1-Propanol → Propanal

HRID 1659979

Reaktionsgleichung

Reaktionsgleichung von HRID 1659979
C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C[C@@H]2CC[C@H]2CP(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:59]([OH:62])[CH:60]=[CH2:61].[CH2:63]([OH:66])[CH2:64][CH3:65]>>[CH:59](=[O:62])[CH2:60][CH3:61].[CH3:65][CH:64]([CH2:59][OH:62])[CH:63]=[O:66].[OH:62][CH2:59][CH2:60][CH2:61][CH:63]=[O:66]

Komponenten

8

Edukt 5

HCID 10311-PropanolHCID 1140TolueneHCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 12635846HCID 12635846, Verbindung

Produkt 3

HCID 527PropanalHCID 930934-HydroxybutanalHCID 110297623-Hydroxy-2-methylpropanal

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe atmosphere in the autoclave was thoroughly purged with nitrogen gas
  2. additionThen, a gaseous mixture of hydrogen and carbon monoxide (mol. ratio, 2:1)
  3. additionwas introduced into the autoclave
  4. additionBy means of a constant-speed pump, a total of 80 ml of allyl alcohol was introduced
  5. customAfter the feed of allyl alcohol was terminated
  6. waitthe reaction was further continued for 2 hours
  7. customThe emergent gas was thoroughly guided into a toluene trap
  8. temperaturecooled with dry ice-acetone
  9. customthe accompanying allyl alcohol, propionaldehyde and other low-boiling products were thus collected in the above toluene trap
  10. waitThe hydroformylation of allyl alcohol was thus conducted at constant pressure and temperature for 4 hours

Quellen und Nachweise

ORD-Eintrag
ord-bdb071141a72422fb18e05924477f83b
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04306087

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