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3 - Chemical Reactions of Fat and Oils

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CHEMICAL

REACTIONS
OF FATS &
OILS
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CHEMICAL REACTIONS OF
FATS & OILS
Oxidation
Hydrolysis
Polymerization
Ester formation
Reactions during heating
and cooking/frying
Online lecture
http://www.youtube.com/watch?feature=player_em
bedded&v=nyz9tI-fCUw
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Hydrolysis/ Lipolysis
Hydrolysis of ester bonds in lipids (lipolysis)
may occur by enzyme action (e.g., lipase) or
by heat/moisture free fatty acids (FFA)
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Hydrolysis/ Lipolysis

Accelerated by high T, P & water, e.g., in


deep-frying of fresh potatoes (~80%
moisture) liberation of excessive FFA may
result in excessive smoking (reduce smoke
point of the oil) (1 3% FFA is tolerable)
FFA is more susceptible to oxidation than FA
esterified to glycerol.
Short chain FA is responsible for undesirable
rancid flavour (hydrolytic rancidity) in milk.
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Hydrolysis/ Lipolysis
Controlled/selective lipolysis is used deliberately to
develop cheese flavour (ripening) & certain food,
e.g., yogurt.
FFA is always present in crude oil (e.g., 3-5% in
palm oil) remove during refining (by alkali
neutralisation/steam distillation)
Complete hydrolysis of fats is applied on a large
scale for the production of fatty acids for the soap
& oleochemical industries.

Triglyceride + Water heat Glycerol + 3 FFA


Oxidation
Oxidation reaction of an oil/fat (at the double
bond) with oxygen in the air adversely affect the
flavour of the fat/food oxidative rancidity.
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Oxidation

Autoxidation oxidation induced by air at


room temperature radical chain process.
Products containing fat with a higher
proportion of unsaturated fatty acids are
more prone to oxidation.
Rate of oxidation with T, O2, presence of
light & contact with pro-oxidants (e.g. copper)
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Polymerization
Reaction whereby small molecules of oil/fat
combine to form much larger molecules.
This may occur at points of unsaturation on fatty
acid chains (preceded by oxidation) or at the
ester bond.
Can occur in deep frying of foods accelerated
by frying at too high a T (> 177 C) in the
presence of O2.
Polymerisation also causes viscosity & if
allowed to proceed can result in foaming of the
frying oil.
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Deep frying a process of cooking involving the


direct heat transfer of heat from oil to cold food
Applications: frying of french fried potatoes,
seafoods, poultry, doughnuts, etc.
Food placed in hot oil is heated quickly to the
point where water is vaporised the resulting
steam causes a boiling action in the oil;
this boiling action aeration in the oil
oxidation with the formation of
hydroperoxides
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Changes in oil during frying (cont.)


The peroxides (being very unstable) decompose
via fission, dehydration & formation of free
radicals to form a variety of volatiles (VDP) &
nonvolatile decomposition products (NVDP).
The VDP are constantly being removed by the
evolving steam.
The NVDP (polymers, dimers, trimers) are mainly
formed via oxidation reactions removed from the
frying oil via absorption by the food being fried/by
deposition on frying kettle part/filtration.
Solubilisation of components from food being fried
e.g., coloured compounds
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Changes/Reactions During Deep Frying


1. Darkening of the frying oil protein accelerates colour
darkening > starch; breadings high in reducing sugars
darkening
2. Oxidation - as frying T ; presence of prooxidants
(Fe & Cu); presence of antioxidants (e.g. BHA/BHT)
minimise oxidation.
3. Polymerisation can cause foaming, gumming
(methyl silicone at 0.5 2 ppm can reduce foaming)
4. Hydrolysis/development of free fatty acids rate of
hydrolysis increases with more water in food, higher
frying T, slower turnover (replacement with fresh oil) &
food loading (amount of food being fried).
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FFA Development During Deep Frying

High potato
rate
% Free Fatty Acids

Low potato
rate
zero rate

Hours of frying
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Foam Development During Deep Frying

Low potato rate


zero rate
% Foam Height

High potato
rate

Hours of frying
Changes during deep-fat frying
Steam, volatiles, antioxidants

AERATION ABSORPTION VAPORIZATION

oxygen steam
FOOD
OXIDATION HYDROLYSIS
SOLUBILIZATION FFA, diglycerides,
hydroperoxides
(conjugated dienes) glycerine,
colored compounds
monoglycerides

FISSION DEHYDRATION FREE RADICALS

alcohols ketones dimers,trimers,


epoxides, alcohols,
aldehydes
hydrocarbons
acids hydrocarbons
HEATING dimers, cyclic compounds
Changes/Reactions During Deep Frying

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