EXPERIMENT 3

RECRYSTALLIZATION
Objective:
To purify a compound by recrystallization.
To evaluate the effectiveness of the recrystallization by comparing by comparing melting
points.

Introduction:
A solid sample can be purified through the process called recrystallization. In this process,
impurities are dissolved out of the sample. Melting point can use to determine the purity of
the sample. The melting point method is used because an impure solid melts at a lower
temperature and over a wider range. Recrystallization is often project as an art because the
master crystallizer knows just when to add a little more solvent, just when to stop heating,
and seems to be able to conjure beautiful crystalline samples from nasty materials. However
most of us are able to achieve a good result by following some simple guidelines.
 Choosing the solvent
And essential characteristic of a successful solvent is that the compound is soluble in hot
solvent but insoluble in cold solvent. A test can be performed with small amount of
material in test tube and few drops of solvent added. If the material proves insoluble then
the tube is heated to see if the material will dissolve at higher temperature. If the material
is insoluble at high temperature, a little more solvent can be add ,drop by drop whether
dissolution of solute will occur in large volume of solvent. A solvent should be rejected
if the material appears readily soluble in cold solvent , is not soluble to any appreciable
extent in hot solvent even when the volume of solvent increased. Choosing the solvent
ensure success, all that follows in manipulation.
 Dissolving the sample
The solid sample is introduced, together with around 75% of amount of solvent thought to
be required. It is always advisable to err on the side of using less solvent at this stage. The
flask is heated on the hot plate until dissolution of solute is complete. Additional solvent
can be added to hot solution as necessary to ensure complete dissolution. Ensure the hot
solution is saturated and will deposit crystalline material once it is cooled.
 Hot filtration
Once the solution is fully dissolved, he remaining impurities can be removed by filtering
the hot solution through filter paper folded into cone. A problem here is that the solution
will cool rapidly as soon as the flask is removed from the hot plate. To overcome it, use
stemless funnel and place it on top of beaker contains recrystallization solvent. The
beaker is placed on the hot plate and boiling solvent serves to heat funnel and prevent the
solute from crystallising during filtration process.
 Cooling
Cool the filtered solution to form crystals. Fast cooling will tend to generate more crystal
and slow cooling might allow larger crystals to form. To ensure maximum recovery of
material the solution should be cooled in an ice bath after solution has allow to be cool.
 Cold filtration
Once the crystallization process is judged to complete, the crystals need to be collected by
suction-filtration. It is preferable that all the crystalline material is transferred to the
funnel as a suspension in the crystallisation solvent. It is always hard to get all the crystals
moving freely by swirling the flask and occasionally it will be necessary to add more ice
solvent in order to transfer the last of the crystalline material.
 Washing the crystals
The collected crystals should be washed with a little more ice-cold solvent to remove
final soluble impurities left on the surface. The solvent used for washing must be as cold
as possible to reduce losses from crystals re-dissolving.
 Drying the crystals
Once the crystal have been collected, they can dried by continuing to draw air over them
for few minutes. Spread the dry crystals on filter paper to allow the solvent to evaporate
(kgreine, 2015).

Materials and apparatus:

Boiling chips, Benzoic acid, Charcoal
Erlenmeyer flask (125mL), short-stemmed funnel, Buchner funnel , Hot plate

Procedure:
1) 2.0g of crude benzoic acid was weighed into 125mL of Erlenmeyer flask.
2) Heat 100-200mL of water to boil in beaker on hot plate (boiling chips).
3) Heat an Erlenmeyer flask with little water (with boiling chips).
4) Few boiling chips were added to benzoic acid followed by hot water until benzoic
acid dissolved.
5) Decolorizing charcoal was added if there is present of coloured impurities.
6) Hot solution were filtered through the filter paper into heated flask.
7) Removed the solution of benzoic acid from hot plate and allow to cool.
8) Crystals growing in the solution was observed after few minutes.
9) After 15 minutes, flask was cooled in the ice bath.
10) Crystals were collected by filtration using Buchner funnel.
11) Filter paper was wet with ice cold water before poured the crystal.
12) Filter paper with crystals was transferred to a fresh filter paper to dry.
13) The percentage recovery (%) and the melting point was determined once the crystal
dried.
14) Purified benzoic acid were then labelled.
Results and calculations:
Compound Benzoic acid crystal
Initial weight 2.10g
Watch glass + Precipitate 24.91g
Watch glass 23.82g
Weight recovered 1.09g
Product recovered 124˚C
Percentage recovery (%) 51.9%
Relative accuracy of melting point 101.63%

Melting point of benzoic acid:

123˚ C +125 ˚ C
2
= 124˚C

Percentage recovery of crystal benzoic acid:

weight of compound recovered

×100 %
weight of compound you started with
1.09 g
×100 %
2.10 g

= 51.9%

Relative accuracy of melting point of crystal benzoic acid:

melting point of compound recovered

×100 %
melting point of pure compound

124 ˚ C
× 100%
122˚ C

= 101
Discussion:
The percentage recovery of benzoic acid is 51.9% due to the product loss during experiment.
Larger volume of water is added in the experiment to enable the product to dissolve more
easily and also effect the percentage of recovery of recrystallized benzoic acid. The initial
weight of benzoic acid used in the experiment is about 2.10g. Furthermore, the melting range
of benzoic acid is 123˚C and 125˚C. The melting point of benzoic acid is 124˚C. the benzoic
acid recrystallized in the filter paper during hot filtration. The additional hot water is added to
dissolve the benzoic acid crystals in the filter paper which will then causes the solution to be
more diluted.
Decolorizing charcoal added if coloured impurities present is function to provide vacant sites
to the organic compounds to accommodate to it in which it removes the unwanted coloured
impurities. This also causes loss of products in the experiment as some of the benzoic acid
will be absorbed onto the surface of charcoal. Generally, a little amount of charcoal is
sufficiently to remove the coloured impurities. Otherwise, excess charcoal will cause the
products to remove together with the coloured impurities.
In this experiment, the benzoic acid is dissolved in hot water while only a little amount of
benzoic acid dissolve in cold water. The benzoic acid does not dissolve completely in cold
water because of its hydrophobic benzene ring. However, the carboxyl group, -COOH that
attached to benzene ring allow some of the benzene ring soluble in water. In hot solution, the
increase in temperature causes the water molecules to penetrate through the benzoic acid
solid. Hence, solubilization of benzoic acid occur. Charcoal and other impurities in the
mixture cannot dissolve in water so water is a good solvent choosen in the experiments.
The boiling chips were added in the experiment too. Boiling chips create a space that allow
the bubbles which can prevent bumping and boiling over the mixture so that the loss of
solution can be avoided even it is boiled. The boiling chips must be added before the boiling
of the mixture. This is because adding boiling chips to a solution near its boiling point will
induce flash boiling as well. The boiling chips will not soluble in the solvent and hence they
can be filtered out using filter paper.
During the hot filtration, most of the charcoal powders were removed and stay on the filter
paper while the benzoic acid solution pass through the filter paper and goes into the conical
flask. During the cooling process, slow cooling the hot solution was allowed to cool slowly to
the room temperature. And they only immersed in an ice-bath. The solution should be
protected from contaminants by covering with a piece of filter paper. Fast cooling always
produce relatively small crystals because the particles do not have sufficient time to arrange
themselves in a proper conformation. So, it is not advisable to cool down the hot solution
immediately in ice-bath. The small size of crystals form may trap impurities easily. In the
other hand, slow cooling allowed the molecules to interact and arrange themselves properly
and hence they form larger size of crystals. But, large molecules may causes some solvent
being trapped inside the crystals.
During the cold filtration, the water soluble impurities that might dissolve in water which was
filtered out through the suction filtration. However, some of the impurities might trapped on
the surface of benzoic acid crystals, so a small volume of ice-cold water should be used to
wash the benzoic acid crystals to dissolve the particular impurities. The crystals was then
dried in the oven at 100˚C. A fresh piece of filter paper can be used to place under the filter
paper with benzoic acid crystals.

The purity of the crystal can be determined by its melting point. A narrow range of melting
point indicates high purity of the sample, otherwise broad range of melting point indicates
presence of impurities in the crystals(Recrystallization, 2011).

Precautions:
o The mixture is warmed slowly to facilitate crystallization process.
o The filter paper must be moistened before filtration with chosen solvent.
o Suction filtration must be done gently.
o Excess addition of decolorizing charcoal must avoided.
o Wear laboratory coats, goggles and gloves once the experiment starts.
o Wear cotton cloth during transfer the hot water in beaker on hot plate.
o Use a fluted filter paper as it increase surface area for solvent to flow(Principles of
Recrystallization, 2019).

Conclusion:
From the experiment, the melting point of recovered benzoic acid obtained experimentally is
124˚C. Compare to the pure benzoic acid with 122˚C of melting point, the relative accuracy
of meting point of benzoic acid is 101.63%. This means that the compound is slightly
contaminated with impurities which cause by charcoal powder or the water molecules which
trapped inside the benzoic acid crystals.
Reference:

kgreine (2015) Org lab recrystallization lab report final, Slideshare.net. Available at:
https://www.slideshare.net/kgreine/org-lab-recrystallization-lab-report-final (Accessed: March 8, 2019).

‌ ecrystallization (2011) Blogspot.com. Available at:

R
http://1chemistry.blogspot.com/2011/08/recrystallization.html (Accessed: March 8, 2019).

Principles of Recrystallization (2019) Scribd. Available at:

https://www.scribd.com/presentation/311749825/Principles-of-Recrystallization (Accessed: March 8,
2019).

Recrystallization (2019) Wiredchemist.com. Available at:

http://www.wiredchemist.com/chemistry/instructional/laboratory-tutorials/recrystallization (Accessed:
March 8, 2019).