CHM145L Organic Chemistry 1 Laboratory

1st Quarter, S.Y. 2015-2016

Simple and Steam Distillation

Castro, Ethan Zachary G., Pasia, Abraham Paul L., Pulido, Froileth S.1
1

Professor Oliver Villaflores, School of Chemical Engineering, Chemistry, Biological Engineering and Materials

Science Engineering, Mapa Institute of Technology; 2Castro, Ethan Zachary G., Pasia, Abraham Paul L., Pulido,
Froileth S., CHM145L-C11, School of Chemical Engineering, Chemistry, Biological Engineering and Materials
Science Engineering, Mapa Institute of Technology

ABSTRACT
One unique physical property that may distinguish the identities of substances, most especially
liquids, is their boiling point, or the temperature where the vapor pressure they exert equals the pressure of
the surroundings or the atmosphere. This characteristic of liquids also dictates another property called
volatility, which is defined as the tendency of a liquid to evaporate quickly. Due to the vast combinations of
intermolecular forces present in different liquid substances, and other factors as well, almost every substance
has its own distinct boiling point, different from another, although there are theoretical situations where boiling
points of various substances are equal (such as in vacuum, where there is no pressure). However, in real
life, most liquids have their own boiling points: thus, they have varying volatilities as well. The difference in
volatility of substances is what makes the process of separation and purification, called distillation, possible.
In the first part of the experiment, simple distillation of impure toluene was demonstrated, by taking advantage
of the difference in volatility of toluene and the impurity present. Toluene, which is more volatile, is converted
to vapor as heat is provided to the distillation system via a hot plate. As the vapor form of toluene passes
through the condenser, the difference in temperature between the vapor and the fresh water that is constantly
flowing in that part of the set-up allows the toluene to condense back to its liquid form, thereby separating it
from the impurity. The pure toluene was then collected in a graduated cylinder to measure the amount of
toluene being distilled in a certain level of temperature. The toluene, as observed, began to boil at around
38C and began condensing when the temperature was approximately 101C. Of 15 milliliters of the impure
sample, 12.5 milliliters of toluene were recovered. Moreover, the second part of the experiment dealt with
steam distillation, which is utilized when the substance to be distilled is not exerting enough vapor pressure
at high temperatures, such as para-dichlorobenzene, the substance analyzed in the experiment. Additional
vapor pressure is added by the steam to the distillation system via steam generator, allowing the pdichlorobenzene to boil even without reaching its boiling point yet. The distillate were collected in a flask and
then cooled in a cold-water bath. After cooling, the mixture was filtered, immediately dried and weighed.
Keywords: boiling point, volatility, distillation
INTRODUCTION
Volatility can be defined as the tendency
of a compound to vaporize. In a specific
temperature, a compound that has a higher
vapor pressure will vaporize more readily than a
substance with a lower vapor pressure. To put it
in other words, at a certain temperature, the
more volatile the compound is, the higher will be
Experiment 2 | Group 4 | October 15, 2015

the pressure of the vapor in dynamic equilibrium

with its vaporizing substance.
Vapor pressure can be described as the
pressure at which the gaseous phase is in
equilibrium with its liquid or solid phase. It can be
a measure of the tendency of molecules and
atoms to escape from a liquid or solid. In
atmospheric pressures, an instance when the
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vapor pressure of a liquid increases with the

temperature increases to the point at which it
equals the atmospheric pressure, the liquid has
attained the temperature at which the liquid
changes its state from a liquid to a gas
throughout its bulk, this can be referred as boiling
point. It is commonly called as the liquids normal
boiling point.
The normal boiling point of a liquid will be
at a lower temperature the greater is the
susceptibility of its molecules to escape from the
liquid, specifically, the higher the vapor pressure.
In other words, the higher the vapor pressure of a
liquid, the higher is the volatility and the lower is
the normal boiling point of the liquid, therefore, a
direct relationship can be deduced between the
vapor pressure and the volatility.

Figure 1. A common vapor pressure chart for several

liquids

Experiment 2 | Group 4 | October 15, 2015

Different compounds will exert different

vapor pressures at a given temperature because
of variations in the intermolecular forces of
attraction working in these different compounds.
In terms of intermolecular forces, the boiling point
acts as the temperature at which the liquid
molecules hold enough kinetic energy to
surmount the several intermolecular attractions
binding molecules to each other within the liquid.
Hence, the boiling point is also an indicator of the
strength of those intermolecular attractive forces.
The stronger the intermolecular attractive forces
are, the more difficult it is for molecules to
escape from the liquid and therefore, a lower
vapor pressure of the liquid. Through this, an
indirect relationship can be established, for
instance, the lower the liquids vapor pressure,
the higher the temperature must be to initiate
boiling and then, resulting to a direct relationship
between intermolecular attractive forces and the
normal boiling point.
Through the aforementioned discussed
concepts, it is therefore possible to separate
compounds from each other in a mixture based
on volatility differences. More volatile compounds
have higher possibility to be converted into vapor
earlier than with low volatilities, this process is
known as distillation. Distillation is a widely used
method for separating mixtures based on the
differences in the conditions (boiling point,
volatility, etc.) required to change the phase of
the components of the solution. To perform this
process, the liquid must be heated to transform
the components into vapor (Again, this process is
feasible since compounds with higher volatilities
vaporize earlier.) then, the vapor will be
condensed back into liquid form and collected in
a receiving container. Usually, distillation can
help the researchers to determine the boiling
point and to purify compounds (repeating the
describe process can make the compound
purer).
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In this experiment, two types of

distillation were performed, simple and steam
distillation.
Simple distillation is a procedure in which
a volatile compound is separated to a nonvolatile
compound or separating compounds with
different boiling points through application of
heat. This can be used to virtually separate
liquids that have at least fifty degrees difference
in their boiling point, or to separate highly volatile
compound from a lowly volatile compound. As
the liquid being distilled is heated, the vapors that
form are the richest in the component that boils
at the lower temperature and highly volatile. As
the process progresses, the vapors of the volatile
compound goes to the distilling flask through a
sidearm and then reaches the condenser, which
should be surrounded by fresh water at all times.
The difference between the temperature of the
fresh water and the vapor in the condenser
forces the vapor to change back into liquid form
which is then collected in another flask. It is also
important to take note of the following in order for
simple distillation to be successful:
1. The substances to be separated must
have a large volatility difference. Often,
this translates to a boiling point
difference of around 80C to 100C.
Otherwise, both compounds may be
distilled off and will not be separated
from each other.
2. Gently supply the heat to the distilling
flask.
3. The thermometer bulb used to measure
the boiling of the distilling liquid must be
at the level of the sidearm.
4. The distilling flask must be in an upright
position at all times.
5. Glass beads or ceramic material must
always be present inside the distilling
flask prior to heating of the mixture.
Experiment 2 | Group 4 | October 15, 2015

6. Fresh cooled water must always fill the

condenser, therefore, running water
should be applied to the condenser.

Figure 2. A typical simple distillation set-up

When a solution or mixture of two nearly

immiscible liquids is heated while being
discomposed to display the surface of one liquid
to the vapor phase, each of the component
independently wields its own vapor pressure as a
function of temperature as if the other component
were not present. Resulting to the increase of the
vapor pressure of the whole system. Take note
that boiling starts when the sum of the vapor
pressures of the two immiscible liquids just
predominates the atmospheric pressure. In such
way, several organic compounds insoluble in
water may be purified at a specific temperature
well below the point at which decomposition
occurs. Typically, water is introduced into the
distillation apparatus to provide additional vapor
pressure to help a nonvolatile organic compound
to boil off and be distilled at a temperature much
lower than its normal boiling point. The water
vapor bears the small amounts of the vaporized
compound to the condensation flask, where the
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separation of the condensed liquids phase

happens, allowing then for easy collection. This
concept effectively allows for distillation at lower
temperatures, reducing the decomposition or
deterioration of the desired products. After
distillation, the vapors, again, are condensed
suitably. Usually, the immediate product is a twophase system of water and the organic distillated,
this can be separated by decantation, partitioning
or other appropriate methods. In this experiment,
the water in the distillate is separated through a
separatory funnel.

Figure 3. A typical steam distillation set-up

The steam distillation apparatus are

constituted of three main parts:

Steam Generator

Sample Flask

Collecting Flask

This part supplies

sufficient steam to
add to the vapor
pressure of the
organic compound.
This flask contains
the compound to be
distilled with water,
and heat sources for
both the steam
generator and the
sample flask.
Guides the collection
of distillate.

It is also important to take not of the

following to successfully perform steam
distillation:
1. Boiling chips must be present both in the
steam generator and the sample flask before
heating is started.
2. Gently apply heat to the steam generator
and the sample flask.
3. The condenser must always be filled with
fresh water during the entire process.
4. No reactions should happen between the
compound being steam distilled and with
water.
Experiment 2 | Group 4 | October 15, 2015

METHODOLOGY
The experiment are divided into two
parts, the first part is the simple distillation and
the second part is the steam distillation.
In the first part of the experiment, the
researchers must assemble the set-up shown in
the figure in their laboratory manual (Figure 3.1,
page 19). Transfer 15 milliliters of impure carbon
tetrachloride into the pear-shaped flask using a
pipette (the flask should contain only 1/3 of its
total volume). Then, turn on the hot plate and
switch on the heat regulator to number 6. As it
progresses, collect the distillate at different
temperatures at the rate of 1 drop per second.
Measure, then, the volume of the distillate
obtained at different temperatures. Continue the
distillation until about 1 to 2 milliliters of distillate
is left in the flask. After this, plot the temperature
against the volume of distillate collected. Also,
record the temperature at which most of the
liquid distills as the boiling point.
Obtain a 2 grams-sample of impure pdichlorobenzene from the instructor and
determine the melting point range of the mixture.
Assemble the set-up like in Figure 3.2, page 19
of the laboratory manual, the researchers should
make sure that there is no leak in the set-up.
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RESULTS AND DISCUSSION

For the first part of the experiment in
which simple distillation was used, the impure
toluene was purified. After boiling the substance
in the distilland for about 10-15 minutes, the first
drop was collected at the temperature of 102C
and the distillation stopped at the temperature of
123C. The boiling point range of toluene was
therefore concluded to be 102-123 C. The graph
below illustrates the temperature plotted against
the volume of the distillate. At the end, 83.33
percent of the 15 milliliters of toluene was
recovered. Also, the recovered substance is
clear. Theoretically, simple distillation, is only
successful when the difference between the
boiling points of the components of the mixture is
very large but compared to other types of
distillation, it has a simpler set up and it
consumes less energy. In simple distillation, the
more volatile component of the mixture, which is
toluene, is being removed by turning it to vapors
Experiment 2 | Group 4 | October 15, 2015

and condensing it into another flask. It was

observed that as the temperature rises the
volume of the liquid in the receiving flask is also
increasing. On the other hand, the less volatile
component of the mixture is left in the distilland.
Through slow distillation via controlled heating,
both the components can be separated by
changing the receiving flask. This explains the
significance of the addition of glass beads. The
borosilicate glass beads provide surface area for
the condensation-evaporation process, this
prevents bumping or the rapid boiling which
could ruin the setup. Heating rate is also
controlled to prevent superheating which also
results into bumping.

Temperature,C

Boil slightly a hundred milliliters of water

in the Erlenmeyer flask before connecting it to
the set-up, this will serve as the steam generator.
As the researchers heat the water, put the
sample inside the pear-shaped with arm flask
and partly dissolve it in 5 milliliters of water by
gently applying heat in the mixture. After which,
connect all the apparatus and heat the steam
generator before proceeding with the distillation.
Continue the process until all the pdichlorobenzene has distilled, this should take
about 10 to 15 minutes. Before disconnecting the
apparatus, cool the mixture in the receiving tube.
Then, filter the p-dichlorobenzene with suction
and air dry the compound, the researchers
should not allow it to stand in the open for a
longer period since it will evaporate. Weigh the
dried material, obtain its melting point and
compute the percentage recovery.

123
122
121
120
119
118
117
116
115
114
113
112
111
110
109
108
107
106
105
104
103
102
0.75 1.75 2.75 3.75 4.75 5.75 6.75 7.75 8.75 9.75 10.75 11.75 12.75

Volume of the Distilate, mL

Figure 4. Plot of temperature against the volume of the

distillate

In the second part of the experiment,

para-dichlorobenzene was purified using steam
distillation. Simple distillation is not applied in
purifying this compound because boiling it will
only cause the compound to decompose so,
steam distillation is executed instead. Steam
distillation is used in purifying temperaturesensitive material such as para-dichlorobenzene
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which is a hydrocarbon aromatic compound.

Steam is added to the distillation apparatus to
lower the boiling point of para-dichlorobenzene
and prevents its decomposition. A hundred
milliliter water was boiled which will act as a
steam generator while heating the slightly
dissolved test compound. Cloudiness was
observed as the test compound was transferred
to the pear-shaped flask. Before the distillation
started, a safety tube was connected to the cork
of the steam generator to allow the water to
escape when the pressure is too high. The
distillation lasted until all the p-dichlorobenzene
has been distilled. The liquid in the receiving
flask was cooled, filtered and air dried. At the
end, 95.2 percent of the 2.00 grams of paradichlorobenzene was extracted.

CONCLUSION AND RECOMMENDATIONS

The researchers were able to apply the
technique of distillation in both simple and steam
distillation. In the former, it is known that in order
to be able to accomplish a successful
experiment, the substances in question must
have large differences in volatility. Without this in
consideration, both constituents may be distilled
off together and result in an unsuccessful
experiment. In the latter, steam distillation is
often used when the vapor pressure of a
dissolved organic compound still remains low
even at high temperature levels. Steam
distillation is effective due to its means of addition
of vapor pressure through a steam generator.
This addition of vapor pressure results in the
mixture attaining atmospheric pressure at lower
temperatures. This is significantly important
because, sometimes, organic compounds will
decompose faster than it will take for it to boil. A
decomposition of the desired product will result in
a very fruitless distillation experiment.

Experiment 2 | Group 4 | October 15, 2015

Simple distillation is effective in terms of

its setup and the time it takes to distill a liquid.
Compared to the steam distillation, simple
distillation required less apparatus to be used
and required less time to finish its distillation
process. Simple distillation however, is limited to
mixtures that have large differences in boiling
points. If simple distillation is done on a mixture
that had fairly close (<80C) boiling points, this
would not be a very effective means of
separation of constituents.
Steam distillation is most useful in trying
to avoid decomposition of organic compounds.
By providing additional vapor pressure, the
researchers lowered the required heat needed to
boil the liquid. This prevented the organic
material from decomposing before being distilled
off and separated from the original mixture.
Steam distillation however, requires more
equipment in comparison to simple distillation.
It is recommended for researchers to
absolutely make sure that your setup is properly
assembled and has no leaks where steam or gas
might escape. This is crucial for distillation relies
heavily on the gas evolved from the heated
mixture that is then cooled to be turned into a
liquid. It is also recommended that researchers
try different organic compounds to thoroughly
see the effects of volatilities in distillation setups.

References
Baluyut, J. G., & De Castro, K. A. (2001). Organic
Chemistry Laboratory Manual for Chemistry
Students Part 1. Intramuros, Manila: Mapua
Institute of Technology.
Beychok, M. (2012, January 1). Volatility (chemistry).
Retrieved from The Encyclopedia of Earth:
http://www.eoearth.org/view/article/172247/

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Klein, D. (2012). Organic Chemistry. In D. Klein,
Organic Chemistry (p. 41). New Jersey: John
Wiley and Sons, Inc.
Samal. (2015). Department of Chemistry. Retrieved
from Univeristy of Massachusetts:
http://www.chem.umass.edu/~samal/269/cry
st1.pdf

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