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Preparation method of mesotrione intermediate

A mesotrione and intermediate technology, which is applied in the field of organic synthesis, can solve the problems of unfriendly environment and high recovery cost of vanadium pentoxide, and achieve the effects of avoiding interaction, realizing reuse and simple preparation method.

Active Publication Date: 2019-09-13
湖北广富林生物制剂有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalyst vanadium pentoxide used in the method is a highly toxic reagent, the recovery cost of vanadium pentoxide is high, and it is not friendly to the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A preparation method of a mesotrione intermediate, comprising the following steps: (1) nitration, adding 1300g of concentrated sulfuric acid, 350g of p-thiamphenicol and 300g of water in a nitration reactor, and adding 200g of nitric acid dropwise within 3 to 4 hours Carry out nitration reaction, after dropwise addition, heat preservation reaction 1~2h, obtain 2-nitro-4-thiamphenicol toluene; (2) catalytic oxidation, add concentrated sulfuric acid in oxidation reactor, add step (1 ) of the resulting 2-nitro-4-thiamphenicol toluene and 2.88g CuO / MnFe 2 o 4 Catalyst, slowly add 875.5g of 40% hydrogen peroxide dropwise therein while stirring at 60-80°C, complete the dropwise addition within 2-3 hours, and then continue to react for 3-4 hours until the reaction is completed to obtain a crude product reaction solution; (3) refining, Separating the catalyst from the reaction liquid by applying an external magnetic field while it is hot to realize the recovery of the catalyst...

Embodiment 2

[0034] A preparation method of a mesotrione intermediate, comprising the following steps: (1) nitration, adding 1500g of concentrated sulfuric acid, 370g of p-thiamphenicol and 330g of water in a nitration reactor, and adding 210g of nitric acid dropwise within 3 to 4 hours Carry out nitration reaction, after dropwise addition, heat preservation reaction 1~2h, obtain 2-nitro-4-thiamphenicol toluene; (2) catalytic oxidation, add concentrated sulfuric acid in oxidation reactor, add step (1 ) of the resulting 2-nitro-4-thiamphenicol toluene and 2.76g CuO / CoFe 2 o 4 Catalyst, 1478.32g of 50% hydrogen peroxide was slowly added dropwise to it while stirring at 60-80°C, and the dropwise addition was completed within 2-3 hours, and then continued to react for 3-4 hours until the reaction was completed to obtain a crude product reaction solution; (3) refining, The catalyst is separated from the reaction solution by applying a magnetic field while it is hot to realize the recovery of t...

Embodiment 3

[0036] A preparation method of a mesotrione intermediate, comprising the following steps: (1) nitration, adding 1400g of concentrated sulfuric acid, 360g of p-thiamphenicol and 320g of water in a nitration reactor, and adding 205g of nitric acid dropwise within 3 to 4 hours Carry out nitration reaction, after dropwise addition, heat preservation reaction 1~2h, obtain 2-nitro-4-thiamphenicol toluene; (2) catalytic oxidation, add concentrated sulfuric acid in oxidation reactor, add step (1 ) The resulting 2-nitro-4-thiamphenicol toluene and 2.96g CuO / MgFe 2 o 4 Catalyst, slowly add 1118.6g of 45% hydrogen peroxide dropwise therein while stirring at 60-80°C, complete the dropwise addition within 2-3 hours, and then continue to react for 3-4 hours until the reaction is completed to obtain a crude reaction solution; (3) refining, Separating the catalyst from the reaction liquid by applying a magnetic field while it is hot to realize the recovery of the catalyst, then cooling the c...

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PUM

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a preparation method of a mesotrione intermediate. The preparation method comprises the following steps: nitrification:adding concentrated sulfuric acid, p-methylsulfonyltoluene and water into a nitrification reactor, and carrying out a nitration reaction by dropwise adding nitric acid so as to obtain 2-nitro-4-methylsulfonyltoluene; catalytic oxidation: adding concentrated sulfuric acid into an oxidation reaction kettle, adding 2-nitro-4-methylsulfonyltoluene and a CuO / MFe2O4 catalyst, dropwise adding hydrogen peroxide while stirring, reacting for a certain period of time after the dropwise addition so as to obtain a crude product reaction solution; refining: separating the catalyst from the reaction solution by additionally arranging an external magnetic field while it is hot, cooling the reaction solution and precipitating out a crude product, rinsing with water, refining for multiple times, and dryingto obtain 2-nitro-4-methylsulfonylbenzoic acid. In the preparation method of the invention, green and environmentally-friendly hydrogen peroxide is used as an oxidant, thus reducing environmental pollution; and the catalyst used in the reaction has high catalytic efficiency and magnetic property, and the catalyst can be conveniently and quickly recovered.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of a mesotrione intermediate. 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. It was developed and produced by Zhengda Company, and started selling in Europe in 2001 under the trade name callisto. Mesotrione can inhibit p-hydroxyphenylpyruvate dioxygenase (HPPD), which ultimately affects the biosynthesis of carotenoids. HPPD is a key enzyme in the biosynthetic pathway of plastoquinone and tocopherol necessary for the normal growth of plants. It can catalyze the biochemical process from tyrosine to plastoquinone in plants. HPPD is currently one of the most important targets of herbicides. one. Mesotrione has the characteristics of wide herbicidal spectrum, high activity, strong mixability, safety to subsequent crops, flexible u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/14C07C317/44B01J23/889B01J23/75B01J23/78B01J23/755
CPCC07C315/04B01J23/8892B01J23/75B01J23/78B01J23/755B01J23/002B01J2523/00B01J35/33C07C317/14C07C317/44B01J2523/17B01J2523/72B01J2523/842B01J2523/845B01J2523/22B01J2523/41
Inventor 牛巍张晓臣李萍张强
Owner 湖北广富林生物制剂有限公司