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Acetonitrile

Acetonitrile
Acetonitrile

Identifiers CAS number PubChem ChemSpider UNII EC number UN number MeSH ChEBI ChEMBL RTECS number Beilstein Reference Gmelin Reference Jmol-3D images 75-05-8 6342 6102
[2] [3] [4] [1]

Z072SB282N 200-835-2 1648 acetonitrile


[5]

[6] [7]

CHEBI:38472

CHEMBL45211 AL7700000 741857 895 Image 1 Properties


[9]

[8]

Molecular formula Molar mass Appearance Density Melting point Boiling point Solubility in water log P Vapor pressure k
H a

CHN
2 3

41.05 g mol1 Colorless liquid 786 mg mL1 46 to 44C; 51 to 47F; 227 to 229K 81.3 to 82.1C; 178.2 to 179.7F; 354.4 to 355.2K Miscible 0.334 9.71 kPa (at 20.0 C) 530 mol Pa1 kg1 25

Acidity (pK )

Acetonitrile

2
Basicity (pKb) max Absorbance Refractive index (nD) 11 195 nm 0.10 1.344 Thermochemistry Std enthalpy of formation fHo298 Std enthalpy of combustion cHo298 Standard molar entropy So298 Specific heat capacity, C 40.1640.96 kJ mol1

1256.031256.63 kJ mol1

149.62 J K1 mol1

91.69 J K Hazards

mol

MSDS GHS pictograms

External MSDS

GHS signal word GHS hazard statements GHS precautionary statements EU Index EU classification

DANGER H225, H302, H312, H319, H332 P210, P280, P305+351+338 608-001-00-3

F R-phrases S-phrases NFPA 704

Xn

R11, R20/21/22, R36 (S1/2), S16, S36/37

Flash point Autoignition temperature Explosive limits LD


50

2.0C; 35.6F; 275.1K 523.0C; 973.4F; 796.1K 4.416.0%


2 g kg1 (dermal, rabbit) 2.46 g kg1 (oral, rat)

Related compounds

Acetonitrile

3
Related alkanenitriles

Hydrogen cyanide Thiocyanic acid Cyanogen iodide Cyanogen bromide Cyanogen chloride Cyanogen fluoride Aminoacetonitrile Glycolonitrile Cyanogen Propanenitrile Aminopropionitrile Malononitrile Pivalonitrile Acetone cyanohydrin

Related compounds

DBNPA Supplementary data page

Structure and properties Thermodynamic data Spectral data


(verify) [10]

n, r, etc. Phase behaviour Solid, liquid, gas UV, IR, NMR, MS

(what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25C (77F), 100kPa)

Infobox references

Acetonitrile is the chemical compound with the formula CH 3CN. This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not classed as organic). It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene.[11] In the laboratory, it is used as a medium-polarity solvent that is miscible with water and range of organic solvents, but not saturated hydrocarbons. It has a convenient liquid range and a high dielectric constant of 38.8. With a dipole moment of 3.92D,[12] acetonitrile dissolves a wide range of ionic and nonpolar compounds and is useful as a mobile phase in HPLC and LC-MS. The N-C-C skeleton is linear with a short C-N distance of 1.16 .[13] Acetonitrile was first prepared in 1847 by the French chemist Jean-Baptiste Dumas.[14]

Applications
Acetonitrile is used mainly as a solvent in the purification of butadiene in refineries. It is widely used in battery applications because of its relatively high dielectric constant and ability to dissolve electrolytes. For similar reasons it is a popular solvent in cyclic voltammetry. Its low viscosity and low chemical reactivity make it a popular choice for High-performance liquid chromatography. Acetonitrile plays a significant role as the dominant solvent used in the manufacture of DNA oligonucleotides from monomers. Industrially, it is used as a solvent for the manufacture of pharmaceuticals and photographic film.

Acetonitrile

Organic synthesis
Acetonitrile is a common two-carbon building block in organic synthesis of many useful chemicals, including acetamidine hydrochloride, thiamine, and -napthaleneacetic acid. Its reaction with cyanogen chloride affords malononitrile.

Ligand in coordination chemistry


In inorganic chemistry, acetonitrile is employed as a solvent and often an easily displaceable ligand. For example, PdCl 2(CH 3CN) 2 is prepared by heating a suspension of (polymeric) palladium chloride in acetonitrile: PdCl 2 + 2 CH 3CN PdCl 2(CH 3CN)
2

A related complex is [Cu(MeCN)4]+. The CH 3CN groups in these complexes are rapidly displaced by many other ligands.

Production
Acetonitrile is a by-product from the manufacture of acrylonitrile. Most is combusted to support the intended process but an estimated several thousand tons are retained for the above mentioned applications. Production trends for acetonitrile thus generally follow those of acrylonitrile. Acetonitrile can also be produced by many other methods, but these are of no commercial importance as of 2002. Illustrative routes are by dehydration of acetamide or by hydrogenation of mixtures of carbon monoxide and ammonia. The main distributors of acetonitrile in the world are: INEOS, Purification Technologies Inc, BioSolve BV, Carlo Erba Reagents, Panreac, J.T. Baker Chemical, VWR, Sigma Aldrich, and Petrolchem Trading Ltd. In 1992[15], 32.3 million pounds (14,700 t) of acetonitrile were produced in the US.

Acetonitrile shortage in 20082009


Starting in October 2008, the worldwide supply of acetonitrile was low because Chinese production was shut down for the Olympics. Furthermore, a U.S. factory was damaged in Texas during Hurricane Ike. Owing to the global economic slowdown, the production of acrylonitrile that is used in acrylic fibers and acrylonitrile-butadiene-styrene (ABS) resins decreased. Because acetonitrile is a byproduct in the production of acrylonitrile, its production has also decreased. The global shortage of acetonitrile continued through early 2009.

Acetonitrile

Safety
Toxicity
Acetonitrile has only a modest toxicity in small doses. It can be metabolised to produce hydrogen cyanide, which is the source of the observed toxic effects. Generally the onset of toxic effects is delayed, due to the time required for the body to metabolize acetonitrile to cyanide (generally about 212 hours). Cases of acetonitrile poisoning in humans (or, to be more specific, of cyanide poisoning after exposure to acetonitrile) are rare but not unknown, by inhalation, ingestion and (possibly) by skin absorption. The symptoms, which do not usually appear for several hours after the exposure, include breathing difficulties, slow pulse rate, nausea, and vomiting: Convulsions and coma can occur in serious cases, followed by death from respiratory failure. The treatment is as for cyanide poisoning, with oxygen, sodium nitrite, and sodium thiosulfate among the most commonly used remedies. It has been used in formulations for nail polish remover, despite its low but significant toxicity.[16] Acetone and ethyl acetate are often preferred as safer for domestic use, and acetonitrile has been banned in cosmetic products in the European Economic Area since March 2000.[17] Metabolism and excretion
Compound Acetonitrile Propionitrile Butyronitrile Malononitrile Acrylonitrile Potassium cyanide Brain cyanide concentration (g/kg) 285 50884 437106 649209 395106 748200 Oral LD50 (mg/kg) 2460 40 50 60 90 10

Ionic cyanide concentrations measured in the brains of Sprague-Dawley rats one hour after oral administration of an LD50 of various nitriles.

In common with other nitriles, acetonitrile can be metabolised in microsomes, especially in the liver, to produce hydrogen cyanide, as was first shown by Pozzani et al. in 1959. The first step in this pathway is the oxidation of acetonitrile to glycolonitrile by an NADPH-dependent cytochrome P450 monooxygenase. The glycolonitrile then undergoes a spontaneous decomposition to give hydrogen cyanide and formaldehyde. Formaldehyde, a toxin and a carcinogen on its own, is further oxidized to formic acid, which is another source of toxicity. The metabolism of acetonitrile is much slower than that of other nitriles, which accounts for its relatively low toxicity. Hence, one hour after administration of a potentially lethal dose, the concentration of cyanide in the rat brain was one-twentieth that for a propionitrile dose 60 times lower (see table). The relatively slow metabolism of acetonitrile to hydrogen cyanide allows more of the cyanide produced to be detoxified within the body to thiocyanate (the rhodanese pathway). It also allows more of the acetonitrile to be excreted unchanged before it is metabolised. The main pathways of excretion are by exhalation and in the urine.

Acetonitrile

References
[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=75-05-8 [2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=6342 [3] http:/ / www. chemspider. com/ Chemical-Structure. 6102. html [4] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=Z072SB282N [5] http:/ / esis. jrc. ec. europa. eu/ lib/ einecs_IS_reponse. php?genre=ECNO& entree=200-835-2 [6] http:/ / www. nlm. nih. gov/ cgi/ mesh/ 2007/ MB_cgi?mode=& term=acetonitrile [7] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=38472 [8] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL45211 [9] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CC%23N [10] http:/ / en. wikipedia. org/ w/ index. php?title=Special:ComparePages& rev1=477239538& page2=Acetonitrile [11] (http:/ / www. industrialchemistry. info/ 100pagesAddict3. pdf), Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 76. [12] Steiner, P. A., and Gordy, W., 1966, J. molec. Spectrosc., 21, 291. [13] Karakida, Ken-ichi, Tsutomu Fukuyama, and Kozo Kuchitsu. "Molecular Structures of Hydrogen Cyanide and Acetonitrile as Studied by Gas Electron Diffraction." Bulletin of the Chemical Society of Japan 47.2 (1974): 299-304. [14] Dumas (1847) "Action de l'acide phosphorique anhydre sur les sels ammoniacaux" (http:/ / books. google. com/ books?id=IWFEAQAAIAAJ& pg=PA384#v=onepage& q& f=false) (Action of anhydrous phosphoric acid on ammonium salts), Comptes rendus, 25: 383-384. [15] http:/ / en. wikipedia. org/ w/ index. php?title=Acetonitrile& action=edit [16] At least two cases have been reported of accidental poisoning of young children by acetonitrile-based nail polish remover, one of which was fatal: [17] Twenty-Fifth Commission Directive 2000/11/EC of 10 March 2000 adapting to technical progress Annex II to Council Directive 76/768/EEC on the approximation of laws of the Member States relating to cosmetic products. (http:/ / eur-lex. europa. eu/ LexUriServ/ LexUriServ. do?uri=OJ:L:2000:065:0022:0025:EN:PDF) OJEC L65 of 2000-03-14, pp. 2225.

External links
WebBook page for C2H3N (http://webbook.nist.gov/cgi/cbook.cgi?ID=C75058) International Chemical Safety Card 0088 (http://www.inchem.org/documents/icsc/icsc/eics0088.htm) National Pollutant Inventory - Acetonitrile fact sheet (http://www.npi.gov.au/database/substance-info/ profiles/4.html) NIOSH Pocket Guide to Chemical Hazards (http://www.cdc.gov/niosh/npg/npgd0006.html) Chemical Summary for Acetonitrile (CAS No. 75-05-8) (http://www.epa.gov/chemfact/s_acenit.txt), Office of Pollution Prevention and Toxics, U.S. Environmental Protection Agency Simulation of acetonitrile (http://www.layruoru.com/dokuwiki/doku.php/solvents)

Article Sources and Contributors

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Acetonitrile Source: http://en.wikipedia.org/w/index.php?oldid=590269794 Contributors: Alteen88, Alvis, Ambix, Aschwaid, Aussie Alchemist, Beetstra, Benjah-bmm27, BredoteauU2, Brossow, Browneyedgirl13, CMSherwood, Chem-awb, ChemistPyrex, Chemportal, Chris the speller, Christian75, Cian584, Cwkmail, Dandelyonn, DePiep, Dekkanar, Denelson83, Doremo, Drphilharmonic, Edgar181, Ej159, Ekem, Elikrieg, Epop fr, Ferbrunnen, Foobar, Gene Nygaard, Gentgeen, Hakan Kay, HenkvD, Hermann Luyken, Hnobil, Horoporo, IR8D8R, Ilovebees, Iohannes Animosus, Izmaelt, Jdfalk, Jrtayloriv, Jynto, Karen Johnson, LHcheM, Lamro, Leridant, Louisajb, M stone, Malbi, Materialscientist, Mehcp, Morstar, Mortense, Mullet, Murtasa, Nick Y., Nicke L, Nono64, NuShrike, Ogre lawless, Peter Corbett, Physchim62, Pikiwyn, Plasmic Physics, Poorjon, Puppy8800, RHWoodman, Radiotrefoil, Raffinate2, Rich Farmbrough, Rifleman 82, Rjwilmsi, Russoc4, Rwessel, Saehrimnir, Saehry, Sbyrnes321, Scythe33, Skipmac, Smokefoot, Spiffy sperry, Steve Quinn, Suisui, Superm401, Topbanana, Tyrael123, Ugen64, V8rik, Vchorozopoulos, Vitodang, Wickey-nl, WolfmanSF, YanA, Yellowdesk, Za3bolla elolla, Ziel, Zombiejesus, ~K, 112 anonymous edits

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