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New method for producing propiconazole

The technology of a propiconazole and a new method is applied in a new field of production of the original propiconazole, can solve the problems of difficult recycling of mixed solvents, low bromination conversion rate, difficult nitration operation, etc., and achieves reduction of solvent treatment costs, The effect of shortening the reaction period and high bromide conversion rate

Active Publication Date: 2010-07-21
利民化学有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the low bromination conversion rate existing in the prior art, the bromination is difficult to carry out, the reaction time is long when the 1,2,4-triazole potassium salt is synthesized, the water generated by the reaction is difficult to remove, and the mixed solvent is difficult to handle and recycle. And nitration is not easy to operate and other shortcomings, the present invention provides a new production method of the original drug of propiconazole, so that the conversion rate of bromination is high, the solvent is single, easy to handle, recycle and apply mechanically, and the product is easy to purify

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0027] A new method for the production of the original drug of propiconazole, according to the ratio of the amount of substances 2,4-dichloroacetophenone: 1,2-pentanediol is a ratio of 1: 1.2, 2,4 dichloroacetophenone Ketone and 1,2-pentanediol undergo cyclization reaction under reflux, at this time the temperature is about 86°C, and the reaction time is about 10 hours. Then, after the cyclization reaction is completed, bromination reaction is carried out. First add bromine accounting for 1% to 10% of the total mass of bromine required for the reaction into the reaction system for bromination induction reaction. After 5 to 50 minutes of reaction, white smoke is generated in the kettle, which proves that the initiation is successful, and a large amount of bromine is started. Add the remaining bromine dropwise, and continue the reaction for 0.5 to 3.0 hours for bromination to generate bromide——2-bromomethyl-(2,4-dichlorophenyl)-4-propyl-1,3-dioxol alkyl. In the present inventio...

Embodiment 2

[0030] Add 210KG of 2,4-dichloroacetophenone to the reaction kettle, and react with 145KG of 1,2-pentanediol under the conditions of solvent cyclohexane 1800L and catalyst p-toluenesulfonic acid 10-20Kg, and continuously Separating the water to obtain a cyclohexane solution containing the cyclized product, when 2,4-dichloroacetophenone≤1.0% therein (liquid chromatography, L=150mm-250mm, T=40°C, wavelength 205nm~220nm , the mobile phase is a certain proportion of methanol and water mixed solvent), the temperature is lowered to 20-80° C., and the excess 1,2-pentanediol is separated by standing. After raising the temperature to 40°C, add 1% to 10% of the total amount of bromine required, that is, 2.1 to 21Kg, into the reaction kettle, and keep it warm for about 5 to 50 minutes at 20 to 80°C. White smoke is emitted from the kettle. Accurate, it proves that the bromination initiation is successful. At this time, the remaining bromine is added dropwise at 10-45°C, and the time is co...

Embodiment 3

[0045] Add 105KG (95%wt) of 1,2,4-triazole and 97KG (92%wt) of potassium hydroxide to the reaction kettle, under the condition of 600L pyrrolidone as solvent, 140~200℃ with intermittent slight negative pressure (- 0.02-0.08MPa) backflow to separate water, the reaction time is 4-5 hours, and the water content is controlled below 2.8%wt (measured by a micromoisture analyzer). To obtain 1,2,4-triazole potassium, add bromide 2-bromomethyl-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolane prepared in Example 2 (500L pyrrolidone washing kettle), react at 150℃~155℃ for about 5~7 hours, get the crude propiconazole, filter, evaporate pyrrolidone, add 1800L toluene and 500L water to wash, separate layers to remove water, evaporate toluene , Then enter the high vacuum distillation process distillation (see embodiment 4 for details), obtain propiconazole.

[0046] Table five

[0047] The results of five consecutive batches of reaction without micro-negative pressure dehydration

[0048] ...

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Abstract

The invention discloses a new method for producing propiconazole, comprising the following steps of: cyclizing 2,4-dichloroacetophenone and 1,2-pentanediol, brominating with bromine to generate 2-brooethyl-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolane, then condensing with 1,2,4-tolyltriazole sylvite to prepare a crude product, and desolventizing, washing and distilling the crude product in vacuum to obtain the propiconazole. When the brominating reaction is carried out after the cyclizing reaction is finished, the bromine is added for twice, firstly the bromine accounting for 1%-10% of the total weight of the bromine is added in a reaction system for brominating induction reaction, and then the residual bromine is added. The bromine is added for twice during brominating reaction, firstly the bromine accounting for 1%-10% of the total weight of the bromine is added for initiating the whole system, the brominating induction reaction guides the direction of the brominating reaction so that monobromides and dibromides generating ketone due to the repeated resolution of cyclized matter are reduced, and finally the method achieves the purpose of improving the yield of the brominating reaction; and the conversion rate of the bromides is high and can be greater than 97%.

Description

technical field [0001] The invention relates to a production method of triazole fungicides, in particular to a new production method of propiconazole original drug Background technique [0002] Propiconazole (propiconazole) is a kind of cyclobutanazole systemic fungicide developed by Switzerland Ciba-Geigy Corporation, the chemical name of propiconazole: cis-trans 1-[2-(2,4-dichloro Phenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole is a sterol demethylation preparation with broad spectrum and systemic properties . The appearance of the original drug is a light yellow sticky silk liquid, with a boiling point (13.3Pa) of 180°C, a vapor pressure (20°C) of 0.133mPa, a refractive index of 1.5468, and a specific gravity (20°C) of 1.27g / cm3. The solubility in water is 110mg / L, easily soluble in organic solvents. Stable below 320°C, relatively stable to light, and not obvious in hydrolysis. It is relatively stable in acidic and alkaline media and does not corrode metal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06
Inventor 孙敬权徐勤江唐启举许宜伟孙丽梅郑翠秀
Owner 利民化学有限责任公司
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