Methyl isobutyl ketone
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2008-06-23T16:47:53Z
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{{Chembox new
| Name = Methyl isobutyl ketone
| ImageFile = MIBK.png
<!-- | ImageSize = 120px -->
| ImageName = Methyl isobutyl ketone
| IUPACName = 4-Methyl-2-pentanone
| OtherNames = Isopropylacetone<br />Hexone<br />Isobutyl methyl ketone<br />Isopropylacetone<br />4-Methylpentan-2-one
| Section1 = {{Chembox Identifiers
| SMILES = CC(C)CC(=O)C
| CASNo = 108-10-1
| RTECS = SA9275000
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>12</sub>O
| MolarMass = 100.2 g/mol
| Appearance = colorless liquid
| Density = 0.80 g/ml, liquid
| Solubility = 1.91 g/100 ml (20 °C)
| MeltingPt = −84.7 °C
| BoilingPt = 117-118 °C
| pKa =
| Viscosity = 0.58 [[Poise|cP]] at 20.0 °C
}}
| Section3 = {{Chembox Structure
| Dipole = 4.2 [[Debye|D]]
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| EUClass = Flammable ('''F''')<br />Harmful ('''Xn''')
| NFPA-H = 2
| NFPA-F = 3
| NFPA-R =
| RPhrases = {{R11}}, {{R20}}, {{R36/37}}, {{R66}}
| SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S29}}
| FlashPt = 14 °C
}}
| Section8 = {{Chembox Related
| Function = [[ketone]]s
| OtherFunctn = [[Methyl isopropyl ketone]]<br />[[Pentan-2-one]]
| OtherCpds = [[2-Methylpentan-4-ol]]
}}
}}
'''Methyl isobutyl ketone''' ('''MIBK''') is a [[ketone]] that is widely used as a [[solvent]]. Unlike the other common ketone solvents, [[acetone]] and [[butanone|MEK]], MIBK has quite low solubility in water, allowing it to be used for [[liquid-liquid extraction]]. It has a similar [[polarity]] to the [[ester]] solvent [[ethyl acetate]], but higher stability towards [[aqueous]] [[acid]] or [[base (chemistry)|base]] than ethyl acetate.
Methyl isobutyl ketone is manufactured from acetone, via a three-step process. Firstly acetone is dimerised via the [[aldol condensation]] to give [[diacetone alcohol]], which readily [[dehydration (chemistry)|dehydrates]] to give [[mesityl oxide]]. Mesityl oxide can then be [[hydrogenation|hydrogenated]] to give MIBK.
[[Image:MIBK synthesis.png|500px|Synthesis of MIBK from acetone]]
==Uses==
It is used as a solvent for CS in the preparation of the [[CS gas|CS spray]] used currently by British police forces.
<ref name=CS>{{cite journal | journal = [[BMJ]] | doi = 10.1136/bmj.321.7252.46 | url = http://bmj.bmjjournals.com/cgi/eletters/320/7233/458 | title = CS gas is not CS spray - formulation is important | format = Response to editorial | author = Peter J Gray | volume = 321 | pages = 26 | year = 2000 | pmid = 10939811}}</ref>
When mixed with water or isopropyl alcohol it is also used as a developer for PMMA electron-beam lithography resist.
Another major use is as raw material in the preparation of [[N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylene diamine]] (6PPD), an [[antiozonant]] used in tires. 6PPD is prepared by reductive coupling of MIBK with [[4-aminodiphenylamine]].{{Fact|date=September 2007}}
Methyl isobutyl ketone is also used as a denaturing agent for [[denatured alcohol]].
Methyl isobutyl ketone (MIBK) can be used to extract gold, silver and other precious metals from [[cyanide]] solutions, such as those found on gold mines, to determine the levels of those dissolved metals. Another solution used for this purpose is Di Iso Butyl Ketone (DIBK).
==References==
<references/>
==External links==
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc05/icsc0511.htm International Chemical Safety Card 0511]
*[http://www.npi.gov.au/database/substance-info/profiles/58.html National Pollutant Inventory - Methyl isobutyl ketone fact sheet]
*[http://www.cdc.gov/niosh/npg/npgd0326.html NIOSH Pocket Guide to Chemical Hazards]
[[Category:Hazardous air pollutants]]
[[Category:Ketones]]
[[Category:Ketone solvents]]
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[[ja:メチルイソブチルケトン]]
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