Nitration

‫‪Names‬‬
‫كيرلس عبدهللا ذكي‬ ‫‪o‬‬
‫كيرلس ايمن ايليا فهيم‬ ‫‪o‬‬
‫حبيب جمال حبيب‬ ‫‪o‬‬
‫مينا اسام خليل‬ ‫‪o‬‬
‫احمد هانى على حسن‬ ‫‪o‬‬
‫احمد حسن ابراهيم‬ ‫‪o‬‬
‫محمود رضا محمد‬ ‫‪o‬‬
‫حسام حسن يوسف‬ ‫‪o‬‬
‫اكرامى السيد مهدى‬ ‫‪o‬‬
‫عطيه بدر عطيه‬ ‫‪o‬‬
 TABLE OF
0 CONTENTS
Nitration of 02 of
Nitration 03 of
nitration
1
alkanes alkenes alkynes

04 of
Nitration 05products
nitration
aromatic industry
 introduction

o Nitration involves the introduction of one or

more nitro groups into reacting molecules
using various nitrating agents like fuming,
concentrated, aqueous nitric acid mixture of
nitric acid and sulphuric acid in batch or
continuous process.
o Nitration products find wide application in
chemical industry as solvent, dyestuff,
explosive, chemical intermediates.
 Reagent
o Nitric acid (HNO3) is the primary reagent for nitration. It acts as
a slow electrophile on its own, particularly with weak
nucleophiles like benzene. However, for aromatic rings with
strong activating groups like phenol, HNO3 alone is sufficient for
nitration.

o The addition of an acid, typically sulfuric acid (H2SO4),

accelerates the reaction with benzene significantly.

o The critical step in this process involves the protonation of the

OH group on nitric acid, converting it into H2O. This conversion
is crucial, as H2O is a much better leaving group than HO(-),
leading to the formation of the highly reactive "nitronium ion"
(NO2+).
 Nitration of alkanes
Nitration is a process in which a nitro group, –NO2, is introduced into an organic compound, such as an
alkane. This reaction generally involves the substitution of a hydrogen atom by the nitro group. Nitration
of alkanes is a type of electrophilic substitution reaction that typically occurs under conditions of high
temperature and pressure.
 mechanism of nitration
• Step 1: Formation of Nitronium ion.
The reaction begins with the formation of the nitronium ion, which serves as the
electrophile in the process. This is achieved by the protonation of nitric acid (HNO3) in the presence
of a strong acid like sulfuric acid (H2SO4), leading to the creation of the nitronium ion and water
• Step 2: Nucleophilic Attack.
The alkane molecule undergoes a nucleophilic attack where it donates its electrons to the
positively charged nitronium ion. This reaction leads to the formation of a nitro alkane and the
regeneration of the catalyst.
• Step 3: Termination Stage.
The reaction process ends once the desired level of nitration has been achieved.
Essentially at this stage, no new compounds are formed.
 Nitration of alkanes
Example 1: Nitration of methane. Example 2: Nitration of Ethane.

o The nitration of methane is an essential o Ethane undergoes nitration in an

industrial process, which, under regular industrial setting, specifically in the
conditions, is highly endothermic and production of nitroethane, an essential
slow. However, in the presence of a chemical in the synthesis of a variety of
catalyst and under high pressure and substances, including pharmaceuticals,
temperature conditions, it becomes and an effective solvent in industrial
feasible. The balanced chemical equation applications. The reaction of nitration in
for this reaction can be written as ethane can be represented as

CH4 + HNO3 → CH3NO2 + H2O C2H6 + HNO3 → C2H5NO2 + H2O

 Nitration of alkenes
Nitration of alkenes involves the addition of a nitro group (NO2) to the carbon-carbon double bond of an
alkene. This reaction typically requires a strong acid catalyst, such as sulfuric acid (H2SO4), and a nitrate
salt, such as potassium nitrate (KNO3).

 mechanism of nitration
• Step 1: Protonation of the alkene.
The alkene (ethane) reacts with a strong acid catalyst, usually sulfuric acid (H2SO4), to form a
carbocation intermediate. This step is often the rate-determining step of the reaction.
• Step 2: Attack of the nitronium ion.
The carbocation intermediate (ethyl carbocation) is attacked by the nitronium ion (NO2+) from
nitric acid (HNO3) to form a sigma complex.
• Step 3: Deprotonation.
: The sigma complex undergoes deprotonation to form the final product, 1-nitroethane, and
regenerate the acid catalyst
 o A general equation for the nitration of an alkene:

RCH=CH2+HNO3+H2SO4→RCH (NO2) CH3+H2O

Products & Uses

o nitroethane is utilized as a chemical intermediate for pharmaceuticals,
agrochemicals, and specialty chemicals. And an ingredient in explosives
and a solvent in industries such as polymer production.

o nitropropane, which can be used as a solvent, in organic synthesis, and as a

fuel additive.
 Nitration of alkynes
o The nitration of alkynes typically involves the reaction of the
alkyne with a mixture of nitric acid (HNO3) and sulfuric acid
(H2SO4). The nitronium ion (NO2+), generated in situ by the
protonation of nitric acid by sulfuric acid, acts as an
electrophile that attacks the triple bond of the alkyne.

o The general reaction can be represented as follows:

o Examples of the reaction :

• Nitration of Acetylene (Ethyne)

3C2H2 + HNO3 → H2O + C6H5NO2

• Nitration of propyne

CH3C≡CH+HNO3→CH3C(NO2)CH+H2
 Nitration of aromatic
mechanism of nitration
Step 1: Nitric acid accepts a proton from sulfuric acid and then dissociates to form nitronium ion.

Step 2: The nitronium ion acts as an electrophile in the process which further reacts with benzene to form an
arenium ion which is unstable.

Step 3: The arenium ion then loses its proton to Lewis base forming nitrobenzene using water or HSO 4- from
the former step.
Factors Influencing the Nitration Mechanism
The efficiency and output of the nitration process are not just dictated by the reactants
and their proportions, but also by a number of controllable factors.

 Temperature  Catalyst
Higher temperature tends to Specific catalysts can
increase the rate of nitration by dramatically speed up nitration
providing the necessary energy reactions.
for the reaction

 Pressure  Solvent
an increase in pressure usually polar solvents tend to enhance
push the reaction to proceed at a the rate of reaction due to their
faster rate. ability to stabilise ionic species

 Concentration of Nitrating Agent

Nitration reactions usually require a
high concentration of the nitration agent
to proceed efficiently
Nitration products
industry
o Nitration processes play a crucial role in
various industries. Let's explore some of
the uses and applications

o nitration processes contribute

significantly to various industries,
ranging from pharmaceuticals to
explosives, enabling the synthesis of
essential products and materials
 Nitration products
1. industry
Pharmaceuticals: Nitroaromatic compounds serve as intermediates in pharmaceutical synthesis. They
contribute to the production of medications and drugs that benefit human health.
2. Plastics: Nitroaromatics find application in the synthesis of plastics. These compounds play a role in
creating durable and versatile plastic materials used in everyday products.
3. Dyes: Nitration reactions are essential for producing dyes. By introducing nitro groups into organic
molecules, vibrant and colorfast dyes are synthesized for textiles, printing, and other applications.
4. Insecticides: Nitroaromatics are utilized in the formulation of insecticides. These compounds help
control pests and protect crops, contributing to agricultural productivity.
5. Explosives: Nitration processes are most famously associated with the production of explosives. For
instance: TNT (2,4,6-trinitrotoluene) is synthesized from toluene through nitration. TNT has been
widely used as an explosive in military and industrial applications. Other explosive compounds include
picric acid, nitroglycerine, nitrocellulose, and RDX.
6. Solvents and Synthons: Nitroaliphatics serve as solvents and building blocks (synthons) in organic
synthesis. They facilitate the creation of complex organic molecules.
7. Ammonium Nitrate Production: Although often associated with organic compounds, nitration also
includes the production of ammonium nitrate from ammonia and nitric acid. Ammonium nitrate is a
critical component in fertilizers and explosives.