Purification of Impure Benzoic Acid by Sublimation and Melting Point Determination

Pascual, Patricia A., Ong, Jeniffer Y., Palacios, Pia A., Poquiz, Dominador B., Que,Biehn C., Reyes,
Danielle A.
Group 7, 2B-Pharmacy, Faculty of Pharmacy, University of Santo Tomas


ABSTRACT

In this experiment a technique for the purification of an organic substance was learned and practiced.
Sublimation is used to separate an organic solid from its impurities. This experiment used five grams of
impure benzoic acid which was sublimed; the sublimate was then collected and weighed afterwards for
the percentage recovery. This experiment recovered 20% of the product. The recovered product was then
subjected to melting point determination, which is very useful in identifying the level of purity of the
substance, and the success of the sublimation. Based on the experiment, the melting point of the pure
benzoic acid resulted to 120C to which the sublimate was then compared which began melting at 117C.
Therefore, there were impurities present.

Introduction

Sublimation is the process by which a substance
is heated and transformed from its solid phase to
its gaseous phase without passing through the
intermediate liquid phase.
[1]
The solid is
warmed until its vapor pressure becomes high
enough for it to vaporize and condense as a
solid. Since the vapor can solidify, sublimation
can be used to purify solids.
[2]
This purification
technique is best used for substances that have
significantly higher vapor pressures than their
atmospheric pressure at their melting points.
[3]

There are many advantages for performing
sublimation over other purification methods.
This process is principally used for micro scale
purifications of solids because the loss of
product is typically very minimal. Furthermore,
this technique is appropriate for any heat
sensitive compound (but under high vacuum,
sublimation can be affected under low
temperatures). Thirdly, unlike recrystallization,
solvents are not involved at all in the process,
and most traces of any solvent are effectively
eliminated.
[4]


The melting point of a compound is used by an
organic chemist not only to identify the
compound but also to establish its purity. The
melting point indicates purity in two ways. First,
the purer the material, the higher its melting
point. Second, the purer the material, the
narrower its melting point range.
[2]
Adding
successive amounts of an impurity to a pure
substance generally causes its melting point to
decrease in proportion to the amount of
impurity.
[5]

The objectives of this study are (a) to purify
benzoic acid by sublimation, (b) to determine
and compare the melting point of the product
with a standard and (c) to calculate the
percentage recovery.
[6]


Methodology

The materials used were beaker, Bunsen burner,
capillary tubes, cooking oil (unused), cork,
evaporating dish, iron stand and clamp, iron
ring, rubber band, thermometer, watch glass, and
wire gauze.

The group weighed 5.0 grams of impure benzoic
acid. It was then placed in an evaporating dish.
The evaporating dish must be covered with
perforated filter paper and pre-tarred, inverted
watch glass as shown in figure no. 1.
Masking tape was used to seal the filter paper
and watch glass.


Figure no. 1 Sublimation Set-Up

The set-up was then heated for 15 minutes.
While heating, a tissue paper must be on top of
the watch glass for it to be moistened. After
heating, it must be cooled before opening to
prevent some harmful effects of the sample. The
sublimate, which was the crystals that deposited
in the watch glass, was collected and was
weighed. Percentage recovery is then calculated
using the formula:







The second part of the experiment was the
melting point determination. The sublimate was
placed in a mortar and was grinded into a fine
powder. It was packed in a capillary tube
wherein one end of the capillary tube was
sealed. The pulverized powder must be up to
5mm height. The capillary tube was attached
into a thermometer with a rubber band. The
process of melting point determination was
made by immersing and heating the capillary
tube in an oil bath as shown in figure no. 2. Two
temperatures are noted. The temperature at
which the sublimate starts to melt and the
temperature when it is completely melted.


Figure no. 2 Melting Point Determination Set-
Up

Results and Discussion

Impure benzoic acid, a white amorphous
substance was subjected to sublimation. The
sublimate resulted as colorless, needle-like
crystals as shown in figure no. 3. From 5.0
grams of impure benzoic acid, the sublimate
collected then weighed 1.0 gram.


Figure no. 3 The Sublimate


Table no. 1 Sublimation Experiment
Weight of Impure
Benzoic Acid
5.0 grams
Weight of the watch
glass + Sublimate
94.0 grams
Weight of the watch
glass (empty)
93.0 grams
Weight of the
Sublimate
1.0 gram
Percentage Recovery 20%

Table no. 1 shows the results obtained from the
sublimation experiment. Percentage recovery
was calculated as shown below:

When evaluating whether the sublimation was
successful, a couple of factors must be
considered. One factor is the percentage
recovery. In sublimation, the loss during transfer
is supposed to be minimal, so a successful
sublimation should yield a high percentage of
recovery. As shown above, the group recovered
20% of the product.

Table no. 2 Melting Point Determination
Pure Benzoic
Acid (C)
Sublimate
(C)
T
1
(Temp. at
which it began to
melt)
120 117
T
2
(Temp. at
which it
completely
melted)
126 121

From the data obtained, the melting point range
of the pure benzoic acid was 120C-126C,
while the sublimate was 117C-121C. The
melting point ranges were high. Impurities cause
the melting point to become a melting point
range. The melting point is not anymore sharp,
but a range of values. The more impurities
present, the greater the range of values.
[7]
Furthermore, the reported corresponding melting
point of the pure benzoic acid is 122C-124C.
An impurity causes the melting point to deviate
from the standard.

It makes the magnitude of the
melting point lower. Table 2 also showed the
pure benzoic completely melted at 126C. While
the sublimate completely melted at 121C.
There was a 5C melting point difference. The
melting point difference should not be greater
than at least 1C.

Therefore, the results showed impurities were
present.

References

[1] Hein, M., Best, L.R.,Pattison, S., Arena, S.
(2005). Introduction to General, Organic, and
Biochemistry 8
th
Edition. U.S.A. : John Wiley &
Sons, Inc. P. 302
[2] Pavia, D.L, Lampman, G.M, Kriz, G.S., et
al. (2013). A Microscale Approach to Organic
Laboratory Techniques 5
th
Edition. Pacific
Grove, CA: Thomson-Brook/Cole P.660
[3] Williamson, K.L., Masters, K.M. (2012).
Techniques Labs for Macroscale and Microscale
Organic Experiments 6
th
Edition. Belmont, C.A.:
Brooks/Cole P.50
[4] University of Colorado-Boulder, Department
of Chemistry and Biochemistry. (2003). CU
Boulder organic chemistry undergraduate
courses lab techniques. Retrieved May 30, 2007
from the University of Colorado
http://webapps.utsc.utoronto.ca/chemistryonline/
sublimation.php
[5] Jones, L., and Atkins, P. W.
(2000) Chemistry: molecules, matter, and
change, 4th Ed., New York, W.H. Freeman.
[6] Bathan, G.I., Bayquen, A.V., Cruz, C.T.,
Crisostomo, A.C., De Guia, R.M., Farrow, F.L.,
Pena, G.T., Sarile, A.S., Torres, P.C. (2014).
Laboratory Manual in Organic Chemistry:
Revised Edition. Manila: C&E Publishing, Inc.
[7] Briggs, J. Chemistry O Level Third Edition.
Singapore: Pearson Education P.32