Propionitrile

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Propionitrile
Skeletal formula of propanenitrile Propionitrile skeletal.png
Skeletal formula of propanenitrile
Skeletal formula of propanenitrile with all explicit hydrogens added Propionitrile simple.png
Skeletal formula of propanenitrile with all explicit hydrogens added
Ball and stick model of propanenitrile Propionitrile-3D-balls.png
Ball and stick model of propanenitrile
Names
Preferred IUPAC name
Propanenitrile [1]
Other names
Identifiers
3D model (JSmol)
773680
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.151 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-464-4
MeSH propionitrile
PubChem CID
RTECS number
  • UF9625000
UNII
UN number 2404
  • InChI=1S/C3H5N/c1-2-3-4/h2H2,1H3 Yes check.svgY
    Key: FVSKHRXBFJPNKK-UHFFFAOYSA-N Yes check.svgY
  • CCC#N
Properties
C3H5N
Molar mass 55.080 g·mol−1
AppearanceColourless 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
Std molar
entropy (S⦵298)
189.33 J K−1 mol−1
15.5 kJ mol−1
−1.94884–−1.94776 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg
Danger
H225, H300, H310, H319, H332
P210, P264, P280, P301+P310, P302+P350, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
3
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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 → CH3CH2C≡N + 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.

The nitrile aldol reaction with benzophenone, followed by reduction of the nitrile with lithium aluminium hydride gives 2-MDP. This agent possesses appetite suppressant and antidepressant properties.

Chemical structure of 2-MDP 2-MDP.svg
Chemical structure of 2-MDP

Safety

The toxicity LD50 of propionitrile is listed as 39 mg/kg [8] and as 230 my (both rats, oral). [7]

In 1979, the Kalama (Vega) plant in Beaufort, South Carolina experienced an explosion during the production of propionitrile by nickel-catalyzed hydrogenation 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. 1 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. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0530". National Institute for Occupational Safety and Health (NIOSH).
  7. 1 2 3 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. ↑ PubChem: Propionitrile NIOSH Toxicity Data . Retrieved 6 Jan 2022.
  9. 1 2 First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina, United States Environmental Protection Agency
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