|Jmol-3D images||Image 1
|Molar mass||53.06 g mol−1|
|Melting point||−84 °C (−119 °F; 189 K)|
|Boiling point||77 °C (171 °F; 350 K)|
|Solubility in water||7 g/100mL|
|Related compounds||acrylic acid,
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Acrylonitrile is a chemical compound with the formula C
3N. 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.
Most industrial acrylonitrile is produced by catalytic ammoxidation of propylene, also known as the Sohio process. In 2002, world production capacity was estimated at 5 million tonnes per annum. Acetonitrile and hydrogen cyanide are significant byproducts that are recovered for sale. In fact, the 2008-2009 acetonitrile shortage was caused by a decrease in demand for acrylonitrile.
In the Sohio process, propylene, ammonia, and air (oxidizer) are passed through a fluidized bed reactor containing the catalyst at 400–510 °C and 50–200 kPag. The reactants pass through the reactor only once, before being quenched in aqueous sulfuric acid. Excess propylene, carbon monoxide, carbon dioxide, and dinitrogen that do not dissolve are vented directly to the atmosphere, or are incinerated. The aqueous solution consists of acrylonitrile, acetonitrile, hydrocyanic acid, and ammonium sulfate (from excess ammonia). A recovery column removes bulk water, and acrylonitrile and acetonitrile are separated by distillation. Historically, one of the first successful catalysts was bismuth phosphomolybdate supported on silica as a heterogeneous catalyst. Further improvements have since been made.
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 highly flammable and toxic. It undergoes explosive polymerization. The burning material releases fumes of hydrogen cyanide and oxides of nitrogen. It is classified as a Class 2B carcinogen (possibly carcinogenic) by the International Agency for Research on Cancer (IARC), and workers exposed to high levels of airborne acrylonitrile are diagnosed more frequently with lung cancer than the rest of the population.
Acrylonitrile increases cancer in high dose tests in male and female rats and mice.
Pathways of exposure for humans 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 to a certain extent dermal uptake (tested with volunteer humans and in rat studies).
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.
- James F. Brazdil (2005), "Acrylonitrile", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_177.pub3
- "The Sohio Acrylonitrile Process". American Chemical Society National Historic Chemical Landmarks. Retrieved 2013-05-13.
- A. Tullo. "A Solvent Dries Up". Chemical & Engineering News 86: 27. doi:10.1021/cen-v086n047.p027.
- IARC evaluation of Acrylonitrile
- EPA:OPPT Chemical Fact Sheets
- Animal Test Result on Acrylonitrile in the Carcinogenic Potency Database
- Acrylonitrile Fact Sheet: Support Document (CAS No. 107-13-1)
- Sun X (Jan 2014). "Cytotoxic effects of acrylonitrile on human umbilical cord mesenchymal stem cells in vitro.". J Mol Med Rep 9 (1): 97–102. doi:10.3892/mmr.2013.1802. PMID 24248151.
- National Pollutant Inventory - Acrylonitrile
- Comparing Possible Cancer Hazards from Human Exposures to Rodent Carcinogens
- Acrylonitrile – Integrated Risk Information System, U.S. Environmental Protection Agency
- CDC - NIOSH Pocket Guide to Chemical Hazards - Acrylonitrile
- OSHA Table Z-1 for Air Contaminants