1-Vinylimidazole
chemical compound
1-Vinylimidazole is a water-soluble basic monomer that forms quaternizable homopolymers by free-radical polymerization with a variety of vinyl and acrylic monomers. The products are functional copolymers, which are used as oil field chemicals and as cosmetic auxiliaries. 1-Vinylimidazole acts as a reactive diluent in UV lacquers, inks, and adhesives.
Preparation
The synthesis and properties of 1-vinylimidazole were described in a comprehensive article by Walter Reppe in 1957. Imidazole is first reacted with potassium hydroxide solution to form potassium imidazolate and the formed water is removed by distillation. Zinc oxide and potassium hydroxide are added to the basic catalyst potassium imidazolate and the free imidazole is ethinylated in 1,4-dioxane at 130 °C with ethine in an autoclave. The yield is 62%.
In a laboratory process, imidazole reacts in a two-phase system in the presence of a phase-transfer catalyst with 1,2-dichloroethane to give 1-(2-chloroethyl)imidazole and the latter is converted upon release of hydrogen chloride into 1-vinylimidazole in 92% yield.
Another lab scale procedure reports the vinylation of imidazole with bromoethene and kieselguhr-supported cesium fluoride in acetonitrile with a yield of 65%.
Properties
1-vinylimidazole is a colorless to brown, light-sensitive, hygroscopic and slightly alkaline reacting liquid with unpleasant, amine-like, fishy smell.
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