Methacrylic anhydride
Names
Preferred IUPAC name
2-Methylprop-2-enoic anhydride
Other names
Methacrylic anhydride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.986
UNII
  • InChI=1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3
    Key: DCUFMVPCXCSVNP-UHFFFAOYSA-N
  • InChI=1/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3
    Key: DCUFMVPCXCSVNP-UHFFFAOYAX
  • O=C(OC(=O)\C(=C)C)\C(=C)C
Properties
C8H10O3
Molar mass 154.165 g·mol−1
Density 1.035 g/cm3
Boiling point 87 °C/13 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methacrylic anhydride is a liquid which reacts with water exothermically.[1]

It can also react with hydroxyl- and amino-groups present in some organic compounds leading to covalent attachment of methacryloyl moieties. These functional groups could be successfully used either in subsequent polymerisation or reactions with thiols. For example, chitosan modified by methacryloylation exhibits better ability to adhere to mucosal surfaces (mucoadhesion) due to its reactivity with thiols groups present in cysteine domains of mucins ).[2]

Uses

Methacrylic anhydride is used as an intermediate agent in plastics material and resin manufacturing. [3]

References

  1. ↑ Methacrylic anhydride at www.chemicalbook.com.
  2. ↑ Kolawole, Oluwadamilola M.; Lau, Wing Man; Khutoryanskiy, Vitaliy V. (2018-10-25). "Methacrylated chitosan as a polymer with enhanced mucoadhesive properties for transmucosal drug delivery" (PDF). International Journal of Pharmaceutics. 550 (1): 123–129. doi:10.1016/j.ijpharm.2018.08.034. ISSN 0378-5173. PMID 30130604. S2CID 52055140.
  3. ↑ "Methacrylic anhydride". PubChem. National Institute of Health. Retrieved 2023-01-20.
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