Chemistry of Fats Oils and Waxes

CHEMISTRY OF
FATS, OILS,
AND WAXES
Centeno, Kathryn
Decembrano, Katrin Mae

Ramiscal, Michael Gabriel
Lipids
Lipids are a class of biological
molecules defined by low solubility in
water and high solubility in nonpolar
solvents.
Role of Lipids
1. They store energy and protect and insulate
internal organs. In human bodies they are
stored as fat cells and in animal bodies as
starch.
2. They are found in nerve fibers and hormones as
steroids, which act as chemical messengers.
3. Because they are not soluble in water, a major
function of lipids is to build the cell membranes
that separate the internal contents of cells from
the surrounding aqueous environment.
Classification of Lipids
1. Triglycerides
- derived from glycerol and three fatty acids
2. Phospholipids
- contains glycerol and two fatty acids
3. Steroid
- composed of four fused rings of carbon
where functional groups are attached
4. Waxes
-organic compounds that characteristically
consist of long alkyl chains.
Fatty Acids
A fatty acid contains a long chain
attached to carboxylic acid
group at one end.
Normally, fatty acid contains an
even number of carbon atoms,
usually between 12 and 20.
They are insoluble in water
because the size of the
nonpolar portion is bigger than
the size of polar portion
(carboxyl group). They form
micelle in water.
Types of Fatty Acids

1. Saturated Fatty Acids
no C=C bonds
2. Unsaturated Fatty Acids
a. Monounsaturated
one C=C bond
b. Polyunsaturated
two or more C=C bond
c. Cis/Trans
Saturated Fatty Acids

Generally found in animal, palm, cocoa and
coconut and the foods made from them.
Single carbon-carbon bonds.
General formula CnH2n+1 COOH
Certain fatty acids are already 'naturally saturated'
in that they cannot be made 'harder' than they
are in nature.
Saturated fatty acids are extremely stable i.e. they
do not easily become rancid, meaning they have
good keeping properties (shelf life).
Unsaturated Fatty Acids

Generally found in plant and fish and the
foods made from them.
Carboxylic acids
Stability depends on the number of C=C
bonds. Carbon double bonds are highly
reactive making it unstable. As the
amount of unsaturation increases the
stability decreases.
Unsaturated Fatty Acids

Classifications:
1. Mono-unsaturated fat contains fatty acids with 1 C=C
double bond. Ex: olive, canola and peanut oils.
2. Poly-unsaturated fat contains fatty acids with 2 or more
C=C double bonds. E.g. safflower, sunflower, corn, fish oils).
3. Cis and Trans Fat
a. Cis Unsaturated Fat - H atoms on the same side of the double
bond. have lower melting points than trans fats since this
configuration causes more kinking of the chain. The
molecules are not as closely packed, decreasing the strength of
the van der Waals forces between them.
b. Trans Fat - H atoms on opposite sides of the C=C double
bond. Occurs in processed unsaturated fats commonly through
hydrogenation process
Fats and Oils

Fats and oils are made through esterification, a
reaction in which the hydroxyl groups of glycerol
form ester bonds with the carboxyl groups of fatty
acids. It is the reaction between glycerol and three
fatty acids to produce triglycerides (fat) and water.
Reactions Triglycerides
Undergo
1. Hydrolysis important for fat and oil digestion.
Triglycerides are hydrolysed (split by water) in the
presence of strong acids or digestive enzymes called
lipases. The products of hydrolysis of the ester
bonds are glycerol and three fatty acids.
Reactions Triglycerides
Undergo
Hydrogenation - converts carbon-carbon double bonds to single
bonds. The hydrogen gas bubbled through the heated oil
the presence of a nickel catalyst (or another transition
metal).
3. Oxidative Rancidity - Results in the formation of a small

carboxylic acid and an aldehyde. - Responsible for the foul
odor associated with fat decomposition
Triglyceride + O2 Small organic molecules
Fats
Generally crystalline solids at room

temperature.
Contains more saturated fatty acids
As the length of the fatty acid chain
increases the number of atoms and
number of electrons increases. The
strength of the Van der Waals forces
between the fat molecules increases,
increasing the melting point.
Ex: butter, cheese
Oils
Generally liquids at room temperature.
Contains more unsaturated fatty acids. The double
bond in unsaturated fatty acids produces a kink
in the chain which means that the fat molecules
can not pack closely together. As the number of
C=C double bonds increases the amount of
kinking increases and the distance between the fat
molecules increases. This decreases the strength
of the Van der Waals forces between the
molecules, decreasing the melting point.
Waxes
The word "wax" is derived from the old
English "weax" for the honeycomb of the
bee-hive. Thus, bee wax can be
considered as the reference wax.
Wax is the water resistant protective
coatings of leaves, fruits, and trees,
also in animals, algae, fungi and bacteria.
Wax is hydrophobic in nature produced by
combining fatty acids with alcohols.
All waxes are water-resistant materials made up of various substances
includinghydrocarbons (normal or branched alkanes and alkenes), ketones,
diketones, primary and secondary alcohols, aldehydes, sterol esters,
alkanoic acids,terpenes (squalene) and monoesters (wax esters), all with
long or very long carbon chains (from 12 up to about 38 carbon atoms) and
solid in a large range of temperature (fusion point between 60 and 100C).
They are soluble in aromatic solvents, chloroform, ethers, esters and ketones.

Chemistry of Fats Oils and Waxes

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Chemistry of Fats Oils and Waxes

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CHEMISTRY OF

Decembrano, Katrin Mae

Types of Fatty Acids

Saturated Fatty Acids

Unsaturated Fatty Acids

Unsaturated Fatty Acids

Fats and Oils

3. Oxidative Rancidity - Results in the formation of a small

Generally crystalline solids at room

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