Methacrylic Acid → 2-Propenoic acid, 2-methyl-, 2-(2-propen-1-yloxy)ethyl ester

HRID 1247543

Reaktionsgleichung

Reaktionsgleichung von HRID 1247543
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([O:10][CH2:11][CH2:12]O)[CH:8]=[CH2:9].C([O-])(O)=O.[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[C:1]([O:6][CH2:12][CH2:11][O:10][CH2:7][CH:8]=[CH2:9])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Komponenten

6

Edukt 3

HCID 4093Methacrylic Acid2×HCID 8116Ethylene glycol monoallyl ether2×HCID 516892Sodium Bicarbonate

Produkt 1

HCID 856092-Propenoic acid, 2-methyl-, 2-(2-propen-1-yloxy)ethyl esterAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysator3×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A three-necked flask equipped with stirrer, thermometer, reflux condenser and Dean-Stark trap is charged with methacrylic acid (137.7 g, 1.6 mol), ethylene glycol monoallyl ether (80.7 g, 0.8 mol), p-toluenesulfonic acid (0.76 g, 4.0 mmol) and toluene (650 mL). After allowing the reaction to proceed at 120° C. for 5 hours, 0.12 g of p-toluenesulfonic acid is added, and the reaction is further allowed to proceed at the same temperature for 6 hours. Then, 0.1 g of p-toluenesulfonic acid is added, and the reaction is further allowed to proceed at the same temperature for 9 hours, whereupon the reaction is completed. During the whole reaction period, methacrylic acid and ethylene glycol monoallyl ether are monitored with liquid chromatography. The final conversion amounted to 98%. The reaction mixture is neutralized by adding an aqueous solution of NaHCO3 and allowed to separate into two layers. The aqueous layer is extracted once with toluene. The combined organic layer is dried over CaCl2 and the volatile matter is distilled off under reduced pressure. The crude product is distilled under reduced pressure (60° C., 2 mmHg) to give 98.7 g (73% yield) of 2-allyloxyethyl methacrylate shown below. H2C═C(CH3)CO2(CH2)2OCH2CH═CH2

Aufarbeitung

  1. customA three-necked flask equipped with stirrer
  2. temperaturethermometer, reflux condenser
  3. customthe reaction
  4. waitto proceed at the same temperature for 6 hours
  5. waitto proceed at the same temperature for 9 hours, whereupon the reaction
  6. customto separate into two layers
  7. extractionThe aqueous layer is extracted once with toluene
  8. dry with materialThe combined organic layer is dried over CaCl2
  9. distillationthe volatile matter is distilled off under reduced pressure
  10. distillationThe crude product is distilled under reduced pressure (60° C., 2 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-e71e9543e701480dbad539a47b10e2b4
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129294B2

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