acrylonitrile

= Acrylonitrile = **Acrylonitrile** is the [|chemical compound] with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important [|monomer] for the manufacture of useful [|plastics]. In terms of its molecular structure, it consists of a [|vinyl] group linked to a [|nitrile]. Pathways of exposure include emissions, auto exhaust, and cigarette smoke that can expose the human subject directly if they inhale or smoke. Routes of exposure include inhalation, oral, and occasional dermal routes from volunteer humans and rat studies. [|[1]]
 * Acrylonitrile** is the [|chemical compound] with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important [|monomer] for the manufacture of useful [|plastics] . In terms of its molecular structure, it consists of a [|vinyl] group linked to a [|nitrile] . Pathways of exposure include emissions, auto exhaust, and cigarette smoke that can expose the human subject directly if they inhale or smoke. Routes of exposure include inhalation, oral, and occasional dermal routes from volunteer humans and rat studies. [|[1]]
 * Acrylonitrile** is the [|chemical compound] with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important [|monomer] for the manufacture of useful [|plastics] . In terms of its molecular structure, it consists of a [|vinyl] group linked to a [|nitrile] . Pathways of exposure include emissions, auto exhaust, and cigarette smoke that can expose the human subject directly if they inhale or smoke. Routes of exposure include inhalation, oral, and occasional dermal routes from volunteer humans and rat studies. [|[1]]

Uses
Acrylonitrile is used principally as a [|monomer] to prepare [|polyacrylonitrile], a [|homopolymer] , or several important [|copolymers] such as [|styrene-acrylonitrile] (SAN), [|acrylonitrile butadiene styrene] (ABS), acrylonitrile styrene acrylate (ASA) and other [|synthetic rubbers] such as [|acrylonitrile butadiene] (NBR). Dimerization of acrylonitrile affords [|adiponitrile], used in the synthesis of certain [|polyamides]. Small amounts are also used as a [|fumigant]. Acrylonitrile and derivatives such as 2-chloro-acrylonitrile are [|dienophiles] in [|Diels-Alder reactions]. Acrylonitrile is also a precursor in the industrial manufacture of [|acrylamide] and [|acrylic acid]. Acrylonitrile is also the most commonly used eluent in liquid chromatography.

Production
Of all the nitriles, Acrylonitrile is probably manufactured on the largest scale. Most industrial acrylonitrile is produced by [|catalytic] [|ammoxidation] of [|propene] : 2CH3-CH=CH2 + 2 [|NH3] + 3 [|O2] → 2CH2=CH-C≡N + 6 [|H2O]

Health effects
Acrylonitrile is highly flammable and toxic. It undergoes [|explosive] [|polymerization]. The burning material releases fumes of [|hydrogen cyanide] and [|oxides of nitrogen]. The International Agency for Research on Cancer (IARC) concluded that there is inadequate evidence in humans for the carcinogenicity of acrylonitrile, but classified it as a [|Class 2B carcinogen] (possibly carcinogenic). [|[2]] Acrylonitrile increases cancer in high dose tests in male and female rats and mice. [|[3]] There are two main excretion processes of acrylonitrile. The primary method is excretion in urine when acrylonitrile is metabolized by being directly conjugated to [|glutathione]. The other method is when acrylonitrile is metabolized with [|2-cyanoethylene oxide] to produce [|cyanide] end products that ultimately forms [|thiocyanate], which is excreted via urine, or [|carbon dioxide] and eliminated through the lungs. [|[1]]


 * ~ Acrylonitrile ||
 * [[image:http://upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Acrylonitrile-2D.png/120px-Acrylonitrile-2D.png width="120" height="95" link="http://en.wikipedia.org/wiki/File:Acrylonitrile-2D.png"]] || [[image:http://upload.wikimedia.org/wikipedia/commons/thumb/0/02/Acrylonitrile-2D-skeletal.svg/120px-Acrylonitrile-2D-skeletal.svg.png width="120" height="60" link="http://en.wikipedia.org/wiki/File:Acrylonitrile-2D-skeletal.svg"]] ||
 * [[image:http://upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Acrylonitrile-3D-balls.png/120px-Acrylonitrile-3D-balls.png width="120" height="85" link="http://en.wikipedia.org/wiki/File:Acrylonitrile-3D-balls.png"]] || [[image:http://upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Acrylonitrile-3D-vdW.png/120px-Acrylonitrile-3D-vdW.png width="120" height="85" link="http://en.wikipedia.org/wiki/File:Acrylonitrile-3D-vdW.png"]] ||
 * [|IUPAC name] [|[hide]] 2-propenenitrile  ||
 * Other names [|[hide]] cyanoethene,

 [|vinyl][|cyanide] || [|Image 2] ||  [|[show]] ||  [|[show]] || reactive, toxic ||  342 || [|acrolein] || Except where noted otherwise, data are given for materials in their [|standard state (at 25 °C, 100 kPa)] || "Acrylonitrile." //Wikipedia//. Wikimedia Foundation, 05 June 2012. Web. 09 May 2012. .
 * ~ Identifiers ||
 * [|CAS number] || [|107-13-1]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|PubChem] || [|7855]  ||
 * [|ChemSpider] || [|7567]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|UNII] || [|MP1U0D42PE]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|KEGG] || [|C01998]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|ChEBI] || [|CHEBI:28217]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|ChEMBL] || [|CHEMBL445612]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|Jmol] -3D images || [|Image 1]
 * [|SMILES]
 * [|InChI]
 * ~ Properties ||
 * [|Molecular formula] || C3H3N ||
 * [|Molar mass] || 53.06 g mol−1 ||
 * Appearance || Colourless liquid ||
 * [|Density] || 0.81 g/cm3 ||
 * [|Melting point] || -84 °C(189 [|K] ) ||
 * [|Boiling point] || 77 °C (350 [|K] ) ||
 * [|Solubility] in [|water] || 7 g/100 [|mL] at 20 °C ||
 * ~ Hazards ||
 * [|MSDS] || [|ICSC 0092] ||
 * Main [|hazards] || [|flammable] ,
 * [|NFPA 704] || [[image:http://upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/75px-NFPA_704.svg.png width="75" height="75" caption="NFPA 704.svg" link="http://en.wikipedia.org/wiki/File:NFPA_704.svg"]]
 * ~ Related compounds ||
 * Related compounds || [|acrylic acid] ,
 * = [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png width="14" height="14" caption="Yes"]] [|(verify)]  [|(what is:] [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/10px-Yes_check.svg.png width="10" height="10" caption="Yes"]]/[[image:http://upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/10px-X_mark.svg.png width="10" height="11"]]?)
 * = [|Infobox references] ||