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Revision as of 16:13, 6 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 21:05, 26 November 2024 edit undo85.249.171.76 (talk)No edit summaryTags: Manual revert Mobile edit Mobile web edit
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			{{Short description|Organic compound (CH3−C≡N); Simplest organic nitrile}}
	{{chembox
			{{Distinguish|Acetyl cyanide}}
	| Watchedfields = changed
			{{Chembox
	| verifiedrevid = 409346868
			| Watchedfields = changed
	| ImageFile1_Ref = {{chemboximage|correct|??}}
			| verifiedrevid = 477239538
	| ImageFile1 = Acetonitrile-2D.png
			| ImageFileL1 = Acetonitrile-2D-skeletal.svg
	| ImageSize1 = 180px
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageFile2 = Acetonitrile-3D-vdW.png
			| ImageNameL1 = Skeletal formula of acetonitrile
	| ImageSize2 = 200px
	| IUPACName = Acetonitrile		| ImageFileR1 = Acetonitrile-2D-flat.svg
			| ImageFileR1_Ref = {{chemboximage|correct|??}}
	| OtherNames = methyl cyanide; cyanomethane; ethyl nitrile; ethanenitrile; methanecarbonitrile
			| ImageNameR1 = Skeletal formula of acetonitrile with all explicit hydrogens added
	| Section1 = {{Chembox Identifiers
			| ImageFileL2 = Acetonitrile-3D-balls.png
	| Abbreviations =
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ImageFileL2_Ref = {{chemboximage|correct|??}}
			| ImageNameL2 = Ball and stick model of acetonitrile
	| ChemSpiderID = 6102
			| ImageFileR2 = Acetonitrile-3D-vdW.png
	| UNII_Ref = {{fdacite|correct|FDA}}
			| ImageFileR2_Ref = {{chemboximage|correct|??}}
	| UNII = Z072SB282N
			| ImageNameR2 = Spacefill model of acetonitrile
	| InChIKey = WEVYAHXRMPXWCK-UHFFFAOYAJ
			| ImageFile3 = Asetonitril.png
	| SMILES1 = CC#N
			| ImageSize3 = 100px
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| PIN = Acetonitrile<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 902 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
	| StdInChI = 1S/C2H3N/c1-2-3/h1H3
			| SystematicName = Ethanenitrile<ref name=iupac2013 />
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| OtherNames = {{Unbulleted list|Cyanomethane<ref name=Pella>{{Cite web|title=Material Safety Data Sheet: Acetonitrile|url=http://www.tedpella.com/MSDS_html/18612%20msds.pdf|website = TedPella.com}}</ref>|Ethyl nitrile<ref name=Pella/>|Methanecarbonitrile<ref name=Pella/>|Methyl cyanide<ref name=Pella/>|MeCN |ACN
	| StdInChIKey = WEVYAHXRMPXWCK-UHFFFAOYSA-N
			}}
			| Section1 = {{Chembox Identifiers
	| CASNo = 75-05-8		| CASNo = 75-05-8
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo_Comment = <ref>http://www.sigmaaldrich.com/chemistry/solvents/acetonitrile-center.html</ref>
	| CASNo_Ref = {{cascite|correct|CAS}}
	| EINECS =
	| PubChem = 6342		| PubChem = 6342
			| ChemSpiderID = 6102
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| UNII = Z072SB282N
			| UNII_Ref = {{fdacite|correct|FDA}}
			| EINECS = 200-835-2
			| UNNumber = 1648
			| MeSHName = acetonitrile
			| ChEBI = 38472
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 45211		| ChEMBL = 45211
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| SMILES = N#CC
	| InChI = 1/C2H3N/c1-2-3/h1H3
	| RTECS = AL7700000		| RTECS = AL7700000
			| Beilstein = 741857
	| MeSHName =
	| ChEBI = 38472		| Gmelin = 895
			| SMILES = CC#N
	| KEGG_Ref = {{keggcite|correct|kegg}}
			| StdInChI = 1S/C2H3N/c1-2-3/h1H3
	| KEGG =
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| ATCCode_prefix =
			| StdInChIKey = WEVYAHXRMPXWCK-UHFFFAOYSA-N
	| ATCCode_suffix =
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| ATC_Supplemental =}}
			}}
	| Section2 = {{Chembox Properties
			| Section2 = {{Chembox Properties
	|C=2|H=3|N=1
			| C=2 | H=3
	| Appearance = colorless liquid
			| N = 1
	| Density = 0.777 g/mL liquid
			| Appearance = Colorless liquid
	| MeltingPt = −45 °C
			| Odor = Faint, distinct, fruity
	| Melting_notes =
			| Density = 0.786 g/cm<sup>3</sup> at 25°C
	| BoilingPt = 82 °C
			| MeltingPtK = 227 to 229
	| Boiling_notes =
			| BoilingPtK = 354.4 to 355.2
	| Solubility = miscible
			| Solubility = Miscible
	| SolubleOther = organic solvents
	| Solvent =		| LogP = −0.334
			| MagSus = {{val|-28.0|e=-6|u=cm<sup>3</sup>/mol}}
			| VaporPressure = 9.71 kPa (at 20.0&nbsp;°C)
			| HenryConstant = 530 μmol/(Pa·kg)
	| pKa = 25		| pKa = 25
			| LambdaMax = 195&nbsp;nm
	| pKb = }}
			| Absorbance = ≤0.10
	| Section7 = {{Chembox Hazards
			| RefractIndex = 1.344
	| EUClass = Flammable, harmful
	| EUIndex =		| Dipole = 3.92 D
			}}
	| MainHazards =
			| Section3 = {{Chembox Thermochemistry
			| DeltaHf = 40.16–40.96 kJ/mol
			| DeltaHc = −1256.03 – −1256.63 kJ/mol
			| Entropy = 149.62 J/(K·mol)
			| HeatCapacity = 91.69 J/(K·mol)
			}}
			| Section4 = {{Chembox Hazards
			| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
			| GHSSignalWord = '''DANGER'''
			| HPhrases = {{H-phrases|225|302|312|319|332}}
			| PPhrases = {{P-phrases|210|280|305+351+338}}
	| NFPA-H = 2		| NFPA-H = 2
	| NFPA-F = 3		| NFPA-F = 3
	| NFPA-R = 0		| NFPA-R = 0
	| NFPA-O = 0		| FlashPtC = 2.0
			| AutoignitionPtC = 523.0
	| RPhrases = {{R11}}, {{R20/21/22}}, {{R36}}
			| ExploLimits = 4.4–16.0%
	| SPhrases = {{(S1/2)}}, {{S16}}, {{S36/37}}
			| LD50 = {{Unbulleted list|2 g/kg <small>(dermal, rabbit)</small>|2.46 g/kg <small>(oral, rat)</small>}}
	| RSPhrases =
			| PEL = TWA 40 ppm (70 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0006}}</ref>
	| FlashPt = 2 °C
			| REL = TWA 20 ppm (34 mg/m<sup>3</sup>)<ref name=NIOSH/>
	| Autoignition =
			| IDLH = 500 ppm<ref name=NIOSH/>
	| ExploLimits =
			| LC50 = 5655 ppm (guinea pig, 4 hr)<br/>2828 ppm (rabbit, 4 hr)<br/>53,000 ppm (rat, 30 min)<br/>7500 ppm (rat, 8 hr)<br/>2693 ppm (mouse, 1 hr)<ref name=IDLH>{{IDLH|75058|Acetonitrile}}</ref>
	| PEL = }}
			| LCLo = 16,000 ppm (dog, 4 hr)<ref name=IDLH/>
	| Section8 = {{Chembox Related
	| OtherAnions =
	| OtherCations =
	| OtherFunctn = ], ]
	| Function = ]s
	| OtherCpds = ], ], ]}}
	}}		}}
			| Section5 = {{Chembox Related
	'''Acetonitrile''' is the ] with ] CH<sub>3</sub>CN. This colourless liquid is the simplest organic ]. It is produced mainly as a byproduct of ] manufacture. It is mainly used as a ] in purification of ].<ref name="ashford">, Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 76.</ref>
			| OtherFunction_label = alkanenitriles
			| OtherFunction = {{Unbulleted list|]|]|]|]|]|]|]|]|]|]|]|]|]|]}}
			| OtherCompounds = ]
			}}
			}}
			'''Acetonitrile''', often abbreviated '''MeCN''' ('''methyl cyanide'''), is the ] with the ] {{chem2|CH3CN}} and ] {{chem2|H3C\sC\tN}}. This colourless liquid is the simplest organic ] (] is a simpler nitrile, but the ] anion is not classed as ]). It is produced mainly as a byproduct of ] manufacture. It is used as a ] in ] and in the purification of ].<ref name="ashford">{{cite web|url=http://www.industrialchemistry.info/100pagesAddict3.pdf |title=Archived copy |access-date=2011-03-31 |url-status=dead |archive-url=https://web.archive.org/web/20110516233056/http://www.industrialchemistry.info/100pagesAddict3.pdf |archive-date=2011-05-16 |work=Ashford's Dictionary of Industrial Chemicals, Third edition |page=76 }}</ref> The {{chem2|N\tC\sC}} skeleton is ] with a short {{chem2|C\tN}} ] of 1.16&nbsp;].<ref>{{cite journal|last1=Karakida|first1=Ken'ichi|last2=Fukuyama|first2=Tsutomu|last3=Kuchitsu|first3=Kozo|year=1974|title=Molecular Structures of Hydrogen Cyanide and Acetonitrile as Studied by Gas Electron Diffraction|journal=Bulletin of the Chemical Society of Japan|volume=47|issue=2|pages=299–304|doi=10.1246/bcsj.47.299|doi-access=free}}</ref>
			Acetonitrile was first prepared in 1847 by the French chemist ].<ref>{{cite journal | last1 = Dumas | first1 = J.-B. | year = 1847 | title = Action de l'acide phosphorique anhydre sur les sels ammoniacaux |trans-title=Action of anhydrous phosphoric acid on ammonium salts | url = https://books.google.com/books?id=IWFEAQAAIAAJ&pg=PA384| journal = Comptes rendus | volume = 25 | pages = 383–384 }}</ref>
	In the laboratory, it is used as a medium-polarity solvent that is ] with water and has a convenient liquid range. With a ] of 3.84&nbsp;], acetonitrile dissolves a wide range of ionic and nonpolar compounds and is useful as a mobile phase in ] and LCMS.
	==Applications==		==Applications==
	Acetonitrile is used mainly as a solvent in the purification of ] in refineries.		Acetonitrile is used mainly as a solvent in the purification of ] in refineries. Specifically, acetonitrile is fed into the top of a ] filled with ]s including butadiene, and as the acetonitrile falls down through the column, it absorbs the butadiene which is then sent from the bottom of the tower to a second separating tower. Heat is then employed in the separating tower to separate the butadiene.
			In the laboratory, it is used as a medium-polarity ] solvent that is ] with water and a range of organic solvents, but not saturated hydrocarbons. It has a convenient range of temperatures at which it is a liquid, and a high ] of 38.8. With a ] of 3.92&nbsp;],<ref>{{cite journal|last1=Steiner|first1=P.&nbsp;A.|last2=Gordy|first2=W.|date=1966|title=Journal of Molecular Spectroscopy|url=http://www.sciencedirect.com/science/journal/00222852/21|volume=21|page=291}}</ref> acetonitrile dissolves a wide range of ionic and nonpolar compounds and is useful as a mobile phase in ] and ].
	It is widely used in battery applications because of its relatively high ] and ability to dissolve electrolytes. For similar reasons it is a popular solvent in ]. Its low viscosity and low chemical reactivity make it a popular choice for ]. 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 ]s and ].<ref name="ecb"/>
			It is widely used in ] applications because of its relatively high dielectric constant and ability to dissolve ]s. For similar reasons, it is a popular solvent in ].
			Its ultraviolet transparency ], low ] and low ] make it a popular choice for ] (HPLC).
			Acetonitrile plays a significant role as the dominant solvent used in ] from ]s.
			Industrially, it is used as a solvent for the manufacture of ]s and ].<ref name="ecb"/>
	===Organic synthesis===		===Organic synthesis===
	Acetonitrile is a common two-carbon building block in ]<ref>{{OrgSynth | author = DiBiase, S. A.; Beadle, J. R.; Gokel, G. W. | title = Synthesis of α,β-Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile | collvol = 7 | collvolpages = 108 | prep = cv7p0108}}</ref> of many useful chemicals, including ], ], ], and ].<ref name="encyc-toxic">{{Citation|title=Encyclopedia of Toxicology|editor=Philip Wexler|publisher=Elsevier|year=2005|edition=2nd|volume=Vol. 1|isbn=0-12-745354-7|pages=28–30}}</ref> Its reaction with ] affords ].<ref name = "ashford" />		Acetonitrile is a common two-carbon building block in ]<ref>{{OrgSynth | last1= DiBiase |first1=S.&nbsp;A. |last2=Beadle |first2=J.&nbsp;R. |last3=Gokel |first3=G.&nbsp;W. | title = Synthesis of α,β-Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile | collvol = 7 | collvolpages = 108 | prep = cv7p0108}}</ref> of many useful chemicals, including ], ], and ].<ref name="encyc-toxic">{{Citation|title=Encyclopedia of Toxicology|editor=Philip Wexler|publisher=Elsevier|year=2005|edition=2nd|volume=1|isbn=0-12-745354-7|pages=28–30}}</ref> Its reaction with ] affords ].<ref name = "ashford" />
			===As an electron pair donor===
			Acetonitrile has a free electron pair at the nitrogen atom, which can form many ]. Being weakly basic, it is an easily displaceable ]. For example, ] is prepared by heating a suspension of ] in acetonitrile:<ref>{{Cite book|title=Organic synthesis : concepts and methods|last=Jürgen-Hinrich.|first=Fuhrhop|date=2003|publisher=Wiley-VCH|others=Li, Guangtao, Dr.|isbn=9783527302727|edition=3rd, completely rev. and enl.|location=Weinheim|oclc=51068223|page=26}}</ref>
			:{{chem2|PdCl2 + 2 CH3CN -> PdCl2(CH3CN)2}}
			A related complex is ] {{chem2|+}}. The {{chem2|CH3CN}} groups in these complexes are rapidly displaced by many other ligands.
			It also forms Lewis adducts with group 13 ]s like ].<ref>B. Swanson, D. F. Shriver, J. A. Ibers, "Nature of the donor-acceptor bond in acetonitrile-boron trihalides. The structures of the boron trifluoride and boron trichloride complexes of acetonitrile", Inorg. Chem., 2969., volume 8, pp. 2182-2189, {{doi:10.1021/ic50080a032}}</ref> In ]s, it is possible to protonate acetonitrile.<ref name="Christe">{{cite journal|last1 = Haiges|first1=Ralf|last2=Baxter|first2=Amanda F.|last3=Goetz|first3=Nadine R.|last4=Axhausen|first4=Joachim A.|last5=Soltner|first5=Theresa|last6=Kornath|first6=Andreas|last7=Christe|first7=Kalr O.|title=Protonation of nitriles: isolation and characterization of alkyl- and arylnitrilium ions|journal=Dalton Transactions|year=2016|volume=45|issue=20|pages=8494–8499|doi=10.1039/C6DT01301E|pmid=27116374}}</ref>
	===Ligand in coordination chemistry===
	In ], acetonitrile is employed as a solvent and often an easily displaceable ]. For example, PdCl<sub>2</sub>(CH<sub>3</sub>CN)<sub>2</sub> is prepared by heating a suspension of (polymeric) ] in acetonitrile:
	:PdCl<sub>2</sub> + 2 CH<sub>3</sub>CN → PdCl<sub>2</sub>(CH<sub>3</sub>CN)<sub>2</sub>
	The CH<sub>3</sub>CN groups undergo rapid displacement by many other ligands.
	==Production==		==Production==
	Acetonitrile is a by-product from the manufacture of ].<ref name=Ullmann>{{Citation | last1 = Pollak | first1 = Peter | last2 = Romeder | first2 = G��Rard | last3 = Hagedorn | first3 = Ferdinand | last4 = Gelbke | first4 = Heinz-Peter | title = Nitriles | year = 2000 | doi = 10.1002/14356007.a17_363 | postscript = . }}</ref> Production trends for acetonitrile thus generally follow those of ]. 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 ] or by ] of mixtures of ] and ].<ref>{{Ref patent		Acetonitrile is a byproduct from the manufacture of ]. Most is combusted to support the intended process but an estimated several thousand tons are retained for the above-mentioned applications.<ref name=Ullmann>{{Ullmann| last1 = Pollak | first1 = Peter | last2 = Romeder | first2 = Gérard | last3 = Hagedorn | first3 = Ferdinand | last4 = Gelbke | first4 = Heinz-Peter | title = Nitriles | doi = 10.1002/14356007.a17_363 }}</ref> Production trends for acetonitrile thus generally follow those of ]. 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 ] or by ] of mixtures of ] and ].<ref>{{Cite patent
	|country= US		|country= US
	|number= 4179462		|number= 4179462
Line 103:		Line 136:
	|invent2=Olive, S.		|invent2=Olive, S.
	|assign1=]		|assign1=]
			}}</ref> In {{as of|1992|alt=1992}}, {{convert|14700|t|ST}} of acetonitrile were produced in the US.
	|assign2=
	|class=558/318
	}}</ref> The main distributors of acetonitrile in the world are: ], Purification Technologies Inc, ] BV, Carlo Erba Reagents, ], J.T. Baker Chemical, VWR, Sigma Aldrich, and Petrolchem Trading Ltd. In {{as of|1992|alt=1992}}, 32.3 million pounds (14,700 t) of acetonitrile were produced in the US.
	===Acetonitrile shortage in 2008–2009===		===Acetonitrile shortage in 2008–2009 ===
	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.<ref>{{Citation | first = Derek | last = Lowe | title = The Great Acetonitrile Shortage | year = 2009 | publisher = ] | url = http://pipeline.corante.com/archives/2009/01/22/the_great_acetonitrile_shortage.php}}</ref> Owing to the global economic slowdown, the production of acrylonitrile that is used in acrylic fibers and ] (ABS) resins decreased. Because acetonitrile is a byproduct in the production of ], its production has also decreased.<ref>Chemical & Engineering News, 86(47), p. 27 November 24, 2008</ref> The global shortage of acetonitrile continued through early 2009.		Starting in October 2008, the worldwide supply of acetonitrile was low because Chinese production was shut down for the ]. Furthermore, a U.S. factory was damaged in Texas during ].<ref>{{Cite web | first = Derek | last = Lowe | author-link = Derek Lowe (chemist) | title = The Great Acetonitrile Shortage | year = 2009 | publisher = ] | url = https://www.science.org/content/blog-post/great-acetonitrile-shortage}}</ref> Due to the global economic slowdown, the production of acrylonitrile used in acrylic fibers and ] (ABS) resins decreased. Acetonitrile is a byproduct in the production of ] and its production also decreased, further compounding the acetonitrile shortage.<ref>{{cite journal | author = A. Tullo | title = A Solvent Dries Up | journal = Chemical & Engineering News | volume = 86 | issue = 47 | pages = 27 | doi = 10.1021/cen-v086n047.p027| year = 2008 }}</ref> The global shortage of acetonitrile continued through early 2009.{{update inline|date=February 2018}}
	==Safety==		==Safety==
	===Toxicity===		===Toxicity===
	Acetonitrile has only a modest toxicity in small doses.<ref name="inrs">{{Citation | last = Institut National de Recherche et de Sécurité (INRS) | author-link = Institut National de Recherche et de Sécurité | title = Fiche toxicologique nº&nbsp;104&nbsp;: Acétonitrile | year = 2004 | place = Paris | publisher = ] | url = http://www.inrs.fr/inrs-pub/inrs01.nsf/IntranetObject-accesParReference/FT%20104/$File/ft104.pdf | isbn = 2-7389-1278-8}}</ref><ref name="encyc-toxic" /> It can be ] to produce ], which is the source of the observed toxic effects.<ref name="ecb">{{Citation | last = Spanish Ministry of Health | author-link = Ministry of Health (Spain) | title = Acetonitrile. Summary Risk Assessment Report | year = 2002 | place = ] | publisher = ] | url = http://ecb.jrc.it/DOCUMENTS/Existing-Chemicals/RISK_ASSESSMENT/SUMMARY/acetonitrilesum006.pdf | id = Special Publication I.01.65}}</ref><ref name="who">{{Citation | last = International Programme on Chemical Safety | author-link = International Programme on Chemical Safety | title = Environmental Health Criteria 154. Acetonitrile | year = 1993 | place = Geneva | publisher = ] | url = http://www.inchem.org/documents/ehc/ehc/ehc154.htm}}</ref><ref name="epa">{{Citation | first = Mark | last = Greenberg | title = Toxicological Review of Acetonitrile | year = 1999 | place = Washington, D.C. | publisher = ] | url = http://www.epa.gov/NCEA/iris/toxreviews/0205-tr.pdf | format = }} {{dead link|date=July 2010}}</ref> Generally the onset of toxic effects is delayed, due to the time required for the body to metabolize acetonitrile to cyanide (generally about 2–12 hours).<ref name="encyc-toxic" />		Acetonitrile has only modest toxicity in small doses.<ref name="encyc-toxic" /><ref name="inrs">{{Citation | last = Institut national de recherche et de sécurité (INRS) | author-link = Institut national de recherche et de sécurité | title = Fiche toxicologique no.&nbsp;104&nbsp;: Acétonitrile | year = 2004 | place = Paris | publisher = ] | url = http://www.inrs.fr/inrs-pub/inrs01.nsf/IntranetObject-accesParReference/FT%20104/$File/ft104.pdf | isbn = 2-7389-1278-8 | access-date = 2008-08-19 | archive-url = https://web.archive.org/web/20110728102249/http://www.inrs.fr/inrs-pub/inrs01.nsf/IntranetObject-accesParReference/FT%20104/$File/ft104.pdf | archive-date = 2011-07-28 | url-status = dead }}</ref> It can be ] to produce ], which is the source of the observed toxic effects.<ref name="ecb">{{Citation|last=Spanish Ministry of Health |author-link=Ministry of Health (Spain) |title=Acetonitrile. Summary Risk Assessment Report |year=2002 |place=] |publisher=] |url=http://ecb.jrc.it/DOCUMENTS/Existing-Chemicals/RISK_ASSESSMENT/SUMMARY/acetonitrilesum006.pdf |id=Special Publication I.01.65 |url-status=dead |archive-url=https://web.archive.org/web/20081217020910/http://ecb.jrc.it/DOCUMENTS/Existing-Chemicals/RISK_ASSESSMENT/SUMMARY/acetonitrilesum006.pdf |archive-date=2008-12-17 }}</ref><ref name="who">{{Citation | last = International Programme on Chemical Safety | author-link = International Programme on Chemical Safety | title = Environmental Health Criteria 154. Acetonitrile | year = 1993 | place = Geneva | publisher = ] | url = http://www.inchem.org/documents/ehc/ehc/ehc154.htm}}</ref><ref name="epa">{{Citation | first = Mark | last = Greenberg | title = Toxicological Review of Acetonitrile | year = 1999 | place = Washington, DC | publisher = ] | url = http://www.epa.gov/iris/toxreviews/0205tr.pdf }}</ref> Generally the onset of toxic effects is delayed, due to the time required for the body to metabolize acetonitrile to cyanide (generally about 2–12 hours).<ref name="encyc-toxic" />
	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.<ref name="who" /> 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 ], with ], ], and ] among the most commonly-used remedies.<ref name="who" />		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.<ref name="who" /> The symptoms, which do not usually appear for several hours after the exposure, include breathing difficulties, slow ], ], and vomiting. ]s and ] can occur in serious cases, followed by death from ]. The treatment is as for ], with ], ], and ] among the most commonly used emergency treatments.<ref name="who" />
	It has been used in formulations for ], despite its low but significant toxicity.<ref>At least two cases have been reported of accidental poisoning of young children by acetonitrile-based nail polish remover, one of which was fatal: {{Citation | last = Caravati | first = EM | coauthors = Litovitz, T | title = Pediatric cyanide intoxication and death from an acetonitrile-containing cosmetic | year = 1988 | journal = ] | volume = 260 | issue = 23 | pages = 3470–73 | pmid = 3062198 | doi = 10.1001/jama.260.23.3470}}</ref> ] and ] are often preferred as safer for domestic use, and acetonitrile has been banned in cosmetic products in the ] since March 2000.<ref> '']'' L65 of 2000-03-14, pp. 22–25.</ref>		It has been used in formulations for ], despite its toxicity. At least two cases have been reported of accidental poisoning of young children by acetonitrile-based nail polish remover, one of which was fatal.<ref>{{Cite journal | last1 = Caravati | first1 = E. M. |last2= Litovitz |first2= T. | title = Pediatric cyanide intoxication and death from an acetonitrile-containing cosmetic | year = 1988 | journal = ] | volume = 260 | issue = 23 | pages = 3470–73 | pmid = 3062198 | doi = 10.1001/jama.260.23.3470}}</ref> ] and ] are often preferred as safer for domestic use, and acetonitrile has been banned in cosmetic products in the ] since March 2000.<ref>{{cite journal|url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2000:065:0022:0025:EN:PDF|title=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|journal=]|volume=L65|date=2000-03-14|pages=22–25}}</ref>
	====Metabolism and excretion====		====Metabolism and excretion====
	{| class="wikitable" align="right" width=30%		{| class="wikitable" width=30%
	|-		|-
	! Compound		! Compound
	! Brain cyanide concentration (µg/kg)		! Cyanide, concentration in brain (μg/kg)
	! Oral {{LD50}} (mg/kg)		! Oral {{LD50}} (mg/kg)
	|-		|-
			| ]
	| '''Acetonitrile'''
	| align="center" | 28±5		| align="center" | 700&nbsp;±&nbsp;200
	| align="right" | 2460		| align="right" | 10
	|-		|-
	| ]		| ]
	| align="center" | 508±84		| align="center" | 510&nbsp;±&nbsp;80
	| align="right" | 40		| align="right" | 40
	|-		|-
	| ]		| ]
	| align="center" | 437±106		| align="center" | 400&nbsp;±&nbsp;100
	| align="right" | 50		| align="right" | 50
	|-		|-
	| ]		| ]
	| align="center" | 649±209		| align="center" | 600&nbsp;±&nbsp;200
	| align="right" | 60		| align="right" | 60
	|-		|-
	| ]		| ]
	| align="center" | 395±106		| align="center" | 400&nbsp;±&nbsp;100
	| align="right" | 90		| align="right" | 90
	|-		|-
			| '''Acetonitrile'''
	| ]
	| align="center" | 748±200		| align="center" | 28&nbsp;±&nbsp;5
	| align="right" | 10		| align="right" | 2460
			|-
			| '''Table salt (NaCl)'''
			| align="center" {{n/a}}
			| align="right" | 3000
	|-		|-
	| colspan=3 | <small>Ionic cyanide concentrations measured in the brains of Sprague-Dawley rats one hour after oral administration of an {{LD50}} of various nitriles.</small><ref name="ratdata">{{Citation | last = Ahmed | first = AE | coauthors = Farooqui, MYH | title = Comparative toxicities of aliphatic nitriles | journal = Toxicol. Lett. | year = 1982 | volume = 12 | pages = 157–64 | doi = 10.1016/0378-4274(82)90179-5 | issue = 2–3}}</ref>		| colspan=3 | <small>Ionic cyanide concentrations measured in the brains of Sprague-Dawley rats one hour after oral administration of an {{LD50}} of various nitriles.</small><ref name="ratdata">{{Citation | last1 = Ahmed | first1 = A.&nbsp;E. |last2= Farooqui |first2=M.&nbsp;Y.&nbsp;H. | title = Comparative toxicities of aliphatic nitriles | journal = Toxicol. Lett. | year = 1982 | volume = 12 | pages = 157–64 | doi = 10.1016/0378-4274(82)90179-5 | issue = 2–3 | pmid=6287676}}</ref>
	|-		|-
	|}		|}
	In common with other ]s, acetonitrile can be ] in ]s, especially in the liver, to produce ], as was first shown by Pozzani ''et al.'' in 1959.<ref>{{Citation | last = Pozzani | first = UC | coauthors = Carpenter, CP; Palm, PE; Weil, CS; Nair, JH | title = An investigation of the mammalian toxicity of acetonitrile | journal = J. Occup. Med. | year = 1959 | volume = 1 | pages = 634–642 | doi = 10.1097/00043764-195912000-00003 | pmid = 14434606 | issue = 12}}</ref> The first step in this pathway is the oxidation of acetonitrile to ] by an ]-dependent ] ]. The glyconitrile then undergoes a spontaneous decondensation to give hydrogen cyanide and ].<ref name="inrs" /><ref name="who" />		In common with other ]s, acetonitrile can be ] in ]s, especially in the liver, to produce ], as was first shown by Pozzani ''et al.'' in 1959.<ref>{{Citation | last1 = Pozzani | first1 = U.&nbsp;C. |last2= Carpenter |first2=C.&nbsp;P.|last3= Palm |first3= P.&nbsp;E.|last4= Weil|first4= C.&nbsp;S.|last5= Nair |first5=J.&nbsp;H. | title = An investigation of the mammalian toxicity of acetonitrile | journal = J. Occup. Med. | year = 1959 | volume = 1 | pages = 634–642 | doi = 10.1097/00043764-195912000-00003 | pmid = 14434606 | issue = 12}}</ref> The first step in this pathway is the oxidation of acetonitrile to ] by an ]-dependent ] ]. The glycolonitrile then undergoes a spontaneous decomposition to give hydrogen cyanide and ].<ref name="inrs" /><ref name="who" /> Formaldehyde, a toxin and a carcinogen on its own, is further oxidized to ], 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 ] dose 60 times lower (see table).<ref name="ratdata" />		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 {{frac|20}} that for a ] dose 60 times lower (see table).<ref name="ratdata" />
	The relatively slow metabolism of acetonitrile to hydrogen cyanide allows more of the cyanide produced to be detoxified within the body to ] (the ] 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.<ref name="inrs" /><ref name="who" /><ref name="epa" />		The relatively slow metabolism of acetonitrile to hydrogen cyanide allows more of the cyanide produced to be detoxified within the body to ] (the ] 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.<ref name="inrs" /><ref name="who" /><ref name="epa" />
			==See also==
	{{clear}}
			*] – a derivative of acetonitrile used to ] ], and also used as a reagent in the ]
	==References==		==References==
	{{reflist|colwidth=35em}}		{{reflist|30em}}
	==External links==		==External links==
	*		*
	*		*
	*		*
	*		*
			* , Office of Pollution Prevention and Toxics, U.S. Environmental Protection Agency
			*
			* , on: SciTechDaily. September 10, 2020. Source: Tokyo University of Science: Acetonitrile found in molecular cloud ] at the center of ].
			{{Molecules detected in outer space}}
			{{Authority control}}
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