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Chemical Engineering Department

EXPERIMENT NO. : 02
“PREPARATION OF m-DINITRO BENZENE FROM BENZENE”

Aim : Preparation of m-dinitro benzene From Benzene

Apparatus : Conical flask, Water bath, measuring cylinder, separating funnel,


Thermometer, RB flask, etc.

Chemicals : Nitrobenzene, funnel, HNO3 acid, H2SO4 etc.

Theory : Substituent in aromatic compound influence the electron density


in two ways by inductive effect (-1 or +1) & by the mesomeric effect
(-m or +m). The inductive effect is associated with dipole moment
of the compound, if x is at (-) ve end of the dipole. It will draw
electron from the ring & produce (-1) effect. If x is at the (+) ve end
of the dipole, it will increase to electron density in the ring to
produce a (+1) effect.

The (-1) effect causes all the position in the ring to be more effective
& -1 effect reduces the reactivity of all the position in the ring
relative to become –m effect compounds which have +1 & +m gives
substitution & -1, -m gives meta substitution.

Procedure : In the RB flask carefully mix together 40 ml conc. H2SO4 & 40 ml


fuming HNO3. Add 30ml of N.B. in above mix. in 2-3 installations
with shaking the flask.

After completion of addition, heat the flask on water bath for about
an hour. Stop the heating & keep the flask for 5 min. Pour the
liquid on 500 ml beaker containing 200 ml water. Stir the mix.
yellow ppts of m-dinitro benzene separate out, filter & wash with
water. Recrystallise with water take melting point.

Purification : Transfer the product in a RB flask with reflux condenser, add


acidified spirit 40-50ml & heat on a water bath to obtain a clear
solution. Filter the content & collect the crystals deposited on
cooling & dry it. Check the melting point compare it with the
melting point given in literature & text book.

Reaction :

1 PREPARATION OF m-DINITRO BENZENE FROM BENZENE


Chemical Engineering Department

Properties : meta-dinitrobenzene is yellow crystalline powder, M.P. =89.8 0C,


B.P. = 303 0C at 760 mmHg

Application : Used in dyes, dyestuff & pharmaceutical industries as a


intermediate.

Result : (1) Theoretical wt of meta-dinitrobenzene is =


(2) Practical wt of meta-dinitrobenzene is =
(3) % yield of meta-dinitrobenzene is =

2 PREPARATION OF m-DINITRO BENZENE FROM BENZENE


Chemical Engineering Department

Observations :-
(1) Volume of nitrobenzene solution =
(2) Volume of conc. H2SO4 solution =
(3) Volume of conc. HNO3 solution =
(4) Specific gravity of nitrobenzene =
(5) Wt of meta-dinitrobenzene =

Calculation :-

Wt of nitrobenzene = vol. of nitrobenzene * sp gravity of N.B.

(1) Theoretical yield of meta-dinitrobenzene

123 gm N.B. → 168 gm m-diN.B


36 gm → ?

(2) Practical yield of meta-dinitrobenzene =___________

(3) % yield of meta-dinitrobenzene

= (Practical wt of m-di N.B obtained/Theoretical yield)*100

3 PREPARATION OF m-DINITRO BENZENE FROM BENZENE


Chemical Engineering Department

4 PREPARATION OF m-DINITRO BENZENE FROM BENZENE

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