Ammonia → 2,6-Dimethylaniline

HRID 223608Notes

Reaction equation

HRID 223608 reaction equation
[NH3:1].[H][H].[CH3:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH3:11])[CH:6]1[OH:12].[CH3:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH3:20])[C:15]1=[O:21]>[Pd].[Zn]>[CH3:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH3:11])[CH:6]1[OH:12].[CH3:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH3:20])[C:15]1=[O:21].[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[NH2:1]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 177802,6-DimethylcyclohexanoneHCID 214282,6-DimethylcyclohexanolHCID 178418361HCID 178418361, compound

Product 2

HCID 68962,6-DimethylanilineHCID 86738606HCID 86738606, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 23994ZincCatalyst

Procedure

1,000 parts by volume of catalyst are introduced into a fluidised bed reactor having a capacity of 1.2 liters, corresponding to 1,200 parts by volume. The catalyst consists of 0.5% by weight of palladium and 0.2% by weight of zinc on Al2O3 and has a particle size of 0.2 to 0.6 mm. The temperature in the reactor is set to 220° C. and, per hour, a correspondingly preheated mixture of 200,000 parts by volume of ammonia and 200,000 parts by volume of hydrogen is introduced. 50 parts of a mixture consisting of 80% by weight of 2,6-dimethylcyclohexanol and 20% by weight of 2,6-dimethylcyclohexanone is passed continuously, per hour, through the fluidised catalyst bed thus produced. The reaction product is isolated by cooling the exit gases, and is distilled. 100 parts of 2,6-dimethylcyclohexanol/2,6-dimethylcyclohexanone mixture employed give 92 parts of 2,6-dimethylaniline. Yield: 96.5%.

Workup

  1. addition1,000 parts by volume of catalyst are introduced into a fluidised bed reactor
  2. waitThe temperature in the reactor is set to 220° C. and, per hour
  3. additionis introduced
  4. waitis passed continuously, per hour, through the fluidised catalyst bed
  5. customthus produced
  6. customThe reaction product is isolated
  7. temperatureby cooling the exit gases
  8. distillationis distilled

Sources & evidence

ORD record
ord-782a3656fbcc4dd5991399f8e24c9d81
Source dataset
uspto-grants-1982_10
Patent number
US04355180

Reaction notes

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