Methyl isobutyl ketone

Methyl isobutyl ketone

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
CAS Number	108-10-1 Y
3D model (Jmol)	Interactive image
ChemSpider	7621 N
ECHA InfoCard	100.003.228
EC Number	203-550-1
KEGG	C19263 Y
PubChem	7909
RTECS number	SA9275000
UNII	U5T7B88CNP N
InChI InChI=1S/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3 N Key: NTIZESTWPVYFNL-UHFFFAOYSA-N N InChI=1/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3 Key: NTIZESTWPVYFNL-UHFFFAOYAQ
SMILES CC(C)CC(=O)C
Properties
Chemical formula	C6H12O
Molar mass	100.16 g/mol
Appearance	colorless liquid
Odor	pleasant
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)
Solubility in water	1.91 g/100 mL (20 °C)
Vapor pressure	16 mmHg (20 °C)
Magnetic susceptibility (χ)	-70.05·10−6 cm3/mol
Refractive index (nD)	1.3958
Viscosity	0.58 cP at 20.0 °C
Structure
Dipole moment	2.8 D
Hazards
EU classification (DSD)	Flammable (F) Harmful (Xn)
R-phrases	R11, R20, R36/37, R66
S-phrases	(S2), S9, S16, S29
NFPA 704	3 2
Flash point	14 °C (57 °F; 287 K)
Autoignition temperature	449 °C (840 °F; 722 K)
Explosive limits	1.2%-8.0% (93 °C)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 100 ppm (410 mg/m3)
REL (Recommended)	TWA 50 ppm (205 mg/m3) ST 75 ppm (300 mg/m3)
IDLH (Immediate danger)	500 ppm
Related compounds
Related ketones	Methyl isopropyl ketone 2-Pentanone Diisobutyl ketone
Related compounds	2-Methylpentan-4-ol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Methyl isobutyl ketone (MIBK) is the organic compound with the formula (CH₃)₂CHCH₂C(O)CH₃. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

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:

Industrially, these three steps are combined. Acetone is treated with a strong acidic, palladium-doped cation exchange resin under medium pressure of hydrogen. Several million kilograms are produced annually. In 2003, the industrial production capacity for MIBK in the United States was 88,000 tons.

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

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.

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.