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Synthesis method of mesotrione

A technology of mesotrione and its synthetic method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve complete reaction, high yield and simple operation

Inactive Publication Date: 2016-01-20
SHANGYU NUTRICHEM +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] In order to solve the problems in the existing mesotrione production process, the invention provides a synthetic method of mesotrione, the method has mild reaction conditions, high conversion rate of each step, high yield and purity of the product, and production The whole process does not involve highly toxic and odorous materials, high safety, low equipment and material costs, suitable for large-scale industrial production

Method used

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  • Synthesis method of mesotrione
  • Synthesis method of mesotrione
  • Synthesis method of mesotrione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Synthesis of acylate: Turn on the tail gas absorption system, add 185g (0.3eqv) of solid phosgene (acylating agent) and 450g of toluene to the four-neck flask, stir in a water bath and heat up to 70-80°C until the solid phosgene is complete Dissolve and keep warm for later use. Add 2-nitro-4-thiamphenicol benzoic acid 460g, toluene 1150g and trace 0.1g depolymerizing agent DMF (0.02wt%) in the acylation reaction flask meter), heated to 50°C (acylation reaction temperature) under stirring, and started to drop the pre-configured solid phosgene toluene solution. After the dropwise addition, continue the reaction for about 2 hours. , to obtain the acylation reaction solution.

[0052] (2) Synthesis of esterified product: Add 210g (1.0eqv) of cyclohexanedione and 154.3g (0.6eqv) of potassium carbonate (acid-binding agent) to the acylation reaction solution, heat up to 55°C, react for 8 hours, and cool down to obtain Esterification reaction solution.

[0053] (3) Synth...

Embodiment 2

[0056] Compared with Example 1, the difference is that thionyl chloride is used as an acylating agent, and the dosage equivalent of thionyl chloride is 1.2eqv. After the reaction treatment was completed, the chromatographic purity of the obtained mesotrione was 91.0%, and the yield was 86.6%.

Embodiment 3

[0058] (1) Synthesis of acylate: open the tail gas absorption system, add 446g (0.8eqv) of solid phosgene (acylating agent) and 450g of toluene to the four-neck flask, stir and raise the temperature to 70-80°C in a water bath until the solid phosgene is complete Dissolve and keep warm for later use. Add 2-nitro-4-thiamphenicol benzoic acid 460g, toluene 1150g and trace 0.2g depolymerizing agent DMF (0.04wt%) in the acylation reaction flask meter), heated to 70°C (acylation reaction temperature) under stirring, and started to drop the pre-configured solid phosgene toluene solution. After the dropwise addition, continue to react for about 2 hours. , to obtain the acylation reaction solution.

[0059] (2) Synthesis of esterified product: Add 273g (1.3eqv) of cyclohexanedione and 154.3g (0.6eqv) of potassium carbonate (acid-binding agent) to the acylation reaction solution, heat up to 55°C, react for 8 hours, and cool down to obtain Esterification reaction solution.

[0060] (3...

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Abstract

The invention discloses a synthesis method of mesotrione. The method includes the following steps that firstly, acylation is performed, wherein 2-nitro-4-methylsulfonylbenzoic acid and acylating agents are subjected to an acylation reaction under catalysis of depolymerizing agents, acylation reaction liquid is obtained, and the temperature of the acylation reaction is 10-70 DEG C; secondly, esterification is performed, wherein acid binding agents and 1,3-cyclohexanedione are added in esterification reaction liquid, an esterification reaction is performed, the esterification reaction liquid is obtained, the temperature of the esterification reaction is 30-65 DEG C, and the acid binding agents are inorganic acid; thirdly, rearrangement is performed, wherein rearrangement agents are added in the esterification reaction liquid so that a rearrangement reaction can be performed, and coarse product reaction liquid is obtained; fourthly, refining is performed, wherein the coarse product reaction liquid is subjected to alkali liquor reverse extraction, acidification and recrystallization, and mesotrione is obtained. The method is easy to operate, the raw materials are easy to obtain, the reactant conversion rate is high, reaction is thorough, the purity of the product is high, and the synthesis method is applicable to industrial production.

Description

technical field [0001] The invention relates to the technical field of herbicide production, in particular to a method for synthesizing mesotrione. Background technique [0002] Mesotrione (Mesotrione, Mesotrione), the chemical name is 2-(2-nitro-4-thiamphenicol-benzoyl)cyclohexane-1,3-dione, its structural formula is shown in the formula 1. It is a triketone herbicide developed by Syngenta in Switzerland. [0003] [0004] Mesotrione is an inhibitor of hydroxypyruvate dioxygenase (HPPD), which converts tyrosine to plastoquinone. As a systemic broad-spectrum herbicide, mesotrione can effectively control annual broad-leaved weeds and certain grass weeds, such as velvetleaf, cocklebur, amaranth, Chenopodium weeds, Kochia, barnyardgrass , Chickweed, etc. [0005] There are many synthetic methods of mesotrione, such as Yu Gang et al. (Yu Gang, Gu Ning, Qin Linqiang, Zhou Li. Synthesis of cornfield herbicide mesotrione[J].Jiangsu Agricultural Journal, 2007, 23 (6): 661-662...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/24
Inventor 冯应江陈国斌梁俊芳温沛宏申宏伟陈佳易陈均坤梅小玲孙久社胡万全徐金鹏王满
Owner SHANGYU NUTRICHEM
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