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Mihret

Measuring the Degree of Unsaturation in Fats and Oils

Introduction
The fats and oils we consume everyday are, on the molecular level, made up of triglycerides. More
broadly, these are ester compounds; organic substances derived from a reaction between an acid (usually
carboxylic acid) and an alcohol. Triglycerides are made up of three fatty acid chains with a glycerol
compound bonded at the end of the chains. The fatty acids themselves are usually classified into two
species; which are unsaturated and saturated fatty acids. These names simply refer to the presence of
double bonds among the carbon atoms. If there are any double bonds, the fatty acid is called unsaturated,
while when no double bond is present, it is referred to as saturated.
Now, while an individual fatty acid may be unsaturated, this does not necessarily mean that the
whole chain of carbon atoms manifests double bonds rather than single ones. In a whole fatty acid chain,
there is variation in the type of bond the various carbon atoms manifest. This is important because out of
this variation arises grades of saturation or unsaturation. We can say that one fat is more unsaturated
than the other because different fats have differing numbers of double bonds. A property that immediately
rises out of unsaturation (double bond) is higher reactivity. The double bonds exhibited between some
carbon atoms consists of one strong bond where the electrons are found half-way between the two nuclei,
and a weak one where the electrons are further away from the two nuclei. Therefore, it becomes easier for
electrophilic reagents to take over the weakly bonding electrons.1
On the macro-level, these molecular characteristics (presence and concentration of double bonds
or single bonds) naturally produce certain sensible characteristics. Such as differences in color during
reactions or higher and lower melting points depending on the degree of saturation/unsaturation. For
example, when an unsaturated oil or fat reacts with acidified potassium permanganate in a hexane
solution, the substance produced exhibits a dark pinkish to purplish color. There is a gradual change
towards this color as the reaction takes place, and eventually there is a plateau. From this we can see that
if we ever want to find out the differences in unsaturation levels between different lipids, a simple
qualitative comparison after a reaction such as the one just mentioned will do. Taking various fats and oils
and putting them under that reaction with a gradual addition of the reagent (KMnO4) will result in
varying degrees of color-change rates. Presuming that all the fats in this hypothetical experiment are
unsaturated, if one fat has a higher concentration of double bonds than the other, in the presence of
KMnO4, it will have more weak bonds for the electrophiles to react with. This is the whole theory behind
this lab experiment; checking for the degree of unsaturation by looking at the rate of the reaction through
an observation of the color change and the plateau it ultimately hits when the product has been
completely produced.

1 Socratic.org, (2016). Why does the double bond in alkenes make them more reactive than alkanes,
which are single-bonded?. [online] Available at: http://socratic.org/questions/why-does-the-doublebond-in-alkenes-make-them-more-reactive-than-alkanes-which-a [Accessed 7 Jan. 2016].

Mihret

Measuring the Degree of Unsaturation in Fats and Oils

Aim
The aim of the experiment was to measure the degree of unsaturation in various oils and fats by
comparing the rate of the reactions through a look at the rate at which the qualitative end products (in
this case the color dark pink/purple) appeared after reacting with a KMn
Hypothesis
According to NutriStrategy.com, these are the unsaturation percentages of the following fats, which we
used in our lab experiment:

Corn Oil: 83%


Canola Oil: 88%
Butter : 33%
Margarine: Margarine usually has less than half the saturated fat of butter2
(i.e. Margarine < 16.5%)

Given these, it is obvious that all of them will eventually produce the expected sensible results (a color
change that will eventually plateau at dark pink/purple). But the question is: in what chronology? Which
fat/oil will hit the plateau the quickest and which the slowest? But there is also another problem; the
percentages given above dont necessarily apply to every individual corn oil, butter, margarine and so on.
On the contrary, there unsaturation levels may have been altered prior to the experiment in routine
processes such as those of the industry. For example, oils like margarine can be made more saturated (i.e.
less double bonds) by adding hydrogen (hydrogenation). It is hugely important and widely used in the
food industry where, for example H2 molecules are added to unsaturated vegetable oils and fats. 3
Therefore, it is possible that there are considerable differences between the unsaturation levels of the
lipids used in our experiment and the typical levels reported by health organizations. And thus it becomes
more difficult to predict the results.
Regardless, assuming that the unsaturation levels in our experiment are relatively similar to those
given above, canola oil will have the quickest reaction rate (i.e. reaches color-change plateau quickest).
Corn oil will come in second, although because the differences between canola and corn unsaturation
levels are so little, it requires more precision and thorough observation to notice any color differences
between the two under the same controlled conditions. Butter and margarine will, on the other hand, have

2Corporation, Australian. 2008. "Butter or Margarine: Which Is Better When It Comes To Fat? - Health &
Wellbeing". Abc.Net.Au.
http://www.abc.net.au/health/talkinghealth/factbuster/stories/2008/08/06/2323118.htm.
3 Controlengeurope.com,. 2016. "Hydrogenation in The Food Industry".
http://www.controlengeurope.com/article/30066/Hydrogenation-in-the-food-industry.aspx.

Mihret

Measuring the Degree of Unsaturation in Fats and Oils

a much slower color-change. Between these two, butter will come in third in reaching the color-plateau at
a distinguishable rate since margarine has less than half the saturated fat of butter.

Variables

Controlled: Organic solvent (Hexane), Amount of Hexane, Amount of Fat/Oil, Amount of

KMNO4 added at each stage


Independent: Degree of Unsaturation (Number of Double Bonds)
Dependent: Rate at which color reached ultimate end (plateau at dark pink/dark purple color)

Results
Butter

Amount of KMnO4 (ml)

Color of Solution

Light (almost colorless i.e. no notable change)

Pink

Dark pink

Dark pink (remains)

Margarine

Amount of KMnO4 (ml)

Color of Solution

1
2
3
4
5

N/A
Dark ping
Purple
Dark purple
Dark purple (remains)

Canola

Amount of KMnO4 (ml)

Color of Solution

1
2
3
4
5

Light (almost colorless with hints of pink)


Light pink
Pink
Dark pink
Dark pink (remains)

Amount of KMnO4 (ml)

Color of Solution

1
2
3
4

Pink
Purple
Dark Purple
Dark purple (remains)

Corn

Discussion

Mihret

Measuring the Degree of Unsaturation in Fats and Oils


In the end, corn oil and butter reached the color plateau the quickest, while canola and margarine

tied for second place. There are two problems. First, butter and canola oil had unexpected color-change
rates. Butter had a quicker reaction rate than canola, although canola has usually, according to the
measurements given above, 88% unsaturation level, higher than all of the other fats and oils used in the
experiment. Not to mention, over 50% higher than butters unsaturation level. Second, given that there is
usually a great difference between the unsaturation levels of margarine and butter on one hand and
canola and corn oil on the other, there should have been a greater difference in the amount of reagent
added to reach the color plateau. While corn oil required 4 milliliters, margarine (almost 70% less than
the unsaturation level of corn oil) required only 5 milliliters of the reagent to reach the color plateau. It
doesnt seem to reflect the great differences in unsaturation levels indicated above.
This may be because 1 millimeter of reagent is too much to add at one time; it may cause much
more chemical change than we would expect. Another reason may have been because we did not mix
vigorously. This experiment requires vigorous and thorough mixing to work.