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Synthesis method of 2-chloro-1-(1-chlorocyclopropyl) ethanone

A technology of chlorocyclopropyl group and a synthesis method, applied in the synthesis field of 2-chloro-1-ethanone, can solve the problems of poor selectivity, low yield, difficult control of impurities, etc., and achieves improved yield and less corrosiveness of equipment , improve the effect of selectivity

Active Publication Date: 2022-04-08
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although chlorine gas does not produce sulfur dioxide gas as a chlorination reagent, chlorine gas still has problems such as poor selectivity, low yield, and difficult control of methyl position dichlorination and trichlorination impurities.

Method used

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  • Synthesis method of 2-chloro-1-(1-chlorocyclopropyl) ethanone
  • Synthesis method of 2-chloro-1-(1-chlorocyclopropyl) ethanone
  • Synthesis method of 2-chloro-1-(1-chlorocyclopropyl) ethanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 100g of dichloroethane and (200g, 2.378mol) cyclopropylmethyl ketone into a 500mL four-neck flask, cool down to -5°C, and add (1.34g, 11.8mmol) MeAlCl under stirring 2 , Feed chlorine gas, feed rate is about 25g / h, tail gas water carries out three-stage absorption, ventilates 14.0h, gas chromatography detects product relative content 2-chloro-1-(1-chlorocyclopropyl) ethyl ketone 4.2%, 2-Chloro-1-(1-chlorocyclopropyl)ethanone 93.8%, 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone 1.8%, slowly heated to 30°C under reduced pressure Remove solvent. Under -0.1MPa vacuum, use a 50cm rectification column and a glass ring packing to carry out rectification reaction, slowly raise the temperature to 130°C, collect the fraction at 100-102°C to obtain 2-chloro-1-(1-chlorocyclopropyl) Ethanone, 82.5~82.6°C, the previous fraction was applied back to the reaction to obtain 341.7 g of the product 2-chloro-1-(1-chlorocyclopropyl)ethanone, with a content of 97% and a yield of 91.0%.

...

Embodiment 2

[0031] Add (200g, 2.378mol) cyclopropylmethyl ketone into a 500ml four-necked flask, cool down to 10°C, add 150g dichloroethane, and add (4.4g, 47.6mmol) Me 2 AlCl, feed chlorine gas, the feed rate is about 60g / h, tail gas is absorbed by water for tertiary absorption, reacted for 6.5h, and the relative content of the product detected by gas chromatography is 5.4% of 2-chloro-1-(1-chlorocyclopropyl)ethanone , 2-chloro-1-(1-chlorocyclopropyl)ethanone 93.5%, 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone 0.9%, slowly warming up to 30°C under reduced pressure Solvent was removed. Under -0.1MPa vacuum, use a 50cm rectification column and a glass ring packing to carry out rectification, slowly raise the temperature to 130°C, collect fractions at 99.6~102°C, and obtain 2-chloro-1-(1-chlorocyclopropyl) Ethyl ketone, 82.5-82.7 ° C front fraction was applied back to the reaction to obtain 339.6 g of the product, the content was 96%, and the yield was 89.6%.

Embodiment 3

[0033] Add (200g, 2.378mol) cyclopropylmethyl ketone into a 1000ml four-necked flask, cool down to 15°C, add 200g of dichloromethane, and add (8.95g, 95mmol) MeAlCl under stirring condition 2 and (3.67g, 39.6mmol) Me 2 AlCl, feed chlorine gas, feed rate is about 75g / h, tail gas water carries out tertiary absorption, reacts 3.5h, gas chromatography detects product 2-chloro-1-(1-chlorocyclopropyl) ethyl ketone 2.4%, 2 -Chloro-1-(1-chlorocyclopropyl)ethanone 95.2%, 2,2-dichloro-1-(1-chlorocyclopropyl)ethanone 2.1%, the reaction is completed and the temperature is slowly raised to 30°C under reduced pressure Remove dichloromethane, under -0.1MPa vacuum, use 50cm rectification column, glass ring packing to carry out rectification, slowly heat up to 130°C, collect fractions at 100-102°C to obtain 2-chloro-1-(1 -Chlorocyclopropyl)ethanone, 82.4~82.8°C front fraction was applied back to the reaction to obtain 343.4g of product, the content was 96%, and the yield was 90.6%.

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Abstract

The invention discloses a synthesis method of 2-chloro-1-(1-chlorocyclopropyl) ethanone, which comprises the following steps: S1, taking cyclopropyl methyl ketone IV as a raw material, dissolving by adopting a solvent, adding a compound containing metal aluminum as a catalyst, and introducing chlorine to carry out chlorination reaction to obtain chlorinated products: 2-chloro-1-(1-chlorocyclopropyl) ethanone I, 1-(1-chlorocyclopropyl) ethanone II and 2, 2-dichloro-1-(1-chlorocyclopropyl) ethanone II; 2, 2-dichloro-1-(1-chloro cyclopropyl) ethanone III is added into the reaction kettle; and S2, carrying out reduced pressure distillation on the chlorinated product to remove the solvent, and rectifying to obtain the 2-chloro-1-(1-chlorocyclopropyl) ethanone. The method is simple to operate, meets the green and environment-friendly requirements, is relatively high in yield and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a synthesis method of 2-chloro-1-(1-chlorocyclopropyl)ethanone, which belongs to the technical field of chemical synthesis. Background technique [0002] Prothioconazole is a new broad-spectrum triazolethione fungicide developed and created by Bayer, and 2-chloro-1-(1-chlorocyclopropyl)ethanone is an important intermediate for the synthesis of prothioconazole , but in the prior art, its synthesis technology is less, and the synthesis yield is low, the purity is not high, and the product contains various impurities, resulting in a low degree of industrialization. [0003] For example, most processes in the prior art use 1-(1-chlorocyclopropyl)ethanone as a raw material, and at low temperature, sulfonyl chloride is used as a chlorination reagent to synthesize, and the conversion rate of chlorinated products is low, and dichlorinated and trichlorinated The impurities are higher, and the product yield is lower, only about 75%. An...

Claims

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Application Information

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IPC IPC(8): C07C49/327C07C45/63B01J31/14
CPCY02P20/584
Inventor 赵娜张耀林田学芳侯红欣李志峰赵建芹贾成国
Owner HEBEI VEYONG BIO CHEM
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