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3.4: Waxes

  • Page ID
    233992
  • Objectives

    After completing this section, you should be able to

    1. identify waxes as being mixtures of long‑chain esters, and write the general structure for such compounds.

    Waxes

    Waxes are esters of fatty acids with long chain monohydric alcohols (one hydroxyl group). Natural waxes are often mixtures of such esters, and may also contain hydrocarbons. Plant waxes on the surfaces of leaves, stems, flowers, and fruits protect the plant from dehydration and invasion by harmful microorganisms. Carnauba wax, used extensively in floor waxes, automobile waxes, and furniture polish, is largely myricyl cerotate, obtained from the leaves of certain Brazilian palm trees. Animals also produce waxes that serve as protective coatings, keeping the surfaces of feathers, skin, and hair pliable and water repellent. In fact, if the waxy coating on the feathers of a water bird is dissolved as a result of the bird swimming in an oil slick, the feathers become wet and heavy, and the bird, unable to maintain its buoyancy, drowns.

    Figure_4_waxes.jpg

    The formulas for three well known waxes are given below, with the carboxylic acid moiety colored red and the alcohol colored blue.

     

    Spermaceti

     

    Beeswax

     

    Carnuba wax

    CH3(CH2)14CO2-(CH2)15CH3

     

    CH3(CH2)24CO2-(CH2)29CH3

     

    CH3(CH2)30CO2-(CH2)33CH3

     

    Cetyl palmitate, a typical wax ester.

    Cetyl palmitate, a typical wax ester.

    Waxes are widely distributed in nature. The leaves and fruits of many plants have waxy coatings, which may protect them from dehydration and small predators. The feathers of birds and the fur of some animals have similar coatings which serve as a water repellent. Carnuba wax is valued for its toughness and water resistance.

     

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