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Acrylonitrile acts as a monomer used in the production of polyacrlonitrile plastics, adhesives and synthetic rubber. It is also used for the synthesis of copolymers such as styrene-acrylonitrile, acrylonitrile butadiene styrene, acrylonitrile styrene acrylate. It is involved in the preparation of adiponitrile by dimerization, which finds application in polyamide synthesis. It acts as a precursor to acrylamide and acrylic acid. It is used as dienophile in Diels-Alder reactions. It acts as a chemical intermediate in the synthesis of antioxidants, active pharmaceutical ingredients, dyes, and surface-active agents. Further, it is utilized for the preparation of acrylic fibers, resins and nitrile rubbers. In addition to this, it serves as a fumigant for food commodities, flour milling, and bakery food processing equipment.
The Stetter reaction (conjugate addition of aryl aldehydes) catalyzed by CN-, is exemplified by the addition of pyridine-3-carboxaldehyde to acrylonitrile to give 4-oxo-4-(3-pyridyl)butyronitrile: Org. Synth. Coll., 6, 866 (1988). See also 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, L08750.
Free radical alkylation, acylation and arylation reactions also occur in the presence of t-butyl hydroperoxide and a Cu(II) catalyst: J. Chem. Soc., Chem. Commun., 1399 (1995). Several other free radical procedures have been reported involving intramolecular homolytic aromatic substitution to give carbocyclic and heterocyclic systems: Tetrahedron Lett., 36, 4307 (1995):
The reaction is also applicable to acrylate esters and vinyl ketones; with acrylonitrile and phenoxyacetic acid, tetrahydrobenzopyran-4-carbonitrile is obtained in 41% yield.
Dai, Y.; Song, Y.; Tu, X.; Jiang, Y.; Yuan, Y. Sequential shape-selective adsorption and photocatalytic transformation of acrylonitrile production wastewater. Water Res. 2015, 85, 216-225.
Pan, X.; Lamson, M.; Yan, J.; Matyjaszewski, K. Photoinduced Metal-Free Atom Transfer Radical Polymerization of Acrylonitrile. ACS Macro Lett. 2015, 4 (2), 192-196.
Hazard Statements: H225-H301-H311-H331-H315-H318-H317-H350-H335
Highly flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes skin irritation. Causes serious eye damage. May cause an allergic skin reaction. May cause cancer. May cause respiratory irritation.
Precautionary Statements: P210-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.