propionitrile

Propionitrile, also known as propanenitrile, is an organic nitrile with the chemical formula C3H5N. It features a nitrile group (-CN) attached to a propyl chain, giving the structure CH3-CH2-CN. It is a colorless liquid at room temperature and is used as an intermedIate in organic synthesis and as a solvent for various chemical processes.

Properties and occurrence: Propionitrile has a higher molecular weight than acetonitrile and displays typical nitrile chemistry, including susceptibility to hydrolysis and reduction. It is miscible with many organic solvents and has limited water miscibility. Its physical properties, such as boiling point and density, are consistent with other small nitriles, making it useful as a reactive solvent and building block in manufacturing.

Production and sources: Commercially, propionitrile is mainly produced by hydrocyanation of propene, yielding propionitrile that is then purified. It can also arise as a byproduct or intermediate in processes that involve nitrile chemistry, and it may be prepared from propionaldehyde derivatives or via cyanation routes in some industrial settings.

Uses and reactions: Propionitrile serves as a versatile intermediate in the synthesis of carboxylic acid derivatives, amines, and other nitriles. It can be hydrolyzed under acidic or basic conditions to form propionic acid, oxidized, or reduced to propylamine. It participates in standard nitrile reactions, such as Grignard additions and various condensation processes.

Safety: Propionitrile is flammable and presents health hazards upon inhalation, ingestion, or skin contact. It is toxic and can release hydrogen cyanide under certain conditions, notably strong acidic hydrolysis. Proper storage in a cool, well-ventilated area and appropriate personal protective equipment are advised.

See also: nitriles; propionic acid; hydrocyanation.