Acetic Acid → 3,4-Diacetoxy-1-butene

HRID 54728

Reaktionsgleichung

Reaktionsgleichung von HRID 54728
[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 13586Vinyloxirane2×

Produkt 1

HCID 27350013,4-Diacetoxy-1-buteneAusbeute 96 %

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, 56.2 g (0.55 mol) acetic anhydride, 2.0 g (0.02 mol ) of triethylamine, 3.6 g (0.06 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. Then the mixture was heated to 125° C. During the course of 2.5 hrs, samples were obtained every 15 min for analysis by GC. GC analysis of the crude mixture after 2.5 hrs revealed a 96% yield of 3,4-diacetoxy-1-butene and 1.4% 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 0.037 min-1 (Table A). This example demonstrates the catalytic effect of a tertiary amine with three molar equivalents of acetic acid (Table B).

Aufarbeitung

  1. customThe autoclave was purged with nitrogen twice
  2. customDuring the course of 2.5 hrs, samples were obtained every 15 min for analysis by GC

Quellen und Nachweise

ORD-Eintrag
ord-ca47668524a7466ebbc86aa56b1ea08f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623086

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