Mesityl oxide

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 honey-like odor.[3]

Mesityl oxide
Names
IUPAC name
4-methylpent-3-en-2-one
Other names
Mesityl oxide
Isobutenyl methyl ketone
Methyl isobutenyl ketone
Isopropylidene acetone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.002
EC Number
  • 205-502-5
RTECS number
  • SB4200000
UNII
UN number 1229
Properties
C6H10O
Molar mass 98.145 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
GHS pictograms
GHS Signal word Warning
H226, H302, H312, H332
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+312, P302+352, P303+361+353, P304+312, P304+340, P312, P322, P330, P363, P370+378, P403+235, P501
Flash point 31 °C; 87 °F; 304 K [1]
Explosive limits 1.4–7.2%[1]
Lethal dose or concentration (LD, LC):
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]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 25 ppm (100 mg/m3)[1]
REL (Recommended)
TWA 10 ppm (40 mg/m3)[1]
IDLH (Immediate danger)
1400 ppm[1]
Related compounds
Related compounds
diacetone alcohol
acetone,
benzylideneacetone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Synthesis

It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.[4][5]

Phorone and isophorone may be formed under the same conditions. Isophorone originates via a Michael addition:

Phorone is formed by continued aldol condensation:

Uses

Mesityl oxide is used as a solvent and in the production of methyl isobutyl ketone by hydrogenation:[5]

Complete hydrogenation gives 4-methyl-2-pentanol (methyl isobutyl carbinol).

References

  1. NIOSH Pocket Guide to Chemical Hazards. "#0385". National Institute for Occupational Safety and Health (NIOSH).
  2. "Mesityl oxide". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. Merck Index, 14th Edition
  4. Conant, J. B.; Tuttle, N. (1921). "Mesityl Oxide". Organic Syntheses. 1: 53. doi:10.15227/orgsyn.001.0053.
  5. Sifniades, Stylianos; Levy, Alan B. (2000). "Acetone". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_079. ISBN 3527306730.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.