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Revision as of 20:03, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470564223 of page Acrylonitrile for the Chem/Drugbox validation project (updated: '').		Latest revision as of 01:05, 17 December 2024 edit Arthurfragoso (talk | contribs)Extended confirmed users2,076 edits Fixes images on dark mode
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			{{Short description|1=Organic compound (CH2=CH−C≡N)}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{Chembox
	| Watchedfields = changed		|Watchedfields = changed
	| verifiedrevid = 443368571		|verifiedrevid = 477241395
	| ImageFileL1_Ref = {{chemboximage|correct|??}}		|ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageFileL1 = Acrylonitrile-2D.png		|ImageFileL1 = Structural formula of acrylonitrile.svg
			|ImageClassL1 = skin-invert
	| ImageSizeL1 = 120 px
	| ImageFileR1_Ref = {{chemboximage|correct|??}}		|ImageFileR1_Ref = {{chemboximage|correct|??}}
	| ImageFileR1 = Acrylonitrile-2D-skeletal.png		|ImageFileR1 = Acrylonitrile-2D-skeletal.svg
			|ImageClassR1 = skin-invert
	| ImageSizeR1 = 120 px
	| ImageFileL2 = Acrylonitrile-3D-balls.png		|ImageFileL2 = Acrylonitrile-3D-balls.png
			|ImageFileR2 = Acrylonitrile-3D-vdW.png
	| ImageSizeL2 = 120 px
			|PIN = Prop-2-enenitrile
	| ImageFileR2 = Acrylonitrile-3D-vdW.png
			|OtherNames = Acrylonitrile<br />2-Propenenitrile<br />Cyanoethene<br />] ] (VCN)<br />Cyanoethylene<ref name=NIOSH/><br />Propenenitrile<ref name=NIOSH/><br />Vinyl nitrile
	| ImageSizeR2 = 120 px
			|Section1 = {{Chembox Identifiers
	| IUPACName = 2-propenenitrile
			|InChIKey = NLHHRLWOUZZQLW-UHFFFAOYAG
	| OtherNames = cyanoethene,<br/>]]
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| Section1 = {{Chembox Identifiers
			|ChEMBL = 445612
	| Abbreviations =
			|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| InChIKey = NLHHRLWOUZZQLW-UHFFFAOYAG
			|StdInChI = 1S/C3H3N/c1-2-3-4/h2H,1H2
	| SMILES1 = C=CC#N
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChIKey = NLHHRLWOUZZQLW-UHFFFAOYSA-N
	| ChEMBL = 445612
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		|CASNo_Ref = {{cascite|correct|CAS}}
			|CASNo = 107-13-1
	| StdInChI = 1S/C3H3N/c1-2-3-4/h2H,1H2
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|ChemSpiderID=7567
	| StdInChIKey = NLHHRLWOUZZQLW-UHFFFAOYSA-N
			|PubChem = 7855
	| CASNo_Ref = {{cascite|correct|CAS}}
			|UNII_Ref = {{fdacite|correct|FDA}}
	| CASNo = 107-13-1
			|UNII = MP1U0D42PE
	| EINECS =
			|SMILES = N#CC=C
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|InChI = 1/C3H3N/c1-2-3-4/h2H,1H2
	| ChemSpiderID=7567
			|ChEBI_Ref = {{ebicite|correct|EBI}}
	| EINECSCASNO =
	| PubChem = 7855		|ChEBI = 28217
	| UNII_Ref = {{fdacite|correct|FDA}}		|KEGG_Ref = {{keggcite|correct|kegg}}
	| UNII = MP1U0D42PE		|KEGG = C01998
	| SMILES = N#CC=C		|UNNumber = 1093
			|EC_number = 608-003-00-4
	| InChI = 1/C3H3N/c1-2-3-4/h2H,1H2
	| RTECS =		|RTECS = AT5250000
	| MeSHName =
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 28217
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C01998
	| ATCCode_prefix =
	| ATCCode_suffix =
	| ATC_Supplemental =}}
	| Section2 = {{Chembox Properties
	|C=3|H=3|N=1
	| Appearance = Colourless liquid
	| Density = 0.81 g/cm<sup>3</sup>
	| MeltingPt = -84 °C(189 ])
	| Melting_notes =
	| BoilingPt = 77 °C (350 ])
	| Boiling_notes =
	| Solubility = 7 g/100 ] at 20 °C
	| SolubleOther =
	| Solvent = ], ],<br/>]
	| LogP =
	| VaporPressure =
	| HenryConstant =
	| AtmosphericOHRateConstant =
	| pKa =
	| pKb = }}
	| Section3 = {{Chembox Structure
	| CrystalStruct =
	| Coordination =
	| MolShape = }}
	| Section4 = {{Chembox Thermochemistry
	| DeltaHf =
	| DeltaHc =
	| Entropy =
	| HeatCapacity = }}
	| Section5 = {{Chembox Pharmacology
	| AdminRoutes =
	| Bioavail =
	| Metabolism =
	| HalfLife =
	| ProteinBound =
	| Excretion =
	| Legal_status =
	| Legal_US =
	| Legal_UK =
	| Legal_AU =
	| Legal_CA =
	| PregCat =
	| PregCat_AU =
	| PregCat_US = }}
	| Section6 = {{Chembox Explosive
	| ShockSens =
	| FrictionSens =
	| ExplosiveV =
	| REFactor = }}
	| Section7 = {{Chembox Hazards
	| ExternalMSDS =
	| EUClass =
	| EUIndex =
	| MainHazards = ],<br/>reactive,<br/> toxic
	| NFPA-H = 4
	| NFPA-F = 3
	| NFPA-R = 2
	| NFPA-O =
	| RPhrases =
	| SPhrases =
	| RSPhrases =
	| FlashPt =
	| Autoignition =
	| ExploLimits =
	| PEL = }}
	| Section8 = {{Chembox Related
	| OtherAnions =
	| OtherCations =
	| OtherFunctn =
	| Function =
	| OtherCpds = ],<br/>]}}
	}}		}}
			|Section2 = {{Chembox Properties
			|C=3 | H=3 | N=1
			|Appearance = Colourless liquid
			|Density = 0.81 g/cm<sup>3</sup>
			|MeltingPtC = -84
			|BoilingPtC = 77
			|Solubility = 70 g/L
			|Solvent = ]<br>]<br/>]
			|VaporPressure = 83 mmHg<ref name=NIOSH/>
			|LogP = 0.19<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/107-13-1_1186893.html|title=Acrylonitrile_msds}}</ref> }}
			|Section3 = {{Chembox Hazards
			|ExternalSDS =
			|MainHazards = ]<br/>reactive<br/> toxic<br/> potential occupational carcinogen<ref name=NIOSH/>
			|NFPA-H = 4
			|NFPA-F = 3
			|NFPA-R = 2
			|FlashPtF= 30<ref name=NIOSH/>
			|AutoignitionPtC = 471
			|ExploLimits = 3–17%
			|PEL = TWA 2 ppm C 10 ppm <ref name=NIOSH>{{PGCH|0014}}</ref>
			|REL = Ca TWA 1 ppm C 10 ppm <ref name=NIOSH/>
			|IDLH = 85 ppm<ref name=NIOSH/>
			|LC50 = 500 ppm (rat, 4 h)<br/>313 ppm (mouse, 4 h)<br/>425 ppm (rat, 4 h)<ref name=IDLH>{{IDLH|107131|Acrylonitrile}}</ref>
			|LCLo = 260 ppm (rabbit, 4 h)<br/>575 ppm (guinea pig, 4 h)<br/>636 ppm (rat, 4 h)<br/>452 ppm (human, 1 h)<ref name=IDLH/>
			}}
			|Section4 = {{Chembox Related
			|OtherFunction = ]<br/>]
			|OtherFunction_label = ]s
			|OtherCompounds = ]<br/>]}}
			}}
			'''Acrylonitrile''' is an ] with the ] {{chem2|CH2CHCN}} and the ] {{chem2|H2C\dCH\sC\tN}}. It is a colorless, ] liquid. It has a pungent odor of garlic or onions.<ref name="atsdr">{{Cite web |title=Medical Management Guidelines for Acrylonitrile |url=https://www.atsdr.cdc.gov/mmg/mmg.asp?id=443&tid=78 |access-date=2020-06-10 |publisher=Agency for Toxic Substances & Disease Registry}}</ref> Its ] consists of a ] ({{chem2|\sCH\dCH2}}) linked to a ] ({{chem2|\sC\tN}}). It is an important ] for the manufacture of useful ]s such as ]. It is ] and ] at low doses.<ref name = ullmann/>
			Acrylonitrile is one of the components of ABS plastic (]).<ref>{{Citation |last=Campo |first=E. Alfredo |title=1 - Polymeric Materials and Properties |date=2008-01-01 |url=https://www.sciencedirect.com/science/article/pii/B9780815515517500036 |work=Selection of Polymeric Materials |pages=1–39 |editor-last=Campo |editor-first=E. Alfredo |access-date=2023-11-20 |series=Plastics Design Library |place=Norwich, NY |publisher=William Andrew Publishing |doi=10.1016/b978-081551551-7.50003-6 |isbn=978-0-8155-1551-7}}</ref>
			==Structure and basic properties==
			Acrylonitrile is an ] with the ] {{chem2|CH2CHCN}} and the ] {{chem2|H2C\dCH\sC\tN}}. It is a colorless, ] liquid although commercial samples can be yellow due to ]. It has a pungent odor of garlic or onions.<ref name="atsdr"/> Its ] consists of a ] ({{chem2|\sCH\dCH2}}) linked to a ] ({{chem2|\sC\tN}}). It is an important ] for the manufacture of useful ]s such as ]. It is ] and ] at low doses.<ref name = ullmann/>
			==Production==
			Acrylonitrile was first synthesized by the French chemist ] in 1893.<ref>
			* {{cite journal|first=C. |last=Moureu |date=1893 |url=http://babel.hathitrust.org/cgi/pt?id=uc1.31822017842394;view=1up;seq=149 |title=Contribution à l'étude de l'acide acrylique et de ses dérivés |trans-title=Contribution to the study of acrylic acid and of its derivatives |journal=Annales de chimie et de physique |series=7th |volume=2 |pages=145–212}} See especially pp. 187–189 ("Nitrile acrylique ou cyanure de vinyle (Propène-nitrile)").
			* {{cite journal|first=C. |last=Moureu |date=1893 |url=http://gallica.bnf.fr/ark:/12148/bpt6k282008w/f436.image.r=BulletindelaSocieteChimiquedeParis.langFR |title=Nitrile acrylique, cyanure de vinyle (propène-nitrile)|trans-title=Acrylic nitrile, vinyl cyanide (propenenitrile) |journal=Bulletin de la Société Chimique de France |series=3rd |volume=9 |pages=424–427}}</ref> Acrylonitrile is produced by ] ] of ], also known as the ] process. In 2002, world production capacity was estimated at 5&nbsp;million tonnes per year,<ref name = ullmann>{{Ullmann | title = Acrylonitrile | first= James F. |last=Brazdil | doi = 10.1002/14356007.a01_177.pub3}}</ref><ref>{{cite web|publisher=American Chemical Society National Historic Chemical Landmarks |title=The Sohio Acrylonitrile Process |url=http://portal.acs.org/portal/PublicWebSite/education/whatischemistry/landmarks/acrylonitrile/index.htm |archive-url=https://archive.today/20130223214113/http://portal.acs.org/portal/PublicWebSite/education/whatischemistry/landmarks/acrylonitrile/index.htm |url-status=dead |archive-date=2013-02-23 |access-date=2013-05-13 }}</ref> rising to about 6&nbsp;million tonnes by 2017.<ref name=sweet>{{cite journal |last1=Davey |first1=Stephen G. |title=Sustainability: Sweet new route to acrylonitrile |journal=Nature Reviews Chemistry |date=January 2018 |volume=2 |issue=1 |pages=0110 |doi=10.1038/s41570-017-0110|doi-access=free }}</ref> ] and ] are significant byproducts that are recovered for sale.<ref name = ullmann/> In fact, the ] was caused by a decrease in demand for acrylonitrile.<ref>{{cite journal | first= A.|last= 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>
			:{{chem2|2 CH3\sCH\dCH2 + 2 NH3 + 3 O2 -> 2 CH2\dCH\sC\tN + 6 H2O}}
			In the SOHIO process, ], ], and air (oxidizer) are passed through a ] containing the catalyst at 400–510&nbsp;°C and 50–200&nbsp;kPa<sub>g</sub>. 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, ], and ] (from excess ammonia). A recovery column removes bulk water, and acrylonitrile and acetonitrile are separated by distillation. One of the first useful catalysts was ] ] ({{chem2|Bi9PMo12O52}}) ] on silica.<ref>{{Cite journal|last=Grasselli|first=Robert K.|date=2014|title=Site isolation and phase cooperation: Two important concepts in selective oxidation catalysis: A retrospective|journal=Catalysis Today|language=en|volume=238|pages=10–27|doi=10.1016/j.cattod.2014.05.036}}</ref> Further improvements have since been made.<ref name = ullmann/>
			===Alternative routes===
			Various ] routes to acrylonitrile are being explored from renewable feedstocks, such as ], ] (from ] production), or ] (which can itself be produced from renewable feedstocks). The lignocellulosic route involves fermentation of the biomass to ] and ], which are then converted to acrylonitrile by dehydration and ].<ref name="GrasselliTrifirò2016">{{cite journal|last1=Grasselli|first1=Robert K.|last2=Trifirò|first2=Ferruccio|s2cid=99550463|title=Acrylonitrile from Biomass: Still Far from Being a Sustainable Process|journal=Topics in Catalysis|volume=59|issue=17–18|year=2016|pages=1651–1658|issn=1022-5528|doi=10.1007/s11244-016-0679-7}}</ref><ref name=sweet /> The glycerol route begins with its ] to ], which undergoes ammoxidation to give acrylonitrile.<ref name="Guerrero-PérezBañares2015">{{cite journal|last1=Guerrero-Pérez|first1=M. Olga|last2=Bañares|first2=Miguel A.|title=Metrics of acrylonitrile: From biomass vs. petrochemical route|journal=Catalysis Today|volume=239|year=2015|pages=25–30|issn=0920-5861|doi=10.1016/j.cattod.2013.12.046}}</ref> The glutamic acid route employs ] to 3-cyanopropanoic acid, followed by a decarbonylation-elimination to acrylonitrile.<ref name="Le NôtreScott2011">{{cite journal|last1=Le Nôtre|first1=Jérôme|last2=Scott|first2=Elinor L.|last3=Franssen|first3=Maurice C. R.|last4=Sanders|first4=Johan P. M.|title=Biobased synthesis of acrylonitrile from glutamic acid|journal=Green Chemistry|volume=13|issue=4|year=2011|pages=807|issn=1463-9262|doi=10.1039/c0gc00805b}}</ref> Of these, the glycerol route is broadly considered to be the most viable, although none of these green methods are commercially competitive.<ref name="GrasselliTrifirò2016" /><ref name="Guerrero-PérezBañares2015"/>
			==Uses==
			Acrylonitrile is used principally as a ] to prepare ], a ], or several important ]s, such as ] (SAN), ] (ABS), ] (ASA), and other ]s such as ] (NBR). ] of acrylonitrile<ref>{{cite book |last1=Ellis |first1=Paul G |title=A radiation-chemical study of the hydrodimerisation of acrylonitrile |date=1972 |publisher=Leeds University, Ph D thesis |location=UK}}</ref><ref>{{cite journal |last1=Buxton |first1=George V. |last2=Ellis |first2=Paul G. |last3=McKillop |first3=Thomas F.W. |title=Pulse radiolysis study of acrylonitrile in aqueous solution |journal=J. Chem. Soc., Faraday Trans. 1 |date=1979 |volume=75 |page=1050|doi=10.1039/f19797501050 }}</ref> affords ], used in the synthesis of certain ]s:
			:{{chem2|2 CH2\dCHCN + 2 e- + 2 H+ -> NCCH2\sCH2\sCH2\sCH2CN}}
			Acrylonitrile is also a precursor in the manufacture of ] and ].<ref name = ullmann/>
			===Synthesis of chemicals===
			Hydrogenation of acrylonitrile is one route to propionitrile. Hydrolysis with sulfuric acid gives acrylamide sulfate, {{chem2|CH\dCHC(O)NH2*H2SO4}}. This salt can be converted to ] with treatment with base or to ] by treatment with ].<ref name = ullmann/>
			The reaction of acrylonitrile with protic nucleophiles is a common route to a variety of specialty chemicals. The process is called ]:
			:{{chem2|YH + H2C\dCHCN -> Y\sCH2\sCH2CN}}
			Typical protic nucleophiles are ]s, ]s, and especially ]s.<ref name=UllmannAmine>{{Ullmann|doi=10.1002/14356007.a02_001|title=Amines, Aliphatic|year=2000|last1= Eller|first1=Karsten|last2=Henkes|first2=Erhard|last3=Rossbacher|first3=Roland|last4=Höke|first4=Hartmut|isbn=3527306730}}</ref>
			Acrylonitrile and derivatives, such as 2-chloroacrylonitrile, are ]s in ]s.
			==Health effects==
			Acrylonitrile is moderately ] with ] = 81 mg/kg (rats). It undergoes ] ]. The burning material releases fumes of ] and ]. It is classified as a ] (carcinogenic) by the ] (IARC),<ref name=":1">. The Lancet, Volume 25, Issue 8 (2024)</ref> and workers exposed to high levels of airborne acrylonitrile are diagnosed more frequently with ] than the rest of the population.<ref>. epa.gov</ref> Acrylonitrile is one of seven ]s in ] smoke that are most associated with ] ].<ref>Cunningham FH, Fiebelkorn S, Johnson M, Meredith C. A novel application of the Margin of Exposure approach: segregation of tobacco smoke toxicants. Food Chem Toxicol. 2011 Nov;49(11):2921-33. doi: 10.1016/j.fct.2011.07.019. Epub 2011 Jul 23. {{PMID|21802474}}</ref> The mechanism of action of acrylonitrile appears to involve oxidative stress and oxidative DNA damage.<ref>Pu X, Kamendulis LM, Klaunig JE. Acrylonitrile-induced oxidative stress and oxidative DNA damage in male Sprague-Dawley rats. Toxicol Sci. 2009;111(1):64-71. doi:10.1093/toxsci/kfp133</ref> Acrylonitrile increases cancer in high dose tests in male and female rats and mice<ref>.</ref> and induces ] in human umbilical cord ].<ref name="pmid = 24248151">{{cite journal | last= Sun|first= X. | title = Cytotoxic effects of acrylonitrile on human umbilical cord mesenchymal stem cells in vitro | journal = Molecular Medicine Reports | volume = 9 | issue = 1|date=January 2014 | pmid = 24248151 | url = http://www.spandidos-publications.com/mmr/9/1/97 | pages = 97–102 | doi=10.3892/mmr.2013.1802| doi-access = free }}</ref>
			It evaporates quickly at room temperature (20&nbsp;°C) to reach dangerous concentrations; ], respiratory irritation, and eye irritation are the immediate effects of this exposure.<ref name=":0">{{Cite web|title = CDC – Acrylonitrile – International Chemical Safety Cards |publisher=NIOSH|url = https://www.cdc.gov/niosh/ipcsneng/neng0092.html|website = www.cdc.gov|access-date = 2015-07-31}}</ref> Pathways of exposure for humans include ], ], and ] that can expose the human subject directly if they inhale or smoke. Routes of exposure include inhalation, oral, and to a certain extent dermal uptake (tested with volunteer humans and in rat studies).<ref name="EPAfacts">. epa.gov</ref> Repeated exposure causes skin sensitization and may cause central nervous system and ].<ref name=":0"/>
			There are two main excretion processes of acrylonitrile. The primary method is excretion in urine when acrylonitrile is metabolized by being directly conjugated to ]. The other method is when acrylonitrile is enzymatically converted into 2-cyanoethylene oxide which will produce ] end products that ultimately form ], which is excreted via urine.<ref name="EPAfacts" /> Exposure can thus be detected via blood draws and urine sampling.<ref name=":1"/>
			In July 2024, the ] upgraded acrylonitrile's classification from 'possibly carcinogenic' to ] for humans. The Agency found ] linking it to ].<ref>{{cite news |last1= |first1= |title=WHO agency says talc is ‘probably’ cancer-causing|url=https://globalnation.inquirer.net/241682/who-agency-says-talc-is-probably-cancer-causing |accessdate=July 7, 2024 |publisher= ]|date=July 6, 2024}}</ref><ref>{{Cite journal |last=Stayner |first=Leslie T |last2=Carreón-Valencia |first2=Tania |last3=Demers |first3=Paul A |last4=Fritz |first4=Jason M |last5=Sim |first5=Malcolm R |last6=Stewart |first6=Patricia |last7=Tsuda |first7=Hiroyuki |last8=Cardenas |first8=Andres |last9=Consonni |first9=Dario |last10=Davies |first10=Laurie |last11=De Matteis |first11=Sara |last12=Felley-Bosco |first12=Emanuela |last13=Ghio |first13=Andrew J |last14=Göen |first14=Thomas |last15=Grosse |first15=Yann |date=July 5, 2024 |title=Carcinogenicity of talc and acrylonitrile |url=https://doi.org/10.1016/S1470-2045(24)00384-X |journal=The Lancet Oncology |doi=10.1016/s1470-2045(24)00384-x |issn=1470-2045}}</ref>
			===Use in plastic bottles===
			In June 1974 ] introduced the acrylonitrile/styrene 32oz Easy‐Goer plastic bottle, offering energy savings during manufacture, increased durability, and weight savings over glass.<ref>{{Cite web |date=1977-03-01 |title=Polyester Held a Winner Over Acrylonitrile in War About Soft‐Drink Bottles |url=https://www.nytimes.com/1977/03/01/archives/polyester-held-a-winner-over-acrylonitrile-in-war-about-softdrink.html |access-date=2024-11-26 |publisher=The New York Times }}</ref> In March 1977 after a suit filed by the ] the FDA rescinded approval of acrylonitrile bottles citing adverse effects on test animals.<ref>{{Cite web |date=1977-02-23 |title=Cancer Experts Warn of Dangers in Some Plastic Wrap Chemicals |url=https://www.nytimes.com/1977/02/23/archives/cancer-experts-warn-of-dangers-in-some-plastic-wrap-chemicals.html |access-date=2024-11-26 |publisher=The New York Times }}</ref> ], Coca-Cola's bottle manufacturer refuted the decision, stating “repeated tests have demonstrated that there is no detectable migration of acrylonitrile into the bottle's content.” After several appeals in court by September 1977 the FDA finalized their ban.<ref>{{Cite web |date=1977-03-08 |title=Plastic Beverage Bottles Made From Acrylonitrile Are Banned by the F.D.A.|url=https://www.nytimes.com/1977/03/08/archives/plastic-beverage-bottles-made-from-acrylonitrile-are-banned-by-the.html |access-date=2024-11-26 |publisher=The New York Times }}</ref><ref>{{cite journal | title = MONSANTO LOSES PLASTIC BOTTLE FIGHT | journal = Chemical & Engineering News | volume = 55 | issue = 39|date=1977-09-26 | url = https://pubs.acs.org/doi/pdf/10.1021/cen-v055n039.p006 | pages = 6 | doi=10.1021/cen-v055n039.p006 }}</ref>
			===Incidents===
			A large amount of acrylonitrile (approximately 6500 tons) leaked from an industrial polymer plant owned by ] after the violent ] in Turkey. Over 5000 people were affected and the exposed animals had died.<ref name=ttb>{{cite web |url= https://www.ttb.org.tr/msg/dergi/ocak01/9.htm|title= ENDÜSTRİYEL BİR ÇEVRE FELAKETİ: AKRİLONİTRİL|trans-title= AN INDUSTRIAL ENVIRONMENT DISASTER: ACRYLONITRILE|author=Nadi Bakırcı|date= 2001|website= |publisher= ] |access-date=}}</ref> The leak was only noticed by the company 8 hours after the incident. Healthcare workers did not know about the health effects of acrylonitrile and tried to treat the victims with painkillers and IV fluids.<ref name=tabella>{{cite web |url= https://tabella.org/2020/11/30/17-agustos-1999-depremi-akrilonitril-zehirlenmesi/|title= 17 Ağustos 1999 Depremi: Akrilonitril Zehirlenmesi|trans-title= 17 August 1999 Earthquake: Acrylonitrile Poisoning|author=Fatma Dalokay |date= 30 November 2020|website= Tabella|publisher= |access-date= |quote=}}</ref> One lawyer, Ayşe Akdemir, sued the company with 44 families as the plaintiffs.<ref name=tabella/> Aksa Akrilik was sued by 200 residents who were affected by acrylonitrile.<ref name=bigpara>{{cite web |url= https://mbigpara.hurriyet.com.tr/amp/haberler/iso-nun-sasirtan-cevre-odulu-aksa-nin/525904/|title=İSO'nun şaşırtan çevre ödülü Aksa'nın |author=<!--Not stated--> |date=26 June 2005 |website=] |publisher= |access-date= |quote=}}</ref> An increase in cancer cases in the area was confirmed by the ],<ref name=bigpara/> as the cancer rate in the affected area has increased by 80%, from 1999 to April 2002.<ref name=tabella/> In 2003, the owner of Aksa Akrilik died from lung cancer related to acrylonitrile exposure.<ref name=tabella/> As of 2001, this is the largest known acrylonitrile leak.<ref name=ttb/>
			== Occurrence ==
			Acrylonitrile is not naturally formed on Earth. It has been detected at the sub-ppm level at industrial sites. It persists in the air for up to a week. It decomposes by reacting with oxygen and hydroxyl radical to form ] and ].<ref>{{cite journal|last1=Grosjean|first1=Daniel|title=Atmospheric Chemistry of Toxic Contaminants. 3. Unsaturated Aliphatics: Acrolein, Acrylonitrile, Maleic Anhydride|journal=Journal of the Air & Waste Management Association|date=December 1990|volume=40|issue=12|pages=1664–1669|doi=10.1080/10473289.1990.10466814|bibcode=1990JAWMA..40.1664G }}</ref> Acrylonitrile is ].<ref name=":0"/> Acrylonitrile has been detected in the atmosphere of ], a moon of ].<ref name="SP-20170728"/><ref name="SA-20170728"/><ref name="WP-20170808">{{cite news |last=Kaplan |first=Sarah |title=This weird moon of Saturn has some essential ingredients for life |url=https://www.washingtonpost.com/news/speaking-of-science/wp/2017/08/08/this-weird-moon-of-saturn-has-some-essential-ingredients-for-life/ |date=8 August 2017 |newspaper=] |access-date=8 August 2017 }}</ref> Computer simulations suggest that on Titan conditions exist such that the compound could form structures similar to ]s and ] on Earth, called ]<ref name="SP-20170728">{{cite web |last=Wall |first=Mike |title=Saturn Moon Titan Has Molecules That Could Help Make Cell Membranes |url=https://www.space.com/37653-saturn-moon-titan-cell-membrane-molecules.html |date=28 July 2017 |work=] |access-date=29 July 2017 }}</ref><ref name="SA-20170728">{{cite journal |last=Palmer |first=Maureen Y.|display-authors=et al |title=ALMA detection and astrobiological potential of vinyl cyanide on Titan |date=28 July 2017 |journal=] |volume =3 |pages=e1700022|number=7 |doi= 10.1126/sciadv.1700022 |pmid=28782019|pmc=5533535 |bibcode=2017SciA....3E0022P}}</ref>
			{{Clear}}
			== References ==
			{{reflist}}
			==External links==
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			* {{Webarchive|url=https://web.archive.org/web/20120903053051/http://potency.berkeley.edu/MOE.html |date=2012-09-03 }}
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			{{Molecules detected in outer space}}
			{{Authority control}}
			]
			]
			]
			]
			]
			]
			]
			]