Aniline → Phenazine

HRID 2299584Notes

Reaction equation

HRID 2299584 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O>O>[CH:6]1[C:7]2[C:2](=[N:1][C:12]3[C:11]([N:8]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 7416Nitrobenzene

Product 1

HCID 4757Phenazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

86.24 gms of 25% aqueous TMA(OH) was added to 102.8 ml of deionized water. 107.8 gm of calcined and protonated ZSM-5 was added to form a slurry that was mixed vigorously at 40° C. for 3 hours and 15 minutes. The ion-exchanged material was filtered. The filtrate was kept aside for use in subsequent loadings. To make a 20% loading of TMA(OH) in the zeolite, 154.8 gms of 25% by weight of aqueous TMA(OH) was added to the cake. The resulting slurry was transferred to a rotary evaporator. The temperature of the heating medium was controlled at 40° C. and the rotary evaporator was equipped with a vacuum pump. The drying time was adjusted depending on the vacuum pressure at given temperature. It is preferred to run the drying temperature of not nore than 80° C. The most suitable temperature is 40° C. to reduce the level of TMA(OH) decomposition. For this example, the pressure was controlled at 13 mm Hg at 40° C. Drying was allowed to proceed for about an hour and 10 minutes. The resulting material produced a thick paste that was flowable. This material was transferred to a flat evaporating dish and allowed to further dry at about 35° C. for 15 hours in a vacuum desiccator. The dried solid was not hard and very easy to grind. The coupling reaction test, which consists of reacting aniline and nitrobenzene did not produce phenazine using the above prepared material.

Workup

  1. addition107.8 gm of calcined and protonated ZSM-5 was added
  2. customto form a slurry that
  3. additionwas mixed vigorously at 40° C. for 3 hours and 15 minutes
  4. filtrationThe ion-exchanged material was filtered
  5. additionwas added to the cake
  6. customThe resulting slurry was transferred to a rotary evaporator
  7. customwas controlled at 40° C.
  8. customthe rotary evaporator
  9. customwas equipped with a vacuum pump
  10. customnore than 80° C
  11. customis 40° C.
  12. customwas controlled at 13 mm Hg at 40° C
  13. customDrying
  14. customThe resulting material produced a thick paste that
  15. customto further dry at about 35° C. for 15 hours in a vacuum desiccator
  16. customvery easy to grind
  17. customThe coupling reaction test, which

Sources & evidence

ORD record
ord-23904ee6c6dd4cbbb7ab7a34db4870ca
Source dataset
uspto-grants-2002_12
Patent number
US06495723B1

Reaction notes

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