Basra University College of science and Technology

Pharmacy department

Organic Chemistry

Title of Report :-
Extraction
Student Names :

‫علي مكي عبد الحسن‬

Supervised by:

Dr: Ahmed makki

theory:
Extraction in chemistry is a separation process consisting in the separation of a
substance from a matrix. Common examples include liquid-liquid extraction, and
solid phase extraction. The distribution of a solute between two phases is an
equilibrium condition described by partition theory. This is based on exactly how
the analyte moves from the initial solvent into the extracting solvent. The term
washing may also be used to refer to an extraction in which impurities are
extracted from the solvent containing the desired compound.
Extraction is the first step to separate the desired natural products from the
raw materials. Extraction methods include solvent extraction, distillation
method, pressing and sublimation according to the extraction principle.
Solvent extraction is the most widely used method.

Types of extraction:

1. Liquid-Liquid Extraction
A liquid-liquid extraction either transfers an organic compound that is dissolved in
an aqueous phase to an organic solvent, or it is used to transfer unreacted reactants,
salts, and other water-soluble impurities to the aqueous phase while leaving the
organic compound of interest in the organic phase. Immiscible liquids are liquids
that never form a homogenous solution, even when thoroughly mixed. Instead,
immiscible liquids separate into different phases, like oil and water.
2. Acid-Base Extraction
Acid-base extraction is a type of liquid-liquid extraction that separates organic
compounds based on their acid-base properties. If a solute is an acid or base, its
charge changes as the pH is changed. Generally, most organic compounds are
neutral, and therefore more soluble in organic solvents than they are in water.
However, if the organic compound becomes ionic, then it becomes more soluble in
water. This is useful in extracting an organic acid or base compound from an
organic phase to an aqueous phase.

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 3. Solid-phase extraction
The basic principles of SPE are similar to liquid–liquid extraction. Both
methods involve the distribution of dissolved species between two
phases. However, SPE involves the dispersion of the analyte between
a liquid (sample medium) and a solid (adsorbent) phase instead of the
two liquid phases which cannot be not mixed together as in liquid–
liquid extraction. This technique allows the enrichment and purification
of the analytes on a solid adsorbent through adsorption from the
solution.
4. Ultrasound Extraction
UAE uses acoustic waves in the kilohertz range that travel through the solvent
producing cavitation bubbles. When the cavitation bubbles burst at the surface of
the plant sample matrix, a shockwave-induced damage to plant cell wall enhances
the mass transfer of phenolic compounds across cellular membranes into solution.
5. Supercritical fluid extraction
Supercritical fluid extraction (SFE) is a green technology that has been applied on
a commercial scale for more than three decades. SFE is a high-pressure extraction
method in which a mixture of solutes is separated from a solid matrix by bringing
the mixture into contact with a fluid in the supercritical state. A supercritical fluid
has very particular and unique characteristics, which enable its use as an efficient
extraction solvent. Carbon dioxide (CO2) is the most commonly used supercritical
fluid and has applications in food, cosmetic, pharmaceutical, and correlated
industries.
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 solubilization extraction
Mechanochemical solubilization and mechanochemically assisted extraction of
plant bioactive compounds are discussed. The mechanochemical approach
advances are illustrated by examples of some phytosterols, phytoecdysteroids and
triterpenoid acids. The mechanical treatment of plant raw powder and solid
reagents is used for chemical transformation of bioactive substance into soluble
chemical form. In some cases it is possible to increase the extraction yield of
bioactive substance more than 50%, to elevate the selectivity of green product and
to simplify the following purification, to exclude the organic solvents from
technology.
8. Microwave-assisted extraction
MAE presents a heating mechanism that significantly reduces the extraction time
(usually from a few seconds to half an hour) compared to other techniques. This is
an advantage for avoiding thermal degradation and oxidation. In addition, MAE
consumes less solvents (easy recycled), presents higher extraction yield and
enhanced efficiency, is nontoxic, and can be used for larger volumes. MAE is one
of the simplest methods and most effective among the several existing techniques.
Nevertheless, the maintenance costs associated are still high.
9. Instant controlled pressure drop extraction
The instant controlled pressure drop (DIC) technology enabled both the extraction
of essential oil and the expansion of the matrix itself which improved solvent
extraction. The sequential use of DIC) triggered complementary actions
materialized by supplementary effects.
10. Maceration extraction
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.

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• 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

• 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:
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.

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Tools & Material:

Tools: –

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

Materials: –

1. Iodine crystal
2. NaoH
3. Chloroform
4. Distilled water
5. Benzoit acid
6. Potassium iodide
7. Grease
8. CHCL3
9. H2O

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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:

• The separating funnel lid is open because the top must be opened while
releasing the lower phase to allow pressure equalization between the inside of
the funnel and the atmosphere. When the bottom layer has been removed, the
stopcock is closed and the upper layer is poured out through the top into another
container.

• chloroform is used as a solvent for benzoic acid because 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.

• Acid does not dissolve in water while its salt dissolves because 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. The solubility
of many compounds depends strongly on the pH of the solution. For example,
the anion in many sparingly soluble salts is the conjugate base of a weak acid
that may become protonated in solution. In addition, the solubility of simple
binary compounds such as oxides and sulfides, both strong bases, is often
dependent on pH. In this section, we discuss the relationship between the
solubility of these classes of compounds and pH.

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

• Sodium hydroxide (NaoH) 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.

• 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:

• Harris, D.C. (2015). Quantitative Chemical Analysis. New York,

NY: W.H. Freeman and Company.
• "4: Extraction". Chemistry LibreTexts.
• Graphical User Interface, (GUI) (2015-11-27). "Topological
Analysis of the Gibbs Energy Function (Liquid-Liquid
Equilibrium Correlation Data. Including a Thermodinamic
Review and Surfaces/Tie-lines/Hessian matrix analysis)".
University of Alicante
• Evarts, Holly. "Radical Desalination Approach May Disrupt the
Water Industry". Columbia Engineering.

• Patel, Madhav; Karamalidis, Athanasios K. (May 2021).

"Germanium: A review of its US demand, uses, resources,
chemistry, and separation technologies". Separation and
Purification Technology: