Ammonia → 4,4-Dimethyl-1,5-hexanediamine

HRID 2225962Notes

Reaction equation

HRID 2225962 reaction equation
[CH3:1][C:2]([CH3:10])([C:7](=O)[CH3:8])[CH2:3][CH2:4][C:5]#[N:6].[NH3:11]>[O-2].[O-2].[Ti+4].[H][H]>[CH3:1][C:2]([CH3:10])([CH:7]([NH2:11])[CH3:8])[CH2:3][CH2:4][CH2:5][NH2:6]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 131577824,4-Dimethyl-5-oxohexanenitrile

Product 1

HCID 183143544,4-Dimethyl-1,5-hexanediamineYield 88%

Reagents, catalysts & solvents 2

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

Procedure

21 g of 4,4-dimethyl-5-oxohexanenitrile (purity 97.2%) and 180 g of liquid ammonia were pumped hourly from bottom to top at 250 bar and 80° C. through a tubular reactor (diameter 0.16 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, and the ammonia was removed by distillation. The discharge from 24 hours was separated by fractional distillation on a 30 cm packed column (3-mm glass rings). 445 g of 4,4-dimethyl-1,5-hexanediamine were obtained as a colorless liquid (b.p. 90° C./3 mbar), corresponding to a yield of 88%.

Workup

  1. customto top at 250 bar and 80° C. through a tubular reactor
  2. temperature(diameter 0.16 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 24 hours was separated by fractional distillation on a 30 cm

Sources & evidence

ORD record
ord-e2846d64d85a419b92710959e049a5dc
Source dataset
uspto-grants-1994_09
Patent number
US05344983

Reaction notes

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