Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing difenoconazole

A technology of difenoconazole and difenoconazole, applied in the direction of organic chemistry and the like, can solve the problems of polluted environment, air pollution, loss and the like, and achieve the effects of lowering reaction temperature, reducing energy consumption and simplifying purification process

Active Publication Date: 2015-07-08
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are different disadvantages in the traditional process: the content of 1,3,4-difenoconazole isomers produced in the condensation reaction is ≥15%, it is difficult to achieve the ideal quality and yield, and it brings difficulties to the purification of the final product. a lot of difficulty
In terms of refining methods, the salt-forming-powdering method requires a large amount of organic solvent, which is also lost in the process of recovering the organic solvent, which is easy to cause air pollution. In addition, during the washing process, a large amount of waste water is produced and pollutes the environment; the distillation-powdering method will The difenoconazole crude product obtained from the condensation reaction is distilled under reduced pressure, the distillate temperature is ≥250°C, and the heating temperature is ≥300°C. High temperature poses a great safety hazard. At the same time, high temperature causes the product to decompose, producing a large amount of tar, which affects Powder yield

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing difenoconazole
  • Method for preparing difenoconazole
  • Method for preparing difenoconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Cyclobromination: 2,4-dichloroacetophenone (1.0mol), 1,2-propanediol (1.0mol) and p-toluenesulfonic acid (2g) are dissolved in cyclohexane (200g), Heat to reflux for water separation, after reflux for 4.0 hours, add 1,2-propanediol (0.1mol) and continue to reflux for water separation. After 1.0 hours of reaction, the reaction ends, cool down to 30°C, add liquid bromine (1.0mol) dropwise, and start When about (0.2mol) is added dropwise, stop the dropwise addition. After the color becomes lighter (initiation is successful), continue to dropwise add the remaining liquid bromine. After the dropwise addition, continue to react for 1.0h. Cyclohexane was recovered to obtain 329 g of brominated ketal with a content of 95% and a yield of 96%.

[0027] (2) Condensation: Dissolve triazole (1.05mol) and potassium hydroxide (1.1mol) in toluene (200g) aqueous solution, reflux and divide water, after reacting for 2.0h, bromide ketal (329g, 0.96mol) Add it to the above reaction so...

Embodiment 2

[0030] (1) Ring closure bromination: 2,4-dichloroacetophenone (1.0mol), 1,2-propanediol (1.0mol) and p-toluenesulfonic acid (2g) were dissolved in toluene (200g), heated to reflux Divide water, after reflux for 4.0 hours, add 1,2-propanediol (0.3mol), continue to reflux and divide water, after 1.0h of reaction, the reaction ends, lower the temperature to 30°C, add liquid bromine (1.0mol) dropwise, and start adding dropwise When it is about (0.2mol), stop the dropwise addition. After the color becomes lighter (initiation is successful), continue to add the remaining liquid bromine dropwise. After the dropwise addition, continue to react for 1.0h. hexane to obtain 331 g of brominated ketal with a content of 94% and a yield of 95.5%.

[0031] (2) Condensation: Dissolve triazole (1.05mol) and potassium hydroxide (1.1mol) in toluene (200g) solution, reflux to separate water, after 2.0h of reaction, bromide ketal (331g, 0.96mol) Add to the above reaction solution, distill toluene, ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to a method for preparing difenoconazole, which comprises the steps of cyclization reaction, bromination reaction, condensation reaction and etherification reaction in sequence, wherein the cyclization reaction refers to reacting 2,4-dichloroacetophenone with 1,2-propylene glycol in the presence of an acid catalyst in a solvent to form a ketal; the bromination reaction is to drip liquid bromine into a system obtained after cyclization reaction to form brominated ketal; the condensation reaction is to react the brominated ketal with triazole potassium in an N,N-dimethylformamide solvent to form metaconazole; and the etherification reaction is to react the metaconazole with p-chlorophenol potassium in a solvent at 100 to 180 DEG C to form difenoconazole. By the method, the synthesis route is reformed to reduce isomer content, increase product yield, reduce waste gas, water and residue and ensure safe operation and pollution-free production.

Description

technical field [0001] The invention relates to a preparation method of difenoconazole. Background technique [0002] Difenoconazole, chemical name: cis, trans-3-chloro-4-[4-methyl-2-1H-1,2,4-triazol-1-ylmethyl]-1, 3-Dipentan-2-yl)phenyl 4-chlorophenyl ether (cis, trans ratio is about 45:55); melting point: 78.6°C; vapor pressure: (20°C): 120nPa; solubility (25°C) : Water 15mg / L, easily soluble in organic solvents, ethanol 330g / L, acetone 610g / L, toluene 490g / L. [0003] Difenoconazole is a broad-spectrum triazole fungicide with the characteristics of high efficiency, safety, and low toxicity. It is widely used in the world for seed treatment and foliar spraying of food crops and economic crops to control fungal diseases. Because of its high efficiency, low toxicity, high chemical stability, and broad-spectrum sterilization, it has become a star product that domestic and foreign pesticide manufacturers are vying to develop. [0004] There are many manufacturers of difenoc...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06
Inventor 何永利陶亚春陶伟钱海滨
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products