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 + 2NH3 + 3O2 → 2CH2=CH-C≡N + 6H2O

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 formsthiocyanate, which is excreted via urine, or carbon dioxide and eliminated through the lungs. [1]



Acrylonitrile
external image 120px-Acrylonitrile-2D.png
external image 120px-Acrylonitrile-2D-skeletal.svg.png
external image 120px-Acrylonitrile-3D-balls.png
external image 120px-Acrylonitrile-3D-vdW.png
IUPAC name[hide]2-propenenitrile
Other names[hide]cyanoethene,

vinylcyanide
Identifiers
CAS number
107-13-1
Yes
Yes

PubChem
7855
ChemSpider
7567
Yes
Yes

UNII
MP1U0D42PE
Yes
Yes

KEGG
C01998
Yes
Yes

ChEBI
CHEBI:28217
Yes
Yes

ChEMBL
CHEMBL445612
Yes
Yes

Jmol-3D images
Image 1
Image 2
SMILES
[show]
InChI
[show]
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,
reactive,
toxic
NFPA 704
NFPA 704.svg
NFPA 704.svg

342
Related compounds
Related compounds
acrylic acid,
acrolein
Yes
Yes
(verify) (what is:
Yes
Yes
/external image 10px-X_mark.svg.png?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

"Acrylonitrile." Wikipedia. Wikimedia Foundation, 05 June 2012. Web. 09 May 2012. <http://en.wikipedia.org/wiki/Acrylonitrile>.