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Preparation method of hexafluorobutadiene

A technology of hexafluorobutadiene and trifluoroethylene bromide is applied in the preparation of halogenated hydrocarbons, chemical instruments and methods, zinc organic compounds, etc. Simple preparation process, high selectivity effect

Active Publication Date: 2020-05-22
ELECTRIC POWER RES INST OF GUANGDONG POWER GRID
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of this, the application discloses a preparation method of hexafluorobutadiene, which can effectively solve the existing synthetic method of the current method for preparing hexafluorobutadiene Complex, waste-prone technical flaws

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The embodiment of the present application provides the first preparation method of hexafluorobutadiene, the specific steps are as follows:

[0028] In a 250ml three-necked flask, under nitrogen atmosphere, add 15g of zinc powder, 45g of N-methylpyrrolidone, 0.2g of aluminum trichloride, heat to 70°C, add dropwise 26g of 1,1-dibromotetrafluoroethane solution, drop Adding time is 1.2h, adjust the rate of addition, and keep the reaction temperature below 90°C. After the dropwise addition, the reaction was maintained at 88°C for 2.0h, and then lowered to room temperature. Then add 0.8 g of tetrakis(triphenylphosphine) palladium, and feed 16 g of bromotrifluoroethylene for 1.6 h. Control the feed rate so that the reaction temperature does not exceed 40° C. After the dropwise addition, react at 40° C. for 20 h. After the generated gas was condensed in a -35°C cold trap, it was collected with liquid nitrogen as a cold trap, and about 13.9 g of liquid was actually collected, o...

Embodiment 2

[0030] The embodiment of the present application provides the second preparation method of hexafluorobutadiene, the specific steps are as follows:

[0031] In a 250ml three-necked flask, under nitrogen atmosphere, add 31g of zinc powder, 30g of acetonitrile, 0.28g of aluminum tribromide, heat to 50°C, add 26g of 1,1-dibromotetrafluoroethane solution dropwise, and the dropping time is 1.5 h, adjust the rate of addition, and keep the reaction temperature below 75°C. After the dropwise addition, the reaction was maintained at 80°C for 4.0h, and then lowered to room temperature. Then add 0.5 g of tetrakis(triphenylphosphine)palladium, and introduce 15.6 g of bromotrifluoroethylene, and control the rate of gas introduction so that the reaction temperature does not exceed 40°C. After the dropwise addition, react at 40°C for 15 hours. After the generated gas was condensed at -30°C, it was collected with liquid nitrogen as a cold trap, and about 11.3 g of liquid was actually collecte...

Embodiment 3

[0033] The embodiment of the present application provides the third preparation method of hexafluorobutadiene, the specific steps are as follows:

[0034] In a 250ml three-neck flask, under nitrogen atmosphere, add 23g of zinc powder, 35g of DMF, 0.12g of aluminum trichloride, heat to 80°C, add 26g of 1,1-dibromotetrafluoroethane solution dropwise, and the dropping time is 2.0h , adjust the rate of addition, and keep the reaction temperature below 100°C. After the dropwise addition, the reaction was maintained at 100°C for 2.5h, and then lowered to room temperature. Then add tetrakis(triphenylphosphine)palladium 0.65g, pass through trifluoroethylene bromide 15.6g, control the speed so that the reaction temperature does not exceed 25°C, after the dropwise addition, react at 55°C for 18h. After the generated gas was condensed at -30°C, it was collected with liquid nitrogen as a cold trap, and about 13 g of liquid was actually collected, of which the content of hexafluorobutadie...

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Abstract

The invention belongs to the technical field of organic chemistry, particularly relates to a preparation method of hexafluorobutadiene, and provides a preparation method of hexafluorobutadiene. The method comprises the following steps: in an inert atmosphere, carrying out a reaction on 1,1-dibromotetrafluoroethane as a raw material and zinc powder in an aprotic polar solvent in the presence of aluminum trihalide to generate an organic zinc reagent; and then reacting with trifluorobromoethylene under the action of a palladium catalyst to generate hexafluorobutadiene. The invention discloses a preparation method of hexafluorobutadiene, wherein the preparation method can effectively overcome the technical defects of complex synthesis method and high waste generation tendency in the existing hexafluorobutadiene preparation method.

Description

technical field [0001] The application belongs to the technical field of organic chemistry, and in particular relates to a preparation method of hexafluorobutadiene. Background technique [0002] Hexafluorobutadiene is a liquefied gas with the molecular formula C 4 f 6 , molecular weight 162, melting point -132°C, boiling point 6°C, critical temperature 140°C, gas phase density (relative to air) 6.79, combustion range 7%-73%. In recent years, C 4 f 6 The market demand for etching processes in the semiconductor industry continues to grow. Hexafluorobutadiene can be used as an excellent dry etching gas. C 4 f 6 There are many synthetic methods. [0003] Patent JP 2001114710 reported that the target product hexafluorobutadiene was produced through bromination, isomerization and coupling reactions of tetrafluoroethylene, with a purity of about 84% and a yield of about 47%. Burton et al. (Tetrahedron Lett.43 (2002) 2731-2733) reported that using HFC-134a as a raw materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/263C07C21/20
CPCC07C17/263C07F3/06C07C21/20
Inventor 周永言唐念李丽樊小鹏邹庄磊孙东伟
Owner ELECTRIC POWER RES INST OF GUANGDONG POWER GRID