Trimethylene carbonate
 | |
| Names | |
|---|---|
| IUPAC name
1,3-Dioxan-2-one | |
| Identifiers | |
| 2453-03-4 | |
| ChemSpider | 110377 |
| |
| Jmol-3D images | Image |
| PubChem | 123834 |
| |
| Properties | |
| Molecular formula |
C4H6O3 |
| Molar mass | 102.09 g·mol−1 |
| Appearance | white solid |
| Except where noted otherwise, data is 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 converts to the polytrimethyl carbonate. Such polymers are of interest for biomedical applications. An isomeric derivative is propylene carbonate, a colourless liquid that does not spontaneously polymerize.
Preparation
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:[1]
- HOC3H6OH + ClCO2C2H5 → C3H6O2CO + C2H5OH + HCl
- C3H6O + CO2 → C3H6O2CO
This cyclic carbonate undergoes ring-opening polymerization to give poly(trimethylene carbonate), abbreviated PTC.[1] The polymer PTC is of commercial interest as a biodegradable polymer with biomedical applications.[2][3]
References
- ↑ 1.0 1.1 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.
- ↑ Engelberg, Israel; Kohn, Joachim "Physicomechanical properties of degradable polymers used in medical applications: a comparative study" Biomaterials 1991, volume 12(3), 292-304. http://dx.doi.org.proxy2.library.illinois.edu/10.1016/0142-9612(91)90037-B
- ↑ Höglund, Odd V; Ingman, Jessica; Södersten, Fredrik; Hansson, Kerstin; Borg, Niklas; Lagerstedt, Anne-Sofie (2014). "Ligation of the spermatic cord in dogs with a self-locking device of a resorbable polyglycolic based co-polymer – feasibility and long-term follow-up study" (PDF). BMC Research Notes 7 (1): 825. doi:10.1186/1756-0500-7-825.