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Acrylonitrile is a chemical compound with the formula C3H3N. This colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. 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.
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.
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 |
Production
Most industrial acrylonitrile is produced by catalytic ammoxidation of propene: