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Method and system for synthesizing p-acetaminobenzenesulfonyl chloride with sulfur trioxide as sulfonating agent

A technology of acetaminobenzenesulfonyl chloride and sulfur trioxide, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of additive influence, high processing cost, large amount of chlorosulfonic acid, etc., and achieve saving Disposal cost, environmental protection effect

Active Publication Date: 2018-12-04
吴赣药业(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Foreign production mainly adopts cryogenic drying technology equipment and spray granulation drying to make finished products, but additives have an impact on the reaction
The development trend is that the use of cryogenic drying is beneficial to the stability of the obtained product, but the investment is relatively large
In addition, the current synthesis method usually uses chlorosulfonic acid as a sulfonating agent, adding acetanilide to chlorosulfonic acid in batches at 40-60°C, reacting for 2-4 hours, diluting with ice water, and filtering to obtain the product. In this process, chlorine The amount of sulfonic acid is large, the waste acid produced is large, and the treatment cost is high

Method used

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  • Method and system for synthesizing p-acetaminobenzenesulfonyl chloride with sulfur trioxide as sulfonating agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] This embodiment provides a system for the synthesis of acetaminobenzenesulfonyl chloride with sulfur trioxide as a sulfonating agent, such as figure 1 As shown, it mainly includes a stirring batching tank 1, a pump 2, a storage tank 3 and a membrane reactor 6, etc.

[0019] Among them, the stirring batching tank 1 is used to stir and mix the reaction materials; the storage tank 3 is connected to the bottom of the stirring batching tank 1 through a pipeline, and a pump 2 is installed on the pipeline between them, and the stirring batching tank can be mixed by using the pump 2 The material in tank 1 is pumped into storage tank 3. The membrane reactor 6 is also communicated with the storage tank 3 through a pipeline, and another pump 2 is installed on the pipeline between them, and the reaction material stored in the storage tank 3 can be introduced into the membrane reactor 6 by the pump 2 react in. Sulfur trioxide gas storage tank 14 is in communication with membrane r...

Embodiment 2

[0022] The present embodiment provides a method for the synthesis of acetaminobenzenesulfonyl chloride with sulfur trioxide as a sulfonating agent, which comprises the following steps:

[0023] (a) Add 13.5kg of acetanilide and 30kg of thionyl chloride to the reactor in sequence, and stir to raise the temperature to 40°C;

[0024] (b) Slowly feed sulfur trioxide gas into the reactor (the flow rate of ventilation is 2.5L / min), and react at 40°C for 15 hours (the tail gas is absorbed by 1mol / L sodium carbonate solution); when the end of the reaction is approaching, every Sampling and analysis for 15 minutes (use HPLC for analysis), until the conversion of acetanilide is complete, stop feeding sulfur trioxide gas;

[0025] (c) Raise the temperature in the reactor to 70°C, recover the thionyl chloride under reduced pressure (the recovery quality is 17.5kg), and cool to obtain the crude p-acetaminobenzenesulfonyl chloride (purity: 98%, yield: 97%).

Embodiment 3

[0027] The present embodiment provides a method for the synthesis of acetaminobenzenesulfonyl chloride with sulfur trioxide as a sulfonating agent, which comprises the following steps:

[0028] (a) Add 13.5kg of acetanilide and 60kg of thionyl chloride to the reactor in sequence, and stir to raise the temperature to 70°C;

[0029] (b) Slowly feed sulfur trioxide gas into the reactor (the flow rate of ventilation is 13.0L / min), and react at 70°C for 3 hours (the tail gas is absorbed by 1mol / L sodium carbonate solution); when the end of the reaction is approaching, every Sampling and analysis for 5 minutes (use HPLC for analysis), until the conversion of acetanilide is complete, stop feeding sulfur trioxide gas;

[0030] (c) Raise the temperature in the reactor to 80°C, recover the thionyl chloride under reduced pressure (recovered mass is 17.1kg), and cool to obtain the crude p-acetaminobenzenesulfonyl chloride (purity: 96%, yield: 98%).

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Abstract

The invention relates to a method and a system for synthesizing p-acetamidobenzene sulfonyl chloride by taking sulfur trioxide as a sulfonating agent. The method comprises the following steps: (a) sequentially adding acetanilide and thionyl chloride into a reaction kettle, stirring and raising the temperature to 40-70 DEG C; (b) introducing sulfur trioxide gas into the reaction kettle, reacting for 3-15 hours at a temperature of 40-70 DEG C to enable the acetanilide to be completely converted and stopping introducing the sulfur trioxide gas; (c) raising the temperature in the reaction kettle to 65-80 DEG C, reducing the pressure, recovering the thionyl chloride and cooling. As the sulfur trioxide is adopted as the sulfonating agent to synthesize the p-acetamidobenzene sulfonyl chloride, the quality of the p-acetamidobenzene sulfonyl chloride is ensured, the generation of wastewater and waste acids is avoided, the treatment cost is saved, and the environmental protection is facilitated.

Description

technical field [0001] The invention belongs to the field of preparation of chemical intermediates, and in particular relates to a method and a system for synthesizing p-acetamidobenzenesulfonyl chloride by using sulfur trioxide as a sulfonating agent. Background technique [0002] Acetaminobenzenesulfonyl chloride is a pharmaceutical intermediate and the main raw material for the preparation of sulfamethoxazole and sulfathiazole and other sulfonamide drugs. At present, the domestic use is mainly for self-use, and the wet product is prepared and used immediately, otherwise it will happen. Decomposition, deterioration, and the period to achieve stable quality is only three days at most. As a real commodity, it is still blank in the market. Overseas production mainly adopts cryogenic drying technology equipment and spray granulation drying to make finished products, but additives have an impact on the reaction. The development trend is that the use of cryogenic drying is bene...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/88C07C303/06C07C303/44
CPCC07C303/06C07C303/44C07C309/88
Inventor 计建明钱炜雯朱凤林
Owner 吴赣药业(苏州)有限公司
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