Experiment No.
SEPARATING LIQUID COMPONENTS OF TANDUAY RUM BY
SIMPLE DISTILLATION
INTRODUCTION
Distillation is a commonly used method for purifying liquids and separating
mixtures of liquids into their individual components. Familiar examples include the
distillation of crude fermentation broths into alcoholic spirits such as gin and vodka,
and the fractionation of crude oil into useful products such as gasoline and
kerosene. In the organic laboratory, distillation is used for purifying solvents and
liquid reaction products.
The process of distillation is much like the process of how rain occurs (Figure
1). At any temperature, some molecules of a liquid possess enough kinetic energy to
escape into the vapour phase (evaporation) and some of the molecules in the vapour
phase return to the liquid (condensation). Equilibrium is set up with molecules
going back and forth between liquid and vapour. At higher temperatures, more
molecules possess enough kinetic energy to escape, which results in a greater
number of molecules being present in the vapour phase.
Figure 1. Liquid molecules of water escape from the surface upon acquiring enough
kinetic energy from the heat of the sun forming vapour phase which then rises up to
the troposphere. When the air cools it condenses around some dust or other
particles in the air, called condensation nuclei. These small droplets then become
visible as clouds. Warm air can hold more moisture than cool air, so when the
warmer air is cooled and the moisture condenses, heavy rain can be observed.
In the following graphs (Figure 2-3), as the temperature of the water is
increased, the vapour pressure also increases. At some point, as the temperature is
increased, the liquid begins to boil. This happens when the vapour pressure of the
liquid equals the applied pressure (for an apparatus that is open to the atmosphere,
the applied pressure is equal to 1 atmospheric pressure, that is, 1 atm = 760
mmHg). For water, this occurs at 100°C. For ethanol, this occurs at 78.4°C. The
boiling point (BP) of water and ethanol, therefore, are 100°C and 78.4°C,
respectively. The definition of the boiling point of a liquid in an open container
then is the temperature at which its vapour pressure equals atmospheric
pressure.
Figure 2. The
vapour pressure of water against increasing temperature. Notice that at 100°C, the
vapour pressure of water is equivalent to the atmospheric pressure which is 760 in
mmHg and 1 in
atm.
Figure 3. The vapour pressure of ethanol against increasing temperature. Notice
that at 78.4°C, the vapour pressure of ethanol is equivalent to the atmospheric
pressure which is 760 in mmHg and 1 in atm.
The boiling point of liquids varies from one compound to another (Table 1),
which is governed by the intermolecular forces of attraction present among the
molecules in the liquid. These intermolecular forces must be disrupted for the liquid
to vaporize. Therefore, liquids with stronger intermolecular forces have a higher
boiling point.
Table 1. Boiling points of some Compounds
Prefix Chemical Functional Groups Boiling point (°C)
acetone ketone 56
methyl acetate ester 57
sec- butylamine amine 63
methanol alcohol 68
ethyl iodide halide 71
n- butyraldehyde aldehyde 75
ethanol alcohol 78
diisopropylamine amine 84
water 100
n- propyl acetate ester 102
The difference in the boiling points of liquids becomes the basis of separating
liquid components of a mixture via distillation. Supposedly a mixture contains water
and ethanol. Applying heat into the distillation flask containing this mixture will
cause a rise of temperature until it reaches the boiling point of the liquid which has
a lower boiling point—the ethanol. At this temperature, most of the ethanol will
evaporate with minimal water. The hot vapour that contains the ethanol passes into
the condenser where the vapour is cooled and converted back to liquid in a purer
form and collected in a receiving flask. This is the essence of distillation - starting
with a mixture of liquids having different BPs, going through the process of
distillation, and ending up as distillate that is enriched in the lower-boiling
component. Because more of the lower-boiling liquid has distilled, the residue left
behind in the distilling flask is necessarily enriched in the higher boiling component.
Separation has been accomplished.
In this experiment, the different components of Tanduay Rum will be
separated through simple distillation.
GENERAL OBJECTIVES
At the end of the experiment, the student should be able to:
1. describe when and how do liquids boil;
2. separate the liquid components of a mixture base on different boiling
points of compounds; and
3. determine the identity of component compounds that were separated.
SAFETY ALERT
1. Examine all glassware for cracks and other weaknesses before
assembling the distillation apparatus. Watch out for “star” cracks in
round-bottom flasks, because these can cause a flask to break upon
heating.
2. Proper assembly of glassware is important in order to avoid possible
breakage and spillage or the release of distillate vapours into the room.
Be certain that all connections in the apparatus are tight before
beginning the distillation.
3. The apparatus used in these experiments must be open to the
atmosphere at the receiving end of the condenser. Never heat a closed
system, because the pressure build-up may cause the apparatus to
explode!
4. Be certain that the water hoses are securely fastened to your condensers
so that they will not pop off and cause a flood. If heating mantles or oil
baths are used for heating in this experiment, water hoses that come
loose may cause water to spray onto electrical connections or into the
heating sources, either of which is potentially dangerous.
5. Avoid excessive inhalation of organic vapour at all times.
CHEMICALS AND MATERIALS
Chemicals Materials
Tanduay rum 150 mL distillation apparatus 1 set
iron stand 2
utility clamp 2
watch glass (big) 1
rubber tubing 2
boiling chips 3
hot plate 1
50-mL graduated cylinder 1
10-mL graduated cylinder 1
test tubes (with cap) 5
test tube rack 1
matchsticks 1 box
wash bottle 1
PROCEDURE
A. Distillation
1. Allow a laboratory technician to set-up the distillation apparatus.
2. On the datasheet, sketch and completely label the apparatus required
for a simple distillation.
3. Ensure that the mercury bulb of the thermometer placed at the head of
a distillation apparatus is adjacent to the opening of the condenser.
4. Pour 50 mL of Tanduay rum using a graduated cylinder into the
distillation flask. Add boiling chips.
5. Turn on the water to cool the condenser.
6. Start the flameless heating apparatus and begin heating the contents
inside the flask.
7. As soon as the liquid begins to boil and the condensing vapours have
reached the thermometer bulb, regulate the heat supply so that
distillation continues steadily at a rate of 1 drop per second.
If a drop of liquid cannot be seen suspended from the end of the
thermometer, the rate of distillation is too fast.
8. Collect the drops of distillate in a 10-mL graduated cylinder.
9. As soon as the distillation rate is adjusted and the head temperature is
constant, note and record the temperature.
10. Transfer the first 5.00-mL fraction of distillate in the test tube labelled
as “Batch 1” using CD marker.
Do not used labelling tapes. This could clog the sink when washing the
glassware after the experiment.
11. Transfer the succeeding 5.00 mL fractions into the appropriate test
tubes with constant monitoring on any temperature change.
12. When the head temperature rises, note at which it becomes constant
then record this temperature.
13. Note the batch number of the distillate collected at this point.
14. Record the appearance of the distillate and the residue in the distilling
flask.
15. Stop the distillation. The separation has been accomplished.
B. Test for Identity of Distilled Components
1. Determine the identity of the distillate and residue by comparing their
experimental boiling points against theoretical boiling points of known
compounds shown in Table 1.
2. Use the flammability test outlined below to support your answer.
3. Test the flammability of each fraction by transferring the collected
distillate into a watch glass.
4. Apply a lighted matchstick over the watch glass.
5. Record the time from the point when the distillate catches the flame
until all distillate is consumed.
6. Repeat steps 1-3 using 5.00 mL of the residue from the distilling flask.
REFERENCES
1. Gilbert, J.C. and Martin, S.F. Experimental Organic Chemistry: A
Miniscale and Microscale Approach. 5th ed. p. 133
Group No.: _______ Date Performed:___________________
Name: ____________________________ Date Submitted:___________________
Course and Year: _________________ Instructor: ________________________
Score: ___________/ pts
REPORT FORM Rating: __________
Experiment No. 1
SEPARATING LIQUID COMPONENTS OF TANDUAY RUM BY
SIMPLE DISTILLATION
I. OBSERVATIONS/DATA
Sketch and complete label of a simple distillation
A. Distillation
Table 2. Log of Distillate Temperature
Batch Number Observed Batch Number of Observed
of Distillate Temperatures (°C) Distillate Temperatures (°C)
1 4
2 5
3 6
Appearance of the distillate: ___________________________________
Appearance of the residue: ___________________________________
Which batch of 5-mL distillate did the temperature start to increase? _______
What is the reason for the increase in temperature as the distillation proceeds?
B. Test for Identity of Components
Table 3. Flammability of Distillate and Residue
Flammability of Distillate Flammability of Residue
Batch Number Time Vol. of residue Time
3 5.00 mL
Table 4. Identity of Liquid Components base on Boiling points and Flammability
Distillate Residue
Batch Number Identity Vol. of residue Identity
3 5.00 mL
5
II. QUESTIONS
1. Define the following terms:
a. distillation
b. purify
c. evaporation
d. condensation
e. kinetic energy
f. troposphere
g. vapour pressure
h. atmospheric pressure
i. head temperature
2. Give the structure of the separated liquid components of Tanduay rum.
3. Explain the role of the boiling chips normally added to a liquid that is to be
heated to boiling.
4. The top of the mercury bulb of the thermometer placed at the head of a
distillation apparatus should be adjacent to the exit opening to the condenser.
Explain the effect on the observed temperature reading if the bulb is placed:
(a) below the opening of the condenser;
(b) above the opening.
5. Why should you never heat a closed system, and how does this rule apply to a
distillation?
6. The atmospheric pressure decreases when the altitude increases (above sea
level). What would be the effect of the altitude to the boiling point?
7. How would the observed boiling point of ethanol and water be affected if
distillation was performed on top of a mountain? Explain.
