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4571-chapt16-hydroformylation

4571-chapt16-hydroformylation - Hydroformylation 1...

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Hydroformylation 1 Hydroformylation (Oxo) Catalysis + CO + H 2 H O + O H linear (normal) branched (iso) Rh or Co R R R Aldehydes R alkene isomerization alkene hydrogenation R side reactions * * Largest homogeneous catalytic process * > 15 billion pounds of aldehydes (alcohols) per year * Commercial catalysts are complexes of Co or Rh * Selectivity to linear (normal) or branched (iso) products is important Hydroformylation was discovered by Otto Roelen in 1938 during an investigation of the origin of oxygenated products occurring in cobalt catalyzed Fischer-Tropsch reactions. Roelen's observation that ethylene, H 2 and CO were converted into propanal, and at higher pressures, diethyl ketone, marked the beginning of hydroformylation. Cobalt catalysts completely dominated industrial hydroformylation until the early 1970's when rhodium catalysts were commercialized. In 2004, ~75% of all hydroformylation processes are based on rhodium triarylphosphine catalysts, which excel with C 8 or lower alkenes and where high regioselectivity to linear aldehydes is critical. Most aldehydes produced are hydrogenated to alcohols or oxidized to carboxylic acids. Esterfication of the alcohols with phthalic anhydride produces dialkyl phthalate plasticizers that are primarily used for polyvinyl chloride plastics -- the Otto Roelen (1897-1993)
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