Acrylonitrile → 3,3'-[(3-Aminopropyl)azanediyl]di(propane-1,2-diol)

HRID 426906

Reaction equation

HRID 426906 reaction equation
[OH:1][CH:2]([CH2:10][OH:11])[CH2:3][NH:4][CH2:5][CH:6]([OH:9])[CH2:7][OH:8].[C:12](#[N:15])[CH:13]=[CH2:14]>>[OH:9][CH:6]([CH2:7][OH:8])[CH2:5][N:4]([CH2:3][CH:2]([OH:1])[CH2:10][OH:11])[CH2:14][CH2:13][CH2:12][NH2:15]

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 184035543,3'-Iminobispropane-1,2-diol

Product 1

HCID 234677983,3'-[(3-Aminopropyl)azanediyl]di(propane-1,2-diol)

Procedure

Bis-(2,3-dihydroxypropyl)amine (16.5 g., 0.1 mole) and acrylonitrile (6.4 g., 0.12 mole) is mixed in an ice bath and then warmed to room temperature. After standing for 2 hours, the mixture was then heated at 45° C.-55° C. for 3 hours. The excess acrylonitrile is removed by gentle warming under reduced pressure. The residue was taken up in ethyl alcohol, mixed with sponge nickel catalyst and hydrogenated under 200 psi hydrogen using good agaitation. After filtration of catalyst the solvent and excess acrylonitrile is removed by stripping under reduced pressure to leave the product.

Workup

  1. temperaturethe mixture was then heated at 45° C.-55° C. for 3 hours
  2. customThe excess acrylonitrile is removed
  3. temperatureby gentle warming under reduced pressure
  4. additionmixed with sponge nickel catalyst and hydrogenated under 200 psi hydrogen using good agaitation
  5. filtrationAfter filtration of catalyst the solvent and excess acrylonitrile
  6. customis removed
  7. customto leave the product

Sources & evidence

ORD record
ord-d01e11f3b3e44b03a5e3e5b7cacf5cd6
Source dataset
uspto-grants-1979_10
Patent number
US04172094

Linked notes

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