The activated double bond in this five-membered oxygen-containing heterocycle makes the molecule a reactive monomer for homopolymerization and copolymerization and a dienophile in Diels-Alder reactions.
The separation of the by-products from the final product by distillation by thin-film evaporator,[4] fractional recrystallization[8] or zone melting[9] is very expensive.
[4] Highly pure vinylene carbonate can be obtained in yields of more than 70% by optimizing the chlorination conditions to suppress the formation of by-products[6] and a combination of several gentle purification processes.
By suitable process control and purification steps, a solid product with a melting point of 20-22 °C and a chlorine content below 10ppm can be obtained.
Liquid vinylene carbonate turns rapidly yellow even in the absence of light and must be stabilized by the addition of radical scavengers.
[17] This polymer film allows ionic conduction, but prevents the reduction of the electrolyte at the negative (graphite) electrode and contributes significantly to the long-term stability of lithium-ion batteries.
[21][22] The preparation of higher molecular weight polymers with useful properties depends critically on the purity of the vinylene carbonate monomer.
[23] Vinylene carbonate can be homopolymerized in bulk, in solution, in suspension and in dispersion using radical initiators such as azobis(isobutyronitrile) (AIBN) or benzoyl peroxide.
[10] Analogous to cellulose, polyhydroxymethylene can be dissolved in hot sodium hydroxide solution and converted by crosslinking into a highly swellable polymer which can take up to 10,000 times its weight in water.