Acrylonitrile 99% 100mL, monomer with polymerization inhibitor
Acrylonitrile 99% 100mL is an organic compound with the formula CH2CHCN. It is a colorless volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses. Acrylonitrile was first synthesized by the French chemist Charles Moureu (1863–1929) in 1893.
Chemical Formula: C3H3N
Molecular weght: 53.064 g·mol−1
Density: 0.81 g/cm3
Boiling point: 77 °C
Melting point: −84 °C
Appearance: colourless liquid
Acrylonitrile 99% 100mL 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). Hydrodimerization of acrylonitrile affords adiponitrile, used in the synthesis of certain nylons:
- 2 CH2=CHCN + 2 e− + 2 H+ → NCCH2CH2CH2CH2CN
Small amounts are also used as a fumigant. Acrylonitrile and derivatives, such as 2-chloroacrylonitrile, 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 at low doses. 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 is one of seven toxicants in cigarette smoke that are most associated with respiratory tract carcinogenesis. The mechanism of action of acrylonitrile appears to involve oxidative stress and oxidative DNA damage. Acrylonitrile increases cancer in high dose tests in male and female rats and mice and induces apoptosis in human umbilical cord mesenchymal stem cells.
It evaporates quickly at room temperature (20 °C) to reach dangerous concentrations; skin irritation, respiratory irritation, and eye irritation are the immediate effects of this exposure. 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). Repeated exposure causes skin sensitization and may cause central nervous system and liver damage.
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 enzymatically converted into 2-cyanoethylene oxide which will produce cyanide end products that ultimately form thiocyanate, which is excreted via urine. Exposure can thus be detected via blood draws and urine sampling.