Azobisisobutyronitrile → HCID 86755013, compound

HRID 848947Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[C:10]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])[C:11]([CH3:13])=[CH2:12].N(C(C)(C)C#N)=NC(C)(C)C#N.O1CCOCC1>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[C:10]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])[C:11]([CH3:13])=[CH2:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A 500-ml flask was charged with 72.1 g (0.60 mol) of 4-hydroxystyrene, 17.0 g (0.12 mol) of n-butyl methacrylate, 1.5 g (0.009 mol) of azobisisobutyronitrile and 150 ml of dioxane, and the mixture was stirred for 20 hours at 80° C. in a nitrogen gas stream. The resultant reaction mixture was poured into 5 liters of xylene, and precipitate formed was collected by filtration. The resultant solids were dissolved in 200 ml of diethyl ether, and the solution was poured into 3 liters of n-hexane to collect precipitate formed by filtration (reprecipitation process). This reprecipitation process was repeated 3 times, and the resultant precipitate was then dried to obtain 23.6 g of a 4-hydroxystyrene/n-butyl methacrylate copolymer. The GPC analysis of the polymer thus obtained revealed that its Mw was 5,600. Besides, the 1H-NMR spectrum analysis of the polymer revealed that the copolymerization ratio of 4-hydroxystyrene to n-butyl methacrylate was 68/32.

Workup

customThe resultant reaction mixture
customformed
filtrationwas collected by filtration
dissolutionThe resultant solids were dissolved in 200 ml of diethyl ether
additionthe solution was poured into 3 liters of n-hexane
customto collect precipitate
customformed by filtration (reprecipitation process)
dry with materialthe resultant precipitate was then dried

Sources & evidence

ORD record: ord-57d36bb1310d4243a7e98e4b93e95fa7
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06010826

Reaction notes

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