Wax
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A wax is a simple lipid which is an ester of a long-chain alcohol and a fatty acid. The
alcohol may contain from 12-32 carbon atoms. Waxes are found in nature as coatings
on leaves and stems. The wax prevents the plant from losing excessive amounts of
water. Carnuba wax is found on the leaves of Brazilian palm trees and is used in floor
and automobile waxes. Lanolin coats lambs, wool. Beeswax is secreted by bees to make
cells for honey and eggs. Spermaceti wax is found in the head cavities and blubber of
the sperm whale. Many of the waxes mentioned are used in ointments, hand creams,
and cosmetics (read the ingredients lists).
Introduction
Paraffin wax, used in some candles, is not based upon the ester functional group, but is
a mixture of high molecular weight alkanes. Ear wax is a mixture of phospholipids and
esters of cholesterol. The waxes with their component alcohols and fatty acids are listed
below.
Waxes
Wax Alcohol Fatty Acid
Carnuba CH3(CH2)28CH2-OH CH3(CH2)24COOH
Beeswax CH3(CH2)28CH2-OH CH3(CH2)14COOH
Spermacetic CH3(CH2)14CH2-OH CH3(CH2)14COOH
Ester Synthesis
Simple esters are made from an organic acid and an alcohol. The ester functional group
is of primary importance in the biochemical group of compounds called waxes,
triglycerides, and phospholipids. The simplified reaction reveals the process of
breaking some bonds and forming the ester and the by product, water. Refer to the
graphic on the left for the synthesis of carnuba wax.
First, the -OH (red) bond on the acid is broken and the -H (red) bond on the alcohol is
also broken. Both join to make HOH, a water molecule. Secondly, the oxygen of the
alcohol forms a bond (green) to the acid at the carbon with the double bond oxygen.
This forms the ester functional group. The long carbon chains do not participate in the
reaction, but are just part of the final molecule.
Lipstick
Lipstick consists of a suspension of coloring agents in high molecular weight
hydrocarbons, waxes, and/or fats. The color usually comes from a dye precipitated by
a metal ion such as Fe (III), Ni(II), or Co(II) ions. An ingredients list may be: dye (4-
8%); castor oil, paraffin, or fats to dissolve dye (50%); lanolin (25%); carnauba and/or
beeswax as a stiffening agent (36%); perfume (1.5%). The lipstick is made by first
dispersing the dye in the castor oil. Then the other waxes and lanolin are added as the
mixture is heated and stirred. The molten waxes are then cast in suitable forms to
harden.
Eye Makeup
Eyebrow pencils are very much like lipstick but contain lamp black (carbon soot) as a
black coloring agent. A different mixture of waxes may be used to give the desired
melting point. Brown pencils are made by adding iron oxide (rust) as a pigment. A
water-resistant mascara has a mixture of waxes, fats, oils, and soap. Other coloring
agents in addition to blacks and browns may be chromic oxide (dark green) and
ultramarine (blue pigment of sodium and aluminum silicate).
Questions
1. For practice write the structures of beeswax and spermacetic wax using the
information in the table.
2. Based upon the structure are waxes likely to be soluble in water?
Contributors
Charles Ophardt (Professor Emeritus, Elmhurst College); Virtual Chembook
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