Acrylonitrile → Propanenitrile, 3,3′-(1,4-cyclohexanediyldiimino)bis-

HRID 1795478Notes

Reaction equation

HRID 1795478 reaction equation
[CH:1]1([NH2:8])[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.[C:9](#[N:12])[CH:10]=[CH2:11]>C(O)C>[C:9]([CH2:10][CH2:11][NH:7][CH:4]1[CH2:5][CH2:6][CH:1]([NH:8][CH2:2][CH2:3][C:4]#[N:7])[CH2:2][CH2:3]1)#[N:12]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 183741,4-Diaminocyclohexane

Product 1

HCID 11009504Propanenitrile, 3,3′-(1,4-cyclohexanediyldiimino)bis-Yield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

In a 5-liter reactor, 531.5 g of 1,4-cyclohexanediamine were placed and warmed at 80° C. until total fusion of the product. Then 675 mL of acrylonitrile were added and the mixture was warmed at 80° C. for 1 h, and at 100° C. for 2 h. Then 960 mL of ethanol were added and it was cooled down to room temperature, occurring the precipitation of a solid. After filtering, washing with ethanol and drying, 952.2 g (92.8%) of the title compound were obtained as a brown solid. Elemental analysis (%): theory, C 65.49, H 9.09, N 25.45; found, C 65.80, H 9.20, N 26.16.

Workup

  1. temperaturethe mixture was warmed at 80° C. for 1 h
  2. temperatureit was cooled down to room temperature
  3. customthe precipitation of a solid
  4. filtrationAfter filtering
  5. washwashing with ethanol
  6. customdrying

Sources & evidence

ORD record
ord-daec34c5e5904158bbafaf0a3c277479
Source dataset
uspto-grants-2006_04
Patent number
US07026514B2

Reaction notes

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