Novel Ring-Expansion Reaction between Formaldehyde Cyclic Acetal and Ethylene Oxide
Naoaki YAMASAKI† and Junzo MASAMOTO*
Fukui University of Technology; 3-6-1 Gakuen, Fukui-shi 910-8505 Japan
† First Department of Additives Technology, Asahi Kasei Corporation; 6-2700, Asahi-machi, Nobeoka-shi 882-0847 Japan
We formerly found the novel ring-expansion reaction between 1,3,5-trioxane and ethylene oxide, and identified three novel compounds. Now, we found this type of reaction can be generalized to the ring-expansion reaction between formaldehyde cyclic acetal and ethylene oxide. We, first, confirmed this type of reaction between 1,3-dioxolane and ethylene oxide to form 1,3,6-trioxacyclooctane, 1,3,6,9-tetraoxacycloundecane and 1,3,6,9,12-pentaoxacyclotetradecane. When the initial ethylene oxide concentration is low, the formation of 1,3,6-trioxacyclooctane is predominant and selectivity for the formation of 1,3,6-trioxacyclooctane is nearly 99%. However, with the increase in initial ethylene oxide concentration, the formation of mixed reaction products of 1,3,6-trioxacyclooctane, 1,3,6,9-tetraoxacycloundecane and 1,3,6,9,12-pentaoxacyclotetradecane was observed. Further we confirmed the similar type of ring-expansion reaction between 1,3-dioxacycloheptane and ethylene oxide. From these observations, we concluded the general ring-expansion reaction between formaldehyde cyclic acetal and ethyelne oxide is valid.
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