Synthesis of Six-Membered Cyclic Carbonate Monomers by Disproportionation of 1,3-Bis(alkoxycarbonyloxy)propanes and Their Polymerization.

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  • ROKICKI Gabriel
    Warsaw University of Technology, Faculty of Chemistry, ul. Noakowskiego 3, 00 664 Warsaw, Poland
  • KOWALCZYK Tomasz
    Warsaw University of Technology, Faculty of Chemistry, ul. Noakowskiego 3, 00 664 Warsaw, Poland
  • GLINSKI Marek
    Warsaw University of Technology, Faculty of Chemistry, ul. Noakowskiego 3, 00 664 Warsaw, Poland

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Description

A new synthetic method of six-membered cyclic carbonates is presented. Different 1, 3-bis(alkoxycarbonyloxy)propanes obtained from 1, 3-diols and diethyl or dimethyl carbonate were subjected to disproportionation at 200-350°C in the presence of colloidal silica or Sn(II) stearate leading to 1, 3-dioxan-2-ones. The disproportionation was carried out in gaseous and liquid phases. The presented method was especially useful for preparation of six-membered mono- and biscyclic carbonates from polyfunctional alcohols such as trimethylolpropane, pentaerythritol and trimethylolpropane dimer. The structure of the polymers obtained from 5-methyl-1, 3-dioxan-2-one and 5-ethyl-5-methoxycarbonyloxymethyl-1, 3-dioxan-2-one in the presence of different catalysts were analyzed using MALDI-TOF mass spectrometry.

Journal

  • Polymer Journal

    Polymer Journal 32 (5), 381-390, 2000

    The Society of Polymer Science, Japan

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