Affiliation:
1. The George and Josephine Butler Laboratory for Polymer Research, Department of Chemistry
Abstract
The origins and recent applications of acetal metathesis are discussed in the context of synthesizing polyacetals via acetal metathesis polymerization (AMP). A kinetic study of the acid-catalyzed acetal metathesis reaction suggests the rate = k[H+][acetal]2, with MeOCH2OMe and EtOCH2OEt interchanging to yield MeOCH2OEt, achieving the statistical 1:2:1 equilibrium distribution in 4 hours at 80 °C and in 1 hour at 90 °C. Upon heating 1,10-decanediol and diethoxymethane, polydecylene acetal is formed with sequential distillation of ethanol, followed by diethoxymethane. A full mechanism for this polymerization is proposed, which begins with a transacetalization sequence to convert the diol into a bisacetal, followed by acetal metathesis to yield a high-molecular-weight polymer.
Funder
National Science Foundation
Cited by
4 articles.
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