Acrylonitrile
309333
207969867
2008-04-24T22:02:26Z
128.115.27.10
/* Uses */
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| ImageFileL1 = Acrylonitrile-2D.png
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| IUPACName = Acrylonitrile
| SystematicName = 2-propenenitrile
| OtherNames = cyanoethene,<br/>[[vinyl]][[cyanide]]
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| CASNo = 107-13-1
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| SMILES = C=CC#N
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| 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]])
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| BoilingPt = 77 [[celsius|°C]] (350 [[kelvin|K]])
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| Solubility = 7 [[gram|g]]/100 [[milliliter|mL]] at 20 [[celsius|°C]]
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| Solvent = [[ethanol]], [[diethyl ether]],<br/>[[chloroform]]
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| MainHazards = [[flammable]],<br/>reactive,<br/> toxic
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| OtherCpds = [[acrylic acid]],<br/>[[acrolein]]}}
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'''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]]
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[[it:Acrilonitrile]]
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[[ja:アクリロニトリル]]
[[pl:Akrylonitryl]]
[[pt:Acrilonitrila]]
[[ru:Акрилонитрил]]
[[fi:Akryylinitriili]]
[[uk:Акрилонітрил]]
[[zh:丙烯腈]]