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Lactic acid O-carboxyanhydride

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Lactic acid O-carboxyanhydride
Names
IUPAC name 5-Methyl-1,3-dioxolane-2,4-dione
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.116.276 Edit this at Wikidata
EC Number
  • 605-761-8
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4O4/c1-2-3(5)8-4(6)7-2/h2H,1H3Key: JLXQJNCZXSYXAK-UHFFFAOYSA-N
  • InChI=1/C4H4O4/c1-2-3(5)8-4(6)7-2/h2H,1H3Key: JLXQJNCZXSYXAK-UHFFFAOYAX
SMILES
  • O=C1OC(=O)OC1C
Properties
Chemical formula C4H4O4
Molar mass 116.072 g·mol
Melting point 28 °C (82 °F; 301 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Lactic acid O-carboxyanhydride (lac-OCA) is an organic compound. It is used as a monomer equivalent to lactic acid or lactide in the preparation of poly(lactic acid). When this monomer undergoes ring-opening polymerization, one equivalent of carbon dioxide gas is released for every lactic acid unit incorporated into the polymer:

This compound is prepared by treatment of lactic acid or its salts with phosgene or one of its equivalents, e.g. diphosgene.

References

  1. ^ Kricheldorf, Hans R.; Jonté, J. Michael (1983). "New polymer syntheses". Polymer Bulletin. 9 (6–7): 276–283. doi:10.1007/BF00262719.
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