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Saponification
Dotsha J. Raheem
2011
Saponification
Saponification
Base catalyzed hydrolysis of an ester is known as Saponification, and the reaction product
(the ionized salt) is soap.
O O
NaOH
R C O R R C O Na + R OH
Ester Hydrolysis Salt Alcohol
A fat consists of fatty acids and glycerin. Adding NaOH separates it to glycerin and the salt
of the fatty acid.
A fatty acid is a carboxylic acid with a long unbranched aliphatic tail (chain), which is either
saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even
number of carbon atoms, from 4 to 28.
O O
R1 C O CH2 R1 C O Na H O CH2
O NaOH
R2 C O CH Saponification O + H O CH
O R2 C O Na
R3 C O CH2 H O CH2
O
R3 C O Na
Ester linkage Salt of fatty acid
Fat or Oil Gleycerol
Triacylglycerol Soap Glycerin
Soaps are water soluble sodium or potassium salts of fatty acids (12C- 18C), and they are
made from fats and oils by treating them with strong alkali.
If industrially produced fatty acids are used instead of natural fats and oils, the reaction
will yield soap and water instead of glycerin.
2
Fats and fatty acids
The fats and oils used in soap making come from animal or plant sources. Fatty acids can
be attached to other molecules, as in triglycerides. When they are not attached to other
molecules they are known as “free fatty acids”.
Vegetable oil contain more unsaturated fatty acids (e.g. olive oil) while animal fats
contain more saturated fats (e.g. beef fat).
No. of
No. of C Melting
Acid Name Structure Double
atoms Point
Bonds
Lauric CH3(CH2)10COOH 12 +44 0
Palmitic CH3(CH2)14COOH 16 +63 0
Stearic CH3(CH2)16COOH 18 +70 0
Oleic CH3(CH2)7CH=CH(CH2)7COOH 18 +16 1
Linoleic CH3(CH2)4(CH=CHCH2)2(CH2)6COOH 18 -5 2
Linolenic CH3CH2(CH=CHCH2)3(CH2)6COOH 18 -11 3
Arachidonic CH3(CH2)4(CH=CHCH2)4(CH2)2COOH 20 -50 4
3
Fatty acids are divided into short, medium or long chain
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How soap cleans
Although the sodium and potassium salts of common soaps are soluble in water, the
metal cations Mg2+, Ca2+ and Fe3+, which are typical components of “hard” water, form
insoluble complexes. It also leaves a hard scum on the surface of sinks and tubs.
O
CH3 (CH2)16 C O Na+
sodium stearate
Ca 2+
O O
2+
CH3 (CH2)16 C O Ca O C (CH2)16 CH3
calcium stearate
Most detergents, however, do not respond in a similar manner, and can be used in both
“hard” and “soft” water.
5
O O
+ +
CH3 (CH2)11 O S O Na CH3 (CH2)11 S O Na
O O
sodium n-dodecyl sulfate (detergent) sodium n-dodecyl benzene sulfonate (detergent)
Types of soaps
The properties of the soap depend upon the type of the fat or oil used, including number
of carbons in the chain and the degree of unsaturation in the fatty acid, and the metal ion:
soaps made from KOH have softer consistency than soaps made from NaOH.
Procedure: