Azobisisobutyronitrile → HCID 66688487, compound

HRID 2306841Notes

Reaction equation

HRID 2306841 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([O:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])(=[O:13])[C:10]([CH3:12])=[CH2:11].N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([O:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])(=[O:13])[C:10]([CH3:12])=[CH2:11]

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 7501StyreneHCID 17869(Dimethylamino)ethyl methacrylate

Product 1

HCID 66688487HCID 66688487, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 500 mL clear glass bottle was charged with 210 g toluene, 72.0 g styrene (product of Aldrich Chemical Company, Milwaukee, Wis), 28.0 g dimethylaminoethyl methacrylate (commercially obtained from Aldrich Chemical Company, Milwaukee, Wis.) and 1.35g of 2,2′-azobisisobutyronitrile (AIBN, commercially obtained from Aldrich Chemical Company, Milwaukee, Wis.). The resulting solution was purged with nitrogen for 10 minutes then placed in a tumbler with a heated water bath (Launder-o-meter, commercially obtained from Atlas Electric Products, Chicago Ill.) with the bath temperature set to 70° C. The mixture was allowed to react at 70° C. while tumbling for a period of 16 hours, then was removed and cooled to room temperature. An additional 72.0 g of styrene, 28.0 g of dimethylaminoethyl methacrylate and 1.35 g of AIBN were added to the bottle, which was again purged with nitrogen and tumbled at 70° C. for 20 hours. The resulting polymer solution in toluene was poured into heptane (approximately 3500 mL) to give a precipitate in the form of an opaque viscous liquid with a consistency like paste. The heptane was decanted from the precipitated polymer and the polymer was allowed to dry in a vented oven for 2 days. The dried, glassy polymer was dissolved in toluene and precipitated a second time, followed by decanting and drying to give a glassy solid product of poly(styrene-co-dimethylaminoethyl methacrylate) with calculated styrene/dimethylaminoethyl methacrylate mole ratio=8/2.

Workup

  1. customThe resulting solution was purged with nitrogen for 10 minutes
  2. customthen placed in a tumbler with a heated water bath
  3. customset to 70° C
  4. customto react at 70° C.
  5. customwas removed
  6. additionAn additional 72.0 g of styrene, 28.0 g of dimethylaminoethyl methacrylate and 1.35 g of AIBN were added to the bottle, which
  7. customwas again purged with nitrogen
  8. waittumbled at 70° C. for 20 hours
  9. additionThe resulting polymer solution in toluene was poured into heptane (approximately 3500 mL)
  10. customto give a precipitate in the form of an opaque viscous liquid with a consistency like paste
  11. customThe heptane was decanted from the precipitated polymer
  12. customto dry in a vented oven for 2 days
  13. dissolutionThe dried, glassy polymer was dissolved in toluene
  14. customprecipitated a second time
  15. customby decanting
  16. customdrying

Sources & evidence

ORD record
ord-179670612fe9400492c18b1099067ae4
Source dataset
uspto-grants-2004_12
Patent number
US06828358B2

Reaction notes

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