Propionic anhydride
| Names | |
|---|---|
| Preferred IUPAC name
Propanoic anhydride | |
| Other names
Propionic anhydride
Propanoyl propanoate | |
| Identifiers | |
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| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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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
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flammable |
| GHS labelling: | |
| GHS05: Corrosive | |
| 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
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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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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]
Synthesis
[edit | edit source]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
Safety
[edit | edit source]Propanoic anhydride is strong smelling and corrosive, and will cause burns on contact with skin. Vapour can burn eyes and lungs.
Legal Status
[edit | edit source]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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- ^ Drugs of Abuse Publication, Chapter 2 Archived 2007-12-20 at the Wayback Machine
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