Methyl isobutyl ketone 2254792 221228585 2008-06-23T16:47:53Z DOI bot 6652755 Citation maintenance. Initiated by [[User:Fconaway|Fconaway]]. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{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 = &minus;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]] [[de:Methylisobutylketon]] [[it:Metilisobutilchetone]] [[nl:Methylisobutylketon]] [[ja:メチルイソブチルケトン]] [[fi:Metyyli-isobutyyliketoni]]