Method for preparing fluoroalkane compound from fluorinated epoxide

A technology of oxides and fluorinated rings, applied in the preparation of hydroxyl compounds, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of high risk, increased by-products, and difficult industrialization, and achieves less by-products, Simple operation, safe and controllable effect of raw materials

Pending Publication Date: 2022-05-17
浙江诺亚氟化工有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the electrochemical fluorination technology usually uses alkanes or partially fluorinated alkanes as the reaction raw materials, and the corresponding fluoroalkanes are obtained by electrofluorination after adding hydrogen fluoride. Although this technical solution has certain feasibility, it cannot avoid the electrofluorination technology. The unique reaction selectivity is low, the by-product content is high, the disadvantages such as large energy consumption, the industrialization is difficult, and the economic benefit is low
[0003] However, fluorine gas fluorination technology usually uses fluorinated alkenes or alkynes as raw materials, and removes unsaturated bonds in the structure through fluorine gas addition reaction to obtain corresponding fluoroalkanes. Obviously, this solution requires the use of fluorine gas, which is dangerous. At the same time, if the raw fluoride structure contains other atoms such as hydrogen, chlorine, bromine, etc., the fluorine gas may undergo a substitution reaction to replace heteroatoms during the addition reaction process, resulting in a decrease in reaction selectivity , increased by-products and other issues

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  • Method for preparing fluoroalkane compound from fluorinated epoxide
  • Method for preparing fluoroalkane compound from fluorinated epoxide
  • Method for preparing fluoroalkane compound from fluorinated epoxide

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Example 1: Preparation of perfluorohexane from perfluoro-2-methyl-2,3-epoxypentane.

[0026] In a dry and clean 1L autoclave, add 100g of diethylene glycol dimethyl ether, 241.5g (1.5mol) of triethylamine hydrogen fluoride salt, and 316g of perfluoro-2-methyl-2,3-epoxypentane ( 1mol); close the reaction kettle, turn on the reaction kettle to stir, gradually increase the reaction temperature to 130°C, stir and react for 24 hours, after the reaction is completed, cool to room temperature, take out the reaction solution, and wash the reaction solution twice with a mass concentration of 10% sodium carbonate solution. Separation, the lower organic phase was obtained and washed three times with pure water, and the crude product was obtained by liquid separation. After the crude product was purified by rectification, 307.92 g of the pure product perfluorohexane was obtained, and the reaction yield was 91.1%.

Embodiment 2

[0027] Example 2: Perfluoro-4-methyl-3-isopropyl-2,3-epoxypentane Preparation of perfluoro-2-methyl-3-isopropylpentane.

[0028] In a dry and clean 1L autoclave, add 100g of diethylene glycol dimethyl ether, 241.5g (1.5mol) of triethylamine hydrogen fluoride, perfluoro-4-methyl-3-isopropyl-2,3- 466g (1mol) of pentylene oxide, close the reaction kettle, start the reaction kettle to stir, gradually increase the reaction temperature to 180°C, stir and react for 24h, after the reaction is completed, cool to room temperature, take out the reaction solution, and use a mass concentration of 10% sodium carbonate solution Wash the reaction solution twice, separate the liquids, and wash the lower organic phase with pure water three times, separate the liquids to obtain the crude product, and obtain the pure product perfluoro-2-methyl-3-isopropylpentane after the crude product is purified by rectification Alkane 437.74g, reaction yield 89.7%.

Embodiment 3

[0029] Example 3: The operation steps are the same as in Example 1, except that the hydrogen fluoride source is changed from triethylamine hydrogen fluoride to dimethylamine hydrogen fluoride.

[0030] In a dry and clean 1L autoclave, add 100g of diethylene glycol dimethyl ether, 127.5g (1.5mol) of dimethylamine hydrogen fluoride, and 316g of perfluoro-2-methyl-2,3-epoxypentane ( 1mol). Close the reaction kettle, turn on the reaction kettle to stir, gradually increase the reaction temperature to 130°C, stir and react for 24 hours, after the reaction is completed, cool to room temperature, take out the reaction solution, wash the reaction solution twice with a mass concentration of 10% sodium carbonate solution, and separate the liquid. The obtained lower organic phase was washed three times with pure water, and the crude product was obtained by liquid separation. After the crude product was purified by rectification, 298.92 g of the pure product perfluorohexane was obtained, a...

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Abstract

The invention discloses a method for preparing a fluoroalkane compound from fluorinated epoxide, which comprises the following specific operation steps: putting fluorinated epoxide, hydrogen fluoride salt of amine and an aprotic solvent or an organic amine solvent into a reaction kettle together, heating the reaction kettle to 50-200 DEG C, stirring to react for 24 hours, cooling to normal temperature, and filtering to obtain the fluoroalkane compound. And taking out the product, and carrying out alkali washing, water washing, liquid separation and rectification purification to obtain the corresponding fluoroalkane compound. The method has the advantages of simple operation, safe and controllable raw materials, reaction yield of more than 90%, few by-products and environmental friendliness, has obvious advantages compared with an electric fluorination process and a fluorine gas fluorination process for preparing the fluoroalkane compound, and has industrial potential.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing fluoroalkane compounds from fluorinated epoxides. Background technique [0002] At present, there are mainly two methods for the synthesis of fluoroalkane compounds, one is electrochemical fluorination technology, and the other is fluorine gas fluorination technology. Among them, the electrochemical fluorination technology usually uses alkanes or partially fluorinated alkanes as the reaction raw materials, and the corresponding fluoroalkanes are obtained by electrofluorination after adding hydrogen fluoride. Although this technical solution has certain feasibility, it cannot avoid the electrofluorination technology. The unique reaction selectivity is low, the by-product content is high, the disadvantages such as large energy consumption, industrialization is difficult, and economic benefit is low. [0003] However, fluorine gas fluori...

Claims

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Application Information

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IPC IPC(8): C07C17/16C07C19/08
CPCC07C17/16C07C29/106C07C19/08C07C31/38Y02P20/55
Inventor 章鑫辉李志斌吴家靖
Owner 浙江诺亚氟化工有限公司
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