Diketene

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Diketene
IUPAC name Acetyl ketene
Identifiers
CAS number [674-82-8]
Properties
Molecular formula C4H4O2
Molar mass 84.08 g/mol
Density 1.09 g/cm³
Melting point

- 7 °C
Boiling point

127 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Diketene is an organic compound formed by dimerization of ketene. Diketene is a member of the oxetane family. It is used as a chemical reagent in organic chemistry[1]. It is a colorless liquid and heating regenerates the ketene monomer.

Alkylated ketenes also dimerize with ease and form substituted diketenes. Diketenes react with alcohols and amines to the corresponding acetoacetic acids. An example is the reaction with 2-aminoindane[2]

Diketene reaction Sai 2007

Certain diketenes with two aliphatic chains are used industrially to improve hydrophobicity in paper.

[edit] References

This article is based on a translation of an article from the German Wikipedia.

  1. ^ Beilstein E III/IV 17: 4297
  2. ^ Knorr Cyclizations and Distonic Superelectrophiles Kiran Kumar Solingapuram Sai, Thomas M. Gilbert, and Douglas A. Klumpp J. Org. Chem. 2007, 72, 9761-9764 doi:10.1021/jo7013092