Isophorone

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
CAS Number	78-59-1 Y
ChemSpider	6296 Y
EC Number	201-126-0
Jmol 3D model	Interactive image
KEGG	C14743 Y
PubChem	6544
InChI InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3 Y Key: HJOVHMDZYOCNQW-UHFFFAOYSA-N Y InChI=1/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3 Key: HJOVHMDZYOCNQW-UHFFFAOYAC
SMILES O=C1\C=C(/CC(C)(C)C1)C
Properties
Chemical formula	C9H14O
Molar mass	138.21 g·mol−1
Appearance	Colorless to white liquid
Odor	Peppermint-like
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
Vapor pressure	0.3 mmHg (20°C)
Refractive index (nD)	1.4766
Viscosity	2.62 cP
Thermochemistry
Std enthalpy of formation (ΔfHo298)	43.4 kJ/mol
Vapor pressure	{{{value}}}
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

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.

Production

Isophorone can be manufactured by catalyzed self-condensation of acetone. 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.

History

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.

Uses

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

See also

• Phorone