Aniline → Phenazine

HRID 2299585Notes

Reaction equation

HRID 2299585 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
40 °C

Procedure

195.4 gms of calcined and protonated ZSM-5 was added to a mixture of 156.3 gms of 25% aqueous TMA(OH) and 195 ml of deionized water. The solution was ion exchanged for three hours at 40° C. using a hot water bath. The slurry was filtered and the filtrate was set aside for future loadings and ion exchange. The filter cake was subjected to further drying in a vacuum desiccator that was equipped with a nitrogen purge. The drying in the vacuum desiccator was at 35° C. and maintained at that temperature for several hours (48 hours or less) for complete removal of the moisture. The dried material was treated with 216.3 gms of 25% aqueous TMA(OH) for a 20% target loading of TMA(OH). The resulting slurry was dried in a rotary evaporator set-up for several hours until it was moist dry. The rotary evaporator was run at 35° C. and 4 to 35 mm Hg. The dried material was transferred to a flat dish and placed in a vacuum desiccator with an inert gas purge. The vacuum desiccator is maintained at 40° C. and drying was allowed for several hours (48 hours or less). 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. filtrationThe slurry was filtered
  2. customto further drying in a vacuum desiccator that
  3. customwas equipped with a nitrogen
  4. custompurge
  5. customwas at 35° C.
  6. temperaturemaintained at that temperature for several hours (48 hours or less)
  7. customfor complete removal of the moisture
  8. additionThe dried material was treated with 216.3 gms of 25% aqueous TMA(OH) for a 20% target loading of TMA(OH)
  9. customThe resulting slurry was dried in a rotary evaporator set-up for several hours until it
  10. customThe rotary evaporator
  11. customwas run at 35° C.
  12. custompurge
  13. customdrying
  14. waitwas allowed for several hours
  15. custom(48 hours or less)
  16. customeasy to grind
  17. customA coupling reaction test

Sources & evidence

ORD record
ord-a067c6a652dd4cd69756a1d83771b9c4
Source dataset
uspto-grants-2002_12
Patent number
US06495723B1

Reaction notes

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