Ammonia → Isophorone diamine

HRID 1492092Notes

Reaction equation

HRID 1492092 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:8][C:7]([C:10]#[N:11])([CH3:9])[CH2:6][C:4](=O)[CH2:3]1.[NH3:13].[H][H]>O1CCCC1>[CH3:1][C:2]1([CH3:12])[CH2:8][C:7]([CH2:10][NH2:11])([CH3:9])[CH2:6][CH:4]([NH2:13])[CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 990683-Cyano-3,5,5-trimethylcyclohexanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 17857Isophorone diamineYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 70.0 g (100 ml) of γ-aluminum oxide in the form of 1.5 mm extrudates there were passed upwardly, per hour, 40.4 g of a 50% solution of isophoronenitrile (purity 99.0%) in tetrahydrofuran and 303.0 g of liquid ammonia at a pressure of 250 bar and a temperature of 80° 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 130° C. The effluent was depressurized to standard pressure, and the ammonia was distilled off. The hydrogenation product contained, apart from tetrahydrofuran, 96.4% of isophoronediamine and 0.6% of 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane, as determined by gas-chromatographic analysis. The product obtained over an on-stream period of 121 hours was collected and separated by fractional distillation. There were obtained 2,371 g of isophoronediamine, corresponding to a yield of 95.1%.

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 80° C
  4. customthe effluent from the in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure of 250 bar
  5. customa temperature of 130° C
  6. distillationthe ammonia was distilled off
  7. customThe product obtained over an on-stream period of 121 hours
  8. customwas collected
  9. customseparated by fractional distillation

Sources & evidence

ORD record
ord-11c044daf8924a0ebab2de035526d111
Source dataset
uspto-grants-1994_12
Patent number
US05371292

Reaction notes

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