Preparation method of m-methanesulfonamide

A technology of 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 achieve improved yield and content , reduce the consumption of acid-binding agent and reduce the pollution of three wastes

Active Publication Date: 2018-12-28
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 s

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0029] Example 1: Synthesis of m-Methanesulfonamidoaniline

[0030] In a 2000 mL four-necked flask with mechanical stirring and thermometer, add 1200 mL of water, 108.0 g (1.0 mol) of m-phenylenediamine, and 0.4 g of benzyl triethylammonium chloride. Under good stirring, add sodium carbonate solution And the last batch of calcium chloride wastewater after filtering m-methylsulfonamidoaniline as raw material, adding 0.4% polyethylene glycol-400, the average particle size of ultrafine calcium carbonate below 1 micron 51.2g (0.512 mol), stir and cool, add 118.0g (1.03mol) of methanesulfonyl chloride dropwise at -2~3℃, drop it in 2.5h, keep it at 0~5℃ for 5.0h, heat up to 15~20℃ for 5.0h. Cooled to below 10°C, filtered and washed with ice water to obtain 181.9g of product m-methylsulfonamidoaniline, yield 97.8%, content 98.7%, unreacted raw material m-phenylenediamine content 0.37%, bis-methylsulfonylation side The 1,3-bis-methanesulfonamidobenzene content of the product is 0.28%.

Example Embodiment

[0031] Example 2: Synthesis of m-Methanesulfonamidoaniline

[0032] In a 2000 mL four-necked flask with mechanical stirring and thermometer, add 1000 mL of water, 108.0 g (1.0 mol) of m-phenylenediamine, and 1.2 g of dodecyl dimethyl benzyl ammonium chloride. Under good stirring, add Using sodium carbonate solution and the last batch of magnesium chloride wastewater after filtering m-methylsulfonamidoaniline as raw materials, adding 0.25% polyethylene glycol-800, 43.8g of ultrafine magnesium carbonate acid binding agent with an average particle size of less than 1 micron (0.521mol), stir and cool, keep 0~5℃ and add 123.7g (1.08mol) of methanesulfonyl chloride dropwise, after 4.5h dripping, keep 5~10℃ for 3.0h, heat up to 18~23℃ for 4.0h. Cooled to below 12°C, filtered and washed with ice water to obtain 182.7g of product m-methylsulfonamidoaniline, yield 98.2%, content 98.4%, unreacted raw material m-phenylenediamine content 0.21%, bis-methylsulfonylation The 1,3-bis-methanesulf...

Example Embodiment

[0033] Example 3: Synthesis of m-Methanesulfonamidoaniline

[0034] In a 2000mL four-necked flask with mechanical stirring and thermometer, add 850mL of water, 108.0g (1.0mol) of m-phenylenediamine and 1.9g of sodium lauryl sulfate. Under good stirring, add the sodium carbonate solution and the previous batch Calcium chloride and magnesium chloride mixed wastewater after filtering m-methylsulfonamidoaniline (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, with an average particle size of less than 1 micron 47.4g of superfine calcium carbonate and superfine magnesium carbonate acid binding agent (the molar ratio of calcium carbonate to magnesium carbonate is 9:11, total 0.520mol), stir and cool, keep at -8~-3℃, add 120.2g of methanesulfonyl chloride dropwise (1.05mol), after 5.0h dripping, keep at -2~3℃ for 5.0h, heat up to 25~30℃ for 3.5h. Cooled to below 10°C, filtered and washed with...

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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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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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