Trimethylene carbonate explained

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.

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

Notes and References

  1. Chan. J. M. W.. Zhang. X.. Sardon. H.. Engler. A. C.. Fox. C. H.. Frank. C. W.. Waymouth. R. M.. Hedrick. J. L.. Organocatalytic Ring-Opening Polymerization of Trimethylene Carbonate to Yield a Biodegradable Polycarbonate. J. Chem. Educ.. 2015. 92. 4 . 708–713. 10.1021/ed500595k. 2015JChEd..92..708C .
  2. Pure Appl. Chem. . 10.1351/PAC-CON-11-06-14 . Cyclic carbonates as monomers for phosgene- and isocyanate-free polyurethanes and polycarbonates . 2012 . Pyo . Sang-Hyun . Persson . Per . Mollaahmad . M. Amin . Sörensen . Kent . Lundmark . Stefan . Hatti-Kaul . Rajni . 84 . 3 . 637. free.
  3. Engelberg . Israel . Kohn . Joachim . 1991 . Physicomechanical properties of degradable polymers used in medical applications: a comparative study . Biomaterials . 12 . 3. 292–304 . 10.1016/0142-9612(91)90037-B . 1649646 .
  4. Katz . AR . Mukherjee . DP . Kaganov . AL . Gordon . S . A new synthetic monofilament absorbable suture made from polytrimethylene carbonate. . Surgery, Gynecology & Obstetrics . September 1985 . 161 . 3 . 213–22 . 3898441.
  5. Nylund . Adam M. . Chen . Chi-Ya . Höglund . Odd V. . Campbell . Bonnie G. . Fransson . Boel A. . Evaluation of a resorbable self-locking ligation device for performing peripheral lung biopsies in a caprine cadaveric model . Veterinary Surgery . July 2019 . 48 . 5 . 845–849 . 10.1111/vsu.13171. 30682213 . 59274389 .
  6. Nylund . Adam M. . Höglund . Odd V. . Fransson . Boel A. . Thoracoscopic-assisted lung lobectomy in cat cadavers using a resorbable self-locking ligation device . Veterinary Surgery . 15 October 2018 . 48 . 4 . 563–569 . 10.1111/vsu.13109. 30320472 . 52979661.
  7. da Mota Costa . Matheus Roberto . de Abreu Oliveira . André Lacerda . de Moura Vidal . Leonardo Waldstein . Moran Ramos . Renato . de Oliveira Campos . Ingrid . Hansson . Kerstin . Ley . Charles J . Olsson . Ulf . Borg . Niklas Olov . Höglund . Odd Viking . Comparison of macroscopic resorption time for a self-locking device and suture material in ovarian pedicle ligation in dogs . Veterinary Record . 13 April 2019 . 184 . 15 . 478 . 10.1136/vr.104732. free . 30872363 .
  8. Guedes . Rogério Luizari . Höglund . Odd Viking . Brum . Juliana Sperotto . Borg . Niklas . Dornbusch . Peterson Triches . Resorbable Self-Locking Implant for Lung Lobectomy Through Video-Assisted Thoracoscopic Surgery: First Live Animal Application . Surgical Innovation . 3 January 2018 . 25 . 2 . 158–164 . 10.1177/1553350617751293. 29298608 . 4965005.

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