL OF CHEMISTRY, vol. 24, no. 01, pages 250 *

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