Ammonia → 2-Methyl-2-propylpentane-1,5-diamine

HRID 374362Notes

Reaction equation

HRID 374362 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

5

Reactant 3

HCID 222Ammonia2×HCID 149931194-Formyl-4-methylheptanenitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 149931202-Methyl-2-propylpentane-1,5-diamineHCID 149931213-Methyl-3-propylpiperidine

Procedure

Example 2 was repeated, with 55.9 g of 2-methyl-2-propyl-4-cyanobutanal (purity 86.6%, 48.4 g, 0.316 mol) per hour and 1365 ml (819 g, 48.2 mol) per hour of liquid ammonia at 250 bar and 60° C. being pumped through the imination reactor. 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. The product from 16.8 hours was separated by fractional distillation on a 30 cm packed column (3 mm glass rings), giving 174.4 g of 3-methyl-3-propylpiperidine and 501.6 g of 2-methyl-2-propylpentane-1,5-diamine. The diamine yield was 59.6% of theory.

Workup

  1. customto top at 250 bar and 120° C.
  2. customwas removed by distillation
  3. customThe product from 16.8 hours was separated by fractional distillation on a 30 cm

Sources & evidence

ORD record
ord-4b99f27123164efab4e8e10886dedd4a
Source dataset
uspto-grants-1992_11
Patent number
US05166443

Reaction notes

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