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Synthesis method of high-content 2, 2-dichloro-1-(1-chlorocyclopropyl) ethanone for quantitative and qualitative analysis

The technology of chlorocyclopropyl ethyl ketone and cyclopropyl ethyl ketone is applied in the field of synthesis of high-content 2,2-dichloro-1-ethyl ketone, so as to reduce the impact of environmental pollution and human health, and achieve high purity. , the effect of improving quality

Active Publication Date: 2021-10-19
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Prothioconazole currently has four main production and synthesis routes. Although it is a low-toxic and pollution-free pesticide, one or more of many toxic and harmful reagents and solvents will be used in the production process depending on the synthesis route and production process. species, and may also produce many types of impurities

Method used

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  • Synthesis method of high-content 2, 2-dichloro-1-(1-chlorocyclopropyl) ethanone for quantitative and qualitative analysis
  • Synthesis method of high-content 2, 2-dichloro-1-(1-chlorocyclopropyl) ethanone for quantitative and qualitative analysis
  • Synthesis method of high-content 2, 2-dichloro-1-(1-chlorocyclopropyl) ethanone for quantitative and qualitative analysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone:

[0026]

[0027] Add 1-(1-chlorocyclopropyl)ethanone (59.3g, 0.50mol), methanol (MeOH) 30mL and dichloromethane (DCM) 180mL in a reaction flask equipped with a thermometer, magnetic stirring and acid tail gas absorption device , Chlorine gas (177.3g, 2.50mol) was introduced under stirring at 10-20°C, and the introduction was completed after 18 hours, and then the reaction was continued for 6 hours to end the reaction. Slowly add purified water to the reaction system under cooling and stirring in an ice bath, separate the liquids, wash the organic phase with saturated sodium bicarbonate solution and water respectively, dry with molecular sieves, and evaporate the solvent dichloromethane and methanol after heating and atmospheric pressure. 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone was distilled under pressure conditions of 120°C, 50mmHg).

[0028] The obtained product is a colorless liquid, weight: 74.5 g;...

Embodiment 2

[0030] Synthesis of 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone

[0031]

[0032] Add 1-(1-chlorocyclopropyl)ethanone (118.6g, 1.0mol), methanol (60mL) and dichloromethane (360mL) in a reaction flask equipped with a thermometer, mechanical stirring and acid tail gas absorption device, Sulfonyl chloride (539.8 g, 4.0 mol) was added dropwise under stirring at 0-10°C, and the addition was completed after 12 hours, and the temperature was continued for 12 hours to terminate the reaction. Slowly add purified water to the reaction system under cooling and stirring in an ice bath, separate the liquids, wash the organic phase with saturated sodium bicarbonate solution and water respectively, dry over molecular sieves, and distill under reduced pressure (collect 118-123 ° C fractions under 45-50 mmHg pressure ) to give 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone.

[0033] The weight of the obtained product: 152.3g; the purity: 97.8%; the yield: 81.3%.

Embodiment 3

[0035] Synthesis of 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone

[0036]

[0037]Add 1-(1-chlorocyclopropyl)ethanone (59.3g, 0.50mol) and dichloroethane (1200mL) into a reaction flask equipped with a thermometer, magnetic stirring and acid tail gas absorption device, Phosgene (296.7 g, 3.00 mol) was introduced under stirring, and the introduction was completed after 18 hours, and the temperature was continued for 12 hours to end the reaction. Slowly add purified water to the reaction system under cooling and stirring in an ice bath, separate the liquids, wash the organic phase with saturated sodium bicarbonate solution and water respectively, dry over molecular sieves, and distill under reduced pressure (collect 118-123 ° C fractions under 45-50 mmHg pressure ) to give 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone.

[0038] The weight of the obtained product: 73.2g; the purity: 97.4%; the yield: 78.1%.

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Abstract

The invention belongs to the technical field of pesticide synthesis, and particularly relates to a synthesis method of high-content 2, 2-dichloro-1-(1-chlorocyclopropyl) ethanone for quantitative and qualitative analysis. According to the method, cyclopropylethanone or chlorinated cyclopropylethanone used as a raw material is chlorinated to obtain the target compound, which can be used for analyzing the impurities of a prothioconazole bulk drug, tracking the sources of the impurities, researching the generation mechanism of the impurities, speculating the properties of the impurities according to the structures so as to control generation of the impurities or find a method for removing the impurities, and finally further improving the quality of the prothioconazole bulk drug and reducing the influence of potential impurities caused by the use of the pesticide prothioconazole on environmental pollution and human body health.

Description

technical field [0001] The invention belongs to the technical field of pesticide synthesis, in particular to a method for synthesizing high-content 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone for quantitative and qualitative analysis. Background technique [0002] [0003] Prothioconazole chemical name: (R,S)-2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1H-1,2, 4-Triazole-3(2H)-thione, CAS accession number: 178928-70-6, common name: Prothioconazole. The pure product is white crystal to light gray-brown crystalline powder, with a melting point of 139°C to 145°C. [0004] Prothioconazole is a new type of broad-spectrum triazolethione fungicide developed by Bayer. It is mainly used to prevent and control many diseases of cereals, wheat, and bean crops. Mutant, non-toxic to embryos, safe to humans and the environment. Its mechanism of action is to inhibit the demethylation at the 14th position of lanosterol or 2,4-methylenedihydrolanosterol, the precurso...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/63C07C49/327
CPCC07C45/63C07C2601/02C07C49/327
Inventor 孙传厚贾秋月李珂王祥传成道泉李洪侠李金鸿崔敏
Owner JINGBO AGROCHEM TECH CO LTD
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