Benzene → Octylbenzene

Temperature

60 °C

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.

1. customThe less dense product phase was decanted from the ionic/catalyst phase
2. distillationpurified by Kugelrohr distillation
3. customThe ionic liquid and catalyst were prepared for reuse

ORD record

ord-003264d5ccdd440f95a8a86847058a0d

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06998497B2