Ammonia → HCID 19005201, compound

HRID 2225964Notes

Reaction equation

HRID 2225964 reaction equation
[CH:1]([CH:4]([C:9](=O)[CH3:10])[CH2:5][CH2:6][C:7]#[N:8])([CH3:3])[CH3:2].[NH3:12]>[O-2].[O-2].[Ti+4].[H][H]>[CH:1]([CH:4]([CH:9]([NH2:12])[CH3:10])[CH2:5][CH2:6][CH2:7][NH2:8])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 2819694-acetyl-5-methylhexanenitrile

Product 1

HCID 19005201HCID 19005201, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 162651Titanium oxide (Ti3O)CatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

10 g of 4-isopropyl-5-oxohexanenitrile (purity 95.7%) and 115 g of liquid ammonia were pumped hourly from bottom to top at 250 bar and 80° C. through a tubular reactor (diameter 16 mm, fill level 50 cm, oil-heated twin jacket) arranged before the hydrogenation reactor and filled with 63.5 g (100 ml) of titanium dioxide (anatase) in the form of 1.5 mm pellets. 100 l (s.t.p.)/h of hydrogen were subsequently passed in, and the product discharged from the upstream imination reactor was passed through the hydrogenation reactor from bottom to top at 250 bar and 110° C. The mixture was decompressed at atmospheric pressure, the ammonia was removed by distillation, and the discharge from 72 hours was separated by fractional distillation on a 30 cm packed column (3-mm glass rings). 640 g of 4-isopropyl-1,5-hexanediamine were obtained as a colorless liquid (b.p. 80° C./1 mbar), corresponding to a yield of 90 %.

Workup

  1. customto top at 250 bar and 80° C. through a tubular reactor
  2. temperature(diameter 16 mm, fill level 50 cm, oil-heated twin jacket)
  3. customto top at 250 bar and 110° C
  4. customthe ammonia was removed by distillation
  5. customthe discharge from 72 hours was separated by fractional distillation on a 30 cm

Sources & evidence

ORD record
ord-21d4fd7d8f634e559d2c863776b7efb1
Source dataset
uspto-grants-1994_09
Patent number
US05344983

Reaction notes

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