Method for preparing tribenuron-methyl

A technology for trisulfuron-methyl and oxycarbonylbenzenesulfonamide is applied in the field of preparation of trisulfuron-methyl, which can solve the problems of high cost, low production safety and high product cost, and achieves small amount of three wastes, high production safety and simple operation. Effect

Inactive Publication Date: 2012-10-10
HEFEI JIUYI AGRI DEV
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Problems solved by technology

The raw material oxalyl chloride is expensive, resulting in higher product costs; phosgene is highly toxic, which has adverse effects on raw material storage, transportation and production environments; the three-phosgene method needs to be reacted in a closed system and at a higher temperature, and requires When using xylene and catalyst, it is necessary to seal the reaction for 24h when synt

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  • Method for preparing tribenuron-methyl
  • Method for preparing tribenuron-methyl
  • Method for preparing tribenuron-methyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 5000-liter reactor, add 21.4 kilograms of potassium carbonate, water, 43.2 liters of acetone, and 13.6 kilograms of o-methoxycarbonylbenzenesulfonamide, stir to form a paste and lower the temperature to 5°C, add 8.463 kilograms of ethyl chloroformate dropwise, and heat up to 20°C, react for more than 3 hours, filter and dry to obtain ethyl o-methoxycarbonylbenzenesulfonamide formate as a solid;

[0023] 8.736 kg of 2-methylamino-4-methoxy-6-methyl-s-triazine was dissolved in toluene to obtain 2-methylamino-4-methoxy-6-methyl-s-triazine solution;

[0024] Dissolve the solid ethyl o-methoxycarbonylbenzenesulfonamide formate obtained above in toluene, add 2-methylamino-4-methoxy-6-methyl-s-triazine solution dropwise at 50°C, and control the dropping time for 1h , kept at this temperature for 8h, then distilled, filtered, and dried to obtain 18.8 kg of the original drug of tribenuron-methyl, the calculated yield was 79.32%, and the determined content of tribenuron-meth...

Embodiment 2

[0026] In a 5000-liter reactor, add 21.4 kilograms of pyridine, water, 43.2 liters of acetone, and 13.6 kilograms of o-methoxycarbonylbenzenesulfonamide, stir to form a paste and lower the temperature to 3°C, add 9.114 kilograms of ethyl chloroformate dropwise, and heat up to 18 °C, react for more than 3 hours, filter and dry to obtain ethyl o-methoxycarbonylbenzenesulfonamide formate as a solid;

[0027] 8.82 kg of 2-methylamino-4-methoxy-6-methyl-s-triazine was dissolved in toluene to obtain 2-methylamino-4-methoxy-6-methyl-s-triazine solution;

[0028] Dissolve the solid ethyl o-methoxycarbonylbenzenesulfonamide formate obtained above in toluene, add 2-methylamino-4-methoxy-6-methyl-s-triazine solution dropwise at 50°C, and control the dropping time for 1h. Insulate at this temperature for 8 hours, then distill, filter, and dry to obtain 19.4 kg of the original drug of tribenuron-methyl, the calculated yield is 81.86%, and the content of tribenuron-methyl is determined to b...

Embodiment 3

[0030] In a 5,000-liter reactor, add 16.4 kilograms of sodium hydroxide, water, 43.2 liters of ethanol, and 13.6 kilograms of o-methoxycarbonylbenzenesulfonamide, stir to form a paste and lower the temperature to 2°C, add 8.463 kilograms of ethyl chloroformate dropwise, and heat up To 13°C, react for more than 3 hours, filter and dry to obtain ethyl o-methoxycarbonylbenzenesulfonamide formate as a solid;

[0031] 8.736 kg of 2-methylamino-4-methoxy-6-methyl-s-triazine was dissolved in toluene to obtain 2-methylamino-4-methoxy-6-methyl-s-triazine solution;

[0032] Dissolve the solid ethyl o-methoxycarbonylbenzenesulfonamide formate obtained above in toluene, add 2-methylamino-4-methoxy-6-methyl-s-triazine solution dropwise at 50°C, and control the dropping time for 1h. Keep it warm at this temperature for 8 hours, then distill, filter, and dry to obtain 18.97 kg of the original drug of tribenuron-methyl, the calculated yield is 79.97%, and the determined content of tribenuron-...

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Abstract

The invention discloses a method for preparing tribenuron-methyl, which comprises the following steps: ortho carbomethoxyl group benzene sulfonamide and ethyl chloroformate are reacted in a solvent, filtered and dried to obtain an ortho carbomethoxyl group benzene sulfonamide ethyl formate solid, the ortho carbomethoxyl group benzene sulfonamide ethyl formate solid is dissolved in the solvent, a 2-methylamino-4-methoxy-6-methyl-s-triazine solution is added drop by drop, stirred and heated, and reacted to obtain the tribenuron-methyl, wherein the purity is greater than or equal to 95%. According to the invention, ethyl chloroformate is used as an amide agent, the reaction temperature can be controlled by ice bath, and the speed for adding ethyl chloroformate drop by drop can be controlled, thereby the ethyl chloroformate is reacted with ortho carbomethoxyl group benzene sulfonamide in the solvent to obtain the ortho carbomethoxyl group benzene sulfonamide ethyl formate, and then reacted with s-triazine to obtain tribenuron-methyl. The present invention adopts ethyl chloroformate as a raw material, compared with phosgene, triphosgene and oxalyl chloride, and the method for preparing the tribenuron-methyl has the advantages of simple operation, high production security, low cost and less generation amount of three wastes.

Description

technical field [0001] The invention relates to the technical field of herbicide pesticides, in particular to a method for preparing tribenuron-methyl. Background technique [0002] Tribenuronmethyl belongs to the selective systemic absorption conduction type sulfonylurea herbicide, its English name is Tribenuronmethyl, and its chemical name is 2-[4-methoxy-6-1,3,5-triazin-2-yl (methyl ) carbamidosulfonyl] benzoic acid, molecular formula C 15 h 17 N 5 o 6 S, the structural formula is as shown in formula (I). [0003] [0004] At present, its synthetic method generally adopts the isocyanate route, and o-methoxycarbonylbenzenesulfonamide and oxalyl chloride react to obtain 2-formic acid methyl ester-3-benzenesulfonyl isocyanate; or by o-methoxycarbonylbenzenesulfonamide and phosgene or triphosgene ( Solid phosgene) reaction to obtain 2-methyl formate-3-benzenesulfonyl isocyanate. The raw material oxalyl chloride is expensive, resulting in higher product costs; phosgen...

Claims

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Application Information

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IPC IPC(8): C07D251/16
Inventor 沈运河孙玉文徐庆丰于扩余正莲许社标陈玲琳王友定范富云赵晓俊
Owner HEFEI JIUYI AGRI DEV
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