Bidentate ligands for hydroformylation of ethylene

A process for the hydroformylation of ethylene with a transition metal catalyst promoted with a bidentate ligand of Formula I, II and III:

• in which both R1 and R8 are hydrogen or a hydrocarbyl group of C1 to C4;
• R2-R7 and R9-R24 are independently a hydrogen, a hydrocarbyl group, an aromatic ring, a heteroaromatic ring or a halogen atom, or a heterocarbyl group selected from the groups consisting of NR2, OR and SR, where R is a hydrocarbyl group of C1 to C20, or heterohydrocarbyl group having 1 to 20 atoms, each independently selected from C or a heteroatom, wherein each heteroatom is independently O, S, Si, Ge, P, or N, and may themselves be substituted or unsubstituted as required by the valency of the heteroatom, R2-R7 and R9-R24 may optionally comprise cycloaliphatic or aryl groups fused to the biaryl moiety such as:
• for Formula I, II, or III, each aryl, heteroaryl, hydrocarbyl, heterohydrocarbyl, hydrocarbylene, and heterohydrocarbylene group independently is unsubstituted or substituted with one or more substituents Rv each independently a halogen atom, polyfluoroalkyl substitution, unsubstituted C1 to C18 alkyl, F3C—, F2HCO—, F3CO—, R3Si, R3Ge, RO, RS, RS(O), RS(O)2, R2P, R2N, R2C═N, NC, RC(O)O, ROC(O), RC(O)N(R), or R2NC(O), or two of the Rv are taken together to form an un unsubstituted C1 to C18 alkylene, wherein each R independently is an unsubstituted C1 to C18 alkyl,
• X1 is CH2 or O, while X2 is O or C(R25)2, and each R25 may be the same or different and is a hydrogen, a cycloaliphatic group, an aromatic ring, a heteroaromatic ring or a halogen atom, or a heterocarbyl group selected from the groups consisting of NR2, OR and SR, where R is a hydrocarbyl group of C1 to C20, or a heterohydrocarbyl group having 1 to 20 atoms, each independently selected from C or a heteroatom, wherein each heteroatom is independently O, S, Si, Ge, P, or N, and may themselves be substituted or unsubstituted as required by the valency of the heteroatom, wherein two R25 groups may combine in a fused ring, and
• Y is a pyrrole group bound via the nitrogen atom to phosphorus, wherein each pyrrole group may bear multiple substituents selected from among the groups alkyl, alkoxy, acyl, carboxyl, carboxylate, cyano, —SO3H, sulfonate, amino, trifluoromethyl and halogen;
• wherein the process has a turnover frequency of 0.0118 hr−1 or greater.