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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
Names
IUPAC name
Propanenitrile
Other names
  • Cyanoethane
  • Ethyl cyanide
  • Propionitrile
  • Propylnitrile
Identifiers
107-12-0 YesY
3D model (Jmol) Interactive image
773680
ChEBI CHEBI:26307
ChEMBL ChEMBL15871 N
ChemSpider 7566 YesY
ECHA InfoCard 100.003.151
EC Number 203-464-4
MeSH propionitrile
PubChem 7854
RTECS number UF9625000
UNII E16N05FX3S YesY
UN number 2404
Properties
C3H5N
Molar mass 55.08 g·mol−1
Appearance Colourless liquid
Odor sweetish, pleasant, ethereal
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)
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
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
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%-?
Lethal dose or concentration (LD, LC):
LD50 (median dose)
39 mg kg−1(oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
none
REL (Recommended)
TWA 6 ppm (14 mg/m3)
IDLH (Immediate danger)
N.D.
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  (what is YesYN ?)
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.

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):

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.

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.

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

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


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Wikipedia

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