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Acrylonitrile

Acrylonitrile
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Names
Preferred IUPAC name
Prop-2-enenitrile
Other names
Acrylonitrile
2-Propenenitrile
Cyanoethene,
Vinylcyanide (VCN)
Cyanoethylene
Propenenitrile
Identifiers
107-13-1 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:28217 YesY
ChEMBL ChEMBL445612 YesY
ChemSpider 7567 YesY
ECHA InfoCard 100.003.152
EC Number 608-003-00-4
KEGG C01998 YesY
PubChem 7855
RTECS number AT5250000
UNII MP1U0D42PE YesY
UN number 1093
Properties
C3H3N
Molar mass 53.06 g·mol−1
Appearance Colourless liquid
Density 0.81 g/cm3
Melting point −84 °C (−119 °F; 189 K)
Boiling point 77 °C (171 °F; 350 K)
70 g/L
Vapor pressure 83 mmHg
Hazards
Main hazards flammable,
reactive,
toxic,
potential occupational carcinogen
Safety data sheet ICSC 0092
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −1 °C; 30 °F; 272 K
471 °C (880 °F; 744 K)
Explosive limits 3–17%
Lethal dose or concentration (LD, LC):
500 ppm (rat, 4 hr)
313 ppm (mouse, 4 hr)
425 ppm (rat, 4 hr)
260 ppm (rabbit, 4 hr)
575 ppm (guinea pig, 4 hr)
636 ppm (rat, 4 hr)
452 ppm (human, 1 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 2 ppm C 10 ppm [15-minute] [skin]
REL (Recommended)
Ca TWA 1 ppm C 10 ppm [15-minute] [skin]
IDLH (Immediate danger)
85 ppm
Related compounds
Related compounds
acrylic acid,
acrolein
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Acrylonitrile is an organic compound with the formula CH2CHCN. It is a colorless volatile liquid, although commercial samples can be yellow due to impurities. 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.

Acrylonitrile is produced by catalytic ammoxidation of propylene, also known as the SOHIO process. In 2002, world production capacity was estimated at 5 million tonnes per year. Acetonitrile and hydrogen cyanide are significant byproducts that are recovered for sale. In fact, the 2008–2009 acetonitrile shortage was caused by a decrease in demand for acrylonitrile.

In the SOHIO process, propylene, ammonia, and air (oxidizer) are passed through a fluidized bed reactor containing the catalyst at 400–510 °C and 50–200 kPag. The reactants pass through the reactor only once, before being quenched in aqueous sulfuric acid. Excess propylene, carbon monoxide, carbon dioxide, and dinitrogen that do not dissolve are vented directly to the atmosphere, or are incinerated. The aqueous solution consists of acrylonitrile, acetonitrile, hydrocyanic acid, and ammonium sulfate (from excess ammonia). A recovery column removes bulk water, and acrylonitrile and acetonitrile are separated by distillation. Historically, one of the first successful catalysts was bismuth phosphomolybdate supported on silica as a heterogeneous catalyst. Further improvements have since been made.


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