Glycolide

Glycolide
Names
IUPAC name
1,4-Dioxane-2,5-dione
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCard 100.007.232 Edit this at Wikidata
EC Number
  • 207-954-9
UNII
  • InChI=1S/C4H4O4/c5-3-1-7-4(6)2-8-3/h1-2H2
    Key: RKDVKSZUMVYZHH-UHFFFAOYSA-N
  • O=C1COC(=O)CO1
Properties
C4H4O4
Molar mass 116.072 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glycolide (1,4-dioxane-2,5-dione) is a dimer of glycolic acid. Its structure is six-membered ring containing two lactones, an oxidized variant of p-dioxane. The compound can be synthesized from glycolic acid, via a high-temperature oligomerization to form polyglycolide followed by a depolymerization process.[1][2] A more direct method is by self-condensation of the sodium salt of chloroacetic acid.[3] It is useful as a starting material for the production of polyglycolide.[4]

References

  1. ^ Andreas, Friedrich; Sowada, Rudolf; Scholz, Joachim (1962). "Darstellung und Eigenschaften von Glykolid". Journal für Praktische Chemie. 18 (3–4): 141–149. doi:10.1002/prac.19620180305.
  2. ^ Bischoff, C. A.; Walden, P. (1893). "Ueber das Glycolid und seine Homologen". Berichte der Deutschen Chemischen Gesellschaft. 26: 262–265. doi:10.1002/cber.18930260158.
  3. ^ Sporzyński, A.; Kocay, W.; Briscoe, H. V. A. (1949). "A new method of preparing glycollide". Recueil des Travaux Chimiques des Pays-Bas. 68 (7): 613–618. doi:10.1002/recl.19490680705.
  4. ^ Synthetic Biodegradable Polymers. Advances in Polymer Science. Vol. 245. 2012. doi:10.1007/978-3-642-27154-0. ISBN 978-3-642-27153-3.
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