Method of producing nitrile compounds from ethylenically-unsaturated compounds
AssigneeRhodia Polyamide Intermediates
InventorsDamien Bourgeois, Jean-Christophe Gallard, Blaise Didillon, Philippe Marion
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Abstract
The present invention relates to a process for hydrocyanating a hydrocarbon-based compound containing at least one ethylenic unsaturation by reaction in liquid medium with hydrogen cyanide in the presence of a catalyst comprising a metal element chosen from transition metals and an organophosphorus ligand, characterized in that the organophosphorus ligand is a monodentate organophosphorus compound. The present invention is in particular useful for the synthesis of adiponitrile from butadiene.
Claims25
1-24. (canceled)
A process for hydrocyanating at a hydrocyanation reaction temperature a hydrocarbon-based compound containing at least one ethylenic unsaturation comprising the step of:
- a) reacting said compound in a liquid medium with hydrogen cyanide in the presence of a catalyst comprising a metallic element selected from transition metals and an organophosphorus ligand, wherein the organophosphorus ligand corresponds to general formula (I) below:
- wherein:
- X1 and X2, which are identical or different, represent an oxygen atom or the divalent radical NR2, wherein R2 represents a hydrogen atom, an alkyl, aryl, sulphonyl, cycloalkyl or carbonyl radical,
- X3 represents a covalent bond, an oxygen atom or the divalent radical NR2, wherein R2 represents a hydrogen atom, an alkyl, aryl, sulphonyl, cycloalkyl or carbonyl radical,
- the radical R1 represents a linear or branched alkyl radical having from 1 to 12 carbon atoms optionally having hetero atoms, or a substituted or unsubstituted aromatic or cycloaliphatic radical optionally having hetero atoms or one or more rings in fused or nonfused form, and
- L represents a linear or branched divalent alkyl radical having from 1 to 12 carbon atoms optionally having hetero atoms, or a substituted or unsubstituted aromatic or cycloaliphatic divalent radical optionally having hetero atoms and one or more rings in fused or nonfused form.
A process, for hydrocyanating an ethylenically unsaturated nitrile compound to dinitrile, comprising the step of reacting said nitrile with hydrogen cyanide, in the presence of a catalyst system comprising:
- at least one transition metal compound,
- at least one compound of formula (I) below:
- wherein:
- X1 and X2, which are identical or different, represent an oxygen atom or the divalent radical NR2, wherein R2 represents a hydrogen atom, an alkyl, aryl, sulphonyl, cycloalkyl or carbonyl radical,
- X3 represents a covalent bond, an oxygen atom or the divalent radical NR2, wherein R2 represents a hydrogen atom, an alkyl, aryl, sulphonyl, cycloalkyl or carbonyl radical,
- the radical R1 represents a linear or branched alkyl radical having from 1 to 12 carbon atoms optionally having hetero atoms, or a substituted or unsubstituted aromatic or cycloaliphatic radical optionally having hetero atoms or one or more rings in fused or nonfused form, and
- L represents a linear or branched divalent alkyl radical having from 1 to 12 carbon atoms optionally having hetero atoms, or a substituted or unsubstituted aromatic or cycloaliphatic divalent radical optionally having hetero atoms and one or more rings in fused or nonfused form, and
- a cocatalyst consisting of at least one Lewis acid.
Dependencies are inferred from the claim text.