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Propionic anhydride

Propanoyl propanoate Propanoyl chloride 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.

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

Propionic anhydride has also been prepared by dehydration of propionic acid using ketene: : 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.

Legal Status

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.

References

(2005). "Propionic Acid and Derivatives".
Williams, J. W. Krynitsky, J. A.. (1941). "n-Caproic Anhydride".
[http://www.dea.gov/pubs/abuse/2-chem.htm Drugs of Abuse Publication, Chapter 2] {{webarchive. link. (2007-12-20)

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

carboxylic-anhydrides lachrymatory-agents

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