Toluene → Phenyl isocyanate

HRID 1576127Notes

Reaction equation

HRID 1576127 reaction equation
[N:1]([C:3]1C=CC=CC=1)=O.[C]=[O:10].[C:11]1(C)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Rh](Cl)(Cl)Cl.[Co](I)I>[C:11]1([N:1]=[C:3]=[O:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 11473NitrosobenzeneHCID 178418416HCID 178418416, compound

Product 1

HCID 7672Phenyl isocyanateYield 29%

Reagents, catalysts & solvents 2

HCID 24872Rhodium chlorideCatalystHCID 41995115238-00-3Catalyst

Conditions

Temperature
200 °C

Procedure

The autoclave was charged with 10.0 grams of nitroso benzene, 63 grams (73 ml.) of toluene, 0.5 grams of rhodium trichloride, and 0.5 grams of anhydrous cobalt iodide. The autoclave was closed and then charged with sufficient carbon monoxide to increase the pressure to 1400 psig. The autoclave was heated to a temperature of 200°C. for 2 hours. After cooling the autoclave was vented, the contents filtered and the filtrate was analyzed by vapor phase chromotography. The product contained 3.2 grams of phenyl isocyanate, which corresponded to a corrected yield of 29 percent phenyl isocyanate.

Workup

  1. customThe autoclave was closed
  2. temperatureto increase the pressure to 1400 psig
  3. temperatureAfter cooling the autoclave
  4. filtrationthe contents filtered

Sources & evidence

ORD record
ord-be54a3922de94ded8a31102e0b55de56
Source dataset
uspto-grants-1976_09
Patent number
US03979427

Reaction notes

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