1-Octene → Octane

HRID 567658Notes

Reaction equation

HRID 567658 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C1CCCCC1.CCCCCCC.[CH-]1[C-]=[C-][C-]=[C-]1.[CH-]1[C-]=[C-][C-]=[C-]1.Cl[Ti]Cl>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:1][CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 1

HCID 81251-Octene

Product 2

HCID 356OctaneHCID 8126Oct-2-ene

Reagents, catalysts & solvents 3

HCID 416358Bis(cyclopentadienyl)titanium(IV) chlorideCatalystHCID 8078CyclohexaneSolvent2×HCID 8900HeptaneSolvent

Procedure

0.12 mmoles of bis-(η5-cyclopentadienyl)titanium dichloride (Cp2TiCl2; Aldrich commercial product), 20 ml of anhydrous cyclohexane, 0.03 ml of a solution of n-dibutylglima 0.45 M in anhydrous cyclohexane and 0.54 ml of 1 molar Mg(butyl)2 in n-heptane (atomic ratio Mg/Ti=4.5), are charged into a tailed test-tube equipped with a magnetic stirrer, in an atmosphere of argon. The mixture is left under stirring for 20 hours at room temperature. 18.8 ml of 1-octene (distilled and maintained on molecular sieves) are added. At this point the solution is siphoned in an autoclave previously maintained under argon and the same procedure is carried out as described in example 1 above. At the end it is cooled to room temperature. About 14 ml of octane and 4 ml of 2-octene are obtained by distillation (GC, mass GC and NMR analyses). The results and process conditions are summarized in table 1 below.

Workup

  1. customequipped with a magnetic stirrer, in an atmosphere of argon
  2. waitThe mixture is left
  3. temperaturepreviously maintained under argon
  4. temperatureAt the end it is cooled to room temperature

Sources & evidence

ORD record
ord-eeb13e21c0b84dd1bbb2834d05d724ac
Source dataset
uspto-grants-2001_01
Patent number
US06180553B2

Reaction notes

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