School of Chemical and Biomedical Engineering

CH4220 Special Topics in Green Chemistry and Engineering/ Yoel Sasson

Assignment No. 1
August 28
th
2014. To be submitted by September 5
th
2014



[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
6
H
5
Cl, 2.5 wt% C
6
H
4
Cl
2
and 0.5 wt% C
6
H
3
Cl
3
. The gas
output contains only HCl.
[a] Write down stoichiometric equations for the reactions taking place in this process .
[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.


[2] The following is a laboratory procedure for the synthesis of a pharmaceutical intermediate p-
nitrobenzyl 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.
[b] Explain the need to maintain the reaction temperature below 20
0
C and how this is actually done.
[c] Draw a flow sheet of the (batch) process based on one ton of product and confirm the mass
balance. Make reasonable assumptions for the fate of materials not accounted for in the
procedure.
[d] 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.
[e] Comment about the environmental impact of this process. How could this process be improved
from the environmental perspective?