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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 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.

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:

HOC<sub>3</sub>H<sub>6</sub>OH + ClCO<sub>2</sub>C<sub>2</sub>H<sub>5</sub> → C<sub>3</sub>H<sub>6</sub>O<sub>2</sub>CO + C<sub>2</sub>H<sub>5</sub>OH + HCl
C<sub>3</sub>H<sub>6</sub>O + CO<sub>2</sub> → C<sub>3</sub>H<sub>6</sub>O<sub>2</sub>CO

This cyclic carbonate undergoes ring-opening polymerization to give poly(trimethylene carbonate), abbreviated PTMC.

Medical devices

The polymer PTC is of commercial interest as a biodegradable polymer with biomedical applications. 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. The same material is used in other resorbable medical devices.

See also

References