Propionitrile, also known as ethyl cyanide and propanenitrile, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula CH₃CH₂CN. It is a simple aliphatic

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...

. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.

Production

The main industrial route to this nitrile is the hydrogenation of

acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group () linked to a nitrile (). It is an im ...

. It is also prepared by the

ammoxidation In organic chemistry, ammoxidation is a process for the production of nitriles () using ammonia () and oxygen (). It is sometimes called the SOHIO process, acknowledging that ammoxidation was developed at Standard Oil of Ohio. The usual substrate ...

propanol There are two isomers of propanol. * 1-Propanol, ''n''-propanol, or propan-1-ol: CH3CH2CH2OH, the most common meaning *2-Propanol, isopropyl alcohol, isopropanol, or propan-2-ol: (CH3)2CHOH See also * Propanal (propionaldehyde) differs in spel ...

(propionaldehyde can also be used instead):Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. : Propionitrile is a byproduct of the electrodimerisation of acrylonitrile to

adiponitrile Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.M. T. Musser, "Adipi ...

. In the laboratory propanenitrile can also be produced by the

dehydration In physiology, dehydration is a lack of total body water that disrupts metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of water. Mild deh ...

propionamide Propanamide has the chemical formula CH3CH2C=O(NH2). It is the amide of propanoic acid. This organic compound is a mono-substituted amide. Organic compounds of the amide group can react in many different organic processes to form other useful c ...

, by catalytic reduction of

, or by distilling

ethyl sulfate Ethyl sulfate (IUPAC name: ethyl hydrogen sulfate), also known as sulfovinic acid, is an organic chemical compound used as an intermediate in the production of ethanol from ethylene. It is the ethyl ester of sulfuric acid. History This substanc ...

and

potassium cyanide Potassium cyanide is a compound with the formula KCN. It is a colorless salt, similar in appearance to sugar, that is highly soluble in water. Most KCN is used in gold mining, organic synthesis, and electroplating. Smaller applications include ...

Applications

Propionitrile is a solvent similar to

acetonitrile Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not class ...

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 Flopropione (Compacsul, Cospanon, Ecapron, Pellegal, Argobyl, Floveton, Saritron, Spamorin, Labrodax, Tryalon, Mirulevatin, Padeskin, Profenon) is a spasmolytic or antispasmodic agent. It acts as a COMT inhibitor. It is synthesized from phloro ...

by the Houben-Hoesch reaction. The nitrile aldol reaction with

benzophenone Benzophenone is a naturally occurring organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. Benzophenone has been found in some fungi, fruits and plants, including grapes. It is a white solid with a low melting point and ros ...

, followed by reduction of the nitrile with lithium aluminium hydride gives

2-MDP 2-MDP (U-23807A) is a dissociative anaesthetic drug which has been found to be an NMDA antagonist and produces similar effects to PCP in animals. The ''levo'' or (−)-isomer is the active form of the drug. It also has stimulant effects, having ...

. This agent possesses

appetite suppressant An anorectic is a drug that reduces appetite, resulting in lower food consumption, leading to weight loss. These substances work by affecting the central nervous system or certain neurotransmitters to create a feeling of fullness or reduce the desi ...

and antidepressant properties. : 2-MDP

Safety

The toxicity of propionitrile is listed as 39 mg/kg
PubChem: Propionitrile NIOSH Toxicity Data
'. Retrieved 6 Jan 2022. and as 230 my (both rats, oral). In 1979, the Kalama (Vega) plant in Beaufort,

South Carolina South Carolina ( ) is a U.S. state, state in the Southeastern United States, Southeastern region of the United States. It borders North Carolina to the north and northeast, the Atlantic Ocean to the southeast, and Georgia (U.S. state), Georg ...

experienced an explosion during the production of propionitrile by nickel-catalyzed hydrogenation of acrylonitrile.First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina

United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent agency of the United States government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it began operation on De ...

This site is now one of the two

Superfund Superfund is a United States federal environmental remediation program established by the Comprehensive Environmental Response, Compensation, and Liability Act of 1980 (CERCLA). The program is administered by the United States Environmental Pro ...

cleanup sites in South Carolina.

References

External links

NIST Chemistry WebBook for C3H5N

{{Authority control 3 Solvents