Activity No.

Separating Components of a Mixture by

Extraction

Group 4
Montes, Marie Therese Ann J.
Magan, Quinone
Mocorro, Maria Aiza L.
Obsioma, Jade A.
Perez, Jhonna lyn B.

BS Chemistry 2H1

Organic Chemistry Laboratory 1

Anorico, Nova Fe E.

November 8, 2021
 INTRODUCTION

1.1 Rationale of the Experiment

Separation of mixtures uses variety of techniques. There are three kinds of
separation techniques: Distillation, Chromatography, and Extraction. Distillation
separates by boiling point, chromatography separates by polarity, while Extraction
separates based on solubility. One of the most used separation technique in laboratories is
extraction.
In the extraction process, a solute is transferred from one phase to another to
separate it from unreacted starting materials or impurities. Extraction is also used to
facilitate the isolation of a solute from a reaction solvent that is difficult to remove by
evaporation, such as a solvent with a high boiling point (Harris, D.C., 2015). When the
mixture is placed inside the separatory funnel, solutes dissolve in two layers – the
aqueous layer and the organic layer. In this case, extraction takes place as the components
of the solution moves from a layer to another layer.
The first mixture involves sodium chloride and cholesterol. Sodium chloride,
also known as salt, is an ionic compound that is soluble in water while cholesterol is a
type of body fat or lipid residing in blood plasma and tissues, which is insoluble in water.
The second mixture involves 4-chloroaniline, benzoic acid, and 1,4-dibromobenzene. 4-
chloroaniline is a weak base, benzoic acid is a weak acid, while 1,4-dibromobenzene is a
neutral compound. These three compounds differs less in their solubility. Therefore,
separating these three compounds requires acid-base extraction. The purpose of this
experiment is to separate the components of the mixtures involve by extraction.

1.2 Objective of the Experiment

The objective of this experiment is to separate mixtures by extraction. The objectives are
as follows:
1. To demonstrate separation of mixture with different solubility
2. To demonstrate separation of mixture with the same solubility
3. To separate sodium chloride and cholesterol mixture based on their solubility
4. To separate 4-chloroaniline, benzoic acid, and 1,4-dibromobenzene mixture using
acid-base reaction
 MATERIALS AND METHODOLOGY

2.1 Materials/Experimental Set-up

The materials that were used when conducting the experiment are Sodium Chloride,

Cholesterol, Water, Ether, Erlenmeyer flasks, Separatory Funnel, Hot Plate, 4-chloroaniline,

Benzoic acidz 1,4-dibromobenzene, Stopcock, HCl, Sodium bicarbonate solution, Sodium

sulfate, Funnel and Sodium hydroxide.

2.2 Separating Components of a Mixture by Extraction Procedure

a) Sodium Chloride and Cholesterol

Both sodium chloride and cholesterol were crystalline white substances. To

separate the two, some water and ether were added to the mixture, as sodium chloride

is a water soluble compound and cholesterol is mainly insoluble in water. Water and

ether were whirled together for several moments before being poured into a

separatory funnel. The funnel had two layers, with the water remaining at the bottom.

The funnel was opened and the aqueous layer was emptied into a flask until it reached

the organic layer just barely. On the other hand, the funnel's top layer was emptied

into another flask. Finally, solvents were to evaporate in order to obtain the

compounds.

b) 4-chloroaniline, benzoic acid, and 1,4-dibromobenzene

Erlenmeyer flask was used to contain the mixture of 4-chloroaniline, benzoic

acid, and 1,4-dibromobenzene. The mixture were then dissolve in ether and

transferred over to the separatory funnel. Starting with the aniline, acid-base reaction

were used since the compound reacts with a strong acid. So, an aqueous HCl solution

were poured and were denser than the ether thus, it will pass right through and

collected on the bottom, forming an aqueous layer. To ensure that everything reacts

properly, a stopper was placed over a funnel, picked up and shook for a bit. This will

generate some pressure inside the funnel, so it was vented periodically by holding
upside down with a finger on the stopper, and turning the stopcock to release the gas

built up. This produce some audible sound. The stopcock was then closed and shake

some more, then vent again. The process were repeated until there were no noise

heard upon venting. The aqueous layer were then drained into a new labeled flask. To

be thorough, the organic layer were washed again with another portion of acid, and

the process were repeated. Then one more time with just deionized water, all of the

aqueous extracts were collected in the same flask. This results to an aniline salt in the

water that were set aside for a moment.

Benzoic acid and 1,4-dibromobenzene were left in the ether. The next step

were to add some base to the mixture of benzoic acid and dibromobenzene. The

aqueous sodium bicarbonate (NaHCO3) were then added. Similar to the previous

step, it was shaken, vented, and the aqueous layer was drained into another labeled

flask, washed again with base, and then again with just water. The benzoic acid salt

sitting in water were then put aside for a moment.

The 1,4-dibromobenzene in ether were left in the Separatory funnel and was

poured out through the top of the funnel into another new labeled flask to avoid

contamination. The empty funnel were then washed with a little ether and a drying

agent (sodium sulfate) were added to the flask. A funnel, together with a filter paper,

was used to transfer the solution into another flask. With all that, the mixture were

successfully separated into its three components. Below shows the experimental set-

up.
 Figure 2.1 Experimental set-up for extracting mixture

Figure 2.2 Experimental set-up for evaporating the solvent

 RESULTS AND ANALYSIS

Liquid-liquid extraction with different solubility

This section discusses the extraction of two or more liquids. Sodium chloride NaCl
and cholesterol C27H46O were employed in the experiment to demonstrate liquid-liquid
extraction. Sodium Chloride NaCl is a water-soluble ionic compound. Cholesterol C27H46O is
a nonpolar steroid that is insoluble in water but is highly soluble in nonpolar solvents.
Separation of these chemicals was based on their physical characteristics. To dissolve sodium
chloride NaCl, water was utilized, and ether was used to dissolve cholesterol C27H46O. Due to
the immiscibility of the solvents, the separatory funnel contained two layers. Because water is
denser than ether, the aqueous layer comprising water and sodium chloride lies at the bottom.
Following separation of the two layers, solvents were evaporated to recover sodium chloride
NaCl and cholesterol C27H46O.

Liquid-liquid extraction with the same solubility

If two solvents have the same solubility, their reactivity can be used to distinguish
them. Because 4-chloroaniline is a basic compound, it was separated from the other two
solvents using an acidic solution. The acid-based reaction was carried out using aqueous
hydrochloric acid HCl. Because hydrochloric acid HCl reacts solely with 4-chloroaniline, the
solution generated an aqueous layer at the bottom, which is denser than ether. While passing
through the organic layer, it will undergo acidic reactions, transferring protons to the aniline
molecule. After protonation of the aniline, the nitrogen atom will have a formal positive
charge. Whereas neutral aniline is insoluble in water, this aniline salt will be because the
formal charge can promote favourable

ion-dipole interactions with water. After draining the aqueous layer, another acid
reaction was used to separate the benzoic acid. Aqueous sodium bicarbonate was added to the
ether, which went through the organic layer and eventually formed an aqueous layer. Sodium
bicarbonate accepts a proton from benzoic acid as it passes through the organic layer. This
leaves the benzoate ion, which is extremely water soluble. Due to the fact that the negative
ion is capable of interacting with water molecules in solution. Benzoic acid was pulled into
the aqueous layer by the base. In a separate flask, collect the aqueous layer. The
dibromobenzene in ether that remained in the separatory flask was transferred to another
flask. To collect the substance, the three solvents were evaporated.
 Typically, acid-base extraction is used to separate organic molecules depending on
their acid-base characteristics. The approach is predicated on the premise that the majority of
organic compounds are more soluble in organic solvents than in water. When an organic
chemical is converted to an ionic state, it becomes more soluble in water than in the organic
solvent. These chemicals can readily be converted to ions by either adding a proton (an H+
ion) to form a positive ion or by withdrawing a proton to form a negative ion.
References
Extraction | Protocol. (n.d.). Retrieved onNovember 07, 2021 from
https://www.jove.com/science-education/11198/extraction
Explains, D. (2019, February 15). Separating Components of a Mixture by Extraction.
Retrieved
on November 07, 2021, YouTube.
https://www.youtube.com/watch?v=N96JaRnE7n0&feature=youtu.be
Schaller, C. Acid-Base Extraction. Retrieved on November 08, 2021 from
https://chem.libretexts.org/Ancillary_Materials/
Demos_Techniques_and_Experiments/General_Lab_Techniques/Acid-
Base_Extraction