Azobisisobutyronitrile → HCID 86587525, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 ml, round bottom flask equipped with a reflux condenser and a gas inlet was combined maleic anhydride (8.76 g, 0.089 mol) and tetrahydrofuran (30 ml). The mixture was stirred under a N2 atmosphere until all the maleic anhydride was dissolved. To this solution was added allyltrimethylsilane (10.23 g, 0.089 mol), t-butyl acrylate (8.82 g, 0.069 mol), methyl acrylate (1.20 g, 0.014 mol), acrylic acid (1.0 g, 0.014 mol) and 2,2'-azobisisobutyronitrile (0.146 g, 0.9 mmol). The mixture was heated to 64° C., and the mixture was stirred at this temperature for 18 h. The reaction mixture was cooled to room temperature and added dropwise to hexanes (500 ml). The precipitate was filtered, and the solid was dried in vacuo (12 mm Hg) at room temperature for 1 h. The solid was dissolved in tetrahydrofuran (50 ml), and the solution was added dropwise to hexanes (500 ml). The precipitate was filtered, and the solid was dried in vacuo (0.2 mm Hg) 50° C. for 16 h giving poly(maleic anhydride-allyltrimethylsilane-t-butyl acrylate-methyl acrylate-acrylic acid) (23.9 g, 79.7%) as a white powder. 1H NMR (d6-acetone, 250 MHz): 30.0 mole % maleic anhydride, 30.0 mole % allyltrimethylsilane, 25.4 mole % t-butyl acrylate, 14.8 mol % methyl acrylate. GPC V software, Phenogel-10, 7.8×250 mm column: 10-4A, 500A & 50A, THF eluent]): Mw =14, 921; Polydispersity=2.51; Rmin =2.5 Å/sec.

Provenance & Evidence