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| Names | |
|---|---|
| Preferred IUPAC name 4-Methylpentan-2-one | |
| Other names 4-Methyl-2-pentanone, Isopropylacetone, Hexone, Isobutyl methyl ketone, 2-Methylpropyl methyl ketone, 4-Methyl-2-oxopentane, MIK, Isobutylmethyl ketone, MIBK, Isohexanone | |
| Identifiers | |
| |
3D model (JSmol) | |
| Abbreviations | MIBK |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.003.228 |
| EC Number |
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| KEGG |
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| RTECS number |
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| UNII | |
| UN number | 1245 |
| |
| |
| Properties | |
| C6H12O | |
| Molar mass | 100.16 g/mol |
| Appearance | colorless liquid |
| Odor | pleasant[1] |
| Density | 0.802 g/mL, liquid |
| Melting point | −84.7 °C (−120.5 °F; 188.5 K) |
| Boiling point | 117 to 118 °C (243 to 244 °F; 390 to 391 K) |
| 1.91 g/100 mL (20 °C) | |
| Vapor pressure | 16 mmHg (20 °C)[1] |
| −70.05·10−6 cm3/mol | |
Refractive index (nD) | 1.3958 |
| Viscosity | 0.58cP at 20.0 °C |
| Structure | |
| 2.8D | |
| Hazards | |
| GHS labelling: | |
   | |
| Danger | |
| H225,H319,H332,H335,H351 | |
| P210,P233,P240,P241,P242,P243,P261,P264,P271,P280,P303+P361+P353,P304+P312,P304+P340,P305+P351+P338,P312,P337+P313,P370+P378,P403+P233,P403+P235,P405,P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 14 °C (57 °F; 287 K) |
| 449 °C (840 °F; 722 K) | |
| Explosive limits | 1.2–8.0% (93 °C)[1] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 100 ppm (410 mg/m3)[1] |
REL (Recommended) | TWA 50 ppm (205 mg/m3) ST 75 ppm (300 mg/m3)[1] |
IDLH (Immediate danger) | 500 ppm[1] |
| Related compounds | |
Relatedketones | Methyl isopropyl ketone 2-Pentanone Diisobutyl ketone |
Related compounds | 2-Methylpentan-4-ol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Methyl isobutyl ketone (MIBK,4-methylpentan-2-one) is anorganic compound with thecondensed chemical formula (CH3)2CHCH2C(O)CH3. Thisketone is a colourless liquid that is used as asolvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.[2]
At laboratory scale, MIBK can be produced via a three-step process usingacetone as the starting material.Self-condensation, a type ofaldol reaction, producesdiacetone alcohol,[3] which readilydehydrates to give 4-methylpent-3-en-2-one (commonly,mesityl oxide).[4] Mesityl oxide is thenhydrogenated to give MIBK.[5]
Industrially, these three steps are combined. Acetone is treated with a strongly acidic,palladium catalyst-dopedcation exchange resin under medium pressure of hydrogen.[6] Several million kilograms are produced annually.[5]
MIBK is used as a solvent fornitrocellulose, lacquers, and certain polymers and resins.[5]
Another major use is as a precursor toN-(1,3-dimethylbutyl)-N'-phenyl-p-phenylene diamine (6PPD), anantiozonant used in tires. 6PPD is prepared by reductive coupling of MIBK with4-aminodiphenylamine.[7]
Unlike the other common ketone solvents,acetone andMEK, MIBK has quite low solubility in water, making it useful forliquid-liquid extraction. It has a similarpolarity toethyl acetate, but greater stability towardsaqueousacid andbase. It can be used to extract gold, silver and other precious metals fromcyanide solutions, such as those used in 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 fordenatured alcohol. When mixed with water or isopropyl alcohol MIBK serves as adeveloper forPMMAelectron beam lithographyresist. MIBK is used as a solvent for CS in the preparation of theCS spray used currently by American and British police forces.[8][9]
