Synthesis of Novel Formaldehyde Acetals Bearing Long Chain Alkyl Groups for Use as Chain Transfer Agent

Abstract

We synthesized novel formaldehyde acetals bearing long chain alkyl groups, which could be potential chain transfer agent for the polymerization of trioxane. We formerly reported the synthesis of a new poly(oxymethylene) with a long chain alkyl group using 1-octadecanol as a chain transfer agent. However, using 1-octadecanol, one of the end-groups of the obtained polymer is a thermally stable octadecyloxy group, and the other is thermally unstable hydroxy group, respectively. The polymer with thermally stable both end groups is desired. For this purpose, we synthesized formaldehyde methyl octadecyl acetal, formaldehyde bisoctadecyl acetal, starting from 1-octadecanol and formaldehyde dimethyl acetal as raw material using a cationic ion exchange resin as catalyst by acetal exchange reaction. Synthesized materials are confirmed with ¹H-NMR, mass spectra and elemental analysis. We also synthesized formaldehyde acetal with a longer chain alkyl group starting from an alcohol of carbon number of 38.