Organic Chemistry

Organic Chemistry
Organic Chemistry Laboratory Ch 200 (2015-2016) Experiment 1

Separation of Ethanol from Ginebra San Miguel Using Distillation

Michael Allen Medios*, Czielle Rose Munoz, Francheska Ong Villa, and Ronelyne Paulino
Department of Psychology, College of Science
University of Santo Tomas, Espana Street, Manila 1051

Date Submitted: 2/09/16

Keywords: Distillation, Ethanol, Percent ethanol, Percent loss, Simple distillation, Fractional distillation
Abstract: In this experiment, ethanol was separated from the alcoholic beverage. Ethanol was separated from the beverage
through two methods, simple distillation and fractional distillation. After the experiment, the % ethanol and the % loss were
calculated and compared in order to determine which method was more efficient. Through the conduction of the two
methods, it was determined that the % ethanol and % loss from the simple distillation were 24% and 30% respectively,
whereas the % ethanol and % loss from the fractional distillation were 62% and 8%.

Introduction: Alcohol is a very important compound with a variety of uses ranging from commercial to
medical and even to industrial uses. The functional group of an alcohol is an OH(hydroxyl group)
bonded to a sp3 hybridized carbon. Due to the presence of an OH group, alcohols are polar compounds
with partial positive charges on carbon and hydrogen and a partial negative charge on oxygen (Anslyn,
Brown, Foote, & Iversion, 2000).
Ethanol is produced through a process called fermentation. Fermentation is the process wherein yeast
breaks down sugar into alcohol and carbon dioxide. Yeast are tiny single-celled fungi that contain
special enzymes responsible for this reaction. But through fermentation only 10%-16% of alcohol
percentage is acquired before the yeast die. To counteract this, scientists were able to find a way to
increase the concentration of alcohol in alcoholic beverages, a process called distillation.
Distillation is a method of separating liquids with differences in volatility (tendency to vaporize). It is a
method used to purify liquids. The distillation process starts by slowly heating the mixture until it
reaches the temperature of the liquid with the lower boiling point. When this happens, the liquid with the
lower boiling point will turn into a vapor and leave the mixture. In order to collect it, the distillation
apparatus has a length of tubing that cools the vapor until it re-condenses and drips out the other end.
Once most of the first liquid has left the still, the temperature will rise quickly toward the boiling point
of the second liquid, and you will know that the distillation process is complete. (Becker, 2016)

There are two types of distillation, simple distillation and fractional distillation. Simple distillation is a
process used to separate liquids with significant differences in boiling points. A simple distillation set-up
has a distilling flask (with boiling chips), which contains the liquid, a still head or distilling head, which
connects the flask to the condenser, a heat source, which heats the liquid in the flask, a thermometer and
thermometer adapter, which measures the temperature changes in the flask, and a distillation receiver
and receiver adapter, which is used to collect the distillate.
As compared to simple distillation, fractional distillation is a form a distillation which involves the
separation of liquid mixture into fractions using a fractionating column. The set-up for fractional
distillation is almost the same as the set-up for a simple distillation. The only major difference between
the two set-ups is the presence of the fractionating column (Klein, 2012).
In the experiment, the two types of distillation were used to separate ethanol from the alcoholic
beverages. After the conduction of the experiment, the % of ethanol and % loss was calculated in order
to determine which method between simple and fractional distillation is more efficient in the separation
of ethanol.

Methodology: Before the conduction of the experiment, the materials needed for the proper conduction
of the experiment were gathered. The necessities in the experiment were the distilling flask(with boiling
chips), the stillhead/distilling head, the thermometer, the thermometer adapter, the condenser, the water
inlet, the water outlet, the receiver adapter, the distillation receiver, the heat source, the test tubes and of
course, the sample of Ginebra San Miguel.
After the materials were gathered and checked, the test tubes were calibrated 0.5mL using a marker.
Afterwards, the set-up for the assigned distillation was conducted. The simple-distillation set-up was
assembled. Two iron stands were placed to serve as the whole foundation of the experiment. The first
stand had a clamp connected to it to hold the distilling flask with the boiling chips and the sample of
alcohol. Then, a distilling head was placed to connect the flask to the condenser. A Bunsen burner was
placed under the flask to heat it. A thermometer adapter and a thermometer was placed in the distilling
head to measure the changes in temperature. The second iron stand had the condenser where the heated
water traveled and connected to the condenser was the receiver adapter and the distillation receiver
which served as the container of the distillate. A rubber tubing was then connected to the condenser and
the water inlet and outlet.
After the set-up for the simple distillation was assembled, the experiment was done. The distilling flask
was being heated constantly by rotating a Bunsen burner under it. As the flask was being heated, the
water flowed through the condenser and to the test tube. After the test tube was filled with 0.5mL of
distillate the temperature was recorded on a separate sheet of paper. This was repeated until the
temperature reached 95oC or the alcohol was completely consumed. After which, the set-up was cooled
and the residue (remaining liquid) was poured into a separate container and measured.

After the experiment was conducted, the following were recorded: volume of sample, volume of
distillate, volume of residue, volume of ethanol, % ethanol, and % loss. A graph of temperature vs
volume was then made from the results of the experiment.

Results:
Table 1 Temperature vs Volume in simple and fractional distillation
Distillation
Volume

Temperature
Simple

Fractional

0.5

31.0

68.0

1.0

57.0

70

1.5

64.0

72.6

2.0

68.0

73.4

2.5

71.2

74.7

3.0

73.4

75.5

3.5

74.8

76.0

4.0

76.0

76.4

4.5

76.7

76.7

5.0

77.8

76.9

5.5

78.4

77.0

6.5

79.0

77.3

7.0

79.7

77.4

7.5
8.0

80.3
80.7

77.6
77.9

8.5

81.0

78.0

9.0

81.5

78.4

9.5

82.4

78.6

10.0

83.4

79.0

10.5

84.4

79.1

11.0

85.4

79.3

11.5

87.0

79.8

12.0

88.0

80.3

12.5

89.8

80.6

13.0

91.0

81.2

13.5

91.9

81.7

14.0

92.0

83.0

14.5

92.5

86.7

15.0

93.0

89.8

15.5

93.9

91.5

16.0

94.0

93.7

16.5

94.2

94.6

17.0

94.4

95.4

17.5

94.6

Figure 1: Plot of Temperature vs Volume

Table 2 Calculations from the experiment
Simple distillation

Fractional distillation

Volume of sample

25mL

25mL

Volume of distillate

17.5mL

18mL

Volume of residue

0mL

5mL

Volume of ethanol

6mL

15.5mL

% ethanol

24%

62%

% loss

30%

8%

Discussion:
Table I above shows the results of the experiment. The table shows the difference in temperature and
volume between simple and fractional distillation.
Figure 1 shows the relationship between volume and temperature and a better representation of the
results. The relationship of volume and temperature is seen as directly proportional. Meaning, as the
temperature increases the volume also increases. The graph shows that at 1.0mL the simple distillation
setup was at 57oC while the fractional distillation setup was already at 70C. After 2.0mL of distillate has
been acquired, the temperature of the simple distillation was at 68 oC while the temperature of the
fractional distillation was at 73.4oC. In test tube 6 or at 3.0mL, the temperature of the simple-fractional
distillation were at 73.4oC and 75.5oC. After the 4.0mL mark was reached, the temperatures measured
were 76oC and 76.4oC. At 5.0mL or the tenth test tube the temperatures for the said distillations were
already at 77.8oC and 76.9oC. The temperatures had a slight increase during the 12th test tube with 78.4oC
and 77.0oC respectively. The simple distillation had a 79.7oC on the 14th test tube while the fractional
distillation had a temperature of 77.4oC. On the 16th test tube the temperatures of she simple to fractional
distillation were 80.7OC and 77.9iC. After the continuous heating of the distilling flask, the obtained
temperatures for the simple to fractional distillation were 81.5 oC to 78.4oC at the 9.0mL mark. During
the 10mL mark the temperatures were at 83.4C and 79oC. At the 11.0mL mark the temperatures were at
85.4oC and 79.3oC. After the 12.0ml mark was reached, the temperatures were at 88.0 oC and 80.3oC.
During the 13.0mL mark the temperatures were already at 91.0oC and 81.2oC. After the continuous
heating the 14.0mL mark was reached at 92.0 oC and 83.0oC. The 15.0mL mark showed a large rise in the
temperature of the two set-ups especially in the fractional set-up. The simple distillation set-ups
temperature rose from 92oC to 93oC while the fractional distillation set-up rose from 83oC to 89.8oC. The
32nd test tube or the 16.0ml mark had the temperatures of 94.0 oC and 93.7oC. And finally, at the 17.0mL
mark the temperatures were at 94.4oC and 95.4oC respectively.
Table 2 shows the calculations of the simple distillation and the fractional distillation. The two set-ups
had the same amount of sample at the beginning. The simple distillation set-up had 17.5mL of distillate
while the fractional distillation set-up had 18mL. The residues were at 0mL and 5mL for the two set-ups.
The volume of ethanol in the simple distillation was 6mL whereas the volume of ethanol in the
fractional distillation was 15.5mL. The % ethanol were 24% and 62% respectively. And finally, the %
loss for the simple set-up was 30% while the % loss for the fractional set-up was only 8%.
From the data above it can be concluded that for the experiment, fractional distillation was the more
efficient one in separating ethanol from Ginebra San Miguel. This can be concluded as the % loss of the
fractional distillation set-up was only 8% as compared to the 30% loss of the simple set-up.
According to Palleros (2000), simple distillation is a process in which a liquid solution can be separated
into volatile and non-volatile components. But this method is not effective in the separation of all

compounds. Specifically, compounds with similar boiling points, especially those that interact very
strongly with one another, are not effectively separated by simple distillation but require a different
method, which is the fractional distillation. Thus it can be said that ethanols boiling point is perhaps
similar to that of Ginebra San Miguel.
Conclusion:
Ethanol can be separated by two methods, simple and fractional distillation. In the experiment
performed, ethanol was separated from Ginebra San Miguel through the two methods. Both the simple
and fractional distillation showed the directly proportional relationship of temperature and volume. This
means that as the temperature increases, the volume also increases.
Although the two methods can be used to separate ethanol from the alcoholic beverage, fractional
distillation was more efficient in the separation process. This can be concluded from the comparison of
the % ethanol and % loss obtained from the two set-ups.
Simple distillation is a process more effective in separating compounds with large differences in boiling
points, whereas fractional distillation is the more efficient process in separating compounds with similar
boiling points. Thus, it can be concluded that Ginebra San Miguel and Ethanol have a similar boiling
point.

Acknowledgements:
This experiment would not have been possible without the guide of our chemistry
laboratory instructors, Mrs. Erlinda Dilan and Mr. Edward Sio. I would like to thank my groupmates,
Czielle Rose Munoz, Francheska Ong Villa, and Ronelyne Paulino, for being dedicated to the
experiment and for showing cooperation, unity, and trust in each other. My other classmates were
also able to help me when my group was having trouble in conducting the experiment

References:
Anslyn, E., Brown, W., Foote, C., & Iverson, B. (2014). Organic Chemistry (7th edition). Brooks, Cole:
Cengage Learning
Becker,
A.
(2016).
Introduction
to
Distillation.
Retrieved
http.//www.education.seattlepi.com/explain-simple-vs-fractional-distillation-3690.html
Klein, D.R. (2012). Organic Chemistry. Hoboken, New Jersey :Wiley
Palleros, D.R. (2000). Experimental Organic Chemistry. NY: Wiley

Appendix:
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88,000 deaths are annually attributed to excerssive alcohol use.

from

Alcoholism is the 3rd leading lifestyle-related cause of death in the world.

Alcohol intake in morderation can be good for the heart.
Alcohol is the most commonly used addictive substance in the United States.