Lactic acid O-carboxyanhydride

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:[1]

Lactic acid O-carboxyanhydride
Names
IUPAC name
5-Methyl-1,3-dioxolane-2,4-dione
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.116.276
EC Number
  • 605-761-8
  • InChI=1S/C4H4O4/c1-2-3(5)8-4(6)7-2/h2H,1H3
    Key: JLXQJNCZXSYXAK-UHFFFAOYSA-N
  • InChI=1/C4H4O4/c1-2-3(5)8-4(6)7-2/h2H,1H3
    Key: JLXQJNCZXSYXAK-UHFFFAOYAX
  • O=C1OC(=O)OC1C
Properties
C4H4O4
Molar mass 116.072 g·mol−1
Melting point 28 °C (82 °F; 301 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

This compound is prepared by treatment of lactic acid or its salts with phosgene or one of its equivalents, e.g. diphosgene.[1]

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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