FORMAL REPOR T 18, January

2024

PREPARATION AND RECRYSTALLIZATION OF

BENZOIC ACID
Angeles, J., Industan, E.J., Montante, L.M. Piquero, N., Rabino, E.J., Rosero, E.J.

Room 41-506 Science Complex, University of Science and Technology of Southern

Philippines, C.M. Recto Avenue, Lapasan, 9000 Cagayan de Oro City, Philippines
Department of Science and Mathematics, University of Science and Technology of Southern
Philippines, C.M. Recto Ave, Lapasan, Cagayan de Oro City

This report was performed and gathered from the laboratory experiment conducted in
Room 41-506 of the University of Science and Technology of Southern Philippines on
January 08, 2024. This experiment demonstrates the process of recrystallization of benzoic
acid through induced and simultaneous methods to purify an organic compound. The yield of
the recrystallization process can be greatly impacted by the choice of solvent(s) and the
temperature used with the solvent(s) as they directly affect the supersaturation of the solution.
At the end of the experiment students will then be able to use it for these purposes it is
necessary to be able to separate benzoic acid from other reactants obtain a high level of purity
and calculate the percentage recovery. This experiment equips students with crucial
knowledge about creating chemicals, medications, or food products that require high-purity
materials to ensure a safe, high-quality product in the future.

Introduction. Benzoic acid is an aromatic Figure 1.0. Benzoic Acid structure,

carboxylic acid (Figure.1.0.) that forms a consisting of an aromatic ring joined to a
colorless, crystalline solid and can be carboxylic acid.
found naturally in both plants and animals
Recrystallization is one of the most
and some microorganisms it has many
important techniques for an organic
uses including being used to create a
chemist to know. It is a method for
variety of chemicals, antiseptics,
purifying solid compounds which are
plasticizers, and food preservatives.
frequently the products of organic
reactions. The theory of recrystallization
is based on three important concepts which
are compound is always more soluble in
hot solvents than in cold solvents,
molecules have unique solubility
properties, a growing crystal will only
accept similar entities into its lattice.
Recrystallization is a widely used
purification technique for removing
impurities from organic compounds that
are solid at room temperature. This method

1
relies on the observation that the solubility The substance was further filtered using
of a compound in a solvent generally filter paper and a funnel. A funnel stand
increases with temperature. Conversely, as was also used to support and hold the
a solution cools the solubility of a funnel in place during the laboratory
compound will decrease until the solution procedure. Last, the glassware is rinsed
becomes saturated and crystals form. using a wash bottle.
Moreover, recrystallization can produce
Observations. Preparation and
very pure compounds. The choice of
Recrystallization of Benzoic Acid is a
recrystallization solvent is critical. A good
commonly performed experiment in
recrystallization solvent will not dissolve
organic chemistry that involves the
the solid compound at low temperatures
synthesis and purification of benzoic acid.
but will dissolve it at high temperatures.
Benzoic acid is a crystalline solid that is
The cold solvent also needs to dissolve the
widely used as a food preservative and in
impurities. A typical recrystallization
various other applications.
procedure involves dissolving the impure
solid in a minimal amount of boiling
solvent, followed by a cooling period. If
insoluble impurities are found in the
sample during heating, additional steps
(hot-gravity filtration) are taken to remove
them before cooling. After the hot solution
cools and reaches the saturation point,
small seed crystals of the compound will
form in the solution. Slowly, additional
molecules of the compound attach to the
seed crystal and the crystals grow. Since
molecules in the crystals typically have a Figure 1.1. Stirring the Sodium Benzoate
greater affinity for other molecules of the and Hydrochloric Acid to form Benzoic
same type than they do for any impurities, Acid
the process of crystal formation gives rise
to relatively pure crystals. In this experiment, benzoic acid is
prepared by the acidification of sodium
Apparatus. The solution was combined benzoate with hydrochloric acid. The
and heated using a magnetic stirrer and hot reaction yields benzoic acid as the main
plate, respectively. To cover the beaker product, along with other by-products. As
containing the crystallized substance, a the solution was stored, it became cloudy
watch glass was used. A top loading in texture, and precipitates formed. The
balance was used to weigh 2.0 grams of reaction mixture is then cooled to allow
sodium benzoate, which was then crystallization.
transferred to a 100-mL beaker. The
volume of 10.0 mL of deionized (DI)
water was then measured using a
graduated cylinder. The sodium benzoate
was completely dissolved using a stirring
rod. The liquid was cooled in an ice bath
for fifteen minutes to allow crystallization,
and the pH was measured using a pH strip.

2
 HCl 5 mL of 3 M
Deionized (DI) 10
water (mL)
Figure 1.2. The reaction of Sodium Percent Recovery 39.6
Benzoate and Hydrochloric Acid (%)

After the initial preparation, the second Dissolving the initial benzoic acid
part of the experiment involves the in heated water should also allow most
recrystallization of the crude benzoic acid impurities to be dissolved into the solution
to obtain pure, high-quality crystals. as well and to be vacuumed away during
Recrystallization is a common technique filtration. After cooling the solution and
used to purify solid compounds in organic allowing the crystalline solid to form, the
chemistry. It involves dissolving the solid crystals are washed to remove additional
in a suitable solvent at an elevated impurities and allow those to be vacuumed
temperature and then allowing the solution away as well.
to cool slowly, causing the desired
compound to crystallize out. The crystals
are then collected by filtration, washed
with a cold solvent to remove impurities,
and dried to obtain pure benzoic acid.

One important observation in this

experiment is the formation of well-
defined crystals during the
recrystallization process. The slow cooling
of the solution promotes the orderly
arrangement of benzoic acid molecules, Figure 1.3. The Formation of
leading to the formation of regular crystal Crystallization
lattice structures. The appearance of these
crystals, such as their size, shape, and As shown in the table above, the initial
clarity, can provide valuable information mass of benzoate (C7H5NaO2) acid is
about the purity and quality of the benzoic 2.02 grams and after the addition of the 5
acid obtained. mL of 3 mmol mL- HCl and 10 mL water,
the final mass of benzoic acid is 0.80
Discussion and Result. grams which yielded to 39.6 % recovery.

Table 1.0. Known Values weight of recovered crystals

% Recovery= x 100 %
Initial Mass 2.02 weight of sodium benzoate
Sodium Benzoate (1)
(g)
Mass of Filter 1.30 Overall, the results are consistent with
Paper (g) expectations. There was some mass loss
Final Mass Benzoic 2.10 throughout the operation, although the
Acid + Filter Paper purpose was to remove contaminants,
(g) which could account for some of the loss.
Final Mass of 0.80 g
Benzoic Acid (g)

3
Conclusion. In conclusion, Experiment m_term=Benzoic+acid&msclkid=d2b7f72
No. 3 involving the Preparation and 242bc18f37d70928a1c93a789
Recrystallization of Benzoic Acid was
successfully conducted to synthesize and Studocu. (n.d.). Recrystallization of
purify benzoic acid through a series of Benzoic Acid - Experiment 2:
chemical reactions and crystallization Recrystallization of Benzoic Acid -
techniques. Studocu.
https://www.studocu.com/en-us/document/
The initial preparation, which involved the university-of-alabama-in-huntsville/
acidification of sodium benzoate with organic-chemistry-lab-ii/recrystallization-
hydrochloric acid, resulted in the of-benzoic-acid-lab-report/12753691
formation of a cloudy solution with
The recrystallization of benzoic acid.
precipitates. Subsequent cooling of the
(n.d.).
reaction mixture facilitated the
https://sites.pitt.edu/~ceder/lab3/exp3text_
crystallization of benzoic acid, marking
benzoic.html
the first step in the purification process.
The recrystallization stage was crucial for National Center for Biotechnology
obtaining high-quality crystals of benzoic Information. (2022). PubChem Compound
acid. The slow cooling of the solution Summary for CID 243, Benzoic Acid.
promoted the formation of well-defined Retrieved January 17, 2024, from
crystals, indicating an orderly arrangement https://pubchem.ncbi.nlm.nih.gov/compou
of molecules in the crystal lattice structure. nd/benzoic-acid
The appearance of the crystals, including
their size, shape, and clarity, served as a
visual indicator of the purity achieved
during the recrystallization process. The
successful isolation of pure benzoic acid
was confirmed through the meticulous
filtration, washing, and drying steps.

Overall, the experiment provided valuable

hands-on experience in the synthesis and
purification of organic compounds, with a
focus on the importance of crystallization
techniques in obtaining high-purity
substances for various applications,
including the production of benzoic acid
for food preservation.

References

TargetMol. (n.d.). Benzoic acid.

TargetMol.
https://www.targetmol.com/compound/Ben
zoic%20acid?
utm_source=Bing&utm_medium=CPC&ut