Ammonia → 2-Butyl-2-ethyl-1,5-pentanediamine

HRID 374367Notes

Reaction equation

HRID 374367 reaction equation
[CH2:1]([C:5]([CH2:12][CH3:13])([CH2:8][CH2:9][C:10]#[N:11])[CH:6]=O)[CH2:2][CH2:3][CH3:4].[NH3:14]>[H][H]>[CH2:1]([C:5]([CH2:12][CH3:13])([CH2:8][CH2:9][CH2:10][NH2:11])[CH2:6][NH2:14])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2205444-Ethyl-4-formyloctanenitrile

Product 1

HCID 49833442-Butyl-2-ethyl-1,5-pentanediamineYield 87.3%

Reagents, catalysts & solvents 1

HCID 178418361HCID 178418361, compoundSolvent

Procedure

80.0 g per hour of 2-butyl-2-ethyl-4-cyanobutanal (purity 99.3%, 0.44 mol) and 200 g (330 ml, 11.76 mol) per hour of liquid ammonia were pumped from bottom to top at 250 bar and 80° C. through a tubular reactor (diameter 16 mm, fill level 20 cm, oil-heated twin jacket) upstream of the hydrogenation reactor and filled with 25.4 g (40 ml) of TiO2 (anatase) in the form of 1.5 mm pellets. 100 l(S.T.P.)/h of hydrogen were then fed in, and the product stream from the upstream imination reactor was passed through the hydrogenation reactor from bottom to top at 250 bar and 110° C. The product stream was decompressed to atmospheric pressure and the ammonia was removed by distillation. According to gas-chromatographic analysis, the hydrogenation product stream contained 89.2% of 2-butyl-2-ethylpentane-1,5-diamine and 4.3% of 3-butyl-3-ethylpiperidine. The product from 80.5 hours was separated by fractional distillation on a 30 cm packed column (3 mm glass rings), giving 5738 g of 2-butyl-2-ethylpentane-1,5-diamine, corresponding to a yield of 87.3% of theory.

Workup

  1. customto top at 250 bar and 80° C. through a tubular reactor
  2. temperature(diameter 16 mm, fill level 20 cm, oil-heated twin jacket) upstream of the hydrogenation reactor
  3. customto top at 250 bar and 110° C
  4. customthe ammonia was removed by distillation
  5. customThe product from 80.5 hours was separated by fractional distillation on a 30 cm

Sources & evidence

ORD record
ord-e7a62284a6bf4958985f920f1eab21d3
Source dataset
uspto-grants-1992_11
Patent number
US05166443

Reaction notes

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