Ammonia → 3-Butyl-3-ethylpiperidine

HRID 374366Notes

Reaction equation

HRID 374366 reaction equation
[CH:1]([C:5]([CH2:12][CH3:13])([CH2:8][CH2:9][C:10]#[N:11])[CH:6]=O)=[CH:2][CH2:3][CH3:4].N.O=[Si]=O.[H][H]>>[CH2:1]([C:5]1([CH2:12][CH3:13])[CH2:8][CH2:9][CH2:10][NH:11][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 222Ammonia2×HCID 24261SilicaHCID 713679144-Ethyl-4-formyloct-5-enenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 149931223-Butyl-3-ethylpiperidineYield 754.6%

Procedure

45.1 g per hour of 2-butenyl-2-ethyl-4-cyanobutanal (purity 64.0%, 28.9 g, 0.161 mol) and 950 ml (570 g, 33.5 mol) per hour of liquid ammonia were pumped at 250 bar and 50° C. through a tubular reactor (diameter 16 mm, fill level 50 cm, oil-heated twin jacket) upstream of the hydrogenation reactor and filled with 43.3 g (96 ml) of a Y-zeolite pelleted with Aerosil 200 (HY-zeolite: Aerosil 200=9:1, SiO2 :Al2O3 =6:1). The product stream was subsequently passed through the hydrogenation reactor from bottom to top at 250 bar and 120° C. while simultaneously passing 100 l(S.T.P.)/h (4.5 mol) of hydrogen through the reactor. The product stream was decompressed to atmospheric pressure and NH3 was removed by distillation. From the product from 23.9 hours, 205.7 g of 3-butyl-3-ethylpiperidine and 438.4 g of a mixture of 2-butyl- and 2-butenyl-2-ethylpentane-1,5-diamine (8:1), corresponding to a diamine yield of 61.9% of theory, were isolated by fractional distillation on a 30 cm packed column (3 mm glass rings).

Workup

  1. temperature(diameter 16 mm, fill level 50 cm, oil-heated twin jacket) upstream of the hydrogenation reactor
  2. customto top at 250 bar and 120° C.
  3. customwas removed by distillation

Sources & evidence

ORD record
ord-fd931ccfaf0748639b114f81f600d31f
Source dataset
uspto-grants-1992_11
Patent number
US05166443

Reaction notes

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