Ammonia → 2-Butyl-2-ethyl-1,5-pentanediamine
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
20.0 g per hour of 2-butyl-2-ethyl-4-cyanobutanal (purity 99.3%, 0.11 mol) and 140 g (230 ml, 8.23 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 50 cm, oil-heated twin jacket) upstream of the hydrogenation reactor and filled with 70.0 g (100 ml) of γ -Al2O3 in the form of 1.5 mm pellets. 60 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 95.4% of 2-butyl-2-ethylpentane-1,5-diamine and 2.3% of 3-butyl-3-ethylpiperidine. The product from 48.0 hours was separated by fractional distillation on a 30 cm packed column (3 mm glass rings), giving 920 g of 2-butyl-2-ethylpentane-1,5-diamine, corresponding to a yield of 93.9% of theory.
Workup
- customto top at 250 bar and 80° C. through a tubular reactor
- temperature(diameter 16 mm, fill level 50 cm, oil-heated twin jacket) upstream of the hydrogenation reactor
- customto top at 250 bar and 110° C
- customthe ammonia was removed by distillation
- customThe product from 48.0 hours was separated by fractional distillation on a 30 cm
Sources & evidence
- ORD record
- ord-3a377842fa4a4d19b54e947dccd459a1
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166443
Reaction notes
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