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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]

Production

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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

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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.

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Chemical structure of 2-MDP

Safety

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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

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^ ^a ^b "Propionitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Identification. Retrieved 1 November 2013.
^ Merck Index, 11th Edition, 7839
^ CRC Handbook of Chemistry and Physics, 52nd Ed., p. D-153
^ HSDB: Propionitrile, TOXNET, U.S. National Library of Medicine, retrieved 30 Oct 2015
^ "propionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 6 June 2012.
^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0530". National Institute for Occupational Safety and Health (NIOSH).
^ ^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
^ PubChem: Propionitrile NIOSH Toxicity Data. Retrieved 6 Jan 2022.
^ ^a ^b First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina, United States Environmental Protection Agency

External links

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Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Imidogen Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur mononitride Sulfur monoxide Titanium(II) oxide	👁 Image 👁 Image 👁 Image
Triatomic	Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene Methylidynephosphane N₂H⁺ Nitrous oxide Nitroxyl Ozone Potassium cyanide Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Trihydrogen cation Water
Four atoms	Acetylene Ammonia Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methyl cation Methyl radical Methylene amidogen Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thiocyanic acid Thioformaldehyde Tricarbon monosulfide Tricarbon monoxide
Five atoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Six atoms	Acetonitrile Cyanobutadiynyl radical Cyclopropenone Diacetylene E-Cyanomethanimine Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methyl isocyanate Methylamine Propyne Vinyl alcohol
Eight atoms	Acetic acid Acrolein Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methyl formate Methylcyanoacetylene
Nine atoms	Acetamide Cyanohexatriyne Dimethyl ether Ethanethiol Ethanol Methyldiacetylene N-Methylformamide Octatetraynyl radical Propene
Ten atoms or more	Acetone Benzene Benzonitrile Buckminsterfullerene (C₆₀, C₆₀⁺, fullerene, buckyball) Butyronitrile C₇₀ fullerene Cyanodecapentayne Cyclopentindene Ethyl formate Ethylene glycol Heptatrienyl radical Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Pyrimidine