Trimethylene carbonate, or 1,3-propylene carbonate, is a 6-membered cyclic

carbonate ester In organic chemistry, a carbonate ester (organic carbonate or organocarbonate) is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is and they ...

. It is a colourless solid that upon heating or catalytic ring-opening converts to

poly(trimethylene carbonate) Poly(trimethylene carbonate) (PTMC) is an aliphatic polycarbonate synthesized from the 6-membered cyclic carbonate, trimethylene carbonate (1,3-propylene carbonate or 1,3-Dioxan-2-one). Trimethylene carbonate (TMC) is a colorless crystalline so ...

(PTMC). Such polymers are called aliphatic polycarbonates and are of interest for potential biomedical applications. An isomeric derivative is

propylene carbonate Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol. This colorless and odorless liquid is useful as a polar, aprotic solvent. Propylene carbonat ...

, a colourless liquid that does not spontaneously polymerize.

Preparation

This compound may be prepared from 1,3-propanediol and

ethyl chloroformate Ethyl chloroformate is the ethyl ester of chloroformic acid. It is a reagent used in organic synthesis for the introduction of the ethyl carbamate protecting group and for the formation of carboxylic anhydrides. Preparation Ethyl chloroforma ...

(a phosgene substitute), or from

oxetane Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula , having a four-membered ring with three carbon atoms and one oxygen atom. The term "an oxetane" or "oxetanes" refer to any organic compound containing ...

and

carbon dioxide Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...

with an appropriate catalyst: :HOC₃H₆OH + ClCO₂C₂H₅ → C₃H₆O₂CO + C₂H₅OH + HCl :C₃H₆O + CO₂ → C₃H₆O₂CO This cyclic carbonate undergoes ring-opening polymerization to give poly(trimethylene carbonate), abbreviated PTMC. : TCM_polymerization

Medical devices

The polymer PTC is of commercial interest as a biodegradable polymer with biomedical applications. A block copolymer of

glycolic acid Glycolic acid (or hydroxyacetic acid; chemical formula HOCH2CO2H) is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water. It is used in various skin-care products. Glycolic acid is widespread in nature. A glycolate (so ...

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.

References

{{reflist Carbonate esters Monomers

Preparation

Medical devices

See also

References