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Synthetic method of [alpha],[beta],[beta]-trifluorostyrene type compounds

A technique for the synthesis of trifluorostyrene, which is applied in the fields of chemical instruments and methods, organic chemistry, preparation of halogenated hydrocarbons, etc., and can solve problems such as unsmooth progress, low yield, and high trifluorostyrene

Active Publication Date: 2014-04-09
SHANGHAI 3F NEW MATERIAL TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthesis process and polymerization process of trifluorostyrene, after decades of research, has not progressed smoothly. So far, no company has achieved industrialization in monomer synthesis or polymerization.
[0019] Visible by above-mentioned test result, although the Grignard reagent C that this method makes 6 h 5 The concentration of MgBr can be as high as 97% (in tetrahydrofuran solvent), but the yield of trifluorostyrene produced by the final reaction with tetrafluoroethylene is only 55%.
Obviously, the trifluorostyrene synthesis method provided by this prior art document has the advantages of short synthetic route, mild process conditions, and cheap raw material cost, but its fatal shortcoming is that the yield is too low, which increases the production of trifluorostyrene as a result. cost

Method used

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  • Synthetic method of [alpha],[beta],[beta]-trifluorostyrene type compounds
  • Synthetic method of [alpha],[beta],[beta]-trifluorostyrene type compounds
  • Synthetic method of [alpha],[beta],[beta]-trifluorostyrene type compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] 1. Synthetic Grignard reagent

[0084] Add 68 grams of magnesium roll to a dry 5-liter three-necked round bottom flask equipped with a reflux device. After replacing with nitrogen, heat the flask to about 110°C for 3 hours while continuing to flow nitrogen, and then maintain the nitrogen flow. The flask was cooled down to room temperature. Add 1295 grams of tetrahydrofuran, 109 grams of chlorobenzene and 2 grains of iodine (about 0.2 grams) into the flask. Heat while stirring to make the liquid in the flask rise to reflux (about 65°C). After the reflux state is stable, add the mixture of tetrahydrofuran (555g) and chlorobenzene (180g) dropwise within 5~7 hours. After the dropwise addition, keep the reflux state and continue the reaction for 9 hours, then stop heating and stirring, and keep nitrogen flowing. . The liquid in the flask is the synthetic Grignard reagent. Under similar conditions, a tetrahydrofuran solution of chlorobenzone reagent with a concentration of ...

Embodiment 2

[0090] Synthetic trifluorostyrene

[0091] The 2-liter stainless steel pressure-resistant reaction vessel is replaced with nitrogen three times, and then 248 grams (1.8 mol / kg) of synthetic Grignard reagent and 754 grams of tetrahydrofuran are added. Cool while stirring. When it reaches -14°C, pass it in while maintaining stirring. 150 grams of tetrafluoroethylene. After the addition of tetrafluoroethylene is completed, start to slowly heat, so that the temperature in the container does not exceed 45°C, and keep the reaction for 6 hours. After the reaction is over, the heating and stirring are stopped, the residual tetrafluoroethylene (38.4 g) is evacuated and the material is discharged to obtain the trifluorostyrene synthesis liquid. The composition of the product was determined by liquid chromatography, and the results are listed in Table 1.

Embodiment 3

[0093] Trifluorostyrene synthesis

[0094] The 2-liter stainless steel pressure-resistant reaction vessel is replaced with nitrogen three times, and then 157 g (2.25 mol / kg) of synthetic Grignard reagent and 942 g of tetrahydrofuran are added, and the mixture is cooled while stirring. When it reaches -21°C, it is passed through while maintaining stirring. 165 grams of tetrafluoroethylene. After the addition of tetrafluoroethylene is completed, start to slowly heat, so that the temperature in the container does not exceed 45°C, and keep the reaction for 6 hours. After the reaction is over, the heating and stirring are stopped, the residual tetrafluoroethylene (41.3 g) is evacuated and the material is discharged to obtain a trifluorostyrene solution. The composition of the product was determined by liquid chromatography, and the results are listed in Table 1.

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Abstract

The invention discloses a synthetic method of [alpha],[beta],[beta]-trifluorostyrene type compounds. The method comprises: (i) a step of subjecting halogenobenzene to a Grignard reaction in an organic solvent to form a Grignard reagent having the following formula, wherein X is a chlorine atom or a bromine atom; and (ii) a step of subjecting the Grignard reagent and tetrafluoroethene, in an organic solvent, to an [alpha],[beta],[beta]-trifluorostyrene synthetic reaction to prepare the [alpha],[beta],[beta]-trifluorostyrene or substituted [alpha],[beta],[beta]-trifluorostyrene, with the molar ratio of the tetrafluoroethene to the Grignard reagent being not less than 1.

Description

Technical field [0001] The invention relates to a method for synthesizing trifluorostyrene compounds, which has the advantages of high yield, low cost and easy industrialization. Background technique [0002] Trifluorostyrene (α, β, β-trifluorostyrene, TFS for short) is a fluorine-containing monomer that can be used to prepare polymers and fluorine-containing intermediates. Polytriflurostyrene (PTFS) has good heat resistance, high transparency, good solubility, low dielectric loss, and radiation resistance. It is used in proton exchange membranes, ion exchange membranes, photoelectric communications, and filter materials. , Microelectronics and other fields have very wide application potential. [0003] The synthesis process and polymerization process of trifluorostyrene, after decades of research, has not progressed smoothly. So far, no company has achieved industrialization in monomer synthesis or polymerization. Cohen (Cohen SG, Wolosinski HT, Scheuer PJ. "α,β,β-trifluorostyre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/04C07C17/263C07C22/08
Inventor 袁利兵张东郭立富宋军胡根祥顾永平景蛟凯郑晓亮
Owner SHANGHAI 3F NEW MATERIAL TECH CO LTD
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