# US 4,400,566 A · Reduction of organic halides

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

- Number: US 4,400,566 A
- Document ID: US4400566A
- Status: Granted
- Kind: A
- Application number: 06/361,192
- Filed: 1982-03-24
- Granted: 1983-08-23
- Earliest claimed: 1980-10-21
- Assignees: Union Carbide Corporation
- Inventors: Ismael Colon
- Web page: https://patentgrep.com/patent/US4400566A

## CPC

- A62D 3/37: by reduction, e.g. hydrogenation
- C07C 1/26: starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C 41/24: by elimination of halogens, e.g. elimination of HCl
- C07C 255/00: Carboxylic acid nitriles (cyanogen or compounds thereof C01C3/00)
- A62D 2101/22: containing halogen
- C07C 2531/24: Phosphines
- C07C 2531/26: containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
- A62D: CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Organic halides are reduced to a dechlorinated products with a catalyst mixture consisting essentially of a nickel compound, a triarylphosphine and a halide ion, in the presence of reducing means for maintaining nickel in the zero valent state.

## Claims

### Claim 1

Method of reducing organic halides free of nitro substituents which comprises contacting said organic halides in a solvent under an inert atmosphere with a catalytic amount of a catalytic mixture consisting essentially of:
(1) a nickel compound containing no radicals in which N and O are bonded directly to each other; and
(2) a triarylphosphine having 6 to about 24 carbons in each aryl moiety, in the presence of reducing means for maintaining nickel in the zero valence state, at a temperature of up about 250.degree. C., wherein the ratio of triarylphosphine to nickel is at least about 0.1.

### Claim 2 (depends on 1)

Method claimed in claim 1 wherein the reducing means is a metal with a greater reduction potential than nickel.

### Claim 3 (depends on 2)

Method claimed in claim 2 wherein the metal is aluminum.

### Claim 4 (depends on 2)

Method claimed in claim 2 wherein the metal is calcium.

### Claim 5 (depends on 2)

Method claimed in claim 2 wherein the metal is magnesium.

### Claim 6 (depends on 2)

Method claimed in claim 2 wherein the metal is zinc, the catalyst contains a halide ion wherein the ratio of gram atoms of halide ion to nickel is at least about 0.1 and the solvent contains at least one protic solvent.

### Claim 7 (depends on 1)

Method claimed in claim 1 wherein the nickel compound is nickel chloride.

### Claim 8 (depends on 1)

Method claimed in claim 1 wherein the triarylphosphine is triphenyl phosphine.

### Claim 9 (depends on 6)

Method claimed in claim 6 wherein the halide ion is an iodide.

### Claim 10 (depends on 6)

Method claimed in claim 6 wherein the halide ion is bromide ion.

### Claim 11 (depends on 6)

Method claimed in claim 6 wherein the solvent is a mixture of a protic solvent and an aprotic solvent.

### Claim 12 (depends on 11)

Method claimed in claim 11 wherein the protic solvent is water.

### Claim 13 (depends on 11)

Method claimed in claim 11 wherein the aprotic solvent is dimethylformamide.

### Claim 14 (depends on 11)

Method claimed in claim 11 wherein the protic solvent is an aliphatic alcohol containing 1 to about 10 carbons.

### Claim 15 (depends on 14)

Method claimed in claim 14 wherein the aliphatic alcohol is methanol.

### Claim 16 (depends on 1)

Method claimed in claim 1 wherein the organic halide is an aryl halide.

### Claim 17 (depends on 16)

Method claimed in claim 16 wherein the aryl halide is an aryl chloride.

### Claim 18 (depends on 1)

Method claimed in claim 1 wherein the organic halide is an arylalkyl halide.

### Claim 19 (depends on 1)

Method claimed in claim 1 wherein the organic halide is a cycloaliphatic halide.

### Claim 20 (depends on 1)

Method claimed in claim 1 wherein the organic halide is a polychlorinated arene.

### Claim 21 (depends on 20)

Method claimed in claim 20 wherein the polychlorinated arene is 1,2,4,-trichlorobenzene.

### Claim 22 (depends on 20)

Method claimed in claim 20 wherein the polychlorinated arene is a mixture of chlorinated biphenyls.