Formaldehyde → Methyl propionate

HRID 374329

Reaktionsgleichung

Reaktionsgleichung von HRID 374329
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CN=2)[CH:6]=CC=C[CH:2]=1.[C:20]1([CH3:30])C=CC(S(O)(=O)=[O:27])=C[CH:21]=1.N1C=CC=CC=1.[CH2:37]=[O:38].[CH3:39][OH:40]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:37][O:38][CH2:39][O:40][C:2](=[O:27])[CH2:1][CH3:6].[CH3:37][O:38][C:21](=[O:40])[CH2:20][CH3:30]

Komponenten

8

Edukt 5

HCID 712FormaldehydeHCID 887MethanolHCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 6218932-Pyridyldiphenylphosphine

Produkt 2

HCID 11124Methyl propionateHCID 11228781Methoxymethyl propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

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, 40 ml (500 mmol) pyridine, 20 ml methanol and 5 g paraformaldehyde. Air was then evacuated from autoclave, and then carbon monoxide (30 bar) and ethene (20 bar) were added. The autoclave was then sealed and heated to a temperature of 110° C. After a reaction time of 5 hours, a sample of the contents of the autoclave was withdrawn and analyzed by gas liquid chromatography. Two products were found; methoxymethylpropionate, which had been formed with a selectivity of 10%, and methylpropionate, which had been formed with a selectivity of 90%. The mean reaction rate was calculated to be 200 mol ethene/gram atom Pd/hour.

Aufarbeitung

  1. customAir was then evacuated from autoclave
  2. additioncarbon monoxide (30 bar) and ethene (20 bar) were added
  3. customThe autoclave was then sealed
  4. customAfter a reaction time of 5 hours, a sample of the contents of the autoclave was withdrawn

Quellen und Nachweise

ORD-Eintrag
ord-60c044af6ebe4e6db57b64cd9b21aca0
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166411

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