Waxes…
Waxes are esters of long-chain fatty acids with
long-chain alcohols. They occur widely in
Nature and serve a number of purposes in
plants and animals.
Found in the head of the sperm whale,
probably helps to regulate the animal’s
buoyancy for Deep diving. It may also serve to
amplify high-frequency sounds for locating
prey. Beeswax Is a mixture of waxes,
hydrocarbons, and alcohols that bees use to
form their honeycomb.
Carnauba wax is a mixture of waxes of very
high molecular weights. The carnauba plant
Secretes this waxy material to coat its leaves to
prevent excessive loss of water by evaporation.
Waxes are also found in the protective coatings
of insects’ exoskeletons, mammals’ Fur, and
birds’ feathers. In contrast to these waxes, the
“paraffin wax” used to seal preserves is not a
true wax; rather, it is a mixture of high-
molecular-weight alkanes.
Plant leaves often have a wax coating
To prevent excessive loss of water.
For many years, natural waxes were used in
making cosmetics, adhesives, varnishes, and
waterproofing materials. Synthetic materials
have now replaced natural waxes for most
of these uses.
Glycerides are simply fatty acid esters of the
triol glycerol. The most common glycerides
are triglycerides (triacylglycerols), in which all
three of the glycerol groups
have been esterified by fatty acids.
The fatty acids of common triglycerides are
long, unbranched carboxylic acids with
about 12 to 20 carbon atoms. Most fatty acids
contain even numbers of carbon atoms
because they are derived from two-carbon
acetic acid units. Some of the common fatty
acids have saturated carbon chains, while
others have one or more carbon–carbon
double bonds. saturated fatty acids have
melting points that increase gradually with
their molecular weights. The presence of a cis
double bond lowers the melting point,
however. Notice that the 18-carbon saturated
acid (stearic acid) has a melting point of 70 °C,
while the 18-carbon acid with a cis double bond
(oleic acid) has a melting point of 4 °C. This
lowering of the melting point results from the
unsaturated acid’s “kink” at the position of the
double bond . Kinked molecules cannot pack As
tightly together in a solid as the uniform zigzag
chains of a saturated acid.
Saponification of Fats and Oils; Soaps And
Detergents
Saponification is the base-promoted hydrolysis
of the ester linkages in fats and oils. One of the
products is soap, and the word saponification is
Derived from the Latin word saponis, meaning
“soap.” Saponification was discovered Before
500 B.C., when people found that a curdy
material resulted when animal fat was
Heated with wood ashes. Alkaline substances in
the ashes promote hydrolysis of the Ester
linkages of the fat. Soap is currently made by
boiling animal fat or vegetable oil With a
solution of sodium hydroxide. The following
reaction shows formation of soap
From tristearin, a component of beef fat.
Chemically, a soap is the sodium or potassium
salt of a fatty acid. The negatively charged
carboxylate group is hydrophilic (“attracted to
water”), and the long hydrocarbon chain is
hydrophobic .
In water, soap forms a cloudy solution of
micelles: clusters of about 100 to 200 soap
molecules with their polar “heads” (the
carboxylate groups) on the surface of the
cluster and their hydrophobic “tails”
Emulsification of grease. In a soapy Solution,
grease is emulsified by Forming micelles coated
by the Hydrophilic carboxylate groups
Of the soap.
Synthetic detergents avoid precipitation by
using other functional groups in place of
carboxylic acid salts. Sodium salts of sulfonic
acids are the most widely used class
of synthetic detergents. Sulfonic acids are more
acidic than carboxylic acids, so their salts
are not protonated, even in strongly acidic
wash water. Calcium, magnesium, and iron
salts of sulfonic acids are soluble in water, so
sulfonate salts can be used in hard water
without forming a scum.
