Propionic anhydride

Names
Preferred IUPAC name

Propanoic anhydride

Other names

Propionic anhydride
Propanoyl propanoate

Identifiers

CAS Number

* 123-62-6 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL3186472

ChemSpider |

* 29003 Y

EC Number |

* 204-638-2

PubChem CID

* 31263

RTECS number |

* UF9100000

UNII |

* E3A2VV18E6 Y

UN number | 2496

InChI

* 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

SMILES

* CCC(=O)OC(=O)CC

Properties

Chemical formula

| 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)

Solubility in water

| Reacts to give propanoic acid
Viscosity | 1.144 cP at ?°C
Hazards
Main hazards | flammable
Safety data sheet | External MSDS
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H314

GHS precautionary statements

| P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P405, P501
Flash point |  63 °C (145 °F; 336 K)
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).

N verify (what is YN ?)
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]

## Contents

* 1 Synthesis
* 2 Safety
* 3 Legal Status
* 4 References

## 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.

## 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

1. ↑ 1.0 1.1 Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223.
2. ↑ Williams, J. W. Krynitsky, J. A. (1941). "n-Caproic Anhydride". Organic Syntheses 21: 13. doi:10.15227/orgsyn.021.0013.
3. ↑ Drugs of Abuse Publication, Chapter 2

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*[CID]: Compound ID
*[H314]: Causes severe skin burns and eye damage
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P321]: Specific treatment (see … on this label)
*[P363]: Wash contaminated clothing before reuse
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …