Azobisisobutyronitrile → Phosphine, octyl-

HRID 261012Notes

Reaction equation

HRID 261012 reaction equation
N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:13]=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[PH3:21]>C1C=CC=CC=1>[CH2:13]([PH2:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 81251-Octene2×HCID 24404Phosphine

Product 1

HCID 446269Phosphine, octyl-Yield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

A 1-liter autoclave was charged with 5 g of azobisisobutyronitrile, 50 g of benzene and 112 g (1 mol) of 1-octene, and 136 g (4 mols) of hydrogen phosphide was condensed thereinto. The whole was heated to 90° C. The pressure initially rose to 70 bars, then dropped gradually to 55 bars, and remained constant after 5 hours. The reaction mixture was analyzed by NMR-spectroscopy. The octene conversion rate was 85%. Primary octylphosphine was obtained in a yield of 70%, secondary octylphosphine was obtained in a yield of 20%, and tertiary octylphosphine was obtained in a yield at 10%, based on the quantity of 1-octene which underwent conversion.

Workup

  1. customcondensed
  2. additiondropped gradually to 55 bars

Sources & evidence

ORD record
ord-d4864d5bbe6f48d9941e79dc4c7f0d38
Source dataset
uspto-grants-1979_08
Patent number
US04163760

Reaction notes

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