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Preparation method for perfluoro vinyl ether with sulfuryl fluoride group as terminal group

A technology of perfluorovinyl ether and fluorosulfonyl perfluoroalkyl acyl, applied in the field of fine chemicals, can solve the problem of complex synthesis and preparation methods, low yield, high cost of short-chain sulfonyl fluoride monomers, and inability to generate in one step problems such as alkenyl ether double bonds, to achieve the effects of low cost, avoidance of waste and high yield

Inactive Publication Date: 2017-10-24
SHANDONG HUAXIA SHENZHOU NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Regarding the preparation method of perfluorovinyl ether whose short-chain end group is a sulfonyl fluoride group, DuPont announced the preparation of an alkylene ether monomer containing a sulfonyl fluoride group in a short-chain structure as early as 1971 (US3560568) , by using the known FCOCF (CF 3 )OCF 2 CF 2 SO 2 F as a starting material, under the action of alkali metal carbonate, inevitably generates a five-membered cyclization intermediate, which is then ring-opened by sodium methoxide to generate CF 2 = CFOCF 2 CF 2 SO 3 Na, and then chlorinating and fluorinating the sodium sulfonic acid salt at the end to obtain the final product; this method cannot generate enene ether double bonds in one step, and the final product can only be obtained through multi-step reactions, and the final monomer yield is very low
Dow Chemical announced in U.S. Patent US4940525 that the potassium alkoxide salt of the isomer of tetrafluorosultone was reacted with pentafluoroepichlorohydrin to obtain a propylene oxide telomerization product, and then the corresponding monomer was obtained through high-temperature cracking; The synthesis and preparation method of pentafluoroepichlorohydrin is complex and the yield is not high, and the cost of preparing short-chain sulfonyl fluoride monomer is high

Method used

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  • Preparation method for perfluoro vinyl ether with sulfuryl fluoride group as terminal group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] FSO 2 CF 2 CF 2 o - K + Preparation of:

[0044] 1 liter three-necked flask, equipped with a thermometer and agitator, add 200mL of diethyl ether into the three-necked flask, then add 60g of potassium fluoride, then add FSO dropwise 2 CF 2 COF liquid (180g), the water bath controls the temperature in the reaction bottle to not exceed 25°C. After the addition, continue to stir at room temperature for 24 hours, and check that there is no residual acyl fluoride reagent FSO in the reaction solution 2 CF 2 After COF, the reaction mixture was transferred to a single-necked flask and spin-dried to obtain 235 g of yellow powder. Characterized correctly by infrared and NMR, in 19 In the FNMR spectrum, it was found that there was -28ppm of CF 2 OK structure.

[0045] FSO 2 CF 2 CF 2 Preparation of OCFClCFICl(IVa):

[0046] Under anhydrous and oxygen-free conditions, add 800 mL of diglyme to a 2L three-necked flask, and then add the prepared potassium alkoxide FSO un...

Embodiment 2

[0052] The preparation method is the same as Example 1, the only difference is: FSO 2 CF 2 CF 2 OCFClCF 2 The preparation of Cl(V) adopts the following method:

[0053] In a 500mL three-necked flask equipped with a reflux condenser, a stirrer and a constant pressure dropping funnel, add 60g of dry antimony trifluoride and 20mL of antimony pentachloride. When the internal temperature of the reaction bottle reaches 140°C, slowly add FSO 2 CF 2 CF 2 OCFClCFICl(IV) 100g, continue to reflux for 2-5h after the dropwise addition, and then fractionally distill to obtain a fraction at 117-120°C with a yield of 83%.

Embodiment 3

[0055] The preparation method is the same as Example 1, the only difference is: FSO 2 CF 2 CF 2 The preparation of OCFClCFBrCl (IVb) adopts the following method:

[0056] Under anhydrous and oxygen-free conditions, add 800 mL of diglyme to a 2L three-necked flask, and then add the prepared potassium alkoxide FSO under stirring. 2 CF 2 CF 2 o - K + , and then add 165g of liquid bromine, under ice bath (control the internal temperature of the reaction bottle not to exceed 10°C), slowly add difluorodichloroethylene (140g) solution dropwise, the dropwise addition is completed in 4 to 8 hours, and after continuing to react for 4 hours, the reaction is mixed Pour the liquid into ice water, and add 10% sodium thiosulfate aqueous solution to wash and extract the layers, and then rectify under reduced pressure to obtain the product FSO 2 CF 2 CF 2 OCFClCFBrCl.

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Abstract

The invention belongs to the field of fine chemicals and specifically relates to a preparation method for perfluoro vinyl ether with a sulfuryl fluoride group as a terminal group. The perfluoro vinyl ether with the sulfuryl fluoride group as the terminal group is prepared in the manner of taking fluorosulfonyl perfluoroalkyl fluoride as a raw material and performing salt forming reaction, fluoridation and reduction reaction. The perfluoro vinyl ether with the sulfuryl fluoride group as the terminal group is CF2=CFOCF2(CF2)nSO2F, wherein n is equal to 1-3. According to the invention, the fluorosulfonyl perfluoroalkyl fluoride is taken as the raw material, the raw material is commercialized and easily acquired, the cost is low, the high-temperature pyrolyzing route and the unconventional monomer are avoided, the product is acquired through high-yield reaction, much fluorine-containing effluent is prevented from generation and the cost is lowered. The yield is higher, the waste of fluorine resource is avoided and the generation of fluorine-containing waste is reduced.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of linear perfluorovinyl ether sulfonyl fluoride. Background technique [0002] Perfluorosulfonic acid ionomers have been used in the chlor-alkali industry and proton exchange membrane fuel cells since the 1970s. After decades of application and promotion, the technology has become more mature, and it has been widely used in many fields of the chemical industry. The use of perfluorosulfonic acid ion exchange membranes in electrolyzers and fuel cells is a known technology. Although many polymers can be prepared into ion exchange membranes, they are suitable as membrane materials for chlor-alkali ion membranes and fuel cell proton exchange membranes, and ion exchange membranes with ion exchange groups such as sulfonic acid groups and perfluorinated structures are more suitable. In the prior art, the preparation of perfluoroionic polymers containing su...

Claims

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Application Information

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IPC IPC(8): C07C303/22C07C309/82
CPCC07C303/22C07C309/82
Inventor 史大阔刘体建张永明唐军柯沈文凯杜冲冲
Owner SHANDONG HUAXIA SHENZHOU NEW MATERIAL
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