2,2,4,4-Tetramethylcyclobutanedione

2,2,4,4-Tetramethylcyclobutanedione is the organic compound with the formula (CH3)4C4O2. The compound is a diketone of cyclobutane, bearing four methyl groups. It is a white solid that is used as a precursor to diverse industrial products.

2,2,4,4-Tetramethylcyclobutanedione
Names
Preferred IUPAC name
2,2,4,4-Tetramethylcyclobutane-1,3-dione
Other names
Tetramethyl-1,3-cyclobutanedione, Tetramethylcyclobuta-1,3-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.012.063
EC Number
  • 213-269-6
UNII
  • InChI=1S/C8H12O2/c1-7(2)5(9)8(3,4)6(7)10/h1-4H3
    Key: RGCDVHNITQEYPO-UHFFFAOYSA-N
  • CC1(C(=O)C(C1=O)(C)C)C
Properties
C8H12O2
Molar mass 140.182 g·mol−1
Appearance Colorless or white solid
Melting point 112–115 °C (234–239 °F; 385–388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis and reactions

2,2,4,4-Tetramethylcyclobutanedione is the head-to-tail dimer of dimethylketene. It arises spontaneously when dimethylketene is produced by dehydrohalogenation of isobutyryl chloride with triethylamine.[1]

The 2,2,4,4-tetramethylcyclobutanedione isomerizes to the lactone called dimethylketene dimer (4-isopropylidene-3,3-dimethyl-2-oxetanone).[2] Dimethylketene dimer is a precursor to various alkyl ketene dimers, which are used in papermaking.

Hydrogenation of 2,2,4,4-tetramethylcyclobutanedione gives 2,2,4,4-tetramethylcyclobutanediol, which is of interest in polymer chemistry.

References
  1. R. Huisgen, P. Otto (1968), "The mechanism of dimerization of dimethylketene", J. Am. Chem. Soc., vol. 90, no. 19, pp. 5342–5343, doi:10.1021/ja01021a090
  2. R.H. Hasek; R.D. Clark; G.L. Mayberry (1968). "Dimethylketene β-Lactone Dimer". Organic Syntheses. 48: 72. doi:10.15227/orgsyn.048.0072.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.