2,2,4,4-Tetramethylcyclobutanedione Explained

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.

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.

In the presence of aluminium trichloride, 2,2,4,4-tetramethylcyclobutanedione isomerizes to the lactone dimethylketene dimer (4-isopropylidene-3,3-dimethyl-2-oxetanone).[1] 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. Organic Syntheses. R.H. Hasek. R.D. Clark. G.L. Mayberry . Dimethylketene β-Lactone Dimer . 1968 . 48 . 72 . 10.15227/orgsyn.048.0072.