Propionitrile

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Propionitrile
Skeletal formula of propanenitrile
Skeletal formula of propanenitrile with all explicit hydrogens added
Ball and stick model of propanenitrile
Names
IUPAC name
Propanenitrile[4]
Other names
Identifiers
773680
107-12-0 YesY
ChEMBL ChEMBL15871 N
ChemSpider 7566 YesY
EC number 203-464-4
Jmol-3D images Image
MeSH propionitrile
PubChem 7854
RTECS number UF9625000
UN number 2404
Properties
C3H5N
Molar mass 55.08 g·mol−1
Appearance Colourless liquid
Density 772 mg mL−1
Melting point −100 °C; −148 °F; 173 K
Boiling point 96 °C; 205 °F; 369 K
log P 0.176
Vapor pressure 270 μmol Pa−1 kg−1
1.366
Thermochemistry
105.3 J K−1 mol−1
189.33 J K−1 mol−1
15.5 kJ mol−1
−1.94884–−1.94776 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H300, H310, H319, H332
P210, P264, P280, P301+310, P302+350, P305+351+338
EU classification Highly Flammable F Very Toxic T+
R-phrases R11, R20, R25, R27, R36
S-phrases S16, S36/37, S45
Flash point 6 °C (43 °F; 279 K)
Explosive limits 3.1%-?[5]
39 mg kg−1 (oral, rat)
US health exposure limits (NIOSH):
none[5]
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

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.[6]

Production[edit]

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):[6]

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[edit]

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[edit]

Propanenitrile is poisonous but weakly with an LD50 of 230 mg/kg (rats, oral).[6] Propanenitrile has been determined to be teratogenic due to the metabolic release of cyanide.[7]

In 1979, the Kalama (Vega) plant in Beaufort, South Carolina experienced an explosion during the production of propanenitrile by nickel-catalyzed reduction of acrylonitrile.[8] This site is now one of the two Superfund cleanup sites in South Carolina.[8]

References[edit]

  1. ^ a b "Propionitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Identification. Retrieved 1 November 2013. 
  2. ^ Merck Index, 11th Edition, 7839
  3. ^ CRC Handbook of Chemistry and Physics, 52nd Ed., p. D-153
  4. ^ "propionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 6 June 2012. 
  5. ^ a b "NIOSH Pocket Guide to Chemical Hazards #0530". National Institute for Occupational Safety and Health (NIOSH). 
  6. ^ a b c 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
  7. ^ 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. 
  8. ^ a b First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina, United States Environmental Protection Agency

External links[edit]