Methyl isobutyl ketone

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Methyl isobutyl ketone
Names
IUPAC name
4-Methylpentan-2-one
Other names
4-Methyl-2-oxopentane
4-Methyl-2-pentanone
2-Methylpropyl methyl ketone
Hexone
Isobutyl methyl ketone
Isobutylmethyl ketone
Isohexanone
Isopropylacetone
MIBK
Properties
C6H12O
(CH3)2CHCH2C(O)CH3
Molar mass 100.16 g/mol
Appearance Colorless liquid
Odor Pleasant, camphor-like
Density 0.802 g/cm3 (20 °C)
Melting point −84.7 °C (−120.5 °F; 188.5 K)
Boiling point 117–118 °C (243–244 °F; 390–391 K)
1.91 g/100 ml (20 °C)
Solubility Miscible with acetone, benzene, chloroform, diethyl ether, ethanol
Vapor pressure 16 mmHg (20 °C)
Hazards
Safety data sheet Sigma-Aldrich
Flash point 14 °C (57 °F; 287 K)
Lethal dose or concentration (LD, LC):
2.080 mg/kg (rat, oral)
Related compounds
Related compounds
Methyl ethyl ketone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methyl isobutyl ketone (MIBK) is the organic compound with the formula (CH3)2CHCH2C(O)CH3.

Properties

Chemical

Methyl isobutyl ketone is flammable and will burn if ignited in open air, releasing carbon dioxide, water vapors and soot.

Reductive coupling of MIBK with 4-aminodiphenylamine yields N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylene diamine (6PPD), an antiozonant used in tires.

Physical

MIBK is a colorless liquid, with a pleasant odor, which is flammable and somewhat volatile.

Unlike the other common ketone solvents, such as acetone and MEK, MIBK has quite low solubility in water, making it useful for liquid-liquid extractions.

Availability

MIBK is sold by chemical suppliers.

In US, it is classified as DEA list II chemical, due to its use as substitute ketone in the processing of cocaine. Other countries may have similar restrictions.

Preparation

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

Projects

  • Liquid-liquid extractions
  • Solvent for nitrocellulose, lacquers, polymers, resins
  • Make 6PPD, an antiozonant used in tires

Handling

Safety

MIBK is irritant and flammable.

Storage

Should be kept in closed bottles.

Disposal

Can be safely burned outside or in an incinerator.

References

Relevant Sciencemadness threads