UNIVERSITI KUALA LUMPUR

MALAYSIAN INSTITUTE OF CHEMICAL BIOENGINEERING

TECHNOLOGY
LABORATORY REPORT COVER PAGE

SECTION A – To be filled up by Student

Subject Code & Subject CPB21404 SEPARATION PROCESS

Title of Experiment RECRYSTALLIZATION OF BENZOIC ACID
Date of Experiment 24 September 2018 Date of Submission 1 October 2018
Name & ID No. 1) MOHAMAD IMAD EL KHEIR 55213117149
2) NIK NOR SYAHIDA AZWA BT NIK ZULKERNAIN 55213117116
Group No: ( )
3) IZZATI SYAKIRAH BT MOHD YUSOFF 55213117120
4) MUHAMMAD ZAKWAN B. ZAIDI 55213117161
5) MUHAMMAD IMRAN AZRIE B. ABU BAKAR 55213117156
Name of Lecturer DR. NOR SHAHIRAH MOHD NASIR
*Penalty:
• For any late of submission, the mark will be reduced by 5% per day to a maximum of 3 days, after which it
will NOT BE ACCEPTED.
• Plagiarism will not be tolerated and will be given ZERO.
SECTION B – To be filled up by Lecturer

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(1) (2) (3) (4) (5)
Report format (5%) 1 2 3 4 5
1.Organization of the report.
Summary (10%) – max 1 page
1.Brief review on the objectives of the experiment, major 2 4 6 8 10
findings and significant conclusions
Introduction & Theory (10%) – max 2 pages
1. State the background to the experiment conducted. 2 4 6 8 10
2. Summary of theories including formulations related to
the experimental work.
Data & Results (10%)
1. Data are presented as deemed suitable with complete 2 4 6 8 10
labels and units.
Analysis & Discussion (40%)
1. Explanations of the referred table and figure are
presented after the table and figure 8 16 24 32 40
2. Discuss on the findings and relations to the theory and
objective of experiment
Conclusion & Recommendation (10%)
1.Summary of the results to relate the findings or results
with the theory applicable to the experimental 2 4 6 8 10
2.Suggest improvements in apparatus or measurement
procedure, or experimental procedures for future
References & Appendices (5%)
1. Cite references in the text.
2. References taken from books, journals and articles. 1 2 3 4 5
References from website are not recommended.
3. Put raw data and sample calculation.
TOTAL (90%)

Laboratory Psychomotor Assessment (10%) Student 1 Student 3

Individual practical skills
Student 2 Student 4

Student 1 Student 3
TOTAL (100%)
Student 2 Student 4
Date of Submission:
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TABLE OF CONTENTS

SUMMARY .................................................................................................................................... 3

INTRODUCTION & THEORY ..................................................................................................... 4

RESULTS ....................................................................................................................................... 6

DISCUSSION ................................................................................................................................. 7

CONCLUSION ............................................................................................................................... 9

RECOMMENDATION ................................................................................................................ 10

REFERENCE ................................................................................................................................ 11

APPENDIX ................................................................................................................................... 12
SUMMARY

Recrystallization is a process to purify the impure solvent. The objectives of this

experiment was to study how to purify benzoic acid by crystallization and to determine the melting
point of pure benzoic acid. In this experiment, impure benzoic acid was used to obtain the pure
substance which it will formed crystal. The benzoic acid was heat up on a hot plate until it is solute
(20-25 minutes). Then, the sample was filtered with filter paper to obtain the pure substance in a
conical flask. The pure substance was heat up for about 5 more minutes before let it cooled in ice.
After it was been cooled, the crystal will formed and it was been filtered by using Hirsch/ Buchner
funnel to obtain the crystal. The crystal was then dried for a round 15 hours before taking the
weight of the sample. Based on the result, the percentage of recovery for the sample was 18% and
the melting point of the sample was 121ºC to 127 ºC. According to the results, it shows that the
recovery of the sample 0.18 g because there are different solubility of solute in solvent. Compound
with less solubility will crystallize first. The impure benzoic acid has higher melting point than
pure benzoic acid because pure substance has fixed melting point. In this experiment, there a few
errors might had occurred such as human error, zero error and technical error.

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INTRODUCTION & THEORY

A pure compound is a homogeneous sample consisting only of molecules having the same
structure. However, substances believed to be pure on the basis of certain criteria may actually
contain small amounts of contaminants. Indeed, the presence of impurities in what were believed
to be pure compounds has sometimes led to incorrect structural assignments and scientific
conclusions. The possibility of making such errors was of particular concern prior to the advent
of the powerful chromatographic and spectral techniques that have been developed since the
1950s. It is now relatively easy for the chemist to purify solids and liquids and to demonstrate their
purity.

A compound formed in a chemical reaction or extracted from some natural source is rarely
pure when initially isolated. For example, a chemical transformation intended to produce a single
product almost invariably yields a reaction mixture containing a number of contaminants. These
may include the products of side reactions proceeding concurrently with the main reaction,
unchanged starting materials, inorganic materials, and solvents. Unfortunately, even chemicals
purchased commercially are not always pure, owing to the expense of the needed purification
process or to decomposition that may occur during storage.

Recrystallization of solids is a valuable technique to master because it is one of the methods

used most often for purification of solids. Other techniques for purifying solids include
sublimation, extraction and chromatography. Nevertheless, even when one of these alternative
methods of purification has been used, the solid material thus isolated may still be recrystallized
to achieve the highest possible state of purity.

The process of recrystallization involves dissolution of the solid in an appropriate solvent

at an elevated temperature and the subsequent re-formation of the crystals upon cooling, so that
any impurities remain in solution. This technique, called solution re crystallization, is discussed
here. An alternative approach involves melting the solid in the absence of solvent and then
allowing the crystals to re-form so that impurities are left in the melt. This method is seldom used
in the organic laboratory because the crystals often form out of a viscous oil that contains the
impurities and from which it is difficult to separate the desired pure solid. It is interesting to note,
however, that this is the technique used to prepare the high-purity single crystals of silicon used
in computer chips.

4
 Almost all solids are more soluble in a hot than in a cold solvent, and solution
crystallization takes advantage of this fact. Thus, if a solid is first dissolved in an amount of hot
solvent insufficient to dissolve it when cold, crystals should form when the hot solution is allowed
to cool. The extent of precipitation of the solid depends on the difference in its solubility in the
particular solvent at temperatures between the extremes used. The upper extreme is determined by
the boiling point of the solvent, whereas the lower limit is usually dictated by experimental
convenience. For example, an ice-water bath is often used to cool the solution to 0 °C, whereas
ice-salt and Dry Ice-acetone baths are commonly used to cool solutions to -20 °C and -78 °C,
respectively. The solid should be recovered with greater efficiency at these temperatures, provided
the solvent itself does not freeze.

If the impurities present in the original solid mixture have dissolved and remain dissolved
after the solution is cooled, isolation of the crystals that have formed should ideally provide pure
material. Alternatively, the impurities may not dissolve at all in the hot solution and may be
removed by filtration before the solution is cooled. The crystals that subsequently form should be
purer than the original solid mixture. Solution recrystallization is seldom quite so simple in
practice, but these two idealized generalizations do outline the basic principles of the technique.

Even after a solid has been recrystallized, it may still not be pure. Thus, it is important to
determine the purity of the sample, and one of the easiest methods to do this is by determining the
melting point of the solid.

The type of solid used in this experiment was Benzoic Acid. According to theory, Benzoic
acid is a crystalline solid that has high solubility in hot water. Thus, an impure sample of benzoic
acid is dissolved in hot water and then filtered to remove insoluble impurities. After the pure
benzoic acid is obtained, the following formula is used to calculate the percentage recovered.

𝑊𝑒𝑖𝑔ℎ𝑡 𝑜𝑓 𝐵𝑒𝑛𝑧𝑜𝑖𝑐 𝐴𝑐𝑖𝑑 𝐴𝑓𝑡𝑒𝑟 𝑅𝑒𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑙𝑖𝑧𝑎𝑡𝑖𝑜𝑛

% 𝑅𝐸𝐶𝑂𝑉𝐸𝑅𝐸𝐷 = × 100%
𝑊𝑒𝑖𝑔ℎ𝑡 𝑜𝑓 𝐵𝑒𝑛𝑧𝑜𝑖𝑐 𝐴𝑐𝑖𝑑 𝐵𝑒𝑓𝑜𝑟𝑒 𝑅𝑒𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑙𝑖𝑧𝑎𝑡𝑖𝑜𝑛

5
RESULTS

1. Data on the impure Benzoic Acid

Mass of the benzoic acid + weighing paper 1.96 g

Mass of weighing paper 0.96 g
Mass of impure benzoic acid 1.00 g

2. Data for recrystallized benzoic acid

Mass of recrystallized benzoic acid + weighing paper 1.14 g

Mass of weighing paper 0.96 g
Mass of recrystallized benzoic acid 0.18 g
Percentage recovery 18%
Melting point of recrystallized benzoic acid 121-127 ̊C

3. Melting point of recrystallized benzoic acid (Theory):

The recrystallization process depends on the two principle which are the fact that
substances tend to be more soluble in a hot solvent than in cold solvent and that each solute
tends to behave as though it we alone in the solvent. Using the correct solvent is very
important in the process because the solute must be insoluble in the solvent at room
temperature, and as the solvent’s temperature increase, the solute’s solubility also increase.
An excellent substance for this process is benzoic acid because the melting point of benzoic
acid is approximately 122 ̊C (2002, Gilbert and Martin CD-Rom, MSDS Data). It is a
molecular crystal rather than ionic crystal. Impure benzoic acid contains of the impurities
phthalic acid and benzyl benzoate. So, if the impure sample is dissolved in a minimal
volume of hot solvent (hot water) and filtered to remove insoluble impurities, the solution
will contain dissolved benzoic acid as well as dissolved impurities.

6
DISCUSSION

This recrystallization of benzoic acid experiment was conducted in order to study how to
purify benzoic acid by crystallization and to determine the melting point of pure benzoic acid.
When organic substances are synthesized in the laboratory or isolated from plants there will be
impurities in that organic substance. Several techniques for purifying these compounds that have
been develop. The most basic of these techniques for the purification of organic solid is
recrystallization. This method relies on the different solubility of solutes in a solvent; compounds
that are less soluble will crystallize first.

For This recrystallization experiment was done using the impure benzoic acid, weighted
at 1.00 g on the 0.96 g weighing paper into the 100 ml conical flask and 15 ml of distilled water
was added. After that, the anti-bumping granules were added into the conical flask about three to
five pieces. The mixture was heated on a hot plate with temperature 100 ̊C until the solvent was
boiled and added successive 2 to 3 ml of water if required and continue boiling until all benzoic
acid has dissolved or apart from insoluble impurities. The fluted filter paper was prepared while
waiting for the solution to boil by put the funnel fitted with fluted filter paper in the oven until it
ready to be used and 20 ml of water was heated in a beaker. The hot mixture of the benzoic acid
was filtered through a fluted filter into a conical flask. Minimum volume of boiling water was
added to re dissolved the crystals and to allow the solution to pass through the funnel if
crystallization occurs on the filter paper. The filtrate was allowed to cool down in an ice-bath and
was filter through Hirsch/ Buchner funnel. Finally the filter paper contain crystal was placed in a
watch glass and leaved for 15 hours. After the crystal dry completely the weight of the pure
benzoic acid recovered was 0.18 g by 18% recovered by using the formula weight of benzoic acid
obtained after recrystallization over by the weight of benzoic acid before recrystallization and
multiply with 100 percent.

7
 A pure compound is a homogenous sample that consisting only of molecules having the
same structures. According to the National Centre for Biotechnology Information (2018) the
melting point of pure benzoic acid was 122 ̊C while the melting point of recrystallized benzoic
acid was 121 to 127 ̊C. Pure benzoic acid has lower melting point than the impure benzoic acid
because a pure substance has a fixed melting point while an impure substance melts over a wide
range of temperature. The melting point of a substance is not the exact point at which it melts but
rather the range of the temperature from when the sample starts to melt until it has completely
melt. So, the greater the range the more impurities are present but a range of less than 1 ̊C indicates
the pure substances. (GlaxoSmithKline, 2018).

A good recrystallization solvent will dissolve a large amount of the impure compound at
temperature near the boiling point of the solvent and small amount of compound that being
purified should remain in the solution at low temperature. Low solubility at low temperature will
minimizes the amount of purified compound that will lose during the recrystallization. The solvent
should not react with the compound that being purified and it should have the boiling point below
the melting point of the compound being purified because the solid melts before dissolve. (Dr.
Pahlawan, 2015)

There might be some errors that might have occurred during the experiment. During the
cooling and crystallization, the solution should be protected from airborne contaminants by
covering the opening with a piece of filter paper and inverted beaker. Other than that, rapid cooling
by immersing the flask in water or an ice-water bath in undesirable because the crystal formed
tend to be very small and resulting in large surface area and may foster adsorption of impurities
from the solution. The formation of crystal larger than 2 mm should be avoided because some of
the solution may become occluded or trapped within the crystal. Generally, the solution should
not be disturbed as it cools.

8
CONCLUSION

In conclusion, the objectives of the experiment were to purify benzoic acid by

recrystallization and to determine the melting point of pure Benzoic Acid. Based on the results
obtained the weight of the pure benzoic acid recovered was 0.18 g by 18% recovered by using the
formula weight of benzoic acid obtained after recrystallization over by the weight of benzoic acid
before recrystallization and multiply with 100 percent. This is because of the different of solubility
of solute in a solvent. Compound that are less soluble will crystallize first. Pure benzoic acid has
lower melting point than the impure benzoic acid because a pure substance has a fixed melting
point while an impure substance melts over a wide range of temperature. The melting point of a
substance is not the exact point at which it melts but rather the range of the temperature from when
the sample starts to melt until it has completely melted. There were few possible errors that can
occur during the experiment. Firstly, the solution should be protected from airborne contaminants
by covering the opening with a piece of filter paper and inverted beaker. Other than that, the
benzoic acid should be weight properly, if the benzoic acid is not weight properly it might affect
the result. Lastly, rapid cooling by immersing the flask in water or an ice-water bath in undesirable
because the crystal formed tend to be very small and resulting in large surface area and may foster
adsorption of impurities from the solution. Thus, the ideal expected results could be achieved.

9
RECOMMENDATION

To receive a better performance for this experiment, there a few recommendations such as
let the solution in the conical flask that have been filtrate cool down before place in the ice-bath.
This is because the solution is still hot and if it is placed directly to the ice-bath, it will slow down
the recrystallization process. So, let the solution cool down until at room temperature. Next,
properly filtrate the solution that have been cool down in the ice-bath through the Hirsch/Buchner
funnel. Lastly, all the apparatus needs to be clean properly as there is possibility to have chemical
residue in the apparatus from the previous experiment. The chemical used in this experiment will
react with the chemical residue. Thus, it will affect the quality of the product.

10
REFERENCE

GlaxoSmithKline. Recrystallization of benzoic acid and determination of its melting point.

[Online]. [Accessed 27-09-2018]. Available from worldwide web:
sta.ie/perch/resources/lessons/a4gsklessoned.2.pdf

Gilbert and Martin, Experimental Organic Chemistry, 3 rd Ed., 2002, Harcourt College
Publishers, 88-113 and CD Rom.
http://www.emory.edu/CHEMISTRY/mccormick/powerpoint/sld003.htm

National Center for Biotechnology Information. PubChem Compound Database; CID=243,

https://pubchem.ncbi.nlm.nih.gov/compound/243 (accessed Sept. 27, 2018).

Dr. Pahlawan, 2015. Recrystallization of Benzoic Acid. [Online]. [Accessed 27-09-2018].

Available from worldwide web: https://www.slideshare.net/aldawaa/experiment-4-
purification-recrystallization-of-benzoic-acid

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APPENDIX

𝑊𝑒𝑖𝑔ℎ𝑡 𝑜𝑓 𝐵𝑒𝑛𝑧𝑜𝑖𝑐 𝐴𝑐𝑖𝑑 𝐴𝑓𝑡𝑒𝑟 𝑅𝑒𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑙𝑖𝑧𝑎𝑡𝑖𝑜𝑛

% 𝑅𝐸𝐶𝑂𝑉𝐸𝑅𝐸𝐷 = × 100%
𝑊𝑒𝑖𝑔ℎ𝑡 𝑜𝑓 𝐵𝑒𝑛𝑧𝑜𝑖𝑐 𝐴𝑐𝑖𝑑 𝐵𝑒𝑓𝑜𝑟𝑒 𝑅𝑒𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑙𝑖𝑧𝑎𝑡𝑖𝑜𝑛
0.18𝑔
% 𝑅𝐸𝐶𝑂𝑉𝐸𝑅𝐸𝐷 = × 100%
1.00 𝑔
% 𝑅𝐸𝐶𝑂𝑉𝐸𝑅𝐸𝐷 = 18 %

12