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Method for preparing hydrogen halide cycloolefin by hydrolyzing halogenated cycloolefin

A technology for hydrohalogenated cyclic olefins and halogenated cyclic olefins, which is used in dehalogenation preparation, organic chemistry, etc., can solve the problems of high reaction temperature, low selectivity, and pollute the environment, and achieves safe and reliable process, mild reaction conditions, and post-processing Handling easy effects

Pending Publication Date: 2020-07-17
泉州宇极新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above existing processes have the following defects: (1) In the gas-phase catalytic hydrodechlorination method, hydrogen is used as the hydrogen source, and hydrogen is a flammable and explosive dangerous product, and its transportation, storage and use all have great dangers ; The reaction temperature is higher, up to 360 degrees Celsius; In addition, the selectivity of the hydrohalocyclopentene that only replaces one hydrogen is lower, generally less than 10%, and it is easier to undergo deep hydrogenation of the C=C double bond to obtain saturated cycloalkane; ( 2) In the hydrogen-chlorine exchange method in which the amide provides the hydrogen source, the complex formed by the metal, the amide and the halogen element sticks to the inner wall of the reactor in the state of asphalt, and it is easy to embed zinc powder during the reaction process, which not only greatly The yield of the target product is reduced, and it is difficult to clean up and recycle in the post-treatment process, resulting in a large amount of waste solid, waste liquid and toxic waste gas, which will seriously pollute the environment

Method used

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  • Method for preparing hydrogen halide cycloolefin by hydrolyzing halogenated cycloolefin
  • Method for preparing hydrogen halide cycloolefin by hydrolyzing halogenated cycloolefin
  • Method for preparing hydrogen halide cycloolefin by hydrolyzing halogenated cycloolefin

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Add zinc powder, water, N,N-dimethylacetamide, and 1,2-dichlorohexafluorocyclopentene to a 200-mL glass flask equipped with a condenser and a balloon-sealed condenser outlet under stirring conditions , the molar ratio of zinc powder / water / N,N-dimethylacetamide / 1,2-dichlorohexafluorocyclopentene is 1.25 / 1 / 5 / 1, zinc powder is 0.25 moles, water is 0.2 moles, N , N-dimethylacetamide is 1 mole, 1,2-dichlorohexafluorocyclopentene is 0.2 mole, the reaction temperature is 80° C., and the reaction time is 6 hours. After reaction finishes, cool to room temperature, wash with 200 milliliters of water, filter to remove solid, filtrate is carried out normal pressure distillation, obtains 1-chloro-3,3,4,4,5,5-hexafluorocyclopentene (boiling point is 72-73°C / 760mmHg), the yield is 97.5%, and the purity is 99.6%.

Embodiment 2

[0042] Add zinc powder, water, N,N-dimethylacetamide, and 1,2-dichlorohexafluorocyclopentene to a 200-mL glass flask equipped with a condenser and a balloon-sealed condenser outlet under stirring conditions , the molar ratio of zinc powder / water / N,N-dimethylacetamide / 1,2-dichlorohexafluorocyclopentene is 1 / 1 / 5 / 1, zinc powder is 0.2 moles, water is 0.2 moles, N , N-dimethylacetamide is 1 mole, 1,2-dichlorohexafluorocyclopentene is 0.2 mole, the reaction temperature is 80° C., and the reaction time is 6 hours. After reaction finishes, cool to room temperature, wash with 200 milliliters of water, filter to remove solid, filtrate is carried out normal pressure distillation, obtains 1-chloro-3,3,4,4,5,5-hexafluorocyclopentene (boiling point is 72-73°C / 760mmHg), the yield is 88.0%, and the purity is 99.8%.

Embodiment 3

[0044] Add zinc powder, water, N,N-dimethylacetamide, and 1,2-dichlorohexafluorocyclopentene to a 200-mL glass flask equipped with a condenser and a balloon-sealed condenser outlet under stirring conditions , the molar ratio of zinc powder / water / N,N-dimethylacetamide / 1,2-dichlorohexafluorocyclopentene is 1 / 2.78 / 4.86 / 1, zinc powder is 0.2 moles, water is 0.556 moles, N , N-dimethylacetamide is 0.972 mol, 1,2-dichlorohexafluorocyclopentene is 0.2 mol, the reaction temperature is 80° C., and the reaction time is 6 hours. After reaction finishes, cool to room temperature, wash with 200 milliliters of water, filter to remove solid, filtrate is carried out normal pressure distillation, obtains 1-chloro-3,3,4,4,5,5-hexafluorocyclopentene (boiling point is 72-73°C / 760mmHg), the yield is 86.5%, and the purity is 99.7%.

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Abstract

The invention relates to a method for preparing hydrogen halide cycloolefin by hydrolyzing halogenated cycloolefin, and belongs to the field of chemical synthesis. According to the method, in an aprotic polar solvent capable of being mixed and dissolved with water, zinc powder induces halogenated cycloolefin shown as a formula (I) to be subjected to a hydrolysis reaction with water to obtain hydrohalogenated cycloolefin shown as a formula (II) and a formula (III), and the reaction temperature is 50-180 DEG C. The method has the advantages of mild reaction conditions, high halocycloolefin selectivity, simple and environment-friendly post-treatment, and realization of effective separation through a common distillation means in industry.

Description

technical field [0001] The present invention relates to a method for hydrolyzing halogenated cycloalkenes to prepare hydrogen halogenated cycloalkenes, in particular to a method for hydrolyzing halogenated cycloalkenes and water to synthesize hydrogen in the presence of zinc powder, using an aprotic polar solvent as a solvent and a catalyst Halocycloalkene method. Background technique [0002] Hydrohalocycloolefins are an important class of fluorine-containing building blocks. There are two common synthesis methods at present: [0003] The first is gas-phase catalytic hydrodechlorination. JP3876951B reported the hydrodechlorination reaction of 1,2-dichlorohexafluorocyclopentene with hydrogen. At 360°C, in the presence of Ni catalyst, H 2 Flow rate is 440mL / min, the flow rate of 1,2-dichlorohexafluorocyclopentene is 0.4g / h, then the transformation rate of 1,2-dichlorohexafluorocyclopentene is 98.8%, and 1-chloro-3 , The selectivity of 3,4,4,5,5-hexafluorocyclopentene is v...

Claims

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Application Information

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IPC IPC(8): C07C23/08C07C17/23C07C23/06C07C23/10
CPCC07C17/23C07C2601/04C07C2601/10C07C2601/16
Inventor 张呈平张文妮贾晓卿权恒道
Owner 泉州宇极新材料科技有限公司
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