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US 6,191,300 B1Granted
Process for the preparation of cyclopropylacetonitrile
AssigneeEastman Chemical Company
InventorJohn Anthony Hyatt
Life of this patent
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Abstract
Disclosed is a process for the preparation and recovery of cyclopropylacetonitrile by a novel combination of process steps beginning with a mixture of cyclopropylmethyl halide, a cyclobutyl halide and a 4-halo-1-butene. The process permits the recovery of substantially pure cyclopropylacetonitrile and cyclobutyl halide, e.g., cyclopropylacetonitrile and cyclobutyl halide each having a purity greater than about 95%.
Claims5
Process for the preparation of cyclopropylacetonitrile by the steps comprising:
- (1) contacting a reactant mixture comprising a cyclopropylmethyl halide, a cyclobutyl halide and a 4-halo-1-butene with an aqueous solution of an alkali metal cyanide in the presence of a phase transfer catalyst to obtain a reaction mixture comprising (i) an organic phase comprising cyclopropylacetonitrile, cyclobutyl halide, 1-cyano-3-butene and phase transfer catalyst and (ii) an aqueous phase comprising a solution of the alkali metal halide and cyanide and phase transfer catalyst;
- (2) separating organic phase (i) from aqueous phase (ii) from step (1);
- (3) contacting organic phase (i) from step (2) with elemental halogen to obtain a reaction mixture comprising cyclopropylacetonitrile, cyclobutyl halide, 4-cyano-1,2-butane dihalide and phase transfer catalyst;
- and
- (4) subjecting the reaction mixture of step (3) to fractional distillation to obtain overhead vapor products comprising cyclopropylacetonitrile and cyclobutyl halide and a distillation base residues comprising 4-cyano-1,2-butane dihalide and phase transfer catalyst.
2 more elements
A process for the preparation of cyclopropylacetonitrile by the steps comprising:
- (1) contacting a reactant mixture comprising cyclopropylmethyl bromide, cyclobutyl bromide and 4-bromo-1-butene (bromobutene) with an aqueous solution of an alkali metal cyanide in the presence of a phase transfer catalyst to obtain a reaction mixture comprising (i) an organic phase comprising cyclopropylacetonitrile, cyclobutyl bromide, 1-cyano-3-butene and phase transfer catalyst and (ii) an aqueous phase comprising a solution of the alkali metal halide and cyanide and phase transfer catalyst;
- (2) separating organic phase (i) from aqueous phase (ii) from step (1);
- (3) contacting organic phase (i) from step (2) with elemental bromine to obtain a reaction mixture comprising cyclopropylacetonitrile, cyclobutyl bromide, 4-cyano-1,2-butane dibromide and phase transfer catalyst;
- and (4) subjecting the reaction mixture of step (3) to fractional distillation to obtain overhead vapor products comprising cyclopropylacetonitrile and cyclobutyl bromide and a distillation base residues comprising 4-cyano-1,2-butane dibromide and phase transfer catalyst.
1 more element
Dependencies are inferred from the claim text.