acrylonitrile
American Heritage Dictionary:
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ac·ry·lo·ni·trile
(ăk'rə-lō-nī'trəl, -trēl, -trīl) 
n.
A colorless, liquid organic compound, H2C:CHCN, used in the manufacture of acrylic rubber and fibers.
n.
A colorless, liquid organic compound, H2C:CHCN, used in the manufacture of acrylic rubber and fibers.
[ACRYL(IC RESIN) + NITRILE.]
McGraw-Hill Science & Technology Encyclopedia:
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Acrylonitrile
An explosive, poisonous, flammable liquid, boiling at 171°F (77.3°C), partly soluble in water. It may be regarded as vinyl cyanide, and its systematic name is 2-propenonitrile. Acrylonitrile is prepared by ammoxidation of propylene over various sorts of catalysts, chiefly metallic oxides.
Most of the acrylonitrile produced is consumed in the manufacture of acrylic and modacrylic fibers. Substantial quantities are used in acrylonitrile-butadiene-styrene (ABS) resins, in nitrile elastomers, and in the synthesis of adiponitrile by electrodimerization. Smaller amounts of acrylonitrile are used in cyanoethylation reactions, in the synthesis of drugs, dyestuffs, and pesticides, and as co-monomers with vinyl acetate, vinylpyridine, and similar monomers.
Acrylonitrile undergoes spontaneous polymerization, often with explosive force. It polymerizes violently in the presence of suitable alkaline substances. See also Nitrile; Polymerization.
Wikipedia on Answers.com:
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Acrylonitrile
| Acrylonitrile | |
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2-propenenitrile |
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| Identifiers | |
| CAS number | 107-13-1  |
| PubChem | 7855 |
| ChemSpider | 7567 |
| UNII | MP1U0D42PE |
| KEGG | C01998 |
| ChEBI | CHEBI:28217 |
| ChEMBL | CHEMBL445612 |
| Jmol-3D images | Image 1 Image 2 |
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| 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 |
| Hazards | |
| MSDS | ICSC 0092 |
| Main hazards | flammable, reactive, toxic |
| NFPA 704 |
 3
4
2
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| Related compounds | |
| Related compounds | acrylic acid, acrolein |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Acrylonitrile is a chemical compound with the formula C3H3N. 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. 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.[1]
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Contents
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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. Acrylonitrile is also the most commonly used eluent in liquid chromatography.
Production
Of all the nitriles, Acrylonitrile is probably manufactured on the largest scale. Most industrial acrylonitrile is produced by catalytic ammoxidation of propene:
Health effects
Acrylonitrile is highly flammable and toxic. It undergoes explosive polymerization. The burning material releases fumes of hydrogen cyanide and oxides of nitrogen. The International Agency for Research on Cancer (IARC) concluded that there is inadequate evidence in humans for the carcinogenicity of acrylonitrile, but classified it as a Class 2B carcinogen (possibly carcinogenic). [2] Acrylonitrile increases cancer in high dose tests in male and female rats and mice. [3]
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. [1]
References
- ^ a b Acrylonitrile Fact Sheet: Support Document (CAS No. 107-13-1)
- ^ IARC evaluation of Acrylonitrile
- ^ Animal Test Result on Acrylonitrile in the Carcinogenic Potency Database
External links
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The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.
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McGraw-Hill Science & Technology Encyclopedia
McGraw-Hill Encyclopedia of Science and Technology. Copyright © 2005 by The McGraw-Hill Companies, Inc. All rights reserved.
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