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Synthetic process of methyl sulcotrione

A technology of mesotrione and synthesis process, which is applied in the field of synthesis process of mesotrione, can solve the problems of high risk of phosgene, difficulty in separation, complex process, etc., and achieve avoidance of tail gas treatment, reduction of reaction steps, Reduce the effect of wastewater treatment

Inactive Publication Date: 2019-05-28
ANHUI FENGLE AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of thionyl chloride for chlorination reaction will produce mixed tail gas of sulfur dioxide and hydrogen chloride, and it is not easy to separate. In addition, the use of phosgene is very dangerous
So this process needs to be improved
In addition, the addition of acid-binding agents not only increases the cost, but also produces a large amount of saline wastewater, especially the addition of organic bases needs to be recycled, making the process more complicated

Method used

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  • Synthetic process of methyl sulcotrione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Put 13 grams of 2-nitro-4-thiamphenicol benzoic acid and 6 grams of 1,3-cyclohexanedione into a three-necked flask with a stirrer and a condenser tube, then add 250 milliliters of xylene, 0.1 grams of trifluoro Phenylboronic acid and 10 g of dicyclohexylcarbodiimide were heated to reflux at 140-150°C under stirring for condensation reaction, followed by TLC to complete the reaction, rearrangement reaction in acetonitrile, and finally post-treatment to obtain the target compound Mesotrione has a content of 98.0% and a yield of 80.3%.

Embodiment 2

[0019] Put 13 grams of 2-nitro-4-thiamphenicol benzoic acid and 6 grams of 1,3-cyclohexanedione into a three-necked flask with a stirrer and a condenser, add 250 milliliters of xylene, and 0.05 grams of trifluorophenylboronic acid , 10 grams of dicyclohexylcarbodiimide, under stirring and heating to 140-150 ° C reflux. After the completion of the condensation reaction (TLC tracking), it was processed, then rearranged, and finally post-treated to obtain the target compound with a content of 96.6% and a yield of 77.3%.

Embodiment 3

[0021] Put 13 grams of 2-nitro-4-thiamphenicol benzoic acid and 6 grams of 1,3-cyclohexanedione into a three-necked flask with a stirrer and a condenser tube, add 250 milliliters of monochlorobenzene, trifluorophenylboronic acid 0.1 gram, 10 grams of dicyclohexylcarbodiimide, under stirring and heating up to 140-150 ℃ reflux. After the completion of the condensation reaction (TLC tracking), it was processed, and then rearranged, and finally post-treated to obtain the target compound with a content of 93.5% and a yield of 75.1%.

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Abstract

The invention discloses a synthetic process of methyl sulcotrione. 2-nitro-4-methylsulfony benzoic acid and 1,3-cyclohexanedione are added into a solvent, then, a catalyst and an addition agent are added, temperature is raised to 140-150 DEG C under stirring, and condensation reaction is directly carried out; and then, rearrangement is carried out to obtain the methyl sulcotrione. According to thesynthetic process of the methyl sulcotrione, the catalyst and the addition agent are added for dehydration, so that the condensation reaction is directly carried out on the 2-nitro-4-methylsulfony benzoic acid and the 1,3-cyclohexanedione; and then, the rearrangement is carried out to obtain a methyl sulcotrione product. Due to no adding of thionyl chloride or phosgene for chlorination, reactionsteps are reduced, and meanwhile, tail gas treatment or production safety is further avoided; and in addition, acid-binding agents are not added, and later wastewater treatment is reduced. Therefore,used raw materials are less, and greenness, environmental protection and no pollution are achieved.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a synthesis process of mesotrione. Background technique [0002] Mesotrione is also known as mesotrione and mesotrione, and its chemical name is 2-(4-methylsulfonyl 2-nitro-benzoyl)cyclohexane-1,3-dione, which was developed by Xian Zheng A herbicide that inhibits p-hydroxyphenylpyruvate dioxygenase developed by Dada Company. As a new type of systemic herbicide dedicated to cornfields, mesotrione has the characteristics of broad herbicidal spectrum, high activity, strong miscibility, safety to subsequent crops, flexible use, and strong environmental compatibility. It has great development value and good prospects for promotion and use in our country. [0003] At present, most of the synthetic routes of domestic mesotrione are to react 2-nitro-4-thiamphenicol benzoic acid with thionyl chloride or phosgene to obtain 2-nitro-4-thiamphenicol benzoyl chloride, ...

Claims

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Application Information

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IPC IPC(8): C07C317/24C07C315/04
Inventor 周康伦苏朝辉施亦敏
Owner ANHUI FENGLE AGROCHEM
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