Synthesis of novel formaldehyde acetals bearing long chain alkyl groups for use as chain transfer agent

We synthesized novel formaldehyde acetals bearing long chain alkyl groups, which could be potential chain transfer agent for the polymerization of tri oxane. We formerly reported the synthesis of a new poly(oxymethylene) with a long chain alkyl group using 1-octadecanol as a chain transfer agent. How ever, 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 gr oups is desired. For this purpose, we synthesized formaldehyde methyl octad ecyl acetal, formaldehyde bisoctadecyl acetal, starting from 1-octadecanol and formaldehyde dimethyl acetal as raw material using a cationic ion excha nge resin as catalyst by acetal exchange reaction. Synthesized materials ar e confirmed with H-1-NMR, mass spectra and elemental analysis. We also synt hesized formaldehyde acetal with a longer chain alkyl group starting from a n alcohol of carbon number of 38.