Propionic anhydride
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Through Organic compound, Chemical formula and Reagent
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
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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.