Electron exchange polymers. XX. Preparation and polymerization of vinylbis(1‐ethoxyethyl)‐hydroquinone

The monomer vinylbis(1‐ethoxyethyl)hydroquinone, [vinylhydroquinonebis(ethyl acetal)], was prepared by reacting bromohydroquinone with vinyl ethyl ether, α‐chloroethyl ethyl ether being used as catalyst with great care to exclude moisture. The resulting bromohydroquinonebis(ethyl acetal) was subjected to lithium–bromine exchange followed by reaction with ethylene oxide. The resulting β‐hydroxyethylhydroquinone bis(ethyl acetal) was dehydrated to the desired monomer over potassium hydroxide at 235°. The overall yield from bromohydroquinone to purified monomer averaged 42%. The monomer polymerized under radical or anionic initiation. Polymer produced under radical initiation showed (in most instances) an intrinsic viscosity in benzene of the order of 0.32 at 29.7°C. The polymer is readily cleaved by dilute methanolic hydrochloric acid to give a polyvinylhydroquinone. A polyvinylhydroquinone prepared under anionic initiation showed an intrinsic viscosity of 0.34 in 90% methanol at 29.7°C. The polymer showed redox properties.