Azobisisobutyronitrile → HCID 131731368, compound

HRID 1019474Notes

Reaction equation

[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1([C:14]2[C:15]3([CH2:21][CH3:22])[CH2:20][CH:18]([CH:19]=2)[CH2:17][CH2:16]3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.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.[C:8]1([C:14]2[C:15]3([CH2:21][CH3:22])[CH2:20][CH:18]([CH:19]=2)[CH2:17][CH2:16]3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Maleic Anhydride (MA, 7.4 g, 75.0 mmol), Phenyl Ethyl Norbornene (PENB, 14.9 g, 75.0 mmol) and AIBN (1.2 g, 7.5 mmol) was dissolved in THF (32.1 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 17.5 hr, after which the solution was cooled to room temperature. The reaction mixture was diluted with 30 g of THF and added to hexane (1 L) to give a white powder that was filtered and dried in a vacuum oven at 80° C., for 16 hr. Approximately, 16.7 g (75%) of the MA/PENB polymer was isolated (GPC Mw=3,400 Mn=1,500).

Workup

additioncharged to an appropriately sized reaction vessel
customThe solution was sparged with nitrogen for 10 min
customto remove oxygen
temperatureafter which the solution was cooled to room temperature
additionThe reaction mixture was diluted with 30 g of THF
additionadded to hexane (1 L)
customto give a white powder that
filtrationwas filtered
customdried in a vacuum oven at 80° C., for 16 hr

Sources & evidence

ORD record: ord-7d910bea30ed47aaa3f79b2c6d925c26
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08715900B2

Reaction notes

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