Ammonia → Isophorone diamine

HRID 1492091Notes

Reaction equation

HRID 1492091 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.[O-2].[O-2].[Ti+4]>[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

6

Reactant 3

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

Product 1

HCID 17857Isophorone diamineYield 95.2%

Reagents, catalysts & solvents 2

HCID 162651Titanium oxide (Ti3O)CatalystHCID 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 63.5 g (100 ml) of titanium dioxide (anatase) in the form of 1.5 mm extrudates there were passed upwardly, per hour, 80.4 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 or 250 bar and a temperature of 120° C. Gas-chromatographic analysis of the hydrogenation product gave 95.2% of isophoronediamine in addition to 0.8% of 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane, corresponding to a diamine yield of 96.2% 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 80° C
  4. customthe effluent from the in-line imination reactor was passed upwardly through the hydrogenation reactor at a pressure or 250 bar
  5. customa temperature of 120° C

Sources & evidence

ORD record
ord-d59fbe808ffc4b4c9cc215a3c0385cfb
Source dataset
uspto-grants-1994_12
Patent number
US05371292

Reaction notes

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