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Names | |||
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Preferred IUPAC name
Prop-2-enenitrile
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Other names | |||
Identifiers | |||
107-13-1 | |||
3D model (Jmol) |
Interactive image Interactive image |
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ChEBI | CHEBI:28217 | ||
ChEMBL | ChEMBL445612 | ||
ChemSpider | 7567 | ||
ECHA InfoCard | 100.003.152 | ||
EC Number | 608-003-00-4 | ||
KEGG | C01998 | ||
PubChem | 7855 | ||
RTECS number | AT5250000 | ||
UNII | MP1U0D42PE | ||
UN number | 1093 | ||
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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 |
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Safety data sheet | ICSC 0092 | ||
NFPA 704 | |||
Flash point | −1 °C; 30 °F; 272 K | ||
471 °C (880 °F; 744 K) | |||
Explosive limits | 3–17% | ||
Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration)
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500 ppm (rat, 4 hr) 313 ppm (mouse, 4 hr) 425 ppm (rat, 4 hr) |
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LCLo (lowest published)
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260 ppm (rabbit, 4 hr) 575 ppm (guinea pig, 4 hr) 636 ppm (rat, 4 hr) 452 ppm (human, 1 hr) |
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US health exposure limits (NIOSH): | |||
PEL (Permissible)
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TWA 2 ppm C 10 ppm [15-minute] [skin] | ||
REL (Recommended)
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Ca TWA 1 ppm C 10 ppm [15-minute] [skin] | ||
IDLH (Immediate danger)
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85 ppm | ||
Related compounds | |||
Related compounds
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acrylic acid, acrolein |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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what is ?) | (|||
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.