1-Propanol → Propanal

Participants

Reaction Conditions

Reaction Steps

The autoclave was charged with 320 ml of a toluene solution containing 0.60 mmole of HRh(CO)(PPh3)3, 60 mmoles of triphenylphosphine and 0.525 mmole of trans-1,2-bis(diphenylphosphinomethyl)cyclobutane. The atmosphere in the autoclave was thoroughly purged with nitrogen gas and, then, with hydrogen/carbon monoxide (mol. ratio, 2:1) and the autoclave was heated to a constant temperature of 65° C. Then, a gaseous mixture of hydrogen and carbon monoxide (mol. ratio, 2:1) was introduced into the autoclave, and utilizing this gas, the internal pressure was controlled to 3.0 atmospheres (absolute pressure) and the flow rate of emergent gas to 20 Nl/hr. By means of a constant-speed pump, a total of 80 ml of allyl alcohol was introduced under stirring at the rate of 40 ml/hr. over a period of 2 hours. After the feed of allyl alcohol was terminated, the reaction was further continued for 2 hours. The emergent gas was thoroughly guided into a toluene trap cooled with dry ice-acetone and the accompanying allyl alcohol, propionaldehyde and other low-boiling products were thus collected in the above toluene trap. The hydroformylation of allyl alcohol was thus conducted at constant pressure and temperature for 4 hours. Gas chromatographic analysis of the reaction mixture and of the liquid in the toluene trap showed that there was 0.035 mmole of unreacted allyl alcohol (% conversion of allyl alcohol=97%). The yields of propionaldehyde, n-propanol, 2-methyl-3-hydroxy-propionaldehyde and 4-hydroxybutyraldehyde were 0.080 mole, 0.034 mole, 0.114 mole and 0.856 mole, respectively.

Provenance & Evidence