Trimethylene carbonate

Trimethylene carbonate
Names
	IUPAC name 1,3-Dioxan-2-one
Identifiers
CAS Number	2453-03-4;
3D model (JSmol)	Interactive image;
ChemSpider	110377;
ECHA InfoCard	100.114.239
PubChem CID	123834;
UNII	4316AQ174Q ;
	InChI InChI=1S/C4H6O3/c5-4-6-2-1-3-7-4/h1-3H2 Key: YFHICDDUDORKJB-UHFFFAOYSA-N; InChI=1/C4H6O3/c5-4-6-2-1-3-7-4/h1-3H2 Key: YFHICDDUDORKJB-UHFFFAOYAZ;
	SMILES O=C1OCCCO1;
Properties
Chemical formula	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

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

↑ 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.
1 2 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 (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.

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[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.

[pyo-2] 1 2 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.