Ammonia → 3-Aminopentanenitrile

HRID 1009811

Reaction equation

HRID 1009811 reaction equation
[C:1](#[N:6])/[CH:2]=[CH:3]\[CH2:4][CH3:5].CC(=CC)C#[N:10].CC(C=C)C#N.[C:19](#[N:24])[CH2:20][CH2:21][CH2:22][CH3:23].N>C1C=CC=CC=1.C1CCCCC1>[NH2:10][CH:3]([CH2:4][CH3:5])[CH2:2][C:1]#[N:6].[C:19](#[N:24])/[CH:20]=[CH:21]\[CH2:22][CH3:23]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 8061ValeronitrileHCID 279092-Methyl-3-butenenitrileHCID 299352-Methyl-2-butenenitrileHCID 64339442-Pentenenitrile, (Z)-

Product 2

HCID 934513-AminopentanenitrileHCID 64339442-Pentenenitrile, (Z)-

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8078CyclohexaneSolvent

Procedure

A mixture of approximately 70 weight percent cis-2-pentenenitrile, 14 weight percent 2-methyl-2-butenenitrile, 4 weight percent 2-methyl-3-butenenitrile, with cyclohexane, benzene, and valeronitrile making up the balance, was reacted with 29 weight percent aqueous ammonia (at 15 percent molar excess relative to cis-2-pentenenitrile) in a stirred batch reactor at about 90° to 100° C., at an autogeneous pressure of about 60 to 118 psig, for approximately ten hours Vacuum distillation of the crude reaction mixture to remove low boiling impurities and water resulted in 91% selectivity to 3-aminopentanenitrile at 97% conversion of the starting cis-2-pentenenitrile

Workup

  1. distillationVacuum distillation of the crude
  2. customreaction mixture
  3. customto remove low boiling impurities and water

Sources & evidence

ORD record
ord-1cf7106d406649d68962d86d47430545
Source dataset
uspto-grants-2011_07
Patent number
US07973174B2

Linked notes

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