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Production method of mesotrione

A production method, the technology of mesotrione, is applied in the production field of the new herbicide mesotrione, and achieves the effects of reducing production costs and being environmentally friendly

Inactive Publication Date: 2014-08-06
JIANGSU CHANGLONG AGROCHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage is that sodium cyanide and potassium cyanide are also highly toxic

Method used

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  • Production method of mesotrione

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Experimental program
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Effect test

Embodiment 1

[0025] Preparation of mesotrione: In a reaction flask, add 300g (0.88mol) 3-(2-nitro-4-thiamphenicol benzoyl chloride)-2-cyclohexen-1-one, 2500ml acetonitrile, 4.5 g (0.044mol) triethylamine, 30g potassium ferrocyanide (0.071mol), stirred and heated, the reaction temperature was 50°C, reacted for 15h, cooled, and filtered to obtain 31.8 grams of wet product translocation agent, and the filtrate was mixed with 2mol / Acidify with L hydrochloric acid to make the pH value 2-3, add 2500ml dichloromethane after desolventization to dissolve and separate the layers, separate the organic layer, wash twice with 5000ml water, desolventize the organic phase, and crystallize to obtain 264g mesotrione with a yield of 88 %.

Embodiment 2

[0027] Preparation of mesotrione: In a reaction flask, add 300g (0.88mol) 3-(2-nitro-4-thiamphenicol benzoyl chloride)-2-cyclohexen-1-one, 2500ml acetonitrile, 4.5 g (0.044mol) triethylamine, Example 1 filter out 31.8 grams of wet product potassium ferrocyanide recovered, stir and heat, the reaction temperature is at 50°C, react for 15h, cool, filter, acidify with 2mol / L hydrochloric acid, make The pH value is 2-3. After precipitation, 2500ml of dichloromethane is added to dissolve and separate the layers. The organic layer is separated and washed twice with 5000ml of water. The organic phase is precipitated and crystallized to obtain 255g of mesotrione with a yield of 85%.

Embodiment 3

[0029] The preparation of mesotrione: in reaction flask, add 300g (0.88mol) 3-(2-nitro-4-thiamphenicol benzoyl chloride)-2-cyclohexen-1-one, 2500ml dichloromethane , 150g (1.4mol) triethylamine, 30g potassium ferrocyanide (0.071mol), stir and heat, the reaction temperature is 10°C, react for 20h, cool, filter, acidify with hydrochloric acid, make the pH value 2-3, let stand Separate the layers, separate the organic layer, wash twice with 5000ml of water, desolventize the organic phase, and crystallize to obtain 240g of mesotrione, with a yield of 80%.

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Abstract

The invention discloses a production method of mesotrione. The production method comprises the steps of carrying out rearrangement reaction on 3-(2-nitro-4-methylsulfurylbenzoyloxy)-2-cyclohexene-1-ketone under the action of a translocation agent, and then, filtering and separating the reaction liquid to obtain mesotrione, wherein the translocation agent (potassium ferricyanide / potassium ferrocyanide) can be recycled. The production method has the beneficial effects that (1) as the translocation agent in the production method of mesotrione, potassium ferricyanide or potassium ferrocyanide is basically nontoxic and environment-friendly; (2) the translocation agent used in the production method of mesotrione can be filtered, recovered and reutilized, so that the production cost is lowered.

Description

technical field [0001] The invention relates to a new herbicide Mesotrione (Mesotrione) production method, specifically, from 3-(2-nitro-4-thiamphenicol benzoyloxy)-2-cyclohexene-1 -A method for producing mesotrione through a rearrangement reaction of ketones. Background technique [0002] Mesotrione is a herbicide suitable for pre-emergence and post-emergence weeds in corn fields. It has the characteristics of broad-spectrum, high efficiency, good compatibility with the environment, and low toxicity to mammals and aquatic organisms. [0003] The prior art is all based on 3-(2-nitro-4-thiamphenicol benzoyloxy)-2-cyclohexen-1-ketone (2-nitro-4-thiamphenicol-benzene Formyl chloride and 1,3-cyclohexanedione are obtained conveniently) under alkaline conditions, select rearrangement agent to carry out rearrangement to produce mesotrione. [0004] US476255, US4775411 and US20030232984 disclose that triethylamine is used as an alkaline reagent to rearrange to generate mesotrione ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/24C07C315/04
Inventor 田庆海陆明若杨建元马志荣张昭荣陈雪林
Owner JIANGSU CHANGLONG AGROCHEM CO LTD
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