Propionic anhydride
Names
Preferred IUPAC name
Propanoic anhydride
Other names
Propionic anhydride
Propanoyl propanoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.218
EC Number
  • 204-638-2
RTECS number
  • UF9100000
UNII
UN number 2496
  • InChI=1S/C6H10O3/c1-3-5(7)9-6(8)4-2/h3-4H2,1-2H3 ☒N
    Key: WYVAMUWZEOHJOQ-UHFFFAOYSA-N ☒N
  • InChI=1/C6H10O3/c1-3-5(7)9-6(8)4-2/h3-4H2,1-2H3
    Key: WYVAMUWZEOHJOQ-UHFFFAOYAJ
  • CCC(=O)OC(=O)CC
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:
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
 Acetic anhydride

Propanoyl chloride

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

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

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

  1. 1 2 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. ISBN 978-3527306732.
  2. ↑ Williams, J. W. Krynitsky, J. A. (1941). "n-Caproic Anhydride". Organic Syntheses. 21: 13. doi:10.15227/orgsyn.021.0013.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ↑ Drugs of Abuse Publication, Chapter 2 Archived 2007-12-20 at the Wayback Machine
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