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Propionitrile

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Propionitrile

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IUPAC name
Propanenitrile[4]
Other names
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773680 107-12-0 7pxY ChEBI CHEBI:26307 ChEMBL ChEMBL15871 7pxN ChemSpider 7566 7pxY EC number 203-464-4 Jmol-3D images Image MeSH propionitrile PubChem Template:Chembox PubChem/format RTECS number UF9625000 UN number 2404 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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This page is a soft redirect.- C3H5N Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Appearance Colourless liquid Odor sweetish, pleasant, ethereal[5] Density 772 mg mL−1 Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". 11.9% (20°C)[5] log P 0.176 Vapor pressure 270 μmol Pa−1 kg−1 1.366 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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105.3 J K−1 mol−1 189.33 J K−1 mol−1 15.5 kJ mol−1 −1.94884–−1.94776 MJ mol−1 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Hazards

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GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) GHS signal word DANGER H225, H300, H310, H319, H332 P210, P264, P280, P301+310, P302+350, P305+351+338 EU classification Highly Flammable F Very Toxic T+ R-phrases R11, R20, R25, R27, R36 S-phrases S16, S36/37, S45 Flash point Script error: No such module "convert". Explosive limits 3.1%-?[5] 39 mg kg−1 (oral, rat) US health exposure limits (NIOSH):

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Related alkanenitriles
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxN verify (what is10pxY/10pxN?) Infobox references

Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.[6]

Production

The main industrial route to this nitrile is the hydrogenation of acrylonitrile. It is also prepared by the ammoxidation of propanol (propionaldehyde can also be used instead):[6]

CH3CH2CH2OH + O2 + NH3 → CH3CH2CN + 3 H2O

Propionitrile is a byproduct of the electrodimerisation of acrylonitrile to adiponitrile.

In the laboratory propanenitrile can also be produced by the dehydration of propionamide, by catalytic reduction of acrylonitrile, or by distilling ethyl sulfate and potassium cyanide.

Applications

Propionitrile is a solvent similar to acetonitrile but with a slightly higher boiling point. It is a precursor to propylamines by hydrogenation. It is a C-3 building block in the preparation of the drug flopropione by the Houben-Hoesch reaction.

Safety

Propanenitrile is poisonous but weakly with an LD50 of 230 mg/kg (rats, oral).[6] Propanenitrile has been determined to be teratogenic due to the metabolic release of cyanide.[7]

In 1979, the Kalama (Vega) plant in Beaufort, South Carolina experienced an explosion during the production of propanenitrile by nickel-catalyzed reduction of acrylonitrile.[8] This site is now one of the two Superfund cleanup sites in South Carolina.[8]

References

  1. 1.0 1.1 "Propionitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Identification. Retrieved 1 November 2013. 
  2. Merck Index, 11th Edition, 7839
  3. CRC Handbook of Chemistry and Physics, 52nd Ed., p. D-153
  4. "propionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 6 June 2012. 
  5. 5.0 5.1 5.2 5.3 5.4 5.5 "NIOSH Pocket Guide to Chemical Hazards #0530". National Institute for Occupational Safety and Health (NIOSH). 
  6. 6.0 6.1 6.2 Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363
  7. Willhite, Calvin C.; Ferm, Vergil H.; Smith, Roger P. (1981). "Teratogenic effects of aliphatic nitriles". Teratology 23 (3): 317–323. PMID 6266064. doi:10.1002/tera.1420230306. 
  8. 8.0 8.1 First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina, United States Environmental Protection Agency

External links

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