Method for effectively preparing high-purity 1H-tebuconazole

A tebuconazole and high-purity technology is applied in the efficient preparation of high-purity 1H-tebuconazole, in the field of safety, and can solve the problems of inability to completely remove the purity of the solvent, difficult and unsatisfactory solvent distillation and recovery, and achieve high selectivity, Good thermal stability and the effect of reducing production energy consumption

Active Publication Date: 2017-09-19
JIANGSU SWORD AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthesis process has the disadvantages of difficult solvent rectification and recovery, residual solvent in the product cannot be completely removed, and the purity of the product after post-treatment is not ideal, and a kind of isomer 4H compound (Ⅳ) of 1H-tebuconazole in the detection reaction Occupy a certain proportion

Method used

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  • Method for effectively preparing high-purity 1H-tebuconazole
  • Method for effectively preparing high-purity 1H-tebuconazole
  • Method for effectively preparing high-purity 1H-tebuconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Put 200g 2-(4-chlorophenethyl)-2-tert-butyl oxirane, 200g triazole, 90g PEG-7000, 38g KOH and 0.6g 18- Crown-6, add 400g of 2-(4-chlorophenethyl)-2-tert-butyl oxirane into the dropping funnel to be added dropwise. Start stirring, and when the temperature rises to 108°C, start to drop 2-(4-chlorophenethyl)-2-tert-butyl oxirane, control the temperature in the reaction bottle not to exceed 112°C, add dropwise for 2 hours, after the dropwise addition , control the temperature in the reaction bottle at 108-112°C, keep it warm for 5 hours; then raise the temperature to 125-128°C, keep it warm for 8 hours, take a sample test, the raw material peak is less than 0.5%, 4-H isomer 0.3%, add to the reaction bottle Sufficient water and methylcyclohexane, wherein the mass ratio of water and methylcyclohexane is 1:3.5; after layering, the water layer cools down and crystallizes to precipitate PEG, and the solid PEG is recovered by suction filtration; the organic layer cools...

Embodiment 2

[0027] Embodiment 2: drop into 200g 2-(4-chlorophenethyl)-2-tert-butyl oxirane, 180g triazole, 60g PEG-7000 and 30g KOH in the clean 1000ml four-necked bottle, mix 400g 2- (4-Chlorophenethyl)-2-tert-butyl oxirane was added to the dropping funnel to be added dropwise. Start stirring, and when the temperature rises to 105°C, start to add 2-(4-chlorophenethyl)-2-tert-butyloxirane dropwise, and control the temperature in the reaction bottle not to exceed 112°C, and add dropwise for 2 hours. After the dropwise addition, control the temperature in the reaction bottle at 108-112°C and keep it warm for 5h; then raise the temperature to 120-125°C and keep it warm for 8h. Sampling test shows that the raw material peak is less than 0.5%, and the 4-H isomer is 1.5%. Add enough water and methylcyclohexane into the reaction bottle, wherein the mass ratio of water and methylcyclohexane is 1:3; after layering, the water layer cools down and crystallizes to precipitate PEG, and the solid PEG i...

Embodiment 3

[0029] Embodiment 3: drop into 200g 2-(4-chlorophenethyl)-2-tert-butyl oxirane, 240g triazole, 120g PEG-8000 and 48g KOH in the clean 1000ml four-necked bottle, 400g 2- (4-Chlorophenethyl)-2-tert-butyl oxirane was added to the dropping funnel to be added dropwise. Start stirring, and when the temperature rises to 106°C, start to add 2-(4-chlorophenethyl)-2-tert-butyloxirane dropwise, and control the temperature in the reaction bottle not to exceed 112°C, and add dropwise for 6 hours. After the dropwise addition, control the temperature in the reaction bottle at 108-112°C and keep it warm for 5 hours; then raise the temperature to 128-130°C and keep it warm for 8 hours; sampling test shows that the raw material peak is less than 0.5%, and the 4-H isomer is less than 1.7%. Add enough water and methylcyclohexane into the reaction bottle, wherein the mass ratio of water and methylcyclohexane is 1:4; after layering, the water layer cools down and crystallizes to precipitate PEG, an...

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Abstract

The invention discloses a method for effectively preparing high-purity 1H-tebuconazole. The method comprises the following steps: putting penta-epoxide(2-(4-chlorophenyl ethyl)-2-tert-butyl epoxyethane), triazole, caustic soda flake, polyethyleneglycol (PEG) and a crown ether catalyst into a reaction kettle and uniformly stirring; heating the system to 105 to 108 DEG C, and dropwise adding the penta-epoxide in a high-level groove into the reaction kettle; heating twice and carrying out heat preservation twice after dropwise addition is completed until the penta-epoxide is completely reacted; cooling the system to a room temperature, adding water and crystallization solvents; standing and layering; cooling and crystallizing an organic layer and separating out 1H-tebuconazole; washing the 1H-tebuconazole with water until pH reaches 7 to 8 to obtain the 1H-tebuconazole; cooling and crystallizing a water layer and separating out the PEG, and recycling the PEG to be applied. According to the method disclosed by the invention, the PEG and the crown ether catalyst are combined and applied to the synthesis of the 1H-tebuconazole, and the obtained 1H-tebuconazole is high in yield and high in purity; moreover, the content of a byproduct is low, and the quality of the 1H-tebuconazole prepared by adopting the method is much higher than that of a product prepared by adopting an existing process.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a safe and efficient method for preparing high-purity 1H-tebuconazole. Background technique [0002] 1H-tebuconazole (III) is a high-efficiency, broad-spectrum systemic triazole fungicidal pesticide, which is mainly used to prevent and control various fungal diseases on crops such as rice, peanuts, wheat, apples, bananas, and corn. It has the advantages of low toxicity and high efficiency, so it has been widely researched and applied. [0003] At present, the preparation of 1H-tebuconazole (III) mostly uses p-chlorobenzaldehyde as the starting material, and is realized through aldehyde and ketone condensation, catalytic hydrogenation, epoxidation reaction, and addition reaction. In the last step of the addition reaction, in the prior art, aprotic polar compounds such as dimethylformamide (DMF), N-methylpyrrolidone (N-MP) and dimethyl sulfoxide (DMSO) are mostl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08
CPCC07D249/08
Inventor 刘志勇朱鹏姚学林李明
Owner JIANGSU SWORD AGROCHEM
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