Acetic Acid → 3,4-Diacetoxy-1-butene

HRID 54727

Reaktionsgleichung

Reaktionsgleichung von HRID 54727
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[CH2:8](N(CC)CC)[CH3:9].[C:15]([OH:18])(=[O:17])[CH3:16].O1CC1C=C>COCCOCCOC>[C:15]([O:18][CH:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH:8]=[CH2:9])(=[O:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13586Vinyloxirane

Produkt 1

HCID 27350013,4-Diacetoxy-1-buteneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A 100-mL autoclave was charged with 45.25 g (0.44 mol) acetic anhydride, 1.62 g (0.016 mol) of triethylamine, 1.94 g (0.032 mol) acetic 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 2.25 hrs for analysis by GC. GC analysis of the crude mixture after 2.25 hrs revealed a 93% yield of 3,4-diacetoxy-1-butene with a 95% selectivity and 1.9% 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 0.029 min-1 (Table A). This example demonstrates the catalytic effect of a tertiary amine with two molar equivalents of acetic acid as a co-catalyst (Table B).

Aufarbeitung

  1. customThe autoclave was purged with helium twice
  2. customsequential samples were obtained every 15 min during the course of 2.25 hrs for analysis by GC

Quellen und Nachweise

ORD-Eintrag
ord-70dd7ad6f11f4b0da7d032c3ae8f2484
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623086

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