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Hexythiazox and preparation method thereof

A technology of hexythifen and ketoxime is applied in the field of hexythifen and its preparation, and achieves the effects of improving reaction yield, good permeability and remarkable effect

Inactive Publication Date: 2017-05-10
WENZHOU UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In view of the above problems, the present invention provides a hexythiazox and its preparation method, which is suitable for industrial production, can simplify the process flow, increase the reaction yield, reduce the difficulty of synthesis, reduce the formation of by-products, and reduce the environmental pollution problem in the preparation process. and reduce production costs

Method used

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  • Hexythiazox and preparation method thereof
  • Hexythiazox and preparation method thereof
  • Hexythiazox and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0042] A preparation method of hexythiazox, comprising the following steps:

[0043] Step S1, ketoximation reaction

[0044] The reaction equation is:

[0045]

[0046] Raw materials: p-chloropropiophenone, purity 99%; n-butyl nitrite, purity 99%; petroleum ether, temperature 90°C-120°C;

[0047] Operation: Put 350Kg p-chloropropiophenone and 700Kg petroleum ether into a 3000-liter reactor, cool down to 10°C, then add 235Kg n-butyl nitrite, stir for 5 hours, then cool down to 0°C, keep stirring for 0.5h, and discharge , filtered, washed with petroleum ether, and dried to obtain a solid ketoxime;

[0048] Step S2, alcohol amination reaction

[0049] The reaction equation is:

[0050]

[0051] Raw materials: ketoxime, purity 99%; methanol, purity 99.5%; hydrochloric acid, purity 30%; ethanol, purity 99.5%;

[0052] Operation: Put 180Kg of the prepared ketoxime and 480Kg of methanol into a 2000-liter reactor, add 1Kg of catalyst platinum, dissolve for 0.5h, replace wit...

Embodiment 2

[0069] A preparation method of hexythiazox, comprising the following steps:

[0070] Step S1, put 174Kg p-chloropropiophenone and 350Kg petroleum ether into a 3000-liter reactor, cool down to 20°C, then add 117.5Kg n-butyl nitrite, stir for 10h, then cool down to 0°C, keep stirring for 1.5h, Blowing, filtering, washing with petroleum ether, and drying to obtain solid ketoxime;

[0071] Step S2, put 90Kg of the prepared ketoxime and 240Kg of methanol into a 2000-liter reactor, add 1Kg of catalyst palladium, dissolve for 0.5h, replace 4 times with nitrogen, then replace 4 times with hydrogen, heat up to 40°C, and pass in hydrogen, Control the hydrogen pressure to 0.08Mpa until no more hydrogen can be added. After the hydrogen flow is completed, the catalyst palladium is removed by filtration while it is hot to obtain a methanol solution of the alcohol amine. The pH value is adjusted to 6.5 with hydrochloric acid, and the solvent is removed under reduced pressure to obtain the al...

Embodiment 3

[0076] A preparation method of hexythiazox, comprising the following steps:

[0077] Step S1, put 420Kg of p-chloropropiophenone and 840Kg of petroleum ether into a 3000-liter reactor, cool down to 15°C, then add 282Kg of n-butyl nitrite, stir for 7.5h, then cool down to 0°C, keep stirring for 1h, and let it cool down to 15°C. material, filtered, washed with petroleum ether, and dried to obtain a solid ketoxime;

[0078] Step S2, put 216Kg of the prepared ketoxime and 576Kg of methanol into a 2000-liter reactor, add 1.8Kg of catalyst nickel, dissolve for 0.5h, replace with nitrogen 3 times, then replace with hydrogen 3 times, heat up to 37°C, and pass in hydrogen , control the hydrogen pressure to 0.05Mpa, until no more hydrogen is added, the hydrogen flow is completed, the catalyst nickel is removed by filtration while it is hot, and the methanol solution of the alcohol amine is obtained, the pH value is adjusted to 6.3 with hydrochloric acid, and the solvent is removed under...

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Abstract

The invention discloses hexythiazox and a preparation method thereof. The method includes: taking chloropropiophenone as a starting material to react with n-butyl nitrite in a mass ratio of 70:47 to generate ketoxime; performing hydrogenation reduction to obtain 2-amino-1-p-chlorophenyl propanol hydrochloride; directly subjecting 2-amino-1-p-chlorophenyl propanol hydrochloride to reaction with carbon disulfide to synthesize trans-5-(4-chlorphenyl)-4-methyl-2-sulfo-thiazolidone which is then oxidized through hydrogen peroxide to generate 5-(4-chlorphenyl)-4-methyl-2-oxo-thiazolidone; subjecting 5-(4-chlorphenyl)-4-methyl-2-oxo-thiazolidone to additive reaction with cyclohexyl isocyanate to obtain hexythiazox which is a final product. The preparation method is suitable for industrial production, a technical process is simplified, reaction yield is increased, synthesis difficulty is lowered, by-products are reduced, the problem of environment pollution in a preparation process is reduced, and production cost is reduced as well.

Description

technical field [0001] The invention relates to the field of insecticides, in particular to hexythiazox and a preparation method thereof. Background technique [0002] The country pays more and more attention to the development of pesticides. In terms of environmental protection, reducing the risks of pesticides to society and the environment has become a top priority. With the changes in the planting structure, the sales of insecticides (acaricides), one of the three major series of pesticides, have grown rapidly in recent years. Countries around the world have also increased their efforts in the development of pesticide technology, and new technologies and new products are constantly emerging. [0003] Hexythiazox, chemical name: (4RS,5RS)-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide . Its chemical structural formula is: [0004] [0005] This product was developed by Japan Soda Company in 1985, and its synthetic route is as follows: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/14
CPCC07D277/14
Inventor 陈帆陈共华潘光飞胡新根廖文斌王进李冬良陈华
Owner WENZHOU UNIVERSITY
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