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Method for preparing trifluoropropylene oxide

A technology of trifluoropropylene oxide and trifluoropropylene, which is applied in the direction of organic chemistry, can solve the problems of high environmental pressure, high toxicity of mercury acetate, and restrictions on the large-scale production of trifluoropropylene oxide, and achieve the effect of a simple method

Inactive Publication Date: 2012-09-05
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 trifluoropropylene oxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Take 143 grams (1 mol) of calcium hypochlorite, dissolve it in water, add 90 grams (1 mol) of oxalic acid, stir vigorously and then filter to obtain an aqueous solution of hypochlorous acid. Immediately bubble the trifluoropropene into the aqueous solution of hypochlorous acid. Stir vigorously. Control the temperature of the reaction system below 30°C. When the reaction system is nearly neutral with pH test paper, stop feeding trifluoropropene. Thereafter, the reaction system was heated to 90° C., 500 g of 20% (2.5 mol) sodium hydroxide solution was added dropwise to the reaction system, and the distillate was cooled to obtain trifluoropropylene oxide. The rate of addition of sodium hydroxide is 2-3 drops / second, until the reaction system no longer produces distillate after the dropwise addition, the reaction ends. A total of 33.6 g of trifluoropropylene oxide was obtained with a yield of 15%.

[0022] H NMR spectrum ( 1 H NMR, 200MHz, CDCl 3 ) δ 3.35(m, 1H), 2.63...

Embodiment 2

[0024] Take 28.6 grams (0.2 mol) of calcium hypochlorite, dissolve it in water, add 18 grams (0.2 mol) of oxalic acid, stir vigorously and then filter to obtain an aqueous solution of hypochlorous acid. Immediately bubble the trifluoropropene into the aqueous solution of hypochlorous acid. Stir vigorously. Control the temperature of the reaction system below 30°C. When the reaction system is nearly neutral with pH test paper, stop feeding trifluoropropene. Thereafter, the reaction system was heated to 95° C., 100 g of 20% (0.5 mol) sodium hydroxide solution was added dropwise to the reaction system, and the distillate was cooled to obtain trifluoropropylene oxide. The rate of addition of sodium hydroxide is 2-3 drops / second, until the reaction system no longer produces distillate after the dropwise addition, the reaction ends. A total of 4.5 g of trifluoropropylene oxide was obtained. The yield is 10%.

[0025] H NMR spectrum ( 1 H NMR, 200MHz, CDCl 3 ) δ 3.34(m, 1H), 2...

Embodiment 3

[0027] Take 85.8 grams (0.6 mol) of calcium hypochlorite, dissolve it in water, add 54 grams (0.6 mol) of oxalic acid, stir vigorously and then filter to obtain an aqueous solution of hypochlorous acid. Immediately bubble the trifluoropropene into the aqueous solution of hypochlorous acid. Stir vigorously. Control the temperature of the reaction system below 30°C. When the reaction system is nearly neutral with pH test paper, stop feeding trifluoropropene. Thereafter, the reaction system was heated to 95° C., 300 g of 20% (1.5 mol) sodium hydroxide solution was added dropwise to the reaction system, and the distillate was cooled to obtain trifluoropropylene oxide. The rate of addition of sodium hydroxide is 2-3 drops / second, until the reaction system no longer produces distillate after the dropwise addition, the reaction ends. A total of 16.1 g of trifluoropropylene oxide was obtained. The yield was 12%.

[0028] H NMR spectrum ( 1 H NMR, 200MHz, CDCl 3 ) δ 3.35(m, 1H),...

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Abstract

The invention relates to a method for preparing trifluoropropylene oxide, which comprises the following steps of: introducing trifluoropropene into fresh prepared aqueous solution of hypochlorous acid, heating the reaction system to between 90 and 95 DEG C, dripping sodium hydroxide solution into the reaction system, and cooling a distillate to obtain the trifluoropropylene oxide. The preparationmethod has the advantages that: a reagent which is virulent or generates great environmentally-friendly pressure is not used, and the trifluoropropylene oxide can be prepared by the simpler 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 Patents(China)
IPC IPC(8): C07D303/08C07D301/26
Inventor 许峰高源
Owner BEIJING OKEANOS TECH