CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

Extraction
Miranda, Marilyn 1, de Guzman, Anne K. 2
1Professor,

School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; 2Student, Chm142L/B21, School of Chemical Engineering,
Chemistry and Biotechnology, Mapua Institute of Technology

ABSTRACT
Extraction is the physical process by which a compound or a mixture of compounds is transferred from one phase
into another. In this experiment, a liquid-liquid extraction was performed. Liquid-liquid extractions usually involve
water and an organic solvent. Most common organic solvents (i.e. diethyl ether, ethyl acetate, toluene, methylene
chloride) are immiscible and are much less polar than water. A general rule of thumb for solubility states that like
dissolves like. Polar compounds are more soluble in polar solvents than in nonpolar solvents, and vice versa. The
selective solubility of different compounds in polar versus nonpolar solvents allows the separation of the
compounds in a mixture by liquid-liquid extraction. This experiment aims to know the effect of number of
extractions to the distribution coefficient and percentage yield. Adipic acid was mixed with ether in a separatory
funnel and extracted. The distribution coefficient and percentage yield was later computed and compared with
adipic acid extracted twice.
The group obtained incorrect values for distribution coefficient and percentage yield due to incorrect computation
which was of course, amended. By the end of this experiment, it was determined that double extraction is more
efficient than single extraction alone as double extraction increases the distribution coefficient and the percentage
yield. Generally, the experiment was satisfactory since the objectives were met accordingly. This experiment aims
to know the effect of number of extractions to the distribution coefficient and percentage yield.
Keywords: extraction, liquid-liquid extraction, solubility, distribution coefficient, percentage yield

INTRODUCTION
Chemists often extract an organic compound derived from
other reaction or syntheses. Extraction is a process in
which one selectively dissolves an organic compound in an
acceptable solvent. Organic acids and bases can be
separated from each other by using a variety of aqueous
solutions. The solutions have varying levels of pH which in
turn effects the solubility of the organic compound. Therein
lies the basis for extraction; the factor of solubility.
Extraction has many real world applications. Numerous
organic compounds are extracted from plants for medicinal
purposes such as morphine from the opium poppy, aspirin
from willow bark, and digitalis (a heart drug) from foxglove
to name a few. Or to keep it simple, when you steep a tea
bag in boiling water, add a bay leaf to a pot of soup, or
wash a load of laundry, you are performing a solid/liquid
extraction, in which a solution containing several

Experiment 06 Group No.2 Date November 28,2014

components is mixed with a second, immiscible liquid, for

the purpose of extracting one component of the solution
into the second solvent.
We have seen that recrystallization is used to purify solids
that are contaminated by relatively small amounts of
impurities. By contrast, the technique of extraction is a more
coarse or preliminary technique, in that it can be used to
separate one compound from another or from large
amounts of impurities.
Most uncharged organic molecules are more soluble in
organic solvents than in water. If the organic solvent itself is
not very soluble in water, then when the solvent or one of
its solutions is mixed with water, two layers will form, and
the solvents are said to be immiscible. The layers are called

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2nd Quarter SY 2014-2015

the organic layer and the aqueous layer. If the two layers
are shaken together, small amounts of the components of
the organic layer will dissolve in (or be extracted into) the
aqueous layer, and small amounts of the aqueous layer
components will dissolve (be extracted into) the organic
layer, establishing equilibrium between the two layers.
Thus, if a neutral compound C is initially dissolved in one
layer (phase), it will be distributed, or partitioned, between
the two layers at equilibrium. This experiment aims to know
the effect of number of extractions to the distribution
coefficient and percentage yield.

RESULTS and DISCUSSIONS

MATERIALS AND METHODS

The reason why the test tube containing salt formed two
layers is the salting-out effect, in which the solubility of a
nonelectrolyte in water is decreased when an electrolyte,
like salt is added.

In the first part of our experiment entitled Salting-out Effect,

two micro test tubes were filled with 3 ml distilled water. A
drop of 0.003 M aqueous crystal violet and 0.50 ml of namyl alcohol were added in each test tube. After shaking
the test tubes, sodium chloride was introduced to one of the
test tubes and the results were observed and compared.
In the second part entitled Determination of a Distribution
Coefficient and Percentage Yield of Extraction, 10 ml of
10% adipic acid was added with a drop of phenolphthalein
and titrated with 0.05 M NaOH up to a light endpoint. The
volume of NaOH used for titration was later used to obtain
the weight of the acid in the original solution. 10 ml of adipic
was transferred in the quick fit separatory funnel and mixed
with 10 ml of ether before extracting the acid. A drop of
phenolphthalein was added to the extracted aqueous layer
and titrated with 0.05 M NaOH. The organic layer was
drawn off and placed in a separate bottle with the label
Ether extract.
The next part involved double extraction. Again, 10 ml of
adipic acid was transferred in the quick fit separatory funnel
and mixed with 5 ml of ether. The aqueous solution was
extracted while the organic solution was drawn off and
transferred to the bottle labelled Ether extract. The
aqueous layer previously extracted was placed again in the
separatory funnel, mixed with another 5 ml of fresh ether
and extracted. . A drop of phenolphthalein was added to the
extracted aqueous layer and titrated with 0.05 M NaOH.
The results were recorded and used for further
observations.

Experiment 06 Group No.2 Date November 28,2014

For the first part of the experiment, our observation is

written below:
The micro test tube with distilled water, aqueous
crystal violet and n-amyl alcohol only didnt form
a layer separating the two components. In the
second test tube with salt, it forms a layer with
water at the bottom and the top as violet colored
substance. In the second test tube, the color is
much lighter than that of the first test tube.

The data obtained from the part 2 of the experiment is

shown in tabular form below:
Table 1 Determination of a Distribution Coefficient and
Percentage Yield of Extraction

Volume of NaOH used for titration

Original 1% sample
Solution, extracted once
Solution extracted twice
Weight of Adipic acid in grams
Original Solution
Solution, extracted once
Solution, extracted twice
Distribution coefficient
Single extraction
Double Extraction
Percentage yield
Single extraction
Double extraction

44 mL
31.4 mL
23.7 mL
0.1608 g
0.1147 g
0.0866 g
0.4019
1.7136
28.67%
46.14%

A quantitative measure of the how an organic compound

will distribute between aqueous and organic phases is
called the distribution or partition coefficient. It is the ratio,
K, of the solubility of solute dissolved in the organic layer to
the solubility of material dissolved in the aqueous layer.

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2nd Quarter SY 2014-2015

Solution, extracted once

Since the distribution coefficient is a ratio, unless K is very

large, not all of a solute will reside in the organic layer in a
single extraction. Usually two, three, or four extractions of
the aqueous layer with an organic solvent are carried out in
sequence in order to remove as much of the desired
product from the aqueous layer as possible. The
effectiveness of multiple small volume extractions versus
one large volume extraction is demonstrated by the groups
calculations below:

Solution, extracted twice

Percent yield

Weight of Adipic Acid in grams

Original Solution
Solution, extracted once

Solution, extracted once

Solution, extracted twice

Distribution Coefficient

Experiment 06 Group No.2 Date November 28,2014

Solution, extracted twice

By comparing the obtained values for

percentage yield and distribution coefficient of
each of the extractions it can be interpreted
that by extracting twice, the amount of the
acid acquired was greater than extracting
only once. Thus, the number of extractions
increases the percentage yield and the
partition or distribution coefficient.

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CONCLUSIONS AND RECOMMENDATIONS

The group achieved the data correctly except for the
distribution coefficient and percentage yield due to error in
computation which was later corrected. At the end of the
experiment, it was determined that double or multiple
extractions is more efficient to perform to obtain higher
percentage yield and distribution coefficient and attain as
much of the desired product from the layer.
Certain precautions which are as follows must be observed
when performing the experiment: A protective mask must
be worn when dealing with toxic compounds such as ether.
When shaking the separatory funnel, the barrel must be
pointed away from the holder and his neighbours. Also, the
stop cock must be opened after vigorously shaking to
release the internal pressure.
REFERENCES
1. Zachary Fijal, Constantinos Loukeris, Zhaleh
Naghibzadeh, John Walsdorf, (n.d.) Liquid-liquid
Extraction (University of Illinois at Chicago)
2. Barnard College, Department of Chemistry (n.d.)
Extraction
3.

Experiment 06 Group No.2 Date November 28,2014

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