Soap Synthesis

EXPERIMENT-4: SOAP SYNTHESIS
OBJECTIVE
To synthesize soap by reaction between an alkaline and a fatty acid.
THEORY
A soap is a salt of a fatty acid. Fatty acids are carboxylic acids with a long unbranched
hydrocarbon (aliphatic) chains.
Figure 1. A typical fatty acid
Soap can be prepared from certain esters by a process known as saponification. The
reaction in making soap (saponification) is a base (usually NaOH or KOH) hydrolysis of
triglycerides to make three salts (soap) and glycerol. The molecules crystallize differently
depending on the base used. NaOH produces a harder bar while KOH is used more frequently
for liquid soaps.
Scheme 1. General synthesis of soap
Sodium palmitate CH3(CH2)14COO-Na+ is the salt of palmitic acid

CH3(CH2)14COOH, a fatty acid with a 16 carbon chain. Fatty acids are straight-chain
monocarboxylic acids with a general formula CH3(CH2)nCOOH where n usually varies
between 8 and 18. In nature, most fatty acids are present as triglycerides. Natural fats and oils
usually include different fatty acids. For example, the saponification reaction of a component of
olive oil would produce the salts of palmitic acid and stearic acid.
Hydrophobic tail (non-polar) Hydrophilic head (polar)
Figure 2. Hydrophobic and hydrophilic part of soap

Notice the particular structure of the soap molecule: it has a long nonpolar tail (the
hydrocarbon chain of the fatty acid) and a highly polar end (the ionic group COO -) (Figure 2).
The non-polar or hydrophobic tail can dissolve the grease and dirt whereas the polar or
hydrophylic end is attracted to water molecules.
Adjacent negatively charged heads repel each other forcing the soap molecules into a
spherical shape, a micelle. The soap molecules orient themselves with the nonpolar tails towards
the center of the micelle and the COO- groups facing the water. In the presence of oil (or dirt),
the nonpolar tails interact with the oil that ends up at the center of the micelle. This is how soap
cleans: the dirt and the grease stay at the center of the micelles which repel each other due to the
negatively charged outer surface. Rinsing with water washes the micelles (and the dirt) away.
Soap is acting as an emulsifying agent. Recall that an emulsion is the dispersion of a liquid in a
second immiscible liquid.
Figure 3. Diagram of a soap micelle
The nonpolar tails of the soap molecules attract dirt and the polar heads attract water
molecules. The cleaning properties of soap are intimately related to the fact that there is a highly
polar head and a nonpolar tail in each soap molecule. If the ionic charge of the polar head were
to disappear, the soap molecules would not be able to interact with water, micelles would not
form, and soap would not clean. This is what happens in acidic or hard water. In acidic water,
the COO- group gets protonated and the fatty acid precipitates, being now water insoluble.
Today there are a variety of detergents, which in general contain a surfactant, a builder,
and other additives (such as bleaching agents and enzymes). The surfactants are the chemical
equivalent of the soap and they are responsible for the cleaning properties of the detergent.
Some of them are anionic, some of them are cationic and some of them are non-ionic. For
example:
Materials Chemicals
 Beaker Olive oil
 Heating mantle
Ethanol
 Pipette
 Filter paper 5 M NaOH Solution
NaCl Solution
Notes:
1. NaOH is corrosive to skin and clothing. Avoid contact. Wash hands before leaving the
laboratory. Ethanol is flammable so be sure that there are no open flames in the
laboratory.
2. Important: as it is heating, some of the solution will evaporate. You must make sure
that the volume does not decrease too much, so you will need to add moreliquid as the
reaction progresses.
3. Caution: the mixture of oil and ethanol will be very hot, and may splatter or catch fire.
Have a watch glass nearby to smother any flames. Wear goggles at all times, because
NaOH can cause permanent eye damage!
PROCEDURE
 Add 5 mL of olive oil and 10 mL ethanol in 100 mL beaker and this mixture
is stirred.
 Slowly add 20 mL of 5 M NaOH to the solution. Stir and keep hot for 30 minutes.
 To warm solution, add 25 mL of saturated NaCl solution.
 Remove the beaker and allow the solution to cool to room temperature
 The soap will precipitate out of solution.
 Collect the soap by vacuum filtration.

Soap Synthesis

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EXPERIMENT-4: SOAP SYNTHESIS

To synthesize soap by reaction between an alkaline and a fatty acid.

Figure 1. A typical fatty acid

Scheme 1. General synthesis of soap

Sodium palmitate CH3(CH2)14COO-Na+ is the salt of palmitic acid

Figure 2. Hydrophobic and hydrophilic part of soap

Figure 3. Diagram of a soap micelle

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