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

HRID 374361Notes

Reaction equation

HRID 374361 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-methylheptanenitrile2×HCID 178418361HCID 178418361, compound

Product 2

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

Procedure

Example 1 was repeated using 2-methyl-2-propyl-4-cyanobutanal as the starting material. 33.5 g per hour of 2-methyl-2-propyl-4-cyanobutanal (purity 88.9%, 29.8 g, 0.195 mol) and 1400 ml (840 g, 49.4 mol) per hour of liquid ammonia were pumped at 250 bar and 60° C. 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 37.5 hours was separated 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 mmHg) and 842.1 g of 2-methyl-2-propylpentane-1,5-diamine (b.p.=78°- 81° C./2 mmHg). The diamine yield was 72.9% of theory.

Workup

  1. customwere pumped at 250 bar and 60° C. through the imination reactor
  2. customto top at 250 bar and 120° C.
  3. customwas removed by distillation
  4. customThe product from 37.5 hours was separated by fractional distillation on a 30 cm

Sources & evidence

ORD record
ord-0ee0872b2df7417bac59ccde2acdd8a6
Source dataset
uspto-grants-1992_11
Patent number
US05166443

Reaction notes

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