Acetic Acid → 3,4-Diacetoxy-1-butene

HRID 54721

반응식

HRID 54721 반응식
[O:1]1[CH2:5][CH:2]1[CH:3]=[CH2:4].[C:6]([O:9]C(=O)C)(=[O:8])[CH3:7].[C:13](O)(=[O:15])[CH3:14]>COCCOCCOC>[C:6]([O:9][CH:2]([CH2:5][O:1][C:13](=[O:15])[CH3:14])[CH:3]=[CH2:4])(=[O:8])[CH3:7]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 13586Vinyloxirane

생성물 1

HCID 27350013,4-Diacetoxy-1-butene수율 11%

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
125 °C

실험 절차

A 300-mL autoclave was charged with 40 mL (0.50 mol) of 3,4-epoxy-1-butene, 67.3 g (0.66 mol) acetic anhydride, 5.82 g (0.097 mol) of 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 2.5 hrs, samples were taken every 15 min for analysis by GC. GC analysis of the crude mixture after 2.5 hrs revealed 11% yield of 3,4-diacetoxy-1-butene with a 13% selectivity, 21% 3,4-epoxy-1-butene and numerous high boiling components. The reaction was observed to be first order in 3,4-epoxy-1-butene with a first order rate constant (Kfirst) of 0.0025 min-1 (Table A). This example illustrates low yield and selectivity in the absence of a tertiary amine and the inefficient catalysis of the reaction in the presence of the carboxylic acid alone.

후처리

  1. customThe autoclave was purged with nitrogen twice
  2. waitGC analysis of the crude mixture after 2.5 hrs revealed

출처 및 근거

ORD 기록
ord-7ecb83942ea440319dc3cf3eb9a62ee8
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623086

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