Ammonia → 2-Methyl-2-propylpentane-1,5-diamine
Reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH3:11])([CH2:5][CH2:6][C:7]#[N:8])[CH:3]=O.[NH3:12].[H][H]>>[CH3:1][C:2]1([CH2:9][CH2:10][CH3:11])[CH2:5][CH2:6][CH2:7][NH:8][CH2:3]1.[CH3:1][C:2]([CH2:9][CH2:10][CH3:11])([CH2:5][CH2:6][CH2:7][NH2:8])[CH2:3][NH2:12]Participants
Procedure
33.5 g of 2-methyl-2-propyl-4-cyanobutanal (purity: 88.9%, 29.8 g, 0.195 mol) and 1,400 ml (840 g, 49.4 mol) of liquid ammonia were pumped per hour at 250 bar and 60° C. through a tubular reactor (diameter: 16 mm, filling level: 50 cm, oil-heated twin jacket) which was arranged upstream of the hydrogenation reactor and was filled with 63.5 g (100 ml) of TiO2 (anatase) in the form of 1.5 mm pellets. The product was then passed through the hydrogenation reactor from bottom to top at 250 bar and 120° C. while simultaneously passing through 100 l (s.t.p.)/h (4.5 mol) of hydrogen. After decompression to atmospheric pressure, NH3 was removed by distillation. The product from 37.5 hours was separated into its components by fractional distillation on a 30 cm packed column (3 mm glass rings), giving 277.0 g of 3-methyl-3-propylpiperidine (b.p.=46° C./2 mm Hg) and 842.1 g of 2-methyl-2-propylpentane-1,5-diamine (b.p.=78°-81° C./2 mm Hg). The yield of diamine was 72.9% of theory.
Workup
- temperature(diameter: 16 mm, filling level: 50 cm, oil-heated twin jacket) which
- customto top at 250 bar and 120° C.
- customAfter decompression to atmospheric pressure, NH3 was removed by distillation
- customThe product from 37.5 hours was separated into its components by fractional distillation on a 30 cm
Sources & evidence
- ORD record
- ord-fc5be8901c7e4a2fa7788e84a3a1cfab
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05554787
Reaction notes
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