# US 5,352,827 A · Synthesis of acyl cyanides in a hydrous reaction medium

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- Number: US 5,352,827 A
- Document ID: US5352827A
- Status: Granted
- Kind: A
- Application number: 08/035,894
- Filed: 1993-03-23
- Granted: 1994-10-04
- Earliest claimed: 1989-05-19
- Assignees: Atochem
- Inventors: Michel Devic; Pierre Tellier
- Web page: https://patentgrep.com/patent/US5352827A

## CPC

- C07C 253/14: by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The acyl cyanides (nitriles) are prepared by reacting an acid halide with an alkali metal cyanide, in the presence of an alkylene oxide compound and a catalytically effective amount of water.

## Claims

### Claim 1

A process for the preparation of an acyl cyanide having the formula (I): ##STR11## in which R is an alkyl radical having from 1 to 8 carbon atoms, a cycloalkyl radical having from 3 to 12 carbon atoms, an aryl radical, a heterocyclic radical optionally condensed with a benzene nucleus, or substituted such radicals, comprising reacting in the liquid phase an acid halide of the formula (II): ##STR12## in which R is as defined above and X is a halogen atom, with an alkali metal cyanide in the presence of an acyl cyanide yield enhancing amount of a poly(alkylene oxide) compound and a catalytically effective amount of water, wherein the reactants are selected and used in amounts and under conditions which result in the production of said acyl cyanide.

### Claim 2 (depends on 1)

The process as defined by claim 1, carried out in the presence of a solvent medium.

### Claim 3 (depends on 1)

The process as defined by claim 1, wherein the amount of alkali metal cyanide ranges from 1 to 2 moles per mole of acid halide.

### Claim 4 (depends on 3)

The process as defined by claim 3, said amount of alkali metal cyanide ranging from 1 to 1.25 moles per mole of acid halide.

### Claim 5 (depends on 1)

The process as defined by claim 1, said alkali metal cyanide comprising sodium cyanide.

### Claim 6 (depends on 2)

The process as defined by claim 2, said solvent medium comprising xylene or toluene.

### Claim 7 (depends on 1)

The process as defined by claim 1, wherein the amount of said alkylene oxide compound ranges from 0.1 to 10 g per mole of acid halide.

### Claim 8 (depends on 7)

The process as defined by claim 7, said amount of alkylene oxide compound ranging from 0.4 to 2 g per mole of acid halide.

### Claim 9 (depends on 1)

The process as defined by claim 1, said catalytically effective amount of water ranging from 0.2 to 2 g per mole of acid halide.

### Claim 10 (depends on 9)

The process as defined by claim 9, said catalytically effective amount of water ranging from 0.5 to 1 g per mole of acid halide.

### Claim 11 (depends on 1)

The process as defined by claim 1, said acid halide comprising benzoyl chloride.

### Claim 12 (depends on 2)

The process as defined by claim 2, wherein the amount of solvent ranges from 150 to 500 ml per mole of acid halide.

### Claim 13

A process for the preparation of an acyl cyanide having the formula (I): ##STR13## in which R is an alkyl radical having from 1 to 8 carbon atoms, a cycloalkyl radical having from 3 to 12 carbon atoms, an aryl radical, a heterocyclic radical optionally condensed with a benzene nucleus, or substituted such radicals, comprising reacting in the liquid phase an acid halide of the formula (II): ##STR14## in which R is as defined above and X is a halogen atom, with an alkali metal cyanide, in the presence of an acyl cyanide yield enhancing amount of a poly(alkylene oxide) compound containing 2 to 200 ethylene oxide or propylene oxide recurring units, or combination thereof and a catalytically effective amount of water, wherein reactants are selected and used in amounts and under conditions which result in the production of said acyl cyanide.

### Claim 14

A process for the preparation of an acyl cyanide having the formula (I): ##STR15## in which R is an alkyl radical having from 1 to 8 carbon atoms, a cycloalkyl radical having from 3 to 12 carbon atoms, an aryl radical, a heterocyclic radical optionally condensed with a benzene nucleus, or substituted such radicals, comprising reacting in the liquid phase an acid halide of the formula (II): ##STR16## in which R is as defined above and X is a halogen atom, with an alkali metal cyanide, in the presence of an acyl yield enhancing amount of a poly(alkylene oxide) compound containing one or more of the chains: --O--(CH.sub.2 --CH.sub.2 --O)n--CH.sub.2 --CH.sub.2 --OH where n ranges from 2 to 200, and a catalytically effective amount of water, wherein the reactants are selected and used in amounts and under conditions which result in the production of said acyl cyanide.

### Claim 15 (depends on 1)

The process as defined in claim 1, wherein said acyl halide is reacted with said alkali metal cyanide in the further presence of an inert solvent wherein said inert solvent is not said alkylene oxide compound.