Methyl isobutyl ketone

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Methyl isobutyl ketone
Image:MIBK.png
General
Systematic name	4-Methyl-2-pentanone
Other names	Isopropylacetone Hexone Isobutyl methyl ketone Isopropylacetone 4-Methylpentan-2-one
Molecular formula	C6H12O
SMILES	CC(C)CC(=O)C
Molar mass	100.2 g/mol
Appearance	colorless liquid
CAS number	[108-10-1]
Properties
Density and phase	0.80 g/ml, liquid
Solubility in water	1.91 g/100 ml (20 °C)
Melting point	−84.7 °C
Boiling point	117-118 °C
Acidity (pKa)	?
Viscosity	0.58 cP at 20.0 °C
Dipole moment	4.2 D
Hazards
MSDS	External MSDS
EU classification	Flammable (F) Harmful (Xn)
NFPA 704	3 2 0
R-phrases	R11, R20, R36/37, R66
S-phrases	(S2), S9, S16, S29
Flash point	14 °C
RTECS number	SA9275000
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related ketones	Methyl isopropyl ketone Pentan-2-one
Related compounds	2-Methylpentan-4-ol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Methyl isobutyl ketone (MIBK) is a ketone that is widely used as a solvent. Unlike the other common ketone solvents, acetone and MEK, MIBK has quite low solubility in water, allowing it to be used for liquid-liquid extraction. It has a similar polarity to the ester solvent ethyl acetate, but higher stability towards aqueous acid or base than ethyl acetate.

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

Image:MIBK synthesis.png

Uses

It is used as a solvent for CS in the preparation of the CS spray used currently by British police forces. ^[1]

When mixed with water or isopropyl alcohol it is also used as a developer for PMMA electron-beam lithography resist.

Another major use is as raw material in the preparation of 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.^{[citation needed]}

References

1. ↑ Peter J Gray (2000). "CS gas is not CS spray - formulation is important" (Response to editorial). BMJ 321: 26. doi:10.1136/bmj.321.7252.46.

External links

• International Chemical Safety Card 0511
• National Pollutant Inventory - Methyl isobutyl ketone fact sheet
• NIOSH Pocket Guide to Chemical Hazardsit:Metilisobutilchetone

nl:Methylisobutylketonfi:Metyyli-isobutyyliketoni