p-Menthane

Chemical Properties

p-Menthane is a colorless liquid with a fragrant fennel-like odor. It occurs naturally, especially in exudates of Eucalyptus fruits. The compound is generally encountered as a mixture of the cis and trans isomers, which have very similar properties.

Uses

p-Menthane serves as a precursor for p-menthane hydroperoxide in organic peroxide initiator production. It is also used as a mild-fragrance solvent in soaps, detergents, and air fresheners.

Definition

ChEBI: P-menthane is a terpenoid fundamental parent and a monoterpene. It is used as an intermediate in perfume and flavor manufacturing.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 2507, 1987 DOI: 10.1016/S0040-4039(00)95453-4

General Description

Clear liquid.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

Saturated aliphatic hydrocarbons, such as P-MENTHANE, may be incompatible with strong oxidizing agents like nitric acid. Charring of the hydrocarbon may occur followed by ignition of unreacted hydrocarbon and other nearby combustibles. In other settings, aliphatic saturated hydrocarbons are mostly unreactive. They are not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. When heated sufficiently or when ignited in the presence of air, oxygen or strong oxidizing agents, they burn exothermically to produce carbon dioxide and water.

Fire Hazard

Flash point data for P-MENTHANE are not available, however P-MENTHANE is probably combustible.

Flammability and Explosibility

Flammable

Synthesis

p-Menthane is obtained as a cis/trans mixture by the catalytic hydrogenation of limonene, terpinols, and p-cymene. Raney nickel, platinum, or copper and aluminum oxides are used as catalyst.