CHM142L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

Extraction
Terrado, Rence Christian L.

Professor Marilyn Miranda, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; Bote,Jairus Lemuel ; Brillas, Catherine Jill
1

CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology

ABSTRACT
One of the best separating techniques from a liquid-liquid mixtures or are in the same state or
phase is extraction. Extraction is a separation technique frequently employed in the laboratory to
isolate one or more components from a mixture. Extraction is based on the principle of the
equilibrium distribution of a substance (solute) between two immiscible phases, one of which is
usually a solvent. The aim of this experiment is to (1) visualize salting o.ut effect, (2) to separate
organic compounds using extraction, (3) to know the effect of number of extraction in distribution
coefficient, and (4) to know the effect of number of extraction in percentage yield. In this
technique, the group used salting out effect which uses Sodium chloride to neutralize the charge
on a molecule, and when you neutralize the charge of a molecule, the molecule has reached its
solubility point. It will not be soluble in the aqueous solvent, hence there won't be any interactions
with the aqueous solvent. Determining the distribution coefficient and the percentage yield
depends on the number of extraction. The greater the number of extraction, the greater the
percentage yield will be. The group obtained 15.55% for single extraction and 36.36% for double
extraction which proves the study that percentage yield varies directly to the number of
extractions conducted.
Keywords: Extraction, Salting out effect, Distribution Coefficient

INTRODUCTION in everyday life. Extraction is a convenient

Like recrystallization and distillation,
extraction is a separation technique
frequently employed in the laboratory to
isolate one or more components from a
mixture. Unlike recrystallization and distillation,
it does not yield a pure product; thus, the
former techniques may be required to purify a
product isolated by extraction. In the technical
sense extraction is based on the principle of
the equilibrium distribution of a substance
(solute) between two immiscible phases, one
of which is usually a solvent. The solvent need
not be a pure liquid but may be a mixture of
several solvents or a solution of some chemical
reagent that will react with one or more
components of the mixture being extracted to
form a new substance soluble in the solution.
The material being extracted may be a liquid, a
solid, or a mixture of these. Extraction is a very
general, highly versatile technique that is of
great value not only in the laboratory but also
method for separating an organic substance
from a mixture, such as an aqueous reaction
mixture or a steam distillate. The extraction
solvent is usually a volatile organic liquid that
can be removed by evaporation after the
desired component has been extracted. The
extraction technique is based on the fact that if
a substance is insoluble to some extent in two
immiscible liquids, it can be transferred from
one liquid to the other by shaking it together
with the two liquids. For example, acetanilide is
partly soluble in both water and ethyl ether. If a
solution of acetanilide in water is shaken with a
portion of ethyl ether (which is immiscible with
water), some of the acetanilide will be
transferred to the ether layer. The ether layer,
being less dense than water, separates out
above the water layer and can be removed and
replaced with another portion of ether. When
this in turn is shaken with the aqueous
solution, more acetanilide passes into the new
ether layer. This new layer can be removed and

Experiment 05 Group No. 4 Date 11/28/14 1 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015

combined with the first. By repeating this

process enough times, virtually all of the
acetanilide can be transferred from the water
to the ether. As we stated above, the
substance being extracted may be a solid.
Extractions of this type will not be conducted
here, but they are probably already a part of
your own experience. The brewing of tea from
tea leaves (or the tea bag that combines
extraction and filtration) and of coffee from the
ground bean are excellent examples of the
extraction of a solid mixture with a hot solvent
(water). In solvent extraction, a distribution
ratio is often quoted as a measure of how well-
extracted a species is. The distribution ratio
(KD) is equal to the concentration of a solute in
the organic phase divided by its concentration
in the aqueous phase. Depending on the
system, the distribution ratio can be a function
of temperature, the concentration of chemical
species in the system, and a large number of
other parameters. Because its a function of
temperature KD values are always
accompanied by temperature readings.
The objectives of the experiment are: (1) to
visualize salting out effect, (2) to separate
organic compounds using extraction, (3) to
know the effect of number of extraction in
distribution coefficient, and (4) to know the
effect of number of extraction in percentage
yield.
In part two of experiment 5 entitled
Distribution of a Distribution Coefficient and
Percentage Yield of Extraction is done by
following these procedures indicated in the
laboratory manual. First, the group prepared
250 mL of stock solution of 0.05 M NaOH and
2.50 M NaOH then 10 mL of 10% adipic acid
was transferred to a 50 mL Erlenmeyer flask
using a pipette then add drops of
phenolphthalein and titrated it with 0.05 M
NaOH until the solution turned light pink in
color then volume of titrant used was recorded.
10 mL of adipic acid was then transferred to
the quick fit separatory funnel and extracted
using 10 mL ether. Then added drops of
phenolphthalein to the aqueous layer and
titrated with 0.05 M NaOH then volume of
titrant used was recorded. Content in the
separatory funnel was placed in a bottle called
Ether Extract then another 10 mL of adipic acid
was placed in the separatory funnel then
extracted again with 5 mL ether and the
aqueous layer was drawn off into a clean
bottle. Drained the separatory funnel then
placed in the Ether Extract bottle. And the
group transferred the previously drawn into the
separatory funnel the extracted using 5 mL of
ether then added drops of phenolphthalein to
the aqueous layer and titrated with 0.05 M
NaOH then volume of titrant used was
recorded. Then lastly the group computed the
distribution coefficient and percentage yield in
single and double extraction.

MATERIALS AND METHODS

The part one of the experiment entitled

Salting-Out Effect is done by following these
procedures. First is to fill two (2) micro test
tubes with 3 mL of distilled water then to each
test tube added a drop of 0.003 M aqueous
crystal violet and 0.50 mL of n-amyl alcohol.
The after the test tubes has been shaken, one
micro test tube was filled with sodium chloride
until water layer has been saturated. Then the
group compared the results in the two test
tubes in terms of amount of colour in the water
layer then observations were recorded.

Experiment 05 Group No. 4 Date 11/28/14 2 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015

the group the observed that the mixture of

aqueous crystal violet and n-amyl alcohol
without the sodium chloride (NaCl) has a larger
violet part on the mixture than the clear part
but when the other micro test tube with a
mixture of crystal violet and n-amyl alcohol
added with sodium chloride had a larger clear
color part in the mixture than the violet colored
part of the mixture due to salting out effect.

Salting out is the process in which you add

salts to charged molecules of interest. Each
molecule has an isoelectric point, which is
Figure 1. Liquid-liquid Extraction Set-Up defined as the pH at which the particle would
have a net charge of 0 because salts are
formed by the combination of ions, they help to
neutralize charged molecules when they
(Table 1. List of apparatuses used) dissociate (they dissociate, generally upon
contact with the charge molecule). This
separates the molecule from its aqueous (or
Erlenmeyer Micro test tubes polar) environment, the same way fats and oils
flask
will separate from aqueous environments like
water (this phenomenon is called the
Pipette Quick Fit Separatory
Funnel hydrophobic effect). When you neutralize the
charge on a molecule, the molecule has
reached its solubility point. It will not be
soluble in the aqueous solvent, hence there
(Table 2. List of reagents used) won't be any interactions with the aqueous
solvent.

Adipic Acid Crystal Violet

Distilled Water Ether In part two of the experiment entitled

Determination of Distribution coefficient and
Phenolphthalei Sodium
Percentage yield shows on what single and
n Hydroxide
double extractions affect the Distribution
Sodium n-Amyl Alcohol constant and Percentage yield. The table
Chloride shown below shows the computation
conducted by the group.

RESULTS and DISCUSSIONS

The experiment entitled Extraction is used to Table 3. Determination of Distribution coefficient and Percentage
isolate one compound to the other which is in yield

both liquid phase. And part one of the

experiment entitled Salting out Effect had
reactions when the experiment is conducted, Volume NaOH solution for Titration, mL

Experiment 05 Group No. 4 Date 11/28/14 3 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015

experiment. And also the student must wear

Original 1% sample 38.1 protective masks and gloves to avoid inhaling
the volatile reagents which are mostly
Solution extracted 32.1 carcinogenic like the ether. Avoid forgetting to
once
add phenolphthalein to the mixture before
titration so it will be easy for the student to
Solution Extracted 24.2
twice neutralize the mixture by changing the
mixtures color. Shake the mixture gently with
Weight of adipic acid, g frequent venting to avoid pressure build up.
This is necessary because if venting is not
Original solution 0.1389 properly made the separatory funnel may burst
the stopper, the mixture may slop, the cap
Solution extracted 0.1173 may blow away extremely and break and
once cause accidents. When the stopcock is in
parallel position, it means open. When it is in
Solution Extracted 0.0884
perpendicular position, it means closed. This is
twice
important to know because if the student does
Distribution coefficient not pay attention to the position of the
stopcock the mixture may spill. Ether is toxic
Single Extraction 0.1841 and very carcinogenic and it needs to be
handled carefully and securing that the
Double Extraction 1.142 stopcock is in perpendicular position is
necessary. During separation of liquid, be
Percentage yield,% careful to separate the desired liquid to the
other. Make sure to stabilize the mixture for a
Single Extraction 15.55 few minutes to be able for the aqueous and the
organic phase to separate completely. After
Double Extraction 36.36
this be careful to separate the two after
opening the separatory funnel watch carefully
Multiple extractions with smaller amounts of when and close the funnel after all the desired
solvent are more efficient than a single portion comes out.
extraction with the same total amount of
solvent. This concept explains why in this CONCLUSIONS AND RECOMMENDATIONS
experiment the group got 36.36% percent yield
in the double extraction while only 15.55% in In this lab experiment we took advantage of
the single extraction. The computations in the properties of the materials to move them
Appendix will show and explain further why into and out of various phases by using the
acid base properties of the compounds. Adipic
double extraction method is more preferable
acid is soluble in ether until it is deprotonated
than single extraction method. and becomes highly water soluble, but neither
the acid nor the base changes the solubility of
In performing the extraction experiment there it. This is not surprising since it doesnt contain
are some precautions to be known by the the kinds of functional groups that would be
affected by adding or removing protons. The
student who will conduct this experiment. First
group proved the theory of salting-out effect.
is they must know that the reagents to be used After the addition of NaCl to the solution it
are volatile and flammable so flames in the started to react, the crystal violet leaves the
laboratory is prohibited while doing this H2O exposing the greater part. And also in

Experiment 05 Group No. 4 Date 11/28/14 4 of 5

 CHM142L Organic Chemistry 1 Laboratory
2nd Quarter SY 2014-2015

determining the distribution coefficient and

percentage yield which the double extraction
method has a greater percentage yield Single extraction
therefore the greater the number of extraction,
the greater the percentage yield will be. % yield = (0.1389-0.1173)/(0.1389) * 100% =
15.55%

Double Extraction
REFERENCES
% yield = (0.1389-0.0844)/(0.1389) * 100% =
1. Baldwin RL. How Hofmeister Ion 36.36%
Interactions Affect Protein Stability.
Biophys J. 1996;71:20562063.

2. Chang, R. (2008). General Chemistry: The

Essential Concepts (5th Ed.). NewYork:
McGraw-Hill.

3. L. Gattermann, Die Praxis des organischen

Chemikers, 40th ed., de Gruyter & Co., Berlin,
1961, pp 260-261.

APPENDIX

Computations:

KD = {[Solute]organic layer }/{[Solute]aqueous layer}

[Solute]organic layer = mmolAdipic acid/ mLsolution

0.1389 x (mmol/146.14 mg) (0.1173/5.36 x

100)

= 0.9505 0.8027

= 0.1478/10 mL = 0.01478

Single Extraction

KD = 0.01478/0.803 = 0.1841

Double Extraction

KD = 0.03456/0.06049 = 1.142

Percentage yield, %

% yield = (mass of Adipic acid in ether layer/

mass of Adipic acid in original sample) x 100%

Experiment 05 Group No. 4 Date 11/28/14 5 of 5