N-methyl-2-pyrrolidone → [4-(Ethenyloxy)phenyl](phenyl)methanone

HRID 9701

Reaktionsgleichung

Reaktionsgleichung von HRID 9701
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.CN1CC[CH2:19][C:18]1=O>C1C=C2C(C=C(C([O-])=O)C=C2)=CC=1.C1C=C2C(C=C(C([O-])=O)C=C2)=CC=1.[Zn+2]>[CH:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1)=[CH2:19]

Komponenten

4

Edukt 2

HCID 13387N-methyl-2-pyrrolidoneHCID 143474-Hydroxybenzophenone

Produkt 1

HCID 21987723[4-(Ethenyloxy)phenyl](phenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13879901Zinc naphthenateKatalysator

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

A mixture of 650 g of 4-hydroxybenzophenone (98% by weight, Avocado, Research Chemicals Ltd.), 750 ml of N-methylpyrrolidone (>99% by weight, BASF AG) and 60 g of zinc naphthenate (Nusa; zinc salts of naphthenic acids, zinc content 12% by weight) was charged with stirring to a 2.5 l autoclave and flushed with nitrogen. After it had been heated to 190° C., injection was carried out first with nitrogen to 2 bar and then with acetylene to 20 bar. During the reaction, further acetylene was supplied to replace that consumed by reaction, so as to maintain a constant pressure of 20 bar. After a reaction time of 12 hours the batch was cooled to 20–25° C. (room temperature) and let down to atmospheric pressure. The solvent was distilled off under reduced pressure at a bridge temperature of from 70 to 80° C. with a pressure of 1 mbar (absolute). 310 g of Pluriol® E 600 (polyethylene glycol, trademark of BASF AG) were then added and the product was purified by a Sambay distillation at 1.2 mbar (absolute) and a bridge temperature of 163° C. This gave a total of 522 g of 4-vinyloxybenzophenone having a purity of from 96 to 99% by weight and a melting point of 58° C.

Aufarbeitung

  1. additionwas charged
  2. customflushed with nitrogen
  3. customDuring the reaction, further acetylene
  4. customthat consumed by reaction
  5. temperatureso as to maintain a constant pressure of 20 bar
  6. temperatureAfter a reaction time of 12 hours the batch was cooled to 20–25° C. (room temperature)
  7. distillationThe solvent was distilled off under reduced pressure at a bridge temperature of from 70 to 80° C. with a pressure of 1 mbar (absolute)
  8. addition310 g of Pluriol® E 600 (polyethylene glycol, trademark of BASF AG) were then added
  9. distillationthe product was purified by a Sambay distillation at 1.2 mbar (absolute)
  10. customa bridge temperature of 163° C

Quellen und Nachweise

ORD-Eintrag
ord-63c05866145e472c88a3d838aafd9c42
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091296B2

Verknüpfte Notizen

Wird geladen…