INTERNATIONAL UNIVERSITY

SCHOOL OF BIOTECHNOLOGY

REPORT ORGANIC
CHEMISTRY LABORATORY
Experiment 2

Recrystallization
Group3
Nguyen Phuong Anh Kiet – BTCEIU18053
Vien Duc Huy – BTCEIU18017
Ngo Tram Anh – BTCEIU18078
Nguyen Thi Tuyet Ngan – BTCEIU18062
 INTERNATIONAL UNIVERSITY
DEPARTMENT OF CHEMICAL ENGINEERING

Table of Contents
I. ABSTRACT....................................................3
II. INTRODUCTION.........................................3
III. MATERIALS AND METHODS.................4
1. Materials...................................................4
2. Methods....................................................4
IV. RESULT AND DISCUSSION.....................5
1. Experiment 1............................................5
2. Experiment 2............................................7
V. CONCLUSION...........................................10
VI. REFERENCES..........................................11

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ORGANIC CHEMISTRY LABORATORY - GROUP 3 - EXPERIMENT 2
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I. Abstract:
Purification is of significance in many chemical fields, especially those that require high
accuracy and precision1. In general, there are a plethora of techniques to rid of the unwanted
contaminants within that chemical, and this experiment section number 2 focuses mainly on the
relevant procedure known as recrystallization. Fractional crystallization, or recrystallization, is
specifically composed of six consecutive sub-steps, e.g. solvent screening, trial, boiling, cooling,
vacuum filtration, drying out and grounded in the principle of solubility. That is the reagent’s poor
solubility in one the solvent, and it becomes well dissolved as temperature increases. The
experiment is inclusive of two main parts. That is recrystallizing with two different chemicals,
namely benzoic acid, and an unknown. With respect to the initial part, benzoic acid was thoroughly
solidified under a strict process, and 0.18 out of 0.5 grams of the mentioned chemical was
recovered. For an unknown part, 0.81 grams of the unknown chemical was recrystallized from the
initial amount of 1 gram, and melting point determination with the solidified result is required for
the confirmation of its identity. This group’s result for the given unknown is 2-nitrobenzoic acid
although there is the presence of deviations between the literature and actual data that are further
discussed in the Result and Discussion part.

II. Introduction:
Crystallization is the process that a substance forms a solid particle from the solution when
the temperature decreases. This phenomenon occurs based on the difference in solubility of a
substance at different temperatures. The solution over-saturating at temperature 1 can be
undersaturated or saturated at temperature 2. After heating the solution to temperature 1 and
cooling back to temperature 2, recrystallization occurs.

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Recrystallization is a method to purify a substance. Firstly, the best solvent needs to be

chosen. Based on the “like dissolve like” principle and the structure of the compound, some
solvents can easily be rejected. The best solvent is the solvent that does not disperse the substance
at low temperatures but can dissolve it well at high temperatures. Then, the sample is dissolved at
high temperature and cooled in the ice bath to re-crystallize. Finally, the crystal is taken out by
filtration and treated to be dried-out in the oven. This method can only be used to purify the
substance if the extraneous matter dissolves well in the solvent at low temperature and does not
recrystallize with the substance.

This experiment focuses on highlighting the step-by-step procedure to recrystallize an

impure substance and determine the purity of its by measuring the melting point (experiment 1)
and determine the substance by measuring the melting point (experiment 2).

III. Materials and methods

1. Materials
The chemicals used in this experiment were benzoic acid and an unknownsubstance. The
equipment used for this experiment were 1 balance, 1 Erlenmeyer flask, 1 cylinder, 1 spatula, 1
stirring rod, 1 hot plate, 3 beakers, filter paper, and a Buchner funnel with a vacuum filter.

2. Methods
Experiment 1

Firstly, 0.5g of impure Benzoic acid was obtained in the weighing boat then transferred
into a 125-ml Erlenmeyer flask and add 20 ml distilled water. The performer has to cover the
Erlenmeyer flask with aluminum foil to prevent the vaporization of the solution at the boiling
point. Heating and stirring the solution on the hot plate at 250℃ until the solid dissolves
completely. The next step is to wait for cooling the Erlenmeyer flask to cool in the ice bath for 15
minutes, then separate the crystal by using the Büchner funnel apparatus. The substance later has
to be dried in the oven at 100℃ to remove excess water in the crystal, and finally measured to

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calculate the recovered percentage Furthermore the melting point of the crystal has to be
determined by using the capillary method to check whether the substance is pure or not.

Experiment 2

a. Choosing the best solvent for unknown sample:

After obtaining 0.5g of an unknown sample into 3 separate beakers. We add 20 mL of

water, ethanol, and methanol respectively into 3 beakers to determine the most compatible solvent
for the sample by comparing the solubility. In this section, our group rejects ethanol and methanol
which are the two solvents that dissolve the sample well at room temperature. Therefore, water is
the only most logical choice.

b. Recrystallization the unknown sample

Firstly, 1g of the impure unknown sample was again obtained in the weighing boat then
transferred into a 125-ml Erlenmeyer flask that was later added 40 ml distilled water. Covered
with aluminum foil to prevent the vaporization of the solution at boiling point, the Erlenmeyer
flask is heated and stirred on the hot plate at 100℃ until the solid is homogeneously mingled
completely. The process of cooling the Erlenmeyer flask in the ice bath is followed for 15 minutes
then our group had to separate the crystal by using the Büchner funnel apparatus.. The excess of
moisture is removed by putting the glass watch into the drying oven at 100℃. The sample is further
weighted to figure out the recovered percentage. Finally, measure the melting point of the crystal
by using the capillary method and compare with the possible unknown samples table and
determine the unknown sample.

IV. Results and Discussion

PART 1: Recrystallization of benzoic acid
The initial 0.5 g benzoic acid sample was mostly insoluble in distilled water at room
temperature, and its physical form was white powder. However, the powder gradually dissolved
to completion when the mixture was heated to the boiling point of Benzoic Acid, which is 250℃,

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as shown in (Figure 1.1). Afterward, the mixture was left for cooling in two separate steps. The
first step involved adding 15 mL of distilled water and leaving the mixture rest for 5 minutes, while
the second step was cooling the flask in an ice bath. A drastic difference can be noted between the
two cooling steps. To be more precise, while barely any crystallization was observed in the first
step (Figure 1.2), a large amount of Benzoic Acid solid emerged after the second step had been
conducted. This amount was then collected using vacuum filtration. The crystals were washed with
an additional amount of solvent in this collecting step to remove the soluble impurities that were
still attached on the crystal’s surface after filtration, which would otherwise lead to inaccurate
recovery percentage calculation as well as the melting point determination. It is also noteworthy
that the washing solvent (distilled water) used was cold rather than hot. This is because the Benzoic
Acid was known to be insoluble in distilled water at room temperature, so using a cold washing
solvent minimized the loss by re-dissolving crystals, thus also ensuring higher accuracy in later
calculation. The solid collected is shown in Figure 1.3.

Figure 1.1. Heating of Benzoic Acid mixture. Figure 1.2. Leaving the mixture to rest on countertop.

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Figure 1.3. Collected solid after recrystallization.

A difference in the physical of Benzoic Acid before and after crystallization can be noticed.
While both states share a mutual white color, the initial sample was powderier, whereas the crystals
after re-crystallization were shinier and sharper in texture. The sample was dried in the oven to
evaporate any residual vapors and weighed, which shows 0.18 g in weight. This result was used to
determine the recovery percentage of Benzoic Acid recrystallization, by dividing it with the initial
weight (0.5 g) and this calculation yielded
!.#$
!.%
× 100% = 36% of recovery.

The sample’s melting point was also measure using the melting point apparatus similar to
that of Experiment 1, which yielded 122.9℃ (Figure 1.4).

Figure 1.4. Melting point determination of recrystallized Benzoic Acid

The calculated recovery percentage was only 36% of the initial Benzoic Acid, which
implied that the recrystallization did not go to completion and/or the crystals were improperly

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collected. The first speculation might be due to the short cooling time in the ice bath, which did
not allow the crystal to form completely. The second speculation is made based on the nature of
vacuum filtration, which might leave some crystals sticking on the stirring rod, the flask’s surface
or the edge of the Buchner funnel if not washed carefully, leading to the low recovery percentage.
However, the melting point result (122.9℃) was in good agreement with the literature value from
the laboratory manual (122-123℃), meaning that no or very minimal impurities were obtained
during the whole procedure.
PART 2: Recrystallization and Identification of a Unknown Compound
Before performing re-crystallization of the unknown sample, a solvent determination step
was made. This was a crucial step for the whole following procedure, as an incorrect solvent would
hinder the formation of crystals and thus lead to faulty calculation and unreliable determination of
the unknown sample. A good solvent is characterized by three main factors. The first one is that it
must allow the solute to dissolve at high temperature and hinder dissolving at room temperature,
whose purpose is allowing crystallization at room temperature to fit in the requirement of this
experiment. The second factor lies in the principle “like dissolve like'', where a polar or nonpolar
solute can only dissolve in a solvent with the same polarity. Lastly, the solvent should not react
with the compound of interest, as it would change the structure of the unknown sample before it
could be determined. Taking into account those factors, a test was performed among water,
Ethanol, and Methanol by comparing the solubility of the unknown sample in those solvent at
room and high temperature. The room temperature comparison was conducted first, by dissolving
0.5 g of unknown samples in 20 mL of those solvents, respectively, and the results are shown in
Figure 2.1.

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Figure 2.1. (from left to right) The solubility of unknown samples in Water, Ethanol and Methanol.
It is evident that at room temperature, the unknown sample shows high insolubility in
water, whereas it dissolved almost completely in Ethanol and Methanol. Based on this result, no
further step was implemented, and water was chosen as the solvent in this part’s recrystallization.
0.5 g more of an unknown sample was added to the beaker of water as a solvent, and the
recrystallization procedure was conducted in an identical manner to the first experiment.
Eventually, a sharper, shinier solid than the crude crystals was collected, and its weight (after
drying) along with melting point was measured (Figure 2.2 and 2.3). Note that the actual dried
weight of the sample must be recalculated, by subtracting the weight of the filter paper (0.22 g),
which leads to the results of 0.59 g as weight and 145.1℃ as a melting point. The unknown
sample’s recovery percentage was calculated (similar to the first experiment), which yielded

!.%&
#
× 100% = 59% of recovery.

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Figure 2.2. Dried weight of unknown sample Figure 2.3. Melting point of unknown sample
The calculated recovery percentage was only 59% of the initial unknown sample, although
high, still implied that the recrystallization did not go to completion and/or the crystals were
improperly collected. The speculations for those errors are the same as the ones made in the first
experiment. The noticeable observation in this experiment, however, is the melting point result,
145.1℃. This melting point is compared with the values on table 2-1 of the manual to identify the
unknown sample, yet it did not correspond to any of the reference substances.
The main focus is now shifted to identify the errors that were made during this experiment.
The first speculation was made, that is the crystals reformation was impure, due to errors in
filtration performance. To confirm this, the identity of the unknown sample is revealed by the
Teaching Assistant, which was 2-Nitrobenzoic Acid with the melting point range of 140-142℃.
Had the solid collected after recrystallization contained impurities, its melting point should be
lower than the actual range of 140-142℃, yet the measured melting point is remarkably higher
(145.1℃). This implied that the first speculation was incorrect, and a second speculation was made,
that is the unknown sample provided initially was faulty. In order to confirm this theory, the
melting point of the initial unknown sample before recrystallization was examined, and the result
was 147.3℃ (Figure 2.4), which corresponded to Cholesterol.

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Figure 2.4. Melting point of unknown sample before recrystallization.

This, in fact, contradicted with the information given by the Teaching Assistant regarding
the identity of the sample. A reason for this odd result can be proposed, that is there was some
error with the preparation of the unknown sample, but no further confirmation could be made. If
Cholesterol was taken as the initial identity of the unknown compound, the measured melting point
145.1℃ by experiment could be accepted and reasonably explained. The lower melting point
compared to the literature range (145.1℃ compared to 147-149℃) was most likely caused by
impurities during the recrystallization or collection process, which eventually lowered its melting
point.

V. Conclusion
Recrystallization is a technique that filters off the impurity from the chemical. There is a
prerequisite that the chemical be dissolved in the solvent in the high temperature rather than at the
room temperature. This key feature gives rise to the fact that the chemical molecules that need to
be recrystallized can be solidified when cooling. In the part 1, 0.5 grams of benzoic acid is assigned
and 0.18 of it was retrieved, which makes up the recovery percentage of 36%. While in part 2 this
figure climbs to be around 81%, meaning that there was 0.81 grams out of 1.0 of them regained.
The improvement on the recovery data roots from the option of the rate of cooling. In part 1, the
sample was left at the room temperature and then in the ice bath in 20 minutes. In part 2, the boiling
solution was immediately put in the ice bath at the same given amount of time for the sake of fast
cooling rate. Lastly, regarding the identity of the unknown by the aid of the melting point
determination procedure, it is ultimately predicted to be 2-nitrobenzoic acid with the actual and
literate values of 145.1℃ and 140-142℃ respectively. The huge disagreement between the two

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values are explained by the presence of high impurities that were not fully ridded of, the systematic
errors from the machines, and the false steps that were exercised during the process. Therefore,
recrystallization should be under strict attention and implementation of the performer for fear that
there be contaminants penetration into the obtained solid, as this technique serves the sake of
eliminating impure substances.

VI. REFERENCES
1. Recrystallization
https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook
_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Physical_Propert
ies_of_Matter/Solutions_and_Mixtures/Case_Studies/RECRYSTALLIZATION
(accessed Oct 5, 2020).

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