Acrylonitrile

Acrylonitrile
IUPAC name 2-propenenitrile
Other names cyanoethene, vinylcyanide
Identifiers
CAS number	107-13-1 Y
PubChem	7855
ChemSpider	7567 Y
UNII	MP1U0D42PE Y
KEGG	C01998 Y
ChEBI	CHEBI:28217 Y
ChEMBL	CHEMBL445612 Y
Jmol-3D images	Image 1 Image 2
SMILES N#CC=C C=CC#N
InChI InChI=1S/C3H3N/c1-2-3-4/h2H,1H2 Y Key: NLHHRLWOUZZQLW-UHFFFAOYSA-N Y InChI=1/C3H3N/c1-2-3-4/h2H,1H2 Key: NLHHRLWOUZZQLW-UHFFFAOYAG
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	3 4 2
Related compounds
Related compounds	acrylic acid, acrolein
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 the 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.

Production

Of all the nitriles, Acrylonitrile is manufactured on probably 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 forms thiocyanate, which is excreted via urine, or carbon dioxide and eliminated through the lungs. ^[1]

References

1. ^ ^{a b} Acrylonitrile Fact Sheet: Support Document (CAS No. 107-13-1)
2. ^ IARC evaluation of Acrylonitrile
3. ^ Animal Test Result on Acrylonitrile in the Carcinogenic Potency Database

External links

• National Pollutant Inventory - Acrylonitrile
• Comparing Possible Cancer Hazards from Human Exposures to Rodent Carcinogens
• Acrylonitrile – Integrated Risk Information System, U.S. Environmental Protection Agency