Ammonia → 3,3-Dimethylpiperidine

HRID 374360Notes

Reaction equation

HRID 374360 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:5][CH2:6][C:7]#[N:8])[CH:3]=O.[NH3:10].[H][H]>>[CH3:1][C:2]1([CH3:9])[CH2:5][CH2:6][CH2:7][NH:8][CH2:3]1.[CH3:1][C:2]([CH3:9])([CH2:5][CH2:6][CH2:7][NH2:8])[CH2:3][NH2:10]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 802314-Formyl-4-methylvaleronitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 709423,3-DimethylpiperidineHCID 110407352,2-Dimethylpentane-1,5-diamine

Procedure

34.0 g per hour of 2,2-dimethyl-4-cyanobutanal (purity 93.4%, 31.8 g, 0.254 mol) and 1450 ml (870 g, 51.1 mol) per hour of liquid ammonia were pumped at 250 bar and 60° C. through a tubular reactor (diameter 16 mm, fill level 50 cm, oil-heated twin jacket) upstream of the hydrogenation reactor and filled with 63.5 g (100 ml) of TiO2 (anatase) in the form of 1.5 mm pellets. The discharge from the reactor 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. The product from 32.4 hours was separated by fractional distillation on a 30 cm packed column (3 mm glass rings), giving 344.8 g of 3,3-dimethylpiperidine (b.p. 50°-52° C./210 mmHg) and 753.6 g of 2,2-dimethylpentane-1,5-diamine (b.p.=72° C./8 mmHg). The diamine yield was 70.5% of theory.

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
  4. customThe product from 32.4 hours was separated by fractional distillation on a 30 cm

Sources & evidence

ORD record
ord-5b53f5c3534b4e5e9d0ff2f92a8ce4db
Source dataset
uspto-grants-1992_11
Patent number
US05166443

Reaction notes

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