Unit-III

Topic: Fats & Oils

Class: B. Pharm. III Sem
Sub: Organic Chemistry-II
Class No.: 3
Presented By
Bibhas Pandit (Subject In-Charge)
Fats & Oils
Summery of the previous class

Physical Properties of Fats and Oils

1. Colourless, odourless and tasteless.
2. Insoluble in water.
3. Specific gravity is less than 1.0, consequently all fats float in water.
4. Oils are liquids at 20°C, they contain higher proportion of Unsaturated
fatty acids.
5. Fats are solid at room temperature and contain saturated long chain fatty
acids
Fats & Oils
Chemical Properties of Fatty acid
Fats & Oils
Reactions of Fats and Oils
1. Hydrolysis: Triglycerides are easily hydrolysed by enzymes called lipases
(catalysts) in the digestive tracts of animals to give fatty acids and glycerol.
The fatty acids so produced play an important role in the metabolic process
in the animal body.

O O

H2C O C R1 H2C OH HO C R1
O O
Hydrolysis
HC O C R2 + 3H2O HC OH + HO C R2
O O

H2C O C R3 H2C OH HO C R3

Fats/Oils Glycerol Fatty acids

Fats & Oils
Reactions of Fats and Oils
2. Saponification: When triglycerides are hydrolysed (saponified) by alkalis, glycerol
plus the salts of fatty acids are produced. Generally the sodium or potassium salts
are obtained which are termed soaps. Saponification: When triglycerides are
hydrolysed (saponified) by alkalis, glycerol plus the salts of fatty acids are produced.
Generally the sodium or potassium salts are obtained which are termed soaps.
Fats & Oils
Reactions of Fats and Oils
3. Hydrogenation: Unsaturated glycerides react with hydrogen in the presence
of a metal catalyst (usually nickel) to give saturated glycerides. This reaction in
similar to the catalytic hydrgenation of alkenes. Here, the hydrogenation
process saturates the double bonds present in the fatty acid components of the
glyceride; thereby converting them to saturated acid components. The result is
the transformation of a liquid glyceride
O O

H2C O C (CH2)7 C C (CH2)7 CH3 H2C O C C17H33

H H
O O
H2/Ni
HC O C (CH2)7 C C (CH2)7 CH3 HC O C C17H33
O H H
O

H2C O C (CH2)7 C C (CH2)7 CH3 H2C O C C17H33

H H

Glyceryl trioleate Glyceryl tristearate

Fats & Oils
Reactions of Fats and Oils
4. Halogenation: Unsaturated Fats or oil have capability to adding halogen
Degree of unsaturation is determined by this halogenations. E.g. Iodine value
O

H2C O C (CH2)7 C C (CH2)7 CH3

H H
O

HC O C (CH2)7 C C (CH2)7 CH3

O H H
3I2
H2C O C (CH2)7 C C (CH2)7 CH3
H H

Glyceryl trioleate O I
I

H2C O C (CH2)7 C C (CH2)7 CH3

H H
O I I
HC O C (CH2)7 C C (CH2)7 CH3
O H H
I I
H2C O C (CH2)7 C C (CH2)7 CH3
H H
Glyceryl-hexaiodatetristearate
Fats & Oils
Reactions of Fats and Oils
5. "Drying" of Oils:
 The methylene groups flanked by doubly bonded carbon atoms present in
highly uasaturatcd glycerides are very reactive.
 Linseed oil, the most widely used drying oil, contains about 63 per cent of
its fatty acids as linoleates.
 The CH, group present in linoleic acid component of the unsaturated
glyceride is readily attacked by oxygen of the air to form hydroperoxy
group (—O--O-----H) at these sites.
 These hydroperoxy groups then react with unchanged CH, groups in other
glyceride molecules to form peroxide bridges.
 The hydroperoxide formation accompanied by polymerisation converts
polyunsaturated glycerides into a vast network of interlinked units.
 Such a network forms a dry, tough and durable film when exposed to air.
Fats & Oils
O Active methylene group
Reactions of Fats and Oils
H2
H2C O C (CH2)7 C C C C C (CH2)4 CH3
"Drying" of Oils: H H H H
O Linoleate f ragment
H2
HC O C (CH2)7 C C C C C (CH2)4 CH3
O H H H H
H2
H2C O C (CH2)7 C C C C C (CH2)4 CH3
H H H H
O2
From air
O
H
H2C O C (CH2)7 C C C C C (CH2)4 CH3
H H H H
Linoleate O O H
Polymerization Hydroperoxide
O
H
H2C O C (CH2)7 C C C C C (CH2)4 CH3
H H H H
O O
O Cross linked unit in a drying oil
HC O C (CH2)7 C C C C (CH2)4 CH3
O H H O H
O
H2C O C (CH2)7 C C C C C (CH2)4 CH3
H H H H H
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Reactions of Fats and Oils
6. Rancidity: The term rancid is applied to any fat or oil that develops a
disagreeable odour when left exposed to warm, moist air for any length of time.
Rancidity is by hydrolysis of the ester links and oxidation of double bonds of the
triglycerides. The lower molecular weight acids that are produced are volatile and
impart an offensive odour to fat or oil.

O O

H2C O C R1 H2C OH HO C R1
O O
Lipase or Acid
HC O C R2 + 3H2O HC OH + HO C R2
O O

H2C O C R3 H2C OH HO C R3
Hydrolytic rancidity
Fats/Oils Glycerol Fatty acids
Fats & Oils
Reactions of Fats and Oils
Oxidative Rancidity: During oxidation, oxygen is added to the unsaturated
linkage and this result in the formation of peroxides. These
peroxides decompose to yield aldehyde and ketones which are responsible
for the pronounced flavour.
Fats & Oils
Harmful effects of lipid perioxidation:
1. Damage to cell membrane
2. Cardiovascular diseases
3. Joint disease
4. Aging
5. Cancer
Fats & Oils
Method for analysis of fats and oils
1. Determination of Moisture Content
2. Determination of Specific Gravity
3. Determination of Refractive Index
4. Determination of Saponification Value
5. Determination of Acid Value
6. Determination of Iodine Value
7. Determination of Reichert Meissl and Polenske value
8. Acetyl value
Fats & Oils
Method for analysis of fats and oils
1. Determination of Moisture Content
2. Determination of Specific Gravity
3. Determination of Refractive Index
4. Determination of Saponification Value
5. Determination of Acid Value
6. Determination of Iodine Value
7. Determination of Reichert Meissl and Polenske value
8. Acetyl value
Fats & Oils
Method for analysis of fats and oils
Fats & Oils
Method for analysis of fats and oils