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Lab Report 1

The document describes the production of aniline through a multi-step process. Nitrobenzene is reduced using tin and hydrochloric acid to produce aniline hydrochloride. This is then treated with sodium hydroxide to liberate aniline. The aniline is purified through extraction with ether and distillation. The percentage yield of aniline obtained is 62.67%, which is considered acceptable.

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Kartik Pillay
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89 views4 pages

Lab Report 1

The document describes the production of aniline through a multi-step process. Nitrobenzene is reduced using tin and hydrochloric acid to produce aniline hydrochloride. This is then treated with sodium hydroxide to liberate aniline. The aniline is purified through extraction with ether and distillation. The percentage yield of aniline obtained is 62.67%, which is considered acceptable.

Uploaded by

Kartik Pillay
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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PRODUCTION OF ANILINE

AIM:
Reducing NO2 to produce NH2 using tin and hydrochloric acid to form aromatic amine.

INTRODUCTION:
Aniline is a compound that contains NH 2 group on the benzene. It is a primary aromatic amine that has a
weak base and forms salt with mineral acids for instance hydrochloric acid. Reduced nitrobenzene is
used to make aniline. An aniline molecule comprises a nitrogen atom with a lone pair of electrons that
readily donate electrons. As a result, the benzene ring is activated, allowing the electrophilic aromatic
substitution reaction to proceed more quickly. As aniline is converted to aniline hydrochloride in acidic
conditions, a quick distillation is used to purify the aniline. Thus, in this experiment hydrochloric acid and
tin will be used to reduce NO2 to produce NH2.

PROCEDURE:
A 500cm3 round bottom flask with a reflux condenser was filled with 6g of nitrobenzene and 11g of
granulated tin. Tiny portions of 25cm3 concentrated hydrochloric acid were added down the top of the
condenser, and the flask was twirled to blend the contents with each addition. The mixture warmed up
and began to boil. After a vigorous reaction the flask was let to cool down.

After all of the hydrochloric acid had been applied and the reaction had died down, the flask was heated
for about 30 minutes with continuous stirring while the condenser was still connected to the steam
bath. During this course, aniline chloride was formed from stannic chloride, resulting in a yellowish solid.

The reaction mixture was slightly cooled and 12.5cm 3 water added and the 17.5g of NaOH solution was
gradually added in 30cm3 water making sure that the reflux condenser is still attached. After all the
hydroxide had been added a litmus paper was used to determine if the solution was strongly alkaline.

For stem distillation, the flask was rearranged. The milky distillate was retrieved as an aniline suspension
in water. The milky distillate was collected until it became visible, then the distillation was stopped after
5 minutes.

The distillate was mixed together with enough NaCl salt to make a saturated solution. After that, 10cm3
of ether was applied to the saturated solution in a separating funnel. The mixture was swirled until the
aniline was fully dissolved in the ether layer. A dry 250cm3 conical flask was used to collect the ether
layer.

After that, the aqueous solution was poured back into the separating funnel. The aqueous layer also
retained some aniline that needed to be re-extracted in order to ensure that the aniline was removed.
The previous move was then replicated twice more. The ether extract contained crude aniline with
traces of water that were extracted with anhydrous K2CO3, eliminating the cloudiness as well.

The dry ether extract was filtered into a 100cm3 round bottom flask, and the ether was extracted using
a rotary evaporator. The crude aniline-filled round bottom flask was assembled for low-pressure vacuum
distillation.
The distillate was collected, and the temperature and pressure ranges were
measured. The filtered aniline yield was estimated.

RESULTS:
Data Table: Showing reagent used in the experiment and product formed.
Reagents Classification Mr Mass Moles Volume Density Solubility
(MSDS) (g/mol) (g) (mol) (ml) (g/cm3)
Nitroben Extremely poisonous 123.11 6.0 0.0487 5.50 1.203 Slightly soluble in water
zene
Tin(Sn) Harmful effect on 118.71 11.0 0.0927 80.41 7.31 Insoluble in water
human nervous
system
HCl Very hazardous 36.46 28.60 0.784 25.0 1.189 Soluble
NaOH Corrosive chemical 39.997 17.49 0.437 37.25 2.13 Soluble
Ether Flammable substance 74.12 22.48 0.303 30.0 0.71 Slightly soluble
Aniline Hazardous product 93.13 3.76 0.0670 3.84 1.021 Moderately soluble

Percentage Yield:
% yield = (actual yield/theoretical yield) ×100

= (3.76/6) ×100
= 62.67%

QUESTIONS:
1. Equation of aniline liberated upon addition of sodium hydroxide.
C6H5NH3 + OH- C6H5NH2 + H2O

2. Anhydrous magnesium is not a very good drying agent to dry ether solution of aniline because it
exists as stable crystal and therefore, the packing fraction is very low and thus cannot accept the
water molecule.

3. Since, aniline in an organic compound and it will dissolve into ether layer. Since, ether is denser
than water, the aniline that was collected from steam distillation will settle at the base forming
the bottom layer.

CONCLUSION:
From the above experiment, aniline, an organic compound was formed by reducing nitrobenzene using
granulated tin and hydrochloric acid. The product has many uses in real life situations and also has
hazards related to it. In this lab, the desired product was formed which had a percentage yield of 62.67%
which was quite okay since there could have been factors that had affected the yielding of the final
product.

REFERENCE:
https://www.britannica.com/science/aniline

https://genuinechemistry.com/2019/05/aniline-uses-properties-lab-preparation.html

https://www.youtube.com/watch?v=62HL5vGcsos

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