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Module Code: CH4220 (Assignment #1)

Division of Chemical & Biomolecular Engineering

Assignment No. 1
1. Chlorobenzene is an important solvent and intermediate in the production of numerous
chemicals. It is produced by bubbling chlorine gas through liquid benzene in the presence of
ferric chloride catalyst. In an undesired side reaction the product is further chlorinated to
dichlorobenzene and in a third reaction the dichlorobenzene is chlorinated to
trichlorobenzene.
The feed to a chlorination reactor consist of pure benzene and chlorine. The liquid output
from the reactor contains 65 wt% benzene, 32 wt% C 6H5Cl, 2.5 wt% C6H4Cl2 and 0.5 wt%
C6H3Cl3. The gas output contains only HCl.
[a] Write down stoichiometric equations for the reactions taking place in this process.
C6 H 6 Cl2 FeCl
3 C6 H 5Cl HCl
C 6 H 5 Cl Cl2 C6 H 4 Cl 2 HCl
C6 H 4 Cl2 Cl2 C 6 H 3Cl3 HCl

[b] Determine: the E-factor (assume benzene can be recycled), conversion of benzene, yield of
chlorobenzene and selectivity to the desired product vs. all undesired products.
E-Factor = 0.09375
Conversion of benzene = 0.2674
Yield of Chlorobenzene = 0.935
Selectivity = 14.389

CBE Year 4/Academic Year 2014/2015

School of Chemical & Biomedical Engineering

Copyright Nanyang Technological University. All rights reserved.

Module Code: CH4220 (Assignment #1)

Division of Chemical & Biomolecular Engineering

2. The following is a laboratory procedure for the synthesis of a pharmaceutical intermediate pnitrobenzyl cayanide. You were assigned to lead a team of engineers for the scale up of this
procedure into an industrial operation.
[a] Write down a balanced equation(s) for the process and calculate the atom yield.
C8 H 7 N HNO3 H 2 SO
4 p C8 H 6 N 2 O2 H 2 O
C8 H 7 N HNO3 H 2 SO
4 o C 8 H 6 N 2 O2 H 2 O

Atom Yield =

162
100%
117 63

= 90%

[b] Calculate the Mass Intensity, the Mass Productivity and the E-factor of this process. Try to
assess the Environmental Index (in and out) of the process.
Mass Intensity (MI)

= 30.266 t/t

Mass Productivity = 3.304%

E - Factor = 34.897
Assume Qinput and Qoutput as 5.

EI in
EI out

=151.33 PEI/ kg
= 174.485 PEI/kg

CBE Year 4/Academic Year 2014/2015

School of Chemical & Biomedical Engineering

Copyright Nanyang Technological University. All rights reserved.