Azobisisobutyronitrile → zinc methacrylate N,N'-ethylenebisacrylamide

HRID 1167035

Reaction equation

HRID 1167035 reaction equation
[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[Zn+2:7].[C:8]([O-:13])(=[O:12])[C:9]([CH3:11])=[CH2:10].[CH2:14]([NH:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH2:15][NH:16][C:17](=[O:20])[CH:18]=[CH2:19].CC(N=NC(C#N)(C)C)(C#N)C>CO>[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[Zn+2:7].[C:8]([O-:13])(=[O:12])[C:9]([CH3:11])=[CH2:10].[CH2:15]([NH:16][C:17](=[O:20])[CH:18]=[CH2:19])[CH2:14][NH:21][C:22](=[O:25])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 1689642-Propenamide, N,N'-1,2-ethanediylbis-HCID 101308962-Propenoic acid, 2-methyl-, zinc salt (2:1)

Product 1

HCID 86759156zinc methacrylate N,N'-ethylenebisacrylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Zinc methacrylate (848 mg, 3.6 mmol), N,N′-ethylenebisacrylamide (50 mg, 0.30 mmol) and VAZO® (20 mg, 0.08 mmol) were dissolved in methanol (3 ml) in a borosilicate test tube. The solution was sonicated for 1 min and sparged with nitrogen. The test tube was covered with parafilm and placed in an ice bath. The reaction mixture was allowed to go to room temperature while being irradiated at 365 nm for 24 hrs. The resulting opaque polymer was scraped out of the test tube and ground in a Retsch RM100 Mortar Grinder for 1 min. The polymer powder was suspended in methanol (25 ml), filtered through a fluted paper filter and washed with methanol (100 ml). The polymer was then stirred up in acetone (50 ml) and allowed to settle for 0.5 hr. The finest particles remained suspended in the supernatant, which was discarded. The polymer was subsequently air-dried at approximately 50° C. for 48 hrs.

Workup

  1. customThe solution was sonicated for 1 min
  2. customsparged with nitrogen
  3. customplaced in an ice bath
  4. customto go to room temperature
  5. customwhile being irradiated at 365 nm for 24 hrs
  6. filtrationfiltered through a fluted paper
  7. filtrationfilter
  8. washwashed with methanol (100 ml)
  9. waitto settle for 0.5 hr
  10. customThe polymer was subsequently air-dried at approximately 50° C. for 48 hrs

Sources & evidence

ORD record
ord-758ded2bcb244c69bf8cfa8848914b09
Source dataset
uspto-grants-2003_09
Patent number
US06616846B2

Linked notes

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