Ammonia → Decahydroquinoline

HRID 2255286Notes

Reaction equation

HRID 2255286 reaction equation
O=[Si]=O.[C:4]([CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)#[N:5].[NH3:15].[H][H]>>[NH:5]1[CH:13]2[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6][CH2:4]1.[NH2:5][CH2:4][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[NH2:15]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 24261SilicaHCID 962232-OxocyclohexanepropiononitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 92911DecahydroquinolineHCID 108881552-(3-Aminopropyl)-cyclohexylamine

Procedure

Through a tubular reactor (diameter 16 mm, packing height 50 cm, oil-heated double jacket), installed up-stream of the hydrogenation reactor and packed with 41.6 g (92 ml) of a zeolite type Y which had been extruded with Aerosil 200 (ratio Y-type zeolite to Aerosil 200 9:1, ratio SiO2 to Al2O3 6:1), there were passed upwardly, per hour, 36.7 g of 2-(2-cyanoethyl)-cyclohexanone (purity 96%, 0.233 mole) and 1.475 ml of liquid ammonia (885 g, 52.1 moles) at a pressure of 250 bar and a temperature of 70° C. Hydrogen was then added to the stream at a rate of 150 standard liters (6.7 moles) per hour, and the effluent from this in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure of 250 bar and a temperature of 120° C. The product mixture was depressurized to standard pressure and fed to the top of a column (length 46 cm, diameter 3 cm) held at 40° C. and packed with 5 mm wire mesh rings in which the ammonia was removed. After an on-stream time of 19.9 hours distillation of the product had yielded, besides 189.7 g of decahydroquinoline, 431.2 g of 2-(3-aminopropyl)-cyclohexylamine, this corresponding to a yield of 2-(3-aminopropyl)-cyclohexylamine of 59.6% of theory.

Workup

  1. temperatureThrough a tubular reactor (diameter 16 mm, packing height 50 cm, oil-heated double jacket)
  2. waitwere passed upwardly, per hour
  3. customa temperature of 70° C
  4. customthe effluent from this in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure of 250 bar
  5. customa temperature of 120° C
  6. customheld at 40° C.
  7. customwas removed
  8. distillationAfter an on-stream time of 19.9 hours distillation of the product

Sources & evidence

ORD record
ord-e1e63441bd0a49618705fe643ce06e48
Source dataset
uspto-grants-1993_08
Patent number
US05239120

Reaction notes

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