Benzene → 1-Octene

HRID 505983

反応式

HRID 505983 の反応式
CCCCN1C=[N+](C)C=C1.[CH:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>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]>[CH2:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[CH2:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

6

実験手順

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 reaction shown below:

後処理

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

出典と根拠

ORDレコード
ord-61e6783ed67542258175cc7aaa5a200d
出典データセット
uspto-grants-2010_08
特許番号
US07781625B2

関連ノート

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