Preparation Of Nitroacetanilide

Introduction:
Para nitroacetanilide is also called 4-Nitroacetanilide, para nitroacetanilide is a chemical compound
that is a nitroacetanilide derivative prepared from acetanilide and nitrating mixture. Along with para
product a trace of ortho product is also formed.

Aim:
To prepare p-Nitroacetanilide from acetanilide and acetic acid in the presence of nitrating mixture.

Equation

Procedure :
 1-Take 3gm of finely powdered acetanilide in a clean beaker and dissolve it by adding
glacial acetic acid by stirring the content carefully at room temperature.
 2-Gently warm the mixture to dissolve acetanilide completely.
 3-Cool the solution and add concentrated sulphuric acid slowly with constant stirring. The
solution becomes warm, keep the mixture in ice-bath and clear solution is obtained.
 4-To the cool solution add fuming nitric acid dropwise through a dropping funnel with
constant stirring.
 5-Maintain the temperature below 20oC during the whole process.
 6-Once the addition of nitric acid is completed, the beaker is removed from the freezing
mixture bath and allowed to stand for half an hour at room temperature.
 7-Pour the mixture into 100gm of crushed ice in a beaker and stir well.
 8-Large crystals of p-nitroacetanilide are obtained. Filter the crystals through filter paper.
 9-The separated p-nitroacetanilide is washed with cold water in order to remove excess of
acid.
 10-It is crystallized from ethyl alcohol. Dry the crystals in the folds of filter paper and weigh
them to know the yield.
 Properties
1. Physical properties :

2.Chemical properties:
 As p-Nitroacetanilide is a compound and not found naturally, several unique
methods and procedures are undertaken to develop the compound. Mainly, the
p-Nitroacetanilide is prepared via nitration of acetanilide. In nitration, the
acetanilide is processed and reacted via concentrated solutions of nitric and
sulphuric acids.

 Moreover, the glacial acetic acid is also used during preparation, as it possesses
the properties of a polar solvent, which regulates the acetanilide dissolving.
Additionally, ions of acetic acid are poor nucleophiles, which ensure that there
will be no substitution reaction during dissolving.

 In the overall process, an electrolytic substitution reaction would take place.

Lastly, the acetanilide is purified via the process of crystallisation.

3.Nitroacetanilide Uses:

 As discussed earlier, p-Nitroacetanilide has analgesic properties which is helpful

to the pharmaceutical industry to prepare several medications, like paracetamol.
Moreover, it is used to develop poultry medicines, anti-oxidants, gasoline,
pesticides, and rubber chemicals. Apart from this, a p-Nitroacetanilide hydrolysis
reaction is carried out, and it is synthesised to obtain the P-nitroaniline.
 It works as the reactant in a particular chemical reaction. The Reaction product is
used further as a reactant in other Reactions to develop dyes. Lastly, p-
Nitroacetanilide is also widely used in gum and corrosion inhibitors.