Dihexylpropanedinitrile → 2,2-Dihexylpropane-1,3-diamine

HRID 1588186Notes

Reaction equation

HRID 1588186 reaction equation
[CH2:1]([C:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([C:10]#[N:11])[C:8]#[N:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(O)C.[Ni]>[CH2:12]([C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])([CH2:8][NH2:9])[CH2:10][NH2:11])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 1

HCID 19755212Dihexylpropanedinitrile

Product 1

HCID 197552132,2-Dihexylpropane-1,3-diamineYield 63.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

180.5 g (0.77 mol) of 2,2-dihexylpropanedinitrile was dissolved in 320 ml of ethanol. About 5 g of Raney nickel (dispersion in toluene) was added thereto, and the dinitrile was catalytically reduced at 100° C. under hydrogen pressure of 100 kg/m2 in an autoclave for 6 hours. The catalyst was removed, and ethanol was distilled off to obtain an oily material. The oily material was distilled under reduced pressure to obtain 119 g of the desired product as a colorless oil (boiling point: 153° to 160° C./4 mmHg).

Workup

  1. customwas catalytically reduced at 100° C. under hydrogen
  2. customfor 6 hours
  3. customThe catalyst was removed
  4. distillationethanol was distilled off
  5. customto obtain an oily material
  6. distillationThe oily material was distilled under reduced pressure

Sources & evidence

ORD record
ord-8bb001f28fc943928c0d70f355ef675b
Source dataset
uspto-grants-1993_06
Patent number
US05221603

Reaction notes

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