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Preparation method of hexafluoroisobutene

A technology for hexafluoroisobutene and hexafluoroisobutanol is applied in the field of preparation of hexafluoroisobutene, can solve problems such as being unsuitable for industrial production, unsuitable for large-scale production, unfavorable for industrialization, etc., and achieves improved resource utilization, cheap raw materials, Easy-to-operate effects

Inactive Publication Date: 2017-09-12
JUHUA GROUP TECH CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Hexafluoroisobutene is a very useful chemical product and an important fluorine-containing special monomer for the development of new fluorine-containing polymers. It has a wide range of uses, such as the preparation of piezoelectric materials, lubricating materials, special elastomers, fluorine coatings, semiconductors Photolithographic materials, refrigerants, pharmaceutical intermediates, etc., new application fields are being discovered constantly, attracting more and more people's attention, and their preparation process has attracted people's strong attention, and there have been no related patent reports in China
But no matter which kind of all has its own problems, such as hexafluoropropylene raw material is cheap and easy to get, but the yield is low, it is not suitable for industrial production
The hexafluoroacetone method has a short process route and high yield, but anhydrous hexafluoroacetone and ketene are highly toxic and the reaction is generally carried out at high temperature, the process is difficult and costly, which is not conducive to industrialization
[0025] The above methods also have defects such as long routes, low yields, or difficult access to raw materials, and are not suitable for large-scale production.

Method used

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  • Preparation method of hexafluoroisobutene
  • Preparation method of hexafluoroisobutene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～7

[0046] To prepare methyl hexafluoroisobutyrate:

[0047] In a 250ml three-necked round-bottomed flask, add 106g (0.5mol) of heptafluoroisobutenyl methyl ether and anhydrous methanol, 120ml of solvent tetrahydrofuran (THF), halide, after adding, slowly warming up to the reaction temperature under stirring to start the reaction, After the reaction finishes, cooling is filtered, and the filtrate is rectified under normal pressure to obtain methyl hexafluoroisobutyrate. The implementation parameters and results are shown in Table 1, and wherein transformation efficiency and selectivity are all based on heptafluoroisobutenyl methyl ether.

[0048] Table 1 Examples 1-7 Implementation Parameters and Results

[0049]

[0050]

Embodiment 8～14

[0052] To prepare hexafluoroisobutanol:

[0053] In a 250ml three-necked round-bottomed flask, add 105g (0.5mol) of methyl hexafluoroisobutyrate prepared in Examples 1 to 7 and 50ml of solvent THF, then cool down to 10° C., add dropwise the tetrahydrofuran solution ( 1mol / L), add, adjust the temperature to the reaction temperature, continue stirring, after the reaction finishes, quench with 6mol / L hydrochloric acid, filter, and rectify the filtrate to obtain hexafluoroisobutanol, and the implementation parameters and results are shown in Table 2. The conversion rate and selectivity are all based on methyl hexafluoroisobutyrate.

[0054] Table 2 Implementation parameters and results of Examples 8 to 14

[0055]

Embodiment 15～21

[0057] To prepare hexafluoroisobutene:

[0058] In a 250ml three-necked round-bottomed flask, add 91g (0.5mol) of hexafluoroisobutanol prepared in Examples 8 to 14 and a base, 120ml of 1,1-dichloroethane as a solvent, and adjust the temperature to the reaction temperature after the addition. After the reaction, the product was condensed and received at -78°C, and rectified to obtain hexafluoroisobutene. The implementation parameters and results are shown in Table 3. The conversion rate and selectivity are all based on hexafluoroisobutanol.

[0059] Table 3 Implementation parameters and results of Examples 15 to 21

[0060]

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Abstract

The invention discloses a preparation method of hexafluoroisobutene, comprising the steps of (1) reacting heptafluoroisobutene methyl ether, methanol and a halide in type I solvent, cooling after reacting, filtering, rectifying the filtrate to obtain methyl hexafluoroisobutyrate; (2) allowing the methyl hexafluoroisobutyrate of step (1) to react with a reducing agent in type II solvent, quenching with hydrochloric acid after reacting, filtering, rectifying the filtrate to obtain hexafluoroisobutanol; (3) allowing the hexafluoroisobutanol of step (2) to react with an alkali in a molar ratio of 1:(1-10) in type III solvent, collecting the reaction product, and rectifying to obtain finished hexafluoroisobutene. The preparation method has the advantages that the process is simple, the yield is high, the raw materials are low in price and easy to obtain and the preparation method is suitable for industrialization.

Description

technical field [0001] The invention relates to a preparation method of hexafluoroisobutene, and belongs to the field of organic synthesis. Background technique [0002] Hexafluoroisobutene [3,3,3-trifluoro-2-(trifluoromethyl)-1-propene, referred to as HFIB], colorless, transparent liquid, CAS382-10-5, molecular weight 164.05, boiling point 14.5℃, critical The temperature is 164°C, the density is 1.39g / ml, and it is slightly soluble in water (0.23g / L, 23°C). [0003] Hexafluoroisobutene is a very useful chemical and an important fluorine-containing special monomer for the development of new fluorine-containing polymers. It is widely used, such as the preparation of piezoelectric materials, lubricating materials, special elastomers, fluorine coatings, semiconductors Photolithography materials, refrigerants, pharmaceutical intermediates, etc., new application fields are constantly being discovered, attracting more and more people's attention, and their preparation processes h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/35C07C21/18
CPCC07C17/35C07C29/147C07C67/00C07C21/18C07C31/38C07C69/63
Inventor 吕杨叶立峰蒋琦李宏峰王宗令
Owner JUHUA GROUP TECH CENT
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