INTRODUCTION

Soap is a generic term for the sodium and potassium salts of long-chain organic acids (fatty
acids ) made from naturally occurring esters in animal fats and vegetable oils. Soap is a
product for cleaning made from natural elements that may include both plant and animal
products, including items as animal fat, such as tallow or vegetable oil, such as castor, olive,
or coconut oil (1). All organic acid has RCO2H functional group, where R is a shorthand
notation for methyl, ethyl, propyl or more complex hydrocarbon chains called alkyl groups.

The R groups in soaps are hydrocarbon chains that generally contain 12 to 18 carbon atoms.
Sodium fatty acids such as lauric (vegetable oil), palmitic (palm oil), and stearic acid (animal
fat) acids are just few examples of soaps.

CH3(CH2)10COONa sodium laurate

CH3(CH2)16COONa sodium stearate

The hydrocarbon chain in soaps may contain saturated (no double bond) or unsaturated
chains (contains double bonds). Sodium salts are usually solid therefore most bars of soap are
of sodium salts. Potassium salts are the basis of liquid soaps, shaving creams, and greases.
Fats and vegetable oils are triglycerides. A triglyceride is formed when the three hydroxyl
(OH-) groups of a single glycerol molecule react with the carboxyl group (COOH-) of three
fatty acids by forming ester bonds.
The three fatty acids included in the structure of the triglyceride may or may not be the same
in different triglycerides, such that there are many possible variations. The length of the fatty
acid chains occurring in triglycerides can vary but are most commonly 16, 18 and 20 (2).
carbons. A triglyceride made up from three lauric acid molecules is shown in figure 1.
 Figure 1: formation of triglyceride

Esters can be cleaved back into a carboxylic acid and an alcohol by reaction with water and a
base. The reaction is called a saponification from the Latin sapo which means soap. The
name comes from the fact that soap used to me made by the ester hydrolysis of fats. Due to
the basic conditions a carboxylate ion is made rather than a carboxylic acid. ( Eq 1).

Equation 1

A lone pair of electrons on the OH- is attracted to the partially charged C atom in the C=O
bond in the ester. The C-OR bond breaks generating a carboxylic acid (RCO2H) and an
alcohol (ROH). In the presence of NaOH, carboxylic are converted to their sodium salts
(RCO2-Na+).( Figure 2)
 Mechanism
1) Nucleophilic attack by hydroxide

2) Leaving group removal

3) Deprotonation

Figure 2: mechanism of saponification

When a triglyceride is saponified, three fatty acid salts (soaps) and glycerol are produced as
shown in (Eq 2). The R groups in the triglyceride may or may not have the same chain length
(same number of carbon). Thus, different types of soaps may be produced from the
saponification of a particular glyceride.
 Equation 2

The soap molecule has two parts: a polar group (-COO-Na+) and a non-polar group (R-
hydrocarbon part). The polar group is called the head and the non-polar group is called the
tail. Thus, the soap molecule has a polar head and a non-polar hydrocarbon tail. The polar
head is hydrophilic in nature (water loving) and the non-polar tail is hydrophobic (water
repelling) in nature.( Figure 3) (3).
Depending upon the nature of alkali used in the production of soap, they are classified into
two types.
The sodium salt of long chain fatty acid is known as hard soap. It is difficult to dissolve in
water. It is used as laundry soap.
The potassium salt of long chain fatty acid is known as soft soap, as it produces more lather.
It is used as toilet soap and shaving soap.

Figure 3: general representation of soap molecule