Acrylonitrile


Acrylonitrile
Acrylonitrile
Identifiers
CAS number 107-13-1 YesY
PubChem 7855
ChemSpider 7567 YesY
UNII MP1U0D42PE YesY
KEGG C01998 YesY
ChEBI CHEBI:28217 YesY
ChEMBL CHEMBL445612 YesY
Jmol-3D images Image 1
Image 2
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
NFPA 704.svg
3
4
2
Related compounds
Related compounds acrylic acid,
acrolein
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Acrylonitrile is the 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]

Contents

Uses

Acrylonitrile is used principally as a monomer to prepare the 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.

Production

Of all the nitriles, Acrylonitrile is manufactured on probably the largest scale. Most industrial acrylonitrile is produced by catalytic ammoxidation of propene:

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

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

  1. ^ a b Acrylonitrile Fact Sheet: Support Document (CAS No. 107-13-1)
  2. ^ IARC evaluation of Acrylonitrile
  3. ^ Animal Test Result on Acrylonitrile in the Carcinogenic Potency Database

External links


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Look at other dictionaries:

  • Acrylonitrile — Général Nom IUPAC 2 propènenitrile Synonymes cyanure de vinyle …   Wikipédia en Français

  • acrylonitrile — ● acrylonitrile nom masculin Composé CH2≅CH― C―N obtenu à partir du propylène et qui est un des principaux monomères industriels. ● acrylonitrile (synonymes) nom masculin Composé CH 2 ≅CH― C―N obtenu à partir du propylène... Synonymes : nitrile… …   Encyclopédie Universelle

  • acrylonitrile — n. 1. a colorless liquid compound ({H2C:CH.CN}); used as raw material for acrylic fibers, and as a solvent. Syn: vinyl cyanide, cyanoethylene, 2 propenenitrile [WordNet 1.5 +PJC] …   The Collaborative International Dictionary of English

  • acrylonitrile — [ak΄rə lō nī′tril] n. [< ACRYL(IC) + O + NITRILE] a colorless, liquid monomer, H2C:CHCN, boiling at 78°C, that is polymerized to form acrylic resins for acrylic fibers, synthetic rubber, and soil conditioners: a known carcinogen …   English World dictionary

  • acrylonitrile — akrilnitrilas statusas T sritis chemija formulė CH₂=CHCN atitikmenys: angl. acrylonitrile; vinyl cyanide rus. акрилонитрил; винилцианид; нитрил акриловой кислоты ryšiai: sinonimas – propennitrilas …   Chemijos terminų aiškinamasis žodynas

  • acrylonitrile — A substance used to make plastics, rubber, and textiles. Being exposed to acrylonitrile may increase the risk of developing certain cancers, such as lung, brain, or prostate cancer …   English dictionary of cancer terms

  • acrylonitrile — noun Etymology: acrylic + o + nitrile Date: 1893 a colorless volatile flammable liquid nitrile C3H3N used chiefly in organic synthesis and for polymerization …   New Collegiate Dictionary

  • acrylonitrile — /ak reuh loh nuy tril, treel, truyl/, n. Chem. a colorless, flammable, poisonous, carcinogenic liquid, C3H3N, used for the production of polymers and copolymers, as rubbers, fibers, and clear plastics for beverage containers. [1890 95; ACRYL(IC)… …   Universalium

  • acrylonitrile — noun A toxic colourless liquid organic compound, CH=CH.CN, synthesized from propylene and ammonia; used as a monomer in the production of acrylic resins and synthetic rubber …   Wiktionary

  • acrylonitrile — ac·ry·lo·ni·trile .ak rə lō nī trəl, .trēl n a colorless volatile flammable liquid nitrile C3H3N used chiefly in organic synthesis and for polymerization * * * ac·ry·lo·ni·trile (ak″rə lo niґtrīl) a colorless halogenated… …   Medical dictionary


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