Ammonia → Decahydroquinoline

Participants

Reaction Steps

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.

Provenance & Evidence