Triphenyl phosphite → Formyloctadecanonitrile

HRID 223689Notes

Reaction equation

HRID 223689 reaction equation
[C:1](#[N:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]1([O:26]P(OC2C=CC=CC=2)OC2C=CC=CC=2)C=CC=CC=1>[Rh]>[CH:20]([CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:1]#[N:19])=[O:26]

Participants

4

Reactant 2

HCID 7540Triphenyl phosphiteHCID 6420241(Z)-9-Octadecenenitrile

Product 1

HCID 20520510Formyloctadecanonitrile

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Conditions

Temperature
130 °C

Procedure

Into a 1 liter, 316 SS autoclave equipped with stirrer and heat exchange coil is placed 617 grams of olenitrile, 3.0 grams of 5 percent rhodium on aluminum (Englehardt Industries) and 3.2 grams of triphenylphosphite. The autoclave is flushed with nitrogen then pressurized with carbon monoxidehydrogen (1:1) to 1080 psig. The temperature is increased to 127-133 degrees C. and maintained from 3.3 hours with a CO--H2 pressure of 970-1080 psig. At this point a GC analysis indicated complete reaction of oleonitrile with the formation of FON. The reaction was cooled, the pressure vented and the product filtered. The yield of FON is 681. Rhodium is removed from the product by vacuum distillation.

Workup

  1. customInto a 1 liter, 316 SS autoclave equipped with stirrer
  2. temperatureheat exchange coil
  3. customThe autoclave is flushed with nitrogen
  4. temperatureand maintained from 3.3 hours with a CO--H2 pressure of 970-1080 psig
  5. customreaction of oleonitrile with the formation of FON
  6. temperatureThe reaction was cooled
  7. filtrationthe product filtered
  8. customRhodium is removed from the product by vacuum distillation

Sources & evidence

ORD record
ord-a883ec260746439c875a3b6074e90ea7
Source dataset
uspto-grants-1982_10
Patent number
US04356128

Reaction notes

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