EXPERIMENT NO.

3:
Extraction: Determination of its Efficiency &
Calculation of the Distribution Coefficient

Mesina, Anna Beatrice B.

Cainoy, Francesca Marie Nicole P. [ABSENT but CONTRIBUTED]
De La Salle University, Manila
LBYCH37: N01B
Mr. Eric Punzalan
October 6, 2016
Extraction: Efficiency and Distribution Coefficient 1

INTRODUCTION
Inside the laboratory, it is essential to ensure that the glassware that will be used is free
from materials that are capable of altering heavily the desired outcome of the experiment. In
order to prevent that from occurring, the glassware is rinsed with running tap or distilled water
and detergent. However, doing so only makes it clean enough for general use because few
organic materials still stick to the surface of the glass – that is why Acetone is often present in
the laboratory; it is capable of removing organic residues in glassware, and of quickly drying the
newly washed glassware. In line with this, there are a number of specific laboratory techniques
which aim to eliminate unnecessary substances from the sample. One separation process done in
the laboratory aims to isolate one or more components from a mixture by separating it from those
that are unnecessary – and it is known as extraction. This method comprises five types: liquid-
liquid extraction, solid-phase extraction, solid-phase microextraction, Soxhlet extraction, fizzy
extraction. This experiment is focused on liquid-liquid extraction or solvent extraction. Since
extractions are often performed using aqueous solutions, it is important to note the behaviour of
the solvent for it projects the miscibility of the solvent. Moreover, oxygen containing solvents
are usually more soluble in water (and vice versa) because of their ability to act as hydrogen
bond donor and hydrogen bond acceptor. Other solvents such as alcohols increase the solubility
of water in organic layers significantly because those are miscible with both phases and act as a
mediator which leads to the formation of emulsions.
EXPERIMENTAL PROCEDURE
Since three types of titration and extraction will be used in this experiment, a solution
was first neutralized from a 0.1M standard NaOH. This was done by adding 2m L of Acetic Acid
and 20mL distilled water in a 50mL beaker, transferred into a 250mL volumetric flask, then
diluted up to the mark. This served as the original source of 3 20mL aliquots that was used for
the next procedure – note that with this set-up, a correction factor in the computations part were
used in order to take into consideration that each 20mL came from one source. The aliquots were
labelled 1, 2, 3 into three different 125 mL flasks.
Determination of the Number of Grams of Acetic Acid in a 20-mL Aliquot. Two drops of the
indicator phenolphthalein were added to the first flask which was titrated against a 0.1M
Standard NaOH solution until the solution in the flask turned pink to signify its endpoint. This
serves as the neutralization of Acetic Acid solution with the standard NaOH to determine the
moles or grams in an aliquot.
Determination of the Number of Grams of Acetic Acid extracted by one 20-mL portion of
Toluene. The contents of the second flask was placed in as separatory funnel in which 20mL of
Toluene was added. To release pressure within the reacting contents of the funnel, it was
stoppered and shaken for a few minutes. After this, the stopper was removed and the funnel was
clamped to allow it to sit for a few minutes in order for the contents to separate into upper and
lower. It was observed until the process was done. The lower layer in the funnel was flushed
down into a 125 mL Erlenmeyer flask, while the upper layer was discarded to the organic waste
Extraction: Efficiency and Distribution Coefficient 2

bottler. 2 drops of phenolphthalein was added to Flask 2, titrated with standard NaOH to retrieve
values.
Determination of the Number of Grams of Acetic Acid extracted by two 10-mL portions of
Toluene. The process for Flask 2 was repeated only up to the point before adding
phenolphthalein. After flushing down the lower layer, it was again returned to the separatory
funnel to repeat the process for a second and last time, dividing the addition of toluene into two
10mL portions, still summing up to 20mL. After this, the lower layer of the 2 nd separation was
added with 2 drops phenolphthalein then titrated. The same values were also computed to
compare Flask 2 and Flask 3.

RESULTS AND DISCUSSION

Table 1. Results of Three Different Methods of Extraction
Flask 1 Flask 2 Flask 3
(20-mL aliquot) (One 20-mL (Two 10-mL portions of Toluene)
portion of Toluene)
Initial burette 0.000 0.000 0.00
reading (mL)
Final burette 18.500 16.249 15.813
reading (mL)
Total amount 18.500 16.249 15.813
NaOH
delivered (mL)
Molarity of 0.1 0.1 0.1
NaOH (M)
Moles Acetic 1.850 x 10-3 1.625 x 10-3 1.581 x 10-3
Acid
neutralized [1]
Grams Acetic 0.1111 0.09758 0.09496
Acid
neutralized [2]
Upper layer The upper and The amount of The same as
after shaking lower layers looked the upper layer the 1st
somehow identical, isolated was separation of
were both fewer Flask 3.
transparent liquids, compared to
and had equal the lower
amounts, but the layer.
upper layer was
clearer.
Lower layer The lower layer still The bubbles The same as
after shaking had bubbles even if were the 1st
the liquid was unnoticeable separation of
Extraction: Efficiency and Distribution Coefficient 3

already at rest. compared to Flask 3 but for

Flask 1 and 2. the isolated
The isolated lower layer, the
lower layer 2nd separation
appeared to be had more white
ombré white color than
turning to transparent.
transparent
liquid.
Grams Acetic 1.389 1.389 1.389
Acid originally
present in
20mL before
extraction [3]
Grams Acetic 1.291 1.294
Acid extracted
in Toluene [4]
Percent Acetic 92.94 93.16
Acid extracted
[5]
Distribution 13.23 13.60
coefficient, Kd
[6]
Equations used:
mol 1 mol acid
[1] mol Acetic Acid = L base required ¿ neutralize× base ×
L 1mol base
g AcH
[2] g Acetic Acid neutralized = mol Acetic Acid × 60.05
mol
250 mL VF
[3] g Acetic Acid original = 60.05 g ×
20 mL aliq
[4] g Acetic Acid extracted = g Ac.H original – g Ac.H neutralized
g Ac . H extracted
[5] % Acetic Acid extracted = × 100
g Ac . H original
g Ac . H extracted g Ac . H neutralized
[6] Kd, Distribution coefficient = ÷
20 mL Ac . H extracted 20 mL aliq
Table 1 summarizes the values, observations, and computations that were done in order to
achieve the goal of the experiment: determining the efficiency of liquid-liquid extraction. Note
that the burette readings were recorded with three decimal points because the burette used had
intervals of 0, 0.5, 1, 1.5, …, with 10 graduations in between. Flask 1 was mainly used only for
neutralization of Acetic Acid that will be used against a 0.1M standard NaOH. This explains why
the only values computed were up to grams of Acetic Acid neutralized which shows the result of
Extraction: Efficiency and Distribution Coefficient 4

the neutralization titration. Flask 2 contained another 20mL aliquot of the Acetic Acid but this
time, it will be used for the first type of liquid-liquid extraction; while Flask 3 containing the last
20mL aliquot will be used for the second type. Table 1 gives readers an organized view of values
gathered in order to clearly see whether the two flasks differ or whether they produce the same
results and on which part will it and will it not. The equations used were also enumerated below
the table to understand numerical relationships and how the final conclusion, the distribution
coefficient, was reached. For the second method or flask 3, it can be quantitatively seen that
there is an inverse relationship between the amount NaOH required, amount Acetic Acid
neutralized, and the grams and percent Acetic Acid extracted. This means that the second method
has produced a more precise extraction compared to the first method or flask 3, resulting to a
higher percent extracted and distribution coefficient. Qualitatively, it was also noted that for
Flask 3 separation, there were less upper layer, or the organic layer containing toluene, than the
lower; this can be another explanation that there was indeed more acetic acid extracted. As
compared to the Flask 2 separation, the lower and upper layer appeared to be of equal amount
showing an equal but unsure division.
CONCLUSION
As produced by the data of the experimenter, it can be concluded that extracting two
times into portions yield more efficient and accurate values, and allow scientists to write notes
then make predictions based on their observations for the two divided steps. With Flask 2 having
a 13.23 distribution coefficient and Flask 3 with 13.60, it can be noted that the values of method
1 and method 2 are not that far apart to make one distinguishable from another. Errors in this
experiment can be caused by human error, specifically in making sure that the separatory funnel
is not stoppered when it is settling which the experimenter personally experienced, or
computation error. In this experiment, students must be knowledgeable about the liquids that
they are extracting since the upper layer must be discarded in the organic waste bottle which
means that what is left is the aqueous layer. Fortunately, over-titration was not committed by the
experimenter.

ACKNOWLEDGMENT
The experiments were performed at the laboratories of De La Salle University, Manila,
with the help of the laboratory technicians and chemistry professors. The equipment for
extraction that were used are owned by the university.

REFERENCES
“Extraction” (2013, December 30). Extraction in theory. Retrieved from
http://www.chem.ucla.edu/
Pahlavan B. Dr. (2015). CHEM 2423 extraction of benzoic acid. Retrieved from
http://swc2.hccs.edu/pahlavan/2423L6.pdf
Extraction: Efficiency and Distribution Coefficient 5