Acrylamide → HCID 86738175, compound

HRID 1660298Notes

Reaction equation

HRID 1660298 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[CH2:6]([N:9]([CH2:18][CH:19]=[CH2:20])[CH:10]=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15])[CH:7]=[CH2:8]>C(O)C>[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[CH2:6]([N:9]([CH:10]=[CH:11][CH:12]=[C:13]([C:14]#[N:15])[C:16]#[N:17])[CH2:18][CH:19]=[CH2:20])[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 6579AcrylamideHCID 53724731{3-[Di(prop-2-en-1-yl)amino]prop-2-en-1-ylidene}propanedinitrile

Product 1

HCID 86738175HCID 86738175, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

In a 10 liters flask, supplied with stirrer, reflux and internal thermometer, 230 g. of acrylamide and 120 g. of 3-diallylaminoallylidenemalononitrile (A) were dissolved in 4 liters of ethanol at 96%. The mixture temperature was increased to 78° C. under agitation. 8 g. of 2,2'-azobisisobutyrronitrile (AZBN) were introducted at this point. After 10 minutes, a yellowish product began separating. The reaction was continued under those conditions for 14 hours. The mixture was then cooled at room temperature; the separated product was filtered, washed with diethyl ether and vacuum dried at 50° C. The yield of the solid yellowish product was 320 g., with 8% aminoallylidenemalononitrile units in weight. The IR, spectrophotometric analysis and the TLC confirmed for the polymer a structure with allylidenemalononitrile groups. The solution at 6% in 70/30 water/ethanol diluted 1:2000 in water showed an optical density of 0.7 at 382 nm.

Workup

  1. customIn a 10 liters flask, supplied with stirrer
  2. temperaturereflux
  3. customa yellowish product began separating
  4. waitThe reaction was continued under those conditions for 14 hours
  5. temperatureThe mixture was then cooled at room temperature
  6. filtrationthe separated product was filtered
  7. washwashed with diethyl ether and vacuum
  8. customdried at 50° C
  9. additionThe solution at 6% in 70/30 water/ethanol diluted 1:2000 in water

Sources & evidence

ORD record
ord-9047c868830240c1aa6f84b0a0cf26cb
Source dataset
uspto-grants-1981_12
Patent number
US04307184

Reaction notes

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