Mesityl oxide

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Mesityl oxide
Mesityl oxide
Mesityl-oxide-3D-balls.png
Mesityl-oxide-3D-vdW.png
Names
IUPAC name
4-methylpent-3-en-2-one
Other names
Mesityl oxide
Isobutenyl methyl ketone
Methyl isobutenyl ketone
Isopropylidene acetone
Identifiers
141-79-7 YesY
ChemSpider 8526 YesY
Jmol-3D images Image
RTECS number SB4200000
Properties
C6H10O
Molar mass 98.14 g·mol−1
Appearance Oily, colorless to light-yellow liquid[1]
Odor peppermint- or honey-like[1]
Density 0.858 g/cm³
Melting point −53 °C (−63 °F; 220 K)
Boiling point 129.5 °C (265.1 °F; 402.6 K)
3% (20°C)[1]
Solubility in other solvents Soluble in most organic solvents
Vapor pressure 9 mmHg (20°C)[1]
1.442
Hazards
Main hazards flammable
R-phrases R10 R20/21/22
S-phrases S25
Flash point 31 °C; 87 °F; 304 K [1]
Explosive limits 1.4%-7.2%[1]
1120 mg/kg (rat, oral)
1000 mg/kg (rabbit, oral)
710 mg/kg (mouse, oral)[2]
1000 mg/m3 (rat, 4 hr)
9000 mg/m3 (rat, 4 hr)
10,000 mg/m3 (mouse, 2 hr)
2000 mg/m3 (guinea pig, 7 hr)[2]
US health exposure limits (NIOSH):
TWA 25 ppm (100 mg/m3)[1]
TWA 10 ppm (40 mg/m3)[1]
1400 ppm[1]
Related compounds
Related compounds
diacetone alcohol
acetone,
benzylideneacetone
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Mesityl oxide is a α,β-Unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a strong cat urine odor.[3]

Synthesis[edit]

It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.[4]

Acetone mesityl oxide.png

Isophorone may be formed under the same conditions of mesityl oxide production, by a Michael addition. The yields of mesityl oxide and isophorone may vary according to reaction conditions during synthesis:

Isophorone mesityl oxide.png

Uses[edit]

Mesityl oxide is used as a solvent and in the production of methyl isobutyl ketone by hydrogenation:

Hydrogenation of mesityl oxide to MIBK.png

References[edit]

  1. ^ a b c d e f g h i "NIOSH Pocket Guide to Chemical Hazards #0385". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ a b "Mesityl oxide". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ Merck Index, 11th Edition, 5811
  4. ^ J. B. Conant and Neal Tuttle (1941). "Mesityl oxide". Org. Synth. ; Coll. Vol. 1, p. 345 

External links[edit]