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| acrylonitrile | |
|---|---|
| Name | Acrylonitrile |
| IUPACName | Prop-2-enenitrile |
| CASNumber | 107-13-1 |
| Formula | C3H3N |
| MolarMass | 53.06 g·mol−1 |
| Density | 0.806 g·cm−3 |
| BoilingPoint | 77 °C |
| MeltingPoint | −83 °C |
| Appearance | Colorless liquid |
acrylonitrile A volatile organic compound widely used as a precursor in industrial chemistry, acrylonitrile is a colorless liquid with a pungent odor. It serves as a monomer for important synthetic materials and features prominently in petrochemical manufacturing, global supply chains, and occupational health discussions.
Acrylonitrile appears in chemical manufacturing with connections to major companies and locations such as ExxonMobil, BASF, Dow Chemical Company, Sinopec, and Texas City, Texas. Its role intersects with industrial hubs like Gulf Coast of the United States, Shanghai, Antwerp, Rotterdam, and Singapore. Debates about emissions and regulation have involved institutions including the Environmental Protection Agency and agencies in the European Union and Japan. Historical incidents and policy responses have drawn attention from international media outlets such as the New York Times, The Guardian, and BBC News.
Commercial production predominantly uses propylene oxidative ammoxidation, linking feedstocks from refineries and petrochemical complexes operated by Chevron, Shell plc, Saudi Aramco, and PetroChina. Alternative routes investigated by researchers at MIT, Stanford University, Caltech, ETH Zurich, and Max Planck Society include propane ammoxidation and catalytic dehydrogenation studied with catalysts associated with groups at Oak Ridge National Laboratory, Argonne National Laboratory, and Lawrence Berkeley National Laboratory. Processes are integrated with steam crackers and polyethylene production chains common to plants in Baytown, Texas, Ulsan, and Jebel Ali. Commodity trading venues such as the New York Stock Exchange and Singapore Exchange factor into procurement and pricing strategies.
Acrylonitrile is an unsaturated nitrile with a vinyl group conjugated to a cyano functional group; its chemical behavior relates to polymerization, nucleophilic addition, and radical reactions studied by chemists at Harvard University, University of Cambridge, University of Oxford, Columbia University, and University of Tokyo. It undergoes free-radical polymerization initiated by peroxides and azo compounds similar to reagents discussed in texts from the Royal Society of Chemistry and American Chemical Society. Catalytic hydrogenation, hydrocyanation, and epoxidation pathways have been explored in literature from ACS Publications, Nature, and Science. Its susceptibility to oxidation and formation of peroxides informs storage and inhibitor strategies referenced in standards from ASTM International and International Organization for Standardization.
Acrylonitrile is the monomer for polyacrylonitrile (PAN) fibers and copolymers used to make synthetic fibers and plastics in industries served by manufacturers such as DuPont, Toray Industries, Asahi Kasei, Mitsubishi Chemical, and Kolon Industries. PAN is the precursor for carbon fiber feedstock utilized by aerospace and automotive companies like Boeing, Airbus, General Motors, Tesla, Inc., and Honda. Copolymers form ABS plastics used by electronics firms such as Samsung Electronics, Apple Inc., Sony, and LG Corporation. Its derivatives are raw materials for acrylamides, adiponitrile, and nitrile rubber relevant to producers including Sumitomo Chemical and Continental AG.
Exposure concerns have engaged public health organizations including the World Health Organization, Centers for Disease Control and Prevention, Occupational Safety and Health Administration, and the Agency for Toxic Substances and Disease Registry. Epidemiological and toxicological research from institutions like Johns Hopkins University, Karolinska Institute, Imperial College London, University of Toronto, and National Institutes of Health examines links to respiratory, neurological, and carcinogenic outcomes. Environmental monitoring programs at ports in Los Angeles, Houston, Rotterdam, and Hamburg assess air and water concentrations, while case studies of industrial releases have prompted investigations by entities such as National Transportation Safety Board and national legislatures including the United States Congress and European Parliament.
Regulatory frameworks set exposure limits and handling rules via agencies and standards organizations including the Occupational Safety and Health Administration, National Institute for Occupational Safety and Health, European Chemicals Agency, United Nations Environment Programme, and International Labour Organization. Industrial safety management borrows from practices codified by National Fire Protection Association, International Maritime Organization, International Civil Aviation Organization, and guidance from insurers and certification bodies like Lloyd's Register and Det Norske Veritas. Emergency response protocols align with training provided by Federal Emergency Management Agency and regional fire services in urban centers such as New York City, London, and Tokyo.
The development of acrylonitrile chemistry traces to early 20th-century organic chemistry research at institutions including Kaiser Wilhelm Society, University of Göttingen, Sorbonne University, and industrial labs at IG Farben and later companies like Monsanto and Bayer. Nomenclature and standardization were influenced by bodies such as the International Union of Pure and Applied Chemistry, American Chemical Society, and historical patent literature filed with patent offices like the United States Patent and Trademark Office and the European Patent Office. The compound's commercialization and integration into global supply chains reflect industrial histories tied to regions reshaped by events such as World War II and postwar reconstruction efforts overseen by organizations like the Marshall Plan administration.
Category:Organonitrogen compounds