FEDERAL INSTITUTE OF ESPÍRITO SANTO - IFES

Bachelor's Degree in Chemistry

Practical Class Report No. 4

SOLVENT EXTRACTION

AMANDA ALMERINDO RANGEL

DEBORAH DA SILVA PIMENTEL
MILENA AMORIM LANGAMI
Quésia Costa Rocha

Discipline: Experimental Organic Chemistry I

Teacher: Ana Brígida Soares

VILA VELHA
2020

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 1. INTRODUCTION
The transfer of a solute from one solvent to another is called extraction, or more
precisely, liquid-liquid extraction. The extraction process consists of the separation of a
component of a mixture, through a solvent. This operation is widely
employed in organic chemistry to separate an organic compound from solutions or
aqueous suspensions where they are found. (ENGEL, 2012)
The extraction is based on the fact that the solute is extracted from one solvent to another.
because it is more soluble in the second solvent than in the first. Water is used as one of the
solvents in liquid-liquid extraction, since most organic compounds are
immiscible in water and because it dissolves ionic or highly polar compounds. According to
Engel (2012), when the solvents are relatively insoluble in water, they form,
therefore, two liquid phases, for example an aqueous phase and an ether phase. The table of
(Figure 1) relates a series of common organic solvents that are not miscible with
water and are used for extractions.
Figure 1. Densities of common extraction solvents.

Source: (Engelet al. 2012).

Any solute present in this system distributes itself between the two phases.
liquid. At equilibrium, the relationship of the solute concentrations in the two phases is
aproximadamente constante (para uma dada temperatura), independentemente da
total concentration. This relationship, referred to as the distribution coefficient, or 'K'
partition coefficient is approximately equal to the ratio of the solubilities of the solute in
two solvents, that is, the relationship of the concentrations of solute X that is in equilibrium
between two phases, 1 and 2, is:
[X2]
X1⇌ X2 K= X1

That said, solvent extraction generally does not remove all the solute from the mixture.
original, leaving a greater or lesser residue according to the partition coefficient. A
the efficiency of extraction is directly related to the amount of solvent used
and, mainly, with the number of times (cycles) in which the extraction is repeated. In the second
extraction, for example, the solute that remained in the liquid phase (aqueous, for example)
as a residue of the first extraction, it redistributes between the two phases, with the same
partition coefficient, then an additional amount of solute is extracted. Another
One aspect that is well understood is that we will extract more solute if we use a larger volume.
of solvent. (CONSTANTINO, 2011).

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 After extraction, the organic solvent is 'wet', that is, it has some
amount of dissolved water, even if the miscibility is not great. The amount of
dissolved water varies from one solvent to another. This water can be removed by adding
some drying agent, an anhydrous inorganic salt that absorbs hydration water when
exposed to humid air or a humid solution, and thus, later, it is removed by
filtration. (ENGEL, 2012)
Extraction can be simple or multiple. A simple extraction is performed on only
one step, that is, we determined the volume of the solvent and carried out the extraction with everything.
this volume at once. On the other hand, multiple extraction involves two or more extractions.
simple.
According to Bruice (2006), there are two extraction techniques: continuous or discontinuous.
If the substance is more soluble in the organic solvent than in water, the method used is
discontinuous, which consists of shaking an aqueous solution with an organic solvent in a funnel
of separation, in order to extract a certain substance. Otherwise, the method is used
continuous, in this technique the soxhlet type extractor is used. The choice of solvent will depend on the
solubility of the substance to be extracted and the ease with which the solvent can be
separate from the solute.

2. OBJECTIVES
Extract acetic acid (HAc) using organic solvent and compare the efficacy between the
simple and multiple extraction techniques.

3. MATERIALS AND REAGENTS

50mL volumetric flask;
Graduated pipette; Distilled water;
10mL volumetric pipette; Standard solution of hydroxide
Erlenmeyer sodium (NaOH) 0.25M;
50mL graduated cylinder; 4% acetic acid (v/v)
250mL separation funnel; (CH₃COOH)
Universal support; Indicator solution of
50mL burette; phenolphthalein
Ring with sleeve; Ethyl etherC4H10O)
Claw with a cuff;

4. EXPERIMENTAL PROCEDURE
A 4% (v/v) acetic acid solution was prepared by adding 2 mL of the acid into
a volumetric flask of 50mL filled with distilled water up to the meniscus mark.
After the homogenization of the solution, two 125mL flasks were filled with a
10mL aliquot of the prepared solution and a drop of the phenolphthalein indicator solution.
Next, a 50mL burette was filled with a standard solution of hydroxide.
0.25M sodium (NaOH) in order to titrate the acetic acid solution. Two were performed
titulations at this stage of the procedure.
Next, to initiate the simple extraction technique, a
10mL aliquot of the acid solution and 30mL of ethyl ether as an extracting solvent for a

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funnel of separation and shook it gently, holding it by its neck. While shaking the funnel the
two immiscible liquids generated pressure when mixed, and this pressure can force the
cap to the outside. In order to eliminate this pressure, the funnel was turned upside down.
he bent down and slowly opened the faucet. Repeating this same procedure until the noise
the two vapors are not to be heard anymore, as shown in (Figure 2).

Figure 2. The correct way to shake and aerate a separating funnel.

Source: (Engelet al. 2012).

Upon finishing mixing the two liquids, after a brief time it was possible to ascertain.
that the two immiscible solvents separated into two layers, thus, the process began
liquid-liquid separation process, where the aqueous phase was extracted through the faucet to
an Erlenmeyer is titrated with a drop of phenolphthalein and 0.25M sodium hydroxide.
Next, to carry out the multiple extraction, 10mL of the acid solution was added.
4% acetic acid (v/v) prepared earlier and extracted with three portions of 10mL of ether.
(totaling 30mL). As in the simple extraction technique, it was shaken several times, opening and
slowly closing the funnel tap to release the pressure. Upon checking that the phases
they had completely separated after a while, gathered in an erlenmeyer
all the aqueous phases obtained in each extraction and titrated with a drop of the indicator solution
phenolphthalein and 0.25M sodium hydroxide (NaOH).

5. RESULTS AND DISCUSSION

a. Preparation of the acidic solution.
Two aliquots of 10mL of the 4% (v/v) acetic acid solution were titrated with the
standard sodium hydroxide solution 0.25M. The endpoint of the phenolphthalein indicator
used in the class in question occurs when the solution ceases to be colorless (the medium is
acid) and turn pink (the medium is basic). This phenomenon was observed when the sample
acetic acid, which has acidic character, turned pink after the addition of hydroxide volume
the sodium necessary for the neutralization of the sample, indicating that the medium has become basic
at the end of the titration. The volumes obtained in the two titrations performed in the experiment can
to be observed in the table below:

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 Table 1: Volume of titrant (NaOH) used to neutralize acetic acid.

Titling Volume (mL)

1 28.5

2 28.3

Average of qualifications 28.4

Authorial

Thus, by substituting the average volume of the two titrations performed into the formula of
molar concentration is obtained by the number of moles of the NaOH solution 0.25M:

n
M= L

M = molar concentration (mol/L)

n = number of moles of the solution
L = volume of the solution (L)

By substituting the provided values, it is obtained that:

n
0.25M = 28.4 × 10⁻³ L

Therefore, the number of moles of NaOH present in 28.4 mL of this solution is 7.1 · 10-3mols. A
The chemical reaction of neutralization between acetic acid and sodium hydroxide is represented in reaction 1:

CH3COOH(aq)+ NaOH(aq)→ NaCH3COO(aq)+ H2O (Reaction 1)

From the reaction, it is possible to observe that 1 mole of acetic acid reacts with 1 mole of sodium hydroxide.
Thus, 7.1 · 10 will be necessary.-3moles of NaOH to neutralize the 7.1 · 10-3moles of CH₃COOH.
Knowing that the molar mass of acetic acid is 60.052 g/mol, it is possible to determine the mass of the compound.
through a rule of three:

1 mol CH₃COOH → 60.052 g/mol

7.1 · 10-3mols → x
x = 0.4264 g/mol CH₃Carboxylic acid

b. Simple extraction.
In general, the simple extraction technique consists of just a single step of
extraction, then 10 mL of acetic acid was extracted with 30 mL of ethyl ether,
being the extracting solvent, then acetic acid was titrated and 9 mL of hydroxide was used
sodium. It was observed through the chemical reaction (Reaction 1) that the proportion between the
The chemical species ratio is 1:1. Therefore, the number of moles of sodium hydroxide that reacts is equal to
to the number of moles of acetic acid:

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 0.25M → 1000mL
y → 9mL
y = 2.25 · 10-3mols CH₃COOH

When calculating that there was 2.25 · 10-3moles of acetic acid in the aqueous phase, became
it is possible to calculate its mass:
1 mol CH₃COOH → 60.052 g/mol
2.25 · 10-3mols → z
z = 0.1351gCH₃COOH

From this, the amount of acid mass extracted was determined and calculated.
percentage of acid that passed into the aqueous phase during extraction, allowing comparison of the
simple extraction technique with multiple extraction.

extracted mass: 0.4264 - 0.1351 = 0.2913g CH₃COOH

0.2913g
% of acetic acid extracted=
0.4264g × 100 = 68.32%

The choice of an appropriate solvent is a determining factor in cost and effectiveness.

of the liquid-liquid extraction process. The chosen solvent must exhibit a high
degree of selectivity and difference in solubility for the solute, otherwise, it is necessary to
use of a large amount of solvent. To extract a substance from an aqueous phase,
An organic solvent that is immiscible with water should be used. For example, ether.
ethanol that we use in practice. The solvents that have a density lower than that of the
water (1.00 g/mL), as shown in (Figure 1), will form the upper layer in the separation,
when shaken with water. The solvents that have a density greater than that of the
water will remain in the lower layer during separation. Thus, ethyl ether with a density equal
a 0.71 g/mL will remain in the upper layer, making up the organic phase (ENGEL, 2012).
In addition, ethyl ether has dipole-dipole type intermolecular interaction and the
acetic acid (Figure 3) a hydrogen bond. This means that CH₃COOH has
greater chemical affinity with ethyl ether in a solution with water, because of the polarity of
both is close, following the general rule 'like dissolves like'. The formation
two layers occur when CH₃COOH migrates to the ether solution, causing the
water obtains the unpaired electron pair found in oxygen, increasing its
degree of polarity, thus being less beneficial for acetic acid.
Acetic acid is considered weak because only part of the H+ the acid is ionized, thus
becoming easier your reaction with ethyl ether. Another aspect that contributes to the
solvent extraction is the nature of the carboxylic acid. In this sense, its performance
it depends on the number of carboxylic groups present in the molecule, on the size of the
chain and the strength of the acid. (BRUICE, 2006)

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 Figure 3. Structural formula of acetic acid

Source: Google Images

c. Multiple Extraction.
Similarly to the technique previously explained, the titration of the acid was carried out.
acetic with sodium hydroxide, 6.5 mL of the base was used, and the number of was determined
moles of acid, as shown below:
0.25M → 1000mL
w → 6.5 mL
w = 1.625 · 10-3molsCH₃COOH

When we find the amount of moles, being 1.625 · 10-3moles of acetic acid,
the mass of the solute was determined:
1 mol CH₃COOH → 60.052 g/mol
16,250-3mols → m
m = 0.0975gCH₃Carboxylic acid group

Subsequently, the amount of mass of the extracted acid was determined and calculated.
percentage of acid that passed to the aqueous phase during multiple extractions.

mass extracted: 0.4264g - 0.0975g = 0.3289g CH₃COOH

0.3289g
% of acetic acid extracted= × 100 = 77.13%
0.4264g

According to Constantino (2011), multiple extraction tends to be more effective when

compared to simple extraction. When analyzing the results obtained in practice in
It was found that the simple extraction technique resulted in a yield of 10%.
below when compared to the subdivision of the extractions, since the acetic acid that remained
in the aqueous phase after the first extraction, it was re-distributed, dissolving in the new
ether solution, with the same partition coefficient, being extracted for a second time
with the help of the organic solvent, and so on with each extraction. That is, how much
the greater the number of small extractions, the greater the amount of solute removed.

6. CONCLUSION

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 Through the experiments carried out in this practice, we concluded that the extraction with
Solvents are a widely used method for the separation of substances, provided that
present a difference in solubility, and in this case, we have a viable option to choose
of ethyl ether as an extracting solvent, as the removal of acetic acid was shown to be possible.
Another conclusion for this work is that the multiple extraction technique was more
efficient, according to the results presented, even if it does not reach 100% performance
(due to reagent losses). Its efficiency lies in using solvent in small extractions,
thus a greater amount of solute is removed. It is an easy production technique,
considerably efficient in the process of separating substances in a mixture.

7. REFERENCES
[Link], Randall G. et al. Experimental organic chemistry: scale techniques
small. 3rd ed. São Paulo: Cengage Learning, 2012.

[Link], Maurício Gomes; SILVA, Gil Valdo José da; DONATE, Paulo
[Link] de química experimental.2. ed. São Paulo: EDUSP, 2011.

[Link], Paula [Link]ímica orgânica:volume 1. 4. ed. São Paulo: Pearson

Prentice Hall, 2006. xxx, 590 p. ISBN 9788576050049 (paperback).