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US 5,352,826 AGranted
Synthesis of acyl cyanides in an anhydrous reaction medium
AssigneeAtochem
InventorsMichel Devic, Pierre Tellier
Life of this patent
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Abstract
The acyl cyanides (nitriles), notably benzoyl cyanide, are prepared by reacting an acid halide with an alkali metal cyanide, in an anhydrous solvent medium, in the presence of an alkylene oxide compound and a polar compound other than water, e.g., glycerol, ethylene glycol, formamide or a sugar derivative.
Claims15
A process for the preparation of an acyl cyanide having the formula (I):
- ##STR8## 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):
- ##STR9## in which R is as defined above and X is a halogen atom, with an alkali metal cyanide, (a) in an inert anhydrous solvent medium, (b) in the presence of an acyl cyanide yield enhancing amount of a poly(alkylene oxide) compound and (c) in the further presence of a polar compound other than water, wherein the reactants are selected and used in amounts and under conditions which result in the production of said acyl cyanide.
A process for the preparation of an acyl cyanide having the formula (I):
- ##STR10## 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):
- ##STR11## in which R is as defined above and X is a halogen atom, with an alkali metal cyanide, (a) in an inert anhydrous solvent medium, (b) 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 (c) in the further presence of a polar compound other than water, wherein the reactants are selected and used in amounts and under conditions which result in the production of said acyl cyanide.
A process for the preparation of an acyl cyanide having the formula (I):
- ##STR12## 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):
- ##STR13## in which R is as defined above and X is a halogen atom, with an alkali metal cyanide, (a) in an inert anhydrous solvent medium, (b) in the presence of an acyl cyanide yield enhancing amount of a poly(alkylene oxide) compound containing one or more of the chains:
- --O--(CH.sub.2 --CH.sub.2 --O).sub.n --CH.sub.2 --CH.sub.2 --OH where n ranges from 2 to 200, and (c) in the further presence of a polar compound other than water, wherein the reactants are selected and used in amounts and under conditions which result in the production of said acyl cyanide.
Dependencies are inferred from the claim text.