Isoprene → 4-Cyclohexene-1,2-dicarboxylic acid, 4-methyl-, dimethyl ester

HRID 61342

Reaktionsgleichung

Reaktionsgleichung von HRID 61342
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[C:6]([O:14][CH3:15])(=[O:13])/[CH:7]=[CH:8]\[C:9]([O:11][CH3:12])=[O:10]>>[CH3:12][O:11][C:9]([CH:8]1[CH2:1][CH:2]=[C:3]([CH3:5])[CH2:4][CH:7]1[C:6]([O:14][CH3:15])=[O:13])=[O:10]

Komponenten

3

Edukt 2

HCID 6557IsopreneHCID 5271565Dimethyl maleate

Produkt 1

HCID 2743794-Cyclohexene-1,2-dicarboxylic acid, 4-methyl-, dimethyl esterAusbeute 66,7 %

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Isoprene (350 g, 5.1 mol) and dimethyl maleate (741 g, 5.1 mol) were loaded into a stainless steel autoclave. The autoclave was sealed and heated to 150° C. The temperature of the autoclave increased to 195° C. due to the heat of the reaction. The temperature was held at 160° C. for 1 hour. Gas chromatography (GC) analysis indicated the completion of the reaction. The autoclave was then cooled to room temperature. Simple distillation of the resulting mixture provided 4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester (725 g, 3.4 mol, 66% yield) as a light yellow liquid.

Aufarbeitung

  1. customThe autoclave was sealed
  2. temperatureThe temperature of the autoclave increased to 195° C. due to the
  3. temperatureheat of the reaction
  4. customthe completion of the reaction
  5. temperatureThe autoclave was then cooled to room temperature
  6. distillationSimple distillation of the resulting mixture

Quellen und Nachweise

ORD-Eintrag
ord-eba05cae420d4eb5ae930194eb321a31
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441185B2

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