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Propionitrile

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Propionitrile

Propionitrile
Skeletal formula of propanenitrile Skeletal formula of propanenitrile with all explicit hydrogens added
Ball and stick model of propanenitrile
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
EC number
UN number 2404
MeSH
ChEMBL  N
RTECS number UF9625000
Beilstein Reference 773680
Jmol-3D images Image 1
Properties
Molecular formula C3H5N
Molar mass 55.08 g mol−1
Appearance Colourless liquid
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
log P 0.176
Vapor pressure 270 μmol Pa−1 kg−1
Refractive index (nD) 1.366
Thermochemistry
Specific
heat capacity
C
105.3 J K−1 mol−1
Std molar
entropy
So298
189.33 J K−1 mol−1
Std enthalpy of
formation
ΔfHo298
15.5 kJ mol−1
Std enthalpy of
combustion
ΔcHo298
−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
GHS hazard statements H225, H300, H310, H319, H332
GHS precautionary statements 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)
LD50 39 mg kg−1 (oral, rat)
Related compounds
Related alkanenitriles
Related compounds DBNPA
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Propionitrile, also known as ethyl cyanide and propanenitrile, is an [5]

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):[5]

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).[5] Propanenitrile has been determined to be teratogenic due to the metabolic release of cyanide.[6]

In 1979, the Kalama (Vega) plant in Beaufort, South Carolina experienced an explosion during the production of propanenitrile by nickel-catalyzed reduction of acrylonitrile.[7] This site is now one of the two Superfund cleanup sites in South Carolina.[7]

References

  1. ^ "propionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 6 June 2012. 
  2. ^ a b "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. ^ 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
  6. ^ Willhite, Calvin C.; Ferm, Vergil H.; Smith, Roger P. (1981). "Teratogenic effects of aliphatic nitriles". Teratology 23 (3): 317–323.  
  7. ^ a b First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina, United States Environmental Protection Agency

External links

  • NIST Chemistry WebBook for C3H5N
  • CDC - NIOSH Pocket Guide to Chemical Hazards
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