# US 5,345,017 A · Process for reducing the fluorine content of halocarbons

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- Number: US 5,345,017 A
- Document ID: US5345017A
- Status: Granted
- Kind: A
- Application number: 08/148,032
- Filed: 1993-11-05
- Granted: 1994-09-06
- Earliest claimed: 1992-12-08
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: V. N. Mallikarjuna Rao; Steven H. Swearingen
- Web page: https://patentgrep.com/patent/US5345017A

## CPC

- C07C 17/206: {the other compound being HX}
- C07C 17/00: Preparation of halogenated hydrocarbons
- C07C 17/204: {the other compound being a halogen}
- C07C 17/358: by isomerisation
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The fluorine content of an acyclic saturated compound of the formula C.sub.n F.sub.a X.sub.b having at least one carbon with at least two fluorine substituents (wherein each X is independently selected from Cl and Br, and wherein n is 1 to 4, a is 2 to 10, b is 0 to 8, and a+b equals 2n+2) is reduced by reacting the acyclic saturated compound with HCl in the vapor phase at an elevated temperature in the presence of a catalyst, the mole ratio of HCl to the acyclic saturated compound being at least about 2:1.

## Claims

### Claim 1

A method for reducing the fluorine content of an acyclic saturated compound of the formula C.sub.n F.sub.a X.sub.b wherein each X is independently selected from the group consisting of chlorine and bromine, wherein n is 1 to 4, a is 2 to 10, b is 0 to 8, and a+b equals 2n+2, and wherein the acyclic saturated compound has at least one carbon with at least two fluorine substituents, comprising the step of:
reacting said acyclic saturated compound with HCl in the vapor phase at a temperature in the range of from about 250.degree. C. to 550.degree. C. in the presence of a catalyst, the mole ratio of HCl to said acyclic saturated compound being at least about 2:1.

### Claim 2 (depends on 1)

The method of claim 1 wherein the catalyst comprises aluminum fluoride.

### Claim 3 (depends on 1)

The method of claim 1 wherein the catalyst comprises chromium oxide.

### Claim 4 (depends on 1)

The method of claim 1 wherein the catalyst is selected from alumina, fluorided alumina, magnesium fluoride on aluminum fluoride, alumina on carbon, aluminum fluoride on carbon and fluorided alumina on carbon.

### Claim 5 (depends on 1)

The method of claim 1 wherein the catalyst comprises a metal selected from the group consisting of chromium, zinc, Group VIII metals, Group VIIB metals, Group IIIB metals, Group IB metals, and metals having an atomic number of 58 through 71.

### Claim 6 (depends on 5)

The method of claim 5 wherein the metal is on alumina, aluminum fluoride, fluorided alumina on carbon; and wherein the total metal content is from about 0.1 to 20 percent by weight.

### Claim 7 (depends on 1)

The method of claim 1 wherein a compound with only one less fluorine is produced.

### Claim 8 (depends on 1)

The method of claim 1 wherein the compound CCl.sub.2 FCF.sub.3 is reacted with HCl to provide CCl.sub.3 CF.sub.3, and is prepared by isomerizing CClF.sub.2 CClF.sub.2.

### Claim 9 (depends on 1)

The method of claim 1 wherein the acyclic saturated compound is selected from the group consisting of CCl.sub.2 CF.sub.2, CClF.sub.3, CCl.sub.2 FCClF.sub.2, CCl.sub.3 CF.sub.3, CClF.sub.2 CClF.sub.2, CClF.sub.2 CF.sub.3, CCl.sub.2 FCF.sub.3, and CBrF.sub.3.

### Claim 10 (depends on 1)

The method of claim 1 wherein n is at least 2 and b is at least one.

### Claim 11 (depends on 1)

The method of claim 1 wherein C.sub.2 Cl.sub.2 F.sub.4 is reacted with HCl.

### Claim 12 (depends on 1)

The method of claim 1 wherein the compound CCl.sub.3 CF.sub.3 is reacted with HCl to provide CCl.sub.3 CClF.sub.2, and is prepared by isomerizing CCl.sub.2 FCClF.sub.2.

### Claim 13

A process for reducing the fluorine content of a chlorofluoroethane consisting of carbon, chlorine and fluorine and having at least one carbon with at least two fluorine substituents, comprising the steps of:
reacting said chlorofluoroethane with a fluorine-reducing reagent consisting essentially of HCl in the vapor phase at a temperature in the range of from about 300.degree. C. to 450.degree. C. in the presence of a catalyst comprising aluminum fluoride to produce Cl.sub.2 C.dbd.CCl.sub.2, the mole ratio of HCl to said chlorofluoroethane being at least about 5:1.

### Claim 14 (depends on 13)

The process of claim 13 wherein the chlorofluoroethane is a dichloroetrafluoroethane.

### Claim 15 (depends on 13)

The process of claim 13 wherein the chlorofluoroethane is a trichlorotrifluoroethane.

### Claim 16 (depends on 13)

The process of claim 13 wherein the chlorofluoroethane is chloropentafluoroethane.

### Claim 17

A process for reducing the fluorine content of an acyclic saturated compound of the formula C.sub.n F.sub.a wherein n is 1 to 4, and a equals 2n+2 comprising the step of:
reacting said acyclic saturated compound with HCl in the vapor phase at a temperature in the range of from about 250.degree. to 550.degree. C. in the presence of a chromium oxide catalyst, the mole ratio of HCl to said acyclic saturated compound being at least about 5:1.

### Claim 18 (depends on 17)

The process of claim 17 wherein the acyclic saturated compound is CF.sub.3 CF.sub.2 CF.sub.3.

### Claim 19 (depends on 18)

The process of claim 18 wherein the reaction temperature is about 500.degree. C. and a 12.2% conversion to chlorofluoropropanes is reached.

### Claim 20 (depends on 1)

The method of claim 1 wherein said acyclic saturated compound is reacted with a fluorine-reducing reagent consisting essentially of said HCl.