Chlorobenzene, an important solvent and intermediate in the production of many o
ID: 518836 • Letter: C
Question
Chlorobenzene, an important solvent and intermediate in the production of many other chemicals, 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 dichlorbenzene, and in a third reaction the dichlorobenze is chlorinated to trichlorbenzene. The feed to the reactor consists of pure benzene and chlorine. The liquid output from the reactor contains the product, chlorobenzene, the byproducts dichlorbenzene and trichlorbenzene, and unreacted benzene. In order to determine the yield of the reaction you will use GC chromatography. A known calibration is run and the following data is collected by the flame ionization detector.
Compound
Weight %
Area
Chlorobenzene
Dichlorbenzene
Trichlorbenze
Benzene
40
10
1
49
650
187
20
723
When you test the liquid output from the reactor in the GC you collect the following data. Determine the concentration of the components (in weight percent) in the reactor stream. (20 points)
Compound
Area
Chlorobenzene
Dichlorbenzene
Trichlorbenze
Benzene
698
63
14
1287
Compound
Weight %
Area
Chlorobenzene
Dichlorbenzene
Trichlorbenze
Benzene
40
10
1
49
650
187
20
723
Explanation / Answer
IT IS CLEARLY GIVEN IN THE PROBLEM, THAT
THE REACTION BETWEEN BENZENE AND
CHLORINE IS DONE WITH A KNOWN CALIBRATION.
THE STEP-BY-STEP REACTIONS ARE
C6H6 + Cl2 = C6H5Cl +HCl
C6H5Cl+ Cl2 = C6H4Cl2+HCl
C6H4Cl2 + Cl2 = C6H3Cl3+HCl
IN THE FIRST STEP CHLOROBENZENE C6H5Cl IS PREPARED.
IN THE SECOND STEP DICHLOROBENZENE C6H4Cl2 IS PREPARED.
IN THE THIRD STEP TRICHLOROBENZENE C6H3Cl3 IS PREPARED.
AND AT THE END, A PORTION OF BENZENE IS LEFT OVER.
Compound
Weight %
Area
Chlorobenzene
Dichlorbenzene
Trichlorbenze
Benzene
40
10
1
49
650
187
20
723
Compound
Area
Weight %
Chlorobenzene
Dichlorbenzene
Trichlorbenze
Benzene
698
63
14
1287
44.55
00.35
00.75
64.35
Compound
Weight %
Area
Chlorobenzene
Dichlorbenzene
Trichlorbenze
Benzene
40
10
1
49
650
187
20
723
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