PREPARED BY

‫علي ماجد محمد حسن‬

Gr 10.

Date:2021\6\14

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 Theory

• Extraction in chemistry is a chemical separation process, in which

a so-called extracting agent or extractor (which can be in a gaseous, liquid,
solid or supercritical state) is used by performing a selective separation
process of one or more components within a mixture (And (which can be in
the gaseous, liquid, or solid state).
The product of the extraction process is called the extract (and sometimes
by the common name extract). Extraction is a process encountered in daily
life, as it is encountered in a coffee machine while extracting aromatic
compounds from coffee powder, and then conducting a filtering process at
the end Raising the temperature or pressure often increases the solubility
of the material to be extracted.
• Types of extraction
1) Liquid–liquid extraction
Liquid–liquid extraction (LLE), also known as solvent extraction and
partitioning, is a method to separate compounds or metal complexes, based
on their relative solubilities in two different immiscible liquids, usually
water (polar) and an organic solvent (non-polar). There is a net transfer of
one or more species from one liquid into another liquid phase, generally
from aqueous to organic. The transfer is driven by chemical potential, i.e.
once the transfer is complete, the overall system of chemical components
that make up the solutes and the solvents are in a more stable configuration
(lower free energy). The solvent that is enriched in solute(s) is called
extract. The feed solution that is depleted in solute(s) is called the raffinate
2) Solid-phase extraction
Solid-phase extraction (SPE) is an extractive technique by which
compounds that are dissolved or suspended in a liquid mixture are
separated from other compounds in the mixture according to their physical
and chemical properties. Analytical laboratories use solid phase extraction
to concentrate and purify samples for analysis. Solid phase extraction can
be used to isolate analytes of interest from a wide variety of matrices,
including urine, blood, water, beverages, soil, and animal tissue

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 3) Acid-base extraction
Acid–base extraction is a procedure using sequential liquid–liquid
extractions to purify acids and bases from mixtures based on their
chemical properties. Acid–base extraction is routinely performed during
the work-up after chemical syntheses and for the isolation of compounds
and natural products like alkaloids from crude extracts. The product is
largely free of neutral and acidic or basic impurities. It is not possible to
separate chemically similar acids or bases using this simple method.
4) Supercritical fluid extraction
Supercritical fluid extraction (SFE) is the process of separating one
component (the extractant) from another (the matrix) using supercritical
fluids as the extracting solvent. Extraction is usually from a solid matrix,
but can also be from liquids. SFE can be used as a sample preparation step
for analytical purposes, or on a larger scale to either strip unwanted
material from a product (e.g. decaffeination) or collect a desired product
(e.g. essential oils). These essential oils can include limonene and other
straight solvents. Carbon dioxide (CO2) is the most used supercritical fluid,
sometimes modified by co-solvents such as ethanol or methanol. Extraction
conditions for supercritical carbon dioxide are above the critical
temperature of 31 °C and critical pressure of 74 bar. Addition of modifiers
may slightly alter this. The discussion below will mainly refer to extraction
with CO2, except where specified
5) Ultrasound-assisted extraction
Ultrasound extraction is the preferred method for the isolation of bioactive
compounds from plants. Sonication achieves complete extraction thus
superior extraction yields are obtained in a very short
extraction time. Being such an efficient extraction method, ultrasonic
extraction is cost- and time-saving, while resulting in high-quality extracts,
which are used for foods, nutritional supplements and pharmaceuticals .
6) Heat reflux extraction (HRE)
process with cyclohexanone (CYC) in a high-performance mass transfer
extractor was applied to dissolve Shenmu-Fugu high-volatile bituminous
(SFHB) coal for the first time to afford extract € and extract residue (ER)
from the extraction.

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 7) Mechanochemical-assisted extraction
Extract the bioactive compounds efficiently and safely is a central issue in
modern food and pharmaceutical industry. Mechanochemical assisted
extraction is an innovative effective and eco-friendly extraction technology,
which has shown a great prospect in the industry and biotechnological
research. By this method, mechanochemical pretreatment allowed physical
and chemical transformations of target compound to improve its water
solubility and accelerated extraction efficiency markedly
8) Maceration
Maceration is an extractive technique that is conducted at room
temperature. It consists of immersing a plant in a liquid (water, oil, alcohol,
etc.) inside an airtight container, for a variable time based on the plant
material and liquid used. … The plant material can be used fresh or dry
based on the desired product.
9) Microwave Assisted Extraction
Microwave-assisted extraction (MAE) is a process of using microwave
energy to heat solvents in contact with a sample in order to partition
analytes from the sample matrix into the solvent.
10) Instant controlled pressure drop extraction
Was invented as a drying and decontamination food process. This process
is based on the thermomechanical effect induced by a rapid pressure drop
leading to instant evaporation of water and inactivation of vegetative
bacteria and spores. DIC technology is distinguished by its ability to handle
a wide range of solid food products. In addition, this process results in
volume expansion and positive texture modification. Preservation of
sensory aspects and nutriment compounds of food products was also
reported using this technology. Based on the DIC technology, many
industrial projects were realized and several patents were filed . The DIC
technology as a food drying and microbial decontamination process is
reviewed in this chapter was invented as a drying and decontamination
food process. This process is based on the thermomechanical effect induced
by a rapid pressure drop leading to instant evaporation of water and
inactivation of vegetative bacteria and spores. DIC technology is
distinguished by its ability to handle a wide range of solid food products. In
addition, this process results in volume expansion and positive texture
modification.

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Preservation of sensory aspects and nutriment compounds of food products
was also reported using this technology. Based on the DIC technology,
many industrial projects were realized and several patents were filed [15].
The DIC technology as a food drying and microbial decontamination
process is reviewed in this chapter
• Extraction is one of the methods of separation, and the extraction
of a compound depends on the chemical or physical properties of the
components of the mixture present in this compound.
There are several reasons for using extraction in a chemistry lab. It is a
major method of isolating compounds from plant materials. Extraction
transfers compounds from one liquid to another, so that they can be
processed or concentrated more easily. It also enables the selective removal
of components in a mixture. It has many uses for its purpose: [3]
Extraction is used to separate the components of the mixture using an
appropriate solvent (the solvent is selected so that it dissolves one substance
completely or significantly and does not dissolve the other substance). It is
used to purify organic substances from impurities, and this is done by
placing the substance to be purified between two immiscible solvents, and
this depends on the solubility of the substance or the separation factor
between them. It is used to separate dissolved substances from their
solutions or from a mixture, if the substances in the purification of an
impurity substance, if they are acidic, they are washed with sodium
bicarbonate.
• Solvent conditions for extraction:
The solvent does not mix with the solution in which the compound is
located.
The solvent does not interact with the components of the mixture.
Ease of separation of the solvent from the compound dissolved in it.
The diffusion coefficient of the solvent is appropriate for the compound to
be separated, and not suitable for the impurities.

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 Material and Tools

Apparatus :

1)Stand
2)Ring clamp
3)Separatory funnel 250 ml
4)Beaker 100 ml
5)Graduated cylinder 50 ml
6)Road glass
7)Watch glass
8)Conical flask 100 ml
9)Washing bottle

Chemical :

Iodine crystal
Potassium iodide
Chloroform
Distilled water
Grease
CHCL3
NaoH
H2O
Benzoit aci

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 Procedure

1- Transfer approximately 3-5 mg (about a spoonful) of a mixture of both

organic benzoic acid (white powder) and organic base m-nitro aniline
(yellow powder) into a conical flask.

2- We add 50 ml of chloroform to the mixture (in the conical flask) and

shake until the mixture dissolves.

3- Transfer the contents of the Erlenmeyer flask to the separating funnel

(make sure that the spout of the separating funnel is working properly and
the stopper of the funnel is closed).

4- We add to the separating funnel 20 ml of a 10% NaOH solution, stir the

funnel for 5 minutes, taking into account the pressure inside the funnel. In
this step, the added base NaOH reacts with the organic acid benzoic acid to
give sodium benzoate and water. Shaking is done in this step in order for
the reaction to take place and the salt formed from the organic layer
(consisting of the organic acid dissolved in chloroform) is transferred to the
aqueous layer (consisting of the base NaOH). Notice ; The salt formed
dissolves in water, so it moves from the organic layer to the aqueous layer.

5- After agitation for 5 minutes, the funnel is fixed perpendicular to the

holder and the cover of the funnel is removed, then the organic and
aqueous layers begin to separate, the upper layer is the aqueous layer, and
the lower layer is the organic layer (higher density)
6- We open the tap slowly and start separating the aqueous layer in one cup
and the organic layer in another (we put a label on the cup so that the cups
do not mix)

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Data

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 Discussion

• Why was chloroform used as a solvent for benzoic acid?

The use of chloroform as a solvent is common in the laboratory because it
is relatively unreactive, immiscible with most organic liquids, and is
suitably volatile. Chloroform is used as a solvent in the pharmaceutical
industry, dyes and pesticides production. Chloroform is an effective
solvent for base-form alkaloids, and therefore plant material is usually
extracted with chloroform for pharmaceutical treatment.
Where chloroform was used as a solvent for benzoic acid in the extraction
experiment, to hide the substance (benzoic acid), when it was added to it in
a conical flask, by shaking the conical flask several times to make the
substance disappear and gradually dissolve.
• Why is the separating funnel lid open
Pressure builds up during mixing if a reaction occurs with a gas or a
physical change occurs. This problem can easily be addressed simply by
opening the cap on top of the funnel because it is mixed.
• Acid does not dissolve in water while its salt dissolves?
The main reason for its weak solubility in cold water is the polar carboxyl
group present in it, and the largest part of the benzoic acid molecule is in
the non-polar form, meaning that there is only the carboxylic group that is
polar in it.
While salt dissolves because it is an ionic component, that is, it contains
molecules that carry an electrical charge called ions. When ionic
compounds dissolve in water, the ions separate to be surrounded by water
molecules, a process called "dissolution".
• Why did we added NaoH
Sodium hydroxide was added to the benzoic acid to form an aqueous layer
H2O and an organic layer (sodium benzoate salt). Where the solubility of
sodium benzoate is good in water

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 • why did we added HCL acid
When HCl is added, a salt will be formed HCl reacts with the aqueous
layer to form the salt and is separated by filtration

• Why are there two layers?

Due to the different solubility of each layer, two layers are formed, the
heaviest at the bottom and the lighter at the top of the funnel

References

[1] Muhammad Subaie Murad, Organic Chemistry, Al-Baath University

5991.

[2] Muhammad Ali Al-Shaar, Oil Technology (1), Al-Baath University 2005 –
2006

[3] J. M. Sànchez, M. Hidalgo, M. Valiente and V. Salvadò, Solvent

Extraction and Ion Exchange, 1999.

[4] The New Illustrated Dictionary of Science.” Library of Lebanon

Publishers