K. B. L. Cablaida / Chemistry 31.

1 (2021) P a g e |1

Recrystallization and melting point determination of benzoic acid

Karl Brylle L. Cablaida
Department of Chemical Engineering, University of the Philippines Diliman, Quezon City, Philippines
Submitted 15 March 2021

ANSWERS TO QUESTIONS solvent at elevated temperatures and sparingly

soluble or insoluble at lower temperatures.
1) How does the use of fluted filter paper hasten b) Theoretically what is the purity of A and B after
filtration? one recrystallization?
Fluted filter paper has more surface area The purity of compound B is 100% with a
through which the solvent can seep and be filtered percent recovery of
compared to the regular three-is-to-one filter
paper. Moreover, the fluted filter paper allows air
to enter the flask along its sides which results in the
equalization of pressure, and thus easier and faster The purity of compound A is
filtration.

2) Explain two techniques that can help prevent with a percent recovery of 100%.
premature recrystallization. What could be the
consequence of premature recrystallization?
Mixture of 2.0 g of A
One technique to prevent premature
and 8.0 g of B
recrystallization is to have the receiving flask for
hot filtration pre-heated with a small amount of
solvent inside. Another technique would be using a Heating
short-stemmed funnel during the filtration. A short-
stemmed funnel ensures that contact between the
filtrate and the glassware will be minimal, thus Cooling of solution
there will be minimal recrystallization of benzoic
acid on the funnel as well. It is important that
techniques like these be done because premature Mother liquor:
Recovered crystals:
2.0 g of A
recrystallization may results in the decrease of 0.1 g of B
7.9 g of B
yield of benzoic acid.

3) A mixture containing 2.0 g of A and 8.0 g of B is to 4) A mixture of three compounds, A, B, and C is

be separated by recrystallization. The components purified using recrystallization method. Their
were purified by single crystallization using 100 solubilities in g/100 mL ethanol are given below.
mL of solvent. Their solubilities are given in the Solvent A B C
table below. Cold 1.05 5.6 4.2
A B Hot 20.5 2.3 3.5
Solvent
Cold Hot Cold Hot a) If a mixture containing 4.0 g each of A, B, and C
Ethanol 0.5 10.0 5.0 20.0 is recrystallized from 100 mL ethanol, which
Acetone 5.0 20.0 0.1 8.0 compound can be obtained pure?
Water 0.6 15.0 0.5 10.0 Compound A can be obtained pure because
a) Which solvent would you choose? Explain your the other compounds will remain in solution
choice by means of a schematic diagram. upon cooling. This is better seen with the use of
I will choose acetone as the solvent because the following schematic diagram.
it possesses the characteristics of an ideal
solvent – that is, the solute is soluble in the

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Mixture of 4.0 g of solvents cannot be used as solvent pairs for the

A, 4.0 g of B, and 4.0 experiment? Explain your answer.
g of B with solvent a) Hexane and water
Hexane is nonpolar while water is polar,
Heating therefore they are immiscible. Because mixed-
solvent recrystallization requires the solvent-
pair to be miscible, hexane and water would not
Mother liquor:
4.0 g of A
Recovered crystals: be a great choice.
1.7 g of B b) Chloroform and diethyl ether
2.3 g of B
0.5 g of C Both are polar compounds, and thus, they
3.5 g of C
are miscible, making them a great choice as
solvent-pair for mixed-solvent recrystallization.
Cooling
c) Acetone and methanol
This solvent-pair is also miscible because
Mother liquor: they are both polar, thus they are a great choice
1.05 g of A Recovered crystals: for use in mixed-solvent recrystallization.
2.3 g of B 2.95 g of A
3.5 g of C
6) What are the advantages/disadvantages of mixed
solvent recrystallization over single solvent
b) If the filtrate from (a) is evaporated to 50 mL,
recrystallization?
which of the compound(s) will separate upon
In the process of recrystallization, it is
cooling? What is its purity?
undeniable that the choice of solvent is a very
Compound A with a 100% purity will
important step. Not all solvents can be considered
obtained, as can be seen in the following
ideal for a certain solute, making the choice for a
schematic diagram.
solvent even more crucial. This is where mixed-
solvent recrystallization comes into play. When
Mother liquor: there is no ideal solvent with appropriate
4.0 g of A dissolving capacity for use in single-solvent
2.3 g of B
3.5 g of C
recrystallization, the use of mixed solvents is often
a convenient approach. For mixed-solvent
50 mL recrystallization, the solute must be soluble in one
ethanol Heating of the solvents and sparingly soluble or insoluble in
the other. These two properties combined
constitute the ideal solvent for single-solvent
Mother liquor: Undissolved
4.0 g of A crystals: recrystallization. This means that there is a higher
1.15 g of B 1.15 g of B percent recovery of the purified desired solute
1.75 g of C 1.75 g of C when mixed-solvent recrystallization is used
compared to its single-solvent counterpart.
However, mixed-solvent recrystallization is more
Cooling
complicated than single-solvent recrystallization,
which means that it requires more attention and
Mother liquor: careful execution. Also, the technique demands use
0.525 g of A Recovered crystals: of more laboratory compounds.
1.15 g of B 3.475 g of A
1.75 g of C
REFERENCES

[1] Klein, D. Organic Chemistry; John Wiley & Sons, Inc:

5) You were asked to perform recrystallization using a USA, 2015.
mixed-solvent system. Which of the following

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 K. B. L. Cablaida / Chemistry 31.1 (2021) P a g e |3

[2] McMurry, J. Foundations of Organic Chemistry;

Cengage Learning: USA, 2010.

[3] Merck. Solvent Miscibility Chart [Online]; n.d.

https://sigmaaldrich.com/content/dam/sigma-aldrich
/research-essentials/solvents/migrationsolvents1/sol
vent-miscibility-rules-chart-ms.pdf (accessed March
14, 2021)

[4] University of Wisconsin-Madison Department of

Chemistry. Recrystallization [Online]; 2014.
http://chem.wisc.edu/deptfiles/genchem/Chm346/pd
f/recrystallization.pdf (accessed March 13, 2021)

Mobile: 09287558531
E-mail address: klcablaida@up.edu.ph