Method for determining purity of 1, 3-propanedisulfonyl fluoride

Abstract

The invention relates to a detection method for determining the purity of 1, 3-propanedisulfonyl fluoride, which is used for establishing an analysis method for determining the purity of a 1, 3-propanedisulfonyl fluoride sample by gas chromatography, and comprises the following steps: preparing a working solution of a standard substance and a working solution of a to-be-detected substance; the method comprises the following steps: respectively testing a working solution of a standard substance and a working solution of a to-be-tested substance by adopting a gas chromatographic method to obtain test results of the standard substance and the to-be-tested substance under specific conditions, testing working solutions of 1, 3-propanedisulfonyl fluoride standard substances with different solute-solvent mass ratios to obtain corresponding test results, and then carrying out curve fitting on a standard sample. And testing a working solution of a sample to be tested under the same condition, and substituting the tested working solution into the fitting function, so as to calculate the purity of the sample to be tested. The method has the advantages of simple operation, high precision and good stability, and can accurately determine the corresponding chromatographic test purity of 1, 3-propanedisulfonyl fluoride.

Description

Technical Field

[0001] This invention relates to the field of fluorochemical product analysis and testing technology, and in particular to a method for determining the purity of 1,3-propanedisulfonyl fluoride. Background Technology

[0002] 1,3-Propanedisulfonyl fluoride is a white solid with a strong, pungent odor at room temperature and pressure. It is highly corrosive and extremely toxic. Its molecular weight is 216.19, melting point is 156–164℃, boiling point is 268–276℃, and critical temperature is approximately 184℃. It readily reacts with water, acids, and alkalis to form the corresponding 1,3-propanedisulfonic acid and 1,3-propanedisulfonate.

[0003] In recent years, with the continuous development of the lithium battery industry, the industry's demands for the quality of battery electrolytes have been constantly increasing. As the lifeblood of lithium batteries, the composition of the electrolyte is closely related to the performance of the lithium battery. To improve battery performance, some fluorine-containing organic compounds are often used as electrolyte additives to improve the performance of lithium batteries. Among them, sulfonyl fluorides are commonly used as electrolyte additives in the lithium battery industry. Related studies have shown that 1,3-propanedisulfonyl fluoride can significantly improve the stability of electrode materials, thereby significantly improving the electrochemical performance and lifespan of the battery. However, there are currently no national or industry standards for determining the purity of 1,3-propanedisulfonyl fluoride. Therefore, there is an urgent need for an analytical method and approach to solve the above-mentioned technical problems. Summary of the Invention

[0004] To address the shortcomings of existing technologies, the present invention aims to provide a simple and easy-to-implement gas chromatography method for determining the purity of 1,3-sulfonyl fluoride, thus solving the problem of insufficient current techniques for determining the purity of 1,3-propanedisulfonyl fluoride. This invention can detect the content of 1,3-propanedisulfonyl fluoride in a single step, with high detection efficiency and advantages such as ease of implementation, good repeatability, and high accuracy.

[0005] To achieve the above objectives, the technical solution of the present invention is as follows:

[0006] A method for determining the purity of 1,3-propanedisulfonyl fluoride includes the following steps:

[0007] S1: Preparation of 1,3-propanedisulfonyl fluoride standard sample solution and test sample solution;

[0008] S2: Gas chromatography (GC) was used to test the 1,3-propanedisulfonyl fluoride standard sample and the sample to be tested, and the results of the standard sample solution and the sample to be tested solution were obtained.

[0009] S3: Perform qualitative analysis on the determination results of the standard sample solution to determine the peak positions of the corresponding 1,3-propanedisulfonyl fluoride and solvent.

[0010] S4: Based on the corresponding peak positions of 1,3-propanedisulfonyl fluoride and solvent obtained in S3 above, standard curve fitting is performed on the determination results of standard sample solutions with different ratios to obtain the functional relationship between the mass of 1,3-propanedisulfonyl fluoride, the mass of solvent and the peak area of ​​1,3-propanedisulfonyl fluoride and the peak area of ​​solvent.

[0011] S5: Based on the test results of the sample to be tested and the functional relationship obtained in step S3, the purity of 1,3-propanedisulfonyl fluoride in the sample solution to be tested is calculated.

[0012] Preferably, the solvent used to prepare the solution in step S1 is acetonitrile.

[0013] Preferably, the concentration of the sample solution to be tested in step S1 is 1-2 g / g solution; the mass ratio of different formulations including 1,3-propanedisulfonyl fluoride standard sample to solvent in step S4 is 1-10:10.

[0014] Preferably, the gas chromatography conditions in step S2 are as follows: column type: Aglient DB-1, 30m × 0.32mm × 1μm; carrier gas flow rate: 20–50mL / min; gas flow rate: 15–40L / min; oxidizing gas flow rate: 200–400mL / min; column temperature: 180–240℃; injection port temperature: 180–250℃; split ratio: 10–20:1; injection volume: 0.5–1.0μL; detector: flame ionization detector (FID), temperature: 260–330℃.

[0015] Preferably, the stationary phase of the Aglient DB-1 column is 100% dimethylpolysiloxane.

[0016] Preferably, the column temperature is increased by a programmed temperature increase: the initial temperature is 80-100℃, held for 2-5 minutes; then the temperature is increased to 240-280℃ at a rate of 5-10℃ / min, and held for 2-5 minutes.

[0017] Preferably, the carrier gas is nitrogen; the fuel gas is hydrogen; and the combustion-supporting gas is air.

[0018] Preferably, the detector for the gas chromatograph is a flame ionization detector, and the detector temperature is 200–280°C.

[0019] Preferably, the functional relationship between the mass of the 1,3-propanedisulfonyl fluoride standard sample, the solvent mass, the peak area of ​​1,3-propanedisulfonyl fluoride, and the peak area of ​​the solvent is as follows:

[0020]

[0021] Where m 溶剂 The mass of the solvent standard in the standard solution;

[0022] m 1,3-丙二磺酰氟 The mass of 1,3-propanedisulfonyl fluoride standard in the standard solution;

[0023] A 1,3-丙二磺酰氟 The peak area of ​​1,3-propanedisulfonyl fluoride standard in the standard solution;

[0024] A 溶剂 This represents the peak area of ​​the solvent standard in the standard solution;

[0025] k is a constant obtained by fitting the gas phase measurement results of the standard solution.

[0026] Preferably, the purity of 1,3-propanedisulfonyl fluoride in the sample solution to be tested is calculated using the following formula:

[0027]

[0028] Where m 溶剂 The mass of the solvent standard in the sample solution to be tested;

[0029] m 样品 The mass of 1,3-propanedisulfonyl fluoride standard in the sample solution to be tested;

[0030] A 样品 The peak area of ​​the 1,3-propanedisulfonyl fluoride standard in the sample solution to be tested is shown.

[0031] A 溶剂 This represents the peak area of ​​the solvent standard in the sample solution to be tested;

[0032] k is a constant obtained by fitting the gas phase measurement results of the standard solution.

[0033] The beneficial effects of this invention are:

[0034] This invention discloses a method for determining the purity of 1,3-propanedisulfonyl fluoride, which is simple to operate, highly accurate, and stable. It can accurately determine the chromatographic purity of 1,3-propanedisulfonyl fluoride, thus filling the gap in the analytical techniques for 1,3-propanedisulfonyl fluoride. Attached Figure Description

[0035] To more clearly illustrate the relevant technical solutions of the embodiments of the present invention, the accompanying drawings of the embodiments will be briefly described below.

[0036] Figure 1 This is the gas chromatogram of the sample solution to be tested in Example 1;

[0037] Figure 2This is the gas chromatogram of the sample solution to be tested in Example 2.

[0038] Specific implementation cases

[0039] The technical solutions of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the specific embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of the present invention.

[0040] Example 1

[0041] A method for determining the purity of 1,3-propanedisulfonyl fluoride includes the following steps:

[0042] (1) Preparation of 1,3-propanedisulfonyl fluoride-acetonitrile mixed standard solution

[0043] Accurately weigh 0.1 g, 0.2 g, 0.4 g, 0.8 g, and 1.0 g of 1,3-propanedisulfonyl fluoride standard, respectively, to the nearest 0.001 g; dissolve each in 1.0 g of acetonitrile standard, to the nearest 0.001 g, and shake well to obtain mixed standard solutions of different gradients.

[0044] (2) Preparation of the sample solution to be tested

[0045] Weigh 0.501g of sample and dissolve it in 1.003g of acetonitrile, accurate to 0.001g, and shake well to obtain the sample solution to be tested.

[0046] (3) Measurement

[0047] Gas chromatography was used to test the standard solution and the sample solution to be tested, and the gas chromatography results of the standard solution and the sample solution to be tested were obtained.

[0048] The hardware conditions for the gas chromatography described include: an Aglient DB-1 column with a stationary phase of 100% dimethylpolysiloxane (30m × 0.32mm × 1μm); nitrogen as the carrier gas at a flow rate of 20–50 mL / min; hydrogen as the fuel gas at a flow rate of 15–40 L / min; air as the combustion-supporting gas at a flow rate of 200–400 mL / min; programmed temperature ramping with an initial temperature of 100℃, held for 5 min, and then ramped to 240℃ at a rate of 10℃ / min, held for 2 min; injection port temperature of 220℃; split ratio of 10:1; injection volume of 1.0 μL; and a flame ionization detector (FID) at a temperature of 260℃.

[0049] (4) Determine the fit of the standard curve.

[0050] Based on the gas chromatographic determination results of the 1,3-propanedisulfonyl fluoride-acetonitrile mixed standard solution, the relationship between the mass of 1,3-propanedisulfonyl fluoride, the mass of acetonitrile, and the peak area was obtained by fitting the standard curve, as shown in Table 1:

[0051] Table 1

[0052]

[0053]

[0054] Where m 乙腈 This refers to the mass of acetonitrile standard in the standard solution;

[0055] m 丙二磺酰胺 The mass of 1,3-propanedisulfonyl fluoride standard in the standard solution;

[0056] A 1,3-丙二磺酰氟 The peak area of ​​1,3-propanedisulfonyl fluoride standard in the standard solution;

[0057] A 乙腈 This represents the peak area of ​​the acetonitrile standard in the standard solution;

[0058] k is a constant obtained by fitting the gas phase measurement results of the standard solution.

[0059] The constant representing the relationship between the mass and peak area of ​​the two substances, obtained through fitting calculation, is: k = 3.8119.

[0060] (4) Calculate the purity of 1,3-propanedisulfonyl fluoride in the sample to be tested.

[0061] The results of the gas chromatography analysis of the sample solution are as follows: Figure 1 As shown, the retention time for acetonitrile is 3.868 min, with a peak area of ​​89.035%; the retention time for 1,3-propanedisulfonyl fluoride is 7.719 min, with a peak area of ​​10.905%. Substituting these data into the formula for calculating the chromatographic purity of 1,3-propanedisulfonyl fluoride:

[0062]

[0063] The purity of 1,3-propanedisulfonyl fluoride in the sample was calculated to be 93.37%.

[0064] Example 2

[0065] A method for determining the purity of 1,3-propanedisulfonyl fluoride includes the following steps:

[0066] (1) Preparation of 1,3-propanedisulfonyl fluoride-acetonitrile mixed standard solution

[0067] Accurately weigh 0.107 g, 0.208 g, 0.411 g, 0.805 g, and 1.030 g of 1,3-propanedisulfonyl fluoride standard, respectively, to the nearest 0.001 g; dissolve each in 1.0 g of acetonitrile standard, to the nearest 0.001 g, and shake well to obtain mixed standard solutions of different gradients.

[0068] (2) Preparation of the sample solution to be tested

[0069] Weigh 0.427g of sample and dissolve it in 1.051g of acetonitrile, accurate to 0.001g, and shake well to obtain the sample solution to be tested.

[0070] (3) Measurement

[0071] Gas chromatography was used to test the standard solution and the sample solution to be tested, and the gas chromatography results of the standard solution and the sample solution to be tested were obtained.

[0072] The hardware conditions for the gas chromatography described include: an Aglient DB-1 column with a stationary phase of 100% dimethylpolysiloxane (30m × 0.32mm × 1μm); nitrogen as the carrier gas at a flow rate of 20–50 mL / min; hydrogen as the fuel gas at a flow rate of 15–40 L / min; air as the combustion-supporting gas at a flow rate of 200–400 mL / min; programmed temperature ramping with an initial temperature of 100℃, held for 5 min, and then ramped to 220℃ at a rate of 10℃ / min, held for 3 min; injection port temperature of 210℃; split ratio of 10:1; injection volume of 1.0 μL; and a flame ionization detector (FID) at a temperature of 240℃.

[0073] (4) Determine the fit of the standard curve.

[0074] Based on the gas chromatographic determination results of the 1,3-propanedisulfonyl fluoride-acetonitrile mixed standard solution, the relationship between the mass of 1,3-propanedisulfonyl fluoride, the mass of acetonitrile, and the peak area was obtained by fitting the standard curve, as shown in Table 2:

[0075] Table 2

[0076]

[0077] The constant representing the relationship between the mass and peak area of ​​the two substances, obtained through fitting calculation, is: k = 3.8319.

[0078] (4) Calculate the purity of 1,3-propanedisulfonyl fluoride in the sample to be tested.

[0079] The results of the gas chromatography analysis of the sample solution are as follows: Figure 2As shown, the retention time for acetonitrile is 4.030 min, with a peak area of ​​90.960%; the retention time for 1,3-propanedisulfonyl fluoride is 13.366 min, with a peak area of ​​9.045%. Substituting these data into the formula for calculating the chromatographic purity of 1,3-propanedisulfonyl fluoride:

[0080]

[0081] The purity of 1,3-propanedisulfonyl fluoride in the sample was calculated to be 93.35%.

[0082] By comparing Example 1 and Example 2, the purity error of 1,3-propanedisulfonyl fluoride in the samples measured by both examples does not exceed 0.1%, indicating that the test method provided by the present invention has high accuracy and good stability.

[0083] It should be noted that all the above embodiments belong to the same inventive concept, and the descriptions of each embodiment have different focuses. Where the description in a particular embodiment is not detailed, please refer to the description in other embodiments.

[0084] The embodiments described above are merely illustrative of implementation methods of the present invention, and while the descriptions are specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the protection scope of the present invention. Therefore, the protection scope of this invention patent should be determined by the appended claims.

Claims

1. A method for determining the purity of 1,3-propanedisulfonyl fluoride, characterized in that, Includes the following steps: S1: Preparation of 1,3-propanedisulfonyl fluoride standard sample solution and test sample solution; S2: Gas chromatography (GC) was used to test the 1,3-propanedisulfonyl fluoride standard sample and the sample to be tested, and the results of the standard sample solution and the sample to be tested solution were obtained. S3: Perform qualitative analysis on the determination results of the standard sample solution to determine the peak positions of the corresponding 1,3-propanedisulfonyl fluoride and solvent. S4: Based on the corresponding peak positions of 1,3-propanedisulfonyl fluoride and solvent obtained in S3 above, standard curve fitting is performed on the determination results of standard sample solutions with different ratios to obtain the functional relationship between the mass of 1,3-propanedisulfonyl fluoride, the mass of solvent and the peak area of ​​1,3-propanedisulfonyl fluoride and the peak area of ​​solvent. S5: Based on the test results of the sample to be tested and the functional relationship obtained in step S3, the purity of 1,3-propanedisulfonyl fluoride in the sample solution to be tested is calculated.

2. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 1, characterized in that, The solvent used to prepare the solution in step S1 is acetonitrile.

3. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 1, characterized in that, The concentration of the sample solution to be tested in step S1 is 1-2 g / g solution; In step S4, the different formulations include 1,3-propanedisulfonyl fluoride standard samples: the mass ratio of solvent to solvent is 1 to 10:

10.

4. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 1, characterized in that, The gas chromatography conditions described in step S2 are as follows: column type: Aglient DB-1, 30m × 0.32mm × 1μm; carrier gas flow rate: 20–50mL / min; gas flow rate: 15–40L / min; oxidizing gas flow rate: 200–400mL / min; column temperature: 180–240℃; injection port temperature: 180–250℃; split ratio: 10–20:1; injection volume: 0.5–1.0μL; detector: flame ionization detector (FID), temperature: 260–330℃.

5. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 4, characterized in that, The stationary phase of the Aglient DB-1 column is 100% dimethylpolysiloxane.

6. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 4, characterized in that, The column temperature is increased as follows: programmed temperature increase: initial temperature is 80-100℃, held for 2-5 min; then increased to 240-280℃ at a rate of 5-10℃ / min, held for 2-5 min.

7. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 4, characterized in that, The carrier gas is nitrogen; the fuel gas is hydrogen; and the combustion-supporting gas is air.

8. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 4, characterized in that, The gas chromatograph uses a flame ionization detector with a detector temperature of 200–280 °C.

9. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 1, characterized in that, The functional relationship between the mass of the 1,3-propanedisulfonyl fluoride standard sample, the solvent mass, the peak area of ​​1,3-propanedisulfonyl fluoride, and the peak area of ​​the solvent is as follows: Where m 溶剂 The mass of the solvent standard in the standard solution; m 1,3-丙二磺酰氟 The mass of the 1,3-propanedisulfonyl fluoride standard sample in the standard solution; A 1,3-丙二磺酰氟 The peak area of ​​the 1,3-propanedisulfonyl fluoride standard sample in the standard solution; A 溶剂 This represents the peak area of ​​the solvent standard in the standard solution; k is a constant obtained by fitting the gas phase measurement results of the standard solution.

10. The method for determining the purity of 1,3-propanedisulfonyl fluoride according to claim 9, characterized in that, The purity of 1,3-propanedisulfonyl fluoride in the sample solution to be tested is calculated using the following formula: Where m 溶剂 The mass of the solvent standard in the sample solution to be tested; m 样品 The mass of 1,3-propanedisulfonyl fluoride standard in the sample solution to be tested; A 样品 The peak area of ​​the 1,3-propanedisulfonyl fluoride standard in the sample solution to be tested is shown. A 溶剂 This represents the peak area of ​​the solvent standard in the sample solution to be tested; k is a constant obtained by fitting the gas phase measurement results of the standard solution.

Images