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A process for preparing ethiprole by oxidation method

An ethiprole, oxidation technology, applied in the direction of organic chemistry, etc., can solve the problems of high toxicity of raw materials, high pollution, complicated separation and so on

Active Publication Date: 2017-04-05
ZHEJIANG HISUN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The existing production process of ethiprole generally faces problems such as high cost, high toxicity of raw materials, high pollution, low yield, complicated separation, etc.

Method used

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  • A process for preparing ethiprole by oxidation method
  • A process for preparing ethiprole by oxidation method
  • A process for preparing ethiprole by oxidation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] With 10.287kg (27mol) acetonitrile oxidation precursor, 107.26kg (1083mol) dichloroethane is added in 100L reactor, add acetic acid 4.212kg (70.2mol) and 35% hydrogen peroxide 6.8175kg (70.2mol), 30 ℃ of stirring about 10 hours. Sampling and tracking, after the reaction is completed, slowly add 3.285kg (31.6mol) of sodium sulfite, the exotherm is obvious, and the temperature is controlled within 55°C. Add sodium hydroxide solution to adjust pH to 6-7, then heat up and reflux (about 80 ℃) and then cool to below 10 ℃, crystallize, suction filtration to obtain 10.50kg of crude solid, purity 98.7%, crude product yield 96%, containing The amount of peroxide impurity is 0.5%, and after one recrystallization, a fine product with a peroxide impurity less than 0.3% is obtained, and the yield of the fine product is 93%.

[0037] Purity of synthetic ethiranil: 99.4% (HPLC).

Embodiment 2

[0039] With 10.287kg (27mol) ethiprole oxidation precursor, 107.26kg (1083mol) dichloroethane layer is added in 100L reactor, add acetic acid 1.62kg (27mol) and 35% hydrogen peroxide 6.8175kg (70.2mol), 30 ℃ of stirring About 20 hours. Sampling and tracking, after the reaction is completed, slowly add 3.285kg (31.6mol) of sodium sulfite, the exotherm is obvious, and the temperature is controlled within 55°C. Add sodium hydroxide solution to adjust pH to 6-7, then heat up and reflux (about 80 ° C) and then cool to below 10 ° C, crystallize, and suction filtration to obtain 10.41kg of crude solid, purity 98.3%, crude product yield 95%, containing The amount of peroxide impurity is 0.6%. After one recrystallization, a fine product with a peroxide impurity less than 0.3% is obtained, and the yield of the fine product is 92%.

[0040] Purity of synthetic ethiranil: 99.3% (HPLC).

Embodiment 3

[0042] With 10.287kg (27mol) acetonitrile oxidation precursor, 107.26kg (1083mol) dichloroethane layer is added in 100L reactor, add acetic acid 4.212kg (70.2mol) and 35% hydrogen peroxide 6.8175kg (70.2mol), 30 ℃ Stir for about 18 hours. Sampling and tracking, after the reaction is completed, slowly add 3.285kg (31.6mol) of sodium sulfite, the exotherm is obvious, and the temperature is controlled within 55°C. Add sodium hydroxide solution to adjust pH to 6-7, then heat up and reflux (about 80 ° C) and then cool to below 10 ° C, crystallize, and suction filtration to obtain 10.40kg of crude solid, purity 97.8%, crude product yield 95%, containing The amount of peroxide impurity is 0.8%, and after recrystallization twice, a fine product with a peroxide impurity less than 0.3% is obtained, and the yield of the fine product is 91%.

[0043] Purity of synthetic ethiranil: 99.1% (HPLC).

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Abstract

The invention discloses a process for preparing high-purity ethiprole through an oxidation method. The process comprises the following steps of: carrying out oxidation reaction on a right amount of raw material 5-amido-3-cyano-group-1-(2,6-dichloro-4-trifluoromethyl phenyl)-4-ethyl sulfinyl pyrazole (I) in an organic solvent with the participation of fatty acid and hydrogen peroxide; after the oxidation reaction is finished, adding a reducing agent and controlling the temperature of a system at the same time; then regulating the pH value of the system through an NaOH solution; then heating, refluxing, cooling, crystallizing and carrying out suction filtration to obtain a crude ethiprole product; purifying the crude ethiprole product (II) so as to obtain a qualified product, wherein the organic solvent is selected from at least one of chloroform, dichloromethane and dichloroethane. The production process disclosed by the invention has the advantages of simplicity, high efficiency, few by-products, bigger breakthrough on product yield and product purity, relatively low raw material toxicity, little environmental pollution and good production controllability.

Description

technical field [0001] The invention relates to a production, preparation and purification process method of N-phenylpyrazole compounds, in particular to a production and preparation method of ethiprole. Background technique [0002] Ethopronil is an arylpyrazole insecticide with similar biological properties to butenefipronil. It is a low-toxic insecticide, non-mutagenic, non-irritating and non-sensitizing to skin and eye nitrile, effective for a variety of chewing and sucking pests, the mode of action is contact killing, and its mechanism of action is through γ - Aminobutyl ester interferes with chloride ion channels, thereby disrupting the normal activity of the central nervous system and causing the death of pests. Commercially available products are generally 100 g / L suspending agent. [0003] Ethopranil is effective against a variety of chewing and sucking pests at low dosages, and can be used for seed treatment and foliar spraying with a lasting effect of up to 21-2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/44
CPCC07D231/44
Inventor 包如胜王丽敏蒋富国李劲徐坚勇
Owner ZHEJIANG HISUN CHEM
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