Propionic Acid → Propionic anhydride

HRID 653813Notes

Reaction equation

HRID 653813 reaction equation
C1(P([C:14]2[CH:19]=[CH:18]C=CC=2)C2C=CC=CN=2)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=[O:27])=CC=1.[C:31]([OH:35])(=[O:34])[CH2:32][CH3:33]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N)CCC>[C:31]([O:35][C:14](=[O:27])[CH2:19][CH3:18])(=[O:34])[CH2:32][CH3:33]

Participants

6

Reactant 3

HCID 1032Propionic AcidHCID 6101p-Toluenesulfonic acidHCID 6218932-Pyridyldiphenylphosphine

Product 1

HCID 31263Propionic anhydride

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8007ButylamineSolvent

Conditions

Temperature
110 °C

Procedure

A 250 ml stainless steel, magnetically stirred autoclave was filled with 0.1 mmol palladium(II) acetate, 5 mmol bisphenyl(2-pyridyl)phosphine, 4 mmol p-toluenesulfonic acid, 50 ml propionic acid and 10 ml n-butylamine. Air was then evacuated from the autoclave. The autoclave was then pressurized with 30 bar carbon monoxide and 20 bar ethene, sealed and heated to 110° C. After 11/2 hours reaction time, a sample of the contents of the autoclave was withdrawn and analyzed by gas-liquid chromatography. The analysis revealed that N-butyl propionamide had been formed with a selectivity (based on amine) of >95%, together with propionic anhydride. The mean conversion rate was calculated to be 1,500 moles ethene/gram atom Pd/hour.

Workup

  1. customAir was then evacuated from the autoclave
  2. customsealed
  3. customAfter 11/2 hours reaction time
  4. customa sample of the contents of the autoclave was withdrawn

Sources & evidence

ORD record
ord-5b9af5dcaea641faa8edc068399badbb
Source dataset
uspto-grants-1992_07
Patent number
US05128475

Reaction notes

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