International University, Vietnam National University - HCMC

School of Biotechnology
Department of Biochemistry

ORGANIC CHEMISTRY LABORATORY

REPORT 2: RECRYSTALLIZATION
INSTRUCTOR: PhD. Hoàng Lê Sơn

TEACHING ASSISTANT: Nguyễn Thanh Phong

DATE OF SUBMISSION: 08-07-2019

Group
member:

1. Trương Thị Ngọc Hằng - BTBCIU16041

2. Võ Minh Hạnh - BTBCIU16083

3. Nguyễn Hồng Anh Phương - BTBCIU16015

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

4. Nguyễn Tấn Phú - BTBCIU16057

I. Abstract
This experiment’s target was to achieve how to perform recrystallization through
two tasks. The first one was recrystallization of crude benzoic acid which had to be careful
to calculate the percentage of the recovery from the initial and final weight of benzoic
acid. From the initial 0.5g of impure Benzoic acid collected, 0.36 g of pure Benzoic acid
were recovered after the recrystallization, demonstrating a 72% recovery. Another task
was recrystallization and identification of unknown compound based on the melting point
determination. As the result, the unknown could be Benzamide with the melting point of
127.6°C. Additionally, the best recrystallization solvent was also important to
comprehend in this technique.

II. Introduction
Recrystallization is the primary method for purifying solid compounds which are
frequently the products of organic reactions. The substance is dissolved in hot solvent as a
way to grow the solubility of the solution and eliminate any impure substances. Then the
solution is cooled in an ice-water bath which decreases the solubility of the solution
causing the pure substance to recrystallize. The process of recrystallization can be broken
down into a number of discrete steps: choosing the solvent, dissolving the sample, hot
filtration, cooling, cold filtration, washing and drying the crystals. Additionally,
recrystallization works most effectively by using the best solvent in which the solute need
to be particularly insoluble at room temperature but much more soluble at higher
temperature.

III. Materials and method

 Materials:
Two 250ml beakers, two 100ml beakers, and one Erlenmeyer flask 125 mL were
used to contain solvent; one cylinder 50 mL was used to measur the amount of water in
dilution process. Mortar and pestle serve a function of finely grinding all compounds,
and stirring rod was used to mix the solution. Equipment includes vacuum filter, filter
paper used to filter, collect pure substance; and hot plate used to heat the solution.

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

 Method:

Part 1: Recrystallization of Benzoic acid

After weighting 0.5g Benzoic acid, transfer it into Erlenmeyer flask and add 20ml
of distilled water. The Erlenmeyer then heated on the heat plate and mixed until it was
dissolved completely, the solution was totally dissolved after reaching 190 degree
Celsius. At the following step, the solution was put on the countertop and covered by a
beaker to prevent any motion and cool down to room temperature before putting in the
refrigerator 10 minutes. When the crystal was formed completely, vacuum filter was
used to filter all the solid.

Besides, the solid may stuck in the wall of the Erlenmeyer, rinsing the
Erlenmeyer and Buchner funnel with distilled water to take as much as possible. After
that, solid on the filter paper was taken out, put on the petri dish and dried. Final step
was weighted and compared to initial amount.

Part 2: Recrystallization and Identification of an Unknown Compound

First step was selection of solvent. 1 gram of unknown substance was dissolved
in three different solutions: water, methanol and ethanol. At the room temperature,
unknown substance was dissolved completely in methanol, ethanol, and remained a
little in water. Therefor, water was used as solvent to recrystallize. The solid was
dissolved after heat to 150 degrees Celsius, but remain some substance that did not
dissolve even heated to 200 degree Celsius after 10 minutes. Therefor, hot filtration is
needed to purify the solution. The hot filtration process must take place in the hot plate
because at the room temperature the recrystallization would occur. After filtering and
collecting pure solution, it was cooled down and cold filtrated as same as part 1. After
collecting solid, Melting Point Apparatus was used to determine the melting point by
adding a small amount of finely powder into capillary tube.

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

IV. Result:
Part 1: Recrystallization of Benzoic acid

Figure 1 : Benzoic acid recrystallization in the Erlenmeye

Figure 2 : Benzoic acid

recrystallization after drying

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

Figure 3: Benzoic acid after recrystallization and its weight

The weight of crystal benzoic acid after recrystallization: m=0.36 g

weight of banzoic acid obtained after recrystallization 0.36

% Recovered= X 100%= x100%
weight of benzoic acid before recrystallizati on 0.5
=72 %

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

Part 2: Recrystallization and Identification of an unknown compound

Figure 4: The solubility of unknown 4 sample in Methanol, Ethanol, and Distilled

Water

Figure 5: After a few seconds, sample in Methanol and Ethanol were soluble

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

 Sample of Distilled water was brought to cool condition to recrystallization

Figure 6: Unknown compound recrystallization after drying

The initial of sample unknown 4 was 1.0 g. The mass of sample unknown 4 after
recrystallization was 0.16 g.

 After recrystallized, determine the melting point

Figure 7: The melting point of unknown 4

The melting point of sample unknown 4 gave 127.6˚C. The sample unknown 4 was
Benzamide

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

V. Discussion:
The first consideration in purifying a solid by recrystallization is to find a
suitable solvent. The ideal properties should be possessed by a recrystallization
solvent: 

The compound should be very soluble at the boiling point of the solvent and
insoluble in the solvent at cold temperature. This difference in solubility at hot versus
cold temperatures is essential for the recrystallization process If the compound is
insoluble in the chosen solvent at high temperatures, then it will not dissolve. If the
compound is very soluble in the solvent at room temperature, then getting the
compound to crystallize in pure form from solution is difficult. 

The unwanted impurities should be either very soluble in the solvent at cold
temperature or insoluble in the hot solvent. In this way, after the impure solid is
dissolved in the hot solvent, any undissolved impurities can be removed by hot
filtration. After the solution cools and the desired compound crystallizes out, any
remaining soluble impurities will remain dissolved in the solvent. That’s why crystals
are washed with additional solvent when collected. 

The solvent should not react with the compound being purified. The desired
compound may be lost during recrystallization if the solvent reacts with the compound.
The solvent should be volatile enough to be easily removed from the solvent after the
compound has crystallized. This allows for easy and rapid drying of the solid compound
after it has been isolated from the solution.

In additional to, the crystals needed to wash with ice after collecting them
because crystals are fairly pure on the inside because of the way they grow, but more
likely to have contaminates on the outside. The solvent probably has to be ice cold to
keep from dissolving the crystals.

Part 1: Recrystallization of Benzoic acid

In this experiment, the weight of crystal benzoic acid after recrystallization:
m=0.36 g

Calculating:

weight of banzoic acid obtained after recrystallization 0.36

% Recovered= X 100%= x100%
weight of benzoic acid before recrystallization 0.5
=72 %

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

The weight of collected crystals is 0.36g which are lower than the initial amount
of Benzoic Acid (0.5g) because of several effects: A small amount of sample might be lost
during transfer them into flask and during boiling compound in the hot plate by using a
stirring rod . Moreover, distilled water used to wear crystals remaining along the wall of
flask. It becomes increasingly difficult to dissolve the last portion. The craft technique
collects compound crystals play a role via losing portion of benzoic acid obtained after
recrystallization (crystals were left on the surface of filter paper). Besides that, the
weight of benzoic acid before crystallization consist of the impurities which stayed
dissolved in the solvent when drying the crystals. After the solution finished boiling and
the impurities were visible the solutions were left to cool a little too long that
crystallization occurred around the impurities which resulted in a little solution to
recrystallize. To correct this mistake, the solution needs to be transferred right after the
solution finishes boiling.

Part 2: Recrystallization
The suitable solvent for recrystallization of unknown compound is determined
by comparing the solubility level of them in the following solvents: water, methanol and
ethanol in two conditions: room temperature and heat condition. When procuring 1g of
the unknown sample and putting in each solvent in room temperature , methanol and
ethanol dissolved unknown sample directly. Water did not dissolve completely
unknown sample (only dissolved partially), so the water needs to be heated to dissolve
the sample completely. That’s the reason why the water is good solvent for
recrystallization. But in our group, the sample did not dissolved completely . That
means the sample has impurity compounds and this sample must be needed hot
filtration. After hot filtration, the impurity compounds would be removed and the
sample will be dissolved completely.

The melting point of unknown compound is 127.6˚C, we look up the value from
the Table 2-1 in the lab manual and figure out that the unknown compound is
Benzamide that has a range of melting point from 128˚C-129˚C , and it is a yellow
powder. We conclude that the impurities in the sample are almost removed as well as
127.6˚C is nearly the narrow range that means the unknown has small impurities.
Because impurities will usually cause the melting-point range to become wider and
melting to occur at lower temperatures than that of a pure compound.

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 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

VI. Conclusion:
After recrystallization, the collected amount of solid was not as much as initial
amount. Recrystallization is a useful method to check the purity of substance, and through
the pure solid, the melting point is determined then identity the unknown substance.

VII. References:
1. Organic Chemistry Laboratory Manual of the experiment 2. Ho Chi Minh:
International University, HCMC, 2018.
2. Mohrig, J., Hammond, C., Schatz F, 2010. Techniques in Organic Chemistry, 3rd
Edition, pp. 183-196.

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