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Experiment 3: Distillation of Cyclohexane and Toluene



Peter Ickes
October 2, 2014


















Abstract: In this experiment, a 1:1 solution of cyclohexane and toluene was separated using
simple and fractional distillation techniques performed on both macro- and microscale levels.
Graphs of temperature vs. volume of distillate collected showed the changes in vapor
temperature for each experiment. Early and late samples of the distillate were also taken for
each experiment and then analyzed using gas chromatography. These results showed higher
purity obtained from fractional distillation when compared with simple distillation.
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Introduction:

Distillation is a laboratory method which can be used to separate liquids from a
homogenous mixture based upon their boiling points. The boiling point of a liquid is the
temperature at which the vapor pressure of the liquid is equal to the applied pressure from its
environment, i.e. the barometric pressure for a given day. Because boiling point is reliant upon
atmospheric pressure, there is a positive relationship between the two, though it is not linear. The
boiling point at a given pressure can be calculated using the Clausius-Clapeyron equation (1),
which is
(

) (1)

When dealing with a mixture of ideal liquids, their contributions to total vapor pressure
of the entire solution may be calculated using Daltons law of partial pressures (2).

(2)

Both P
1
and P
2
can be calculated using Raoults law (3). In this equation, P
1
and P
2
are
the vapor pressures of the pure liquids, respectively, at a specific temperature. N
1
and N
2
are the
mole fractions of each liquid in the mixture. Combing (2) and (3) results in the final equation (4).

and

(3)

(4)


In a mixture, the substance with the lower boiling point will boil off first. This is called
the more volatile liquid. As the procedure continues, the proportion of the two liquids in the
distillate will shift from favoring the more volatile liquid to the less volatile. In order to purify a
substance, serial distillations may be performed using an early portion of the successive
distillates.
Distillation involves heating the mixture to its boiling point, then guiding the vapors to a
cooling device where they are condensed. This liquid is known as the distillate. Two types of
distillation were conducted in this lab. In a simple distillation procedure, a mixture is heated to
boiling, the vapors rise, condense, and then are collected. In a fractional distillation, an inert
substance is inserted into the column. The vapors condense on this material first and then, as the
temperature rises towards the top of the column, they pass into the gas phase. This boil-condense
process is repeated several times, so the final distillate is much more pure than that resulting
from the simple distillation procedure.
Additionally, in this lab both microscale and macroscale distillations were performed.
The difference between these is that microscale is performed on small amounts of mixture (about
5 ml), while macroscale is performed on large volumes.
Here, both styles of distillation were performed on a mixture of cyclohexane and toluene.
The results were examined by gas chromatography and analysis of change in temperature reliant
upon volume of distillate collected.
A note should be made here concerning azeotropes, liquid mixtures that do not form ideal
solutions. Azeotropes form solutions that have boiling points either higher or lower than their
pure liquid substances. An example can be seen in water and ethanol, which together have a
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boiling point of 78.2 C, while separately, water and ethanol have boiling points of 100 C and
78.3 C, respectively.

Procedure

Microscale Distillation
A microscale simple distillation apparatus was set up as shown in Figure 1. 2 ml each of
cyclohexane and toluene were added to a roundbottom boiling flask in addition to a boiling chip.
The flask was heated on an aluminum block placed upon the corner of a hot plate. The sample
was heated until it began to boil and the distillation rate reach approximately 1 drop every 5
seconds. After the first 3 drops had distilled, the next 3 were collected in a vial for analysis by
gas chromatography (GC). The distillation proceeded until approximately 3 ml of condensation
was collected. Then, 3 final drops were sampled and sent for GC analysis. The temperature of
the vapor was recorded every 2-3 drops over the course of the distillation.
After the apparatus had cooled, a fractional column was added. This altered set up is
shown in Figure 2. Fresh cyclohexane and toluene were added to the flask along with a new
boiling chip. The same procedure as above was then performed with the fractional column in
place. The early and late distillate samples were also submitted for GC analysis.
A temperature versus time graph of both the simple and fractional distillations plotted on
the same axes is shown in Graph 1.

Macroscale Distillation
A simple distillation apparatus was set up as shown in Figure 3 using a 100 ml round
bottom boiling flask. 30 ml each of cyclohexane and toluene were added to the flask with a few
boiling chips. This mixture was heated with a heating mantel until the condensation dropped at a
regular rate of approximately 1 drop per second. This was collected in a graduated cylinder.
After the first 3 drops distilled, the next 3 were collected for GC analysis. The temperature was
recorded for every 2 ml of distillate. This experiment was run until 50 ml of distillate had been
collected. At this point, 3 final drops were collected in a vial for analysis via GC.
Once the apparatus had cooled, a fractional column was added. The cyclohexane and
toluene distillate collected from the previous macroscale simple distillation was reused for the
following experiment, while new boiling chips were added. The procedure was then conducted
according to the same process outlined in the immediately preceding paragraph. Early and late
samples were again collected for GC analysis. Again, the procedure was run until approximately
50 ml had been collected.
Temperature vs. volume collected results for both simple and fractional macroscale
distillations are shown in Graph 2.

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Figure 1. Simple Microscale Distillation
Apparatus used to separate 4-mL mixture
of 1:1 cyclohexane:toluene.
Figure 2. Fractional Microscale Distillation
Apparatus used to separate 4-mL mixture of
1:1 cyclohexane:toluene. Aluminum foil was
wrapped around the fractional column.
Figure 3. Simple Macroscale Distillation
Apparatus used to separate 60-mL mixture
of 1:1 cyclohexane:toluene.
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Results and Discussion

Shown below is Graph 1, a comparison of temperature of the vapor compared to the
number of drops collected. As can be seen from the graph, though the simple distillation ended at
a slightly higher temperature than the fractional distillation.


Moving on to the macroscale distillation, shown in Graph 2, it can be seen that the
fractional distillation shows a slightly more radical shift in temperatures during the middle period
of the experiment, indicating a radical shift in composition of both the distillate and the still-
boiling solution.
75
77
79
81
83
85
87
89
91
93
2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40 42 44 46 48 50
T
e
m
p
e
r
a
t
u
r
e

(

C
)

Drops Collected
Graph 1: Microscale Distillation
75
80
85
90
95
100
105
110
2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40 42 44 46 48 50
T
e
m
p
e
r
a
t
u
r
e

(

C
)

Volume Collected (ml)
Graph 2: Macroscale Distillation
Simple Fractional
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Below, in Table 1, is shown the percentages of each cyclohexane and toluene taken from
the early and late samples using GC analysis. The range for the fraction distillation is shown as
slightly smaller than the simple distillation. This is indicative of the effects the fractional column
has on the process, resulting in a purer distillate at the early and late extremes of the process.
Also, it can be seen from this table that the boiling point of cyclohexane is lower than that of
toluene. This was confirmed in the literature, which listed the boiling point of cyclohexane as 81
C, whereas the value for toluene is 111 C.


Finally, the GC results from the two macroscale distillations are shown in Table 2 below. This
makes it extremely apparent that the fractional column adds greatly to producing a more pure
distillate. This is trend is confirmed in both the graphs as well, which show a sharp shift in the
temperature when compared to volume of distillate collected, indicating a radical shift in the
composition of both the distillate and the liquid left in the flask.

Table 2 Macroscale Distillation
Simple Fractional
Early Late Early Late
% Cyclohexane 73.89 10.03 84.46 3.17
% Toluene 26.06 89.95 15.47 96.81

Conclusion
This experiment consisted of distilling a mixture containing equal halves of cyclohexane
and toluene, both by macroscale and microscale distillation. In each of these two categories, both
simple and fractional distillation was done. After collecting early and late samples during each
distillation, it was found in all cases that fractional distillation is more accurate and efficient in
separating cyclohexane and toluene. This was the result of the increased surface area provided by
the fractional column, which allowed a greater number of liquid-gas phase changes as the vapor
itself condensed and re-boiled several times as it moved up the column. Neither the micoscale
nor macroscale distillation results indicated whether one was significantly better than the other at
separating the two substances.

Table 1 Microscale Distillation
Simple Fractional
Early Late Early Late
% Cyclohexane 70.84 2.16 73.04 4.32
% Toluene 29.13 87.81 26.92 95.66
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References
Macroscale Distillation Apparatus. (2014). Image. Found on: www.ochem-melting-
pod.wikispaces.com/Distillation+of+Acetone

Microscale Distillation Apparatus. (2013). Image. Found on:
www.geocities.ws/dcarrd2000/infroduction.1html

Zubrick, J. W. (2008). The organic chem lab survival manual: A students guide to techniques.
Danvers, MA: John Wiley & Sons, Inc.