# US 5,347,058 A · Process for the production of fluorinated olefins

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- Number: US 5,347,058 A
- Document ID: US5347058A
- Status: Granted
- Kind: A
- Application number: 08/163,497
- Filed: 1993-12-07
- Granted: 1994-09-13
- Earliest claimed: 1993-12-07
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: William B. Farnham
- Web page: https://patentgrep.com/patent/US5347058A

## CPC

- C07C 17/363: by elimination of carboxyl groups
- C07C 17/361: by reactions involving a decrease in the number of carbon atoms
- C07F 7/1896: {Compounds having one or more Si-O-acyl linkages}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Fluorinated olefins are produced by thermolysis of a silyl ester of a fluorinated aliphatic carboxylic acid in the presence of a catalyst which provides fluoride ion, such as potassium fluoride. The fluorinated olefins are useful as monomers and chemical intermediates.

## Claims

### Claim 1

A process for the production of fluorinated olefins, comprising, heating to a temperature of about 150.degree. C. to about 400.degree. C. a compound of the formula R.sup.1 R.sup.2 CFCR.sup.4 R.sup.5 C(O)OSiR.sup.3.sub.3, in the presence of a thermolysis catalyst, wherein:
R.sup.1 and R.sup.2 are each independently fluorine, hydrocarbyl or substituted hydrocarbyl;
R.sup.3 is hydrocarbyl, substituted hydrocarbyl, or oxysilyl; R.sup.4 is fluorine or perfluoroalkyl; and
R.sup.5 is hydrogen or fluorine; and provided that when R.sup.4 is fluorine, said temperature is 200.degree. C. to 400.degree. C.

### Claim 2 (depends on 1)

The process as recited in claim 1 wherein R.sup.1, R.sup.4 and R.sup.5 are fluorine, and R.sup.2 is perfluoroalkyl.

### Claim 3 (depends on 2)

The process as recited in claim 2 wherein R.sup.2 is perfluoro-n-alkyl.

### Claim 4 (depends on 1)

The process as recited in claim 1 wherein R.sup.4 and R.sup.5 are fluorine, and R.sup.1 and R.sup.2 are independently perfluoroalkyl.

### Claim 5 (depends on 1)

The process as recited in claim 1 wherein:
R.sup.1, R.sup.4 and R.sup.5 are fluorine and R.sup.2 is trifluoromethyl; or
R.sup.1, R.sup.2 and R.sup.5 are fluorine and R.sup.4 is trifluoromethyl.

### Claim 6 (depends on 1)

The process as recited in claim 1 wherein said temperature is about 220.degree. C. to about 300.degree. C.

### Claim 7 (depends on 5)

The process as recited in claim 5 wherein said temperature is about 220.degree. C. to about 300.degree. C.

### Claim 8 (depends on 1)

The process as recited in claim 1 wherein each R.sup.3 is alkyl containing 1 to 20 carbon atoms.

### Claim 9 (depends on 7)

The process as recited in claim 7 wherein each R.sup.3 is methyl.

### Claim 10 (depends on 7)

The process as recited in claim 7 wherein each R.sup.3 is alkyl containing 1 to 20 carbon atoms.

### Claim 11 (depends on 1)

The process as recited in claim 1 wherein said catalyst is an alkali metal fluoride.

### Claim 12 (depends on 11)

The process as recited in claim 11 wherein said alkali metal fluoride is potassium fluoride.

### Claim 13 (depends on 9)

The process as recited in claim 9 wherein said catalyst is potassium fluoride.

### Claim 14 (depends on 1)

The process as recited in claim 1 wherein:
R.sup.1 and R.sup.4 are fluorine, R.sup.2 is trifluoromethyl and R.sup.5 is hydrogen; or
R.sup.1 and R.sup.2 are fluorine, R.sup.4 is trifluoromethyl and R.sup.5 is hydrogen.

### Claim 15 (depends on 1)

The process as recited in claim 1 wherein a substituent is one or more of fluoro, ether, chloro, bromo, iodo, sulfonyl fluoride, nitrile, or perfluoroalkyl groups containing one or two hydrogen atoms.

### Claim 16 (depends on 1)

The process as recited in claim 1 wherein R.sup.1, R.sup.2 R.sup.4 and R.sup.5 are fluorine.