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Propionic anhydride

Chemical compound From Wikipedia, the free encyclopedia

Propionic anhydride
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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]

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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
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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.

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

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