Gamma-Butyrolactone → Butanal

HRID 2420357Notes

Reaction equation

HRID 2420357 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
88 °C

Procedure

The following experiments illustrate the effect of water on the reaction rate and product distribution. Into a 1/2 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 42 atmospheres. The autoclave was heated to 88° C. 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 42 atmospheres
  6. temperaturemaintained at that temperature for 6 minutes
  7. temperaturecooled
  8. distillationThe liquid products were distilled

Sources & evidence

ORD record
ord-f965cac568e74357b3ffd37b8a9a7487
Source dataset
uspto-grants-1978_08
Patent number
US04110404

Reaction notes

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