Polymerization reaction media can
have a profound effect on the
physical properties of the resultant polymer. This phenomenon is showcased
in a new experiment for the organic chemistry and polymer science
teaching laboratories wherein the radical copolymerization of biobased
β-myrcene and dibutyl itaconate is performed using a nonhazardous
aqueous emulsion solvent and compared to a bulk reaction. Both procedures
demonstrate multiple green chemistry principles and application to
sustainable polymer synthesis. The emulsion copolymerization produces
a tacky, elastomeric cross-linked material, capable of swelling to
many times its original volume in organic solvents, setting the stage
for the exploration of the relationship between solvent polarity and
swelling capacity. Conversely, the polymerization of β-myrcene
and dibutyl itaconate in the bulk yields a viscous non-cross-linked
polymer whose 1H NMR spectrum is suitable for student analysis
and estimation of polymer number-average molar mass (M
n), monomer conversion, and copolymer composition. This
inexpensive experiment models the use of renewable feedstocks, the
effect of reaction medium on polymer architecture, the unique properties
of cross-linked organogels, and the quantitative analysis of polymer
structure using 1H NMR spectroscopy.