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| acetonitrile | |
|---|---|
| Name | Acetonitrile |
| Other names | Methyl cyanide, Ethanenitrile |
| IUPAC name | Ethanitrile |
| Formula | CH3CN |
| Molar mass | 41.05 g·mol−1 |
| Density | 0.786 g·cm−3 |
| Melting point | −45.7 °C |
| Boiling point | 81.6 °C |
| Solubility | Miscible with many organic solvents |
acetonitrile is a low-boiling, polar aprotic organic solvent widely used in laboratory and industrial chemistry. It appears as a colorless liquid with a characteristic sweet, ether-like odor and is notable for its role in chromatography, organic synthesis, and battery electrolytes. Major chemical producers and research laboratories employ acetonitrile for tasks that require a relatively inert, nitrile-containing solvent.
Acetonitrile is the simplest aliphatic nitrile, consisting of a methyl group bonded to a cyano functional group; its molecular geometry and vibrational spectra have been characterized in studies affiliated with Royal Society of Chemistry, Max Planck Society, and Brookhaven National Laboratory. Crystallographic and spectroscopic work reported by teams at Harvard University, Massachusetts Institute of Technology, and University of Oxford detail bond lengths and dipole moment consistent with a linear C≡N moiety and a tetrahedral methyl carbon. Physical properties such as boiling point, refractive index, and dielectric constant are tabulated by U.S. National Institute of Standards and Technology, International Union of Pure and Applied Chemistry, and Royal Society of Chemistry. Thermodynamic datasets compiled by National Institutes of Health groups and the European Chemicals Agency assist process engineers at firms like BASF, Dow Chemical Company, and Evonik Industries in selecting acetonitrile for solvent applications.
Industrial production historically relied on ammoxidation of propylene, a process developed and optimized by researchers associated with Haldor Topsoe, Union Carbide, and Shell plc. Large-scale plants operated by BASF, Sasol, and INEOS use continuous catalytic reactors modeled on pilot studies from California Institute of Technology and ETH Zurich. Alternate laboratory syntheses are documented in protocols from American Chemical Society publications and techniques taught at California Institute of Technology and University of California, Berkeley—including dehydration of acetamide (a method traced to classic work at University of Cambridge) and oxidative dehydrogenation routes explored by groups at Tokyo Institute of Technology. Supply-chain disruptions noted by World Trade Organization reports and raw material price changes studied by International Energy Agency have influenced production capacity and global trade.
Acetonitrile is not a major natural product but can be detected at trace levels in certain interstellar media studied by researchers at NASA, European Space Agency, and Max Planck Institute for Astronomy. Its principal uses include high-performance liquid chromatography (HPLC) mobile phases (techniques standardized by United States Pharmacopeia and European Pharmacopoeia), extraction media in pharmaceutical manufacturing at companies such as Pfizer, Novartis, and Roche, and as a solvent in electrochemical cells developed by teams at Toyota Motor Corporation and Tesla, Inc.. Analytical laboratories at Centers for Disease Control and Prevention and Food and Drug Administration rely on acetonitrile for mass spectrometry sample preparation, following method guidance from International Council for Harmonisation. In materials science, acetonitrile serves as a component in lithium-ion battery electrolytes studied by Argonne National Laboratory and Pacific Northwest National Laboratory.
As a nitrile, acetonitrile undergoes nucleophilic addition and serves as a mild ligand in coordination chemistry; coordination complexes involving acetonitrile have been synthesized at University of California, Los Angeles, Columbia University, and University of Chicago. It participates in metal-catalyzed cross-coupling reactions developed by laureates associated with Nobel Prize in Chemistry research, and it can be deprotonated at the methyl group under strong bases following protocols from Royal Society of Chemistry and American Chemical Society journals. Acetonitrile is used as a solvent in Grignard and organolithium reactions taught in courses at Yale University and Princeton University; its relative inertness toward many electrophiles makes it a common choice in organic and inorganic synthesis documented in textbooks from Oxford University Press.
Toxicological evaluations by U.S. Environmental Protection Agency, European Chemicals Agency, and World Health Organization indicate that acetonitrile exposure can affect the central nervous system and, upon metabolism, release cyanide; occupational exposure limits are set by Occupational Safety and Health Administration and National Institute for Occupational Safety and Health. Material safety data sheets distributed by Sigma-Aldrich and Fisher Scientific recommend engineering controls, personal protective equipment, and safe storage consistent with guidance from American Chemical Society and Health and Safety Executive. Emergency response protocols often reference training materials from Red Cross and National Fire Protection Association for spills, fires, and medical treatment.
Environmental monitoring programs run by Environmental Protection Agency and European Environment Agency assess acetonitrile in wastewater and ambient air, with biodegradation studies reported by United States Geological Survey and Agence Française de Sécurité Sanitaire de l’Alimentation, de l’Environnement et du Travail. Regulatory frameworks for handling, transport, and disposal are enforced under statutes and directives from United States Department of Transportation, International Maritime Organization, and European Chemicals Agency REACH legislation, and compliance is audited by organizations like Bureau Veritas and Lloyd's Register. Remediation of contaminated sites has been addressed in applied research at Sandia National Laboratories and Lawrence Berkeley National Laboratory using biodegradation and advanced oxidation methods.
Category:Nitriles