Nitrobenzene → Azobenzene

HRID 2285450Notes

Reaction equation

HRID 2285450 reaction equation
ClCl.[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-])=O.[C]=O.[C:14]1([N:20]=C=O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Pd].C12C=C3N=C(C=C3)C=C3NC(C=C3)=CC3=NC(C=C3)=CC(N1)=CC=2.[Pd].ClC1C=CC=CC=1Cl>[N:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:3][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 7416Nitrobenzene2×HCID 7672Phenyl isocyanateHCID 24526ChlorineHCID 178418416HCID 178418416, compound

Product 1

HCID 2272Azobenzene

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178419802HCID 178419802, compoundCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
230 °C

Procedure

The chemical analysis indicates a content of 14.8% of palladium and a content of chlorine less than 0.5%. 2.0 grams of palladium porphyrin and 30 grams of nitrobenzene are charged into the autoclave previously described and the total volume is completed to 100 ml with orthodichlorobenzene. A stream of nitrogen is passed in at atmospheric pressure, then it is compressed with carbon monoxide until the pressure reaches 200 bars at 20° C. The autoclave is isolated and heated to 230° C., which brings the pressure of 340 bars. The mixture is allowed to react for 7 hours while maintaining it under agitation, then allowed to cool and analyzed. The O.C.R. of the nitrobenzene is 25.4% and the selectivity to phenylisocyanate is 94.8%. No azobenzene is formed.

Workup

  1. customat 20° C
  2. customThe autoclave is isolated
  3. customto react for 7 hours
  4. temperaturewhile maintaining it under agitation
  5. temperatureto cool

Sources & evidence

ORD record
ord-867572eccfc4452e82f01b4ecc5558e8
Source dataset
uspto-grants-1982_04
Patent number
US04323515

Reaction notes

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