Synthesis, characterization and reactivity of a six-membered cyclic glycerol carbonate bearing a free hydroxyl group

Mariusz Tryznowski , Zuzanna Żołek-Tryznowska , Aleksandra Świderska , Paweł Parzuchowski

Abstract

Five- and six-membered cyclic carbonates have recently become popular as starting materials for the synthesis of polycarbonates via ring opening polymerization or synthesis of environmentally friendly non-isocyanate polyurethanes. In many cases a five-membered glycerol carbonate has been used in these applications. However, the simplest derivative of glycerol, a six-membered cyclic glycerol carbonate (5-hydroxy-1,3-dioxan-2-one), has not been reported so far. In this work, for the first time, we report a procedure for the synthesis of this monomer from glycerol. The product was characterized by 1H NMR, 13C NMR, and FTIR spectroscopy and X-ray diffraction measurements. Further, the synthesis of bis(2-oxo-1,3-dioxan-5-yl) sebacate, a biscyclic six-membered carbonate, was described. The reactivities of 5-hydroxy-1,3-dioxan-2-one and its biscyclic ester derivative were investigated. No ring opening polymerization of both the monomers was observed, instead an isomerization to appropriate five-membered cyclic carbonates occurred. Unfortunately, the protection of the hydroxyl group 2 with an ester type substituent does not protect it against isomerisation.
Author Mariusz Tryznowski KChTP
Mariusz Tryznowski,,
- Chair Of Polymer Chemistry And Technology
, Zuzanna Żołek-Tryznowska IMP
Zuzanna Żołek-Tryznowska,,
- The Institute of Mechanics and Printing
, Aleksandra Świderska KChTP
Aleksandra Świderska,,
- Chair Of Polymer Chemistry And Technology
, Paweł Parzuchowski KChTP
Paweł Parzuchowski,,
- Chair Of Polymer Chemistry And Technology
Journal seriesGreen Chemistry, ISSN 1463-9262
Issue year2016
Vol18
No3
Pages802-807
Publication size in sheets0.5
DOIDOI:10.1039/C5GC01688F
URL http://pubs.rsc.org/en/content/articlelanding/gc/2016/c5gc01688f#!divAbstract
Languageen angielski
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Score (nominal)45
ScoreMinisterial score = 45.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 45.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 9.125 (2) - 2016=8.815 (5)
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