| Revision as of 08:56, 10 June 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified and watched fields - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref') per Chem/Drugbox validation (report [[Wikip← Previous edit |
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| verifiedrevid = 370511059 |
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| verifiedrevid = 433525327 |
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| Name = Methyl isobutyl ketone |
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| Name = Methyl isobutyl ketone |
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| ImageFile = MIBK.png |
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| ImageFile = MIBK.png |
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| ImageSize = |
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| ImageSize = 140 |
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| ImageName = Methyl isobutyl ketone |
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| ImageAlt = Skeletal formula of methyl isobutyl ketone |
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| ImageFile1 = Methyl isobutyl ketone 3D ball.png |
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| IUPACName = 4-Methylpentan-2-one |
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| ImageSize1 = 160 |
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| OtherNames = Isopropylacetone, Hexone, Isobutyl methyl ketone, 4-Methylpentan-2-one, 4-methyl-2-pentanone, 4-methylpentan-2-one, 2-methyl-4-pentanone, 2-methylpropyl methyl ketone, 4-methyl-2-oxopentane, MIK, isobutylmethyl ketone, MIBK, isohexanone |
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| ImageAlt1 = Ball-and-stick model of the methyl isobutyl ketone molecule |
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| Section1 = {{Chembox Identifiers |
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| PIN = 4-Methylpentan-2-one |
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| SMILES = CC(C)CC(=O)C |
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| OtherNames = 4-Methyl-2-pentanone, Isopropylacetone, Hexone, Isobutyl methyl ketone, 2-Methylpropyl methyl ketone, 4-Methyl-2-oxopentane, MIK, Isobutylmethyl ketone, MIBK, Isohexanone |
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| CASNo_Ref = {{cascite}} |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 108-10-1 |
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| CASNo = 108-10-1 |
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| Abbreviations = MIBK |
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| RTECS = SA9275000 |
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| ChEBI = 82344 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| ChEMBL = 285323 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7621 |
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| EINECS = 203-550-1 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19263 |
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| KEGG = C19263 |
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| RTECS = SA9275000 |
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| PubChem = 7909 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = U5T7B88CNP |
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| UNNumber = 1245 |
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| SMILES = CC(C)CC(=O)C |
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| InChI = 1/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3 |
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| InChIKey = NTIZESTWPVYFNL-UHFFFAOYAQ |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = NTIZESTWPVYFNL-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>12</sub>O |
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| Formula = C<sub>6</sub>H<sub>12</sub>O |
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| MolarMass = 100.16 g/mol |
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| MolarMass = 100.16 g/mol |
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| Appearance = colorless liquid |
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| Appearance = colorless liquid |
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| Odor = pleasant<ref name=PGCH/> |
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| Density = 0.802 g/mL, liquid |
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| Solubility = 1.91 g/100 mL (20 °C) |
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| Density = 0.802 g/mL, liquid |
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| Solubility = 1.91 g/100 mL (20 °C) |
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| MeltingPtC = -84.7 |
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| BoilingPtCL = 117 |
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| MeltingPtC = -84.7 |
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| BoilingPtCH = 118 |
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| BoilingPtC = 117 to 118 |
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| pKa = |
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| pKa = |
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| Viscosity = 0.58 ] at 20.0 °C |
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| Viscosity = 0.58 ] at 20.0 °C |
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| RefractIndex = 1.3958 |
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| RefractIndex = 1.3958 |
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| VaporPressure = 16 mmHg (20 °C)<ref name=PGCH/> |
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| MagSus = -70.05·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| Dipole = 4.2 ] |
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| Dipole = 2.8 ] |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| NFPA-H = 2 |
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| EUClass = Flammable ('''F''')<br />Harmful ('''Xn''') |
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| NFPA-H = 2 |
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| NFPA-F = 3 |
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| NFPA-F = 3 |
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| NFPA-R = |
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| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} |
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| NFPA-R = |
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| GHSSignalWord = Danger |
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| RPhrases = {{R11}}, {{R20}}, {{R36/37}}, {{R66}} |
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| HPhrases = {{H-phrases|225|319|332|335|351}} |
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| SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S29}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|303+361+353|304+312|304+340|305+351+338|312|337+313|370+378|403+233|403+235|405|501}} |
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| FlashPt = 14 °C |
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| FlashPtC = 14 |
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| Autoignition = 449 °C |
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| AutoignitionPtC = 449 |
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| IDLH = 500 ppm<ref name=PGCH>{{PGCH|0326}}</ref> |
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| REL = TWA 50 ppm (205 mg/m<sup>3</sup>) ST 75 ppm (300 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| PEL = TWA 100 ppm (410 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| ExploLimits = 1.2–8.0% (93 °C)<ref name=PGCH/> |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = ]s |
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| OtherFunction_label = ]s |
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| OtherFunctn = ]<br />]<br />] |
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| OtherFunction = ]<br />]<br />] |
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| OtherCpds = ] |
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| OtherCompounds = ] |
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}} |
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}}'''Methyl isobutyl ketone''' ('''MIBK''') is the ] with the formula (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>C(O)CH<sub>3</sub>. This colourless liquid, a ], is widely used as a ]. |
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'''Methyl isobutyl ketone''' ('''MIBK''', '''4-methylpentan-2-one''') is an ] with the ] (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>C(O)CH<sub>3</sub>. This ] is a colourless liquid that is used as a ] for gums, resins, paints, varnishes, lacquers, and nitrocellulose.<ref name="US EPA Hexone">{{cite web|last1=United States Environmental Protection Agency | date = September 2016|title=Methyl Isobutyl Ketone (Hexone)|url=http://www3.epa.gov/airtoxics/hlthef/methyl-k.html|accessdate=2015-12-13}}</ref> |
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==Production== |
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==Production== |
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Methyl isobutyl ketone is manufactured from ] via a three-step process. Firstly acetone undergoes an ] to give ], which readily ] to give ]. Mesityl oxide can then be ] to give MIBK: |
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At laboratory scale, MIBK can be produced via a three-step process using ] as the starting material. ], a type of ], produces ],<ref>{{OrgSynth | last1= Conant|first1=J. B.|last2=Tuttle|first2=N. | Org. Synth. |doi=10.15227/orgsyn.001.0045 | title = Diacetone Alcohol | volume= 1 | page = 45| year = 1921}}</ref> which readily ] to give 4-methylpent-3-en-2-one (commonly, ]).<ref>{{OrgSynth | last1= Conant|first1=J. B.|last2=Tuttle|first2=N. | doi= 10.15227/orgsyn.001.0053| title = Mesityl Oxide | volume= 1 | page = 53 | year = 1921}}</ref> Mesityl oxide is then ] to give MIBK.<ref name=Ullmann/> |
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Industrially, these three steps are combined. Acetone is treated with a strongly acidic, ]-doped ] under medium pressure of hydrogen.<ref>{{cite web|last1=Uhde GmbH | date = 2005|title=Uhde Technology Profile: MIBK|url=http://www.uhde-ftp.de/cgi-bin/byteserver.pl/pdf/technologies/TP_MIBK_2005.pdf| archive-url = https://web.archive.org/web/20131203010302/http://www.uhde-ftp.de/cgi-bin/byteserver.pl/pdf/technologies/TP_MIBK_2005.pdf|accessdate=18 October 2021| archive-date = 2013-12-03}}</ref> Several million kilograms are produced annually.<ref name=Ullmann>Stylianos Sifniades, Alan B. Levy, "Acetone" in ''Ullmann’s Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2005.</ref> |
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Modern processes combine these three steps into one.<ref>, Uhde Technology Profile: MIBK</ref> |
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Several million kilograms are produced annually.<ref name=Ullmann>Stylianos Sifniades, Alan B. Levy, “Acetone” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</ref> |
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== Uses == |
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== Uses == |
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MIBK is used as a solvent for nitrocellulose, lacquers, and certain polymers and resins.<ref name=Ullmann/> |
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MIBK is used as a solvent for ], lacquers, and certain polymers and resins.<ref name=Ullmann/> |
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===Precursor to 6PPD=== |
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===Precursor to 6PPD=== |
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Another major use is as a precursor to ''N''-(1,3-dimethylbutyl)-''N'''-phenyl-''p''-phenylene diamine (6PPD), an ] used in tires. 6PPD is prepared by reductive coupling of MIBK with 4-aminodiphenylamine.{{Fact|date=September 2007}} |
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Another major use is as a precursor to ''N''-(1,3-dimethylbutyl)-''N'''-phenyl-''p''-phenylene diamine (]), an ] used in tires. 6PPD is prepared by reductive coupling of MIBK with ].<ref>Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and Additives" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2007, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a23_365.pub2}}</ref> |
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===Solvent and niche applications=== |
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===Solvent and niche applications=== |
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Unlike the other common ketone solvents, ] and ], MIBK has quite low solubility in water, making it useful for ]. It has a similar ] to ], but greater stability towards ] ] and ]. It can be used to extract gold, silver and other precious metals from ] solutions, such as those found at gold mines, to determine the levels of those dissolved metals. Diisobutyl ketone (DIBK), a related lipophilic ketone, is also used for this purpose. Methyl isobutyl ketone is also used as a denaturing agent for ].<!--lots of things are, so what--> When mixed with water or isopropyl alcohol MIBK serves as a ] for ] ] ]. MIBK is used as a solvent for CS in the preparation of the ] used currently by British police forces.<ref name="CS">{{cite journal | journal = ] | 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 | last2 = Stark | first2 = MM | issue = 7252 | pmc = 1127688 | last3 = Gray | first3 = P. J | last4 = Jones | first4 = G R. N}}</ref> |
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Unlike the other common ketone solvents, ] and ], MIBK has quite low solubility in water, making it useful for ]. It has a similar ] to ], but greater stability towards ] ] and ]. It can be used to extract gold, silver and other precious metals from ] solutions, such as those used in gold mines, to determine the levels of those dissolved metals. ] (DIBK), a related lipophilic ketone, is also used for this purpose. Methyl isobutyl ketone is also used as a denaturing agent for ].<!--lots of things are, so what--> When mixed with water or isopropyl alcohol MIBK serves as a ] for ] ] ]. MIBK is used as a solvent for CS in the preparation of the ] used currently by American and British police forces.<ref name="CS">{{cite journal | journal = ] | doi = 10.1136/bmj.321.7252.46 | url = http://bmj.bmjjournals.com/cgi/eletters/320/7233/458 | title = Is CS spray dangerous? : CS is a particulate spray, not a gas | format = Response to editorial | author = Peter J Gray | volume = 321 | pages = 26 | year = 2000 | pmid = 10939811 | last2 = Stark | first2 = MM | issue = 7252 | pmc = 1127688 | last3 = Gray | first3 = P. J | last4 = Jones | first4 = G R. N}}</ref><ref>{{cite journal | author = Roger Eardley-Pryor | journal= Science History Institute | year = 2017 | title = A Tear Gas Tale | url = https://www.sciencehistory.org/distillations/a-tear-gas-tale#sources | accessdate = 2021-02-22 }}</ref> |
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== References == |
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== External links == |
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