SUBLIMATION AND MELTING POINT DETERMINATION OF IMPURE BENZOIC ACID

Hannah Marie G. Herrella, Isabelle Louise F. Ilagan, Myzhel S. Inumerable,

Natasha R. Jain and Tactto B. Kobayashi
Group 5 2CPharmacy Organic Chemistry Laboratory

ABSTRACT
The experiment was conducted to determine the purity of benzoic acid through sublimation and melting point
determination of the impure benzoic acid. Five grams of impure benzoic acid was heated for 10 to 15 minutes to form
colorless needle-like crystals on the inverted watch glass. The crystals (sublimate) was used in calculating the
percentage recovery. The crystals and the pure benzoic acid were then individually packed in capillary tubes for
determining the melting point of the samples with the use of an oil bath and thermometer. A 110 C to 124 C was
obtained indicating that there are impurities. Certain deviations on melting point have occurred maybe because of
mishandlings and contaminations
INTRODUCTION
Sublimation is the process where some solids
can pass directly into vapor phase without
undergoing through a liquid phase. Given the
fact that the vapor can solidify, sublimation may
be an effective purification process. It can be
therefore defined as a technique used to purify
solid mixtures. It is only limited, however, to
those with non-volatile impurities or those that
have lower vapor pressure than the pure
compound. Melting point is often associated with
sublimation when testing purity of compounds.
Melting point is the temperature in which a
solid phase is in equilibrium with the liquid phase.
A substance normally melts at room
temperature. Changing the pressure does not
affect the melting point but boiling points are
greatly affected. An oil bath was preferred
because the melting point of benzoic acid is
higher than the boiling point of water.
Benzoic acid is a white crystalline organic
compound that has a melting point of 122 C and
a boiling point at 247 C. It is naturally found in
many plants and resins. As a microbial agent,
benzoic acid is commonly used in toothpastes,
mouthwashes, cosmetics and deodorants. Large
extent of impurities are present inside the crude
form of benzoic acid because it contains phenyl
and benzyl compounds and also amino acids.
In this experiment, the group should be able to
attain the following objectives: (1) purify benzoic
acid through sublimation, (2) determine and
compare the melting point of the product with a
standard, and (3) calculate the percentage
recovery.
EXPERIMENTAL
A. Compounds tested
5.0 g of impure benzoic acid
Pure benzoic acid
B. Procedure
1. Weighing of Materials
Weigh the evaporating dish and watch
glass in the analytical balance. Weigh 5 g of
impure benzoic acid using a triple beam
balance.
2. Preparation of the capillary tubes
Heat one end of the two capillary tubes
using a Bunsen burner. While heating one
end, rotate it to make it even. Continue
heating until completely closed.
3. Preparation of the hot oil bath set-up
Pour unused cooking oil in a clean
beaker. Place the beaker on top of a tripod
with a wire-gauze and a Bunsen burner
underneath. Secure the capillary tubes with
a piece of thread or rubber band to the
thermometer. Align the closed end of the
capillary tubes with the mercury bulb of the
thermometer. Attach the thermometer in a
clamp and immerse in an oil bath.

Figure 1. Oil Bath Set-Up
4. Purification of Benzoic Acid
Place 5.0 g of impure benzoic acid in a
tared evaporating dish. Cover the dish with
a perforated filter paper. On top of the filter
paper, place an inverted pre-weighed watch
glass. Cool the top of the watch glass with
a moistened tissue paper. Heat for 10 to 15
minutes. Stop heating and cool the set-up.
On the fume hood, carefully invert the pre-
weighed watch glass and collect all the
sublimated in it. Calculate the percentage
recovery.
5. M
e
l
t
i
n
g

P
o
i
n
t

Determination
Grind the sublimate into a fine powder.
Press the open end of the capillary tube
into the powder. Drop the closed end of the
capillary tube down through a glass tubing
several times until it is well-packed with 3-
5 mm of the sublimate. Secure the capillary
tubes with a piece of thread or rubber band
to the thermometer. Align the closed end of
the capillary tubes with the mercury bulb of
the thermometer. Attach the thermometer
in a clamp and immerse in an oil bath and
heat. Stir constantly. Record the
temperature at which the sublimate stars to
melt and when it is completed melted.
RESULTS AND DISCUSSIONS
Sublimation
Through sublimation, the 5.0 g of amorphous
benzoic acid was formed into colorless needle-like
crystals, giving a weight of 0.57 g. Recovery of
the benzoic acid was computed at 11.4% by
dividing the weight of sublimate by the weight of
the impure benzoic acid used, then multiplied to
100. This means that only 11.4% of the sample
was recovered.


Weight of Impure
Benzoic Acid
5 g
Weight of the Watch
Glass + Sublimate
93.0689 g
Weight of the Empty
Watch Glass
92.50 g
Weight of the
Sublimate
0.57 g
Percentage Recovery 11.4%

Table 1. Data obtained from Sublimation
Process
Initially, 5 g of impure benzoic acid was
weighed and had undergone the sublimation
process. A watch glass was pre-weighed and was
found to be weighing 92.50 g. This watch glass
served as the cover for the setup. Also, this is
where the sublimate is contained after the
sublimation process. After the said process, the
watch glass was again weighed and was found to
be weighing 93.0689 g. This means that the
sublimate weighs only 0.57 g.
From the data collected, the Percentage
Recovery may be computed:
%Recovery =
eight of the ubliate
eight of the Ipure enoic cid

=
.
.g

= 11.4%
Based from the data collected before and after
the sublimation process, the percentage recovery
was computed to find out the purity of the
sublimate obtained. It is computed using the
values of the weight of the sublimate over the
weight of the initial sample, impure benzoic acid.
It is then multiplied to 100 to indicate its
percentage.
Based on Table 1, the data here shows that
there was 0.57 g of the sublimate and 5 g of the
impure benzoic acid. Using the formula for
percentage recovery, it indicates that only 11.4%
was recovered. Meaning to say, 88.6% of the
initial sample was made up of impurities.
Melting Point Determination
The crystals and the pure benzoic acid were
then individually packed in capillary tubes
attached to the thermometer. Immersion of the
sample and a standard to an oil bath determined
the melting point of the sample. The standard
started melting at 108C and completely melts at
122C, while the sublimate began to melt at
110C and was fully melted at 124C. Therefore,
the standard has a higher melting point
compared to the sublimate. The difference of _ in
melting point of the two substances indicate that
the sample is not purified well.
Figure 2. Sublimation Process

Temperature
T
1
T
2
Average
Pure Benzoic
Acid
108C 122C 115C
Sublimate 110C 124C 117C



Table 2. Recorded Temperature for Melting Point
Determination
Table 2 notes the differences of the sublimate
and the pure benzoic acid to the temperature at
which they have started and completed melting.
T
1
indicates the temperature at which the two
compounds started to melt. Pure benzoic acid
started to melt at 108C, while the collected
sublimate started to melt at 110C. The average
melting point of T
1
is 115C. The T
2
indicates the
temperature at which the two has completely
melted, pure benzoic acid melted completely at
122C, and the sublimate completely melted at
124C. The average melting point of T
2
is 117C.
Pure benzoic acid is known to have a melting
point of 122C. There is a difference of
approximately 7C between the standard melting
point and the average melting point of the
compound in the experiment. Certain deviations
on melting point have occurred maybe because
of mishandlings and contaminations.
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nd
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University of Colorado website:
http://orgchem.colorado.edu/hndbksupport/dist/
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th
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Table 2. Melting Point Data