2,3-Dimethylmaleic anhydride

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2,3-Dimethylmaleic anhydride
DMMA.svg
Names
Preferred IUPAC name
2,3-Dimethylfuran-2,5-dione
Other names
DMMA
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.011.059 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 212-165-8
PubChem CID
UNII
  • InChI=1S/C6H6O3/c1-3-4(2)6(8)9-5(3)7/h1-2H3
    Key: MFGALGYVFGDXIX-UHFFFAOYSA-N
  • CC1=C(C(=O)OC1=O)C
Properties
C6H6O3
Molar mass 126.111 g·mol−1
AppearanceColorless solid
Density 1.107 g/cm3
Melting point 96 °C (205 °F; 369 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,3-Dimethylmaleic anhydride is an organic compound with the formula (CH3)2C2(CO)2O. [1] It is related to maleic anhydride (MA) by replacement of the two CH units with CCH3 groups. It is the anhydride of 2,3-dimethylmaleic acid.

Synthesis

The compound can be prepared from two equivalents of MA in the presence of various amines, such as 2-aminopyridine, followed by treatment with sulfuric acid. [2] [3] It has been evaluated as a comonomer. [4] It occurs in some plants such as Colocasia esculenta .

Chemical structure of an intermediate in the 2-aminopyridine-catalyzed conversion of maleic anhydride to dimethylmaleic anhydride. Me2MaleicIntermediate.svg
Chemical structure of an intermediate in the 2-aminopyridine-catalyzed conversion of maleic anhydride to dimethylmaleic anhydride.

References

  1. ↑ Argade, Narshinha; Deore, Prashant; Haval, Kishan; Gadre, Smita (2014). "A Concise Account of the Chemistry of Valuable Alkyl(methyl)maleic Anhydrides". Synthesis. 46 (20): 2683–2700. doi:10.1055/s-0034-1378665.
  2. 1 2 Baumann, Marcus E.; Bosshard, Hans; Breitenstein, Werner; Rihs, Grety; Winkler, Tammo (1984). "Mechanismus der decarboxylativen Dimerisierung von Maleinsäureanhydrid zu Dimethylmaleinsäureanhydrid unter Einfluss von 2-Aminopyridin". Helvetica Chimica Acta. 67 (7): 1897–1905. doi:10.1002/hlca.19840670728.
  3. ↑ Hood, David K. (2024). "Maleic Anhydride, Maleic Acid, and Fumaric Acid". Kirk-Othmer Encyclopedia of Chemical Technology. pp. 1–51. doi:10.1002/0471238961.1301120506051220.a01.pub3. ISBN   978-0-471-48494-3.
  4. ↑ Florianczyk, T.; Sullivan, C.; Janovic, Z.; Vogl, O. (1981). "Alternating copolymers of dimethylmaleic anhydride". Polymer Bulletin. 5–5 (9–10). doi:10.1007/BF00254359.
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