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Saponification

Saponification

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Published by Dotsha Raheem
Saponification, Preparation of Soap. Fats and Fatty acids
Saponification, Preparation of Soap. Fats and Fatty acids

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Categories:Types, Research
Published by: Dotsha Raheem on May 15, 2011
Copyright:Attribution Non-commercial

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05/06/2014

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University of Salahadin/ Colloege of Science
2011
Saponification
Dotsha J. Raheem 
 
 2
Saponification
 
Saponification
 Base catalyzed hydrolysis of an ester is known as Saponification, and the reaction product(the ionized salt) is soap.
RCOOR
Ester
NaOH
Hydrolysis
RCOO Na+ ROH
Salt Alcohol
 A fat consists of fatty acids and glycerin. Adding NaOH separates it to glycerin and the saltof the fatty acid.A fatty acid is acarboxylic acidwith a long unbranchedaliphatictail(chain), which is either saturatedorunsaturated.Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28.
R
1
COOCH
2
Fat or OilTriacylglycerol
NaOHR
1
COO Na+
Salt of fatty acidSoap
R
2
COOCHR
3
COOCH
2
Ester linkage
Saponification
R
2
COO NaR
3
COO NaOCH
2
OCHOCH
2
HHH
GleycerolGlycerin
 
Soaps are water soluble sodium or potassium salts of fatty acids (12C- 18C), and they aremade from fats and oils by treating them with strong alkali.If industrially produced fatty acids are used instead of natural fats and oils, the reactionwill yield soap and water instead of glycerin.
 
 3
Fats and fatty acids
The fats and oils used in soap making come from animal or plant sources. Fatty acids canbe attached to other molecules, as in triglycerides. When they are not attached to othermolecules they are
known as “free fatty acids”.
 Vegetable oil contain more unsaturated fatty acids (e.g. olive oil) while animal fatscontain more saturated fats (e.g. beef fat).
Acid Name StructureNo. of CatomsMeltingPointNo. of DoubleBonds
Lauric CH
3
(CH
2
)
10
COOH 12 +44 0Palmitic CH
3
(CH
2
)
14
COOH 16 +63 0Stearic CH
3
(CH
2
)
16
COOH 18 +70 0Oleic CH
3
(CH
2
)
7
CH=CH(CH
2
)
7
COOH 18 +16 1Linoleic CH
3
(CH
2
)
4
(CH=CHCH
2
)
2
(CH
2
)
6
COOH 18 -5 2Linolenic CH
3
CH
2
(CH=CHCH
2
)
3
(CH
2
)
6
COOH 18 -11 3Arachidonic CH
3
(CH
2
)
4
(CH=CHCH
2
)
4
(CH
2
)
2
COOH 20 -50 4The molecular structure allows many fatty acids tobe stacked together. As a result, close intermolecularinteractions result in relatively high melting points.The introduction of one or more double bonds in thehydrocarbon chain in unsaturated fatty acids results in
one or more “bends” in the molecule. The geometry of 
the double bond is almost always a
cis
configuration in
natural fatty acids. These molecules do not “stack”
very well. The intermolecular interactions are muchweaker than in saturated molecules. As a result, themelting points are much lower for unsaturated fattyacids.

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