Azobisisobutyronitrile → MA BuNB

HRID 1019472

Reaction equation

HRID 1019472 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([CH:12]1[CH2:17][CH:16]2[CH2:18][CH:13]1[CH:14]=[CH:15]2)[CH2:9][CH2:10][CH3:11].CC(N=NC(C#N)(C)C)(C#N)C>C1COCC1>[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1.[CH2:8]([CH:12]1[CH2:17][CH:16]2[CH2:18][CH:13]1[CH:14]=[CH:15]2)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 168020Bicyclo[2.2.1]hept-2-ene, 5-butyl-

Product 1

HCID 131731366MA BuNBYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Maleic Anhydride (MA, 9.8 g, 100 mmol), 5-Butyl-2-norbornene (BuNB, 15.0 g, 100 mmol) and AIBN (1.64 g, 10.0 mmol) was dissolved in THF (37.2 g) and charged to an appropriately sized reaction vessel. The solution was sparged with nitrogen for 10 min to remove oxygen and then heated to 70 ° C. The mixture was allowed to stir at 70° C. for 16 hr, after which the solution was cooled to room temperature. The reaction mixture was added to hexane (2 L) to give a white powder that was filtered and dried in a vacuum oven at 80° C. for 1 hr. Approximately, 19.3 g (78%) of the MA/BuNB polymer was isolated (GPC Mw=3,200 Mn=1,900).

Workup

  1. additioncharged to an appropriately sized reaction vessel
  2. customThe solution was sparged with nitrogen for 10 min
  3. customto remove oxygen
  4. temperatureafter which the solution was cooled to room temperature
  5. additionThe reaction mixture was added to hexane (2 L)
  6. customto give a white powder that
  7. filtrationwas filtered
  8. customdried in a vacuum oven at 80° C. for 1 hr

Sources & evidence

ORD record
ord-f4eea584a1434912b619602a0c84645e
Source dataset
uspto-grants-2014_05
Patent number
US08715900B2

Linked notes

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