Propionic anhydride
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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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
Safety
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]