Acetic Acid → 3,4-Diacetoxy-1-butene

HRID 54723

Reaktionsgleichung

Reaktionsgleichung von HRID 54723
[O:1]1[CH2:5][CH:2]1[CH:3]=[CH2:4].[C:6]([O:9]C(=O)C)(=[O:8])[CH3:7].C(N(CC)CC)C.[C:20](O)(=[O:22])[CH3:21]>COCCOCCOC>[C:6]([O:9][CH:2]([CH2:5][O:1][C:20](=[O:22])[CH3:21])[CH:3]=[CH2:4])(=[O:8])[CH3:7]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13586Vinyloxirane

Produkt 1

HCID 27350013,4-Diacetoxy-1-buteneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A 300-mL autoclave was charged with 40 mL (0.50 mol) of 3,4-epoxy-1-butene, 62.2 g (0.61 mol) acetic anhydride, 1.8 g (0.018 mol) of triethylamine, 1.1 g (0.018 mol) acetic acid and 4.2 mL of diglyme. The autoclave was purged with nitrogen twice, then the vessel was pressurized to 8 bars (100 psig) with nitrogen. The agitator was started and an initial sample was taken. The mixture was heated to 125° C. During the course of 2 hrs, samples were taken every 15 min for analysis by GC. GC analysis of the crude mixture after 2 hrs revealed an 87% yield of 3,4-diacetoxy-1-butene with an 89% selectivity and 1.8% 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 0.024 min-1 (Table A). This example demonstrates the catalytic effect of the tertiary amine with acetic acid as the co-catalyst (Table B).

Aufarbeitung

  1. customThe autoclave was purged with nitrogen twice
  2. waitGC analysis of the crude mixture after 2 hrs revealed

Quellen und Nachweise

ORD-Eintrag
ord-d73b0011b14e4e15af10182136028344
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623086

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