Experiment 2: Crystallization and Decolorization

Hanna Shaira Y. Santillan, BS Chemistry

Organic Chemistry Lab/MW 10:30 1:30 PM/OZ 403
Chemistry Department, Adamson University, Ermita, Manila

Abstract
Crystallization was performed to separate the benzoic acid from impurities. Water was
selected as the crystallization solvent in this experiment. Color impurities were removed through
adsorption using a very good adsorbent such as animal charcoal. Benzoic acid was crystallized
using two methods namely slow and rapid crystallization. Between these two methods, it was
determined which is more preferable based on the crystals sizes, yielded quantity, and forms.
Keywords: Crystallization, Solvent, Adsorption, Adsorbent, Nucleus Formation

Introduction
Crystallization is a technique which chemists use to purify solid compounds. It is one of
the fundamental procedures each chemist must master to become proficient in the laboratory
(Colin, 2014). Crystallization refers to the formation of solid crystals from a homogeneous
solution. It is essentially a solid-liquid separation which is one of the most important technique in
separation (The Trustees of Indiana University, 2004).
In this technique, choosing an appropriate solvent for the desired compound must be
considered first. A good solvent should not react with the compound and it should have a boiling
point below the melting point of the compound so that the compound will not melt and will only
dissolve. A proper solvent should also dissolve the desired compound at high temperature but
dissolve only a small amount at room temperature (http://spot.pcc.edu/, n.d.).
The mixture may contain impurities which need to be purified. Impurities are the
unwanted substances that can interfere with the process of crystallization. One type of impurity
is called the color impurity which can easily be removed through adsorption (Zhang, et. al.,
2006). Adsorption is a process that occurs when a gas or liquid solute accumulates on the surface
of a solid or a liquid, forming a molecular or atomic film (www.fpharm.uniba.sk, n.d.). In order
for an adsorption to be successful, the adsorbent must have a high surface area so it will be easier
for it to adsorb the impurity ( Gregg and Sing, 2007). Surface area is the amount of contact
between different reacting molecules. Animal charcoal is the common adsorbent used because it
has a high surface area which a decolorizing agent must have (The Columbia Encyclopedia,
2013).

After removing the impurities, the mixture can now undergone crystallization. There are
two methods of crystallization, the rapid and slow cooling. The rapid cooling is done when the
liquid solution is placed into an ice bath. Meanwhile, slow cooling is done by allowing the liquid
solution to cool alone to room temperature. Nucleus formation should occur to hasten the
formation of crystals (Demar, Faenquil, 2005). Nucleus formation can be induced by scratching
the inner walls of the vessel with a glass rod or through seeding or inoculation
(Kawasaki and Tanaka, 2010).
The objective of this experiment is to separate benzoic acid from impurities through
crystallization and to determine which method between rapid and slow crystallization is more
preferable.

Experimental Section
A 200-mL beaker was filled with 50 mL of distilled water. One gram each of benzoic acid
and sodium chloride were added to the beaker with water. A few drops of congo red was then
added to the mixture. The mixture was heated with constant stirring until all the benzoic acid has
dissolved. A pinch of animal charcoal was added to the mixture and the mixture was heated until
it has boiled for few seconds. The mixture was filtered immediately with the use of a fluted filter
paper. Into two beakers, labeled as Beaker A and Beaker B, the mixture was separated into equal
amounts. Beaker A was covered with watch glass and it was allowed to cool to room temperature
while Beaker B was placed in an ice bath and the mixture was stirred rapidly. When complete
crystallization was achieved, the crystals formed were compared to each other. The crystals were
kept in a desiccator to dry. After a week, the crystals were weighed and percent recovery was
computed.

Results and Discussion

A pure compound is a homogeneous sample consisting only of molecules having the
same structure to each other. This experiment was done to separate benzoic acid from impurities
through crystallization and to determine which method between rapid and slow crystallization is
more preferable. In the first procedure, 1g each of benzoic acid, sodium chloride and congo red
were mixed in a 50 mL water. Water was the solvent used because its boiling point is 100 C
which is lower than the melting point of benzoic acid which is 122.41 C. The mixture was then
heated while stirring. The purpose of heating the mixture is for all the benzoic acid to be
dissolved. Stirring should be done because according to Chemical Equilibrium, if stress is
applied the faster the reaction would occur.

Source:http://chemmovies.unl.
.html

edu/chemistry/smallscale/SS002

Fig. 1 Solubility of Benzoic Acid and NaCl in Water

Figure 1 shows the solubility of benzoic acid and NaCl in water. It shows that benzoic
acid is less likely soluble in water at low temperature and more soluble in water at high
temperature while sodium chloride is soluble in water at either high or low temperature
(http://web.centre.edu/, 2006).
The mixture was obviously red in color because of the addition of congo red. Congo red
is water soluble, yielding a red colloidal solution (http://www.rsc.org/, n.d.). If the desired
compound was expected to be colorless but it has a color then it means that the compound is not
pure. In order for the color impurity to be removed, a pinch of animal charcoal was added to the
mixture with continuous heating until it boils. With the addition of animal charcoal, the red
coloration disappeared because the congo red was already adsorbed by the animal charcoal
(Andrew, 2007). Only a small amount of animal charcoal was added because if too much theres
a possibility that some of the benzoic acid will also be adsorbed, thus, making the recovery of
benzoic acid lesser than its original amount. While the solution is still hot, it was filtered
immediately with a use of fluted filter paper. Fluted filter paper is used because the gaps between
the filter paper and the funnel will increase the filter area and it will make the filtration process
faster. The filtration should be done immediately to avoid formation of crystals on the residue
(http://quiz2.chem.arizona.edu/, n.d.).
After the filtration, the filtrate was divided into two equal amounts (Beaker A and Beaker
B). Beaker A was covered with watch glass and then set aside to cool at room temperature while
Beaker B was placed in an ice bath and stirred rapidly. After cooling down the filtrate, the
recovered crystals in Beaker A were few, large needle-like crystals. The recovered crystals in
Beaker B were many, small granule-like crystals. Beaker A undergone a slow cooling method
which made it a more preferable method than a rapid cooling method.

Source:

http://orgchem.colorado.edu/

Fig. 2 Slow Cooling Method (hexagon-crystals, triangle-impurities)

Figure 2 explains that in slow cooling method, the impurities are less likely to be part of the
crystals formed because as the solution cools down slowly; the impurities will form their more
suitable geometry and will be apart from the pure benzoic acid crystals. Large crystals have less
surface area so the impurities are not easily being attached to the crystals, thus, making the
crystals pure (http://www.ce.gxnu.cn/, n.d.).

Source: http://orgchem.colorado.edu/

Fig. 3 Rapid Cooling Method (hexagon-crystals, triangle-impurities)

Figure 3 explains that the impurities are subjected to be part of the crystallized form
because when the solution is cooled rapidly, it will be hard for the impurities to form their stable
geometry (http://www.ce.gxnu.cn/, n.d.).
After the crystallization, Beaker A and Beaker B was filtered to collect the crystals from
each beaker. Each of the filter papers were then placed in an empty beaker and placed in a
desiccator. When the crystals were already dry, the recovered crystals were then weighed and
crystals from Beaker A were fewer than the crystals recovered in Beaker B.

Conclusion
Crystallization of benzoic acid was successful through either slow or rapid cooling
process. However, the slow cooling method is a more preferable method to be used in
crystallization because it yielded few but larger and purer crystals as compared to the crystals

formed from rapid cooling method. In addition, benzoic acid was successfully separated from
NaCl using water as the solvent and from congo red using animal charcoal as the adsorbent.
References:
Dr. Colin (2014). Elements, Compounds and Mixtures. Website: http://www.gcsescience.com/e6crystallization.htm
The Trustees of Indiana University (2004). Crystallization. Website:
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%20241/Labs/The%20Crystallization%20Procedure.htm
Hongtao Zhang, Ping Yu, Zhen Yuan, Yunbai Luo (2006). The Korean Journal of Chemical Engineering.
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