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Issue 21, 2018
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Reaction pathways at the initial steps of trioxane polymerisation

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Abstract

Cleavage and (re)formation of oxymethylene moieties are essential steps during the build-up of polyoxymethylene (POM), a technically relevant high-performance polymer. To reveal how the catalyst accomplishes the cleavage of oxymethylene moieties, the kinetics of the ring-opening of trioxane was studied. Thereby insights into the initial phase of the growth of oxymethylene chains were obtained. The chain length of short oligomers was controlled with acetic anhydride as transfer agent. With a high ratio of acetic anhydride to trioxane, the first homologues of the series, trioxymethylene diacetate, dioxymethylene diacetate and monooxymethylene diacetate were obtained in excellent yield. The homologues show distinct features in the NMR and IR spectra that were related to their reactivity during chain propagation. Formation of intermediate hemi-acetal oxonium moieties is suggested to be a key step in the reaction pathway. Such molecular level insight may be a crucial factor for further tailoring production and properties of polyoxymethylene as well as introducing oligomeric oxymethylene diacetates to new application fields.

Graphical abstract: Reaction pathways at the initial steps of trioxane polymerisation

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Article information


Submitted
14 Aug 2018
Accepted
27 Sep 2018
First published
01 Oct 2018

Catal. Sci. Technol., 2018,8, 5594-5603
Article type
Paper

Reaction pathways at the initial steps of trioxane polymerisation

M. Hoffmann, C. Bizzarri, W. Leitner and T. E. Müller, Catal. Sci. Technol., 2018, 8, 5594
DOI: 10.1039/C8CY01691G

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