Chapter 14

soaps
 Introduction
• Soaps were used more for medicine, however since the 19 th
century , soaps became an essential cleaning or bleaching
products.
• They prevent against the development of microbes and
parasites where one of the cheapest, easiest, and most
important ways to prevent the spread of a virus ( example
coronavirus) is to wash your hands frequently with soap and
water
Outline
I-Preparation of soap
Row material
1-Glycerol
2-Fatty acids
3-Triglycerides
II- Saponification reaction
III-Solubility of soap
IV-Principle of Detergency:
V- Laboratory Preparation of the soap
 I- Preparation of soap

• The reaction of preparation of soap is called

Saponification reaction
• Saponification reaction equation:
Fats/oils + strong base  soap + alcohol

Triglycerides NaOH Glycerol

Triesters OR KOH Trialocohol
 I- Preparation of soap

hydroxide
Potassium hydroxide

Sodium

NaOH
KOH
Oil / fat (ester) + strong base (hydroxide ion HO-) soap + glycerol
Oil: triglyceride of plant origin; soya oil, olive oil…
BASE
Fat: triglyceride of animal origin; beefs, sheep, cows….
Hard Soap

Soap
Soft
A- Triglycerides:
They are the major components of fats and oils

They belong to the family of Ester

These are triesters that can be obtained from esterification

reaction that occurs between fatty acids and glycerol
Fatty acids + glycerol Ester + Water

They have a general formula :

R1, R2, R3 could be same or different .
 R
B-Fatty Acids:
Saturated
hydrocarbon

They belong to the family of carboxylic acids.

chain

Unsaturated
hydrocarbon
chain
They are carboxylic acids (monoacids) that have a linear long carbon
chain with an even number of carbon atoms ( 4 ≤ number of C atoms ≤
22) .
They have general formula:
R - COOH

hydrocarbon chain(alkyl group) carboxyl group

B-Fatty Acids:
Each fatty acid is symbolized by 2 numbers (X;Y)
( X= number of C atoms ; Y= degree of unsaturation or number of
double covalent bonds)
Ex: Lauric acid (12 ; 0) : CH3 (CH2)10 COOH

Stearic acid (18 ; 0) : CH3 (CH2)16 COOH

Oleic acid (18 ; 1) , and the double bond is between C-9 and C-10 :

CH3 (CH2)7 CH CH (CH2)7 COOH

C- Glycerol:
It belongs to the family of Alcohols.

It is obtained as a by product from Saponification

reaction .

It is used as a moisturizer for skin

It has a general formula :

C- Glycerol:
CH2 CH CH 2 or CH2 OH : systematic name : 1,2,3 -propantriol

OH OH OH CH OH

CH2 OH
Primary alcohol

Secondary alcohol
D- Triglycerides:
They are triesters produced by the estrification of fatty acids and glycerol:

R1 COOH + CH2 OH R1 COO CH 2

R2 COOH CH OH R2 COO CH + 3H 2O
R3 COOH CH2 OH R3 COO CH2
R1 ,R2 and R3 could be the same or different
Characteristics
- Athermic
- Reversible
- Slow
 II-Saponifiction Reaction
Soaps are salts of sodium or potassium carboxylates (RCOO -,Na+ or K+)
Oil / fat (ester) + strong base (hydroxide ion HO-) soap + glycerol

-Name of reaction: Saponification Reaction

-Type of reaction: Hydrolysis Of Ester In Basic Medium.

- Characteristics: The saponification reaction is slow but complete and it takes place at high
temeperature.
( Heating the reaction as a kinetic factor to 80 oC to increase its rate)
 Nomenclature
Name of the Fatty Name of the Name of the Soap
acids R-COOH Triglycerides R-COO-,Na+
(carboxylic acid) Carboxylic acid
in Sodium carboxylate
Oleic acid Olein Sodium oleate
Stearic acid Stearin Sodium stearate
Lauric acid Laurin Sodium laurate
Palmitic acid Palmitin Sodium palmitin
 III-Solubility of Soaps
1-In pure water:
Soap is not highly soluble(moderately) in water. It dissolves in water according to
the equation:
.

RCOONa H 2O RCOO- + Na+

RCOO- reacts with water to give HO- ions that make the medium basic (pH of soap solution>7)

RCOO- + H2 O RCOOH + HO-

 2-In hard water:
Definition: Hard water contains a relatively high quantity of metallic ions like :
Ca2+ ; Mg2+ ; Fe2+ ; Fe3+ ; Al3+….
It leads to the formation of different metallic carboxylates precipitate showed that
soaps are not soluble in hard water.
This will diminishes the detergency action of soap.
To solve this problem, softeners are added to prevent the action of these ions.
- + 2+ +
2(RCOO- + Na+ ) + Ca2+
2(RCOO + Na ) + Ca (RCOO) Ca +
(RCOO)2Ca(s) + 2Na
2 (s) 2Na
+ : whiteprecipitate
: white precipitate
- + 2+ +
2(RCOO- + Na+ ) + Mg2+
2(RCOO + Na ) + Mg (RCOO) Mg +
(RCOO)2Mg(s) + 2Na
2 (s) 2Na
+ : whiteprecipitate
: white precipitate
Solubility of soap in water
3-In salty water (NaCl solution) :
Na+ ions is a common ion between the salty water and soap solution.
Soaps are insoluble in solutions that contain sodium ion Na+ due to the common ion effect.

Salty water increases the concentration of Na+, so the system is going to decrease
this concentration, by moving in the direction(2) which is the direction of
precipitation of soap.

Rk: This property will be used in the preparation of soap. At the end of the reaction,
some salty water (concentrated solution of sodium chloride) is added to precipitate all
soap formed to separate soap from glycerol. This process is called “ Flocculation”.
4 -In acidic medium:
In acidic medium soap precipitate as a fatty acid according to the following reaction:

RCOO- + H3O+ RCOOH + H2O

So soaps are not suitable to use for washing in acidic medium.

Solubility decreases  detergency decreases too.

 IV-Principle of Detergency:
A detergent is a substance which when dissolved in water, it confers to water the capacity to clean the
surface from stain. Detergent is a product that removes dirt (greasy substances) that adhere to a
substrate.
Soaps are a detergent. The anion part carboxylates ions (R-COO-) will be responsible of
cleaning part ( detergency)

The general formula of soap is :

R – C O O - . Na+

Anion part comes Cation part

from fatty acids comes from
strong base
 IV-Principle of Detergency:
The anion part of soap R-COO- has a negative charge at one end and a long hydrocarbon chain at the other end of
represented as :
R - COO -

Tail Head

Is insoluble in water Is soluble in water

Its called Its called hydrophilic

hydrophobic (water (water loving) and
fearing) or lipophilic lipophobic (fat fearing)
(fat loving )
 IV-Principle of Detergency:
RCOO- is called amphiphilic since it has hydrophilic and hydrophobic properties or
lipophilic and lipophobic properties.
These properties are the cause for the solubility of soaps in water and their detergent
property.
 Formation of micelles
When sodium soaps are mixed with water, micelles are formed . The micelles are made
up of an agglomeration of some tens to 100 R-COO-, The hydrophilic part (head)
pointed toward the outside because it is attracted to water molecules, wheresas the tail
(hydrophobic part) is pointed toward the inside.
The head is the hydrophilic
part of the RCOO- ion , it loves
water. So this part must be
immersed in the water.

On the other hand, the tail is

hydrophobic part , so it hates
water and arranges outside
water.

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 How does soap clean?
Most dirts sticks to clothes and body parts by thin film of oil.

When we soak a dirty piece of tissue in water containing soap , or when we wash
our hands with soap and water, large number of RCOO-s surround the oil with the
hydrophobic part which is fat loving(lipophilic), while the hydrophilic end dissolving in
the water.

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 When more water is added, and after shaking the dirt is detached
from the clothes in a spherical shape called micelle.

then the micelles are washed away thus getting red of the dirt and
leave the surface clean.

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December 8, 2023 Arabsalim HighSchool prepared by: T. Fatima Fahs
December 8, 2023 Arabsalim HighSchool prepared by: T. Fatima Fahs
 V- Preparation of the soap
Step 1- Chemical reaction
In a round bottom flask , we mix :
- volume V of a solution of NaOH
- volume V 'of oil (triglyceride)
-volume V''of ethanol
Then we fix the flask on a heating mantle and
adjust the condenser to the setup and heat for 30
minutes

Why do we add ethanol?

The oil and the water are not miscible, ethanol is miscible
with water on one side and dissolves oil on the other side, so
the ethanol increases the contact area between the aqueous
NaOH solution and the oil so the rate of the reaction
increases
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 Heating under reflux
Saponification reactions are is slow so heating is
often used to increase the rate of reaction.

However, many organic compounds have low

boiling points and will vaporize upon exposure to
such high heat, preventing the reaction from
proceeding in full.

To address this, heating under reflux is used.

The reflux is preventing to lose the components of
the reaction by condensing their vapors escaping
and returning them to the reactional mixture in the
flask and thus the mass of reactants and products is
conserved.
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Step 2-Relargage( flocculation):
Add a concentrated solution of sodium chloride (brine solution):
It promotes the precipitation and separation of soap from the glycerol
and other soluble ions present in the medium:
R-COONa (s) RCOO- aq + Na+ aq
It promotes the floatation of a solid soap that is
separated by filtration. All other substances remain in
the solution.

Species present in Solution

- Water
- Glycerol
- Ethanol
- Na+, HO- , Cl-

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Step 3- Filtration
This process can be accelerated using vacuum filtration:

December 8, 2023 Arabsalim HighSchool prepared by: T. Fatima Fahs

December 8, 2023 Arabsalim HighSchool prepared by: T. Fatima Fahs