Propionic anhydride
Names | |
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Preferred IUPAC name
Propanoic anhydride | |
Other names
Propionic anhydride
Propanoyl propanoate | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.004.218 |
PubChem CID
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RTECS number |
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UNII | |
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 | |
Main hazards | flammable |
Safety data sheet | External MSDS |
R-phrases (outdated) | R34 |
S-phrases (outdated) | S26-45 |
Flash point | 63 °C (145 °F; 336 K) |
Related compounds | |
Related compounds
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Acetic anhydride
Propanoyl chloride |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
what is ?) | (|
Infobox references | |
Propanoic 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]
Synthesis[]
Industrial route to propionic anhydride involves thermal dehydration, 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.
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.[3]
References[]
- ^ Jump up to: a b 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.
- ^ Williams, J. W. Krynitsky, J. A. (1955). "n-Caproic Anhydride". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 3
- ^ Drugs of Abuse Publication, Chapter 2 Archived 2007-12-20 at the Wayback Machine
- Carboxylic anhydrides
- Lachrymatory agents