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Methyl isobutyl ketone

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Methyl isobutyl ketone
Methyl isobutyl ketone
Names
IUPAC name 4-Methylpentan-2-one
Other names 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
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.003.228 Edit this at Wikidata
KEGG
RTECS number
  • SA9275000
CompTox Dashboard (EPA)
SMILES
  • CC(C)CC(=O)C
Properties
Chemical formula C6H12O
Molar mass 100.16 g/mol
Appearance colorless liquid
Density 0.802 g/mL, liquid
Melting point −84.7 °C (−120.5 °F; 188.5 K)
Solubility in water 1.91 g/100 mL (20 °C)
Refractive index (nD) 1.3958
Viscosity 0.58 cP at 20.0 °C
Structure
Dipole moment 4.2 D
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability (yellow): no hazard codeSpecial hazards (white): no code
2 3
Flash point 14 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Methyl isobutyl ketone (MIBK) is the organic compound with the formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is widely used as a solvent.

Production

Methyl isobutyl ketone is manufactured from acetone via a three-step process. Firstly acetone undergoes an aldol condensation to give diacetone alcohol, which readily dehydrates to give mesityl oxide. Mesityl oxide can then be hydrogenated to give MIBK:

Synthesis of MIBK from acetone

Modern processes combine these three steps into one.

Several million kilograms are produced annually.

Uses

MIBK is used as a solvent for nitrocellulose, lacquers, and certain polymers and resins.

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.

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. 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 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 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 British police forces.

References

  1. , Uhde Technology Profile: MIBK
  2. ^ Stylianos Sifniades, Alan B. Levy, “Acetone” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  3. Peter J Gray; Stark, MM; Gray, P. J; Jones, G R. N (2000). "CS gas is not CS spray - formulation is important" (Response to editorial). BMJ. 321 (7252): 26. doi:10.1136/bmj.321.7252.46. PMC 1127688. PMID 10939811.

External links

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