Hydroformylation (Oxo) Catalysis

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Presentation transcript:

Hydroformylation (Oxo) Catalysis Daniell B. Kelly Department of Chemistry, Elmhurst College BACKGROUND Discovered by Otto Roelen in 1938 Cobalt catalysis dominated industrial hydroformylation until 1970’s  Rh CO Dissociation Uses: Plastics Detergents and surfactants Solvents Lubricants Chemical Intermediates 18e- HCo(CO)3 16e- anti-Markovnikov Hydride addition Reductive Elimination 18e- 18e- Oxidative H2 Addition 1,2 Insertion (reversing β elimination) 16e- 16e- Alkyl migration 18e- CO Add’n d (aldehyde) dt = k [alkene] [CO] [H2] [CO]-1 Rate: Back reactions are prevented with increased CO pressure. As a result, the alkene isomerization and opportunity to make a branched alkyl is limited.