Aniline → Phenazine

HRID 2299582Notes

Reaction equation

HRID 2299582 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

116.0 gm of calcined and protonated ZSM-5 was added to a solution of 92.8 gms of 25% aqueous TMA(OH) and 116 ml of deionized water. The resulting slurry was ion exchanged for about 4 hours at 48° C. The slurry was filtered in a Buchner funnel. The filter cake was dried at 40° C. in a vacuum desiccator for fourteen hours and the filtrate set aside for use in subsequent loading. To the dried filter cake was added 122.7 gms of 25% aqueous TMA(OH). The resulting slurry was vigorously mixed at 40 ° C. for 30 minutes and dried in a vacuum desiccator for 72 hours with no inert gas purge. An additional 48 hours of drying at room temperature yielded a very hard solid material that was very difficult to grind. The ground solid consisted of what appeared to be two solid phases. A coupling reaction of aniline and nitrobenzene using the ground material from this preparation produced appreciable levels of phenazine.

Workup

  1. filtrationThe slurry was filtered in a Buchner funnel
  2. customThe filter cake was dried at 40° C. in a vacuum desiccator for fourteen hours
  3. filtrationTo the dried filter cake
  4. additionwas added 122.7 gms of 25% aqueous TMA(OH)
  5. additionThe resulting slurry was vigorously mixed at 40 ° C. for 30 minutes
  6. customdried in a vacuum desiccator for 72 hours with no inert gas
  7. custompurge
  8. customAn additional 48 hours of drying at room temperature
  9. customyielded a very hard solid material that
  10. customto grind

Sources & evidence

ORD record
ord-400673cca1af4fa483abb2ac2bf0a493
Source dataset
uspto-grants-2002_12
Patent number
US06495723B1

Reaction notes

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