A method for synthesizing tri(p-tolyl)thionium hexafluorophosphate
By employing Grignard reaction and recrystallization processes, the problem of low yield in the synthesis of tri(p-tolyl)thionium hexafluorophosphate was solved, achieving high-yield and high-purity product preparation suitable for large-scale production.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- HEBEI UNIV OF SCI & TECH
- Filing Date
- 2026-04-15
- Publication Date
- 2026-05-26
AI Technical Summary
Existing methods for synthesizing tri(p-tolyl)thionium hexafluorophosphate have low yields, high costs, and are difficult to produce on a large scale. They also produce a large number of mono- and di-substituted byproducts.
Tris(p-tolyl)thionium bromide was prepared by Grignard reaction of bis(4-chlorophenyl) sulfoxide and p-tolyl magnesium bromide in the presence of trimethylchlorosilane, and then by recrystallization with potassium hexafluorophosphate and ethyl acetate/n-hexane.
The yield of tri(p-tolyl)thionium hexafluorophosphate was increased to 71.34%. The raw materials are readily available, the activation conditions are mild, the production safety is high, the crystal form is improved, the oiling phenomenon is reduced, and the product purity is improved.
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Figure CN122079841A_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of chemical synthesis technology and relates to a method for synthesizing tri(p-tolyl)thionium hexafluorophosphate. Background Technology
[0002] Tris(p-tolyl)thionium hexafluorophosphate, as an organic compound, is widely used in medicine, dyes, optics, and other fields. Currently, the main synthetic methods for tris(p-tolyl)thionium hexafluorophosphate reported in the literature are as follows: The first synthetic method uses thionyl chloride as a substrate to synthesize tris(p-tolyl)thionium bromide via a Grignard reaction. In 2004, Shigeaki Imazeki et al. (Synthesis, 2004, 10(10): 1648-1654.) used thionyl chloride and p-tolyl magnesium bromide as raw materials and trimethylchlorosilane as an activator to finally prepare tris(p-tolyl)thionium bromide. The synthetic route is as follows: .
[0003] This synthetic route typically uses tetrahydrofuran as the reaction solvent and reacts at room temperature in the presence of trimethylchlorosilane to obtain the target product. However, this method produces a large number of mono- and di-substituted byproducts, resulting in low yield and poor purity, making it difficult to produce the product on a large scale.
[0004] The second synthetic method uses dimethyl sulfate as a substrate to synthesize tris(p-tolyl)thionium bromide via a Grignard reaction. In 2004, Shigeaki Imazeki et al. (Synthesis, 2004, 10(10): 1648-1654.) used dimethyl sulfate and p-tolyl magnesium bromide as raw materials and trimethylchlorosilane as an activator to finally prepare tris(p-tolyl)thionium bromide. The synthetic route is as follows: .
[0005] This synthetic route typically uses tetrahydrofuran as the reaction solvent and reacts at room temperature in the presence of trimethylchlorosilane to obtain the target product. However, this method results in a high cost of dimethyl sulfate, making it difficult to produce the product on a large scale. Furthermore, the presence of numerous mono- and di-substituted byproducts leads to low yields and poor purity.
[0006] Therefore, different synthesis methods have significant differences in yield and cost. Low-yield synthesis methods often mean increased costs and decreased product quality. Therefore, it is necessary to propose a high-yield synthesis method for tri(p-tolyl)thionium hexafluorophosphate. Summary of the Invention
[0007] To address the aforementioned technical problems, this invention aims to provide a method for synthesizing tris(p-tolyl)thionium hexafluorophosphate. This method uses inexpensive and readily available raw materials, employs mild activation conditions, and ensures high production safety. It solves the problem of low yield in the synthesis of tris(p-tolyl)thionium hexafluorophosphate in the prior art. The yield of tris(p-tolyl)thionium hexafluorophosphate obtained by this invention can reach up to 71.34%.
[0008] To achieve the above objectives, the technical solution adopted by the present invention is as follows: A method for synthesizing tri(p-tolyl)thionium hexafluorophosphate, comprising the following steps in sequence: S1. After mixing di(4-chlorophenyl) sulfoxide with solvent, p-tolyl magnesium bromide is slowly added under an inert atmosphere and stirred for 10 min. Trimethylchlorosilane is added dropwise at 20-30 °C and the reaction is continued for 10-12 h. After the reaction is completed, a 25 wt.% hydrobromic acid aqueous solution is added dropwise to quench the reaction and stirring is continued for 2 h. After extraction and vacuum concentration, tri(p-tolyl)thionium bromide is obtained. S2. Add an aqueous solution of potassium hexafluorophosphate to tri(p-tolyl)thionium bromide, stir and react. After the reaction is complete, filter and recrystallize the filter cake to obtain tri(p-tolyl)thionium hexafluorophosphate.
[0009] As a limitation of the present invention, in step S1, the solvent is one or more of tetrahydrofuran, diethyl ether, toluene, or xylene.
[0010] As another limitation of the present invention, in step S1, the mass-to-volume ratio of the di(4-chlorophenyl) sulfoxide to the solvent is 1:(8~10) g / mL.
[0011] As a third limitation of the present invention, in step S1, the molar ratio of bis(4-chlorophenyl) sulfoxide to p-tolyl magnesium bromide is 1:(4~6).
[0012] As a fourth limitation of the present invention, in step S1, the molar ratio of bis(4-chlorophenyl) sulfoxide to trimethylchlorosilane is 1:(3~5).
[0013] As a fifth limitation of the present invention, in step S1, the rate of adding trimethylchlorosilane is 0.5~0.8 mL / min.
[0014] As a sixth limitation of the present invention, in step S2, the concentration of the potassium hexafluorophosphate aqueous solution is 61.4 g / L; and the molar ratio of potassium hexafluorophosphate to di(4-chlorophenyl) sulfoxide in the potassium hexafluorophosphate aqueous solution is 2:1.
[0015] As a seventh limitation of the present invention, in step S2, the reaction temperature is 20 °C, the reaction time is 2 h, and the stirring rate is 800~1200 rpm.
[0016] As an eighth limitation of the present invention, in step S2, the solvent used for recrystallization is a mixture of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane in the mixture is 1:3; and the recrystallization temperature is 20~35 °C.
[0017] This invention uses ethyl acetate and n-hexane for recrystallization. Ethyl acetate is responsible for dissolution, and n-hexane is responsible for controlled precipitation, which improves the crystal form and reduces oiling, thereby increasing the yield of tri(p-tolyl)thionium hexafluorophosphate.
[0018] This invention uses bis(4-chlorophenyl) sulfoxide and p-tolyl magnesium bromide as raw materials. Under the action of trimethylchlorosilane, bis(4-chlorophenyl) sulfoxide undergoes a Grignard reaction and a substitution reaction with p-tolyl magnesium bromide to generate the intermediate tri(p-tolyl)thionium bromide. Following anion exchange and recrystallization, tri(p-tolyl)thionium hexafluorophosphate is generated. The specific synthetic route is as follows: .
[0019] The specific reaction mechanism of this synthesis method is as follows: (1) Activation step: The oxygen atom in bis(4-chlorophenyl) sulfoxide exhibits nucleophilicity due to its lone pair of electrons. This oxygen atom can attack the silicon atom in trimethylchlorosilane, which is partially positively charged due to the electron-withdrawing effect of the chlorine atom, and undergo a nucleophilic substitution reaction to generate a silylated oxonium intermediate. This process greatly activates the sulfur atom, making it more susceptible to attack by nucleophiles. From the perspective of electronic effects, trimethylchlorosilane effectively enhances the electrophilic activity of the sulfur atom by abstracting the electron density on the oxygen atom. (2) Nucleophilic substitution step: p-Tolyl Grignard reagent (such as p-Tolyl Magnesium Bromide) is a strong nucleophile. Its nucleophilic p-Tolyl carbanion attacks the positively charged sulfur center in the aforementioned active intermediate, resulting in an SN2 type nucleophilic substitution reaction. In this process, the phenyl group replaces the -TMS group to generate bis(4-chlorophenyl)p-Tolyl thiocation and hexamethyldisiloxane. (3) Aryl substitution step: The aryl carbanion of p-toluene magnesium bromide has strong nucleophilicity. After the sulfoxide is activated by trimethylchlorosilane, it can efficiently attack the sulfur atom and replace the two 4-chlorophenyl groups to generate tri(p-toluyl)thionium cation. (4) Anion exchange step: In the second step reaction system (nucleophilic substitution), the counterion paired with the thiocation is the anion related to TMSOBr or MgBr2, not simply the bromide ion. It is treated by the subsequent addition of hydrobromic acid aqueous solution to achieve anion exchange; the bromide ions provided by the hydrobromic acid aqueous solution combine with the tri-tolyl thiocation to form tri(p-tolyl)sulfur bromide. The bromide ions are then exchanged again with hexafluorophosphate anion to form the final target product tri(p-tolyl)sulfonium hexafluorophosphate.
[0020] The above-mentioned technical solution of the present invention is a whole in which each step is closely related and mutually influential, and together they determine the morphological characteristics and performance of the product.
[0021] The above technical solution has the following advantages or beneficial effects: 1. This invention solves the problem of low yield in the synthesis of tri(p-tolyl)thionium hexafluorophosphate, with a maximum yield of up to 71.34%; 2. The raw materials of this invention are cheap and readily available, the activation conditions are mild, and the production is highly safe. Ethyl acetate and n-hexane are used as recrystallization solutions. Ethyl acetate is responsible for dissolution, and n-hexane is responsible for controlled precipitation, which improves the crystal form, reduces oiling, and increases the yield of tri(p-tolyl)thionium hexafluorophosphate.
[0022] The technical solution of the present invention will be further described in detail below with reference to the accompanying drawings and specific embodiments. Attached Figure Description
[0023] Figure 1 The 1H NMR spectrum of tri(p-tolyl)thionium hexafluorophosphate prepared in Example 1 of this invention; Figure 2 The image shows the carbon NMR spectrum of tri(p-tolyl)thionium hexafluorophosphate prepared in Example 1 of this invention. Detailed Implementation
[0024] The following embodiments are merely some, not all, of the embodiments of the present invention. Therefore, the detailed descriptions of the embodiments provided below are not intended to limit the scope of the claimed invention, but merely to illustrate selected embodiments. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without inventive effort are within the scope of protection of the present invention.
[0025] In this invention, unless otherwise specified, all equipment and raw materials are commercially available or commonly used in the industry. The methods described in the following embodiments are conventional methods in the art, unless otherwise specified. Example 1
[0026] This embodiment prepares a tri(p-tolyl)thionium hexafluorophosphate, and the preparation process and steps are as follows: S1. Di(4-chlorophenyl) sulfoxide (2.26 g, 8.35 mmol) was mixed with 22.6 mL of anhydrous tetrahydrofuran. Then, under an inert atmosphere, p-tolyl magnesium bromide (50.10 mL, 50.10 mmol) was slowly added. After stirring for 10 min, trimethylchlorosilane (4.54 g, 41.75 mmol) was added dropwise at 20 °C at a rate of 0.5 mL / min. The reaction was continued for 12 h. After the reaction was completed, a 25 wt.% aqueous solution of hydrobromic acid was added dropwise to quench the reaction. The mixture was stirred for 2 h. After extraction with dichloromethane and concentration under reduced pressure, tri(p-tolyl)thionium bromide was obtained. S2. Dissolve 3.07 g of potassium hexafluorophosphate in 50 mL of deionized water to form an aqueous solution of potassium hexafluorophosphate with a concentration of 61.4 g / L. Add the solution to tris(p-tolyl)thionium bromide and stir at 800 rpm at 20 °C for 2 h. After filtration, a white solid is obtained. Recrystallize the solid from a mixed solution of ethyl acetate and n-hexane in a volume ratio of 1:3 at 20 °C to obtain 2.68 g of tris(p-tolyl)thionium hexafluorophosphate, with a yield of 71.34%.
[0027] Figure 1 and Figure 2 The figures show the 1H NMR and 1C NMR spectra of the tri(p-tolyl)thionium hexafluorophosphate prepared in this embodiment. As can be seen from the figures, the prepared tri(p-tolyl)thionium hexafluorophosphate has no other obvious impurities and has high purity. Example 2
[0028] This embodiment prepares a tri(p-tolyl)thionium hexafluorophosphate, and the preparation process and steps are as follows: S1. Di(4-chlorophenyl) sulfoxide (2.26 g, 8.35 mmol) was mixed with 18.08 mL of anhydrous tetrahydrofuran. Then, under an inert atmosphere, p-tolyl magnesium bromide (33.4 mL, 33.4 mmol) was slowly added. After stirring for 10 min, trimethylchlorosilane (2.72 g, 25.05 mmol) was added dropwise at 30 °C at a rate of 0.8 mL / min. The reaction was continued for 12 h. After the reaction was completed, a 25 wt.% aqueous solution of hydrobromic acid was added dropwise to quench the reaction. The mixture was stirred for 2 h. After extraction with dichloromethane and concentration under reduced pressure, tri(p-tolyl)thionium bromide was obtained. S2. Dissolve 3.07 g of potassium hexafluorophosphate in 50 mL of deionized water to form an aqueous solution of potassium hexafluorophosphate with a concentration of 61.4 g / L. Add the solution to tris(p-tolyl)thionium bromide and stir at 1000 rpm at 20 °C for 2 h. After filtration, a white solid is obtained. Recrystallize the solid from a mixed solution of ethyl acetate and n-hexane in a volume ratio of 1:3 at 25 °C to obtain 2.46 g of tris(p-tolyl)thionium hexafluorophosphate, with a yield of 65.43%. Example 3
[0029] This embodiment prepares a tri(p-tolyl)thionium hexafluorophosphate, and the preparation process and steps are as follows: S1. Di(4-chlorophenyl) sulfoxide (2.26 g, 8.35 mmol) was mixed with 20 mL of anhydrous tetrahydrofuran. Under an inert atmosphere, p-tolyl magnesium bromide (41.75 mL, 41.75 mmol) was slowly added. After stirring for 10 min, trimethylchlorosilane (3.63 g, 33.40 mmol) was added dropwise at 25 °C at a rate of 0.6 mL / min. The reaction was continued for 10 h. After the reaction was completed, a 25 wt.% aqueous solution of hydrobromic acid was added dropwise to quench the reaction. The mixture was stirred for 2 h. After extraction with dichloromethane and concentration under reduced pressure, tri(p-tolyl)thionium bromide was obtained. S2. Dissolve 3.07 g of potassium hexafluorophosphate in 50 mL of deionized water to form an aqueous solution of potassium hexafluorophosphate with a concentration of 61.4 g / L. Add the solution to tris(p-tolyl)thionium bromide and stir at 1200 rpm at 20 °C for 2 h. After filtration, a white solid is obtained. Recrystallize the solid from a mixed solution of ethyl acetate and n-hexane in a volume ratio of 1:3 at 30 °C to obtain 2.54 g of tris(p-tolyl)thionium hexafluorophosphate, with a yield of 67.55%. Example 4
[0030] This embodiment prepares a tri(p-tolyl)thionium hexafluorophosphate, and the preparation process and steps are as follows: S1. Di(4-chlorophenyl) sulfoxide (2.26 g, 8.35 mmol) was mixed with 20 mL of anhydrous tetrahydrofuran. Then, under an inert atmosphere, p-tolyl magnesium bromide (50.10 mL, 50.10 mmol) was slowly added. After stirring for 10 min, trimethylchlorosilane (2.72 g, 25.05 mmol) was added dropwise at 25 °C at a rate of 0.7 mL / min. The reaction was continued for 12 h. After the reaction was completed, a 25 wt.% aqueous solution of hydrobromic acid was added dropwise to quench the reaction. The mixture was stirred for 2 h. After extraction with dichloromethane and concentration under reduced pressure, tri(p-tolyl)thionium bromide was obtained. S2. Dissolve 3.07 g of potassium hexafluorophosphate in 50 mL of deionized water to form an aqueous solution of potassium hexafluorophosphate with a concentration of 61.4 g / L. Add the solution to tris(p-tolyl)thionium bromide and stir at 20 °C for 2 h at a stirring rate of 800 rpm. After filtration, a white solid is obtained. Recrystallize the solid from a mixed solution of ethyl acetate and n-hexane in a volume ratio of 1:3 at 35 °C to obtain 2.42 g of tris(p-tolyl)thionium hexafluorophosphate, with a yield of 64.36%. Example 5
[0031] This embodiment prepares a tri(p-tolyl)thionium hexafluorophosphate, and the preparation process and steps are as follows: S1. Di(4-chlorophenyl) sulfoxide (2.26 g, 8.35 mmol) was mixed with 22.6 mL of anhydrous tetrahydrofuran. Then, under an inert atmosphere, p-tolyl magnesium bromide (33.4 mL, 33.4 mmol) was slowly added. After stirring for 10 min, trimethylchlorosilane (3.63 g, 33.4 mmol) was added dropwise at 30 °C at a rate of 0.6 mL / min. The reaction was continued for 11 h. After the reaction was completed, a 25 wt.% aqueous solution of hydrobromic acid was added dropwise to quench the reaction. The mixture was stirred for 2 h. After extraction with dichloromethane and concentration under reduced pressure, tri(p-tolyl)thionium bromide was obtained. S2. Dissolve 3.07 g of potassium hexafluorophosphate in 50 mL of deionized water to form an aqueous solution of potassium hexafluorophosphate with a concentration of 61.4 g / L. Add the solution to tris(p-tolyl)thionium bromide and stir at 800 rpm at 20 °C for 2 h. After filtration, a white solid is obtained. Recrystallize the solid from a mixed solution of ethyl acetate and n-hexane in a volume ratio of 1:3 at 20 °C to obtain 2.34 g of tris(p-tolyl)thionium hexafluorophosphate, with a yield of 62.23%.
[0032] Comparative Example 1 This comparative example uses the synthetic method described in the literature "Synthesis, 2004, 10(10):1648-1654." to prepare tris(p-tolyl)thionium bromide. The specific method and operation steps are as follows: Dimethyl sulfate (2.11 g, 16.7 mmol) was added to p-tolyl magnesium bromide (58 mL, 83.60 mmol, 1.45 mol / L) at room temperature, followed by the addition of trimethylchlorosilane (9.08 g, 83.6 mmol) while maintaining the temperature at 25 ± 5 °C. After the reaction was complete, the mixture was stirred for 30 min, and then the reaction was terminated by adding an aqueous hydrobromic acid solution. The organic layer was extracted with hydrobromic acid solution, the combined aqueous phases were extracted with dichloromethane, the combined dichloromethane layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The crude mixture was purified by recrystallization (isopropanol-n-hexane) to give 3.22 g of tri(p-tolyl)thionium bromide.
[0033] The yield of tri(p-tolyl)thionium bromide obtained by this synthetic method is 50%.
[0034] The yield of Example 1 of this invention is 21.34% higher than that of Comparative Example 1. The method of Comparative Example 1 uses dimethyl sulfate, which has a high cost, making it difficult to produce the product on a large scale. In addition, the method produces more mono- and di-substituted byproducts, resulting in low yield and poor purity.
[0035] Comparative Example 2 This comparative example uses the synthetic method described in the literature "Synthesis, 2004, 10(10):1648-1654." to prepare tris(p-tolyl)thionium bromide. The specific method and operation steps are as follows: Thionyl chloride (1.99 g, 16.7 mmol) was added to p-tolyl magnesium bromide (29 mL, 41.8 mmol, 1.45 mol / L) at room temperature, followed by the addition of trimethylchlorosilane (4.54 g, 41.8 mmol) while maintaining the temperature at 25 ± 5 °C. After the reaction was complete, the mixture was stirred for 30 minutes, and the reaction was terminated by adding an aqueous hydrobromic acid solution. The organic layer was extracted with hydrobromic acid solution. The combined aqueous phases were extracted with dichloromethane, and the combined dichloromethane layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The crude mixture was purified by recrystallization (isopropanol-n-hexane) to give 2.71 g of tri(p-tolyl)thionium bromide.
[0036] The yield of tri(p-tolyl)thionium bromide obtained by this synthetic method was 42%.
[0037] The yield of Example 1 was increased by 29.34% compared to Comparative Example 2. The method of Comparative Example 2 had more mono- and di-substituted byproducts, resulting in lower yield and poorer purity.
[0038] Comparative Example 3 This comparative example uses the synthetic method described in "Organic Chemistry, 1988, 53(53): 5571-5573." to prepare tris(p-tolyl)thionium bromide. The specific method and operation steps are as follows: Di(p-tolyl) sulfoxide (3.85 g, 16.7 mmol) was added to p-tolyl magnesium bromide (29 mL, 41.8 mmol, 1.45 mol / L) at room temperature, followed by the addition of trimethylsilyltrifluoromethanesulfonate (9.87 g, 41.8 mmol) while maintaining the temperature at 25 ± 5 °C. After the reaction was complete, the mixture was stirred for 30 minutes, and the reaction was terminated by adding an aqueous hydrobromic acid solution. The organic layer was extracted with hydrobromic acid solution. The combined aqueous phases were extracted with dichloromethane, and the combined dichloromethane layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The crude mixture was purified by recrystallization (isopropanol-n-hexane) to give 2.35 g of tri(p-tolyl)thionium bromide.
[0039] The yield of tri(p-tolyl)thionium bromide obtained by this synthetic method was 36.49%.
[0040] The yield of Example 1 of this invention is 34.85% higher than that of Comparative Example 3. The low yield is due to the weak activation effect of the activator trimethylsilyl trifluoromethanesulfonate in the method of Comparative Example 3.
[0041] Finally, it should be noted that the above descriptions are merely preferred embodiments of the present invention and are not intended to limit the present invention. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art can still modify the technical solutions described in the foregoing embodiments or make equivalent substitutions for some of the technical features. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the claims of the present invention.
Claims
1. A method for synthesizing tris(p-tolyl)thionium hexafluorophosphate, characterized in that, Follow these steps in sequence: S1. After mixing di(4-chlorophenyl) sulfoxide with solvent, p-tolyl magnesium bromide is slowly added under an inert atmosphere and stirred for 10 min. Trimethylchlorosilane is added dropwise at 20-30 °C and the reaction continues for 10-12 h. After the reaction is completed, a 25 wt.% hydrobromic acid aqueous solution is added dropwise to quench the reaction and stirring is continued for 2 h. After extraction and vacuum concentration, tri(p-tolyl)thionium bromide is obtained. S2. Add an aqueous solution of potassium hexafluorophosphate to tri(p-tolyl)thionium bromide, stir and react. After the reaction is complete, filter and recrystallize the filter cake to obtain tri(p-tolyl)thionium hexafluorophosphate.
2. The method for synthesizing tris(p-tolyl)thionium hexafluorophosphate according to claim 1, characterized in that, In step S1, the solvent is one or more of tetrahydrofuran, diethyl ether, toluene, or xylene.
3. The method for synthesizing tris(p-tolyl)thionium hexafluorophosphate according to claim 1, characterized in that, In step S1, the mass-to-volume ratio of the di(4-chlorophenyl) sulfoxide to the solvent is 1:(8~10) g / mL.
4. The method for synthesizing tris(p-tolyl)thionium hexafluorophosphate according to claim 1, characterized in that, In step S1, the molar ratio of bis(4-chlorophenyl) sulfoxide to p-tolyl magnesium bromide is 1:(4~6).
5. The method for synthesizing tris(p-tolyl)thionium hexafluorophosphate according to claim 1, characterized in that, In step S1, the molar ratio of bis(4-chlorophenyl) sulfoxide to trimethylchlorosilane is 1:(3~5).
6. The method for synthesizing tris(p-tolyl)thionium hexafluorophosphate according to claim 1, characterized in that, In step S1, the rate of adding trimethylchlorosilane is 0.5~0.8 mL / min.
7. The method for synthesizing tris(p-tolyl)thionium hexafluorophosphate according to claim 1, characterized in that, In step S2, the concentration of the potassium hexafluorophosphate aqueous solution is 61.4 g / L; the molar ratio of potassium hexafluorophosphate to di(4-chlorophenyl) sulfoxide in the potassium hexafluorophosphate aqueous solution is 2:
1.
8. The method for synthesizing tris(p-tolyl)thionium hexafluorophosphate according to claim 1, characterized in that, In step S2, the reaction temperature is 20 °C, the reaction time is 2 h, and the stirring rate is 800~1200 rpm.
9. The method for synthesizing tris(p-tolyl)thionium hexafluorophosphate according to claim 1, characterized in that, In step S2, the solvent used for recrystallization is a mixture of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane in the mixture is 1:3; and the recrystallization temperature is 20~35 ℃.