Propionitrile

Propionitrile

Names
IUPAC name Propanenitrile[1]
Other names Cyanoethane[2] Ethyl cyanide[2] Propionitrile[3][4] Propylnitrile
Identifiers
Beilstein Reference	773680
CAS Registry Number	107-12-0 Y
ChEBI	CHEBI:26307
ChEMBL	ChEMBL15871 N
ChemSpider	7566 Y
EC number	203-464-4
InChI InChI=1S/C3H5N/c1-2-3-4/h2H2,1H3 Y Key: FVSKHRXBFJPNKK-UHFFFAOYSA-N Y
Jmol-3D images	Image
MeSH	propionitrile
PubChem	7854
RTECS number	UF9625000
SMILES CCC#N
UN number	2404
Properties
Molecular formula	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
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
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	F 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]
LD50 (Median lethal dose)	39 mg kg−1 (oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)	none[5]
Related compounds
Related alkanenitriles	Acetonitrile Aminopropionitrile Malononitrile Pivalonitrile Butyronitrile Succinonitrile
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 is: Y/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

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

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).^[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

External links

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

Molecules detected in outer space Molecules Diatomic Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argon hydride Carbon monophosphide Carbon monosulfide Carbon monoxide Carborundum Cyanogen radical Diatomic carbon Fluoromethylidynium Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride cation Methylidyne radical Nitric oxide Nitrogen (molecular) Nitrogen monohydride Nitrogen sulfide Oxygen (molecular) Phosphorus monoxide Phosphorus nitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium oxide Triatomic Aluminium hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Ethynyl radical Formyl radical Hydrogen cyanide Hydrogen isocyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical N2H+ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide Silicon naphthalocyanine Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Four atoms Acetylene Ammonia Cyanic acid Cyanoethynyl Cyclopropynylidyne Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Methylene amidogen Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon sulfide Thiocyanic acid Five atoms Ammonium Ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Seven atoms Acetaldehyde Acrylonitrile Cyanodiacetylene Ethylene oxide Hexatriynyl radical Methylacetylene Methylamine Vinyl alcohol Eight atoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienyl radical Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal Nine atoms Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile Ten atoms or more Acetone Benzene Buckminsterfullerene (C60 fullerene) ("bucky-ball") C70 fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine Deuterated molecules Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Methylacetylene N2D+ Trihydrogen cation Unconfirmed Anthracene Dihydroxyacetone Ethyl methyl ether Glycine Graphene H2NCO+ Linear C5 Naphthalene cation Phosphine Pyrene Silylidine Related Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Helium hydride ion Homochirality Intergalactic dust Interplanetary medium Interstellar medium Iron–sulfur world theory Kerogen Life Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Panspermia Polycyclic aromatic hydrocarbon (PAH) RNA world hypothesis Spectroscopy Tholin Book:Chemistry Category:Astrochemistry Category:Molecules Portal:Astrobiology Portal:Chemistry