Aniline → Phenazine

HRID 2299586Notes

Reaction equation

HRID 2299586 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

Conditions

Temperature
35 °C

Procedure

This example is similar to TMA(OH) loading Example No. 7 except that the slurry contained 262.4 gms of calcined and protonated ZSM-5, 211.4 gms. Of 25% aqueous TMA(OH) and 262 ml of deionized water. The ion exchange was conducted at 40° C. for three hours. The filter cake after ion exchange was dried using a vacuum desiccator without a nitrogen purge overnight at room temperature. The drier cake was further dried in a vacuum desiccator at 35° C. for 2.5 hours using a nitrogen purge. For a 20% target loading of TMA(OH) onto the ZSM-5, 413.8 gms of 25% aqueous TMA(OH) was added into a vessel that was connected to an assembly that was similar to a rotary evaporator. The hot water bath was maintained at about 35° C. and the drying/evaporating process was conducted for about 2.5 hours at vacuum pressures between 8 and 38 mm Hg. The dried material was removed from the vessel and transferred to a flat dish for further drying in a vacuum desiccator. The drying in the vacuum desiccator was kept at 40° C. for about 3 hours. The resulting dried material was not hard, and easy to grind and consisted of what appears to be one phase when ground. A coupling reaction test based on reacting aniline and nitrobenzene failed to produce phenazine.

Workup

  1. customThe filter cake after ion exchange was dried
  2. custompurge overnight at room temperature
  3. customThe drier cake was further dried in a vacuum desiccator at 35° C. for 2.5 hours
  4. custompurge
  5. additionFor a 20% target loading of TMA(OH) onto the ZSM-5, 413.8 gms of 25% aqueous TMA(OH) was added into a vessel that
  6. customwas similar to a rotary evaporator
  7. waitthe drying/evaporating process was conducted for about 2.5 hours at vacuum pressures between 8 and 38 mm Hg
  8. customThe dried material was removed from the vessel
  9. customfor further drying in a vacuum desiccator
  10. waitThe drying in the vacuum desiccator was kept at 40° C. for about 3 hours
  11. customeasy to grind
  12. customA coupling reaction test

Sources & evidence

ORD record
ord-972a3bcf6bdc420b9814aa037dd49974
Source dataset
uspto-grants-2002_12
Patent number
US06495723B1

Reaction notes

Loading…