Chemistry:Methyl isobutyl ketone
| |
| |
| Names | |
|---|---|
| Preferred IUPAC name
4-Methylpentan-2-one | |
Other names
| |
| Identifiers | |
3D model (JSmol)
|
|
| Abbreviations | MIBK |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
|
| KEGG | |
PubChem CID
|
|
| RTECS number |
|
| UNII | |
| UN number | 1245 |
| |
| |
| Properties[1] | |
| C 6H 12O | |
| Molar mass | 100.161 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.7965 g/mL |
| Melting point | −85 °C (−121 °F; 188 K) |
| Boiling point | 115.7 °C (240.3 °F; 388.8 K) |
| Critical point (T, P) | 575.4 K, 3.4 MPa |
| 1.91 g/100 mL (20.0 °C (68.0 °F; 293.1 K)) | |
| Solubility |
|
| log P | 1.31 |
| Vapor pressure | 2.64 kPa |
| −69.7×10−6 cm3/mol | |
Refractive index (nD)
|
1.3962 |
| Viscosity | 0.545 cP |
| Thermochemistry[1] | |
Heat capacity (C)
|
213.3 J⋅mol−1·K-1 |
| Hazards | |
| GHS pictograms |   
|
| GHS Signal word | Danger |
| H225, H319, H332, H336, H351 | |
| P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+361+353, P304+340+312Script error: No such module "Preview warning".Category:GHS errors, P305+351+338, P308+313, P337+313, P370+378, P403+233, P403+235, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 18 °C (64 °F; 291 K)[1] |
| 448 °C (838 °F; 721 K)[1] | |
| Explosive limits | 1.2%–8.0%[1] |
Threshold limit value (TLV)
|
20 ppm (TWA), 75 ppm[1] (STEL) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
2080 mg/kg (oral, rat)[2] |
LC50 (median concentration)
|
11.6 mg/L (4h, rat, vapor)[2] |
| NIOSH (US health exposure limits):Template:Chembox NIOSH (set)/formatPocketGuideLink | |
PEL (Permissible)
|
TWA 100 ppm (410 mg/m3) |
REL (Recommended)
|
|
IDLH (Immediate danger)
|
500 ppm |
| Related compounds | |
Related ketones
|
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
| |
| Infobox references | |
Methyl isobutyl ketone (MIBK, 4-methylpentan-2-one) is an organic compound with the condensed chemical formula (CH
3)
2CHCH
2C(O)CH
3. This ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.[4]
Production
At 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, which readily dehydrates to give 4-methylpent-3-en-2-one (commonly, mesityl oxide).[5][6] Mesityl oxide is then hydrogenated to give MIBK.[citation needed]
Industrially, these three steps are combined. Acetone is treated with a strongly acidic, palladium catalyst-doped cation exchange resin under medium pressure of hydrogen.[7] Several million kilograms are produced annually.[citation needed]
Uses
MIBK is used as a solvent for nitrocellulose, lacquers, and certain polymers and resins.[citation needed]
Precursor to 6PPD
Another 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.[8]
Solvent and niche applications
Unlike the other common ketone solvents, acetone and MEK, MIBK has quite low solubility in water, making it useful for liquid-liquid extraction. For example, the purification of tantalum from its ores often relies on MIBK extractions.[9] It has a similar polarity to ethyl acetate, but greater stability towards aqueous acids and bases.[citation needed]
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.[citation needed]
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.[10][11]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 Template:RubberBible97th
- ↑ 2.0 2.1 2.2 Sigma-Aldrich Co., Methyl isobutyl ketone.
- ↑ "Methyl isobutyl ketone". ThermoFisher Scientific. https://www.fishersci.com/shop/products/methyl-iso-butyl-ketone-certified-acs-fisher-chemical-4/M2134.
- ↑ United States Environmental Protection Agency (January 2000). "Methyl Isobutyl Ketone (Hexone)". https://www.epa.gov/sites/default/files/2016-09/documents/methyl-isobutyl-ketone.pdf. Retrieved 13 May 2026.
- ↑ 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.
- ↑ Uhde GmbH (2005). "Uhde Technology Profile: MIBK". http://www.uhde-ftp.de/cgi-bin/byteserver.pl/pdf/technologies/TP_MIBK_2005.pdf. Retrieved 18 October 2021.
- ↑ Engels, H.-W.; Weidenhaupt, H.-J.; Pieroth, M.; Hofmann, W.; Menting, K.-H.; Mergenhagen, T.; Schmoll, R.; Uhrlandt, S. (2007). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a23_365.pub2.
- ↑ Shikika, A.; Sethurajan, M.; Muvundja, F.; Mugumaoderha, M.C.; Gaydardzhiev, St. (2020). "A review on extractive metallurgy of tantalum and niobium". Hydrometallurgy 198. doi:10.1016/j.hydromet.2020.105496.
- ↑ 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. PMID 10939811.
- ↑ Roger Eardley-Pryor (2017). "A Tear Gas Tale". Science History Institute. https://www.sciencehistory.org/distillations/a-tear-gas-tale#sources. Retrieved 2021-02-22.
 |  |
