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{{Redirect|MVK|the gene|MVK (gene)|the Hungarian transport company|MVK Zrt.}} |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 402391832 |
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| Name = Methyl vinyl ketone |
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| verifiedrevid = 444013203 |
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| Reference =<ref>''Merck Index'', 11th Edition, '''6052'''.</ref> |
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| Name = Methyl vinyl ketone |
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| ImageFile = MVK-2D-skeletal.png |
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| Reference = <ref>''Merck Index'', 11th Edition, '''6052'''.</ref> |
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| ImageSize = 150px |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageName = Skeletal formula |
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| ImageFile1 = Methyl-vinyl-ketone-3D-balls.png |
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| ImageFile = Methyl vinyl ketone.svg |
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| ImageSize = 150px |
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| ImageName1 = Ball-and-stick model |
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| ImageAlt = Skeletal formula of methyl vinyl ketone |
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| IUPACName = Butenone <!-- the only way to put together a molecule with this name in the way shown, so there is no need for numbers --> |
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| OtherNames = Butenone,<br />Methyl vinyl ketone<br />MVK<br />Methylene acetone |
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| ImageFile1 = Methyl vinyl ketone molecule ball.png |
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| ImageSize1 = 160 |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = Ball-and-stick model of the methyl vinyl ketone molecule |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = But-3-en-2-one <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| OtherNames = MVK<br />Methylene acetone |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6322 |
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| ChemSpiderID = 6322 |
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| PubChem = 6570 |
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| PubChem = 6570 |
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| StdInChIKey = FUSUHKVFWTUUBE-UHFFFAOYSA-N |
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| StdInChIKey = FUSUHKVFWTUUBE-UHFFFAOYSA-N |
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| CASNo = 78-94-4 |
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| CASNo = 78-94-4 |
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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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| ChEBI = 48058 |
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| UNII = AR7642I1MP |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 48058 |
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| SMILES = CC(=O)C=C |
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| SMILES = CC(=O)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 = 0.8407 g/cm<sup>3</sup> |
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| Density = 0.8407 g/cm<sup>3</sup> |
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| MeltingPt = -7 °C |
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| MeltingPtC = −7 |
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| BoilingPt = 81.4 °C |
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| BoilingPtC = 81.4 |
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| HenryConstant = |
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| Section7 = {{Chembox Hazards |
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| NFPA-H = 4 |
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|Section7={{Chembox Hazards |
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| NFPA-F = 3 |
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| NFPA-R = 2 |
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| NFPA-H = 4 |
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| NFPA-F = 3 |
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}} |
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| NFPA-R = 2 |
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| FlashPtC = -7 |
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| AutoignitionPtC = 370 |
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| ExploLimits = 2.1% v/v (lower), 15.6% v/v (higher) |
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| ExternalSDS = |
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| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS02}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Danger |
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}} |
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'''Methyl vinyl ketone''' (MVK) is a reactive organic compound classified as an ]. It is a colorless, flammable, highly toxic liquid with a pungent odor. It is easily soluble in water, ], ], ], and ]. |
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'''Methyl vinyl ketone''' ('''MVK''', IUPAC name: '''butenone''') is the ] with the formula CH<sub>3</sub>C(O)CH=CH<sub>2</sub>. It is a reactive compound classified as an ], in fact the simplest example thereof. It is a colorless, flammable, highly toxic liquid with a pungent odor. It is soluble in water and polar organic solvents. It is a useful intermediate in the synthesis of other compounds.<ref name="ketones"/> |
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==Production== |
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MVK has been prepared industrially by the ] of acetone and ], followed by ]. |
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MVK has been prepared industrially by the ] of ] and ], followed by ]. Similarly it is prepared by the ] involving ] and acetone, which produces the Mannich adduct:<ref name="ketones">{{Ullmann | author = Siegel, H. | author2 = Eggersdorfer, M. | title = Ketones | doi = 10.1002/14356007.a15_077}}</ref><ref name=orgsyn>{{cite journal|last1=L. Wilds|first1=Alfred|last2=Nowak|first2=Robert M.|last3=McCaleb|first3=Kirtland E.|title=1-Diethylamino-3-butanone|journal=Organic Syntheses|date=1957|volume=37|page=18|doi=10.15227/orgsyn.037.0018}}</ref> |
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:CH<sub>3</sub>C(O)CH<sub>3</sub> + CH<sub>2</sub>O + Cl → Cl + H<sub>2</sub>O |
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Heating this ammonium salt releases the ammonium chloride and the MVK:<ref name=orgsyn /> |
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MVK can act as an ] because it is an effective ]. Its alkylating ability is both the source of its high toxicity and the feature that makes it a useful intermediate in ]. MVK will ] spontaneously, and is used in the manufacture of plastic ]s. It is also an intermediate in the synthesis of ]s and ]. |
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:Cl → CH<sub>3</sub>C(O)CH=CH<sub>2</sub> + Cl |
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==Reactivity and applications== |
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MVK can act as an ] because it is an effective ]. It gained early attention for its use in the ], a method useful in the preparation of steroids: |
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:]{{clear-left}} |
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Its alkylating ability is both the source of its high toxicity and the feature that makes it a useful intermediate in ]. MVK will ] spontaneously. The compound is typically stored with ], which inhibits polymerization. |
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:] is a commercial fungicide prepared using MVK.]]{{clear-left}} |
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As an electrophilic alkene, it forms an adduct with ]. The resulting ] ] is an intermediate in the synthesis of the ] drug ]. Via its ] is also a precursor to ]. It is also a precursor to synthetic ].<ref name="ketones"/> |
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MVK is an intermediate in the synthesis of some pharmaceutical drugs including ], ], ], ], and ].{{citation needed|date=March 2017}} |
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MVK is used in the synthesis of ]. |
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==Safety== |
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MVK is extremely hazardous upon inhalation causing coughing, wheezing and shortness of breath even at low concentrations. It will also readily cause irritation of the skin, eyes, and mucous membranes. |
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MVK is extremely hazardous upon inhalation causing coughing, wheezing and shortness of breath even at low concentrations. It will also readily cause irritation of the skin, eyes, and mucous membranes. |
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==References== |
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==References== |
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{{Reflist}} |
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<references/> |
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==External links== |
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==External links== |
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* {{Webarchive|url=https://web.archive.org/web/20061015035017/https://www.mathesontrigas.com/pdfs/msds/MAT14770.pdf#search=%22MSDS%20%22methyl%20vinyl%20ketone%22%22 |date=2006-10-15 }} |
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* . Sander, R. 1999-04-08. |
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