Nitrobenzene → Azobenzene

HRID 2285451Notes

Reaction equation

HRID 2285451 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-])=O.[C]=O.[C:12]1([N:18]=C=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C2C3NC(=CC=3)C(C3C=CC=CC=3)=C3N=C(C=C3)C(C3C=CC=CC=3)=C3NC(C=C3)=C(C3C=CC=CC=3)C3=NC=2C=C3)C=CC=CC=1.[Pd].ClC1C=CC=CC=1Cl>[N:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[N:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

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

Product 1

HCID 2272Azobenzene

Reagents, catalysts & solvents 2

HCID 136447763Palladium tetraphenylporphyrinCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
235 °C

Procedure

Into the autoclave previously described, 2 grams of palladium tetraphenylporphyrin and 30 grams of nitrobenzene are introduced and the total volume adjusted to 100 ml by means of orthodichlorobenzene. The reactor is closed and after scavenging with nitrogen, carbon monoxide is introduced until the pressure reaches 200 bars at 20° C. The autoclave is isolated and while maintaining an agitation is heated at 235° C. for 3 hours, then at 240° C. for 4 hours, 30 minutes. After cooling, the mixture is analyzed. The O.C.R. of the nitrobenzene is 94.7% and the selectivity for phenylisocyanate is 60.2%. No azobenzene is formed.

Workup

  1. customThe reactor is closed
  2. additionis introduced until the pressure
  3. customat 20° C
  4. customThe autoclave is isolated
  5. temperaturewhile maintaining an agitation
  6. custom30 minutes
  7. temperatureAfter cooling

Sources & evidence

ORD record
ord-46b97913c3d4456eab80beb86f6f89d4
Source dataset
uspto-grants-1982_04
Patent number
US04323515

Reaction notes

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