A process for the manufacture of bis-methylene spiro-orthocarbonate (BMSOC)
wherein methyallyl chloride is subjected to the action of chlorine gas to
form a mixture of 1,1-dichloromethyl ethylene and other chlorinated
hydrocarbons which need not be and are not separated. The mixture is
merely treated wich an alkali metal acetate such as sodium acetate to
yield an easily separable second mixture by fractional distillation. The
desired 1,1-diacetoxymethyl ethylene is thus recovered in high yield. It
is then converted by transesterification in over 90% yield to the
bismethylene spiroorthocarbonate (BMSOC). BMSOC is useful as a component
for coatings composites, adhesive formulations and the like, which have
the unique ability to (a) cure by free radical initiation and (b) expand
during cure. BMSOC may be used as a component for dental composites, i.e.
filling materials, because it reduces the possibility of leakage at the
margin, i.e. at the composite-enamel interface and as a component in bone
cements. It is also useful for the reduction of voids in electrical
insulating coatings because it reduces the likelihood of corona and/or
dielectric breakdown.