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Synthesis method of tetrafluoropropyl trifluoroethylene ether

A technology of tetrafluoropropyl trifluorovinyl ether and tetrafluoropropanol, which is applied in the field of compound synthesis, can solve the problems of safety hazards, difficult industrial production, lack of tetrafluoropropyl trifluorovinyl ether, and inability to reflect useful value, and the like, Achieve the effect of reducing reaction risk, reducing reaction steps, and easy industrial production

Active Publication Date: 2020-04-17
ZHONGHAO CHENGUANG RES INST OF CHEMICALINDUSTRY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Trifluoroethylene is difficult to separate and purify from tetrafluoroethylene, and it is often treated by incineration, so it cannot reflect useful value
[0005] At present, there is basically no relevant research on tetrafluoropropyl trifluoroethylene ether at home and abroad, and the supply of goods in the market is vacant, and this product has an important impact on some fluoroether oligomers with excellent low temperature resistance
A German document in 1967 disclosed a preparation method of tetrafluoropropyltrifluoroethylene ether [see Yakubovich, A.Ya.et al.; J.Gen.Chem.USSR (Engl.Transl.); 1967, 37,797-801.], with tetrafluoroethylene as raw material, under the catalysis of metal sodium, react with tetrafluoropropanol to prepare tetrafluoropropyl trifluoroethylene ether, and the highly active tetrafluoroethylene is used in its preparation method Monomers, and very active metal sodium, generate hydrogen during the reaction process, which has potential safety hazards and is not easy to carry out industrial production. At the same time, this method uses 1,4-dioxane as a solvent, which makes the cost higher, and the treatment of organic waste liquid is also very tedious work

Method used

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  • Synthesis method of tetrafluoropropyl trifluoroethylene ether
  • Synthesis method of tetrafluoropropyl trifluoroethylene ether
  • Synthesis method of tetrafluoropropyl trifluoroethylene ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] This example relates to the preparation of 1,2-dibromo-1,1,2-trifluoroethane intermediate, including the following steps:

[0046] Add 176g (1.1mol) of liquid bromine into the reactor, slowly bubble the trifluoroethylene "waste gas" mixed with tetrafluoroethylene produced in the production process of tetrafluoroethylene, and heat to 55°C to start the reaction until the reaction The liquid turns from dark red to clear and transparent liquid, and the mixed gas is stopped.

[0047] After the reaction was completed, the reaction product was washed successively with saturated sodium bisulfite solution and saturated brine. After extracting the organic layer, dry it with anhydrous sodium sulfate, and filter it with suction to obtain a crude product. Then, 193.4 g of 1,2-dibromo-1,1,2-trifluoroethane and 51.9 g of 1,2-dibromo-1,1,2,2-tetrafluoroethane were separated by rectification.

Embodiment 2

[0049] This embodiment relates to the preparation of tetrafluoropropyltrifluoroethylene ether, comprising the steps of:

[0050] Add 132g (1.0mol) of tetrafluoropropanol, 140g (2.5mol) of potassium hydroxide, and 300ml of deionized water into the reactor, raise the temperature of the reaction system to 80°C, and slowly add 1,2-dibromo-1 , 193.4g (0.8mol) of 1,2-trifluoroethane, continue to react for 2h after the dropwise addition is completed.

[0051] After the reaction was completed, the system was washed with water, extracted and separated to obtain a crude product, and finally purified by rectification to obtain 12.5 g of the target product tetrafluoropropyltrifluoroethylene ether with a purity of 99.3% and a total yield of 7.4%.

Embodiment 3

[0053] This embodiment relates to the preparation of tetrafluoropropyltrifluoroethylene ether. Compared with Example 2, the main difference is that 0.1mol of the reaction accelerator glyme is added, including the following steps:

[0054] Add 132g (1.0mol) of tetrafluoropropanol, 140g (2.5mol) of potassium hydroxide, and 300ml of deionized water into the reactor, and add 13.4g (0.1mol) of reaction accelerator diglyme at the same time, and the reaction system The temperature was raised to 80°C, and then 193.4 g (0.8 mol) of 1,2-dibromo-1,1,2-trifluoroethane was slowly added dropwise, and the reaction was continued for 2 hours after the dropwise addition was completed.

[0055] After the reaction was completed, the system was washed with water, extracted and separated to obtain a crude product, and finally purified by rectification to obtain 139.1 g of the target product tetrafluoropropyltrifluoroethylene ether with a purity of 99.5% and a total yield of 82%. The 1HNMR informati...

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Abstract

The invention relates to a preparation method of tetrafluoropropyl trifluoroethylene ether. The preparation method comprises the following main steps: in an alkaline environment, under the condition of heating, carrying out substitution and elimination on tetrafluoropropanol and 1,2-dibromo-1,1,2-trifluoroethane to obtain the tetrafluoropropyl trifluoroethylene ether. Compared with the existing reaction, the method provided by the invention has the advantages of simple reaction type, mild reaction conditions, strong operability, no use of organic solvents, environmental protection, fast reaction rate and high product yield, overcomes the difficulty of using metallic sodium and organic solvents in the prior art, reduces the reaction risk, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a synthesis method of tetrafluoropropyl trifluoroethylene ether. Background technique [0002] In the production of organic fluorine industry, tetrafluoroethylene is an important raw material for the production of fluororesins and fluororubbers. Tetrafluoroethylene is generally prepared by pyrolysis of difluorochloromethane, and about 0.1% to 0.2% of a by-product—trifluoroethylene (TrFE or HFC-1123 for short) will also be produced during the pyrolysis process. Chenguang Institute produces more than 20,000 tons of tetrafluoroethylene every year, but it is also accompanied by about 20 to 40 tons of trifluoroethylene "waste gas". Trifluoroethylene is difficult to separate and purify from tetrafluoroethylene, and it is often treated by incineration, so it cannot reflect useful value. [0003] Tetrafluoropropanol is widely used as a variety of solvents due to its good solubility, f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/24C07C43/17
CPCC07C17/04C07C41/24C07C19/14C07C43/17
Inventor 刘波罗源军张鸣李斌陈立义
Owner ZHONGHAO CHENGUANG RES INST OF CHEMICALINDUSTRY CO LTD
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