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

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

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 prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including me ...

. 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 although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecula ...

. It is also prepared by the ammoxidation of propanol (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. :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 In physiology, dehydration is a lack of total body water, with an accompanying disruption of metabolic processes. It occurs when free water loss exceeds free water intake, usually due to exercise, disease, or high environmental temperature. Mil ...

of propionamide, by catalytic reduction of

, or by distilling ethyl sulfate and

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

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 clas ...

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 Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is a widely used building block in organic chemistry, being the parent diarylket ...

, 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 o ...

. This agent possesses

appetite suppressant An anorectic or anorexic is a drug which reduces appetite, resulting in lower food consumption, leading to weight loss. By contrast, an appetite stimulant is referred to as orexigenic. The term is (from the Greek ''ἀν-'' (an-) = "without" ...

and antidepressant properties. : U-23,807A

Safety

Propanenitrile is only weakly toxic with an of 230 mg/kg (rats, oral). Propanenitrile has been determined to be

teratogenic Teratology is the study of abnormalities of physiological development in organisms during their life span. It is a sub-discipline in medical genetics which focuses on the classification of congenital abnormalities in dysmorphology. The related ...

due to the metabolic release of cyanide. In 1979, the Kalama (Vega) plant in

Beaufort Beaufort may refer to: People and titles * Beaufort (surname) * House of Beaufort, English nobility * Duke of Beaufort (England), a title in the peerage of England * Duke of Beaufort (France), a title in the French nobility Places Polar regions * ...

South Carolina )''Animis opibusque parati'' ( for, , Latin, Prepared in mind and resources, links=no) , anthem = " Carolina";" South Carolina On My Mind" , Former = Province of South Carolina , seat = Columbia , LargestCity = Charleston , LargestMetro = ...

experienced an explosion during the production of propionitrile by nickel-catalyzed reduction 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 executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it ...

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 Environmental Protection Agency ...

cleanup sites in South Carolina.

References

External links

NIST Chemistry WebBook for C3H5N

{{Authority control 3 Solvents