Trimethylene carbonate

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Trimethylene carbonate
Trimethylene carbonate.png
Names
IUPAC name
1,3-Dioxan-2-one
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.114.239
UNII
Properties
C4H6O3
Molar mass 102.09 g·mol−1
Appearance white solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethylene carbonate or 1,3-propylene carbonate is a 6-membered cyclic carbonate ester. It is a colourless solid that upon heating or catalytic ring-opening[1] converts to the poly(trimethylene carbonate). Such polymers are called aliphatic polycarbonates are of interest for potential biomedical applications. An isomeric derivative is propylene carbonate, a colourless liquid that does not spontaneously polymerize.

Preparation[edit]

This compound may be prepared from 1,3-propanediol and ethyl chloroformate (a phosgene substitute), or from oxetane and carbon dioxide with an appropriate catalyst:[2]

HOC3H6OH + ClCO2C2H5 → C3H6O2CO + C2H5OH + HCl
C3H6O + CO2 → C3H6O2CO

This cyclic carbonate undergoes ring-opening polymerization to give poly(trimethylene carbonate), abbreviated PTC.[2] The polymer PTC is of commercial interest as a biodegradable polymer with biomedical applications.[3]

References[edit]

  1. ^ Chan, J. M. W.; Zhang, X.; Sardon, H.; Engler, A. C.; Fox, C. H.; Frank, C. W.; Waymouth, R. M.; Hedrick, J. L. (2015). "Organocatalytic Ring-Opening Polymerization of Trimethylene Carbonate to Yield a Biodegradable Polycarbonate". J. Chem. Educ. 92: 708–713. doi:10.1021/ed500595k. 
  2. ^ a b Pyo, Sang-Hyun; Persson, Per; Mollaahmad, M. Amin; Sörensen, Kent; Lundmark, Stefan; Hatti-Kaul, Rajni (2012). "Cyclic carbonates as monomers for phosgene- and isocyanate-free polyurethanes and polycarbonates". Pure Appl. Chem. 84 (3): 637. doi:10.1351/PAC-CON-11-06-14. 
  3. ^ Engelberg, Israel; Kohn, Joachim (1991). "Physicomechanical properties of degradable polymers used in medical applications: a comparative study". Biomaterials. 12 (3): 292–304. doi:10.1016/0142-9612(91)90037-B.