Isophorone

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Isophorone[1]
Isophorone
Identifiers
CAS number 78-59-1 YesY
PubChem 6544
ChemSpider 6296 YesY
EC number 201-126-0
KEGG C14743 YesY
Jmol-3D images Image 1
Properties
Molecular formula 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)
Solubility in water 1.2 g/100 mL
Solubility ether, acetone, hexane, dichloromethane, benzene, toluene, alcohol
Refractive index (nD) 1.4766
Viscosity 2.62 cP
Thermochemistry
Std enthalpy of
formation
ΔfHo298
43.4 kJ/mol
Hazards
Flash point 84 °C (183 °F; 357 K)
LD50 2280 mg/kg (rat, oral)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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.[3]

Production[edit]

Isophorone can be manufactured by catalyzed self-condensation of acetone.[4] 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.[5]

Uses[edit]

Isophorone is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticides.[3] 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. ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  3. ^ a b Chronic Toxicity Summary
  4. ^ U.S. Patent 5,849,957
  5. ^ Isophorone history at Degussa