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{{short description|Chemical compound}} |
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{{About|α-methacrolein|β-methacrolein|crotonaldehyde}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 402388253 |
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| verifiedrevid = 435632264 |
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| Name = Methacrolein |
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| Name = Methacrolein |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1 = Methacrolein.png |
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| ImageFileL1 = Methacrolein.png |
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| ImageNameL1 = Skeletal formula of methacrolein |
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| ImageSizeL1 = 120px |
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| ImageFileR1 = Methacrolein-3D-balls-A.png |
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| ImageNameL1 = Skeletal formula of methacrolein |
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| ImageNameR1 = Ball-and-stick model of methacrolein |
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| ImageFileR1 = Methacrolein-3D-balls-A.png |
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| PIN = 2-Methylprop-2-enal |
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| ImageSizeR1 = 120px |
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| OtherNames = Methacrolein<br />Methacrylaldehyde<br />Isobutenal |
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| ImageNameR1 = Ball-and-stick model of methacrolein |
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|Section1={{Chembox Identifiers |
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| IUPACName = 2-Methylprop-2-enal |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames = Methacrolein<br />Methacrylaldehyde<br />Isobutenal |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6314 |
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| ChemSpiderID = 6314 |
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| PubChem = 6562 |
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| PubChem = 6562 |
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| StdInChIKey = STNJBCKSHOAVAJ-UHFFFAOYSA-N |
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| StdInChIKey = STNJBCKSHOAVAJ-UHFFFAOYSA-N |
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| CASNo = 78-85-3 |
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| CASNo = 78-85-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = O=CC(=C)C |
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| UNII = 9HRB24892H |
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| SMILES = O=CC(=C)C |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>4</sub>H<sub>6</sub>O |
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| Formula = C<sub>4</sub>H<sub>6</sub>O |
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| MolarMass = 70.09 g/mol |
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| MolarMass = 70.09 g/mol |
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| Density = 0.8470 g/cm³ |
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| Density = 0.847 g/cm<sup>3</sup> |
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| MeltingPt = -81 °C |
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| MeltingPtC = −81 |
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| BoilingPt = 69 °C |
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| BoilingPtC = 69 |
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}} |
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| Section3 = {{Chembox Related |
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|Section3={{Chembox Related |
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| Function = alkenals |
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| OtherFunction_label = alkenals |
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| OtherFunctn = ]<br /> |
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| OtherFunction = ]<br /> |
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'''Methacrolein''', or methacrylaldehyde, is an ] ]. It is a clear, colorless, flammable liquid that is present in cigarettes when smoking.<ref>{{cite web | title=The risks of passive smoking | url=http://books.google.com/books?id=QZcOAAAAQAAJ&pg=PA23&lpg=PA23&source=bl&ots=GBx_oT-Kaj&sig=lYwIEipofbvcxbNebf52pYp125A&hl=en&ei=FtcASr6TCqXYswP3-5H7BQ&sa=X&oi=book_result&ct=result&resnum=2 | work=Google Books Search | author=Roy J. Shephard | date=1982 | accessdate=2009-05-06}}</ref> |
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'''Methacrolein''', or methacrylaldehyde, is an ] ]. It is a clear, colorless, flammable liquid. |
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Methacrolein is one of two major products resulting from the reaction of ] with OH in the atmosphere, the other product being ] (MVK, also known as butenone).<ref>{{cite journal | doi = 10.1029/92JD02382 | title = Isoprene and its oxidation products, methyl vinyl ketone and methacrolein, in the rural troposphere | journal = Journal of Geophysical Research: Atmospheres | volume = 98 | issue = D1 | pages = 1101–1111 | year = 1993 | last1 = Montzka | first1 = S. A. | last2 = Trainer | first2 = M. | last3 = Goldan | first3 = P. D. | last4 = Kuster | first4 = W. C. | last5 = Fehsenfeld | first5 = F. C. | bibcode = 1993JGR....98.1101M | url = https://zenodo.org/record/1231331}}</ref> These compounds are important components of the atmospheric oxidation chemistry of biogenic chemicals, which can result in the formation of ozone and/or particulates. Methacrylaldehyde is also present in cigarette smoke.<ref>{{cite book | title=The risks of passive smoking| url=https://books.google.com/books?id=QZcOAAAAQAAJ&pg=PA23 | author=Roy J. Shephard | date=1982 | access-date=2009-05-06| isbn=978-0-7099-2334-3}}</ref> It can be found in the ] of the plant ] (''Artemisia tridentata'') which contains 5% methacrolein.<ref>{{cite book|author=Shakhnoza, Azimova S.|title=Lipids, Lipophilic Components and Essential Oils from Plant Sources|publisher=Springer|year=2012|isbn=978-0-85729-323-7|page=844|url=https://books.google.com/books?id=w74gD4-YxaQC&pg=PT844|display-authors=etal}}</ref> |
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Industrially, the primary use of methacrolein is in the manufacture of ]s and synthetic ]s. |
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Industrially, the primary use of methacrolein is in the manufacture of ]s and synthetic ]s. |
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==External links== |
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==External links== |
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{{Authority control}} |
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{{organic-compound-stub}} |
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