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Chemical compound From Wikipedia, the free encyclopedia
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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Names | |
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Preferred IUPAC name
Propanoic anhydride | |
Other names
Propionic anhydride Propanoyl propanoate | |
Identifiers | |
3D model (JSmol) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.218 |
EC Number |
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PubChem CID |
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RTECS number |
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UNII | |
UN number | 2496 |
CompTox Dashboard (EPA) |
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Properties | |
C6H10O3 | |
Molar mass | 130.14 g/mol |
Appearance | Clear liquid, with a strong smell similar to vinegar |
Density | 1.015 g/cm3, liquid |
Melting point | −42 °C (−44 °F; 231 K) |
Boiling point | 167 to 170 °C (333 to 338 °F; 440 to 443 K) |
Reacts to give propanoic acid | |
Viscosity | 1.144 cP at ?°C |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
flammable |
GHS labelling: | |
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Danger | |
H314 | |
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501 | |
Flash point | 63 °C (145 °F; 336 K) |
Safety data sheet (SDS) | External MSDS |
Related compounds | |
Related compounds |
Acetic anhydride |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Industrial route to propionic anhydride involves thermal dehydration of propionic acid, driving off the water by distillation:
Another routes is the Reppe carbonylation of ethylene with propionic acid and nickel carbonyl as the catalyst:[1]
Propionic anhydride has also been prepared by dehydration of propionic acid using ketene:[2]
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]
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