Trimethylene carbonate

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 poly(trimethylene carbonate) (PTMC). Such polymers are called aliphatic polycarbonates and are of interest for potential biomedical applications. An isomeric derivative is propylene carbonate, a colourless liquid that does not spontaneously polymerize.

Trimethylene carbonate

Names
Preferred 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 Y
CompTox Dashboard (EPA)	DTXSID20953766
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	102.089 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

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 PTMC.^[2]

Medical devices

The polymer PTC is of commercial interest as a biodegradable polymer with biomedical applications.^[3] A block copolymer of glycolic acid and trimethylene carbonate (TMC) is the material of the Maxon suture, a monofilament resorbable suture which was introduced in the mid-1980s.^[4] The same material is used in other resorbable medical devices.^[5][6][7][8]

See also

• Ethylene carbonate