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Homogeneous catalysis of the reppe reaction with iron pentacarbonyl: the production of propionaldehyde and 1-propanol from ethylene

Journal Article · · J. Am. Chem. Soc.; (United States)
DOI:https://doi.org/10.1021/ja00258a029· OSTI ID:5528020
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The Reppe hydroformylation of ethylene to produce propionaldehyde and 1-propanol in basic solutions containing Fe(CO)/sub 5/ as a catalyst has been studied under carefully controlled conditions at temperatures ranging from 110 to 140 /sup 0/C. Propionaldehyde is the principal product formed when NaOH is used as the base. The rate of reaction is found to increase with ethylene concentration and is second order with respect to Fe(CO)/sub 5/. The reaction is inhibited by CO. The increase in reaction rate with temperature corresponds to an activation energy of 31 kcal/mol. Infrared spectra indicate that HFe(CO)/sub 4/-and Fe(CO)/sub 5/ are present in the solution phase under reaction conditions. The experimental results are shown to be consistent with a mechanism in which the rate-determining step involves a binuclear iron carbonyl derivative. The substitution of (C/sub 2/H/sub 5/)/sub 3/N for NaOH facilitates the reduction of propionaldehyde to form 1-propanol but results in a slower rate for the overall reaction.

Research Organization:
Univ. of Georgia, Athens
DOE Contract Number:
AS09-76ER00933
OSTI ID:
5528020
Journal Information:
J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 109:24; ISSN JACSA
Country of Publication:
United States
Language:
English

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10 SYNTHETIC FUELS
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALCOHOLS
ALDEHYDES
ALKALI METAL COMPOUNDS
ALKENES
CARBON COMPOUNDS
CARBON MONOXIDE
CARBON OXIDES
CARBONYLATION
CARBONYLS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DATA
ENERGY
ETHYLENE
EXPERIMENTAL DATA
HIGH TEMPERATURE
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
HYDROXY COMPOUNDS
INFORMATION
INFRARED SPECTRA
IRON COMPOUNDS
KINETICS
MEDIUM TEMPERATURE
NUMERICAL DATA
ORGANIC COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PH VALUE
PROPANOLS
REACTION KINETICS
SODIUM COMPOUNDS
SODIUM HYDROXIDES
SPECTRA
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS