Acrylonitrile 309333 207969867 2008-04-24T22:02:26Z 128.115.27.10 /* Uses */ {{chembox new | ImageFileL1 = Acrylonitrile-2D.png | ImageSizeL1 = 120 px | ImageFileR1 = Acrylonitrile-2D-skeletal.png | ImageSizeR1 = 120 px | ImageFileL2 = Acrylonitrile-3D-balls.png | ImageSizeL2 = 120 px | ImageFileR2 = Acrylonitrile-3D-vdW.png | ImageSizeR2 = 120 px | IUPACName = Acrylonitrile | SystematicName = 2-propenenitrile | OtherNames = cyanoethene,<br/>[[vinyl]][[cyanide]] | Section1 = {{Chembox Identifiers | Abbreviations = | CASNo = 107-13-1 | EINECS = | EINECSCASNO = | PubChem = | SMILES = C=CC#N | InChI = | RTECS = | MeSHName = | ChEBI = | KEGG = | ATCCode_prefix = | ATCCode_suffix = | ATC_Supplemental =}} | Section2 = {{Chembox Properties | Formula = C<sub>3</sub>H<sub>3</sub>N | MolarMass = 53.1 g/mol | Appearance = Colourless liquid | Density = 0.81 g/cm3 | MeltingPt = -84 [[celsius|°C]](189 [[kelvin|K]]) | Melting_notes = | BoilingPt = 77 [[celsius|°C]] (350 [[kelvin|K]]) | Boiling_notes = | Solubility = 7 [[gram|g]]/100 [[milliliter|mL]] at 20 [[celsius|°C]] | SolubleOther = | Solvent = [[ethanol]], [[diethyl ether]],<br/>[[chloroform]] | LogP = | VaporPressure = | HenryConstant = | AtmosphericOHRateConstant = | pKa = | pKb = }} | Section3 = {{Chembox Structure | CrystalStruct = | Coordination = | MolShape = }} | Section4 = {{Chembox Thermochemistry | DeltaHf = | DeltaHc = | Entropy = | HeatCapacity = }} | Section5 = {{Chembox Pharmacology | AdminRoutes = | Bioavail = | Metabolism = | HalfLife = | ProteinBound = | Excretion = | Legal_status = | Legal_US = | Legal_UK = | Legal_AU = | Legal_CA = | PregCat = | PregCat_AU = | PregCat_US = }} | Section6 = {{Chembox Explosive | ShockSens = | FrictionSens = | ExplosiveV = | REFactor = }} | Section7 = {{Chembox Hazards | EUClass = | EUIndex = | MainHazards = [[flammable]],<br/>reactive,<br/> toxic | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-O = | RPhrases = | SPhrases = | RSPhrases = | FlashPt = | Autoignition = | ExploLimits = | PEL = }} | Section8 = {{Chembox Related | OtherAnions = | OtherCations = | OtherFunctn = | Function = | OtherCpds = [[acrylic acid]],<br/>[[acrolein]]}} }} '''Acrylonitrile''' is the [[chemical compound]] with the formula CH<sub>2</sub>CHCN. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important [[monomer]] for the manufacture of useful [[plastic]]s. In-terms-of its molecular structure, it consists of a [[vinyl]] group linked to a [[nitrile]]. ==Uses== Acrylonitrile is used principally as a [[monomer]] in the manufacture of synthetic [[polymer]]s, especially [[polyacrylonitrile]] which comprises [[acrylic fiber]]s. Acrylic fibers are, among other uses, [[wiktionary:Precursor|precursor]] for well-known [[carbon-fiber]]. It is also a component of [[rubber|synthetic rubber]]. Dimerization of acrylonitrile affords adiponitrile, used in the synthesis of certain [[Nylon]]s. Small amounts are also used as a [[fumigant]]. Acrylonitrile and derivatives such as '''2-chloro-acrylonitrile''' are [[dienophile]]s in [[Diels-Alder reaction]]s. Acrylonitrile is also a precursor in the industrial manufacture of [[acrylamide]] and [[acrylic acid]]. ==Production== Acrylonitrile is probably the nitrile manufactured on the largest scale. Most industrial acrylonitrile is produced through the [[Sohio]] process, the [[catalyst|catalytic]] ammoxidation of [[propylene]]: :2CH<sub>3</sub>-CH=CH<sub>2</sub> + 2[[ammonia|NH<sub>3</sub>]] + 3[[oxygen|O<sub>2</sub>]] → 2CH<sub>2</sub>=CH-C≡N + 6[[water|H<sub>2</sub>O]] World annual production in [[2001]] was 4 million [[tonne]]s and in [[2005]] 6 million tonnes, with just under half of that coming from the [[United States]]. In [[1996]] the Sohio acrylonitrile process was designated an [[ACS National Historical Chemical Landmarks|ACS National Historical Chemical Landmark]] in recognition of the innovative single-step method of production that made acrylonitrile available for chemical manufacturing worldwide.[http://acswebcontent.acs.org/landmarks/landmarks/soh/index.html] ==Safety== Acrylonitrile is highly flammable and toxic. It undergoes [[explosive]] [[polymerization]]. The burning material releases fumes of [[hydrogen cyanide]] and [[nitrogen dioxide|oxides of nitrogen]]. Acrylonitrile is classified as a recognized human carcinogen<ref>[http://www.scorecard.org/health-effects/chemicals.tcl?short_hazard_name=cancer&all_p=t Recognized Carcinogens<!-- Bot generated title -->]</ref> == References == <references/> ==External links== * [http://www.npi.gov.au/database/substance-info/profiles/7.html National Pollutant Inventory - Acrylonitrile] [[Category:Nitriles]] [[Category:Monomers]] [[Category:Fumigants]] [[Category:Hazardous air pollutants]] [[de:Acrylnitril]] [[es:Acrilonitrilo]] [[fr:Acrylonitrile]] [[it:Acrilonitrile]] [[nl:Acrylonitril]] [[ja:アクリロニトリル]] [[pl:Akrylonitryl]] [[pt:Acrilonitrila]] [[ru:Акрилонитрил]] [[fi:Akryylinitriili]] [[uk:Акрилонітрил]] [[zh:丙烯腈]]