Methyl hexanoate

Description

Methyl hexanoate has an ether-like odor reminiscent of pineapple. May be prepared by reacting methyl alcohol with hexanoic acid at 130 - 140°C in the presence of concentrated H2S04 and distilling the ester from the reaction mixture.

Chemical properties

colourless liquid

Chemical properties

Methyl hexanoate has an ether-like odor reminiscent of pineapple

Occurrence

Reported found in pineapple, apple, apricot, orange juice, black currants, guava, grapes, melon, papaya, pineapple, raspberry, blackberry, strawberry, potato, tomato, pepper, rye bread, cheeses, butter, milk, beef mutton, hop oil, beer, grape wine, cider, coffee, tea, honey, cloudberry, durian (Durio zibethinus), olive, passion fruit, plumcot, mushroom, starfruit, mango, wood apple, licorice, soursop, cashew apple, wort, cherimoya, kiwifruit, babaco fruit (Carica pentagona Heilborn), Bourbon vanilla, mountain papaya, oyster, custard apple, nectarine, naranjilla, lamb’s lettuce, loganberry, cape gooseberry, spineless monkey orange, Chinese quince and pawpaw.

The Uses of Methyl hexanoate

Intermediate for caproic acid detergents, emulsifiers, wetting agents, stabilizers, resins, lubricants, plasticizers, flavoring.

Definition

ChEBI: A fatty acid methyl ester derived from hexanoic (caproic acid).

Preparation

By reacting methyl alcohol with hexanoic acid at 130 to 140°C in the presence of concentrated H2SO4 and distilling the ester from the reaction mixture

Aroma threshold values

Detection: 10 to 87 ppb

Synthesis Reference(s)

Tetrahedron, 35, p. 2169, 1979 DOI: 10.1016/0040-4020(79)87035-0
Tetrahedron Letters, 30, p. 2945, 1989 DOI: 10.1016/S0040-4039(00)99165-2

General Description

Clear colorless liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Methyl hexanoate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Methyl hexanoate reacts with strong oxidizing agents and strong bases.

Fire Hazard

Methyl hexanoate is combustible.

Flammability and Explosibility

Flammable

Synthesis

Methyl caproate is synthesized by direct esterification of n-Caproic (n-Hexanoic) acid with Methanol, preferably under azeotropic conditions.

Purification Methods

Pass it through alumina and distil it before use. [Beilstein 2 IV 921.]