Hydroformylation

Olefin hydroformylation was one of the first homogeneous chemocatalysis reactions to be performed on an industrial scale. The early catalysts were based on cobalt, and the first large-scale process was practiced by Ruhrchemie. Union Carbide commercialized a rhodium-triphenylphosphine catalyst in 1975 for the production of butyraldehyde and ultimately n-butanol from propylene. A range of products is now manufactured using hydroformylation, and it is the largest volume homogeneous transition metal-catalyzed reaction used today. Contrastingly, asymmetric olefin hydroformylation has not been used on an industrial scale, but has the potential to provide concise routes to a wide range of chiral molecules.

Dowpharma^SM has developed an extensive library of ligands for asymmetric hydroformylation, which have been screened against styrene, vinyl acetate and allyl cyanide substrates using high throughput methods. This led to the rapid identification of a new phosphite ligand, "Kelliphite," providing excellent enantiomeric control and exceptional branched-to-linear ratios, far exceeding ligand systems previously reported. Research into asymmetric hydroformylation is continuing, and we are in a good position to scale-up commercial processes using Dow’s extensive manufacturing capabilities and experience.

For more information:
4/03 Dowpharma Announces New Capabilities in Asymmetric Hydroformylation for Pharmaceutical Applications

Asymmetric Hydroformylation – New Developments in Asymmetric Hydrofomylation (249KB PDF)

Optically active 3,4-diazaphospholane ligands and their application in asymmetric hydroformylation and allylic alkylation reactions (perspective) (477KB PDF)

Hydroaminomethylation
In addition to developing new catalysts for asymmetric hydroformylation, Dowpharma has been applying hydroformylation to the synthesis of achiral molecules. We have access to a wide range of catalysts that provide extremely high linear selectivity (>40:1) and the resulting aldehyde can be reductively aminated in situ. In our synthesis of Ibutilide the hydroaminomethylation is performed without protection of the alcohol. Many other applications of this technology are currently being developed.

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