p-Dioxanone

p-Dioxanone (1,4-dioxan-2-one) is the lactone of 2-(2-hydroxyethoxy)acetic acid. It is a monomer that can undergo ring-opening polymerization to give polydioxanone, a biodegradable implant material.[1] It is isomeric to trimethylene carbonate (1,3-dioxan-2-one).

p-Dioxanone
Names
Preferred IUPAC name
1,4-Dioxan-2-one
Other names
para-Dioxanone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.130.057
UNII
  • InChI=1S/C4H6O3/c5-4-3-6-1-2-7-4/h1-3H2
    Key: VPVXHAANQNHFSF-UHFFFAOYSA-N
  • InChI=1S/C4H6O3/c5-4-3-6-1-2-7-4/h1-3H2
    Key: VPVXHAANQNHFSF-UHFFFAOYSA-N
  • C1COC(=O)CO1
Properties
C4H6O3
Molar mass 102.089 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

The common synthetic process for p-dioxanone is continuous gas-phase dehydrogenation of diethylene glycol on a copper or copper chromite catalyst at 280 °C.

This gives yields of up to 86%. Removal of excess diethylene glycol is crucial to the stability of the product as a monomer.[2] Further purification with recrystallization, vacuum distillation,[3] or melt crystallization[2] allows purities of >99.5% to be achieved.

Properties

Pure p-dioxanone is a white crystalline solid with a melting point of 28 °C.[4]

Uses

The oxidation of p-dioxanone with nitric acid or dinitrogen tetroxide gives diglycolic acid at 75% yield.[5]

p-Dioxanone can undergo ring-opening polymerization catalyzed by organic compounds of tin, such as tin(II) octoate[6] or dibutyltin dilaurate, or by basic alkoxides such as aluminium isopropoxide. This affords polydioxanone, a biodegradable, semicrystalline and thermally labile polymer with uses in industry and medicine.[7] Depolymerization back to the monomer is triggered at 100 °C.

References
  1. Sangamesh Kumbar, Cato Laurencin and Meng Deng, ed. (20 February 2014). Polymeric Biomaterials in Tissue Engineering and Regenerative Medicine. ISBN 978-0-12-396983-5. {{cite book}}: |work= ignored (help)
  2. US 5675022, "Recovery of dioxanone by melt crystallization", published 1995-08-23, issued 1997-10-07
  3. US 2142033, "Process for the production of 2-p-dioxanone", published 1936-07-01, issued 1938-10-27
  4. Lee, Sang-Won; Kim, Sung-Il; Park, So-Jin (2008). "Solubility and density of p-dioxanone in organic solvent systems" (PDF). J. Korean Oil Chem. Soc. 25 (4): 429–437.
  5. US 3952054, Shen, C.Y., "Process for preparing diglycolic acid", issued 1976-04-20
  6. US 3645941, "Method of preparing 2-p-dioxanone polymers", issued 1972-02-09
  7. Bezwada, R.S.; Jamiolkowski, D.D.; Cooper, K. (1997). "Poly(p-dioxane) and its copolymers". Handbook of biodegradable polymers. A. J. Domb, Joseph Kost, David M. Wiseman. Australia: Harwood Academic Publishers. pp. 29–61. ISBN 90-5702-153-6. OCLC 38861271.


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