Introduction

Extraction is a technique commonly used in

organic chemistry to disperse a substance or material
desired from those that are not. While the term
extraction may be unfamiliar, its process is in fact
something that is commonly performed. In the
procedures found in this experiment, researchers will
have an opportunity to develop their present
experimental expertise further by isolating organic
compounds using the liquid-liquid type of extraction.
(Gilbert, 2015)
The desired compound from a reaction is
frequently part of a mixture, and its isolation in pure
form can be a significant experimental challenge.
Similar to the previous performed experiment,
recrystallization and distillation, extraction is one of
the more methods for separating and purifying
organic solids and liquids. As what will be seen in
this experiment, extraction method involves
partitioning of compounds between two immiscible
phases. This process is titled phase distribution and
can result in separation of compounds if they have
been distributed differently between the two phases.
(Martin, 2011)
According to research, distribution of
solutes between phases is a result of adsorption or
partitioning phenomena. Partition involves the
difference in the solubility of a substance in two
immiscible solventin other words, selective
dissolution. On the other hand, adsorption is based on
the selective attraction of a substance in a liquid or
gaseous mixture to the surface of a solid phase.
Extraction involves selectively removing
one or more components of a liquid, solid, or gaseous
mixture into a separate phase. The substance being
extracted will partition between two immiscible
phases that are in contact, and to which it form a
distinct layer and the ratio of its distribution between
this phases will depend on the relative solubility of
the solute in each phase.
There are several of types in extraction, and
this experiment deals with the liquid-liquid
extraction. Liquid-liquid extraction is by far one of
the most common methods in separation of an
organic compound from a mixture. This process is
used by chemist not only for the isolation of natural
products but for purification of products from
chemical reactions as well.

The process involves the distribution of solutes, A,

between two immiscible liquids, Sx, the extracting
phase, and So, the original phase. The immiscible
liquids generally encountered in the organic
laboratory are water and some organic solvent, such
as diethyl ether, (C2H5)2O or dichloromethane,
CH2Cl2. At a given temperature, the amount of the
distribution of solutes in g/ml, in each phase is
expressed quantitatively in terms of a constant, K,
commonly called the partition coefficient, from
equation 5.1 (Martine, 2015). The volumes of
solution, if the solution is dilute, only slight errors
result if volumes of solvent are used. Moreover, a
close approximation of the partition coefficient K can
be obtained by simply dividing the solubility of A in
the extracting solvent Sx by the solubility of A in the
original solvent So.

K=

[ A ] Sx
[ A ] So

The process of liquid-liquid extraction can

be well-thought-out a competition between two
immiscible liquids for solute A, with solute A
distributing or subdividing between these liquids
when it is in contact with both of them. The equation
above indicates that at equilibrium, the ratio of the
concentrations of A in the two phases will always be
at constant. The equation as well leads to various
important predictions. Taking for example when K>
1, the solute will be mainly in the extracting solvent,
Sx, as the volume, Vx of this solvent is at least equal
to the volume, Vo, of the original solvent, S o. thus the
amount of the remaining solute in S o will depend on
the value of K.
There are many other equations involve in
extraction and it is within these calculations that the
multiple extractions become increasingly important
as the volume of K decreases. The improved recovery
of solute from this multiple extractions, must acquire
balance likewise with the practical consideration that
the relatively small increases in recovery may not
substantiate the additional time and solvent required
to perform multiple extractions unless the product is
of great value.

Experimental Section
Assemble the apparatus as shown in Fig.
5.1. Note the proper way of handling each equipment
to prevent unnecessary breakage which can be as
well a source of error in the following data gathering.

Salting-out Effect In the first part of the

experiment which involves the salting-out effect, two
micro test-tubes were filled with 3 ml of distilled
water. A drop of 0.003M aqueous crystal violet was
added with a subsequent 0.50 ml of n-amyl alcohol.
Both test tubes was given a shake until such a violet
vibrant color change was apparent. Upon completion,
a sodium chloride was introduced to one of the test
tube where in a layer formed separately and that the
water layer is saturated. A comparison between the
two test tubes was compared and recorded.
Distribution coefficient determination
In the second part, in a 150 ml Erlenmeyer flask,
a 10 ml of 10% adipic acid was added with a
drop of phenolphthalein as an indicator. The
solution was then titrated using NaOH thats
standardized with a 250 ml of stock solution of
0.05M NaOH from 2.50M NaOH until an
appearance of light pink colored was observed.
This is an indication of the endpoint being
reached. Take note of the volume NaOH used.
This volume of titration was later used to obtain
the weight of the acid in the original solution. 10
ml of the adipic acid was then transferred to the
quick fit separatory funnel for the extraction.
Before proceeding with the extraction, be sure

that no flame was present in the area. A 10 ml of

ether was mixed in the adipic acid as an
extractor. A drop of phenolphthalein was added
as well to the extracted aqueous layer and was
titrated with 0.05M 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
with the addition of 5 ml of ether. The aqueous
solution was extracted while the organic solution
was drawn off and transferred to the labeled
bottle Ether extract. The aqueous layer
previously extracted was placed again in the
separatory funnel, mixed with another 5 ml of
ether. This was subjected once more to
extraction. A drop of phenolphthalein was added
to the aqueous layer and titrated with 0.05 M
NaOH. The resulted volume were collected and
was recorded for further observation.