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Preparation method of halogenation cycloolefin

A technology of halogenated cycloalkenes and halogenated cycloalkanes, which is applied in the field of preparation of halogenated cycloalkenes, can solve the problems of waste solids such as a large amount of metal halides, pollute the environment, and low yield, and achieve high yield and safe process Reliable results with mild reaction conditions

Active Publication Date: 2019-07-12
泉州宇极新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the above-mentioned existing technology, the synthesis of perhalocyclopentene represented by hexafluorocyclobutene has the following defects: (1) when the reducing agent is metal powder, a large amount of waste solids such as metal halides will be produced, causing serious pollution environment; (2) when the reducing agent is hydrogen, because of the generation of by-product saturated naphthenes, the yield is very low

Method used

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  • Preparation method of halogenation cycloolefin
  • Preparation method of halogenation cycloolefin
  • Preparation method of halogenation cycloolefin

Examples

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Embodiment 1

[0055] In a 1L autoclave, add 2 mol of N,N-dimethylformamide and 1 mol of 1,2-dichlorohexafluorocyclobutane (the molar ratio of cis and trans is 60:40), at 160 The reaction was carried out for 6 hours. After the reaction was finished, rectification was carried out to obtain hexafluorocyclobutene (boiling point was 5-6°C / 760mmHg), the yield was 96.8%, and the purity was 99.1%.

Embodiment 2

[0057] In a 1L autoclave, add 2 mol of N,N-dimethylacetamide and 1 mol of 1,2-dichlorohexafluorocyclobutane (the molar ratio of cis and trans is 60:40), at 170 The reaction was carried out for 6 hours. After the reaction was finished, rectification was carried out to obtain hexafluorocyclobutene (boiling point was 5-6°C / 760mmHg), the yield was 95.8%, and the purity was 99.2%.

Embodiment 3

[0059] In a 1L autoclave, add 1 mol of N,N-dimethylformamide and 1 mol of 1,1,2-trichloro-2,3,3-trifluorocyclobutane, and react at 160 degrees for 6 hours, After the reaction, rectification was carried out to obtain 1-chloro-2,3,3-trifluorocyclobutene (boiling point: 51-52°C / 760mmHg), with a yield of 80.5% and a purity of 98.4%.

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Abstract

The invention relates to a preparation method of halogenation cycloolefin and belongs to the field of chemical synthesis. According to the preparation method, in an amide or alkylamine solvent, with halogenation cycloparaffin as a raw material, a dehalogenation reaction is conducted, and the target product halogenation cycloolefin is obtained. According to the method, the reaction conditions are mild, the yield of the halogenation cycloolefin is high, dangerous reduction agents such as metal or hydrogen do not need to be used, the technology is safe and reliable, solid waste such as metal halide is not generated, and a common distillation means can be used for effective industrial separation.

Description

technical field [0001] The present invention relates to a method for preparing halogenated cycloalkenes, in particular to a method for synthesizing halogenated cycloalkenes through a highly selective dehalogenation reaction of halogenated cycloalkanes under the condition that no metal or hydrogen exists and only the presence of amides is required. . Background technique [0002] Dehalogenation reaction is an important method for the synthesis of halogenated alkenes. The traditional method generally adopted is to use metal or hydrogen as a reducing agent to reduce organic raw materials to synthesize halogenated cycloalkenes. [0003] US Patent No. 2436142 reports that in ethanol solvent, 1,2-dichlorohexafluorocyclobutane reacts with zinc powder under reflux conditions to obtain hexafluorocyclobutene with a yield of 94%. [0004] The document "Russian Journal of Organic Chemistry, 2010, vol.46, 1290–1295" reported that at 180°C, hydrogen reacted with 1,2-dichlorohexafluorocy...

Claims

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Application Information

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IPC IPC(8): C07C17/25C07C23/06C07C23/10
CPCC07C17/25C07C2601/04C07C2601/16C07C23/06C07C23/10
Inventor 张呈平张文妮郭勤权恒道
Owner 泉州宇极新材料科技有限公司
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