Water → alpha-Methylene-gamma-Butyrolactone Acrylic Acid

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottom flask equipped with a magnetic stir bar was added 44.045 g (2.44 mol) water and 0.512 g (1.78×10−3 mol) sodium dodecyl sulfate (20% aqueous solution). The mixture was heated under flowing nitrogen to 74° C., at which time a monomer mixture consisting of 20.805 g (2.13×10−1 mol) α-methylene-γ-butyrolactone that had been previously filtered over basic alumina and 1.100 g (1.83×10−3 mol) acrylic acid was added dropwise over 110 minutes. After 10 minutes of monomer mixture addition, an aqueous mixture consisting of 83.37 g (4.63 mol) water, 1.32 g (4.58×10−3 mol) sodium dodecyl sulfate (20% aqueous solution), 0.047 g (1.97×10−4 mol) sodium persulfate, and 0.175 g of a 20% aqueous sodium hydroxide solution was also added via syringe pump over 110 minutes. After both the monomer and aqueous mixtures had added completely, the emulsion was allowed to stir for an additional 60 minutes, after which the reaction was cooled to room temperature and dried under vacuum at 90° C. overnight. Size exclusion chromatography yielded a weight average molecular weight of 507 kDa and a polydispersity of 1.75, relative to polystyrene standards.

Provenance & Evidence