Ammonia → 2,6-Dimethylcyclohexylamine

HRID 2412813Notes

Reaction equation

HRID 2412813 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1O.[O-2].[Pr+3].[O-2].[O-2].[Pr+3].[NH3:15].[H][H]>[Pd]>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[CH:3]1[NH2:15]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 113352,6-DimethylphenolHCID 165911Praseodymium oxideHCID 178418361HCID 178418361, compound

Product 1

HCID 1109322,6-DimethylcyclohexylamineYield 98.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
250 °C

Procedure

1,650 parts by weight of 2,6-dimethylphenol and 150 parts by weight of a pulverulent catalyst containing 10.0% by weight of palladium and 5.0% by weight of praseodymium oxide on aluminum oxide were introduced into a stirred autoclave having a capacity of 10,000 parts by volume. The autoclave was closed and 1,370 parts by weight of ammonia were forced in. The autoclave was then heated to 250° C. and hydrogen was introduced to bring the pressure to 300 bar. The autoclave was kept at the reaction temperature until constant pressure was achieved (about 10 hours). It was then allowed to cool and the mixture was filtered to give 1,691 parts by weight (98.5%) of 2,6-dimethylcyclohexylamine which, according to gas chromatography and NMR analysis, had the following isomer distribution:

Workup

  1. additionwere introduced into a stirred autoclave
  2. customThe autoclave was closed
  3. custom(about 10 hours)
  4. temperatureto cool
  5. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-4a3eb18361874f51a24296af0c29c4c7
Source dataset
uspto-grants-1985_01
Patent number
US04494983

Reaction notes

Loading…