A kind of synthesis method and synthesis device of benzenesulfonyl fluoride

Abstract

The invention belongs to the technical field of organic intermediate synthesis, and in particular to a kind of synthetic method and synthesis device of benzenesulfonyl fluoride.The synthetic method of benzenesulfonyl fluoride of the present invention, comprises the following steps: first hydrogen fluoride and sulfuryl chloride are added to a premixer, and successively pass through tubular reactor a, b, c, enter terminal reactor mixed reaction, control gas-liquid two-phase mixed reaction by terminal reactor, vertical condenser a, prepare sulfuryl fluoride chloride, then sulfuryl fluoride chloride, benzene, catalyst are mixed, enter sulfonation reactor reaction, control the progress of sulfonation reaction by sulfonation reactor, vertical filler b, obtain mixed reaction liquid, finally mixed reaction liquid is distilled, collect fraction, obtain benzenesulfonyl fluoride.The synthetic method of benzenesulfonyl fluoride provided by the present invention, reaction condition requirement is low, stable, easy to control, unit consumption is low, subsequent easy processing, prepared benzenesulfonyl fluoride yield is high, purity is high.The present invention also provides the synthesis device adopted by the synthetic method of benzenesulfonyl fluoride.

Description

Technical Field

[0001] The invention belongs to the technical field of organic intermediate synthesis, and particularly relates to a synthesis method and a synthesis device for benzenesulfonyl fluoride. Background Art

[0002] Benzenesulfonyl fluoride Benzenesulfonyl fluoride is a colorless liquid organic compound with a strong, pungent odor. It is commonly used as a chemical reagent, fine chemical, pharmaceutical intermediate, and material intermediate. Benzenesulfonyl fluoride can participate in fluorination reactions of organic compounds such as esters, amides, ethers, and alkenes, introducing fluorine atoms and altering the molecular structure.

[0003] The preparation method of benzenesulfonyl fluoride is mainly through the reaction of benzenesulfonyl chloride and hydrogen fluoride. For example, Example 2 of CN109734633A discloses that benzenesulfonyl chloride is added to polytetrafluoroethylene, aminosulfonic acid is used as a catalyst, the temperature is raised to 120°C, and anhydrous hydrogen fluoride gas is uniformly introduced. The reaction temperature is maintained at 120±5°C. Benzenesulfonyl fluoride is obtained by the reaction with a purity of 98.3% and a yield of 80.6%. However, the synthesis temperature of this reaction is too high and the amount of hydrogen fluoride used is large, resulting in a low yield.

[0004] For example, CN101585787A discloses a benzenesulfonyl fluoride compound, a preparation method and application thereof, wherein the precursor compound benzenesulfonyl chloride and metal fluoride are used as raw materials to carry out a fluorination reaction in acetonitrile for preparation. The fluorination reaction of the sulfonyl chloride substance is carried out by using a fluoride salt. Although the risk of fluorination is reduced, the reaction requires a large amount of organic matter as a solvent, and the process is complicated, making it difficult to achieve industrialization. Summary of the Invention

[0005] The technical problem to be solved by the present invention is to overcome the above-mentioned defects of the prior art and provide a method for synthesizing benzenesulfonyl fluoride, which has low reaction condition requirements, is stable, is easy to control, has low unit consumption, is easy to handle later, and produces benzenesulfonyl fluoride with high yield and high purity. The present invention also provides a synthesis device used in the method for synthesizing benzenesulfonyl fluoride.

[0006] The synthesis method of benzenesulfonyl fluoride of the present invention comprises the following steps: first, hydrogen fluoride and sulfuryl chloride are added to a premixer, and sequentially passed through a tubular reactor a, a tubular reactor b, and a tubular reactor c, and enter a terminal reactor for mixed reaction; the terminal reactor and a vertical condenser a at the upper end control a gas-liquid two-phase mixed reaction to obtain sulfuryl fluoride chloride; then, sulfuryl fluoride chloride, benzene, and a catalyst are mixed, and the mixture enters a sulfonation reactor for reaction; the sulfonation reaction is controlled by the sulfonation reactor and a vertical filler b at the upper end to obtain a mixed reaction liquid; and finally, the mixed reaction liquid is rectified, and fractions are collected to obtain benzenesulfonyl fluoride.

[0007] The catalyst is a mixture of aluminum chloride and 4-dimethylaminopyridine.

[0008] The molar ratio of hydrogen fluoride to sulfuryl chloride is 1:2.5-3.5.

[0009] The molar ratio of sulfuryl fluoride to benzene is 1:1.05-1.2.

[0010] The mass ratio of sulfuryl fluoride, aluminum chloride and 4-dimethylaminopyridine is 1:0.001-0.003:0.001-0.003.

[0011] The purity of sulfuryl chloride is ≥99%, the purity of benzene is ≥99.5%, and the purity of hydrogen fluoride is ≥99.5%.

[0012] The temperature of tubular reactor a was controlled at 50-60°C, the temperature of tubular reactor b was controlled at 65-75°C, and the temperature of tubular reactor c was controlled at 50-60°C.

[0013] Control the terminal reactor temperature at 35-45°C and the vertical condenser a temperature at -5-3°C.

[0014] Control the temperature of the sulfonation reactor at 40-55°C and the temperature of the vertical filler b at -5-3°C.

[0015] The flow rate of hydrogen fluoride added to the premixer is 0.3 kg / h-0.37 kg / h, and the flow rate of sulfuryl chloride added to the premixer is 5.15 kg / h-8.8 kg / h.

[0016] The synthesis device adopted in the benzenesulfonyl fluoride synthesis method includes a premixer, a tubular reactor a, a tubular reactor b, a tubular reactor c, a terminal reactor, a vertical condenser a, a sulfonation reactor, and a vertical filler b; the outlet of the premixer is connected to the inlet of the tubular reactor a, the outlet of the tubular reactor a is connected to the inlet of the tubular reactor b, the outlet of the tubular reactor b is connected to the inlet of the tubular reactor c, the outlet of the tubular reactor c is connected to the inlet of the terminal reactor, the top of the terminal reactor is provided with a vertical condenser a, the vertical condenser a is connected to the vertical filler a, the vertical filler a is connected to a sulfuryl fluoride chlorine condensation and collection device, the sulfuryl fluoride chlorine condensation and collection device is connected to a sulfuryl fluoride chlorine storage tank, the sulfuryl fluoride chlorine storage tank is connected to the sulfonation reactor, and the upper end of the sulfonation reactor is provided with a vertical filler b.

[0017] The vertical filler b is connected to the vertical condenser b, the vertical condenser b is connected to the hydrogen chloride treatment device, and the vertical filler a is connected to the hydrogen chloride treatment device.

[0018] The premixer is connected to a hydrogen fluoride tank and a sulfuryl chloride tank containing raw materials, and is used as a raw material supply.

[0019] Specifically, the synthesis method of benzenesulfonyl fluoride comprises the following steps:

[0020] (1) Adjust the temperatures of tubular reactor a, tubular reactor b, tubular reactor c, vertical condenser a, and terminal reactor to 50-60°C, 65-75°C, 50-60°C, -5-3°C, and 35-45°C, respectively, and open the pipeline between vertical filler a and the hydrogen chloride treatment device. Add hydrogen fluoride and sulfuryl chloride from the hydrogen fluoride tank and sulfuryl chloride tank to the premixer at a rate of 0.3kg / h~0.37kg / h and 5.15kg / h~8.8kg / h, respectively. After the addition is halfway through, turn on the circulation pump of the terminal reactor. Continue the reaction for 1-2 hours after the addition is completed. The hydrogen chloride gas generated during the reaction enters the hydrogen chloride treatment device. After the reaction is completed, cut the connecting pipeline of vertical filler a to the sulfuryl fluoride chlorine condensation collection device, and stop the heat exchange of vertical condenser a. Continue to maintain the temperature of the terminal reactor, separate the sulfuryl fluoride chlorine gas into the sulfuryl fluoride chlorine condensation collection device, and then introduce it into the sulfuryl fluoride chlorine storage tank.

[0021] (2) Add the catalyst to the sulfonation reactor, and adjust the temperature of the sulfonation reactor and the vertical filler b to 40-55°C and -5-3°C, respectively. Cut the connecting pipeline of the hydrogen chloride treatment device to the vertical condenser b, and then use a metering pump to pump the sulfuryl fluoride chlorine from the sulfuryl fluoride chlorine storage tank into the sulfonation reactor at a rate of 1.7-2.2 kg / h for a total of 2-3 hours. After the addition is completed, continue the reaction for 1-2 hours. The hydrogen chloride gas generated during the reaction enters the hydrogen chloride treatment device, and then after the reaction is completed, the reaction product is introduced into the distillation system for distillation treatment.

[0022] (3) Benzene and benzenesulfonyl fluoride in the mixed liquid to be distilled are distilled out in sequence, and finally the target product benzenesulfonyl fluoride is obtained in total. Its purity is tested and the yield is calculated according to HF.

[0023] According to the present invention, excessive sulfuryl chloride is continuously reacted in a multi-stage gradient temperature tubular reactor to generate a sulfuryl fluoride chlorine intermediate. Under the process conditions, the sulfuryl fluoride chlorine generation does not require a catalyst to promote the reaction. Moreover, under the conditions of different temperatures in the three-stage tubular reactor, the reaction process is more stable and efficient, fully ensuring the conversion rate and selectivity of the reaction. Then, the sulfuryl fluoride chlorine reacts with benzene. The exposed chlorine atoms of the sulfuryl fluoride have good reactivity with the benzene ring, and only a small amount of catalyst is needed to promote the reaction, thereby avoiding the problem of a large amount of solid waste by-products caused by a large amount of aluminum chloride promoting catalysis.

[0024] The process route of the reaction of the present invention is:

[0025] .

[0026] Compared with the prior art, the present invention has the following beneficial effects:

[0027] (1) The synthesis method of benzenesulfonyl fluoride of the present invention has stable process conditions, few side reactions, small amount of catalyst used, and simple solid waste treatment.

[0028] (2) The method for synthesizing benzenesulfonyl fluoride of the present invention has high yield, high purity and good quality.

[0029] (3) The synthesis device used in the synthesis method of benzenesulfonyl fluoride of the present invention is simple to operate, easy to control, and easy to realize industrialization. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 FIG. 1 is a diagram of the synthesis apparatus used in the synthesis method of benzenesulfonyl fluoride of the present invention.

[0031] In the figure: 1. Hydrogen fluoride tank; 2. Sulfuryl chloride tank; 3. Premixer; 4. Tubular reactor a; 5. Tubular reactor b; 6. Tubular reactor c; 7. Terminal reactor; 8. Vertical condenser a; 9. Vertical filler a; 10. Hydrogen chloride treatment device; 11. Sulfuryl fluoride chlorine condensation and collection device; 12. Sulfuryl fluoride chlorine storage tank; 13. Sulfonation reactor; 14. Vertical filler b; 15. Vertical condenser b. DETAILED DESCRIPTION

[0032] The present invention will be further described below with reference to specific embodiments.

[0033] The synthesis device used in the synthesis method of benzenesulfonyl fluoride is as follows: Figure 1 As shown, it includes a premixer 3, a tubular reactor a4, a tubular reactor b5, a tubular reactor c6, a terminal reactor 7, a vertical condenser a8, a sulfonation reactor 13, and a vertical stuffer b14; the outlet of the premixer 3 is connected to the inlet of the tubular reactor a4, the outlet of the tubular reactor a4 is connected to the inlet of the tubular reactor b5, the outlet of the tubular reactor b5 is connected to the inlet of the tubular reactor c6, the outlet of the tubular reactor c6 is connected to the inlet of the terminal reactor 7, the top of the terminal reactor 7 is provided with a vertical condenser a8, the vertical condenser a8 is connected to the vertical stuffer a9, the vertical stuffer a9 is connected to the sulfuryl fluoride chlorine condensation collection device 11, the sulfuryl fluoride chlorine condensation collection device 11 is connected to the sulfuryl fluoride chlorine storage tank 12, the sulfuryl fluoride chlorine storage tank 12 is connected to the sulfonation reactor 13, and the upper end of the sulfonation reactor 13 is provided with a vertical stuffer b14.

[0034] The vertical filler b14 is connected to the vertical condenser b15 , the vertical condenser b15 is connected to the hydrogen chloride treatment device 10 , and the vertical filler a9 is connected to the hydrogen chloride treatment device 10 .

[0035] The premixer 3 is connected to the hydrogen fluoride tank 1 and the sulfuryl chloride tank 2 containing raw materials, and serves as the raw material supply.

[0036] The raw materials used in the following examples have a mass content of 99.5% hydrogen fluoride, a mass content of 99.0% sulfuryl chloride, and a mass content of 99.5% benzene.

[0037] Example 1

[0038] The synthetic method of benzenesulfonyl fluoride comprises the following steps:

[0039] (1) Adjust the temperatures of tubular reactor a4, tubular reactor b5, tubular reactor c6, vertical condenser a8, and terminal reactor 7 to 50°C, 65°C, 50°C, -5°C, and 45°C, respectively, and open the pipeline between vertical filler a9 and hydrogen chloride treatment device 10. Add hydrogen fluoride and sulfuryl chloride from hydrogen fluoride tank 1 and sulfuryl chloride tank 2 to premixer 3 at a rate of 0.304 kg / h and 5.154 kg / h, respectively. After the addition is halfway through, turn on the circulation pump of terminal reactor 7. Finally, a total of 1.52 kg of hydrogen fluoride and 25.774 kg of sulfuryl chloride are added, respectively. After the addition is completed, continue the reaction for 2 hours. The hydrogen chloride gas generated during the reaction enters the hydrogen chloride treatment device 10. After the reaction is completed, cut the connecting pipeline of vertical filler a9 to the sulfuryl fluoride and chloride condensation collection device 11, and at the same time, shut down the circulation refrigeration of vertical condenser a8. The temperature of the terminal reactor 7 was maintained, and the sulfuryl fluoride chlorine gas was separated into the sulfuryl fluoride chlorine condensation collection device 11, and then introduced into the sulfuryl fluoride chlorine storage tank 12, and a total of 8.731 kg of sulfuryl fluoride chlorine was obtained (the yield was 95% based on HFmol and the purity was 98%).

[0040] (2) 5.921 kg of benzene, 26.193 g of aluminum chloride, and 26.193 g of 4-dimethylaminopyridine were added to the sulfonation reactor 13. The temperatures of the sulfonation reactor 13 and the vertical filler b14 were adjusted to 40°C and 3°C, respectively. The connecting pipeline of the hydrogen chloride treatment device 10 was cut to the vertical condenser b15. Then, the sulfuryl fluoride chlorine from the sulfuryl fluoride chlorine storage tank 12 was pumped into the sulfonation reactor 13 at a rate of 2.182 kg / h through a metering pump for a total of 4 hours. After the addition was completed, the reaction was continued for 2 hours. The hydrogen chloride gas generated during the reaction entered the hydrogen chloride treatment device 10. After the reaction was completed, the reaction product was introduced into the distillation system for distillation treatment.

[0041] (3) Benzene and benzenesulfonyl fluoride in the mixed liquid to be distilled were distilled out under normal pressure and -0.1 MPa conditions respectively, and finally a total of 10.971 kg of the target product benzenesulfonyl fluoride was obtained. The purity of the target product was 99%, and the yield was 95% based on sulfuryl fluoride.

[0042] Example 2

[0043] The synthetic method of benzenesulfonyl fluoride comprises the following steps:

[0044] (1) Adjust the temperatures of tubular reactor a4, tubular reactor b5, tubular reactor c6, vertical condenser a8, and terminal reactor 7 to 55°C, 70°C, 55°C, 0°C, and 40°C, respectively, and open the pipeline between vertical filler a9 and hydrogen chloride treatment device 10. Add hydrogen fluoride and sulfuryl chloride from hydrogen fluoride tank 1 and sulfuryl chloride tank 2 to premixer 3 at a rate of 0.37 kg / h and 8.801 kg / h, respectively. After the addition is halfway through, turn on the circulation pump of terminal reactor 7. Finally, a total of 1.483 kg of hydrogen fluoride and 35.205 kg of sulfuryl chloride are added, respectively. After the addition is completed, continue the reaction for 1.5 hours. The hydrogen chloride gas generated during the reaction enters the hydrogen chloride treatment device 10. After the reaction is completed, cut the connecting pipeline of vertical filler a9 to the sulfuryl fluoride and chloride condensation collection device 11, and at the same time shut down the circulation refrigeration of vertical condenser a8. The temperature of the terminal reactor 7 was maintained, and the sulfuryl fluoride chlorine gas was separated into the sulfuryl fluoride chlorine condensation collection device 11, and then introduced into the sulfuryl fluoride chlorine storage tank 12, and a total of 8.543 kg of sulfuryl fluoride chlorine was obtained (the yield was 96.2% based on HFmol and the purity was 98.4%).

[0045] (2) 6.128 kg of benzene, 17.086 g of aluminum chloride, and 17.086 g of 4-dimethylaminopyridine were added to the sulfonation reactor 13. The temperatures of the sulfonation reactor 13 and the vertical filler b14 were adjusted to 48°C and 0°C, respectively. The connecting pipeline of the hydrogen chloride treatment device 10 was cut to the vertical condenser b15. Then, the sulfuryl fluoride chlorine from the sulfuryl fluoride chlorine storage tank 12 was pumped into the sulfonation reactor 13 at a rate of 1.709 kg / h through a metering pump for a total of 5 hours. After the addition was completed, the reaction was continued for 1 hour. The hydrogen chloride gas generated during the reaction entered the hydrogen chloride treatment device 10. After the reaction was completed, the reaction product was introduced into the distillation system for distillation treatment.

[0046] (3) Benzene and benzenesulfonyl fluoride in the mixed liquid to be distilled were distilled out under normal pressure and -0.1 MPa conditions respectively, and finally a total of 10.998 kg of the target product benzenesulfonyl fluoride was obtained. The purity was detected to be 98.5%, and the yield was 95.3% based on sulfuryl fluoride.

[0047] Example 3

[0048] The synthetic method of benzenesulfonyl fluoride comprises the following steps:

[0049] (1) Adjust the temperatures of tubular reactor a4, tubular reactor b5, tubular reactor c6, vertical condenser a8, and terminal reactor 7 to 60°C, 75°C, 60°C, 3°C, and 35°C, respectively, and open the pipeline between vertical filler a9 and hydrogen chloride treatment device 10. Add hydrogen fluoride and sulfuryl chloride from hydrogen fluoride tank 1 and sulfuryl chloride tank 2 to premixer 3 at a rate of 0.332 kg / h and 5.633 kg / h, respectively. After the addition is halfway through, turn on the circulation pump of terminal reactor 7. Finally, a total of 1.495 kg of hydrogen fluoride and 25.349 kg of sulfuryl chloride are added, respectively. After the addition is completed, continue the reaction for 1 hour. The hydrogen chloride gas generated during the reaction enters the hydrogen chloride treatment device 10. After the reaction is completed, cut the connecting pipeline of vertical filler a9 to the sulfuryl fluoride and chloride condensation collection device 11, and at the same time shut down the circulation refrigeration of vertical condenser a8. The temperature of the terminal reactor 7 was maintained, and the sulfuryl fluoride chlorine gas was separated into the sulfuryl fluoride chlorine condensation collection device 11, and then introduced into the sulfuryl fluoride chlorine storage tank 12, and a total of 8.777 kg of sulfuryl fluoride chlorine was obtained (the yield was 97% based on HFmol and the purity was 97.4%).

[0050] (2) 6.796 kg of benzene, 8.777 g of aluminum chloride, and 8.777 g of 4-dimethylaminopyridine were added to the sulfonation reactor 13. The temperatures of the sulfonation reactor 13 and the vertical filler b14 were adjusted to 55°C and -5°C, respectively. The connecting pipeline of the hydrogen chloride treatment device 10 was cut to the vertical condenser b15. Then, the sulfuryl fluoride chlorine in the sulfuryl fluoride chlorine storage tank 12 was pumped into the sulfonation reactor 13 at a rate of 1.755 kg / h through a metering pump for a total of 5 hours. After the addition was completed, the reaction was continued for 1.5 hours. The hydrogen chloride gas generated during the reaction entered the hydrogen chloride treatment device 10. After the reaction was completed, the reaction product was introduced into the distillation system for distillation treatment.

[0051] (3) Benzene and benzenesulfonyl fluoride in the mixed liquid to be distilled were distilled out under normal pressure and -0.1 MPa conditions respectively, and finally a total of 10.994 kg of the target product benzenesulfonyl fluoride was obtained. The purity of the target product was 99.3%, and the yield was 94.8% based on sulfuryl fluoride.

[0052] Example 4

[0053] The synthetic method of benzenesulfonyl fluoride comprises the following steps:

[0054] (1) Adjust the temperatures of tubular reactor a4, tubular reactor b5, tubular reactor c6, vertical condenser a8, and terminal reactor 7 to 57°C, 72°C, 57°C, 0°C, and 41°C, respectively, and open the pipeline between vertical filler a9 and hydrogen chloride treatment device 10. Add hydrogen fluoride and sulfuryl chloride from hydrogen fluoride tank 1 and sulfuryl chloride tank 2 to premixer 3 at a rate of 0.333 kg / h and 6.791 kg / h, respectively. After the addition is halfway through, turn on the circulation pump of terminal reactor 7. Finally, a total of 1.502 kg of hydrogen fluoride and 30.562 kg of sulfuryl chloride are added, respectively. After the addition is completed, continue the reaction for 1.5 hours. The hydrogen chloride gas generated during the reaction enters the hydrogen chloride treatment device 10. After the reaction is completed, cut the connecting pipeline of vertical filler a9 to the sulfuryl fluoride and chloride condensation collection device 11, and at the same time shut down the circulation refrigeration of vertical condenser a8. The temperature of the terminal reactor 7 was maintained, and the sulfuryl fluoride chlorine gas was separated into the sulfuryl fluoride chlorine condensation collection device 11, and then introduced into the sulfuryl fluoride chlorine storage tank 12, and a total of 8.791 kg of sulfuryl fluoride chlorine was obtained (the yield was 97.3% based on HFmol and the purity was 98%).

[0055] (2) 5.993 kg of benzene, 17.582 g of aluminum chloride, and 13.186 g of 4-dimethylaminopyridine were added to the sulfonation reactor 13. The temperatures of the sulfonation reactor 13 and the vertical filler b14 were adjusted to 47°C and 0°C, respectively. The connecting pipeline of the hydrogen chloride treatment device 10 was cut to the vertical condenser b15. Then, the sulfuryl fluoride chlorine from the sulfuryl fluoride chlorine storage tank 12 was pumped into the sulfonation reactor 13 at a rate of 2.182 kg / h through a metering pump for a total of 4.5 hours. After the addition was completed, the reaction was continued for 1.5 hours. The hydrogen chloride gas generated during the reaction entered the hydrogen chloride treatment device 10. After the reaction was completed, the reaction product was introduced into the distillation system for distillation treatment.

[0056] (3) Benzene and benzenesulfonyl fluoride in the mixed liquid to be distilled were distilled out under normal pressure and -0.1 MPa conditions respectively, and finally 11.27 kg of the target product benzenesulfonyl fluoride was obtained. The purity was detected to be 99.5%, and the yield was 96.3% based on sulfuryl fluoride.

[0057] Comparative Example 1

[0058] This comparative example was the same as Example 1 except that the tubular reactor in step (1) was removed, and all other preparation conditions were the same. A total of 4.21 kg of the target product, benzenesulfonyl fluoride, was obtained, with a yield of 25.61% based on the molar amount of HF. The purity was determined to be 70%.

[0059] Comparative Example 2

[0060] This comparative example was the same as Example 1, except that the temperatures of the three-stage tubular reactor in step (1) were set to 20°C, 30°C, and 20°C, respectively, and all other preparation conditions were the same. A total of 5.35 kg of the target product, benzenesulfonyl fluoride, was obtained, with a yield of 33.47% based on the molar amount of HF. The purity was determined to be 72%.

[0061] Comparative Example 3

[0062] This comparative example was the same as Example 1, except that the amount of benzene added in step (2) was adjusted to twice the molar amount of sulfuryl fluoride chloride. Other preparation conditions remained the same. A total of 4.113 kg of the target product, benzenesulfonyl fluoride, was obtained, with a yield of 17.51% based on the molar amount of HF. The purity was determined to be 49%.

[0063] Comparative Example 4

[0064] This comparative example was the same as Example 1, except that the aluminum chloride and 4-dimethylaminopyridine catalyst in step (2) were removed, and all other preparation conditions were the same. A total of 2.15 kg of the target product, benzenesulfonyl fluoride, was obtained, with a yield of 11.21% based on the molar amount of HF. The purity was determined to be 60%.

[0065] Comparative Example 5

[0066] This comparative example was the same as Example 1 except that the 4-dimethylaminopyridine catalyst in step (2) was removed, and all other preparation conditions were the same. A total of 5.4 kg of the target product, benzenesulfonyl fluoride, was obtained, with a yield of 31.91% based on the molar amount of HF. The purity was determined to be 68%.

[0067] Comparative Example 6

[0068] This comparative example was the same as Example 1, except that the temperature of the sulfonation reaction vessel in step (2) was lowered to 20°C, and all other preparation conditions remained the same. A total of 4.113 kg of the target product, benzenesulfonyl fluoride, was obtained, with a yield of 17.51% based on the molar amount of HF. The purity was determined to be 49%.

Claims

1. A method for synthesizing benzenesulfonyl fluoride, characterized in that: The method comprises the following steps: firstly, adding hydrogen fluoride and sulfuryl chloride into a premixer, and sequentially passing through a tubular reactor a, a tubular reactor b, and a tubular reactor c, and entering a terminal reactor for mixed reaction; controlling a gas-liquid two-phase mixed reaction through the terminal reactor and a vertical condenser a at the upper end to obtain sulfuryl fluoride chloride; then mixing sulfuryl fluoride chloride, benzene, and a catalyst, and entering a sulfonation reactor for reaction; controlling the sulfonation reaction through the sulfonation reactor and a vertical filler b at the upper end to obtain a mixed reaction liquid; and finally, rectifying the mixed reaction liquid, collecting fractions, and obtaining benzenesulfonyl fluoride.

2. The synthetic method of benzenesulfonyl fluoride according to claim 1, wherein: The catalysts are aluminum chloride and 4-dimethylaminopyridine.

3. The synthetic method of benzenesulfonyl fluoride according to claim 1, wherein: The molar ratio of hydrogen fluoride to sulfuryl chloride is 1:2.5-3.

5.

4. The synthetic method of benzenesulfonyl fluoride according to claim 2, wherein: The molar ratio of sulfuryl fluoride to benzene is 1:1.05-1.2, and the mass ratio of sulfuryl fluoride to aluminum chloride to 4-dimethylaminopyridine is 1:0.001-0.003:0.001-0.

003.

5. The method for synthesizing benzenesulfonyl fluoride according to claim 1, wherein: The temperature of tubular reactor a was controlled at 50-60°C, the temperature of tubular reactor b was controlled at 65-75°C, and the temperature of tubular reactor c was controlled at 50-60°C.

6. The method for synthesizing benzenesulfonyl fluoride according to claim 5, wherein: Control the terminal reactor temperature at 35-45°C and the vertical condenser a temperature at -5-3°C.

7. The method for synthesizing benzenesulfonyl fluoride according to claim 6, wherein: Control the temperature of the sulfonation reactor at 40-55°C and the temperature of the vertical filler b at -5-3°C.

8. The method for synthesizing benzenesulfonyl fluoride according to claim 1, wherein: The flow rate of hydrogen fluoride added to the premixer is 0.3 kg / h-0.37 kg / h, and the flow rate of sulfuryl chloride added to the premixer is 5.15 kg / h-8.8 kg / h.

9. A synthesis device used in the method for synthesizing benzenesulfonyl fluoride according to any one of claims 1 to 8, characterized in that: The invention comprises a premixer (3), a tubular reactor a (4), a tubular reactor b (5), a tubular reactor c (6), a terminal reactor (7), a vertical condenser a (8), a sulfonation reactor (13), and a vertical filler b (14); the outlet of the premixer (3) is connected to the inlet of the tubular reactor a (4), the outlet of the tubular reactor a (4) is connected to the inlet of the tubular reactor b (5), the outlet of the tubular reactor b (5) is connected to the inlet of the tubular reactor c (6), and the tubular reactor c ( The outlet of the reactor (6) is connected to the inlet of the terminal reactor (7), the top of the terminal reactor (7) is provided with a vertical condenser a (8), the vertical condenser a (8) is connected to the vertical filler a (9), the vertical filler a (9) is connected to the sulfuryl fluoride chlorine condensation collection device (11), the sulfuryl fluoride chlorine condensation collection device (11) is connected to the sulfuryl fluoride chlorine storage tank (12), the sulfuryl fluoride chlorine storage tank (12) is connected to the sulfonation reactor (13), and the upper end of the sulfonation reactor (13) is provided with a vertical filler b (14).

10. The synthesis device used in the synthesis method of benzenesulfonyl fluoride according to claim 9, characterized in that: The vertical filler b (14) is connected to the vertical condenser b (15), the vertical condenser b (15) is connected to the hydrogen chloride treatment device (10), and the vertical filler a (9) is connected to the hydrogen chloride treatment device (10).

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