Isophorone

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Isophorone[1]
Isophorone
Names
IUPAC name
3,5,5-Trimethyl-2-cyclohexene-1-one
Other names
1,1,3-Trimethyl-3-cyclohexene-5-one
Isoforone
Isoacetophorone
IP
Identifiers
78-59-1 YesY
ChemSpider 6296 YesY
EC number 201-126-0
Jmol-3D images Image
KEGG C14743 YesY
PubChem 6544
Properties
C9H14O
Molar mass 138.21 g·mol−1
Appearance Colorless to white liquid
Odor Peppermint-like[2]
Density 0.9255 g/cm3
Melting point −8.1 °C (17.4 °F; 265.0 K)
Boiling point 215.32 °C (419.58 °F; 488.47 K)
1.2 g/100 mL
Solubility ether, acetone, hexane, dichloromethane, benzene, toluene, alcohol
Vapor pressure 0.3 mmHg (20°C)[2]
1.4766
Viscosity 2.62 cP
Thermochemistry
43.4 kJ/mol
Hazards
Flash point 84 °C (183 °F; 357 K)
460 °C (860 °F; 733 K)
Explosive limits 0.8%-3.8%[2]
Lethal dose or concentration (LD, LC):
2280 mg/kg (rat, oral)[citation needed]
2330 mg/kg (rat, oral)
2690 mg/kg (mouse, oral)[3]
4600 ppm (guinea pig, 8 hr)[3]
885 ppm (rat, 6 hr)
1840 ppm (rat, 4 hr)[3]
US health exposure limits (NIOSH):
TWA 25 ppm (140 mg/m3)[2]
TWA 4 ppm (23 mg/m3)[2]
200 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Isophorone is an α,β-unsaturated cyclic ketone, a colorless to yellowish liquid with a characteristic peppermint-like smell. It is used as a solvent and as an intermediate in organic synthesis. Isophorone also occurs naturally in cranberries.[4]

Production[edit]

Isophorone can be manufactured by catalyzed self-condensation of acetone.[5] Mesityl oxide is the initial product of the self-aldol condensation of acetone. The mesityl oxide formed can react further with acetone via a Michael reaction and subsequent intramolecular aldol condensation to eventually obtain the six-membered ring of isophorone. This is an example of the Robinson annulation. The yield of the two compounds depends on the reaction conditions.

Isophorone mesityl oxide.png

History[edit]

The use of isophorone as a solvent resulted from the search for ways to dispose of or recycle acetone, which is a waste product of phenol synthesis by the Hock method.[6]

Uses[edit]

Isophorone is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticides.[4] It is also used as a chemical intermediate and as an ingredient in wood preservatives and floor sealants.

See also[edit]

References[edit]

  1. ^ Merck Index, 13th Edition, 5215.
  2. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0355". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ a b c "Isophorone". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  4. ^ a b Chronic Toxicity Summary
  5. ^ U.S. Patent 5,849,957
  6. ^ Isophorone history at Degussa