Ammonia → Decahydroquinoline
Reaction equation
[C:1]([CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)#[N:2].[NH3:12].[H][H]>>[NH:2]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:1]1.[NH2:2][CH2:1][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[NH2:12]Participants
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 67.2 g (96 ml) of γ-aluminum oxide in the form of 1.5 mm extrudates, there were pumped upwardly, per hour, 22.6 g of 2-(2-cyanoethyl)-cyclohexanone (purity 96%, 0.144 mole) and 1,086 ml of liquid ammonia (652 g, 38.3 moles) at a pressure of 250 bar and a temperature of 70° C. Hydrogen was then added to the stream at a rate of 60 standard liters (2.7 moles) per hour, and the effluent from the in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure of 250 bar and a temperature of 120° C. Following separation and distillation of the product obtained after an on-stream period of 16.3 hours there were obtained, besides 43.5 g of decahydroquinoline, 291.7 g of 2-(3-aminopropyl)-cyclohexylamine. The yield of 2-(3-aminopropyl)-cyclohexylamine was 79.8% of theory.
Workup
- temperatureThrough a tubular reactor (diameter 16 mm, packing height 50 cm, oil-heated double jacket)
- waitwere pumped upwardly, per hour
- customa temperature of 70° C
- customthe effluent from the in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure of 250 bar
- customa temperature of 120° C
- customseparation and distillation of the product
- customobtained after an on-stream period of 16.3 hours there
Sources & evidence
- ORD record
- ord-da08f6233b2b4f74befd6df38bca77ff
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05239120
Reaction notes
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