Water → alpha-Methylene-gamma-Valerolactone Acrylic Acid

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round bottom flask equipped with a magnetic stir bar was added 6.172 g (0.343 mol) water and 0.078 g (2.70×10−4 mol) sodium dodecyl sulfate (20% aqueous solution). The mixture was heated under flowing nitrogen to 73° C., at which point a monomer mixture consisting of 2.913 g (2.58×10−2 mol) α-methylene-γ-valerolactone that had been previously fractionally distilled and filtered over basic alumina and 0.154 g (2.56×10−3 mol) acrylic acid were added via syringe pump over 120 minutes. After 10 minutes of monomer mixture addition, an aqueous mixture consisting of 11.677 g (0.649 mol) water, 0.198 g (6.87×10−4 mol) sodium dodecyl sulfate (20% aqueous solution), 0.004 g (1.68×10−5 mol) sodium persulfate, and 0.029 g of a 20% aqueous sodium hydroxide solution was also added via syringe pump over 120 minutes. After both the monomer and aqueous mixtures were 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 under vacuum at 90° C. overnight. Size exclusion chromatography yielded a weight average molecular weight of 647 kDa and a polydispersity of 2.77, relative to polystyrene standards.

Provenance & Evidence