Method for detecting components of 1, 4-bis (4-phenoxy benzoyl) benzene reaction liquid by high performance liquid chromatography

Abstract

The invention discloses a method for detecting components of a 1, 4-bis (4-phenoxy benzoyl) benzene reaction solution by high performance liquid chromatography, which belongs to the technical field of analysis and detection methods, and the set chromatographic analysis conditions are as follows: separation by adopting a C18 chromatographic column subjected to end capping treatment, detection by adopting a diode array detector, and detection by adopting a chromatographic column subjected to end capping treatment. The contents of paraphthaloyl chloride, diphenyl ether, 1, 4-bis (4-phenoxybenzoyl) benzene (EKKE), EKKE ortho-isomer, 4-(4-phenoxybenzoyl) benzoic acid and 4-(4-phenoxybenzoyl) benzoate are simultaneously determined by using a single-point external standard method, and a determination method is provided for central control analysis and reaction endpoint judgment in a synthesis process of the 1, 4-bis (4-phenoxybenzoyl) benzene. The method is high in separation degree; the accuracy rate of a determination result is high, and the recovery rate of each substance is within the range of 95-105%; result repeatability RSD is less than 2%, and repeatability is good.

Description

Technical Field

[0001] The invention belongs to the technical field of analysis and detection methods, and specifically is a method for detecting components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction liquid by a high performance liquid chromatography method. Background Art

[0002] Polyetheretherketone (PEEK), an advanced, high-performance engineering thermoplastic, belongs to the polyaryletherketone (PEEK) material family. Its molecular structure, characterized by the regular alternation of rigid benzene rings with flexible ether bonds and ketone groups, achieves a unique combination of rigidity and flexibility. The rigid benzene rings impart exceptional mechanical strength, high-temperature resistance, radiation resistance, and chemical stability, while the flexible ether bonds enable the material to be molded using conventional thermoplastic processes such as extrusion and injection molding. This unique balance of properties has led to significant application in high-end applications such as aerospace (metal replacement and weight reduction), medical implants (biocompatibility), and new energy vehicles (high-temperature-resistant electronic components).

[0003] In the two-step synthesis process for polyetherketoneketone (PEK) developed by DuPont, the key intermediate, 1,4-bis(4-phenoxybenzoyl)benzene (EKKE), is first synthesized through the precisely controlled Friedel-Crafts acylation reaction of terephthaloyl chloride and diphenyl ether under Lewis acid catalysis. Subsequently, the target polymer is obtained by regulating the co-condensation reaction of EKKE with isophthaloyl chloride and terephthaloyl chloride. This process significantly improves production efficiency and process controllability. Therefore, the yield of the intermediate EKKE generated in the first step and the content of byproduct impurities are key control parameters that determine the yield and purity of the final product, polyetherketoneketone (PEK), in the second step. Therefore, in addition to tracking the raw material conversion rate and product yield during the synthesis process, it is also necessary to measure the amount of byproducts generated to provide a basis for product quality control. There is no existing technology for simultaneously determining the contents of terephthaloyl chloride, diphenyl ether, 1,4-bis(4-phenoxybenzoyl)benzene (EKKE), EKKE ortho-isomers, 4-(4-phenoxybenzoyl)benzoic acid, and 4-(4-phenoxybenzoyl)benzoate in the 1,4-bis(4-phenoxybenzoyl)benzene synthesis reaction liquid. Summary of the Invention

[0004] To solve the above problems, the purpose of the present invention is to provide a method for detecting the components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction solution by high performance liquid chromatography.

[0005] To achieve the above-mentioned purpose, the present invention is implemented through the following technical solutions: A method for detecting the components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction solution by high performance liquid chromatography is disclosed. The process is as follows: a sample is dissolved in a mixed solution of methanol and dichloromethane in a volume ratio of 1:1, and then determined by high performance liquid chromatography. The mobile phase is a methanol and acetic acid aqueous solution for gradient elution, and a C18 chromatographic column with end-capping treatment is used for separation. A diode array detector is used for detection, and the content is calculated by a single-point external standard method.

[0006] The method for detecting the components of the 1,4-bis(4-phenoxybenzoyl)benzene reaction solution by high performance liquid chromatography specifically comprises the following steps: 1) Preparation of mixed standard solution: Weigh 5±0.0005 mg of the standard substances terephthaloyl chloride, 10±0.0005 mg of diphenyl ether, 5±0.0005 mg of the ortho-isomer of EKKE, 5±0.0005 mg of 4-(4-phenoxybenzoyl)benzoic acid, 5±0.0005 mg of 4-(4-phenoxybenzoyl)benzoate, and 10±0.0005 mg of 1,4-bis(4-phenoxybenzoyl)benzene into a 50 mL volumetric flask. Dissolve in a 1:1 (volume ratio) mixture of methanol and dichloromethane, dilute to the mark, and shake well to obtain the mixed standard solution. 2) Preparation of sample solution: Accurately weigh 0.2 ± 0.0005 g of sample and place it in a 25 mL volumetric flask. Add a 1:1 volume ratio of methanol and dichloromethane. Dissolve the sample by ultrasonication, then dilute to the mark and shake well to obtain the sample solution. 3) Set chromatographic analysis conditions; 4) Determination of mixed standard solution: The mixed standard solution prepared in step 1) was subjected to HPLC determination, and the peak area A of each group in the standard solution was recorded. s ; 5) Determination of sample solution: The sample solution prepared in step 2) was subjected to high performance liquid chromatography and the peak area A of each component was recorded. i , calculate the content of group components using the single-point external standard method; The calculation formula is as follows:

[0007] Where: w i is the mass fraction of terephthaloyl chloride, diphenyl ether, 1,4-bis(4-phenoxybenzoyl)benzene, EKKE ortho-isomer, 4-(4-phenoxybenzoyl)benzoic acid and 4-(4-phenoxybenzoyl)benzoate in the sample, unit is %; A i is the peak area of ​​each component in the sample; A s is the peak area of ​​each group of standard products; m i is the sample mass in g; m sis the mass of the standard, in g; Ps is the purity of the standard, in %.

[0008] The chromatographic analysis conditions in step 3) are: Chromatographic column: Shim-pack GIST C18-AQ column, specifications: 150 mm × 4.6 mm, 3 μm; Flow rate: 0.5-0.7 mL / min; Elution mode: gradient elution; Detector: diode array detector; Detection wavelength: 240nm±5nm; Column temperature: 30~40℃; Injection volume: 5-10 μL; Mobile phase A: 0.1% acetic acid-water solution, filtered and ultrasonically prepared; Mobile phase B: chromatographic grade methanol.

[0009] The gradient elution conditions are as follows: Time (min) Mobile phase A (%) Mobile phase B (%) 0 40~30 60~70 10 15~5 85~95 25 15~5 85~95 25.01 40~30 60~70 35 40~30 60~70 Preferably, the gradient elution conditions are as follows: Time (min) Mobile phase A (%) Mobile phase B (%) 0 30 70 10 5 95 25 5 95 25.01 30 70 35 30 70 Compared with the prior art, the present invention has the following advantages: The invention discloses a method for detecting components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction liquid by using a high-performance liquid chromatography method. The method can rapidly and accurately determine the contents of terephthaloyl chloride, diphenyl ether, 1,4-bis(4-phenoxybenzoyl)benzene (EKKE), an ortho-isomer of EKKE, 4-(4-phenoxybenzoyl)benzoic acid, and 4-(4-phenoxybenzoyl)benzoate in the reaction liquid. The method has high separation, high accuracy of the determination result, and a recovery rate of each substance within a range of 95-105%. The result repeatability has an RSD of less than 2%, good repeatability, and low limits of quantification and detection. The method has important practical significance for tracking the reaction process, studying the reaction mechanism, and controlling product quality, and provides a quality control method for a 1,4-bis(4-phenoxybenzoyl)benzene synthesis process. BRIEF DESCRIPTION OF THE DRAWINGS

[0010] Figure 1 This is a liquid chromatogram of a mixed standard under the analytical conditions described in Example 1 of the present invention; Figure 2 This is a liquid chromatogram of a mixed standard under the analytical conditions described in Example 5 of the present invention; In the figure, 1—terephthaloyl chloride; 2—4-(4-phenoxybenzoyl)benzoic acid; 3—diphenyl ether; 4—4-(4-phenoxybenzoyl)benzoate; 5—1,4-bis(4-phenoxybenzoyl)benzene; 6—EKKE ortho isomer. DETAILED DESCRIPTION

[0011] In order to better understand the technical solutions of the present invention, the following is a further detailed description of the above content of the present invention through specific implementation methods in the form of examples. However, this should not be construed as limiting the scope of the above subject matter of the present invention to the following examples. All technologies implemented based on the above content of the present invention fall within the scope of the present invention.

[0012] The instrument used in the following examples was an LC-20AD liquid chromatograph (Shimadzu).

[0013] The sample in the present invention is solution 2 obtained according to step 2) of the method of patent CN 119241820A.

[0014] Example 1 1) Preparation of a mixed standard solution: Weigh 5 mg of standard substances: terephthaloyl chloride, 10 mg of diphenyl ether, 5 mg of the ortho-isomer of EKKE, 5 mg of 4-(4-phenoxybenzoyl)benzoic acid, 5 mg of 4-(4-phenoxybenzoyl)benzoate, and 10 mg of 1,4-bis(4-phenoxybenzoyl)benzene (EKKE), place the mixture in a 50 mL volumetric flask, dissolve the mixture in a 1:1 volume ratio of methanol and dichloromethane, dilute to the mark, and shake to obtain a mixed standard solution. 2) Preparation of sample solutions: Accurately weigh 0.2 g each of samples 1#, 2#, and 3#, place in a 25 mL volumetric flask, add a 1:1 volume ratio of methanol and dichloromethane, sonicate to dissolve, dilute to the mark, and shake well to obtain three sample solutions. 3) Set the chromatographic analysis conditions: Chromatographic column: Shim-pack GIST C18-AQ column, specifications: 150 mm × 4.6 mm, 3 μm; Flow rate: 0.6 mL / min; Elution mode: gradient elution; Detector: diode array detector; Detection wavelength: 242nm; Column temperature: 35°C; Injection volume: 5 μL; Mobile phase A: 0.1% acetic acid-water solution, filtered and ultrasonically prepared; Mobile phase B: chromatographic grade methanol.

[0015] Gradient elution conditions were as follows: Time (min) Mobile phase A (%) Mobile phase B (%) 0 30 70 10 5 95 25 5 95 25.01 30 70 35 30 70 4) Determination of mixed standard solution: The mixed standard solution prepared in step 1) was subjected to high performance liquid chromatography. The detection spectrum is as follows: Figure 1 As shown, record the peak area A of each group in the standard solution s ; 5) Determination of sample solution: The sample solution prepared in step 2) was subjected to high performance liquid chromatography and the peak area A of each component was recorded. i The content of each component was calculated using the single-point external standard method, and the test results are shown in Table 1.

[0016] Table 1 Sample test results Sample number Terephthaloyl chloride diphenyl ether EKKE EKKE ortho isomer 4-(4-phenoxybenzoyl)benzoic acid 4-(4-phenoxybenzoyl)benzoate 1# 0.239% 3.22% 4.99% 0.169% 0.0087% 0.0240% 2# 0.0154% 1.34% 5.45% 0.203% 0.0108% 0.0435% 3# 0.0163% 1.92% 5.35% 0.210% 0.0121% 0.0458% Example 2 Sample 3# was measured three times using the method and steps in Example 1, and the test results are shown in Table 2. As can be seen from the results in Table 2, using the test method of the present invention, the repeatability RSD of the determination results of the content of each component was less than 2%, indicating good repeatability.

[0017] Table 2 Repeatability test results of sample 3# Number of repetitions Terephthaloyl chloride diphenyl ether EKKE EKKE ortho isomer 4-(4-phenoxybenzoyl)benzoic acid 4-(4-phenoxybenzoyl)benzoate 1 0.0165% 1.918% 5.343% 0.208% 0.0123% 0.0459% 2 0.0162% 1.920% 5.351% 0.208% 0.0120% 0.0463% 3 0.0163% 1.929% 5.354% 0.214% 0.0120% 0.0453% average value 0.0163 % 1.92% 5.35% 0.210% 0.0121% 0.0458% RSD (%) 0.94 0.30 0.11 1.65 1.43 1.10 Example 3: Accurately weigh 0.1g of sample 3# (9 portions) and place them in 25mL volumetric flasks. 1mL, 5mL, and 10mL of the mixed standard solution from Example 1 were added, respectively. A 1:1 volume ratio of methanol and dichloromethane was then added. After ultrasonic dissolution, the volume was adjusted to the mark and shaken well. This was used as the spiked test solution. Three portions were prepared in parallel for each concentration. Testing was performed according to the method and steps in Example 1, and the recovery was calculated. The results are shown in Table 3. As can be seen from the results in Table 3, the recovery of each component was within the range of 95% to 105%, indicating that this method has good accuracy.

[0018] Table 3 Test results of recovery rate of each component

[0019] Example 4 1) Preparation of mixed standard stock solution: Weigh 25 mg of standard substances, including terephthaloyl chloride, 50 mg of diphenyl ether, 25 mg of the ortho-isomer of EKKE, 25 mg of 4-(4-phenoxybenzoyl)benzoic acid, 25 mg of 4-(4-phenoxybenzoyl)benzoate, and 50 mg of 1,4-bis(4-phenoxybenzoyl)benzene (EKKE), place in a 50 mL volumetric flask, dissolve with dichloromethane, dilute to the mark, and shake well to obtain a mixed standard stock solution; 2) Preparation of mixed standard solutions with gradient content: Pipette 1.00mL, 2.00mL, 4.00mL, 8.00mL, 10.00mL and 12.00mL of the mixed standard stock solution into a 50mL volumetric flask, dissolve it with a mixture of methanol and dichloromethane in a volume ratio of 1:1, ultrasonically dissolve it, dilute to the mark, and shake well to obtain terephthaloyl chloride, EKKE ortho-isomer, 4-(4-phenoxybenzoyl)benzoic acid and 4-(4-phenoxybenzoyl)benzoic acid. The ester mass concentrations were 0.01 mg / mL, 0.02 mg / mL, 0.04 mg / mL, 0.08 mg / mL, 0.1 mg / mL, and 0.12 mg / mL; the mixed standard solutions of diphenyl ether and 1,4-bis(4-phenoxybenzoyl)benzene (EKKE) mass concentrations were 0.02 mg / mL, 0.04 mg / mL, 0.08 mg / mL, 0.16 mg / mL, 0.2 mg / mL, and 0.24 mg / mL; 3) Detection was performed according to the chromatographic analysis conditions in Example 1; 4) Standard Curve Establishment: A standard curve was established based on the correspondence between chromatographic peak area and the mass concentration of the solvent in the mixed standard solution with a gradient content. By continuously decreasing the concentration of the standard solution, a signal-to-noise ratio (S / N) of 3 was set as the detection limit, and a signal-to-noise ratio (S / N) of 10 was set as the quantification limit. The results are shown in Table 4. As can be seen from the results in Table 4, each component exhibited a good linear relationship within the corresponding concentration range.

[0020] Table 4 Standard curve determination results Component name Concentration linear range (µg / mL) Linear equations Correlation coefficient Detection limit (µg / mL) Limit of quantification (µg / mL) Terephthaloyl chloride 10.4~125.0 y = 102960969x + 68356 0.9996 0.0783 0.261 diphenyl ether 18.3~292.8 y = 22477729x + 162630 0.9996 0.330 1.10 EKKE 20.2~242.4 y = 42638090x - 72898 0.9996 0.243 0.811 EKKE ortho isomer 9.92~119.0 y = 41393659x - 6668 0.9998 0.316 1.05 4-(4-phenoxybenzoyl)benzoic acid 9.65~115.8 y = 49876658x - 11285 0.9991 0.159 0.530 4-(4-phenoxybenzoyl)benzoate 9.70~116.4 y = 57392030x + 137013 0.9990 0.116 0.388 Example 5 In this example, step 1) preparation of the mixed standard solution and step 2) preparation of the sample solution are the same as those in Example 1.

[0021] 3) Set the chromatographic analysis conditions: Chromatographic column: Shim-pack GIST C18-AQ column, specifications: 150 mm × 4.6 mm, 3 μm; Flow rate: 0.6 mL / min; Elution mode: gradient elution; Detector: diode array detector; Detection wavelength: 242nm; Column temperature: 35°C; Injection volume: 5 μL; Mobile phase A: 0.1% acetic acid-water solution, filtered and ultrasonically prepared; Mobile phase B: chromatographic grade methanol.

[0022] Gradient elution conditions were as follows: Time (min) Mobile phase A (%) Mobile phase B (%) 0 40 60 10 5 95 25 5 95 25.01 40 60 35 40 60 4) Determination of mixed standard solution: The mixed standard solution prepared in step 1) was subjected to high performance liquid chromatography. The detection spectrum is as follows: Figure 2 As shown, record the peak area A of each group in the standard solution s ; 5) Determination of sample solution: The sample solution prepared in step 2) was subjected to high performance liquid chromatography and the peak area A of each component was recorded. i The single-point external standard method was used to calculate the content of the components in the group, and the test results are shown in Table 5. It can be seen from the results in Table 5 that this method can achieve baseline separation between the component to be tested and the adjacent components under different gradient elution conditions, thereby ensuring the accuracy of the analysis results.

[0023] Table 5 Sample test results Sample number Terephthaloyl chloride diphenyl ether EKKE EKKE ortho isomer 4-(4-phenoxybenzoyl)benzoic acid 4-(4-phenoxybenzoyl)benzoate 1# 0.241% 3.20% 4.92% 0.171% 0.0087% 0.0243% 2# 0.0150% 1.35% 5.52% 0.205% 0.0109% 0.0429% 3# 0.0165% 1.92% 5.33% 0.216% 0.0117% 0.0461% Example 6 1) Preparation of a mixed standard solution: Weigh 5 mg of the standard substances terephthaloyl chloride, 10 mg of diphenyl ether, 5 mg of the ortho-isomer of EKKE, 5 mg of 4-(4-phenoxybenzoyl)benzoic acid, 5 mg of 4-(4-phenoxybenzoyl)benzoate, and 10 mg of 1,4-bis(4-phenoxybenzoyl)benzene (EKKE), place the solution in a 50 mL volumetric flask, dissolve the solution in a 1:1 volume ratio of methanol and dichloromethane, dilute to the mark, and shake to obtain a mixed standard solution. 2) Preparation of sample solution: Accurately weigh 0.2 g of sample 1# and place it in a 25 mL volumetric flask. Add a 1:1 volume ratio of methanol and dichloromethane. Dissolve the sample by ultrasonication, then dilute to the mark and shake well to obtain the sample solution. 3) Set the chromatographic analysis conditions: Chromatographic column: Shim-pack GIST C18-AQ column, specifications: 150 mm × 4.6 mm, 3 μm; Flow rate: 0.5 mL / min; Elution mode: gradient elution; Detector: diode array detector; Detection wavelength: 240nm; Column temperature: 30°C; Injection volume: 8 μL; Mobile phase A: 0.1% acetic acid-water solution, filtered and ultrasonically prepared; Mobile phase B: chromatographic grade methanol.

[0024] Gradient elution conditions were as follows: Time (min) Mobile phase A (%) Mobile phase B (%) 0 35 65 10 10 90 25 10 90 25.01 35 65 35 35 65 4) Determination of mixed standard solution: The mixed standard solution prepared in step 1) was subjected to HPLC determination, and the peak area A of each group in the standard solution was recorded. s ; 5) Determination of sample solution: The sample solution prepared in step 2) was subjected to high performance liquid chromatography and the peak area A of each component was recorded. i The content of each component was calculated using the single-point external standard method, and the test results are shown in Table 6.

[0025] Table 6 Sample test results Sample number Terephthaloyl chloride diphenyl ether EKKE EKKE ortho isomer 4-(4-phenoxybenzoyl)benzoic acid 4-(4-phenoxybenzoyl)benzoate 1# 0.240% 3.21% 4.95% 0.172% 0.0085% 0.0242% Example 7 1) Preparation of a mixed standard solution: Weigh 5 mg of the standard substances terephthaloyl chloride, 10 mg of diphenyl ether, 5 mg of the ortho-isomer of EKKE, 5 mg of 4-(4-phenoxybenzoyl)benzoic acid, 5 mg of 4-(4-phenoxybenzoyl)benzoate, and 10 mg of 1,4-bis(4-phenoxybenzoyl)benzene (EKKE), place the solution in a 50 mL volumetric flask, dissolve the solution in a 1:1 volume ratio of methanol and dichloromethane, dilute to the mark, and shake to obtain a mixed standard solution. 2) Preparation of sample solution: Accurately weigh 0.2 g of sample 2# and place it in a 25 mL volumetric flask. Add a 1:1 volume ratio of methanol and dichloromethane. Dissolve the sample by ultrasonication, then dilute to the mark and shake well to obtain the sample solution. 3) Set the chromatographic analysis conditions: Chromatographic column: Shim-pack GIST C18-AQ column, specifications: 150 mm × 4.6 mm, 3 μm; Flow rate: 0.7 mL / min; Elution mode: gradient elution; Detector: diode array detector; Detection wavelength: 245nm; Column temperature: 40°C; Injection volume: 10 μL; Mobile phase A: 0.1% acetic acid-water solution, filtered and ultrasonically prepared; Mobile phase B: chromatographic grade methanol.

[0026] Gradient elution conditions were as follows: Time (min) Mobile phase A (%) Mobile phase B (%) 0 30 70 10 15 85 25 5 95 25.01 35 65 35 30 70 4) Determination of mixed standard solution: The mixed standard solution prepared in step 1) was subjected to HPLC determination, and the peak area A of each group in the standard solution was recorded. s ; 5) Determination of sample solution: The sample solution prepared in step 2) was subjected to high performance liquid chromatography and the peak area A of each component was recorded.i The content of each component was calculated using the single-point external standard method, and the test results are shown in Table 7.

[0027] Table 7 Sample test results Sample number Terephthaloyl chloride diphenyl ether EKKE EKKE ortho isomer 4-(4-phenoxybenzoyl)benzoic acid 4-(4-phenoxybenzoyl)benzoate 2# 0.0152% 1.34% 5.52% 0.203% 0.0106% 0.0431% Although the above describes the specific implementation methods of the present invention, it does not limit the scope of protection of the present invention. Based on the technical solution of the present invention, various modifications or variations that can be made by those skilled in the art without creative work are still within the scope of protection of the present invention.

Claims

1. A method for detecting components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction solution by high performance liquid chromatography, characterized in that: The process is as follows: the sample is dissolved in a mixed solution of methanol and dichloromethane in a volume ratio of 1:1, and then determined by high performance liquid chromatography. The mobile phase is methanol and acetic acid aqueous solution for gradient elution, and a capped C18 chromatographic column is used for separation. A diode array detector is used for detection, and the content is calculated by the single-point external standard method.

2. The method for detecting the components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction solution by high performance liquid chromatography according to claim 1, wherein: The specific steps include: 1) Preparation of mixed standard solution: Weigh 5±0.0005 mg of the standard substances terephthaloyl chloride, 10±0.0005 mg of diphenyl ether, 5±0.0005 mg of the ortho-isomer of EKKE, 5±0.0005 mg of 4-(4-phenoxybenzoyl)benzoic acid, 5±0.0005 mg of 4-(4-phenoxybenzoyl)benzoate, and 10±0.0005 mg of 1,4-bis(4-phenoxybenzoyl)benzene into a 50 mL volumetric flask. Dissolve in a 1:1 (volume ratio) mixture of methanol and dichloromethane, dilute to the mark, and shake well to obtain the mixed standard solution. 2) Preparation of sample solution: Accurately weigh 0.2 ± 0.0005 g of sample and place it in a 25 mL volumetric flask. Add a 1:1 volume ratio of methanol and dichloromethane. Dissolve the sample by ultrasonication, then dilute to the mark and shake well to obtain the sample solution. 3) Set chromatographic analysis conditions; 4) Determination of mixed standard solution: The mixed standard solution prepared in step 1) was subjected to HPLC determination, and the peak area A of each group in the standard solution was recorded. s ; 5) Determination of sample solution: The sample solution prepared in step 2) was subjected to high performance liquid chromatography and the peak area A of each component was recorded. i , calculate the content of group components using the single-point external standard method; The calculation formula is as follows: Where: w i is the mass fraction of terephthaloyl chloride, diphenyl ether, 1,4-bis(4-phenoxybenzoyl)benzene, EKKE ortho-isomer, 4-(4-phenoxybenzoyl)benzoic acid and 4-(4-phenoxybenzoyl)benzoate in the sample, unit is %; A i is the peak area of ​​each component in the sample; A s is the peak area of ​​each group of standard products; m i is the sample mass in g; m s is the mass of the standard, in g; Ps is the purity of the standard, in %.

3. The method for detecting the components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction solution by high performance liquid chromatography according to claim 2, wherein: The chromatographic analysis conditions in step 3) are: Chromatographic column: Shim-pack GIST C18-AQ column, specifications: 150 mm × 4.6 mm, 3 μm; Flow rate: 0.5-0.7 mL / min; Elution mode: gradient elution; Detector: diode array detector; Detection wavelength: 240nm±5nm; Column temperature: 30-40°C; Injection volume: 5~10μL; Mobile phase A: 0.1% acetic acid-water solution, filtered and ultrasonically prepared; Mobile phase B: chromatographic grade methanol.

4. The method for detecting components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction solution by high performance liquid chromatography according to claim 3, wherein: The gradient elution conditions are as follows: 。 5. The method for detecting components of a 1,4-bis(4-phenoxybenzoyl)benzene reaction solution by high performance liquid chromatography according to claim 3, wherein: The gradient elution conditions are as follows: 。

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