Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Acrolein: Difference between pages

{{Distinguish|Propanol|Acyloin|Propanal}}

{{Chembox

|Watchedfields = changed

|verifiedrevid = 477241293

|Name = Acrolein

|ImageFileL1_Ref = {{chemboximage|correct|??}}

|ImageFileL1 = Acrolein-s-trans-2D-w.png

|ImageFileR1 = Acrolein-s-trans-2D-skeletal.png

|ImageFileL2 = Acrolein-s-trans-GED-MW-3D-bs-17.png

|ImageFileR2 = Acrolein-s-trans-GED-MW-3D-sf.png

|ImageSizeR2 = 120px

|ImageName = Acrolein

|PIN = Prop-2-enal

|OtherNames = Acraldehyde<ref name=NIOSH/><br />Acrylic aldehyde<ref name=NIOSH/><br />Allyl aldehyde<ref name=NIOSH/><br />Ethylene aldehyde<br /> Acrylaldehyde<ref name=NIOSH/>

|Section1={{Chembox Identifiers

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 15368

|SMILES = O=CC=C

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 7864XYD3JJ

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = C01471

|InChI = 1/C3H4O/c1-2-3-4/h2-3H,1H2

|InChIKey = HGINCPLSRVDWNT-UHFFFAOYAQ

|PubChem = 7847

|IUPHAR_ligand = 2418

|EC_number = 203-453-4

|RTECS = AS1050000

|UNNumber = 1092

|SMILES1 = C=CC=O

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 721

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C3H4O/c1-2-3-4/h2-3H,1H2

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = HGINCPLSRVDWNT-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 107-02-8

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 7559

}}

|Section2={{Chembox Properties

|C=3 | H=4 | O=1

|Appearance = Colorless to yellow liquid. Colorless gas in smoke.

|Odor = Acrid, Foul, Irritating

|Solubility = Appreciable (> 10%)

|MeltingPtC = −88

|BoilingPtC = 53

|Density = 0.839 g/mL

|VaporPressure = 210 mmHg<ref name=NIOSH/>

}}

|Section3={{Chembox Hazards

|ExternalSDS = [https://www.sigmaaldrich.com/GB/en/sds/aldrich/110221 Sigma-Aldrich SDS]

|MainHazards = Highly poisonous. Causes severe irritation to exposed membranes. Extremely flammable liquid and vapor.

|NFPA-H = 4

|NFPA-R = 3

|NFPA-F = 3

|FlashPtC = −26

|AutoignitionPtC = 278

|ExploLimits = 2.8-31%<ref name=NIOSH/>

|PEL = TWA 0.1 ppm (0.25 mg/m³)<ref name=NIOSH>{{PGCH|0011}}</ref>

|REL = TWA 0.1 ppm (0.25 mg/m³) ST 0.3 ppm (0.8 mg/m³)<ref name=NIOSH/>

|IDLH = 2 ppm<ref name=NIOSH/>

|LC50 = 875 ppm (mouse, 1 min)<br />175 ppm (mouse, 10 min)<br />150 ppm (dog, 30 min)<br />8 ppm (rat, 4 hr)<br />375 ppm (rat, 10 min)<br />25.4 ppm (hamster, 4 hr)<br />131 ppm (rat, 30 min)<ref name=IDLH>{{IDLH|107028|Acrolein}}</ref>

|LCLo = 674 ppm (cat, 2 hr)<ref name=IDLH/>

|Hazards_ref=<ref>{{cite web|url=http://www.nmsu.edu/safety/programs/chem_safety/NFPA-ratingA-C.htm |title=Archived copy |access-date=2015-03-26 |url-status=dead |archive-url=https://web.archive.org/web/20150402091414/http://www.nmsu.edu/safety/programs/chem_safety/NFPA-ratingA-C.htm |archive-date=2015-04-02 }}</ref>

|GHSPictograms = {{GHS02}} {{GHS05}} {{GHS06}} {{GHS08}} {{GHS09}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|225|300|311|314|330|410}}

|PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|270|271|273|280|284|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|320|321|322|330|361|363|370+378|391|403+233|403+235|405|501}}

}}

|Section4={{Chembox Related

|OtherFunction_label = alkenals

|OtherFunction = [[Crotonaldehyde]]<br />

'''Acrolein''' (systematic name: '''propenal''') is the simplest [[Alpha-beta Unsaturated carbonyl compounds|unsaturated aldehyde]]. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when [[cooking oil]] is heated to its [[smoke point]]) is caused by [[glycerol]] in the burning fat breaking down into acrolein. It is produced industrially from [[propene]] and mainly used as a [[biocide]] and a building block to other chemical compounds, such as the [[amino acid]] [[methionine]].

==History==

Acrolein was first named and characterized as an aldehyde by the Swedish chemist [[Jöns Jacob Berzelius]] in 1839. He had been working with it as a thermal degradation product of [[glycerol]], a material used in the manufacture of soap. The name is a contraction of 'acrid' (referring to its pungent smell) and 'oleum' (referring to its oil-like consistency). In the 20th century, acrolein became an important intermediate for the industrial production of [[acrylic acid]] and acrylic plastics.<ref>Jan F. Stevens and Claudia S. Maier, "Acrolein: Sources, metabolism, and biomolecular interactions relevant to human health and disease", ''Mol Nutr Food Res.'' 2008 Jan; 52(1): 7–25.</ref>

==Production==

Acrolein is prepared industrially by oxidation of [[propene]]. The process uses air as the source of oxygen and requires [[metal oxide]]s as [[heterogeneous catalyst]]s:<ref name=Ullmann>{{Ullmann|author1=Dietrich Arntz |author2=Achim Fischer |author3=Mathias Höpp |author4=Sylvia Jacobi |author5=Jörg Sauer |author6=Takashi Ohara |author7=Takahisa Sato |author8=Noboru Shimizu |author9=Helmut Schwind |display-authors=3 |title=Acrolein and Methacrolein||year=2012|doi=10.1002/14356007.a01_149.pub2}}</ref>

:{{chem2|CH3CH\dCH2 + O2 → CH2\dCHCHO + H2O}}

About 500,000 tons of acrolein are produced in this way annually in North America, Europe, and Japan. Additionally, all [[acrylic acid]] is produced via the transient formation of acrolein.

[[Propane]] represents a promising but challenging feedstock for the synthesis of acrolein (and acrylic acid).The main challenge is in fact the overoxidation to this acid.

When [[glycerol]] (also called glycerin) is heated to 280&nbsp;°C, it decomposes into acrolein:

:(CH₂OH)₂CHOH → CH₂=CHCHO + 2 H₂O

This route is attractive when glycerol is co-generated in the production of biodiesel from vegetable oils or animal fats. The dehydration of glycerol has been demonstrated but has not proven competitive with the route from [[petrochemical]]s.<ref>{{cite journal | last1 = Martin | first1 = Andreas | last2 = Armbruster | first2 = Udo | last3 = Atia | first3 = Hanan | year = 2012 | title = Recent developments in dehydration of glycerol toward acrolein over heteropolyacids | journal = European Journal of Lipid Science and Technology | volume = 114 | issue = 1| pages = 10–23 | doi = 10.1002/ejlt.201100047 }}</ref><ref>{{Cite journal |last1=Abdullah |first1=Anas |last2=Zuhairi Abdullah |first2=Ahmad |last3=Ahmed |first3=Mukhtar |last4=Khan |first4=Junaid |last5=Shahadat |first5=Mohammad |last6=Umar |first6=Khalid |last7=Alim |first7=Md Abdul |date=March 2022 |title=A review on recent developments and progress in sustainable acrolein production through catalytic dehydration of bio-renewable glycerol |url=https://linkinghub.elsevier.com/retrieve/pii/S0959652622005145 |journal=Journal of Cleaner Production |language=en |volume=341 |pages=130876 |doi=10.1016/j.jclepro.2022.130876|bibcode=2022JCPro.34130876A |s2cid=246853148|url-access=subscription }}</ref>

===Niche or laboratory methods===

The original industrial route to acrolein, developed by Degussa, involves condensation of [[formaldehyde]] and [[acetaldehyde]]:

:HCHO + CH₃CHO → CH₂=CHCHO + H₂O

Acrolein may also be produced on lab scale by the action of [[potassium bisulfate]] on glycerol (glycerine).<ref>{{OrgSynth | author1 = Homer Adkins | authorlink1 = Homer Burton Adkins | author2 = W. H. Hartung | title = Acrolein | collvol = 1 | collvolpages = 15 | year = 1926 | volume = 6 | pages = 1 | doi = 10.15227/orgsyn.006.0001 | prep = cv1p0015}}</ref>

==Reactions==

Acrolein is a relatively [[Electrophile|electrophilic]] compound and a reactive one, hence its high toxicity. It is a good [[Michael acceptor]], hence its useful reaction with thiols. It forms [[acetal]]s readily, a prominent one being the [[spirocycle]] derived from [[pentaerythritol]], diallylidene pentaerythritol. Acrolein participates in many [[Diels-Alder reaction]]s, even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including [[myrac aldehyde|myrac aldehyde ("lyral")]] and [[norbornene]]-2-carboxaldehyde.<ref name=Ullmann/> The monomer [[3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate]] is also produced from acrolein via the intermediacy of [[tetrahydrobenzaldehyde]].

==Uses==

===Military uses===

Acrolein was used in warfare due to its irritant and blistering properties. The French used the chemical in their hand grenades and artillery shells<ref>{{cite book |last1=Prentiss |first1=Augustin Mitchell |last2=Fisher |first2=George J. B. |title=Chemicals in War: A Treatise on Chemical Warfare |date=1937 |publisher=McGraw-Hill Book Company, Incorporated |page=139 |url=https://books.google.com/books?id=5zdLAAAAMAAJ |access-date=21 November 2021 |language=en}}</ref> during [[World War I]] under the name "Papite".<ref>{{cite book |last1=Eisler |first1=Ronald |title=Acrolein Hazards to Fish, Wildlife, and Invertebrates: A Synoptic Review |date=1994 |publisher=U.S. Department of the Interior, National Biological Survey |url=https://books.google.com/books?id=sijZELAuYAEC&pg=PA4 |access-date=21 November 2021 |language=en}}</ref>

===Biocide===

Acrolein is mainly used as a [[contact herbicide]] to control submersed and floating weeds, as well as algae, in [[irrigation canal]]s. It is used at a level of 10 ppm in irrigation and recirculating waters. In the [[oil and gas industry]], it is used as a [[biocide]] in [[drilling water]]s, as well as a scavenger for [[hydrogen sulfide]] and [[thiol|mercaptans]].<ref name=Ullmann/>

===Chemical precursor===

A number of useful compounds are made from acrolein, exploiting its bifunctionality. The amino acid [[methionine]] is produced by addition of [[methanethiol]] followed by the [[Strecker synthesis]]. Acrolein condenses with acetaldehyde and amines to give [[methylpyridine]]s.<ref name=ul>{{Ullmann|first1=S. |last1=Shimizu |first2=N. |last2=Watanabe |first3=T. |last3=Kataoka |first4=T. |last4=Shoji |first5=N. |last5=Abe |first6=S. |last6=Morishita |first7=H. |last7=Ichimura |title=Pyridine and Pyridine Derivatives |doi=10.1002/14356007.a22_399}}</ref> It is also an intermediate in the [[Skraup reaction|Skraup synthesis]] of [[quinoline]]s.

Acrolein will polymerize in the presence of oxygen and in water at concentrations above 22%. The color and texture of the polymer depends on the conditions. The polymer is a clear, yellow solid. In water, it will form a hard, porous plastic.{{citation needed|date=March 2020}}

Acrolein has been used as a fixative in preparation of biological specimens for [[electron microscopy]].<ref name=Dykstra>{{cite book | author = M J Dykstra, L E Reuss | date = 2003 | title = Biological Electron Microscopy: Theory, Techniques, and Troubleshooting | publisher = Springer | isbn = 0-306-47749-1}}</ref>

==Health risks==

Acrolein is toxic and is a strong irritant for the skin, eyes, and nasal passages.<ref name=Ullmann/> The main metabolic pathway for acrolein is the [[alkylation]] of [[glutathione]]. The [[World Health Organization|WHO]] suggests a "tolerable oral acrolein intake" of 7.5&nbsp;μg per day per kg of body weight. Although acrolein occurs in [[French fries]] (and other fried foods), the levels are only a few μg per kg.<ref name=ToxRev/> In response to occupational exposures to acrolein, the US [[Occupational Safety and Health Administration]] has set a [[permissible exposure limit]] at 0.1 ppm (0.25&nbsp;mg/m³) at an eight-hour time-weighted average.<ref name=cdc>[https://www.cdc.gov/niosh/npg/npgd0011.html CDC - NIOSH Pocket Guide to Chemical Hazards]</ref> Acrolein acts in an immunosuppressive manner and may promote regulatory cells,<ref>{{cite journal |last1=Roth-Walter |first1=Franziska |last2=Bergmayr |first2=Cornelia |last3=Meitz |first3=Sarah |last4=Buchleitner |first4=Stefan |last5=Stremnitzer |first5=Caroline |last6=Fazekas |first6=Judit |last7=Moskovskich |first7=Anna |last8=Müller |first8=Mario A. |last9=Roth |first9=Georg A. |last10=Manzano-Szalai |first10=Krisztina |last11=Dvorak |first11=Zdenek |last12=Neunkirchner |first12=Alina |last13=Jensen-Jarolim |first13=Erika |author-link13=Erika Jensen-Jarolim |date=2017 |title=Janus-faced Acrolein prevents allergy, but accelerates tumor growth by promoting immunoregulatory Foxp3+ cells: Mouse model for passive respiratory exposure |journal=Scientific Reports |volume=7 |pages=45067 |bibcode=2017NatSR...745067R |doi=10.1038/srep45067 |pmc=5362909 |pmid=28332605}}</ref> thereby preventing the generation of allergies on the one hand, but also increasing the risk of cancer.

Acrolein was identified as one of the chemicals involved in the [[2019 Kim Kim River toxic pollution]] incident.<ref>{{cite web |last1=Tara Thiagarajan |title=8 Chemicals Have Been Identified in Pasir Gudang's Kim Kim River, Here's What They Are |url=https://worldofbuzz.com/8-chemicals-have-been-identified-in-pasir-gudangs-kim-kim-river-heres-what-they-are/ |website=World of Buzz |date=Mar 15, 2019}}</ref>

===Cigarette smoke===

Connections exist between acrolein gas in the smoke from [[tobacco smoking|tobacco cigarettes]] and the risk of [[lung cancer]].<ref name="Feng">{{cite journal | last =Feng | first =Z |author2=Hu W|author3=Hu Y|author4=Tang M | title =Acrolein is a major cigarette-related lung cancer agent: Preferential binding at p53 mutational hotspots and inhibition of DNA repair | journal = [[Proceedings of the National Academy of Sciences]]| volume =103 | issue =42 | pages =15404–15409 |date=October 2006 | pmid =17030796 | doi=10.1073/pnas.0607031103 | pmc =1592536 | bibcode=2006PNAS..10315404F| doi-access =free }}</ref> Acrolein is one of seven [[toxicant]]s in [[cigarette]] smoke that are most associated with [[respiratory tract]] [[carcinogenesis]].<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 acrolein appears to involve induction of increased [[reactive oxygen species]] and [[DNA damage (naturally occurring)|DNA damage]] related to [[oxidative stress]].<ref>Li L, Jiang L, Geng C, Cao J, Zhong L. The role of oxidative stress in acrolein-induced DNA damage in HepG2 cells. Free Radic Res. 2008 Apr;42(4):354-61. doi: 10.1080/10715760802008114 {{PMID|18404534}}</ref>

In terms of the "noncarcinogenic health quotient"{{Technical inline|date=January 2023}} for components in cigarette smoke, acrolein dominates, contributing 40 times more than the next component, [[hydrogen cyanide]].<ref>{{cite journal | last1 = Haussmann | first1 = Hans-Juergen | year = 2012 | title = Use of Hazard Indices for a Theoretical Evaluation of Cigarette Smoke Composition | journal = Chem. Res. Toxicol. | volume = 25 | issue = 4 | pages = 794–810 | doi = 10.1021/tx200536w | pmid = 22352345 }}</ref> The acrolein content in cigarette smoke depends on the type of cigarette and added [[glycerin]], making up to 220&nbsp;μg acrolein per cigarette.<ref>{{cite journal | pmid = 20161525 | doi=10.1016/j.atmosenv.2009.10.004 | volume=44 | issue=1 | title=Comparison of carcinogen, carbon monoxide, and ultrafine particle emissions from narghile waterpipe and cigarette smoking: Sidestream smoke measurements and assessment of second-hand smoke emission factors. | date=Jan 2010 | journal=Atmos Environ | pages=8–14 | pmc=2801144 | last1 = Daher | first1 = N | last2 = Saleh | first2 = R | last3 = Jaroudi | first3 = E | last4 = Sheheitli | first4 = H | last5 = Badr | first5 = T | last6 = Sepetdjian | first6 = E | last7 = Al Rashidi | first7 = M | last8 = Saliba | first8 = N | last9 = Shihadeh | first9 = A| bibcode=2010AtmEn..44....8D }}</ref><ref>{{cite journal | pmid = 26422308 | doi=10.1016/j.chroma.2015.09.034 | volume=1418 | title=Electronic cigarette solutions and resultant aerosol profiles | year=2015 | journal=J Chromatogr A | pages=192–9 | last1 = Herrington | first1 = JS | last2 = Myers | first2 = C| doi-access=free}}</ref> Importantly, while the concentration of the constituents in mainstream smoke can be reduced by filters, this has no significant effect on the composition of the side-stream smoke where acrolein usually resides, and which is inhaled by [[passive smoking]].<ref>{{cite journal | pmid = 26726281 | doi=10.1080/02786826.2015.1076156 | volume=49 | issue=9 | title=A Real-Time Fast-Flow Tube Study of VOC and Particulate Emissions from Electronic, Potentially Reduced-Harm, Conventional, and Reference Cigarettes | pmc=4696598 | year=2015 | journal=Aerosol Sci Technol | pages=816–827 | last1 = Blair | first1 = SL | last2 = Epstein | first2 = SA | last3 = Nizkorodov | first3 = SA | last4 = Staimer | first4 = N| bibcode=2015AerST..49..816B }}</ref><ref>{{cite journal | pmid = 12033743 | doi=10.1038/nri803 | volume=2 | issue=5 | title=Effects of cigarette smoke on the immune system | date=May 2002 | journal=Nat. Rev. Immunol. | pages=372–7 | last1 = Sopori | first1 = M| s2cid=26116099 }}</ref> [[E-cigarette]]s, used normally, only generate "negligible" levels of acrolein (less than 10&nbsp;μg "per puff").<ref name=McNeill2015>{{cite web|last1=McNeill|first1=A, SC|title=E - cigarettes: an evidence update A report commissioned by Public Health England|url=https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/454516/Ecigarettes_an_evidence_update_A_report_commissioned_by_Public_Health_England.pdf|website=www.gov.uk|publisher=Public Health England|access-date=20 August 2015|pages=76–78|location=UK|date=2015}}</ref><ref>{{Cite journal|last1=Sleiman|first1=M|title=Emissions from electronic cigarettes: Key parameters affecting the release of harmful chemicals|journal=Environmental Science and Technology|volume=50|issue=17|pages=9644–9651|date=2016|doi=10.1021/acs.est.6b01741|pmid=27461870|bibcode=2016EnST...50.9644S|s2cid=31872198|url=http://www.escholarship.org/uc/item/9s90850c|hdl=11336/105702|hdl-access=free}}</ref>

===Chemotherapy metabolite===

[[Cyclophosphamide]] and [[ifosfamide]] treatment results in the production of acrolein.<ref name="Paci">{{cite journal | last1 = Paci | first1 = A |last2=Rieutord |first2=A |last3=Guillaume |first3=D |last4=Traore |first4=F |last5=Ropenga |first5=J |last6=Husson |first6=H-P |last7=Brion |first7=F. |display-authors=3 |title=Quantitative high-performance liquid chromatography chromatographic determination of acrolein in plasma after derivatization with Luminarin 3 |journal=[[Journal of Chromatography B]] |volume=739 |issue=2 |pages = 239–246 |date=March 2000 | doi=10.1016/S0378-4347(99)00485-5 | pmid = 10755368 }}</ref> Acrolein produced during cyclophosphamide treatment collects in the urinary bladder and if untreated can cause hemorrhagic cystitis.

=== Endogenous production ===

Acrolein is a component of [[reuterin]].<ref>{{Cite journal |last1=Engels |first1=Christina |last2=Schwab |first2=Clarissa |last3=Zhang |first3=Jianbo |last4=Stevens |first4=Marc J. A. |last5=Bieri |first5=Corinne |last6=Ebert |first6=Marc-Olivier |last7=McNeill |first7=Kristopher |last8=Sturla |first8=Shana J. |last9=Lacroix |first9=Christophe |date=2016-11-07 |title=Acrolein contributes strongly to antimicrobial and heterocyclic amine transformation activities of reuterin |journal=Scientific Reports |language=en |volume=6 |issue=1 |pages=36246 |doi=10.1038/srep36246 |issn=2045-2322 |pmc=5098142 |pmid=27819285|bibcode=2016NatSR...636246E }}</ref> Reuterin can be produced by gut microbes when glycerol is present. Microbe-produced reuterin is a potential resource of acrolein.<ref>{{Cite journal |last1=Zhang |first1=Jianbo |last2=Sturla |first2=Shana |last3=Lacroix |first3=Christophe |last4=Schwab |first4=Clarissa |date=2018-03-07 |editor-last=Johnson |editor-first=Eric A. |title=Gut Microbial Glycerol Metabolism as an Endogenous Acrolein Source |journal=mBio |language=en |volume=9 |issue=1 |pages=e01947–17 |doi=10.1128/mBio.01947-17 |issn=2161-2129 |pmc=5770549 |pmid=29339426}}</ref>

==Analytical methods==

The "acrolein test" is for the presence of [[glycerin]] or [[fat]]s. A sample is heated with [[potassium bisulfate]], and acrolein is released if the test is positive. When a fat is heated strongly in the presence of a dehydrating agent such as potassium bisulfate ({{chem|KHSO|4}}), the glycerol portion of the molecule is dehydrated to form the unsaturated [[aldehyde]], acrolein (CH₂=CH–CHO), which has the odor peculiar to burnt cooking grease. More modern methods exist.<ref name=ToxRev>{{cite journal | last1 = Abraham | first1 = Klaus | last2 = Andres | first2 = Susanne | last3 = Palavinskas | first3 = Richard | last4 = Berg | first4 = Katharina | last5 = Appel | first5 = Klaus E. | last6 = Lampen | first6 = Alfonso | year = 2011 | title = Toxicology and risk assessment of acrolein in food | journal = Mol. Nutr. Food Res. | volume = 55 | issue = 9 | pages = 1277–1290 | doi = 10.1002/mnfr.201100481 | pmid = 21898908}}</ref>

In the US, EPA methods 603 and 624.1 are designed to measure acrolein in industrial and municipal [[wastewater]] streams.<ref>[https://web.archive.org/web/20081121222220/http://www.accustandard.com/asi/pdfs/epa_methods/603.pdf Appendix A To Part 136 Methods For Organic Chemical Analysis of Municipal and Industrial Wastewater, Method 603—Acrolein And Acrylonitrile> ]</ref><ref>[https://www.epa.gov/sites/production/files/2017-08/documents/method_624-1_2016.pdf Method 624.1 — Purgables by GC-MS> ]</ref>

{{Clear}}

==References==

{{reflist}}

{{chemical warfare}}

{{Molecules detected in outer space}}

{{Transient receptor potential channel modulators}}

{{Authority control}}

[[Category:Alkenals]]

[[Category:Hazardous air pollutants]]

[[Category:IARC Group 2A carcinogens]]

[[Category:Lachrymatory agents]]

[[Category:Pulmonary agents]]

[[Category:Foul-smelling chemicals]]

[[hi:एक्रोलिन]]