SOAPS &

DETERGENTS

Lim Jia Yuan

5 Amanah
INTRODUCTION

1. Cleansing agents are chemical substance used to remove

grease and dirt.

2. There are two type of cleansing agents :

a) Soaps
b) Detergents

3. Soaps are sodium or potassium salt of fatty acids that

contains 12 to 18 carbon atoms per molecule.

4. Soaps are cleansing agents made from animal fats or

vegetable oil by saponification.

Soap is a salt of a compound known as a fatty acid. A soap

molecule consists of a long hydrocarbon chain (composed of
carbons and hydrogens) with a carboxylic acid group on one
end which is ionic bonded to a metal ion, usually a sodium or
potassium. The hydrocarbon end is nonpolar and is soluble in
nonpolar substances (such as fats and oils), and the ionic end
(the salt of a carboxylic acid) is soluble in water. The structure
of a soap molecule is represented below:
O
||
CH3-CH2-CH2- CH2-CH2-CH2-CH2- CH2-CH2- CH2-CH2- CH2-
CH2- CH2-CH2- C-O− Na+

Non-polar hydrocarbon chain ionic end.

(Soluble in nonpolar substances) (Soluble in water)

Detergents are structurally similar to soaps, but differ in the

water-soluble portion. Two examples of detergents are
shown below.
 sodium alkyl sulfate

sodium alkylbenzene sulfonate

SOAP

The History of Soap Manufacturing

There are records from the middle east that indicate people knew about soap
as far back as 4000 years ago. That stuff wasn't at all like the soap we're familiar
with now though. It was a gross mixture of oil and ashes. Apparently the cleaning
properties of this gross mixture was discovered in Rome at about 1000 BC.

According to the story, the animal fat from the animals that were sacrificed in
the fire to the Roman gods ran down the sides of the altar and mixed with the
ashes of the fire. In time this goopy mess found its way down to the banks of the
Tiber River where women would do laundry by pounding the dirt out with rocks.

What the women found was that dirt was easier to get out if the goopy junk
was applied to the fabric first. The first miracle cleaner had been discovered by
accident at a place near a hill called "Sapo". And so the Roman historian Pliny, gave
this "gross confection" the same name as the hill. In time "sapo" became our
modern word "soap". Romans only used soap in the laundry. They never used it on
the skin because it was crude stuff and it could damage the skin.

Soap is made by cooking fats and oils with toxic materials such as lye, caustic
soda or potash. In order for the result not to be well... disgusting, you must have
just the right amount of each ingredient. Too much of one raw material and the
soap is greasy and won't lather. Too much of another ingredient and the soap is
grainy and strong.

As with all things, people began to specialize in the manufacturing of soap. The
best soaps were known to come from the Castile region of Spain, where olive oil
instead of animal fat as used in the making of the soap. The wealthy classes in
Europe used Castile soap for hundreds of years.
Preparation of soap by saponification

1. Soap is a cleansing agents produced by the reaction between sodium

Hydroxide and potassium hydroxide with animal fats or vegetable oils. This
reaction is known as saponification.

2. Fats and vegetable oils are large, naturally occurring ester molecules.
When fats or oils are boiled with concentrated alkalis, such as sodium
hydroxide, saponification occurs and the ester molecules are broken down into
soap and glycerol.

Fats or vegetable oils + concentrated alkalis→ soap +glycerol

3. Saponification is the alkaline hydrolysis of ester using alkali solutions. From

the chemist aspect, soaps are sodium salts or potassium salts of long chain
carboxylic acids (with 12 to 18 carbon atoms per molecule).

4. Some examples of soaps are shown below.

a) Sodium palmitate, C15H31COONa
b) Sodium oleate, C17H33COONa
c) Sodium stearate, C17H35COONa

Additives such as perfume, colouring matter and sometimes antiseptics

are added to soaps to enhance their marketability.

5. Glyceryl tristearates are naturally occurring esters commonly found in

animal fats and vegetable oils. When the ester is boiled with concentrated
sodium hydroxide solution, saponification (alkaline hydrolysis) occurs and
mixture of sodium stearate (soap) and glycerol is obtained.

6. The soap produced can be precipitated by adding common salt

(sodiumchloride) to the reaction mixture.

7. The sodium chloride added reduced the solubility of soap in water. As a

result, precipitation of soap occurs.
8. The properties of soap depend on :
a) The type of alkali used for saponification
b) The type of animal fats or vegetable oils used.

9. Soaps produced from sodium hydroxide are hard, whereas soaps produced
from potassium hydroxide are soft.

10. Animal fats (tallow) from cows and vegetable oils (such as palm oil or olive
oil) are used for making soap.
The structure of soap molecule

1. When soap is dissolved in water, it will dissociate and produce sodium

ions and carboxylate ions (RCOO-). For example, sodium stearate
dissolves in water to form sodium ions and stearate ions.

C17H35COONa (s) + water→ C17H35COO- (aq)

sodium stearate stearate ions
+ Na+ (aq)

2. The active substance in soap is the carboxylate ion, for example,

stearate ion. The stearate ion consist of two parts : the ‘head’ and the
‘tail’. The ‘head’ id negatively charged and the ‘tail’ is a long hydrocarbon
chain.

3. The ‘head’ contains the -C-O- ions which dissolves readily in water
(hydrophilic) but does not dissolve in oil. Conversely, the ‘tail’ contains
a long hydrocarbon chain which is insoluble in water (hydrophobic) but
dissolves readily in oil.

4. Soaps made from palmitic acid are known as sodium palmitate.

(a) The molecular model of the palmitate ion.

 DETERGENTS

Modern detergents contain more than surfactants. Cleaning products may also
contain enzymes to degrade protein-based stains, bleaches to de-color stains and
add power to cleaning agents, and blue dyes to counter yellowing. Like soaps,
detergents have hydrophobic or water-hating molecular chains and hydrophilic or
water-loving components. The hydrophobic hydrocarbons are repelled by water, but
are attracted to oil and grease. The hydrophilic end of the same molecule means
that one end of the molecule will be attracted to water, while the other side is
binding to oil. Neither detergents nor soap accomplish anything except binding to
the soil until some mechanical energy or agitation is added into the equation.
Swishing the soapy water around allows the soap or detergent to pull the grime
away from clothes or dishes and into the larger pool of rinse water. Rinsing washes
the detergent and soil away. Warm or hot water melts fats and oils so that it is
easier for the soap or detergent to dissolve the soil and pull it away into the rinse
water. Detergents are similar to soap, but they are less likely to form films (soap
scum) and are not as affected by the presence of minerals in water (hard water).

Modern detergents may be made from petrochemicals or from oleochemicals

derived from plants and animals. Alkalis and oxidizing agents are also chemicals
found in detergents. Here's a look at the functions these molecules serve:

 Petrochemicals/Oleochemicals
These fats and oils are hydrocarbon chains which are attracted to the oily and
greasy grime.
 Oxidizers
Sulfur trioxide, ethylene oxide, and sulfuric acid are among the molecules used
to produce the hydrophilic component of surfactants. Oxidizers provide an
energy source for chemical reactions. These highly reactive compounds also act
as bleaches.
 Alkalis
Sodium and potassium hydroxide are used in detergents even as they are used
in soapmaking. They provide positively charged ions to promote chemical
reactions.
Preparation of detergents

1. The detergent, sodium alkyl sulphate can be prepared from alcohols

with chain lengths of 12 to 18 carbon atoms in two steps.

Steps 1: Reaction with concentrated sulphuric acid

Step 2: Neutralisation with sodium hydroxide solution.

2. An example of a long chain alcohol is didecan – 1 –ol,

CH3(CH2)10CH2OH. The detergent prepared from dodecan -1 –ol is
called sodium dodecyl sulphate (IUPAC name) or sodium lauryl sulphate
(common name).
CH3(CH2)10CH2O-SO3-Na+ .

3. Sodikum alkylbenzene sulphinates, were first used in 1940s. It can be

prepared in three steps. The starting materials for making this
detergents in a long chain alkene, RCH = CH2 , obtained from the
cracking of petroleum.
 a) Step 1 : Alkylation

Alkylation is the introduction of the alkyl group to an organic molecule

b) Step 2 : Sulphonation

Alkylbenzene produced the react with concentrated sulphuric acid acid to

form alkylbenzene sulphonic acid.

Sulphonation is the introduction of the sulphonic acid group, -SO3H to an

organic molecule to form sulphonic acid.

c) Step 3 : Neutralisation

Alkylbenzene sulphonic acid produced reacted with sodium hydroxide to

form sodium alkylbenzene sulphonate, the detergent
The structure of detergent molecule

This diagram shows the basic structure of a detergent molecule. Detergent

molecules have two distinct parts. There is a hydrophilic head, which is attracted
to water, and a hydrophobic tail, to which water has a very low attraction.
The cleansing of soap and detergent

The cleaning action of soap occurs when oil and grease are absorbed into the
hydrophobic centers of soap micelles and are washed away.

Cleansing action of soap

Sodium lauryl sulphate is a synthetic detergent present in laundry soaps,

toothpastes and shampoos. The formula of sodium lauryl sulphate is
CH3(CH2)11SO4- Na+. It has a hydrophilic sulphate group and a hydrophobic dodecyl
(C12H25) group. These detergent molecules are called 'anionics' because they have
negative charge at the hydrophilic end. There are detergents which are 'cationics'
that is they have positive charge at the hydrophilic end. For e.g.,

Many cationic detergents have germicidal properties and are therefore used in
hospital disinfectants, mouthwashes and certain eyewetting solutions
The effectiveness of soaps and
detergents as cleansing agents

Advantages of Detergents over Soap

Soaps  Detergents
 Detergents are sodium salt of long chain
 Soaps are sodium salts of higher
benzene sulphonic acid or the sodium salt
fatty acids
of a long chain alkyl hydrogen sulphate
 Calcium and magnesium salts of soap  Calcium and magnesium salts of detergents
anions are in soluble in water. are soluble in water. Therefore cleansing
Therefore cleansing action of soap action of detergents remain unaffected in
reduces in hard water hard water
 Soaps are prepared from natural oils  Synthetic detergents are prepared from
and fats hydrocarbons of petroleum