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Acrylonitrile

 

 
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Acrylonitrile
 
 
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Acrylonitrile is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 with the formula CH2CHCN. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
 for the manufacture of useful plastic
Plastic

Plastic is the general common term for a wide range of synthetic or semisynthetic organic chemistry solid materials suitable for the manufacture of industrial products....
s. In terms of its molecular structure, it consists of a vinyl
Vinyl

A vinyl compound is any organic compound that contains a vinyl group , −CarbonHydrogenCovalent bondCH2. These are derivatives of ethene, CH2=CH2, with one hydrogen atom replaced with some other group....
 group linked to a nitrile
Nitrile

A nitrile is any organic compound which has a -Carbon=Nitrogen functional group. The -C=N functional group is called a nitrile group....
.

lonitrile is used principally as a monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
 in the manufacture of synthetic polymer
Polymer

A polymer is a large molecule composed of repeating structural units typically connected by covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large class of natural and synthetic materials with a variety of properties....
s, especially polyacrylonitrile
Polyacrylonitrile

Polyacrylonitrile is a resinous, fiber, or rubbery organic polymer. Almost all polyacrylonitrile resins are copolymers made from mixtures of monomers; with acrylonitrile as the main component....
 which comprises acrylic fiber
Acrylic fiber

Acrylic fibers are synthetic fibers made from a polymer with an average molecular weight of ~100,000, about 1900 monomer units. To be called acrylic in the U.S, the polymer must contain at least 85% acrylonitrile monomer....
s.






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Encyclopedia


Acrylonitrile is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 with the formula CH2CHCN. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
 for the manufacture of useful plastic
Plastic

Plastic is the general common term for a wide range of synthetic or semisynthetic organic chemistry solid materials suitable for the manufacture of industrial products....
s. In terms of its molecular structure, it consists of a vinyl
Vinyl

A vinyl compound is any organic compound that contains a vinyl group , −CarbonHydrogenCovalent bondCH2. These are derivatives of ethene, CH2=CH2, with one hydrogen atom replaced with some other group....
 group linked to a nitrile
Nitrile

A nitrile is any organic compound which has a -Carbon=Nitrogen functional group. The -C=N functional group is called a nitrile group....
.

Uses

Acrylonitrile is used principally as a monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
 in the manufacture of synthetic polymer
Polymer

A polymer is a large molecule composed of repeating structural units typically connected by covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large class of natural and synthetic materials with a variety of properties....
s, especially polyacrylonitrile
Polyacrylonitrile

Polyacrylonitrile is a resinous, fiber, or rubbery organic polymer. Almost all polyacrylonitrile resins are copolymers made from mixtures of monomers; with acrylonitrile as the main component....
 which comprises acrylic fiber
Acrylic fiber

Acrylic fibers are synthetic fibers made from a polymer with an average molecular weight of ~100,000, about 1900 monomer units. To be called acrylic in the U.S, the polymer must contain at least 85% acrylonitrile monomer....
s. Acrylic fibers are, among other uses, precursor for well-known carbon-fiber. It is also a component of synthetic rubber
Rubber

Natural rubber is an elastomer?an Elasticity_ hydrocarbon polymer?that was originally derived from a milky colloidal suspension, or latex , found in the sap of some plants....
. Dimerization of acrylonitrile affords adiponitrile, used in the synthesis of certain Nylon
Nylon

Nylon is a generic designation for a family of synthetic polymers known generically as polyamides and first produced on February 28, 1935 by Wallace Carothers at DuPont....
s. Small amounts are also used as a fumigant. Acrylonitrile and derivatives such as 2-chloro-acrylonitrile are dienophiles in Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
s. Acrylonitrile is also a precursor in the industrial manufacture of acrylamide
Acrylamide

The chemical compound acrylamide has the chemical formula Carbon3Hydrogen5NitrogenOxygen. Its IUPAC name is 2-propenamide....
 and acrylic acid
Acrylic acid

Acrylic acid or prop-2-enoic acid is a chemical compound and it is the simplest unsaturated compound carboxylic acid with a vinyl group at the alpha carbon position and a carboxylic acid terminus....
.

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
Propylene

Propene, also known as propylene, is an saturation organic chemistry having the chemical formula Carbon3Hydrogen6. It has one covalent bond, and is the second simplest member of the alkene class of hydrocarbons, and it is also second in natural abundance....
:
2CH3-CH=CH2 + 2NH3
Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
 + 3O2
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 ? 2CH2=CH-C=N + 6H2O
Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....


World annual production in 2001 was 4 million tonne
Tonne

A tonne or metric ton , also referred to as a metric tonne, is a measurement of mass equal to 1,000 kilograms, or 2204.6226 pounds....
s and in 2005 6 million tonnes, with just under half of that coming from the United States
United States

The United States of America is a Federal government constitutional republic comprising U.S. state and a federal district. The country is situated mostly in central North America, where its Contiguous United States and Washington, D.C., the Capital districts and territories, lie between the Pacific Ocean and Atlantic Oceans, Borders of the U...
. A significant byproduct is acetonitrile
Acetonitrile

Acetonitrile is the chemical compound with chemical formula CH3CN. This colourless liquid is the simplest organic nitrile and is widely used as a solvent....
; this process is the main source of acetonitrile.

In 1996 the Sohio acrylonitrile process was designated an ACS National Historical Chemical Landmark
ACS National Historical Chemical Landmarks

The National Historic Chemical Landmarks Program was launched by the American Chemical Society in 1992 and has recognized more than 60 landmarks to date....
 in recognition of the innovative single-step method of production that made acrylonitrile available for chemical manufacturing worldwide.

Health Effects

Acrylonitrile is highly flammable and toxic. It undergoes explosive polymerization
Polymerization

In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains....
. The burning material releases fumes of hydrogen cyanide
Hydrogen cyanide

Hydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, extremely poisonous, and highly volatility liquid that boiling slightly above room temperature at 26 Celsius ....
 and oxides of nitrogen
Nitrogen dioxide

Nitrogen dioxide is the chemical compound with the chemical formula NitrogenOxygen2. One of several nitrogen oxides, NO2 is an intermediate in the industrial synthesis of nitric acid, millions of tons of which are produced each year....
. The International Agency for Research on Cancer (IARC) concluded that there is inadequate evidence in humans for the carcinogenicity of acrylonitrile. Acrylonitile increases cancer in high dose tests in male and female rats and mice.

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