Acetic Acid → 1,6-Bis(cyclopentadienyl)hexane

HRID 1391075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391075
[Na].[CH:2]1[CH2:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Cl.C(O)(=O)C.C1(C)[C:20]([CH3:25])=[CH:21][CH:22]=[CH:23]C=1>C(O)(C)(C)C.CC1C2C(=CC=CC=2)NC(C)(C)C=1>[CH:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:20]2[CH:21]=[CH:22][CH:23]=[CH:25]2)[CH:2]=[CH:6][CH:5]=[CH:4]1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 7237O-XyleneHCID 7612CyclopentadieneHCID 165511,6-DichlorohexaneHCID 5360545Sodium

Produkt 1

HCID 858258481,6-Bis(cyclopentadienyl)hexaneAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6386tert-ButanolKatalysatorHCID 89812,2,4-Trimethyl-1,2-dihydroquinolineKatalysator

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A dispersion of 138 g of sodium in 800 g of xylene was mixed with 18 g of tertiary butanol and 436.2 g of monomeric cyclopentadiene were stirred in dropwise at 45° C. The mixture was heated for 2 hours at 45° C., then raised to the boil and 441.6 g of 1,6-dichlorohexane were dropped in. On completion of the dropwise addition 3.0 g of poly(2,2,4-trimethyl-1,2-dihydroquinoline) were added and the whole was heated for another 4 hours at the boil, then cooled, neutralized with a small quantity of glacial acetic acid, the precipitated sodium chloride was filtered off and thoroughly rinsed with xylene. After having distilled off the xylene under a vacuum of 15 mm Hg up to 130° C., there were obtained 552 g of the light-brown oligomeric 1,6-bis(cyclopentadienyl)hexane having a viscosity of 100,000 centipoises at 25° C. and a colour number (according to Gardner and Holdt) of 15. The molecular weight of the oligomer was 1125, corresponding to a polymerization degree of 5.

Aufarbeitung

  1. temperatureThe mixture was heated for 2 hours at 45° C.
  2. additionwere dropped in
  3. additionwere added
  4. temperaturethe whole was heated for another 4 hours at the boil
  5. temperaturecooled
  6. filtrationthe precipitated sodium chloride was filtered off
  7. washthoroughly rinsed with xylene
  8. distillationAfter having distilled off the xylene under a vacuum of 15 mm Hg up to 130° C.

Quellen und Nachweise

ORD-Eintrag
ord-5291acf0c48743cab234286de202b832
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04140843

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