Preparation method of tebuconazole

A technology of tebuconazole and pentene, which is applied in the field of preparation of tebuconazole, can solve the problems of low product content, low reaction yield, large amount of sewage and the like, achieves good selectivity and reduces isomer by-products. The effect of generating and reducing by-products

Active Publication Date: 2013-12-11
SHANGYU NUTRICHEM +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method high temperature synthesis, solvent purification method has a large

Method used

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  • Preparation method of tebuconazole
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  • Preparation method of tebuconazole

Examples

Experimental program
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Effect test

Embodiment 1

[0052] Synthesis of 4,4-dimethyl-1-(4-chlorophenyl)-1-penten-3-one: put 140ml methanol and 28.0g p-chlorobenzaldehyde (melted) into a 500ml four-neck flask, put 22.0g of pinacolone, 12.0g of sodium hydroxide, start stirring after the injection, slowly raise the temperature to 70°C and reflux, keep it for 5h, after the reaction, slowly cool down to 0±2°C, keep it for 0.5h, filter to get 43.5g of 4,4-di Methyl-1-(4-chlorophenyl)-1-penten-3-one, yield 97.6%.

Embodiment 2

[0054] Synthesis of 4,4-dimethyl-1-(4-chlorophenyl)-3-pentanone: 4,4-dimethyl-1-(4-chlorophenyl)-1 obtained in Example 1 -Penten-3-one 43.5 into the hydrogenation tank, while adding methanol 230ml, red aluminum solution 20.0g (red aluminum solution consists of 70% dihydrobis-(2 methoxyethoxy) sodium aluminate and 30% Composition of toluene, purchased from Nanjing Zhongheng Chemical Materials Co., Ltd., trade name: red aluminum), followed by nitrogen replacement three times, hydrogen replacement three times, slowly heating up, and at the same time starting to pass hydrogen reaction, control the temperature of the kettle at 30-67 °C, and the pressure <1.0Mpa. In the later stage, the temperature is controlled at 62-67°C, and the pressure is 0.7-0.9Mpa to react. When the pressure of the kettle remains basically unchanged, samples are taken for HPLC analysis. After passing the test, cool down to 35°C, let go to remove the methanol, first release the solvent under normal pressure ...

Embodiment 3

[0055] Embodiment 3 (comparative example 1)

[0056] Synthesis of 4,4-dimethyl-1-(4-chlorophenyl)-3-pentanone: 4,4-dimethyl-1-(4-chlorophenyl)-1 obtained in Example 1 - 43.5g of penten-3-one was put into the hydrogenation kettle, and 230ml of methanol was added at the same time, and 8.1g of Raney nickel was added at the same time, followed by three replacements with nitrogen, three replacements with hydrogen, and slowly raising the temperature. Temperature 10-67 ℃, pressure < 1.5Mpa. In the later stage, the temperature is controlled at 62-67°C, and the pressure is 1.2-1.5Mpa to react. When the pressure of the kettle remains basically unchanged, samples are taken for HPLC analysis. After passing the test, cool down to 35°C, vent to remove methanol, first remove methanol at 80°C under normal pressure, keep warm for 0.5h, then change to negative pressure precipitation (-0.095Mpa), heat up to 110°C and keep warm for 1h, until the methanol removal is qualified, 41.3g of yellow is ...

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Abstract

The invention discloses a preparation method of tebuconazole. The preparation method using p-chlorobenzaldehyde and pinacolone as initial raw materials comprises the following steps of: obtaining 2-(4-chlorobenzene ethyl)-2-tertiary butyl ethylene oxide through condensation reaction, hydrogenation reaction and epoxidation reaction in sequence; obtaining tebuconazole through ring-opening reaction of 2-(4-chlorobenzene ethyl)-2-tertiary butyl ethylene oxide and triazole under the co-catalysis of organic amine and crown ether. A catalysis technology of a composite catalyst which is composed of organic amine and crown ether is adopted, so that the isomer byproducts in the ring-opening reaction are greatly reduced, the ring-opening yield is improved to 92.8% from 80% of the conventional process, the product quality is improved to 98.5% or higher from 95%, and the total yield (in terms of p-chlorobenzaldehyde) is improved to 82% or higher from 65% of the conventional process.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of tebuconazole. Background technique [0002] Tebuconazole, the chemical name is (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)penta- 3-alcohol, the structure of which is shown in formula (I). Tebuconazole is a high-efficiency, broad-spectrum, systemic triazole fungicidal pesticide, which has three functions of protection, treatment and eradication, and has a wide bactericidal spectrum and long-lasting effect. long. [0003] [0004] There are many studies on the synthesis of tebuconazole, most of which use p-chloroformaldehyde as the starting material to prepare tebuconazole through the steps of aldehyde-ketone condensation, catalytic hydrogenation, epoxidation reaction and ring-opening reaction. Tan Chengxia and others reported the synthesis of the fungicide tebuconazole by using p-chlorobenzaldehyde and pinacolone as...

Claims

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Application Information

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IPC IPC(8): C07D249/08
Inventor 冯应江王满陈国斌梁俊芳游华南温沛宏王红福李伯文王文军陈均坤陈佳易
Owner SHANGYU NUTRICHEM
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