Benzene → 1-Octene

HRID 890854

Reaktionsgleichung

Reaktionsgleichung von HRID 890854
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.C([N+]1C=CN(C)C=1)CCC.C([N+]1C=CN(C)C=1)CCC.N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Ni+2]>[CH2:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:7]=[CH:8][CH2:1][CH2:6][CH2:5][CH2:4][CH2:3][CH3:2]

Komponenten

6

Edukt 2

HCID 241BenzeneHCID 81251-Octene2×

Produkt 2

HCID 81251-OcteneHCID 16607Octylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131725278Nickel(II) bis-triflimideKatalysatorHCID 178448536HCID 178448536, VerbindungLösungsmittel

Versuchsvorschrift

Nickel(II) bis-triflimide (0.06 g, 0.1 mmol) was dissolved in [bmim][NTf2] (1.0 g) in a round-bottomed flask equipped with a magnetic stirrer and reflux condenser. Benzene (3.90 g, 50 mmol) and oct-1-ene (1.12 g, 10 mmol) were added. The mixture was heated under reflux for 18 hours and was analysed by gas chromatographic analysis as in previous examples. The oct-1-ene peak disappeared and three isomers of octylbenzene were formed (70%, 20:26:54 2- to 3- to 4-isomer ratio) as well as octene dimer (30%). The less dense product phase was decanted from the ionic/catalyst phase and purified by Kugelrohr distillation. The ionic liquid and catalyst were prepared for reuse by heating at 60° C. under vacuum for 1 hour. The ionic liquid and catalyst were used for further reactions of benzene with oct-1-ene without loss of activity. This is an alkylation of benzene with an alkene using a metal bis-triflimide catalyst. Benzene and oct-1-ene react in the presence of 1% nickel(II) bis-triflimide in [bmim][NTf2] to form three isomers of octyl benzene and a small amount of hexadecene (unknown isomeric distribution). This is shown below: The Alkylation of Benzene with oct-1-ene.

Aufarbeitung

  1. customequipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-5ef476920480468e880aab830198be04
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06998497B2

Verknüpfte Notizen

Wird geladen…