Trimethylene carbonate
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |||
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| Preferred IUPAC name
1,3-Dioxan-2-one | |||
| Identifiers | |||
3D model (JSmol) |
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| ChemSpider | |||
| ECHA InfoCard | 100.114.239 | ||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| C4H6O3 | |||
| Molar mass | 102.089 g·molâ1 | ||
| Appearance | White solid | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 â C3H6O2CO + C2H5OH + HCl
- C3H6O + CO2 â 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]