Gamma-Butyrolactone → Butanal

HRID 2286768Notes

Reaction equation

HRID 2286768 reaction equation
[C:1]1(=O)[O:5][CH2:4][CH2:3][CH2:2]1.N12CCN(CC1)CC2.C1(P([C:28]2[CH:33]=[CH:32]C=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Rh](Cl)(Cl)Cl.O>[CH:4](=[O:5])[CH2:3][CH2:2][CH3:1].[CH:4](=[O:5])[CH:33]([CH3:32])[CH3:28]

Participants

7

Reactant 3

HCID 7302Gamma-ButyrolactoneHCID 9237DabcoHCID 11776Triphenylphosphine

Product 2

HCID 261ButanalHCID 6561Isobutyraldehyde

Reagents, catalysts & solvents 2

HCID 24872Rhodium chlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
190 fahrenheit

Procedure

The following experiments illustrate the effect of water on the reaction rate and product distribution. Into a one-half gallon autoclave was charged 300 grams butyrolactone, 50 grams water, 2 grams 1,4-diazabicyclo(2.2.2)octane, 2 grams triphenylphosphine and 0.4 gram rhodium chloride. The autoclave was closed, purged with nitrogen and 104 grams of propylene were introduced. Thereafter equal volumes of carbon monoxide followed by hydrogen were introduced to raise the pressure 600 psi. The autoclave was heated to 190° F. and maintained at that temperature for 6 minutes, then cooled, depressured and opened. The liquid products were distilled to obtain 90.5 grams normal butyraldehyde and 21.7 grams isobutyraldehyde (ratio of 4.17).

Workup

  1. customThe autoclave was closed
  2. custompurged with nitrogen and 104 grams of propylene
  3. additionwere introduced
  4. additionwere introduced
  5. temperatureto raise the pressure 600 psi
  6. temperaturemaintained at that temperature for 6 minutes
  7. temperaturecooled
  8. distillationThe liquid products were distilled

Sources & evidence

ORD record
ord-855cb91a04fe42d6acde04782cd50f22
Source dataset
uspto-grants-1981_05
Patent number
US04267383

Reaction notes

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