Method for preparing perfluoro olefin ether from compound containing acid-sensing group

A perfluoroalkene ether compound technology, applied in the field of perfluoroalkene ether compounds, can solve problems such as decomposition and chain scission, difficulty in fluorination, low reaction yield, etc., achieve enhanced stability, reduce decomposition and chain scission, Good effect of perfluorinated effect

Active Publication Date: 2009-03-04
CHINA BLUESTAR CHENGRAND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because this method involves a strong acid environment in the synthesis of partially fluorinated raw materials and perfluorinated steps, it is difficult to achieve good fluorination for ether compounds containing acid-sensitive groups
[0009] For the above-mentioned various systems, the reaction process, especially the fluorination process of fluorine gas, mostly involves a strong acid environment, so for ether compounds containing acid-sensitive groups, decomposition and chain scission are extremely easy to occur, making it difficult to implement fluorination, and the final reaction yield Very low or very difficult to produce expected product
[0010] It is particularly noteworthy that the above-mentioned patent documents such as U.S. Patent US3692843 (Resnick) and world patent WO2001046107 (Worm), the former uses perfluoroalkyl acid fluoride (R f COF) reacts with hexafluoropropylene oxide to obtain the general formula CF 3 O(CF 2 O) n CF 2 CF 2 OCF=CF 2 Perfluoroalkenyl ether precursor compounds; the latter from the general formula R h OCF (CF 3 )COOR h Partially fluorinated raw materials are perfluorinated to prepare alkenyl ethers, because the preparation of perfluorinated acid fluorides is not easy, and the current application range of partial fluorinated methods is limited, and the atomic economic efficiency needs to be improved. For example, R as an ester group h Utilization issues in fluoridation process

Method used

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  • Method for preparing perfluoro olefin ether from compound containing acid-sensing group
  • Method for preparing perfluoro olefin ether from compound containing acid-sensing group
  • Method for preparing perfluoro olefin ether from compound containing acid-sensing group

Examples

Experimental program
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Effect test

Embodiment 1

[0037] In a 250ml stainless steel reactor, add 1mol of CH 3 OCH 2 OCH 2 CH 2 OH and 1.5molNaF, stirred at room temperature, hexafluoropropylene oxide (HFPO) was passed into the reaction system in the form of bubbling from one outlet of the reactor, and its feed amount was based on the fact that the product content no longer increased, and the other The outlet is connected to a condenser, and the condenser is connected to a cold trap to cool the unreacted HFPO, and the cooled HFPO can be recycled. The reaction process was monitored by gas chromatography until the product content no longer increased, and the reaction was stopped. The reaction product was washed with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and distilled to obtain 0.35mol CH 3 OCH 2 OCH 2 CH 2 OCF (CF 3 ) COOCH 2 CH 2 OCH 2 OCH 3 , yield 70%. structure 1 HNMR, 19 Identification by F NMR and MS spectra.

Embodiment 2

[0039] In a 250ml stainless steel reactor, add 1mol of CH 3 OCH 2 (OCH 2 CH 2 ) 2 OH and 1.5molNaF, stirred at room temperature, passed into HFPO, the amount of its feed was based on the fact that the product content would no longer increase, and the unreacted HFPO was cooled down with a cold trap. The reaction process was monitored by gas chromatography until the product content no longer increased, and the reaction was stopped. The reaction product was processed in a similar manner to Example 1 to obtain 0.33molCH 3 OCH 2 (OCH 2 CH 2 ) 2 OCF (CF 3 )COO(CH 2 CH 2 O) 2 CH 2 OCH 3 , yield 65%. structure 1 HNMR, 19 Identification by F NMR and MS spectra.

Embodiment 3

[0041] In a 2L stainless steel reactor, add 20mol methanol, 0.12mol sodium hydroxide, stir at room temperature, after the alkali is dissolved, add 1mol CH 3 OCH 2 OCH 2 CH 2 OCF (CF 3 ) COOCH 2 CH 2 OCH 2 OCH 3 , heated to reflux, and reacted for 30 hours. The reaction process was monitored by gas chromatography until the product content no longer increased, and the reaction was stopped. The methanol was evaporated, the reaction product was washed with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and distilled to obtain 0.95mol CH 3 OCH 2 OCH 2 CH 2 OCF (CF 3 ) COOCH 3 , 95% yield. Collect distillate at the same time, recover HOCH 2 CH 2 OCH 2 OCH 3 . structure 1 H NMR, 19 Identification by F NMR and MS spectra.

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Abstract

The invention provides a method for preparing perfluoro-olefine ether from an acid-sensitive group-containing compound. The method comprises the following steps: carrying out the reaction between single-substituted glycols compound containing an MOM protecting group (CH3OCH2-) which is sensitive to acid, and hexafluoropropylene oxide; forming a part of fluoro ester through an ester exchange reaction; directly fluorizing the acid-sensitive group-containing compound with fluorine; and subjecting to cracking to obtain the perfluoro-olefine ether. The method is characterized in that the fluorization process adopts the gradual temperature rise method ( minus 20 DEG C to 15 DEG C), and the corresponding reaction temperature condition is applied according to the different requirements for the stability of molecular structures with different fluorization extents in different stages; and in the different temperature stages, sodium fluoride is added intermittently so as to effectively slow down the decomposition of the acid-sensitive group in the raw material in an strong acid environment.

Description

technical field [0001] The invention relates to a method for preparing a class of perfluoroalkenyl ether compounds by direct fluorine gas fluorination of raw materials containing acid sensitive groups. Background technique [0002] Fluorine-substituted vinyl monomers are widely used intermediates and starting materials for the preparation of highly fluorinated or perfluorinated polymers and copolymers. Perfluorovinyl ethers are a large class of fluorinated ether compounds containing polymerizable vinyl functional groups, and the other part of the molecule is an alkyl group, an alkyl ether, a disubstituted alkyl ether or a group containing a functional group such as a carboxylate . [0003] Known methods for preparing perfluorovinyl ethers containing alkyl ethers mainly include the following: [0004] U.S. Patent US3114778 (Fritz), US3250808 (Moore), US3692843 (Resnick) have described a kind of by perfluoroalkyl acid fluoride (R f COF) reacts with hexafluoropropylene oxide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/315C07C43/17C07C41/48C07C41/30
CPCY02P20/55
Inventor 袁立华杨晓勇刘洪乐冯文罗凯吴勇
Owner CHINA BLUESTAR CHENGRAND CO LTD
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