Preparation method of mesotrione

A technology of mesotrione and methylbenzenesulfonyl chloride, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry and other directions, can solve the problems of high cost, lack of competitiveness, expensive anhydrous bromine and the like , to achieve the effect of easy circulation, environmental friendliness, and reduced pressure

Active Publication Date: 2014-05-07
INSIGHT FINECHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route has a certain novelty, but the process needs to use expensive anhydrous bromine, and the cost is high. At present, it is only suitable for the preparation of a small amount of samples in the laboratory, and the large-scale industrial production is not competitive.

Method used

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  • Preparation method of mesotrione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (1) Synthesis of 3-nitro-4-methylbenzenesulfonyl chloride

[0054] Add chlorosulfonic acid (559.2g / 4.8mol) into a 1L four-neck flask, heat up to 110-115°C, maintain the temperature, slowly add o-nitrotoluene (548.0g / 4.0mol) dropwise, the dropwise addition is complete, Continue the heat preservation reaction for 3.5 hours, stop the reaction, cool the reaction solution to 60-65°C, add 1mL of DMF, maintain the temperature, slowly add thionyl chloride (547.5g / 4.6mol) dropwise, and continue the heat preservation reaction for 3 hours, a mixture of 3-nitro-4-methylbenzenesulfonyl chloride was obtained, which was directly used in the next reaction.

[0055] (2) Synthesis of 2-nitro-4-thiamphenicol toluene (NMST)

[0056] Add sodium sulfite (479.0g / 3.7mol), sodium carbonate (763.0g / 7.2mol) and 6L water in sequence into a 10L four-neck flask, stir and mix well, control the temperature at 0-5°C, and slowly add step (1) The obtained mixed solution of 3-nitro-4-methylbenzenesulfon...

Embodiment 2

[0066] (1) Synthesis of 3-nitro-4-methylbenzenesulfonyl chloride

[0067] Add chlorosulfonic acid (559.2g / 4.8mol) into a 1L four-necked flask, heat up to 90-100°C, maintain the temperature, slowly add o-nitrotoluene (548.0g / 4.0mol) dropwise, the dropwise addition is complete, Continue the heat preservation reaction for 4 hours, stop the reaction, cool the reaction solution to 50-55°C, add 1mL DMF, maintain the temperature, slowly add thionyl chloride (547.5g / 4.6mol) dropwise, after the addition is complete, continue the heat preservation reaction for 4.5 hours , that is, a mixture of 3-nitro-4-methylbenzenesulfonyl chloride was directly used in the next reaction.

[0068] (2) Synthesis of 2-nitro-4-thiamphenicol toluene (NMST)

[0069] In a 10L four-neck flask, add sodium sulfite (479.0g / 3.7mol), sodium carbonate (763.0g / 7.2mol) and 6L water in sequence, stir and mix well, use an ice-water bath to control the temperature at 0-5°C, and slowly drop the steps (1) The obtained m...

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Abstract

The invention provides a preparation method of mesotrione. The preparation method comprises is capable of preparing the target product from raw materials such as ortho-nitrotoluene, chlorosulfonic acid, sulfoxide chloride, sodium sulfite, chloroactic acid, 1,3-cyclohexanedione in the presence of a catalyst and acid-base. The preparation method is based on common chemical raw materials, the reaction flow of each step is implemented under conventional operation conditions, the amount of three wastes is low, the total yield is above 61%, the purity of the product is high, the purity of the coarse product of the mesotrione is greater than 98%, and the coarse product of the mesotrione can be further purified; as a result, the preparation method of mesotrione is applicable to large-scale industrial production.

Description

technical field [0001] The invention relates to a herbicide mesotrione (2-(2-nitro-4-thiasulfonyl-benzoyl)cyclohexane-1,3-dione, referred to as MST, also known as nitrosulfone Grass ketone, mesotrione) preparation method. Background technique [0002] Mesotrione, 2-(2-nitro-4-thiasulfonyl-benzoyl)cyclohexane-1,3-dione (MST), also known as nitrosulcotrione, mesotrione, It is a triketone herbicide variety developed by Swiss Syngenta Company. It is an inhibitor of hydroxypyruvate dioxygenase (HPPD), which can convert tyrosine into plastoquinone. By modifying the structure of sulcotrione, mesotrione has a biological activity more than 10 times that of sulcotrione, so it has better development potential and market competitiveness. As a new type of systemic herbicide dedicated to corn fields, it has a wide herbicidal spectrum, high activity, strong miscibility, low toxicity, environmental friendliness, safety to subsequent crops, and flexible use. Great success, it also has grea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/24C07C315/04
Inventor 李永芳黄碧波凌云罗海章
Owner INSIGHT FINECHEM
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