International University Ho Chi Minh City –VNU

Deparment of Applied Chemistry

REPORT

ORGANIC CHEMISTRY LABORATORY

SEMESTER II (2023-2024)

EXPERIMENT 2
RECRYSTALLIZATION
Instructor: Dr. Le Quang Phong
Teaching assistant: Nguyen Thanh Phong

Section: Wednesday Afternoon

Group 4:

1. Nguyễn Thị Cẩm Tiên BTBCIU20070

2. Nguyễn Hoàng Khánh Ngân BTBCIU20086
3. Đậu Ngọc Anh BTBCIU21042
4. Bùi Ngọc Mai BTBCIU21076
5. Trần Cao Bảo Ngọc BTBCIU21081
6. Đinh Thị Thanh Vân BTBCIU21016

Date of submission: April 3rd, 2024

I. ABSTRACT
This experiment investigated the recrystallization technique, which was a crucial technique for
obtaining high levels of purity in solid compounds. It is frequently used to purify substances that are
produced by chemical reactions in laboratories and industries. Benzoic acid and an unknown sample
were recrystallized in the experiment, after which the process's efficiency was evaluated and the
identity of the unknown could be ascertained using melting point determination. The outcome
demonstrated that both recrystallization processes had low yields—less than 50%. Furthermore, the
near proximity of the melting points of the components made it challenging to identify the unknown
substance. As a result, in order to draw a conclusion, further testing had to be done.

II. INTRODUCTION

Recrystallization is an extraction process for purity solid in which its solubility is considered by the
properties of the solvent used. The process of recrystallization from a solvent to purify a solid depends
on the degree to which various compounds dissolve in a particular solvent. When the substance
dissolves in a solvent, the solute fraction gives permission for crystallization to develop through the
period. This technique can be continued numerous times to achieve the purity of the desired chemicals
as much as possible.

Figure 1. The general steps in recrystallization

The high or low productivity of recrystallization depends on the choice of solvent. The solubility
works well in hot solvents but is nonpolar in cold solvents. When selecting the solvent, the greater the
difference between the degrees of hot and cold temperature, the more product can be obtained via
recrystallization.

This experiment used an Erlenmeyer flask with adequate capacity when dissolving the chemical since
its narrow opening and sloping sides prevent solvent evaporation during heating. The solid sample is
combined with approximately 75% of the amount of solvent that might be required. The heated
solution is then saturated, at which point the crystalline material is created by depositing it after

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cooling. Intractable impurities are the cause of pollutants remaining in the solution even after
additional solvent has been added. This causes the solvent to be removed and hot filtration to be
conducted before continuing. In general, any contaminants that exist in the solution admirably remain
in the solution and not be combined into the developing crystals. Furthermore, the growth of crystals
is a result of the cooling filtration solution. The cooling rate affects the quality of the crystals: rapid
cooling produces more crystals with tiny diameters, whereas gradual cooling may allow larger crystals
to form. The solution that allows room temperature on the bench is usually the best balance between
speed, ease of use, and highest-quality crystals. To obtain high accurate recovery of material,
refrigerate and rate the solution in a bath of cold water after letting it cool to room temperature. Once
the crystallization process is done, the crystals must be collected via suction filtering, also known as
cold filtration. It works best if the crystalline substance is transferred to the funnel as much as feasible
in a suspension in the crystallization solvent, though it can be difficult to keep them flowing freely by
spinning the flask and a more ice-cold solvent is added to transfer the remaining crystalline material.
The collected crystals were rinsed with a little more ice-cold solvent to get rid of any soluble
impurities that might have remained on their surface. In order to reduce losses due to crystal
redissolving, the solvent employed in this last washing should be as cold as feasible. The crystals can
be dried by drawing air over them for a short while after they have been gathered on the suction
funnel. The dried crystals should be placed on filter paper to let any volatile solvent that may still be
present to evaporate.

Additionally, recrystallization is a method that can yield completely pure products. These crystals
could be used for X-ray analysis, which determines the three-dimensional form and structure of
molecules. Recrystallization is also performed in the pharmaceutical business. For example, the
medication Stavudine, which is used to treat HIV. Recrystallization is more commonly used in the
production of rock candy.

III. MATERIAL & METHODS

1. Chemicals and equipment:
a. Chemicals

The experiment involved the use of several chemicals including methanol, ethanol, distilled water,
and an ice pack.

b. Equipment:

The experimental setup consisted of a range of essential equipment. These included a 50mL cylinder,
125mL Erlenmeyer flask, Vacuum filter, Buchner funnel, filter flask, spatula, hot plate, stirring rod,
balance, water bath, and a 50mL beaker.

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 2. Procedure:

a. Recrystallization of Benzoic acid

To conduct the experiment, a 125 mL Erlenmeyer flask should be filled with 0.5 g of crude benzoic
acid. The acid should be dissolved by adding hot water and stirring until it completely dissolves. If
any of the acid particles remain undissolved after placing them on the hot plate, more hot water should
be added until complete dissolution is achieved. Supersaturation can be achieved by carefully cooling
the solution, preferably in an ice bath. If crystallization has not occurred after 10 minutes, the interior
surface of the flask above the solution's level should be scratched using the sharp end of a glass rod.
Once the crystals have fully formed, they should be gathered by filtering the solution through a
Buchner funnel device. the crystals were rinsed with one or two milliliters of cold water to remove
impurities and remove them from the flask. At this stage, the pure benzoic acid will nucleate and
precipitate as crystals out of the solution. After removing the filter paper and crystals from the Buchner
funnel with a spatula and allowing them to dry thoroughly, the dried sample was transferred to a pre-
weighed weighing boat. The recovered crystal of benzoic acid was recorded. This technique allowed
for the desired product to crystallize with selectivity by utilizing benzoic acid's significantly higher
solubility in hot water compared to cold water.

b. Recrystallization and Identification of an Unknown Compound

In order to determine the nature of an unknown compound, a series of steps must be followed. The
first step entailed acquiring a sample from the instructor, and recording its identification number in a
notebook for future reference. Typically, unknown compounds can be crystallized from a variety of
solvents, such as methanol, ethanol, or water. To identify the appropriate solvent for recrystallization,
0.5 grams of the unknown sample should be tested for solubility in each of the aforementioned
solvents at both room and high temperatures. After determining the best solvent for dissolving
substance, it was put in the refrigerator to recrystalize pure compound. Thereafter, the resulting
crystals should be extracted and compared to the dried product's melting point to ascertain the
compound's composition and identity. Finally, the compound should be recrystallized once more in a
beaker to ensure purity.

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IV. RESULTS

Part 1: Recrystallization of Benzoic acid

Figure 2. The benzoic acid sample after the recrystallization process.

Figure 3. The sample of benzoic acid that had been dried after recrystallization.

Table 1. The mass of benzoic acid both prior to and subsequent to the process of recrystallization,
along with other equipment.
Mass Gram (g)
Initial sample 0.5
Filter paper 0.27
Petri dish 0.44
Pure crystal 0.17

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● The weight of pure crystal

Mass of pure crystal = mass of petri dish – mass of filter paper = 0.44g - 0.17g = 0.17g.

● % 𝑹𝒆𝒄𝒐𝒗𝒆𝒓𝒆𝒅

● Melting point: 123.9℃

Observations: The table 1's representation of the recovered percentage outcome, standing at 34%,
signified a substantial dissimilarity in mass loss of up to 66% when juxtaposed with the original
substance's mass. Subsequently, the melting point of recrystallized benzoic acid was measured at
123.9℃.

Part 2: Determining the melting point of compound mixture - Unknown

Figure 4. After shaking 20mL of distilled water, ethanol, and methanol solvents
containing the same unknown sample.

Observations: Following the addition of solvents to three vials harboring 0.5g of an unidentified
sample, the solid was entirely dissolved in MeOH, nearly dissolved in EtOH, and solely dissolved in
H2O. Subsequently, upon mild heating for 1-2 minutes, the sample in the EtOH vial was completely
dissolved, while the sample in the H2O vial dissolved after heating for 7-8 minutes.

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 Figure 5. Recrystallization of an unknown sample in a distilled water solvent.

Figure 6. The unknown sample had been dried after recrystallization.

Table 2. The mass of unknown sample both prior to and subsequent to the process of recrystallization,
along with other equipment.

Mass Gram (g)

Initial sample 0.5

Filter paper 0.25

Petri dish 0.28

Pure crystal 0.03

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● The weight of pure crystal

Mass of pure crystal = mass of petri dish – mass of filter paper = 0.28-0.25=0.03 gram.

● % 𝑹𝒆𝒄𝒐𝒗𝒆𝒓𝒆𝒅

● Melting point: 153.2℃

Observations: The table 2's representation of the recovered percentage outcome, standing at 6%,
indicated a substantial dissimilarity in mass loss of up to 94% when juxtaposed with the original
substance's mass. Subsequently, the melting point of the recrystallized unknown sample was measured
at 153.2℃.

V. DISCUSSION
In organic chemistry, recrystallization is a basic method for purifying solid molecules. This report
discusses the experimental procedure and results of the recrystallization process applied to benzoic
acid. The goal was to achieve exceptionally pure crystals of benzoic acid and an unknown compound
by dissolving impure benzoic acid and an unidentified substance in an appropriate solvent and
allowing them to undergo gradual crystallization. The yields and melting points of the final products
were evaluated to assess the success of the recrystallization process.

The effectiveness of the recrystallization procedure was assessed by examining the yield and melting
point of the acquired crystals of benzoic acid and the unidentified substance. The yield was determined
by calculating the percentage of the recovered product relative to the initial amount of impure benzoic
acid. In the first part of this experiment, a yield of 34% was obtained, indicating that approximately
one-third of the pure benzoic acid was successfully recrystallized. The low yield achieved in this
experiment may be attributed to various factors, including the efficiency of the recrystallization
process, loss during filtration, and experimental errors. Additionally, the slight deviation in the melting
point may indicate the presence of impurities or the formation of a compound with a melting point
different from the literature value. To assess the final product's purity, the crystals' melting point was
measured. Pure benzoic acid typically exhibits a melting point range of approximately 122-123°C. In
this experiment, the obtained crystals displayed a melting point of 123.9°C. The closeness of this value
to the literature value suggests that a high level of purity was achieved.

When the unknown substance was added to the methanol vial, it completely dissolved, indicating that
methanol was highly effective at solubilizing the compound. The substance dissolved almost
completely in the vial containing ethanol, with only a small amount of residue remaining. This

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indicated that ethanol had a relatively good solubility for the unknown substance. However, in the vial
containing water, the substance only partially dissolved, suggesting that water had a lower solubility
for the compound. To further investigate the solubility of the unknown substance, slight heating was
applied to the vials. In the ethanol vial, the sample completely dissolved within 1-2 minutes, indicating
that heating improved the compound's solubility. In contrast, the sample in the water vial required 7-
8 minutes of heating to achieve complete dissolution. This result indicated that the solubility of the
unknown substance in water was significantly improved with heating. Based on the observed solubility
and dissolution behavior, it can be concluded that water was the most suitable solvent for
recrystallizing the unknown substance because the pure compound should be dissolved at high
temperatures. The recrystallization process using water as the solvent was then carried out. The
resulting crystals were filtered, washed, and dried to obtain the pure substance. The yield of the pure
substance was found to be 6%, indicating a relatively small amount of purities in the final product.
This efficiency may be affected by the time of cooling, being not enough for crystalizing full of pure
compound. The melting point of the obtained crystals was determined to be 153.2°C, which closely
matched the literature value for adipic acid (152-153°C) and benzilic acid (150-153°C). From this
melting point, it was not still impossible to identify exact compound, so more experiments should be
performed. These findings highlighted the importance of solvent selection in recrystallization and
demonstrated the effectiveness of water as a solvent for purifying the unknown substance.

When selecting a solvent for recrystallization, there are several properties that are ideally desired.
Firstly, to ensure thorough dissolution, it is crucial that the compound of interest exhibits solubility in
the solvent at elevated temperatures. However, it should have low solubility in the solvent at lower
temperatures to facilitate the formation of pure crystals during cooling.[2] Selectivity is another crucial
factor, and the target chemical should dissolve preferentially in the solvent, leaving contaminants
behind. This selectivity helps separate the desired compound from impurities present in the sample.[3]
Additionally, the boiling point of the solvent must be lower than the melting point of the target
chemical. This ensures that the solvent can easily evaporate during the drying process, leaving behind
pure crystals. Lastly, availability and cost must be considered and the solvent should be readily
available and cost-effective to make the recrystallization process practical and efficient.[3] Based on
the above-mentioned properties, water is often considered a good solvent for recrystallization. It is
widely available, inexpensive, and has a high boiling point, making it suitable for dissolving a wide
range of organic compounds. Additionally, water exhibits selectivity by dissolving impurities to a
lesser extent than the compound of interest, allowing for purification during recrystallization. In this
experiment, the unknown substance was partially dissolved in water, indicating that water could
dissolve some impurities while still dissolving the compound of interest. This selectivity, combined

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with the subsequent crystallization upon cooling, resulted in a yield of pure substance at 6% and a
melting point of 153.2 °C.[2]

VI. CONCLUSION

Recrystallization is a technique used to purify and isolate a desired compound from a solid mixture
based on differences in solubility in a certain solvent, including hot and cold filtration. Besides not
dissolving or less dissolving the impurities at all temperatures, the chosen solvent should be able to
dissolve the desired components when cooling down. The cooling rate can affect the quality of the
purifying process since slow cooling could facilitate the formation of large dimensions and pure
crystals. Additionally, the calculated yields of recrystallization in this experiment were considered low
to moderately low due to the limitations of time and temperature for an optimal process, as well as the
loss of the compound when performing suction filtration. Hence, the recrystallization quality can be
improved in the following experiment by choosing the better organic solvent while performing the
process at the appropriate time and temperature.

VII. REFERENCE

[1] Son, H. L. (2022). Melting point determination. Organic Chemistry Lab Manual (pp. 04-06). Ho
Chi Minh City: International University, HCMC.

[2] Fletcher, B. (n.d.). Recrystallization.

https://sites.pitt.edu/~bandik/organicweb/recrystallization.html

[3] Purifying compounds by recrystallization: Organic chemistry. JoVE. (n.d.).

https://www.jove.com/v/10184/purifying-compounds-by-recrystallization

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VIII. LAB NOTE

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