# US 5,350,497 A · Production of perfluoro(alkyl vinyl ethers)

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,350,497 A
- Document ID: US5350497A
- Status: Granted
- Kind: A
- Application number: 08/065,975
- Filed: 1993-05-21
- Granted: 1994-09-27
- Earliest claimed: 1993-05-21
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Ming-Hong Hung; Shlomo Rozen
- Web page: https://patentgrep.com/patent/US5350497A

## CPC

- C07C 43/123: {both carbon chains are substituted by halogen atoms}
- C07C 41/16: by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
- C07C 41/22: by introduction of halogens; by substitution of halogen atoms by other halogen atoms
- C07C 41/24: by elimination of halogens, e.g. elimination of HCl
- C07C 43/126: {having more than one ether bond}
- C07C 43/17: containing halogen
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Disclosed herein is a process for making perfluoro(alkyl vinyl ethers) by fluorination with elemental fluorine of selected novel partially fluorinated (di)chloroethyl ethers, followed by dehalogenation to the corresponding perfluoro(alkyl vinyl ether). The perfluoro(alkyl vinyl ethers) are useful as monomers for molding resins and elastomers.

## Claims

### Claim 1

A process for the production of perfluoro(alkyl vinyl ethers), comprising, fluorinating with elemental fluorine a first compound of the formula R.sup.1 CHX.sup.3 OCX.sup.1 X.sup.2 CX.sup.1.sub.2 X.sup.2, to form a second compound of the formula R.sup.2 CF.sub.2 OCFX.sup.2 CF.sub.2 X.sup.2, and dehalogenating said second compound to form a perfluoro(alkyl vinyl ether) of the formula R.sup.2 CF.sub.2 OCF.dbd.CF.sub.2,
wherein:
R.sup.1 is hydrogen, a fluorinated alkyl group, or a fluorinated alkyl group containing one or more ether oxygen atoms between alkylene segments;
each X.sup.1 and X.sup.3 is independently hydrogen or fluorine;
in said first compound each X.sup.2 is independently chlorine, bromine, iodine, or fluorine, provided that at least one of X.sup.2 is chlorine;
in said second compound each X.sup.2 is independently chlorine or fluorine, provided that at least one of X.sup.2 is chlorine; and
R.sup.2 is fluorine, perfluoroalkyl, or perfluoroalkyl containing one or more ether oxygen atoms between alkylene segments.

### Claim 2 (depends on 1)

The process as recited in claim 1 wherein R.sup.1 is perfluoroalkyl, H(CF.sub.2).sub.n -- where n is 1 to 20, hydrogen, or perfluoroalkyl containing one or more ether oxygen atoms between alkylene segments.

### Claim 3 (depends on 2)

The process as recited in claim 2 wherein R.sup.1 is F(CF.sub.2).sub.n -- where n is 1 to 20, hydrogen, or C.sub.3 F.sub.7 O[CF(CF.sub.3)CF.sub.2 O].sub.y CF(CF.sub.3)--, wherein y is 0 or an integer of 1 to 8.

### Claim 4 (depends on 2)

The process as recited in claim 2 wherein each X.sup.1 is fluorine, each X.sup.2 is chlorine, and X.sup.3 is hydrogen.

### Claim 5 (depends on 4)

The process as recited in claim 4 wherein said fluorinating is carried out at about -30.degree. C. to about +50.degree. C., using a solvent, a mixture of said elemental fluorine and an inert gas, and agitation.

### Claim 6 (depends on 4)

The process as recited in claim 4 wherein said fluorination is carried out while being exposed to ultraviolet radiation.

### Claim 7 (depends on 1)

The process as recited in claim 1 wherein each X.sup.1 is fluorine, each X.sup.2 is chlorine, and X.sup.3 is hydrogen.

### Claim 8 (depends on 1)

The process as recited in claim 1 wherein each X.sup.2 is chlorine.

### Claim 9 (depends on 8)

The process as recited in claim 8 wherein said first compound is prepared by chlorination of R.sup.1 CH.sub.2 OCF.dbd.CF.sub.2 with Cl.sub.2.

### Claim 10 (depends on 1)

The process as recited in claim 1 wherein said fluorinating is carried out at about -30.degree. C. to about +50.degree. C.

### Claim 11 (depends on 1)

The process as recited in claim 1 wherein said fluorinating is carried out using a solvent.

### Claim 12 (depends on 1)

The process as recited in claim 1 wherein a mixture of said elemental fluorine and an inert gas is used.

### Claim 13 (depends on 1)

The process as recited in claim 1 wherein agitation is used.

### Claim 14 (depends on 1)

The process as recited in claim 1 wherein said fluorinating is carried out at about -30.degree. C. to about +50.degree. C., using a solvent, a mixture of said elemental fluorine and an inert gas, and agitation.

### Claim 15 (depends on 1)

The process as recited in claim 1 wherein said dehalogenating is carried out with a metal or a metal reducing agent.

### Claim 16 (depends on 1)

The process as recited in claim 1 wherein said dehalogenating is carried out with zinc, TiCl.sub.4 /LiAlH.sub.4, magnesium or copper.