Glycolide

Glycolide
Names
IUPAC name
1,4-Dioxane-2,5-dione
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCard 100.007.232
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).
Infobox references

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. A more direct method is by self-condensation of the sodium salt of chloroacetic acid. It is useful as a starting material for the production of polyglycolide.