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RECRYSTALLIZATION

AND
DETERMINATION OF BENZOIC ACID

MELTING

POINT

J.V. DE GUZMAN
DEPARTMENT OF CHEMICAL ENGINEERING, COLLEGE OF ENGINEERING
UNIVERSITY OF THE PHILIPPINES, DILIMAN QUEZON CITY, PHILIPPINES
DATE PERFORMED: JANUARY 30, 2015
INSTRUCTORS NAME: ALLAN KENNETH REGUNTON

ANSWERS TO QUESTIONS
1. How does a fluted filter paper hasten filtration? Why is it
advisable to place a small piece of wire between the funnel and the
mouth of the flask during hot filtration?
Compared to a conventional filter paper, fluted filter paper hastens the
filtration by maximizing the contact area between the filter paper and the
solution and minimizing the contact area between the funnel and the filter
paper. The rate of liquid flow through the filter paper increases because the
flutings of the filter paper permits air to enter the flask along its sides
allowing for pressure to rapidly equalize. Placing a small piece of wire
between the funnel and the mouth of flask, on the other hand, relieves any
pressure increase brought by the hot filtrate. The wire prevents formation of
a solvent seal between the flask and the funnel since such seal will block the
vent of air displaced by the filtrate thus relieving the pressure.
2. Enumerate 2 techniques that can help prevent premature
recrystallization. Explain each item. What can be the consequence if
premature recrystallization was not avoided to occur?
a.) Keeping the filtration set-up warm- the hot solution cools as it runs
through the filter allowing crystallization to occur. Warming the funnel and
the filter paper thus prevents the hot solution from crystallizing during
filtration. Heating the receiving flask helps prevent premature
recrystallization as the filtrate accumulates since this produces vapors that
keeps the funnel and filter paper warm thus preventing crystallization.
b.) Pouring the hot solution in small amounts- It prevents
recrystallization since it lessens the solution's time in the filter preventing it
to cool and crystallize. If crystallization already occurs, pouring small amount
of the hot solvent dissolves the solids.
If premature recrystallization was not avoided, it gives a lower percent
yield and a negative error since the sample that prematurely recrystallized
cannot be accounted in the total yield (unknown mass) and thus considered
to be lost sample.

3. A mixture containing 2.0 g of A and 8.0 g of B is to be separated


and the components purified by one crystallization from 100 mL of
solvent. Their solubilities are given in the table below:

Solvent

cold

hot

cold

hot

Ethanol

0.5

10.0

5.0

20.0

Acetone

5.0

20.0

0.1

8.0

water

0.6

15.0

0.5

10.0

a. What solvent would you choose? Support your answer by


means of a schematic diagram.
The appropriate solvent to be used is acetone since it satisfies
the requirement for an ideal solvent: dissolve the solute of interest at
high temperature and sparingly only at lower temperature. The desired
solute should also recrystallize specifically from the solvent when
cooled. Acetone would effectively dissolve both solutes but it will
selectively recrystallize solute A upon cooling.
100 ml of hot acetone solution can dissolve 20 g A and 8 g B
20 g A
100 ml acetone x
=20 g A
100 ml acetone

100 ml acetone x

8.0 g B
=8.0 g B
100 ml acetone

100 ml of cold acetone solution can dissolve 5 g A and 0.1g of B


5g A
100 ml acetone x
=5 g A
100 ml acetone
0.1 g B
=0.1 g B
100 ml acetone
Mixture of 2 g A
and 8 g B
dissolves in hot

100 ml acetone x

Cool
solution.
2 g of A and 0.1
g of B remains
in the mother
liquor

7.9 g of B
crystallizes
out

7.9 g B recovered
x 100 =98.75 yield
8.0 g B present initially
2.0 g A
x 100 =95.24 purity of A
2.1 g of crystals
b. Theoretically, what is the purity of A and B after one
crystallization?
The recrystallized B is 100% pure though its yield is only 98.75%
(based from 8 g on the sample initially). On the other hand, compound A is
only 95.24 % pure.
4. A mixture of three compounds, A, B and C, is to be separated and
purified by crystallization. Their solubilities in g/100 mL ethanol are
given below.
Solvent
A
B
C
Cold

1.05

5.6

4.2

Hot

20.5

2.3

3.5

MIXTURE:
4.0 g A + 4.0
g B + 4.0 g

Heat
solutio
n
MOTHER
LIQUOR: 4.0
g A + 2.3 g
B + 3.5 g C

UNDISSOLVED
CRYSTALS: 1.7
g B and 0.5 g
Cool
solutio
n

MOTHER LIQUOR:
1.05 g A + 2.3 g
B +3.5 C
RECRYSTALLIZED:
2.95 g A

a. If a mixture containing 4.0 g each of A, B and C are


recrystallized from 100 mL ethanol, which compound would be
obtained pure?
Given the flow diagram above, compound A will be obtained pure
from recrystallization since the other compounds will remain in the
mother liquor upon cooling given their solubilities.
b. If the filtrate from (a) is evaporated to 50 mL, which of the
compound(s) will separate upon cooling? What is its purity?
MOTHER
LIQUOR: 4.0
g A + 2.3 g
B + 3.5 g C

EVAPORATOR

MOTHER LIQUOR
4.0 g A + 1.15 g
B + 1.75 g C

Cool

MOTHER LIQUOR
0.525 g A + 1.15
g B + 1.75 g C

50 mL
ethanol

UNDISSOLVED
SOLIDS:
1.15 g B + 1.75

RECRYSTALLIZED:
3.475 g A

Compound A will separate upon cooling and this recrystallized


solid will be 100 % pure. Compared from (a), evaporation of solvent
increases the percent yield of the recrystallization process.
5. You need to perform a recrystallization using a mixed-solvent
system. Which of the following solvents could not be used as
solvent pairs for the experiment? Explain your selection?
A. Hexane and water- These are two immiscible solvents such that it
cannot be used for mixed solvent recrystallization since miscibility of the
solvent pairs is one of the needed properties in this type of recrystallization.
6. What are the advantages/disadvantages of mixed solvent
recrystallization over single solvent recrystallization?
The choice of solvent is the most critical part in recrystallization to
purify a substance. However, few solvents can be considered ideal for a
specific solute. As such, to produce the ideal properties of a solvent which
cannot always be obtain in single-solvent crystallization; mixed-solvent
recrystallization is used. Its advantage is that it allows the solute to be
dissolve at higher temperature to the first solvent and sparingly only to the
second solvent, an ideal property of solvent for recrystallization. This allows
mixed-solvent crystallization to have a higher yield of desired solute
compared to single-solvent. On the other hand, the disadvantage of mixed
solvent is that extra care and attention must be given when the technique is
executed. This includes taking into consideration the boiling points of the
solvent pairs. If the first solvent to be added has a higher boiling point
compared to the second solvent, the solution must be cooled first below the
boiling point of the second solvent before adding it to the solution; otherwise
addition of this solvent could cause vigorous boiling and spewing of hot
solvent. Compared to single-solvent recrystallization which uses lesser
amount of solvent, excessive amounts of second solvent must be added if
unduly amount of the first solvent is initially used to dissolve the solute in
mixed-solvent.
References:
[1]University of Sydney Faculty of Science. Skills. [Online] 2014.
https://scilearn.sydney.edu.au/fychemistry/LabManual/Skills.pdf
(accessed February 9, 2015).
[2]University of Calgary Department of Chemistry.Organic Laboratory
Techniques.
[Online].
2014.
http://www.chem.ucalgary.ca/courses/351/laboratory/filtration.pdf

(accessed February 9, 2015).


[3]Pavia, D., Kriz, G., Lampman, G., Engel, R. A Microscale Approach to
Organic Laboratory Techniques. Chapter 11: Crystallization: Purification
of Solids. Brooks/Cole: California, 2013. pg 684.
[4]Gilbert, J. and Martin, S. Experimental Organic Chemistry 5th ed. Chapter
2: Techniques and Apparatus. Brooks/Cole: California, 2013. pg 66.
[5]University
of
Wisconsin-Madison
Department
of
Chemistry.
Recrsytallization.
[Online].
2014.
http://chem.wisc.edu/deptfiles/genchem/Chm346/pdf/recrystallization.p
df (accessed February 9, 2015)
[6]University of Toronto Department of Chemistry.Recrystallization.
[Online].2014
http://www.chem.utoronto.ca/coursenotes/CHM249/Recrystallization.pd
f (accessed February 9, 2015).
[7]Erowid Organization. Solvent Miscibility Table. [Online]. 2014.
http:erowid.org/archive/rhodium/pdf/solvent.miscibility.pdf
(accessed
February 12, 2014)