FATS AND OILS

VERDAN, SARAH AND TADEO, ANNA KATRINA

INSTITUTE OF CHEMISTRY, COLLEGE OF SCIENCE
UNIVERSITY OF THE PHILIPPINES, DILIMAN, QUEZON CITY
ABSTRACT
Oils are synthesized from fatty acids and glycerol and the acrolein test is one that can detect the
presence of glycerin or fats. A burnt grease odor was smelt during the experiment proper. 5
drops of iodine in hexane was used in order to achieve the pink-violet positive result and 0.0025
was the degree of unsaturation calculated which implies the low unsaturation of the oil used.
Water is immiscible with oil due to the difference in polarity, while soap and detergent, due to
them having a polar and non-polar end, are able to dissolve in oil, with the detergent being more
soluble. Soaps react with divalent cations, Ca2+ and Mg2+, to form insoluble precipitates while
detergents do not. Acid contaminants render soap ineffective while detergents due to its basicity
which has the ability to neutralize acids still remains effective as an emulsifier.
INTRODUCTION
One important set of biomolecules are
Lipids.
These
are
water-insoluble
substances. These are extracted from cells
using non-polar solvents such as ether and
chloroform. There are many kinds of lipids
and this includes triacylglycerols, terpenes,
steroids, prostaglandins and phospholipids.
These generally functions in storing energy
and in giving signals to cells. Examples of
lipids are shown below.

Figure 1. Examples of lipids

In the experiment, the focus was given to

triacylglycerols or triglycerides. These are
the lipids which refer to the oils of plants
and fats of animals. These are composed of
fatty acids- long chain saturated or
unsaturated carboxylic acids composed of
even number of carbons. Fats are
triacylglycerols which are solid at room
temperature while oils are those which are
liquid at room temperature. Another
difference of fats and oils is that almost all
fats are composed of saturated fatty acids
while oils are composed of unsaturated fatty
acids.
The
general
structure
for
triacylglycerols is as follows.

non-polar ends (hydrocarbon chains).

Miscelles arrange themselves in these
ways.

Figure 2. General structure of triacylglycerols.

Fats and oils can be analyzed through its

properties and the reactions they undergo.
Degree of unsaturation of the fatty acid
residues of fats and oils can be determined
by obtaining the iodine number (also known
as iodine value or iodine index). Double
bonds or the fatty acids react with iodine.
Disappearance of the yellow color of iodine
indicates reaction with it. Iodine number is
defined as the grams of iodine decolorized
by grams of fat or oil.
Acrolein test can also be done. This
determines presence of fats. Glycerol
residue of fats reacts with KHSO 4 and gets
dehydrated then produces acrolein, a gas
with burnt grease odor. The reaction is as
follows.

Figure 3. Reaction during acrolein test.

Fats and oils also undergo alkaline

hydrolysis or saponification. Here, salts of
the fatty acids are the soaps. The general
reaction is shown below.

Figure 5. Assemblies of miscelles.

The dark parts are the polar ends while the

wiggly parts are the non-polar ends. Dirt is
composed of fats or oils. Fats and oils are
considered surfactants because they lower
surface tension thereby allowing them to
penetrate and wet other materials. Nonpolar ends are dissolved in the fats or oils.
Dirt gets surrounded by the negative or
polar ends thus preventing it from
coalescing. This is the reason why fats and
oils have cleansing properties.
There are also synthetic detergents. These
are sodium sulfonate or sodium sulfate salts
of the fatty acids. Like soaps, these also
have polar and non-polar ends. These are
considered as stronger cleansing agents
since they work well in hard water. Hard
water
contains
calcium,
iron
and
magnesium ions. Polar ends react with
these ions to form water soluble salts.
Soaps precipitate with hard water.
Examples
of
soap
and
detergent,
respectively is given below.

Figure 6. Chemical structure of soap and detergent

Figure 4. Saponification reaction of fats and oils.

Soaps exist as spherical clusters called

miscelles. Each contains soap molecules.
These soaps are considered amphipathic
because they have polar (-COO- Na+) and

In the experiment, these properties

will be tested.

METHODOLOGY
Six tests were done. First was Acrolein Test.
This was done by adding a pinch of
potassium bisulfate into 2 drops of oil. Heat
gently then vigorously. The odor of the gas
was noted. The burnt oil odor indicates
positive result.
Next is the test for unsaturatation. Iodine
number was determined by calculating the
number of grams of iodine used to see a
positive result and dividing it by 100. The
iodine in hexane solution was done by
dissolving 2.5 g of iodine crystals in 100 mL
hexane in a stoppered flask completely
covered by aluminum foil. In a 50 mL
Erlenmeyer flask, dissolve 10g of coconut
oil in 10 mL hexane then add iodine in water
drop wise using Pasteur pipette. Do this
until the color of the solution disappears.
Repeat the same procedure but this time,
olive or linseed oil will be used. Record the
number of drops of iodine in water.
Determine the iodine number through this
data.
Soap was synthesized by dissolving in 100
mL beaker 3g of NaOH pellets in 7mL
distilled water and 12 mL 95% ethanol. 6
grams of coconut oil was weighed in a
round bottom flask and the base solution
was added together with boiling chips. The
solution was refluxed for 30 minutes until
the solution was clear. While waiting, 35 g
NaCl was dissolved in 125 mL water using
400 mL beaker. When reflux was done, the
refluxed mixture was added to the sodium
chloride solution. Ice bath was used to cool
it to room temperature. The salt solution
precipitated and was collected using
vacuum filtration. 10 mL portions of distilled
water were used in collecting the
precipitate.

Cleansing action was also tested. This was

done by preparing 4 test tubes each
containing 5 drops of coconut oil. Also
prepare soap and detergent solutions. The
soap solution was prepared by dissolving
0.5 g of soap in 35 mL water. The detergent
solution was prepared by dissolving 5 g
detergent in 50 mL water. The solutions
prepared were added to a test tube
containing 5 drops of oil, separately, with
water one of the liquids added. The results
at each test tube were compared.
Effects of calcium and magnesium salts
were done by preparing 3 test tubes
containing the soap and detergent solutions.
The test tubes were shaken vigorously to
form bubbles. It was allowed to stand for
awhile and added 5 drops of 5% CaCl 2
solution. The effects on the height of the
foam were observed. The procedure was
repeated but 5% MgCl2 solution was used.
Last test done was the effect of acids. This
was done by adding concentrated HCl to 5
mL solutions of the surfactant solutions.
Addition was continued until the solution
became acidic. Acidity is tested using litmus
paper.
RESULTS AND DISCUSSION
Lipids are a large and diverse group of
naturally occurring organic compounds that
are related by their general insolubility in
water and solubility in non-polar organic
solvents like ether, chloroform, acetone and
benzene. One property that all lipids have in
common is that they are all hydrophobic.
Unlike carbohydrates and proteins, which
are defined in terms of their structures,
lipids are defined by the physical operation
that we use to isolate them [1]. Figure 7
shows some structures of various lipids.

Figure 7. Some examples of various lipids from different categories.

Fats and oils are made from two kinds of

molecules: glycerol, an alcohol with a
hydroxyl group on each of its three carbons,
and three fatty acids (carboxylic acids with
long hydrocarbon chains, saturated or
unsaturated)
joined
by
dehydration
synthesis. The terms saturated and
unsaturated refer to the number of hydrogen
bonds attached to a hydrocarbon tails of the
fatty acid as compared to the number of the
double bonds between the carbon atom in
the tail. Fats, which are common in animals,
all have single bonds between the carbons
in their long fatty acid chain making all
carbons bonded to the maximum number of
hydrogen possible, thus being called
saturated fats. These fatty acid chains are
straight and packed together closely, thus
appears solid at room temperature. Oils,
coming from plant sources, have some
double bonds between some of the carbons
of the hydrocarbon chain, causing bends in
the shape of the molecule. The number of
hydrogen attached is not the maximum
possible number so they are called
unsaturated fats and the bends in the
molecules makes them liquids at room
temperature.
The Acrolein test is a general test for the
presence of glycerin or fats. Oil is heated in

the presence of a dehydrating agent

potassium bisulfate; the glycerol part of the
molecule is dehydrated and formed
acrolein. It was accompanied by the odor of
burnt grease, and thus is a positive result.
Only five drops of iodine in hexane was
used in the oil sample dissolved in hexane
for the pink and violet color to appear. The
iodine number is directly proportional to the
unsaturation of the fat or oil. Iodine number
was calculated to be 0.0025 and implies a
low unsaturation in the waste oil.
Saponification literally meaning soap
making, is a basic hydrolysis reaction of a
fat or oil. The products of the reaction are
soap and glycerin. Soap is a mixture of salts
of various naturally occurring fatty acids. As
seen in figure 4, the reaction shown is only
a one step reaction, but in reality, it is a two
step reaction. As the fat or oil is reacted with
the base, the ester bonds are broken and
the glycerol turns back into an alcohol. The
carboxylate attracts the positive sodium ion
turning the fatty acid portion into a salt due
to the presence of the basic solution and
makes it partially insoluble in water.
Alcoholic NaOH is used because so that it
can react better with the fatty acid. Sodium
hydroxide is polar and the fatty acids are

non-polar, this may cause some repulsion

and alcoholic sodium hydroxide is used in
order to penetrate the organic molecule.

Detergents are structurally similar to soaps,

but differ in the water-soluble portion. Figure
8 shows some example of detergents.

Figure 8. Structures of some detergents.

Because fatty acid soap is a salt of a fatty

acid and alkali metal, it hydrolyzes in water
and the solution becomes slightly basic. The
solution of detergents is adjusted to slightly
basic, but this is not because of the
detergent itself, but because of the auxiliary
agents in it. This is the main difference
between the soap and detergent.
The cleansing action of both soaps and
detergents results from their ability to
emulsify or disperse water insoluble
materials such as oil and grease and hold
them in suspension in water.
Water alone cannot penetrate oil because
they are of opposite polarity. This is seen in
the first test tube, when oil is mixed with
water. The soap solution when mixed with
oil became cloudy and the oil layer became
thinner. The cloudiness is due to the fact
that soaps are not at all that soluble in
water. The thinner oil layer is due to the long
organic chain and the functional group
COO-Na+. A tail and a head best describe
this part of the soap. Figure 9 shows a
simple illustration of a soap molecule.

Figure 9. The tadpole like representation of a soap

molecule

As seen in the figure, the tail which

comprises of the long hydrocarbon chain is
water insoluble, but it is soluble in oil and
organic solvents. The head, which is the
ionic part, although the formal charge is
zero, is soluble in water. Figure 10 shows
the effect of soaps and detergents when
combined with oil.

Figure 10. Soap molecules acting on the oil or grease

in water.

When mixed with oil, the tail dissolves into

the oil and leaves the polar carboxylate ion
of each soap molecule sticking out of the oil
droplets and the surface of the oil is
negatively charged. It formed a closed
structure because of the mutual repulsion of
the positively charged heads. This structure
is called a micelle and when washed with
water, it pulls out the dirt and grime more
efficiently.
The detergent solution blended in oil yielded
a clear solution and a thinner oil layer.
Although detergents do not have sodium
salts of fatty acids, they have all the
properties of salts and their structures are
very similar (see figure 8). It has a long
hydrocarbon chain and a short ionic head.
These two parts are water repellent and
water attracting, respectively.
The cleansing action of soaps depends
upon the fact that they ionize readily in
water and pH. Fatty acids have weak
acidity, while solutions of alkali metal soaps
are slightly alkaline due to hydrolysis. If the
pH of the soap solution is lowered by acidic
contaminants,
insoluble
fatty
acids
precipitate and form a scum. If the ionic end
loses its charge, the soap would no longer
attract the water molecules and could no
longer emulsify oil and dirt. This happens in
hard and acidic water. One of the
disadvantages of soaps as cleansers is that
they are converted by mineral acids into
free fatty acids:
CH3(CH2)16CO2-Na+
+
HCl
CH3(CH2)16CO2H + Na+ + Cl-

(equation 1)
These fatty acids are less soluble than the
sodium salts and form a precipitate or scum.
Because of this, soaps are ineffective in
acidic water. Soaps also reacts with divalent
ions such as Ca2+ and Mg2+, two ions that
are abundant in hard water, and leads to
precipitates referred to as soap scum.

2 CH3(CH2)10CO2-Na+
(sodium laurate)
+ Mg2+ [CH3(CH2)10CO2-]2Mg2+ + 2 Na+
(equation 2)
Detergents were developed to overcome
these
limitations.
Detergents,
since
structurally similar to soaps, have an ionic
and a non-polar end. However, their overall
structure is not the same. Many detergents
contain phosphates or sulfates which serve
as bases to neutralize acid. Ionic detergents
may form insoluble salts with Ca2+ and Mg2+
but with lower amounts than soaps.
A surfactant is a substance which has both
a hydrophilic and hydrophobic group. When
in water, it dissociates and releases
zwitterions or double ions and is termed
ionic surfactant. On the other hand, a
surfactant that does not dissociate is called
a non-ionic surfactant. Non-ionic surfactant
can also act as emulsifying agents.
Although it does not have an ionic head, the
polar head group of the non-ionic detergent
is the one responsible for the attraction of
water to it. And thus, also achieves the
same effect as soap. Since it also lacks the
ionic head, it will not react with divalent
cations to form insoluble precipitates and is
also effective in acidic water.
Lipids have diverse and important roles in
nutrition and health. However, certain lipids,
particularly cholesterol and trans-fatty acids,
are risk factor for heart diseases and other
illnesses. The usage of soaps and
detergents are worldwide. Aside from bath
soaps and laundry detergents, these are
also seen in shampoos, conditioners and
fabric softeners, wherein the main
component is a cationic surfactant.

REFERENCES
[1] Solomons, T.W.G., Fryhle, C.B. Organic
Chemistry 9th edition upgrade. John Wiley
and Sons, Inc., USA. 2007
[2] Mohrig, J.R.; Morrill, T.C.; Hammond,
C.N.; Neckers, D.C. Experimental Organic
Chemistry. Freeman: New York, NY, 1997
[3] Wade, L.G Jr. Organic Chemistry.
Prentice-Hall Inc., Englewood Cliffs, New
Jersey. 1987.
[4] Fahy E, Subramaniam S, Brown HA, et
al (2005). A comprehensive classification
system for lipids. J. Lipid Res. 46 (5): 839
61.
[5] Berg, J.M., Tymoczko, J.L., Stryer, L.
Biochemistry, 5TH edition. Freeman: New
York, NY, 2006.

APPENDIX
I.

Data Sheet

Tests
Acrolein Test
Test for
unsaturation
Addition of
CaCl2/MgCl2

Cleansing
action
Effect of acid

Table 1. Data for the Tests on Fats and Oils

Effect on Oil
Water + oil
Soap + oil
Burnt grease
----smell
pink-violet color
-------

--

White precipitate
formed. Rate of
disappearance is
faster

---

Immiscible with
oil

cloudy solution,
thinner oil layer
Cloudy solution

---

Detergent + oil
----Amount of
bubbles
lessened. No
precipitate
formed.
Clear solution,
thinner oil layer
Clear solution,
less bubbles