Propionitrile

Propionitrile
Skeletal formula of propanenitrile	Skeletal formula of propanenitrile with all explicit hydrogens added
Names
	IUPAC name Propanenitrile
	Other names Cyanoethane; Ethyl cyanide; Propionitrile; Propylnitrile;
Identifiers
CAS Number	107-12-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	773680
ChEBI	CHEBI:26307;
ChEMBL	ChEMBL15871 ;
ChemSpider	7566 ;
ECHA InfoCard	100.003.151
EC Number	203-464-4;
MeSH	propionitrile
PubChem CID	7854;
RTECS number	UF9625000;
UNII	E16N05FX3S ;
UN number	2404
CompTox Dashboard (EPA)	DTXSID1021879 ;
	InChI InChI=1S/C3H5N/c1-2-3-4/h2H2,1H3 Key: FVSKHRXBFJPNKK-UHFFFAOYSA-N ;
	SMILES CCC#N;
Properties
Chemical formula	C3H5N
Molar mass	55.080 g·mol−1
Appearance	Colourless liquid
Odor	sweetish, pleasant, ethereal
Density	772 mg mL−1
Melting point	−100 to −86 °C; −148 to −123 °F; 173 to 187 K
Boiling point	96 to 98 °C; 205 to 208 °F; 369 to 371 K
Solubility in water	11.9% (20 °C)
log P	0.176
Vapor pressure	270 μmol Pa−1 kg−1
Refractive index (nD)	1.366
Thermochemistry
Heat capacity (C)	105.3 J K−1 mol−1
Std molar; entropy (S⦵298)	189.33 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	15.5 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−1.94884–−1.94776 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H300, H310, H319, H332
Precautionary statements	P210, P264, P280, P301+P310, P302+P350, P305+P351+P338
Flash point	6 °C (43 °F; 279 K)
Explosive limits	3.1%-?
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	39 mg kg−1 (oral, rat)
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 6 ppm (14 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related alkanenitriles	Acetonitrile; Aminopropionitrile; Malononitrile; Pivalonitrile; Butyronitrile; Succinonitrile;
Related compounds	DBNPA
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^[7]

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):^[7]

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).^[7] Propanenitrile has been determined to be teratogenic due to the metabolic release of cyanide.^[8]

In 1979, the Kalama (Vega) plant in Beaufort, South Carolina experienced an explosion during the production of propanenitrile by nickel-catalyzed reduction of acrylonitrile.^[9] This site is now one of the two Superfund cleanup sites in South Carolina.^[9]

References

^ ^a ^b "Propionitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Identification. Retrieved 1 November 2013.
^ Merck Index, 11th Edition, 7839
^ CRC Handbook of Chemistry and Physics, 52nd Ed., p. D-153
^ HSDB: Propionitrile, TOXNET, U.S. National Library of Medicine, retrieved 30 Oct 2015
^ "propionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 6 June 2012.
^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0530". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c 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
^ Willhite, Calvin C.; Ferm, Vergil H.; Smith, Roger P. (1981). "Teratogenic effects of aliphatic nitriles". Teratology. 23 (3): 317–323. doi:10.1002/tera.1420230306. PMID 6266064.
^ ^a ^b First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina, United States Environmental Protection Agency

External links

[pocketguide-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] HSDB: Propionitrile, TOXNET, U.S. National Library of Medicine, retrieved 30 Oct 2015

[5] "propionitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 6 June 2012.

[PGCH-6] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0530". National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-7] 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

[8] Willhite, Calvin C.; Ferm, Vergil H.; Smith, Roger P. (1981). "Teratogenic effects of aliphatic nitriles". Teratology. 23 (3): 317–323. doi:10.1002/tera.1420230306. PMID 6266064.

[EPA-9] First Five-Year Review Report for Kalama Specialty Chemicals, Beaufort, Beaufort County, South Carolina, United States Environmental Protection Agency

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