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Preparation method of difenoconazole technical material

A difenoconazole and production method technology, applied in the field of triazole fungicides, can solve the problems of easy recovery, high isomer content, low bromide conversion rate, etc., and achieve improved yield, high conversion rate, Effect of reducing isomer content

Active Publication Date: 2009-10-21
利民化学有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the shortcomings of low bromide conversion rate, high isomer content, and poor solvent recovery and utilization in the prior art, the invention provides a production method of difenoconazole active drug, which has a high bromide conversion rate , low isomer content and easy solvent recovery

Method used

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  • Preparation method of difenoconazole technical material
  • Preparation method of difenoconazole technical material
  • Preparation method of difenoconazole technical material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] In the 3000L enamel reaction kettle, add 4-(4-chlorophenoxy group)-2-chloroacetophenone 500KG of content 98%wt, under solvent hexanaphthene 2000L and catalyzer p-toluenesulfonic acid condition and 1 , 2-propanediol 160 ~ 200KG reflux reaction, continuous separation of water, to obtain a cyclohexane solution containing cyclized products, after making phenyl ether ketone ≤ 1.0 (liquid chromatography, L = 150mm, T = 40 ° C, wavelength 220) , lower the temperature to 20-25°C, and let stand to remove excess 1,2-propanediol. Then add 3% to 10% of the total amount of bromine required into the reaction kettle, and keep it warm for about 10 to 30 minutes at 20 to 25°C. When white smoke is emitted from the kettle, it proves that the bromination initiation is successful. Add the remaining 90%-97% bromine dropwise at 20-25°C, and the time is controlled within 2-3 hours. After dripping, keep warm for 1 hour, add water to wash until neutral, and evaporate cyclohexane under reduced p...

Embodiment 2

[0019] Under the conditions of Example 1, add 1,2,4-triazole 150KG (92%wt) and potassium hydroxide 142KG (92%wt) in the enamel reaction kettle, under the condition of toluene as solvent, reflux at 110°C water to obtain potassium 1,2,4-triazole, evaporate toluene, add 1800L of N-methylpyrrolidone, add the bromide prepared in Example 1, and react at 155°C to 160°C for about 20 hours to obtain diphenoxymethylcycline For crude azoles, evaporate pyrrolidone, add benzyl bromide accounting for 0.5% of the mass of the crude product, and keep warm for 1 to 3 hours at 200°C to 300°C for isomer conversion, then enter the high vacuum distillation process for distillation, and then go through the crystallization process (See Example 3 for details), to obtain difenoconazole.

[0020] Table 3 Without the use of isomer conversion agent

[0021]

[0022]

[0023] Table 4 using isomer conversion agent

[0024]

[0025] The results show that: the quality and yield of difenoconazole ar...

Embodiment 3

[0027] Under the conditions of Example 1 and Example 2, difenoconazole oil obtained by high-vacuum distillation was added to an enamel reaction kettle, and a single solvent methanol was added, heated to 60°C to dissolve it, kept for one hour, and then cooled to 10 ℃, add a small amount of crystallization aid polyacrylamide, the crystallization aid accounts for 0.05-10% of the mass of methanol, keep at 10°C for 10 hours, at 5°C for 10 hours, at 0°C for 10 hours, at -5°C for 8 hours Hours, after centrifugation to obtain a wet product, put the wet product into the enamel reaction kettle, add 0.5 times of fresh methanol, then cool down to -5 ° C for 5 hours, and then centrifuge to obtain a wet product.

[0028] The feasibility of long-term application of solvents is verified theoretically and practically. Prior to the present invention, binary solvents were used as alcohols and ethers with a fixed volume ratio. Due to their different boiling points, ethers are volatile substances...

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Abstract

The invention provides a preparation method of difenoconazole technical material. 4-(4-chlorophenoxy)-2-chloroacetophenone performs cyclization reaction with 1,2-propylene glycol to generate cis / trans-3-chloro-4-(2,4-dimethyl-1,3-dioxolan-2-yl)phenyl-4'-chlorphenyl ether, then carries out bromination reaction with bromine to generate cis, / trans-3-chloro-4-(4-methyl-2-bromomethyl-1,3-dioxolan-2-yl)phenyl-4'-chlorphenyl ether, and carries out condensation reaction with 1, 2, 4-triazole potassium to prepare a crude product; a product is obtained after the crude product suffers from refining, desolvation, reduced pressure distillation , crystallization and centrifugation, bromine is added at twice while carrying out bromination reaction after cyclization reaction is over, bromine accounting for 3%-10% of total mass is added to reaction system for initiation reaction, remanent bromine is added after 10-30 minutes for reacting for 2-3 hours. Benzyl bromide accounting for 0.5%-5% of the quality of the crude product is added into the prepared crude product while refining the crude product, and heat is preserved for 1-3 hours at 200-300 DEG C.

Description

technical field [0001] The invention relates to a production method of a triazole fungicide, in particular to a production method of difenoconazole technical substance. Background technique [0002] Difenoconazole is a high-efficiency triazole fungicide with unique crop safety. It can show the three functions of prevention, treatment and eradication. Using the intermediate 4-(4-chlorophenoxy)-2-chloroacetophenone as raw material, the crude product is obtained through a three-step synthesis process of cyclization, bromination, and condensation, and then the qualified product is obtained through product refining, such as the application number It is the method adopted in the patent of 2004100654047.5. In the production method that generally adopts at present, there are following disadvantages: 1) cyclized compound is an unstable substance, and reversible reaction easily occurs during bromination, and produces about 5% bromine derivatives simultaneously, and the conversion ra...

Claims

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Application Information

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IPC IPC(8): C07D405/06
Inventor 孙敬权许宜伟陆伟刘振
Owner 利民化学有限责任公司
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