Acrylonitrile
IUPAC name	Acrylonitrile
Systematic name	2-propenenitrile
Other names	cyanoethene, vinylcyanide
Identifiers
CAS number	[107-13-1]
SMILES	C=CC#N
Properties
Molecular formula	C3H3N
Molar mass	53.1 g/mol
Appearance	Colourless liquid
Density	0.81 g/cm3
Melting point	-84 °C(189 K) IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... Chemical structure of the vinyl functional group. ... This article is about the chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ... For other uses, see Celsius (disambiguation). ... For other uses, see Kelvin (disambiguation). ...
Boiling point	77 °C (350 K) Italic text This article is about the boiling point of liquids. ... For other uses, see Celsius (disambiguation). ... For other uses, see Kelvin (disambiguation). ...
Solubility in water	7 g/100 mL at 20 °C
Hazards
Main hazards	flammable, reactive, toxic
Related compounds
Related compounds	acrylic acid, acrolein
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Acrylonitrile is the chemical compound with the formula CH₂CHCN. 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. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... BIC pen cap, about 1 gram. ... The millilitre (ml or mL, also spelt milliliter) is a metric unit of volume that is equal to one thousandth of a litre. ... For other uses, see Celsius (disambiguation). ... The examples and perspective in this article or section may not represent a worldwide view. ... Flammable or Flammability refers to the ease at which a substance will ignite, causing fire or combustion. ... Acrylic acid or prop-2-enoic acid is a chemical compound with the formula C3H4O2 and structure (which is sometimes abbreviated as CH2=CHCOOH). ... In organic chemistry, acrolein or propenal is the simplest unsaturated aldehyde. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Look up chemical compound in Wiktionary, the free dictionary. ... A monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer [1]. // Examples of monomers are hydrocarbons such as the alkene and arene homologous series. ... For other uses, see Plastic (disambiguation). ... Chemical structure of the vinyl functional group. ... A nitrile is any organic compound which has a -C≡N functional group. ...

Uses

Acrylonitrile is used principally as a monomer in the manufacture of synthetic polymers, especially polyacrylonitrile which comprises acrylic fibers. Acrylic fibers are, among other uses, precursor for well-known carbon-fiber. It is also a component of synthetic rubber. Dimerization of acrylonitrile affords adiponitrile, used in the synthesis of certain Nylons. 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. A monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer [1]. // Examples of monomers are hydrocarbons such as the alkene and arene homologous series. ... A polymer (from Greek: πολυ, polu, many; and μέρος, meros, part) is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ... Polyacrylonitrile (PAN) is a resinous, fibrous, or rubbery organic polymer. ... Acrylic fibers are synthetic fibers made from a polymer (Polyacrylonitrile) with an average molecular weight of ~100,000. ... A cloth of woven carbon filaments Carbon fibre or carbon fiber (See spelling differences) can refer to carbon filament thread, or to felt or woven cloth made from those carbon filaments. ... This does not cite any references or sources. ... For other uses of this word, see nylon (disambiguation). ... Fumigation is a method of pest control that completely fills an area with gaseous pesticides to suffocate or poison the pests within. ... A dienophile can only properly be explained by being familar with a Diels-Alder reaction. ... The Diels-Alder reaction The Diels-Alder reaction is an organic chemical reaction (specifically, a cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. ... R-phrases , , , , , , , S-phrases , Flash point 138 °C Autoignition temperature 424 °C Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references The chemical compound acrylamide (acrylic amide) has the chemical formula C3H5NO. Its IUPAC name is 2... Acrylic acid or prop-2-enoic acid is a chemical compound with the formula C3H4O2 and structure (which is sometimes abbreviated as CH2=CHCOOH). ...

Production

Acrylonitrile is probably the nitrile manufactured on the largest scale. Most industrial acrylonitrile is produced through the Sohio process, the catalytic ammoxidation of propylene: Standard Oil of Ohio or Sohio was an American oil company that was acquired by British Petroleum, now part of BP. It was one of the successor companies to Standard Oil after the antitrust breakup in 1911. ... It has been suggested that this article or section be merged into Catalysis. ... Propylene, also known by its IUPAC name propene, is an organic compound having the chemical formula C3H6. ...

2CH₃-CH=CH₂ + 2NH₃ + 3O₂ → 2CH₂=CH-C≡N + 6H₂O

World annual production in 2001 was 4 million tonnes and in 2005 6 million tonnes, with just under half of that coming from the United States. In 1996 the Sohio acrylonitrile process was designated an ACS National Historical Chemical Landmark in recognition of the innovative single-step method of production that made acrylonitrile available for chemical manufacturing worldwide.[1] For other uses, see Ammonia (disambiguation). ... This article is about the chemical element and its most stable form, or dioxygen. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... This article is about the year. ... This article is about the metric tonne. ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... Year 1996 (MCMXCVI) was a leap year starting on Monday (link will display full 1996 Gregorian calendar). ... The ACS National Historic Chemical Landmarks Program was launched by the American Chemical Society in 1992 and has recognized over 50 landmarks to date. ...

Safety

Acrylonitrile is highly flammable and toxic. It undergoes explosive polymerization. The burning material releases fumes of hydrogen cyanide and oxides of nitrogen. Acrylonitrile is classified as a recognized human carcinogen^[1] This article is concerned solely with chemical explosives. ... An example of alkene polymerisation, in which each Styrene monomer units double bond reforms as a single bond with another styrene monomer and forms polystyrene. ... R-phrases , , , , . S-phrases , , , , , , , , . Flash point −17. ... [1] R-phrases , S-phrases , , , , , Supplementary data page Structure and properties n, εr, etc. ...

References

1. ^ Recognized Carcinogens

External links

• National Pollutant Inventory - Acrylonitrile