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N-(methyl sulphonyl)-p-methylphenyl sulphonylamine and preparation method thereof

A technology of toluenesulfonamide and methylsulfonyl, which is applied in the field of N-(methylsulfonyl)-p-toluenesulfonamide and its preparation, can solve the problem of limited popularization and application, poor technical effect, lack of High-gloss powder coating curing agent catalysts and other issues to achieve a good catalytic effect

Inactive Publication Date: 2015-10-28
ANSHAN RUNDE FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, although tetrakis (methoxymethyl) glycoluril (TMMGU) has been domestically produced, the high-gloss powder coating curing agent catalyst series products used with it still need to be imported
[0004] Due to the lack of high-gloss powder coating curing agent catalysts when the domestic tetra(methoxymethyl) glycoluril and its supporting series of products are used, the technical effect is not good, which limits its promotion and application in China

Method used

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  • N-(methyl sulphonyl)-p-methylphenyl sulphonylamine and preparation method thereof
  • N-(methyl sulphonyl)-p-methylphenyl sulphonylamine and preparation method thereof
  • N-(methyl sulphonyl)-p-methylphenyl sulphonylamine and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] In the reactor equipped with mechanical stirring, reflux condenser, nitrogen feed device and sampling port, add 400 milliliters of tetrahydrofuran, react raw materials 41 grams of toluenesulfonyl chloride, 20 grams of methylsulfonamide and 1 gram of trimethyl trimethyl Add benzyl ammonium chloride, stir to dissolve, pass nitrogen protection, heat up to 67 ° C, reflux reaction, add 32 grams of anhydrous potassium carbonate in batches, keep the temperature for 10 hours, until the reaction raw materials disappear, evaporate the organic solvent under reduced pressure, A white to pale yellow solid was obtained.

[0037] Dissolve the above solid in 200 ml of demineralized water, stir until it is completely dissolved, add 40 ml of 36% concentrated hydrochloric acid dropwise, after the addition is completed, adjust the pH value to less than 1, cool down to 20°C, and stir for 2.5 hours, white crystals precipitate out. Filtration to obtain a white solid was dried under reduced pr...

Embodiment 2

[0039] In a reactor equipped with mechanical stirring, reflux condensing tube, nitrogen feeding device and sampling port, add 400 ml of 1,4-dioxane, 41 g of toluenesulfonyl chloride, 20 g of methylsulfonamide Add 1 gram of tetrabutylammonium chloride, stir to dissolve, pass nitrogen protection, heat up to 106 ° C, reflux reaction, add 25 grams of anhydrous sodium carbonate in batches, keep warm for 6 hours, until the reaction raw materials disappear, evaporate under reduced pressure The organic solvent was removed to obtain a white to light yellow solid.

[0040] Dissolve the above solid in 200 ml of demineralized water and stir to dissolve completely, add 40 ml of 36% concentrated hydrochloric acid dropwise, after the addition is completed, adjust the pH value to less than 1, cool down to 20°C, and stir for 3 hours, white crystals precipitate out. Filtration to obtain a white solid was dried under reduced pressure to obtain 45 g of product with a yield of 86.5%.

Embodiment 3

[0042] In the reactor equipped with mechanical stirring, reflux condenser, nitrogen feed device and sampling port, add 420 milliliters of toluene, react raw materials 41 grams of toluenesulfonyl chloride, 20 grams of methylsulfonamide and 1 gram of benzyl tri Ethylammonium chloride was added, stirred to dissolve, protected by nitrogen, heated to 115°C, reflux reaction, added 25 grams of anhydrous sodium carbonate in batches, kept for 5 hours, until the reaction raw materials disappeared, and the organic solvent was evaporated under reduced pressure. A white to pale yellow solid was obtained.

[0043] Dissolve the above solid in 200 ml of demineralized water, stir until it is completely dissolved, add 40 ml of 36% concentrated hydrochloric acid dropwise, after the addition is completed, adjust the pH value to less than 1, cool down to 20°C, stir for 2 hours, white crystals precipitate , filtered to obtain a white solid, dried under reduced pressure to obtain 40 grams of product...

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Abstract

The invention relates to N-(methyl sulphonyl)-p-methylphenyl sulphonylamine shown in the formula (I) and a preparation method thereof. The preparation method includes the steps that p-toluenesulfonyl chloride, methyl sulfonamide and a phase transfer catalyst are dissolved in an organic solvent, the mixture is heated to 60 DEG C-120 DEG C, an acid-binding agent is added, the organic solvent is distilled out after complete reaction, a generated solid is dissolved in water, the pH value is adjusted to be smaller than 1 through hydrochloric acid, the temperature is decreased to 20 DEG C-24 DEG C, crystals are separated out, filtration and drying are performed, and then the N-(methyl sulphonyl)-p-methylphenyl sulphonylamine is obtained. According to the method, the raw materials are easy to obtain, operation is easy and convenient, productivity is high, and large-scale continuous production is easy; the N-(methyl sulphonyl)-p-methylphenyl sulphonylamine has a good catalytic effect on polyester-system products of TMMGU, is a brand-new high-gloss powder coating curing agent or catalyst and can used for preparing environment-friendly high-gloss high-performance paint films.

Description

technical field [0001] The invention relates to N-(methylsulfonyl)-p-toluenesulfonamide and a preparation method thereof, and is a brand-new high-gloss powder coating curing agent catalyst. Background technique [0002] At present, a new type of environmentally friendly, high-performance high-gloss powder coating curing agent widely used in the world, the name is: tetrakis (methoxymethyl) glycoluril (TMMGU). It is an ideal substitute for triglycidyl isocyanurate (TGIC), which is highly irritating and toxic to human skin and respiratory tract, and has been widely used in developed countries in the world. For a long time, it was only produced by Cytec Corporation of the United States, and its commercial name was Powderlink1174. Therefore, its promotion and application in China were greatly limited. Fortunately, at present, tetrakis (methoxymethyl) glycoluril (TMMGU) has been domestically produced. [0003] It is worth mentioning that tetrakis (methoxymethyl) glycoluril (TMMG...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/40C07C311/48B01J31/02
Inventor 柳问林叶维德韩兴海徐红玲李文龙张琪雯汪海燕庞小琳
Owner ANSHAN RUNDE FINE CHEM
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