Method for making nitrile compounds from ethylenically unsaturated compounds

A process for hydrocyanating a hydrocarbon compound containing at least one ethylenic unsaturation by reacting it in a liquid medium with hydrogen cyanide in the presence of a catalyst comprising a metallic element selected from transition metals and an organic ligand, wherein the organic ligand corresponds to the general formula I below:

• in which:
• T and T1, which are identical or different, represent a phosphorus, arsenic or antimony atom,
• R1, R2, R3 and R4, which are identical or different, represent a substituted or unsubstituted, aromatic, aliphatic or cycloaliphatic radical having one or more rings, which are in fused form or not, optionally having one or more heteroatoms, wherein the radicals R1 and R2 on the one hand and R3 and R4 on the other hand are optionally interconnected by a covalent bond, a hydrocarbon chain or a heteroatom,
• U1, U2, U3 and U4, which are identical or different, represent an oxygen atom or a radical of formula NR in which R denotes a monovalent alkyl, aryl, cycloalkyl, sulphonyl or carbonyl radical,
• R5 and R6, which are identical or different, represent an aryl or cycloaliphatic group optionally having heteroatoms and/or one or more rings, in fused form or not, and which are substituted or unsubstituted,
• n is an integer equal to 0 or 1,
• L1, when n is 0, represents a divalent radical selected from the group consisting of the groups NR7, PR8, SiR9R10, BR11, S, POR12, SO2 and CO, in which R7 is as defined for R above, R8 and R12 optionally represent the radical OR13, and R8, R9, R10, R11, R12 and R13 represent alkyl, aryl or cycloalkyl radicals,
• L1 and L2, when n is 1, are identical or different and represent a covalent bond or a radical selected from the group consisting of the groups O, NR7, PR8, SiR9R10, BR11, S, POR12, SO2, CO and —CR14R15—, in which R7 is as defined for R above, R8 and R12 optionally represent the radical OR13, and R8, R9, R10, R11, R12, R13 R14 and R15 represent alkyl, aryl or cycloalkyl radicals, it being possible also for R14 and R15 to represent a hydrogen atom.

Organophosphorus compounds corresponding to the general formula I below:

• in which:
• T and T1, which are identical or different, represent a phosphorus, arsenic or antimony atom,
• R1, R2, R3 and R4, which are identical or different, represent a substituted or unsubstituted, aromatic, aliphatic or cycloaliphatic radical having one or more rings, which are in fused form or not and optionally contain one or more heteroatoms,
• wherein the radicals R1 and R2 on the one hand and R3 and R4 on the other hand optionally be interconnected by a covalent bond, a hydrocarbon chain or a heteroatom,
• U1, U2, U3 and U4, which are identical or different, represent an oxygen atom or a radical of formula NR in which R denotes a monovalent alkyl, aryl, cycloalkyl, sulphonyl or carbonyl radical,
• R5 and R6, which are identical or different, represent an aryl or cycloaliphatic group optionally comprise heteroatoms and/or one or more rings, in fused form or not, and which are substituted or unsubstituted,
• n is an integer equal to 0 or 1,
• L1, when n is 0, represents a divalent radical selected from the group consisting of the groups NR7, PR8, SiR9R10, BR11, S, POR12, SO2 and CO, in which R7 is as defined for R above, R8 and R12 may represent the radical OR13, and R8, R9, R10, R11, R12 and R13 represent alkyl, aryl or cycloalkyl radicals,
• L1 and L2, when n is 1, are identical or different and represent a covalent bond or a radical selected from the group consisting of the groups O, NR7, PR8, SiR9R10, BR11, S, POR12, SO2, CO and —CR14R15—, in which R7 is as defined for R above, R8 and R12 optionally represent the radical OR13, and R8, R9, R10, R11, R12, R13, R14 and R15 represent alkyl, aryl or cycloalkyl radicals, it being possible also for R14 and R15 to represent a hydrogen atom.