CHM 1321D- Organic Chemistry

LAB REPORT EXPERIMENT N0 2

Purifying Chemicals by Distillation

Thursday, 02nd February 2017

Name: Magloire Segla

Student #: 8363344

Lab Partner: Sara Nasr (8173184)

TA: Philip Eckert (pecke008@uottawa.ca)

CHM 1321D- Organic Chemistry
Procedure: Please refer to the lab manual

Observations:

Part 1: Simple distillation

Our mixture of 25mL containing 2-propanol and 1-butanol was a clear and
colorless solution.
Heat was set at 80C in order to get the solution boiling, and then lowered at
75C after getting 5mL of solution in the receiving flask.
A few minutes in the experiment, distillate drops could be seen in the receiving
cylinder.
Temperature jumped initially from 48 to 84C, and stayed relatively constant
despite its steady rise.
Part 2 : Fractional distillation
In the first few minutes of this part, vapor was not reaching the top as the
fractioning column stayed cool. Aluminum foil was used to insulate both our
distilling flask and our distillation head.
We observed a drastic increase in temperature after insulation: 24.1C to 82.9C.
The thermometer bulb was placed at the outlet from the fractioning column

Results:
Figure 1: Table for Temperature/ml of distillate in Simple Distillation

Volume of Temperature of
Distillate (mL) Distillate (oC)
1mL 26.1oC
2 mL 84.4 oC
3 mL 84.6 oC
4 mL 84.9 oC
5 mL 86.3 oC
6 mL 86.7 oC
7 mL 86.9 oC
8 mL 87.1 oC
9 mL 87.6 oC
10 mL 88.3 oC
11 mL 88.7 oC
12 mL 88.9 oC
13 mL 89.1 oC
14 mL 96.0 oC
15 mL 108.5 oC
16 mL 108.7 oC
 CHM 1321D- Organic Chemistry

17 mL 108.8 oC
18 mL 112.8 oC
19 mL 114.5 oC
20 mL 115.2 oC
21 mL 117.0 oC
22 mL 117.3 oC
23 mL 117.4 oC
24 mL 117.7 oC
25 mL 117.7 oC

Figure 2: Graph of Relationship between Temperature and Volume of Distillate for Simple Distillation

110

100
Temperatu 90
re of
Distillate 80
(C) 70

60

50

40

30

20

10

0
0 2 4 6 8 10 12 14 16 18 20 22 24

Volume of Distillate (mL)

CHM 1321D- Organic Chemistry

Figure 3: Table for Temperature/ml of distillate in Fractional Distillation

Volume of Distillate (mL) Temperature of Distillate (oC)

1mL 24.1oC
2 mL 82.9 oC
3 mL 83.0 oC
4 mL 83.3 oC
5 mL 84.1 oC
6 mL 84.4 oC
7 mL 84.9 oC
8 mL 86.2 oC
9 mL 86.5 oC
10 mL 87.4 oC
11 mL 87.6 oC
12 mL 90.0 oC
13 mL 93.7 oC
14 mL 94.4 oC
15 mL 101.6 oC
16 mL 106.8 oC
17 mL 109.8 oC
18 mL 113.8 oC
19 mL 115.3 oC
20 mL 116.5 oC
21 mL 116.9 oC
22 mL 116.9 oC
23 mL 117.0 oC
24 mL 117.2 oC
25 mL 117.5 oC
 CHM 1321D- Organic Chemistry

Figure 4: Graph of Relationship between Temperature and Volume of Distillate for Fractional
Distillation

110

Temperatu
100
re of
Distillate
90
(C)

80

70

60

50

40

30

20

10

0
0 2 4 6 8 10 12 14 16 18 20 22 24

Volume of Distillate (mL)

 CHM 1321D- Organic Chemistry

Figure 4: this is what the Graph of the Relationship between Temperature and Volume of Distillate for
Fractional Distillation should look like (taken from Sara Nasr).

Temperatu
re of
Distillate
(C)

Volume of Distillate (mL)

CHM 1321D- Organic Chemistry

Discussion:

Distillation is a method that consists in separating two or more compounds on the basis of their
boiling points: liquids are vaporized and the vapors are condensed and collected.

Part 1: The simple distillation although faster, is not as effective as the fractional distillation.
We can see by looking at the various graphs in the lab manual and at figure 1 above that there
is no evident separation of the compounds in the mixture: absence of an immediate spike, but
instead we have a steady slope increase. The rise that we observe from both the experimental
data (figure 1) and the graph above (figure 2) occurs at approximately 14-15mL. Looking at the
2 compounds in our mixture and for us to determine the boiling points of each, we must look at
their molecular size as both compounds contain the functional group characteristic of alcohols:
OH. 2-propanol evaporates first: its fewer number of atoms results in much more smaller
molecules , and thereby the overall compound displays less intermolecular forces (induced
dipoles from Van der Waals forces) when compared to the 1-butanol. It will therefore take less
energy to change the 2-propanols state from liquid to gas: we observe on figure 2 the
evaporation of 2-propanol at a temperature of approximately 90C. 1-butanol evaporates
second and last: its higher number of atoms results in much bigger molecules, and thereby
shows a compound that has a greater amount of intermolecular forces: it has the highest
boiling point of the two compounds approximately 120C.

Part 2: Fractional distillation is a process that can be described as the separation of a mixture
into its components parts, and doing so by separating chemical compounds by their boiling
point. By adding a fractioning column in Fractional Distillation, we have the ability to create a
pure mixture. The texture of the column and its packing material will make place for a series of
condensations and evaporations to happen in order to enrich the vapor in the lower boiling
component. Each condensation-vaporization cycle enriches the vapor in 2-propanol and returns
some condensate, enriched in 1-butanol, to the distilling flask. Enough cycles will result in an
effective separation of the vapors. As viewed earlier, the 2-propanol with the lowest boiling
point (approximately 90C) will evaporate first and the 1-butanol with the highest boiling point
of the two compounds (approximately 120C) will evaporate last. The peak in temperature that
begins at approximately 14mL shows the evident separation between the two compounds
boiling points.

Source of Errors:
CHM 1321D- Organic Chemistry
A number of various sources of errors could lead to slightly skewed results during this lab. The
first source of error could have been the distilled substance: the simple distillation resulted in a
distillate of approximately 1mL more than the wanted 25mL. Another important source of error
that must be discussed is the error (human error) of measurements: reading graduated
equipment or in this particular case graduated cylinders is always a process prone to error.
Being required to stay out of the fume hoods, we are forced to read the measurements at a
distance. Another source of error could be what I mentioned earlier in Observations: the heat
was 80C at first in order to bring the solution to a boil, and then quickly switched to 75C when
we had 5mL of distillate in the receiving flask. A possible source of errors for both distillation
processes could also include inadequately sealed joints in glassware and residual distillate left
in the distillation apparatuses: not tightly sealed joints could have led to vapor loss leading to a
smaller volume of collected distillate.

Questions:

1. It is really important to have liquid flowing back through the fractional column in order
to get a good separation of the compounds. The column in a fractional distillation is
responsible for the increase of the surface area (it provides a surface for the vapor to
condense on as the distillation proceeds)to obtain an even better number of
condensations and vaporizations of the solutions: the compound with the lower boiling
point will evaporate up the column, while the compound that has the higher boiling
point condenses and flows back into the flask in what we could call a cyclic fashion; this
will then lead to a more effective separation of the compounds.

2. A fractionating column can be insulated to provide a smooth temperature gradient.

Maintaining a uniform temperature gradient within a fractionating column is important
because the whole process of distillation heavily relies on the concept of temperature: it
is necessary for proper separation of the components. As the vapor moves up the
column, temperature will decrease away from the heat source; this will result in the
compound with the higher boiling point converting back to liquid and condensing at the
lower area. The temperature gradient uses various condensation-vaporization cycles
throughout the process to separate the different compounds: in the end we then have a
maximized amount of the lower boiling point component in the receiving flask.
CHM 1321D- Organic Chemistry
3. The vapor pressure of benzene at 81C is equal to the atmospheric pressure or
101.325kPa: this is because the boiling point of a compound is defined when its vapor
pressure equals the atmospheric pressure.

4. If we were to increase the atmospheric pressure, the compounds vapor pressure has to
increase to reach an equivalence point: the boiling point will increase as a result.
Applying more pressure to the molecules will make them more rigid; it will then require
more energy to break the bonds and turn the appropriate compound into a gaseous
state. (Gay-Lussas law: as pressure increases, so does temperature).

5. Cooling water must enter the bottom of the condenser and not the top because we
need to assure an efficient cooling: water being filled at the bottom is being filled
against gravity (it is fighting against it). We need to note that it is important that the
condenser fills up with water as this will maximize the condensation of the vapor back
into liquid form: the result is an increased speed and accuracy of the distillation.

6. According to Raoults Law,

P Total = PA NA + PB NB; where P represents the partial pressure of each
compound, and N is the mole fraction of each compound in the mixture. As a result:

P mixture = (350mmHg)(0.75) + (150mmHg)(0.25)

= 300 mmHg
The vapor pressure of a 3:1 mixture of A and B at 95C is 300 mmHg.