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

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 2with an ester type substituent does not protect it against isomerisation

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

M. Tryznowski,*^a   Z. Żołek-Tryznowska,^b   A. Świderska^a and  P. G. Parzuchowski^a  

*Corresponding authors

^aFaculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
E-mail: tryznowski@ch.pw.edu.pl

^bFaculty of Production Engineering, Warsaw University of Technology, Narbutta 85, 02-524 Warsaw, Poland

Green Chem., 2015, Advance Article

DOI: 10.1039/C5GC01688F.......http://pubs.rsc.org/en/Content/ArticleLanding/2015/GC/C5GC01688F?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Paweł Parzuchowski

Warsaw University of Technology Faculty of Chemistry ul. Noakowskiego 3, 00-664 Warszawa, Poland Phone: +48 22 234 7317. E-mail: pparzuch@ch.pw.edu.pl

faculty of Chemistry, Warsaw University of Technology, Noakowskiego

//////faculty of Chemistry, Warsaw University of Technology, Noakowskiego







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