Reaktion #83004

ord-d4628cb5db4245138f2f75b0cd4d53b8

Reaktionsgleichung

C=CC1CO1
3,4-epoxy-1-butene
CCC(=O)OC(=O)CC
propionic anhydride
CCN(CC)CC
triethylamine
CCC(=O)O
propionic acid
C=CC(COC(=O)CC)OC(=O)CC
3,4-dipropionyloxy-1-butene
Ausbeute 90.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
125°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe autoclave was purged with helium twice
  2. 2
    Sonstigesequential samples were obtained every 15 min during the course of 2 hrs for analysis by GC

Vorschrift

A 100-mL autoclave was charged with 57.2 g (0.44 mol) propionic anhydride, 1.62 g (0.016 mol) of triethylamine, 1.2 g (0.016 mol) of propionic acid and 3.44 g of diglyme. The autoclave was purged with helium twice, then the vessel was pressurized to 6.2 bars (75 psig) with helium followed by agitation. The reaction mixture was heated to 125° C., then 31.35 mL (0.40 mol) of 3,4-epoxy-1-butene was introduced to the reactor via syringe pump over 10 seconds. A first sample was taken at 1 min, then sequential samples were obtained every 15 min during the course of 2 hrs for analysis by GC. GC analysis of the crude mixture after 2 hrs revealed a 90% yield of 3,4-dipropionyloxy-1-butene with a 91% selectivity and 6% 3,4-epoxy-1-butene. The reaction was observed to be first order in 3,4-epoxy-1-butene with a first order rate constant of 0.017 min-1 (Table A). This example shows the use of another carboxylic anhydride with its conjugate carboxylic acid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05623086uspto-grants-1997_04