Ammonia → Ammonia

HRID 6276

Reaction equation

HRID 6276 reaction equation
[NH3:1].[C:2](#[N:5])[CH:3]=[CH2:4]>O>[NH3:5].[C:2](#[N:5])[CH:3]=[CH2:4].[NH2:5][CH2:2][CH2:3][C:4]#[N:1].[C:2]([CH2:3][CH2:4][NH:1][CH2:4][CH2:3][C:2]#[N:5])#[N:5]

Participants

7

Reactant 2

HCID 222Ammonia3×HCID 7855Acrylonitrile2×

Product 4

HCID 222AmmoniaHCID 16473-AminopropionitrileHCID 7855AcrylonitrileHCID 81493,3'-Iminodipropionitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

It is also known that the addition of protic solvents has an advantageous effect on the addition reaction of NH3 with acrylonitrile. The addition of steam to the mixture of acrylonitrile and ammonia is disclosed in, for example, Chem. Abstr. Vol. 83, 26879. Usually, however, aqueous ammonia is used in the temperature range from 80° to 130° C. With a ratio of ammonia to acrylonitrile to water of 5-15:1:5-20, 3-aminopropionitrile is obtained, in addition to bis(2-cyanoethyl)amine, in yields of from 57 to 80% (eg. U.S. Pat. No. 3,935,256--62%, DE-A-24 36 651--70%, U.S. Pat. No. 2,448,013--78%, U.S. Pat. No. 2,819,903--59%, Org. Syn. (1947), 27, 3 to 5 - 57%). The disadvantages of these processes using aqueous ammonia arise in the working up or further processing of the product mixture:

Workup

  1. additionIt is also known that the addition of protic solvents
  2. additionThe addition of steam
  3. customis used in the temperature range from 80° to 130° C

Sources & evidence

ORD record
ord-994fe399445642c1ae38540975c70fa4
Source dataset
uspto-grants-1993_09
Patent number
US05247120

Linked notes

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