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Preparation method of hexafluoro-1,3-butadiene

A technology of butadiene and bromotrifluoroethylene, which is applied in the preparation of halogenated hydrocarbons, chemical instruments and methods, zinc organic compounds, etc., can solve the problems of high flushing temperature, decomposition of brominated trifluoroethylene zinc reagent, and large amount of three wastes, etc. question

Active Publication Date: 2017-05-17
ZHEJIANG RES INST OF CHEM IND CO LTD +2
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, the preparation method of hexafluoro-1,3-butadiene disclosed in Chinese patent CN101031529A first makes bromotrifluoroethylene react with zinc to generate trifluorovinyl zinc bromide reagent, and then reacts Fe, Cu, Na, Mg, Ni Or obtain hexafluoro-1,3-butadiene under the oxidation of the halide of Ag, the highest yield of embodiment report is only 68%, and product purity is only 93%, and needs the metal halide oxidizer of equivalent, causes three wastes amount to be relatively large Big
In this preparation method, an initiation process is required in the preparation stage of the trifluoroethylene zinc bromide reagent, and the temperature after initiation is relatively high, which will not only cause the decomposition of the trifluoroethylene zinc bromide reagent, but also have a higher safety risk

Method used

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  • Preparation method of hexafluoro-1,3-butadiene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: preparation of zinc reagent

[0031] Add N,N-dimethylformamide (600g, 8.2mol), zinc powder 85.0g (1.3mol), 1,2-dibromoethane 5.6g (0.03 mol), the temperature was lowered to 0°C with mechanical stirring, and 161 g (1.0 mol) of bromotrifluoroethylene was slowly introduced. After the reaction was initiated, the temperature was kept at 40°C until the bromotrifluoroethylene in the reaction solution was completely converted, and the stirring was stopped. After cooling down to room temperature, the The excess zinc powder is separated to obtain a zinc reagent solution. use 19 Quantification by FNMR (trifluorotoluene as internal standard), the reaction yield was 88.4%.

[0032] Zinc reagent and internal standard NMR fluorine spectrum data, 19 FNMR (CDCl 3 ,376MHz): δ-86.80(s, trifluorotoluene peak, 3F), -119.63(dd, J 1 =32Hz,J 2 =92Hz, 1F), -153.74(dd, J 1 =J 2 =32Hz, 1F), -217.99(dd, J 1 =32Hz,J 2 = 103Hz, 1F).

Embodiment 2

[0033] Embodiment 2: preparation of zinc reagent

[0034] Add 1,3-dimethyl-2-imidazolidinone (600g, 5.26mol), 84.5g (1.3mol) of zinc powder, 1,2-dibromoethane 5.64g (0.03mol), mechanically stirred and cooled down to 0°C, slowly passed into 161g (1.0mol) of bromotrifluoroethylene, and kept warm at 40°C after the reaction was triggered, until the bromotrifluoroethylene in the reaction solution was completely converted, stopped stirring, and dropped to 0°C. After reaching room temperature, the excess zinc powder was separated to obtain a zinc reagent solution. use 19 FNMR quantification (trifluorotoluene as internal standard), the reaction yield was 82.1%.

Embodiment 3

[0035] Embodiment 3: preparation of zinc reagent

[0036]Add N,N-dimethylacetamide (600g, 6.89mol), zinc powder 84.5g (1.3mol), trifluorovinyl zinc bromide mother liquor 46.2g ( Actual trifluorovinyl zinc bromide 11.3g, 0.05mol, Example 1), mechanically stirred and lowered the temperature to 0°C, slowly introduced 161g (1.0mol) of trifluoroethylene bromide, and kept warm at 40°C after the reaction was triggered, until the reaction liquid The conversion of bromotrifluoroethylene is complete. Stirring was stopped, and the excess zinc powder was separated after cooling down to room temperature to obtain a zinc reagent solution. use 19 FNMR quantification (trifluorotoluene as internal standard), the reaction yield was 86.9%.

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Abstract

The invention discloses a preparation method of hexafluoro-1,3-butadiene. 1,1,2-trifluoroethenyl zinc bromide and a nonmetal oxidizing agent halogen are reacted in order to form hexafluoro-1,3-butadiene. The preparation method has the advantages of simple process, high reaction yield, low raw material cost, and small "three wastes (waste gas, waste water and industrial residue)"; hexafluoro-1,3-butadiene is suitable for preparing dry etching gas and the like.

Description

technical field [0001] The invention relates to a preparation method of conjugated olefin, in particular to a preparation method of hexafluoro-1,3-butadiene. Background technique [0002] Hexafluoro-1,3-butadiene is a new type of dry etching gas with excellent etching performance. It is mainly used in the field of semiconductor etching, such as for the production of rectifier circuit boards containing Cu and low K dielectric constant. During etching, the accuracy of key dimensions can reach 100nm, and it has better selectivity and aspect ratio than other etching gases. In addition, hexafluoro-1,3-butadiene also has excellent environmental performance, its atmospheric existence time is only 1.9d, and has a lower GWP value, compared with the classic etching gas C 3 f 8 and c-C 4 f 8 , the GWP emitted by hexafluoro-1,3-butadiene during the etching process was reduced by 80% and 82%, respectively. Therefore, hexafluoro-1,3-butadiene has high market potential and is an impor...

Claims

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Application Information

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IPC IPC(8): C07C17/281C07C21/18
CPCC07C17/281C07F3/06C07C21/18
Inventor 吴海锋刘武灿方小青蒋芬芳
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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