CM133L Organic Chemistry Laboratory

1st Quarter SY 2022 - 2023

Liquid-liquid Extraction of Adipic Acid Using Ether

Aspuria, Aicee Julliane I.1, Badillo, Allyssa Sophia, R.1, Caalim, Alexandria Nicole A. 1

1CM133L/A21, School of Chemical, Biological and Material Engineering and Science, Mapua University

ABSTRACT

Separating an organic component from a mixture of chemicals is important. A chemical process called extraction entails
dissolving the combination in the first solvent and adding a second immiscible solvent to dissolve one of the mixture's
components only. The two layers are then aggressively mixed to enable the transfer of a dissolved component from one layer
to the other. The extraction of one chemical from the mixture is then finished by separating the two layers. The experiment
conducted was successful in achieving its goals of showing the effects of salting out, extracting organic chemicals, and
figuring out how the number of extractions affected the distribution coefficient and percent yield. A proportion of component(s)
from the aqueous layer was removed from the organic layer after organic compounds were segregated based on their
solubilities. A direct correlation exists between the number of extractions and the distribution coefficient. These results are
comparable to the calculated percent yield. However, the resulting distribution coefficients are negative (-0.2224 and -0.2418)
and the percent yield exceeded 100% (128.6% and 131.9%). The calculations were double-checked and were identified to be
correct. Hence, errors can only come from procedural mistakes. This can be proven by the larger value of extracted acid
compared to the original sample. To avoid such errors, this paper also included a list of recommendation for future
researchers at the latter part.

Keywords: Extraction, Ether, Salting-out Effect, Distribution Coefficients, Direct Correlation, Immiscible

INTRODUCTION

Separating an organic component from a mixture of is soluble in both of them, which results in a partition. A very
chemicals is relatively important. These compounds are common question then arises which asks whether the
frequently created by synthetic processes or from natural organic layer sits on top or at the bottom. The relative
sources (Karger, 2022). A chemical process called densities of the organic and aqueous solvents determine
extraction involves dissolving one or more chemicals from a this. In most cases like this particular experiment, ether
mixture into the right solvent (Harris, 2015). In this solvents float on top of the mixture because they are
experiment, adipic acid and ether are separated and typically less dense than water. On the other hand,
purified from a combination of the two using the halogenated solvents are relatively heavier and usually sink
conventional method of liquid-liquid extraction. to the bottom (Nichols, 2022).

Utilizing a substance's differential solubility in several During extraction, the stopcock of the separatory funnel is
solvents, the process of liquid-liquid extraction is used to opened, enabling one layer to flow out, and the two phases
remove impurities. In contrast to crystallization, the sample are separated after they have settled back into two layers.
in this process can be either solid or liquid. This entails The liquid that released the solute is known as the extract,
dissolving the combination in the first solvent and adding a and the liquid that recovered it is known as the raffinate.
second immiscible solvent to dissolve one of the mixture's Following extraction, the sample's distribution (or partition)
components only (Sandtorv, 2021). The two layers are then coefficient KD determines the final ratio of the sample's
aggressively mixed to enable the transfer of a dissolved concentrations in the two solvents (Harvey, 2020). It is easy
component from one layer to the other since the solvents to express the concentration in mg of solute/mL of the
utilized are immiscible. The two layers are once again solution when speaking at the microscale. The
allowed to develop when the transfer is finished. The concentration of the sample in the extracting solvent 2 is
extraction of one chemical from the mixture is then finished provided by C2, while the final, or equilibrium, concentration
by separating the two layers. Though the experimented of the sample in the original solvent 1 is given by C1. The
solvents are immiscible, it should be noted that the sample

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ratio between the two concentrations is the definition of the acid was transferred in the quick fit separatory funnel and
distribution coefficient, as seen below. was extracted using 10 mL of ether. The setup of the
extraction process is shown in Figure 1 below. It is to be
noted that before extraction, the two solutions were mixed
vigorously which leads to a pressure build-up inside the
vial. Because of this, the system was vented by carefully
Equation 1
removing the cap once in a while during the shaking
process. After extraction, a drop of phenolphthalein was
Needless to say, the distribution coefficient and extraction added to the aqueous layer and was once again titrated
efficiency increase with the sample concentration in the with the prepared 0.05 M NaOH. The remaining content of
extracting solvent. the separatory funnel was placed in a beaker labeled “Ether
Extract”. The same exact procedure was performed once
With all of those concepts kept in mind, the researchers again, but two extractions were made using 5 mL of ether
aimed to: each. All measurements, calculations, and observations
were recorded in the laboratory notebook.
 Visualize the salting out effect
 Separate organic compounds using extraction
 Know the effect of the number of extraction on the
distribution coefficient
 Know the effect of the number of extraction on the
percentage yield

MATERIALS AND METHODS

This experiment is divided into two parts: (1) Salting-out

Effect and (2) Determination of a Distribution Coefficient
and Percentage Yield of Extraction. The materials required
to successfully accomplish the experiment include the
following: Erlenmeyer flask, pipet, quick fit funnel, micro test
tubes, and the reagents being observed.

For the first part of the experiment, the researchers were

tasked to observe the so-called salting-out effect. This was
accomplished by filling two micro test tubes with 3 mL
distilled water and adding a drop of 0.003M aqueous crystal Figure 1. Extraction Set-up
violet as well as 0.50 mL of n-amyl alcohol to each one of
them. The samples on both test tubes were carefully
shaken by hand for a couple of minutes. After which, RESULTS AND DISCUSSIONS
sodium chloride was added to one test tube until the water
layer is saturated. The results were observed and recorded Salting Out Effect
based on the amount of color in both liquid layers.
In general, the process known as "salting out" is when the
Moving on to the second part of the activity where the solubility of a nonelectrolyte substance in water declines as
researchers did actual extraction. A 250 mL stock solution the concentration of salt increases (Heinonen & Sainio,
of 0.05 M NaOH was prepared by the laboratory assistant, 2013). With the use of sodium chloride, the water-miscible
together with a 10% adipic acid solution. 10 mL of the acid solvent in which the sample is dissolved separates from the
was placed into an Erlenmeyer flask using a pipette, added
aqueous solution. Because Na+ and Cl- ions are present in
with a drop of phenolphthalein, and titrated with the NaOH
NaCl, it becomes a powerful electrolyte that can ionize
solution up to a light pink endpoint. Another 10 mL of adipic
entirely in a solution due to its high ionic strength

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(LibreTexts, 2020). The aqueous layer's density and the

droplets' surface tension are both increased by the addition
of salt, causing separation. As seen in Figure 2, the mixture
(left) with added sodium chloride salt has a more vibrant
color in its upper layer. This is because salt forces the
separation of crystal violet from water.

Figure 3. Solution mixture to undergo extraction process

Determination of Distribution coefficient and Percent

Yield
Figure 2. Salting-out effect in the mixture of aqueous
crystal violet and alcohol Table 1.1. Volume NaOH Solution for titration (mL)

Original 1% sample 26.30

Extraction Solvent
Solution extracted once 35.20
Before going to the actual report of the data gathered in this
Solution extracted twice 36.10
part of the experiment, it is important to note that
determining which solvent pair to use for a liquid-liquid
extraction is a vital step. When deciding which solvents to Table 1.2. Weight of Adipic acid (grams)
utilize, the following factors must be taken into account: (1)
the solute must be more soluble in the solvent than in Original 1% sample 0.0961
water. Because of this, it is vital to be aware of the solute's Solution extracted once 0.1286
partition coefficient in a prospective solvent pair; (2) the
solvent pair must be immiscible in water and must not Solution extracted twice 0.13199
produce a homogenous solution; and (3) the solvents must
be inert - incapable of reacting with the solute (LibreTexts,
2020). Additionally, to make it simple to separate the Table 1.3. Distribution Coefficient
solvent from the solute, the solvent must also be volatile. It Solution extracted once -0.2224
is important to note that the organic solvent that is
immiscible in water often has a low or non-polar polarity. In Solution extracted twice -0.2418
this laboratory, the students extracted adipic acid using
ether. Figure 3 shows the immiscibility of the two
aforementioned solvent mixtures.

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1st Quarter SY 2022 - 2023

Table 1.4. Percentage Yield (%)

Solution extracted once 128.6

Solution extracted twice 131.9

To calculate the distribution coefficients KD of the solutions,

titration was performed up to a light pink endpoint (Figure
4). This determines the concentration of adipic acid in the
ether and aqueous layer. The chemical equation satisfying
the titration reaction is shown below:

Equation 2 In actuality, the original sample will always contain more

amount of solute than those extracted from a solution only.
In line with this, the distribution coefficient must always be
positive and the percent yield must not be greater than 100.
This could only mean that the experimental data is
inaccurate due to numerous experimental errors. The
consecutive use of a pipette to get the adipic acid solution
and liquid ether without in-between cleaning accounts for a
greater extracted acid weight. Some acid must have been
transferred to the ether solution, giving a larger actual
volume of acid pipetted than recorded. The error could also
be because of an improper extraction process. The two
solvents must not have separated completely, letting a
small amount of the organic solvent be extracted with the
aqueous one.

On a brighter note, the computed weight of the adipic acid

in the original sample is similar to the expected value. The
prepared original 1% sample from the 10% adipic acid
solution containing 1 gram of solute gives a theoretical
Figure 4. Titration of the aqueous solution up to a light pink value of 0.10g. This is almost equal to our experimental
endpoint value of 0.0961g, reporting a 3.9% percent error.
Additionally, the calculated data shows a direct relationship
It can be seen from table 1.1 that the amount of NaOH
between the number of extractions to the extracted amount
solution used in the titration of the original sample is larger
of acid sample. It is possible to conclude that more acid
than those extracted. This then leads to: (1) greater values
was recovered by extracting twice than by extracting just
of acidic acid weights in extracted solutions than the original
once by comparing the percentage yield and distribution
sample, (2) negative distribution coefficient, and (3) percent
coefficient values that were obtained for each of the
yield larger than 100. Sample of the calculations done are
extractions. The percentage yield and the partition or
presented below:
distribution coefficient both rise as the number of

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extractions rises. This is consistent with several kinds of percentage yield have a direct proportion with the number
research showing that using modest quantities of organic of extractions.
solvents for a number of extractions is mathematically
shown to be more effective than using a big amount of To ensure precise and superior outcomes for the extracted
chemical, a number of measures must be performed during
organic solvent for a single extraction. Only a little portion of
extraction. Due to the ether being a very flammable
the analyte from the solution is recovered after a single substance, it is advised that future researchers make sure
extraction. The amount of analyte recovered from each there are no flames present in the lab when conducting the
extraction is the same, and the extracted fractions are experiment. To prevent unneeded compound leakage,
accumulated to provide a high extraction efficiency (Erkey, make sure the separatory funnel is closed when you fill it
2000). with compounds. Additionally, it is crucial to confirm that the
ether extract and the n-amyl alcohol solution were properly
disposed of in their corresponding trash bottles. Throughout
CONCLUSIONS AND RECOMMENDATIONS the actual extraction process, the mixture must be
constantly evacuated after shaking to prevent pressure
The experiment was successful in achieving its goals of buildup in the separatory funnel, which might result in
showing the effects of salting out, extracting organic accidents and funnel damage. Prior to extraction, the
chemicals, and figuring out how the number of extractions mixture must stand for a few minutes to stabilize and aid in
affected the distribution coefficient and percent yield. When the aqueous layer's settling, allowing for the extraction of
NaCl, an electrolyte, was added to the solution, the salting more desired components into the organic layer.
out effect was seen, which is the production of precipitation
owing to the lower solubility from the electrolyte influencing
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