Propionic_anhydride

Propionic anhydride

Propionic anhydride

Chemical compound

Propionic anhydride is an organic compound with the formula (CH3CH2CO)2O. This simple acid anhydride is a colourless liquid. It is a widely used reagent in organic synthesis as well as for producing specialty derivatives of cellulose.[1]

Quick Facts Names, Identifiers ...

Synthesis

Industrial route to propionic anhydride involves thermal dehydration of propionic acid, driving off the water by distillation:

2 CH3CH2CO2H → (CH3CH2CO)2O + H2O

Another routes is the Reppe carbonylation of ethylene with propionic acid and nickel carbonyl as the catalyst:[1]

CH2=CH2 + CH3CH2CO2H + CO → (CH3CH2CO)2O

Propionic anhydride has also been prepared by dehydration of propionic acid using ketene:[2]

2 CH3CH2CO2H + CH2=C=O → (CH3CH2CO)2O + CH3CO2H

Safety

Propanoic anhydride is strong smelling and corrosive, and will cause burns on contact with skin. Vapour can burn eyes and lungs.

Due to its potential use as a precursor in the synthesis of fentanyl and fentanyl analogs, propanoic anhydride is regulated by the United States Drug Enforcement Administration as a List I chemical under the Controlled Substances Act.[3]

References

  1. [1]
    Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3527306732.
  2. [2]
    Williams, J. W. Krynitsky, J. A. (1941). "n-Caproic Anhydride". Organic Syntheses. 21: 13. doi:10.15227/orgsyn.021.0013{{cite journal}}: CS1 maint: multiple names: authors list (link).
  3. [3]
    Drugs of Abuse Publication, Chapter 2 Archived 2007-12-20 at the Wayback Machine
Share this article:

This article uses material from the Wikipedia article Propionic_anhydride, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.