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Chapter IV: Soaps and Detergents

Fatty Acids
Fatty acids are organic acids with a carboxylic acid functional group and a with long
hydrocarbon chain.

Hydrocarbon chains of fatty acids can either be saturated or unsaturated

• Saturated fatty acids contain only single carbon-carbon bonds
• Unsaturated fatty acids contain double and/or triple bonds.

C=C bonds cause the fatty acid to have a ‘kink’ in its shape. This reduces the effective
area of contact between molecules, resulting in unsaturated fatty acids having lower
boiling points than their saturated counterparts.

What is Glycerol?
• Glycerol is an alcohol. It has three hydroxyl (alcohol) groups.

• Systematic name: 1,2,3-propantriol or propan-1,2,3-triol

• Glycerol is soluble in water as –OH groups are polar and therefore,

can form dipole-dipole forces as well as hydrogen bonds with water.

What are Triglycerides?

Triglycerides are large organic molecules that consist of three fatty acid molecules and a
glycerol molecule.

Triglycerides are formed from the esterification between glycerol (alcohol) and fatty acids
(carboxylic acid). Since a glycerol molecule has three alcohol groups, it will react with up
to three fatty acid molecules. Formation of triglycerides is a condensation reaction so
three H2O molecules are formed as biproducts.
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• Synthesis of triglyceride from fatty acids and glycerol is reversible. The reverse
reaction is the hydrolysis of triglyceride which produces glycerol and fatty acids

Saponification
Saponification (production of soaps) is the hydrolysis of triglycerides (fats) using a strong
base such as NaOH instead of water.

The presence of a strong base deprotonates what would have been fatty acid molecules
to form their conjugate bases (R–COO–). These conjugate base molecules form salts with
metal ions from the strong base e.g. Na+ This salt is soap.

Base-drive hydrolysis of triglycerides (saponification)

Water or acid-driven hydrolysis of triglycerides will produce glycerol (alcohol) and fatty
acids but will not form soap as protons of fatty acids remain in the molecules in the
absence of the base.

Hydrolysis of triglycerides using water

Producing Soaps in the Classroom

A sample experimental method for producing soap from olive oil is outlined below.
• Hydrolysis of olive oil (glyceryl trioleate) using NaOH:
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Method
1. Weigh 4.00 g of olive oil into a
150 mL beaker using an
electronic scale.
2. Add 10.0 mL of water, 1.00 g of
NaOH and 1.00 mL of ethanol to
the beaker.
3. Set up a water bath using a
tripod, wire gauze, 250 mL
beaker and Bunsen burner.
4. Heat the reaction mixture in the
water bath and stir the mixture
every five minutes.
5. Stop heating after the soap
forms. Carefully remove the
reaction beaker and allow it to
cool.
6. Dissolve about 18.0 g of NaCl in
50 mL of water. Add the salt
solution and stir. Spoon out the
curdles of soap into the folded
filter paper.
7. Set up a filtration apparatus. Use
the vacuum filtration apparatus to
further dry the soap curdles.
8. Wash the raw soap with water,
using a wash bottle. Spoon out
the rinsed soap onto a pad of
paper towels. Gently pat to
absorb excess water.

Note:
• 10 mL ethanol is added as a solvent to help dissolve the oil which is non-polar. The
polar part of ethanol will help create a miscible solution of oil and water.
• Dissolving NaOH in water is a highly exothermic process so the solution will become
quite hot.
• The use of a water bath or heating mantle will distribute heat more evenly to the
reaction mixture.
• After about 30 minutes of heating, the mixture will suddenly become creamy and then
start to curdle. This signals that soap has been made.

Structure of Soap
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• Soap has a long non-polar hydrocarbon ‘tail’.This part of the molecule

is hydrophobic (dislikes water). However, as it is non-polar it will be repelled away
from polar substances like water.
• The carboxylate (RCOO–) region of a soap molecule, or the ‘head’, is anionic. This
charged region is polar and readily dissolves in water, it is hydrophilic.

How do Soaps Work?

The action of soap can be better understood by examining their structures. Surface active
agents (surfactants) are chemical substances which decrease the surface tension of
water. This enables them to emulsify oils so that they can be suspended in water.
Cleaning agents such as soap are surfactants because their hydrophilic heads can
dissolve in water while their hydrophobic tails are embeded in the non-polar oil. This
interaction allows an emulsion to form between water and oil. An emulsion
is a stable mixture of two or more liquids that normally cannot be mixed.

Soap molecules help clean grease off surfaces via the following steps:
1. Non-polar hydrocarbon tails embed in grease particles, facing away from the water
(solvent) because they are hydrophobic.
2. Polar, charged hydrophilic carboxylate heads dissolve in water and increase the
attraction between water and grease particles.
3. When a grease particle is completely surrounded by soap molecules, a micelle is
formed. In a micelle, carboxylate heads face away from the grease particle and help
suspend the greasy particle in water to form an emulsion.

Properties of Soap
• Chain length of fatty acids determine the final properties of soap. As chain length
increases, it becomes less polar and therefore less soluble in water.
• Soap derived from long-chained fatty acids tend to be harder and do not lather as
easily as soaps derived from short-chained fatty acids.
o Coconut oil (short-chained) is commonly included as an ingredient in liquid soaps.
• Base used during triglyceride hydrolysis can affect soap properties
o Sodium-based soaps tend to be harder and less soluble in water
o Potassium-based soaps tend to be softer and more soluble in water
o KOH is typically used to make liquid soaps

Disadvantages of Soap
• Soaps are produced from biomass i.e. vegetable oil or animal fats therefore, they are
biodegradable
• Soaps cannot be used in acidic solutions: protonation of carboxylate head reduces its
hydrophilicity and ability to act as an emulsifier.
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• Soaps cannot be used in hard water (high concentration of Ca2+ and Mg2+ ions) as
they precipitate with the metal ions to form scum:

What are Detergents?

Detergents are synthetic compounds that mimic the action of soaps.
Disadvantages of soap led to the development of detergents. For example, detergents
can be used in acidic solutions and hard water.
The structures of detergents are similar to that of soaps in that they can be divided into
• hydrophilic heads
• hydrophobic tails

The chemical structure of hydrophilic heads determines the type of detergent.

Anionic Detergents
Anionic detergents are detergent molecules that contain negatively charged heads.

• Long, non-polar tail and an anionic head e.g. sulfate ion (R–SO4–)
• More effective than fat-derived soap as it creates more foam without compromising the
cleaning ability of the surfactant.
• Usually not used for personal hygiene as they would remove too much oil from skin
and hair.
• Typically found in laundry detergents and dishwashing liquids.

Cationic Detergents
Cationic detergents are detergent molecules that contain positively charged heads.

• Long, non-polar tail and a cationic head e.g. tertiary ammonium ion (R–N(CH3)3+)
• Used in plastic cleaners, hair conditioners and fabric softeners, disinfectants and
antiseptics.

Non-ionic Detergents
Non-ionic detergents are detergent molecules that do not contain an ionic charged head.
They usually contain heads that are partially charged.
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• Long, non-polar tail but a polar head that is not ionically charged. For example, alcohol
(hydroxyl) and/or ether (ethoxy) functional groups.
• Typically used in front-loading washing machines and dishwashers

Soaps vs Detergents
Similarities between Soaps and Detergents
• Soaps and detergents share similar structure as their structures consist of a
hydrophobic tail and a hydrophilic head.
• Soaps and detergents are both surfactants as their structures allow them to reduce
tension between oil and water by forming micelles.

Differences between Soaps and Detergents

• Hydrophilic heads vary between soaps and the three types of detergents.
• Detergents are synthetic whereas soaps are produced from biomass such as
vegetable oils and animal fats.
• Although both are cleaning agents, detergents and soaps have different uses. For
example, soaps are generally used for personal hygiene whereas detergents are used
in laundry, dishwashing and hard surfaces.

Advantages vs Disadvantages
• Detergents form more foam and have better cleaning action than soaps.
• Foam of synthetic detergents are less biodegradable and therefore, impose more
environmental implications.
• Soaps cannot be used in hard water as they form scum. This is not an issue with
detergents.
• Soaps cannot be used in acidic solutions as protonation of their ‘heads’ reduces their
hydrophilicity. This is not an issue with detergents.

Pertanyaan:
1. Jelaskan apa yang dimaksud dengan sabun?
2. Tuliskan persamaan reaksi penyabunan antara Gliseril Tripalmitat dengan NaOH.
3. Jika Gliseril Tripalmitat yang direaksikan 200 gram. Berapa:
a) Gram NaOH yang dibutuhkan
b) Gram Sabun yang terbentuk
4. Apa fungsi dari sabun?
5. Apa saja jenis jenis sabun?
6. Apa kelebihan sabun cair dibandingkan sabun padat?
7. Bahan kimia apa yang terkandung dalam deterjen?
8. Mengapa detergen lebih efektif untuk membersihkan kotoran apabila dibandingkan
dengan sabun?
9. Terdapat dua jenis bahan dasar pembuatan deterjen yaitu ABS dan LAS manakah
yang lebih ramah lingkungan mengapa jelaskan?
10. Tuliskan perbedaan antara sabun dan deterjen?
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