Propionitrile

Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.[7]

Propionitrile
Skeletal formula of propanenitrile
Skeletal formula of propanenitrile with all explicit hydrogens added
Names
IUPAC name
Propanenitrile[1]
Other names
Identifiers
3D model (JSmol)
773680
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.151
EC Number
  • 203-464-4
MeSH propionitrile
RTECS number
  • UF9625000
UNII
UN number 2404
Properties
C3H5N
Molar mass 55.080 g·mol−1
Appearance Colourless liquid
Odor sweetish, pleasant, ethereal[6]
Density 772 mg mL−1
Melting point −100 to −86 °C; −148 to −123 °F; 173 to 187 K
Boiling point 96 to 98 °C; 205 to 208 °F; 369 to 371 K
11.9% (20 °C)[6]
log P 0.176
Vapor pressure 270 μmol Pa−1 kg−1
-38.5·10−6 cm3/mol
1.366
Thermochemistry
105.3 J K−1 mol−1
189.33 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 15.5 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −1.94884–−1.94776 MJ mol−1
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H300, H310, H319, H332
P210, P264, P280, P301+310, P302+350, P305+351+338
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 4: Very short exposure could cause death or major residual injury. E.g. VX gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
4
0
Flash point 6 °C (43 °F; 279 K)
Explosive limits 3.1%-?[6]
Lethal dose or concentration (LD, LC):
39 mg kg−1 (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[6]
REL (Recommended)
 TWA 6 ppm (14 mg/m3)[6]
IDLH (Immediate danger)
 N.D.[6]
Related compounds
Related alkanenitriles
Related compounds
 DBNPA
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

Production

The main industrial route to this nitrile is the hydrogenation of acrylonitrile. It is also prepared by the ammoxidation of propanol (propionaldehyde can also be used instead):[7]

CH3CH2CH2OH + O2 + NH3 → CH3CH2CN + 3 H2O

Propionitrile is a byproduct of the electrodimerisation of acrylonitrile to adiponitrile.

In the laboratory propanenitrile can also be produced by the dehydration of propionamide, by catalytic reduction of acrylonitrile, or by distilling ethyl sulfate and potassium cyanide.

Applications

Propionitrile is a solvent similar to acetonitrile but with a slightly higher boiling point. It is a precursor to propylamines by hydrogenation. It is a C-3 building block in the preparation of the drug flopropione by the Houben-Hoesch reaction.

Safety

Propanenitrile is poisonous but weakly with an LD50 of 230 mg/kg (rats, oral).[7] Propanenitrile has been determined to be teratogenic due to the metabolic release of cyanide.[8]

In 1979, the Kalama (Vega) plant in Beaufort, South Carolina experienced an explosion during the production of propanenitrile by nickel-catalyzed reduction of acrylonitrile.[9] This site is now one of the two Superfund cleanup sites in South Carolina.[9]

References
  1. "propionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 6 June 2012.
  2. "Propionitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Identification. Retrieved 1 November 2013.
  3. Merck Index, 11th Edition, 7839
  4. CRC Handbook of Chemistry and Physics, 52nd Ed., p. D-153
  5. HSDB: Propionitrile, TOXNET, U.S. National Library of Medicine, retrieved 30 Oct 2015
  6. NIOSH Pocket Guide to Chemical Hazards. "#0530". National Institute for Occupational Safety and Health (NIOSH).
  7. Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363
  8. Willhite, Calvin C.; Ferm, Vergil H.; Smith, Roger P. (1981). "Teratogenic effects of aliphatic nitriles". Teratology. 23 (3): 317–323. doi:10.1002/tera.1420230306. PMID 6266064.
  9. First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina, United States Environmental Protection Agency
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