Methyl isobutyl ketone (MIBK, 4-methylpentan-2-one) is an organic compound with the condensed chemical formula (CH3)2CHCH2C(O)CH3. This ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.[2]
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| Names | |
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| 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
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | MIBK |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.228 |
| EC Number |
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| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 1245 |
CompTox Dashboard (EPA)
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| 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)
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1.3958 |
| Viscosity | 0.58 cP at 20.0 °C |
| Structure | |
| 2.8 D | |
| Hazards | |
| GHS labelling: | |
  
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| 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)
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TWA 100 ppm (410 mg/m3)[1] |
REL (Recommended)
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TWA 50 ppm (205 mg/m3) ST 75 ppm (300 mg/m3)[1] |
IDLH (Immediate danger)
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500 ppm[1] |
| Related compounds | |
Related ketones
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Methyl isopropyl ketone 2-Pentanone Diisobutyl ketone |
Related compounds
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2-Methylpentan-4-ol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production
editAt laboratory scale, MIBK can be produced via a three-step process using acetone as the starting material. Self-condensation, a type of aldol reaction, produces diacetone alcohol,[3] which readily dehydrates to give 4-methylpent-3-en-2-one (commonly, mesityl oxide).[4] Mesityl oxide is then hydrogenated to give MIBK.[5]
Industrially, these three steps are combined. Acetone is treated with a strongly acidic, palladium catalyst-doped cation exchange resin under medium pressure of hydrogen.[6] Several million kilograms are produced annually.[5]
Uses
edit
MIBK is used as a solvent for nitrocellulose, lacquers, and certain polymers and resins.[5]
Precursor to 6PPD
editAnother major use is as a precursor to 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.[7]
Solvent and niche applications
editUnlike the other common ketone solvents, acetone and MEK, MIBK has quite low solubility in water, making it useful for liquid-liquid extraction. It has a similar polarity to ethyl acetate, but greater stability towards aqueous acid and base. It can be used to extract gold, silver and other precious metals from cyanide 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 for denatured alcohol. When mixed with water or isopropyl alcohol MIBK serves as a developer for PMMA electron beam lithography resist. MIBK is used as a solvent for CS in the preparation of the CS spray used currently by American and British police forces.[8][9]
References
edit- ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0326". National Institute for Occupational Safety and Health (NIOSH).
- ^ United States Environmental Protection Agency (September 2016). "Methyl Isobutyl Ketone (Hexone)". Retrieved 2015-12-13.
- ^ Conant, J. B.; Tuttle, N. (1921). "Diacetone Alcohol". Organic Syntheses. 1: 45. doi:10.15227/orgsyn.001.0045.
- ^ Conant, J. B.; Tuttle, N. (1921). "Mesityl Oxide". Organic Syntheses. 1: 53. doi:10.15227/orgsyn.001.0053.
- ^ a b c Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
- ^ Uhde GmbH (2005). "Uhde Technology Profile: MIBK" (PDF). Archived from the original (PDF) on 2013-12-03. Retrieved 18 October 2021.
- ^ 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
- ^ Peter J Gray; Stark, MM; Gray, P. J; Jones, G R. N (2000). "Is CS spray dangerous? : CS is a particulate spray, not a gas" (Response to editorial). BMJ. 321 (7252): 26. doi:10.1136/bmj.321.7252.46. PMC 1127688. PMID 10939811.
- ^ Roger Eardley-Pryor (2017). "A Tear Gas Tale". Science History Institute. Retrieved 2021-02-22.