Synthesis of a Novel Cyclic Compound from a Direct Reaction between Trioxane and Ethylene Oxide

The direct reaction of ethylene oxide with trioxane was thought impossible because of the weak basicity of trioxane. Thus, as the initiation mechanism of the copolymerization of trioxane and ethylene oxide, the formation mechanism of dioxolane from ethylene oxide and formaldehyde was proposed by several authors, and this mechanism was thought plausible for a long time. We found a new reaction, that is, the direct reaction of ethylene oxide with trioxane and isolated a novel cyclic formal. From this novel cyclic formal, 1, 3, 5-trioxepane was formed and then dioxolane was also generated. A new intermediate, or a novel cyclic compound, was separated using a micro-distillation apparatus. Its chemical structure was confirmed using 1H-NMR, 13C-NMR, Mass spectrum and elemental analysis. The new isolated intermediate or novel cyclic compound was 1, 3, 5, 7-tetraoxacyclononane, which identifies a new direct reaction between trioxane and ethylene oxide. This reaction identified the precise initiation mechanism of the copolymerization of trioxane and ethylene oxide.