Abstract
The thermal elimination of NaCl from sodium chloroacetate, a polymerization reaction that takes place between 150 and 200‡C in the solid state, leads quantitatively to the simplest polyester, polyglycolide. Byin situ IR-spectroscopy, we have shown that the reaction proceeds smoothly and directly without intermediates or by-products. The endgroups of the polymeric product — ionised carboxylate groups (-COONa) and hydrogen-bonded alcohol groups (−COH) — are clearly detectable. It is therefore concluded that the polymer forms extended chains, not rings, during the course of this solid-state reaction. That corresponds well with the idea of a polymerization reaction in the solid state. However, this experiment does not exclude the formation of polyglycolide rings as further product because they do not contain any terminating groups.
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M. E. and H. K. thank Prof. A. Reller, Hamburg, for generous support. Dr. G. Sankar, London, is acknowledged for experimental assistance. This work was supported by the Deutsche Forschungsgemeinschaft (Bonn, Germany), the Fonds der Chemischen Industrie (Frankfurt/Main, Germany) and the Engineering and Physical Sciences Research Council (UK).
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Epple, M., Kirschnick, H. & Thomas, J.M. An in situ IR-spectroscopic study of the solid-state formation reaction of polyglycolide. Journal of Thermal Analysis 47, 331–337 (1996). https://doi.org/10.1007/BF01983973
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DOI: https://doi.org/10.1007/BF01983973