A kind of preparation method of m-methanesulfonamidoaniline

A technology for methanesulfonamide and aniline, which is applied in the field of preparation of m-methanesulfonamidoaniline, can solve the problems of low product yield and content, incomplete acid binding, calcium chloride waste water, etc., and achieves improved yield and content , The effect of reducing the consumption of acid binding agent and reducing the pollution of three wastes

Active Publication Date: 2021-01-08
LEPING SAFELY PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The classic synthetic method of m-methanesulfonamidoaniline is to take m-phenylenediamine and methanesulfonyl chloride as raw materials, and in the presence of acid-binding agent, it is synthesized through aqueous phase reaction. Documents generally use calcium carbonate as acid-binding agent, but calcium carbonate The water solubility is small, and the ordinary calcium carbonate particles are relatively coarse and the surface area is small. The reaction product m-methanesulfonamidoaniline is insoluble in water, and it will wrap calcium carbonate, resulting in incomplete acid binding. It needs to add more acid to destroy the excess calcium carbonate, so there are disadvantages such as uneven reaction, low product yield and content, and cumbersome post-treatment.
In addition, the process also produces a large amount of calcium chloride wastewater

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of m-methylsulfonamidoaniline

[0030] In a 2000mL four-necked flask equipped with mechanical stirring and a thermometer, add 1200 mL of water, 108.0g (1.0mol) of m-phenylenediamine, and 0.4g of benzyltriethylammonium chloride. And the calcium chloride waste water after filtering m-methanesulfonamidoaniline of last batch is raw material, add 0.4% polyethylene glycol-400 preparation, the superfine calcium carbonate acid-binding agent 51.2g (0.512 mol), stirred and cooled, and kept at -2~3°C and added dropwise 118.0g (1.03mol) of methanesulfonyl chloride, dropped over 2.5h, kept at 0~5°C for 5.0h, and raised the temperature to 15~20°C for 5.0h. Cool to below 10°C, filter, and wash with ice water to obtain 181.9 g of the product m-methylsulfonamidoaniline, with a yield of 97.8%, a content of 98.7%, an unreacted raw material m-phenylenediamine content of 0.37%, and bis-methylsulfonyl The content of 1,3-bis-methanesulfonamidobenzene in the produc...

Embodiment 2

[0031] Embodiment 2: the synthesis of m-methylsulfonamidoaniline

[0032] In a 2000mL four-necked flask equipped with a mechanical stirrer and a thermometer, add 1000 mL of water, 108.0g (1.0mol) of m-phenylenediamine, and 1.2g of dodecyldimethylbenzyl ammonium chloride. Under good stirring, add 43.8g of ultra-fine magnesium carbonate acid-binding agent with an average particle size of less than 1 micron prepared by using sodium carbonate solution and the magnesium chloride wastewater after filtering m-methanesulfonamidoaniline as raw materials, adding 0.25% polyethylene glycol-800 (0.521mol), stirred and cooled, and added dropwise 123.7g (1.08mol) of methanesulfonyl chloride at 0~5°C, dropped over 4.5h, kept at 5~10°C for 3.0h, and heated to 18~23°C for 4.0h. Cooled to below 12°C, filtered, and washed with ice water to obtain 182.7g of the product m-methylsulfonamidoaniline, with a yield of 98.2%, a content of 98.4%, and an unreacted raw material m-phenylenediamine content of...

Embodiment 3

[0033] Embodiment 3: the synthesis of m-methylsulfonamidoaniline

[0034]In a 2000mL four-necked flask equipped with mechanical stirring and a thermometer, add 850mL of water, 108.0g (1.0mol) of m-phenylenediamine, and 1.9g of sodium lauryl sulfate. Under good stirring, add sodium carbonate solution and the previous batch The mixed wastewater of calcium chloride and magnesium chloride after filtering m-methanesulfonamidoaniline (the molar ratio of calcium chloride to magnesium chloride is 9:11) is used as raw material, prepared by adding 0.15% polyethylene glycol-1000, and the average particle size is less than 1 micron Superfine calcium carbonate and superfine magnesium carbonate acid-binding agent 47.4g (the molar ratio of calcium carbonate and magnesium carbonate is 9:11, 0.520mol in total), stirring and cooling, keep -8~-3℃, dropwise add 120.2g of methanesulfonyl chloride (1.05mol), dripping over 5.0h, keep at -2~3°C for 5.0h, heat up to 25~30°C for 3.5h. Cool to below 10...

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Abstract

The invention discloses a preparation method of m-methanesulfonamide. The preparation method is characterized in that methylsufonyl chloride is dropwise added into a suspension of an optionally proportioned mixture acid-binding agent of m-phenylenediamine, a surface active agent, superfine calcium carbonate or magnesium carbonate or superfine calcium carbonate and magnesium carbonate with the meangrain size of 1 micron or below and water, low-temperature adding is performed, heat insulation is performed after adding, heating and heat insulation are performed, and cooling, filtration and the like are performed to obtain the m-methanesulfonamide. Calcium chloride wastewater or magnesium chloride wastewater or mixed wastewater of calcium chloride and magnesium chloride produced by the process reacts with sodium carbonate in the presence of polyethylene glycol to obtain a superfine acid-binding agent required by the process, and resources are fully utilized. By adding and jointly using the superfine acid-binding agent and the surface active agent, the product yield and quality are obviously improved. Compared with a traditional process, the method has the advantages of being quick, uniform and complete in reaction, producing by-products, simplifying operation, improving the yield and quality, decreasing the three wastes and the like and has good industrial prospect.

Description

technical field [0001] The invention relates to a preparation method of m-methylsulfonamidoaniline, which belongs to the field of organic synthesis. Background technique [0002] m-Methanesulfonamidoaniline is an intermediate of dyes such as disperse red 343, and is also an important intermediate of medicine, pesticides, materials, etc. [0003] The classic synthetic method of m-methanesulfonamidoaniline is to take m-phenylenediamine and methanesulfonyl chloride as raw materials, and is synthesized through aqueous phase reaction in the presence of an acid-binding agent. The literature generally uses calcium carbonate as an acid-binding agent, but calcium carbonate The water solubility is small, and the ordinary calcium carbonate particles are relatively thick and the surface area is small. The reaction product m-methanesulfonamidoaniline is insoluble in water, and it will wrap calcium carbonate, resulting in incomplete acid binding. It is necessary to add more acid to destr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/38C07C311/08
CPCC07C303/38C07C311/08
Inventor 陈盛陶安妮王一键潘劲松邱永勇牟忠岳毛春飞郑土才
Owner LEPING SAFELY PHARMA
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