2,3-Dimethylmaleic anhydride

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2,3-Dimethylmaleic anhydride
DMMA.svg
Names
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 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 (Colocasia esculenta).

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