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Method for preparing trifluoroepoxypropane

A technology of trifluoropropylene oxide and trifluoroacetaldehyde, applied in the direction of organic chemistry and the like, can solve the problems of high price of N-bromosuccinimide, high toxicity of mercury acetate, high environmental protection pressure and the like

Inactive Publication Date: 2010-12-01
BEIJING OKEANOS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mercury acetate is very toxic; the use of oleum and liquid bromine will cause great environmental pressure; N-bromosuccinimide is expensive
All these disadvantages limit the large-scale production of trifluoropropylene oxide by the method of bromo-acetate and ring closure reaction of trifluoropropene

Method used

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  • Method for preparing trifluoroepoxypropane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 29.4 g of dimethyl sulfide into the three-necked flask, raise the temperature to 30°C, add 18.3 g of dimethyl sulfate dropwise, and vigorously stir the reaction system with mechanical stirring while adding dropwise. The dimethyl sulfate was added dropwise within 10 minutes, then the temperature was raised to 45°C, and the temperature was kept for about 1 hour, then 8.6 grams of trifluoroacetaldehyde, 4 grams of dimethyl sulfoxide and 21.2 grams of potassium hydroxide were added, and the temperature was raised after the addition was completed. The reaction was carried out at 50°C, and after 1 hour, the temperature of the reaction system was raised to 70°C, and 3.9 g of trifluoropropylene oxide was obtained by distillation. The yield is 40%.

[0023] H NMR spectrum ( 1 H NMR, 200MHz, CDCl 3 ) δ 3.35(m, 1H), 2.63(m, 1H), 2.38(m, 1H). Mass spectrum (EI): 112(100), 113(0.1).

Embodiment 2

[0025] Add 167.4 g of dimethyl sulfide into the three-necked flask, raise the temperature to 35° C., add 104 g of dimethyl sulfate dropwise, and vigorously stir the reaction system with mechanical stirring while adding dropwise. Dimethyl sulfate was added dropwise within 20 minutes, then the temperature was raised to 45°C, and the temperature was kept for about 2 hours, then 49 grams of trifluoroacetaldehyde, 22.6 grams of dimethyl sulfoxide and 103 grams of potassium hydroxide were added, and the temperature was raised after the addition After 2 hours, the temperature of the reaction system was raised to 90° C., and 28 g of trifluoropropylene oxide was obtained by distillation. The yield is 50%.

[0026] H NMR spectrum ( 1 H NMR, 200MHz, CDCl 3 ) δ 3.34(m, 1H), 2.62(m, 1H), 2.35(m, 1H). Mass spectrum (EI): 112(100), 113(0.1).

Embodiment 3

[0028] Add 83.7 g of dimethyl sulfide into the three-necked flask, raise the temperature to 30°C, add 58.6 g of methyl iodide dropwise, and vigorously stir the reaction system with mechanical stirring while adding dropwise. The dimethyl sulfate was added dropwise within 15 minutes, then the temperature was raised to 40°C, and the temperature was kept for about 1 hour, then 24.5 grams of trifluoroacetaldehyde, 11.3 grams of dimethyl sulfoxide and 51.5 grams of potassium hydroxide were added, and the temperature was raised after the addition The reaction was carried out at 50°C, and after 1 hour, the temperature of the reaction system was raised to 80°C, and 12.6 g of trifluoropropylene oxide was obtained by distillation. The yield is 45%.

[0029] H NMR spectrum ( 1 H NMR, 200MHz, CDCl 3 ) δ 3.35(m, 1H), 2.63(m, 1H), 2.38(m, 1H). Mass spectrum (EI): 112(100), 113(0.1).

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Abstract

The invention relates to a method for preparing trifluoroepoxypropane, which comprises the following steps: 1), reacting dimethyl sulphide with methylating reagent MeX in a reactor to obtain a sulfur ylid; and 2) adding trifluoro acetaldehyde, dimethylsulfoxide and potassium hydroxide into the reactor to allow the sulfur ylid generated by the step 1) to form sulfur ylide under the action of the potassium hydroxide and to allow the sulfur ylide to react with the trifluoro acetaldehyde, and obtaining trifluoroepoxypropane by distillation. The preparation method of the invention has the advantages that: reagents with high toxicity and high environmental pressure producing capacity are not used, and the trifluoroepoxypropane is prepared simply. The yield of the method can be compared with the conventional method.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing trifluoropropylene oxide. Background technique [0002] When drug molecules are replaced by fluorine, their biological activity is usually affected. After some optoelectronic devices are replaced by fluorine, their physical properties will also change. Therefore, the development of new synthetic methodologies for organofluorine compounds has aroused widespread interest among synthetic chemists. Recently, a large number of chiral or achiral fluorinated molecular modules have been developed for the synthesis of fluorinated organic molecules. Among them, trifluoropropylene oxide is a synthetic intermediate with multiple uses, which is widely used in materials and medicinal chemistry. For example, the ring-opening reaction of trifluoropropylene oxide with a series of N-benzylaniline derivatives will give a series of N,N-disubstituent-trifluoro-3-amino-2-prop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/08C07D301/02
Inventor 许峰高源
Owner BEIJING OKEANOS TECH