This document discusses the production and uses of halogenated aromatic compounds. It describes the chlorobenzene plant process which produces mono-chlorobenzene, para di-chlorobenzene, ortho di-chlorobenzene, and tri-chlorobenzene. It also discusses the distillation system and monochlorobenzene separator. Other halogenated aromatics discussed include fluorobenzene, bromobenzene, and iodobenzene along with their common uses.

1. Irfan Asyam
12/333536/TK/39886
Muhammad Falah S
12/333685/TK/40028
Zulfikar Pangestu
12/333834/TK/40176

2. Reaksi Aromatik
Halogen
Kegunaan
Aromatik Halogen
Pembuatan Skala
Laboraturium dan
Skala Industri

5. Diagram Energi

8. Alat
Necked Flask

9. Separatory
Funnel

10. Bahan
Benzene and Bromin Iron Powder

12. Chlorobenzene Plant
Mono-Chlorobenzene (MCB)
- 70 million Pounds/Year
Para di-Chlorobenzene (PDCB)
- 50 million Pounds/Year
Ortho di-Chlorobenzene (ODCB)
- 25 million Pounds/Year
Tri-Chlorobenzene (TCB)
- 18 million Pounds/Year

13. Main Plant
 Metachem products are manufactured
from two raw materials, chlorine and
benzene.
 Gaseous chlorine is sent by pipeline from
a neighboring plant, Occidental Chemical
Company (Oxy).
 The flow rate is controlled by a manual
control valve from the Main Control Room.
 The gaseous chlorine flow reaches the
chlorinator reactor.

14. Distillation System
 The material fed into the distillation system's
Columns, in order to recover the unreacted
benzene from the chlorinated benzene products
and to dry the fresh benzene together with the
recycled benzene.
 The reactor mass is fed into 901 Column where
the bottom stream of benzene free Chlorobenzene
are pumped into the next distillation column.
 From the 901 Column, the Chlorobenzene are
pumped into the Monochlorobenzene (MCB)
separator.

15. Monochlorobenzene
Separator
 The 220R Column is utilized to separate
Monochlorobenzene from the other
Chlorobenzene isomers.
 The overhead stream of this system is sent
to storage and consists of saleable
Monochlorobenzene.
 The bottom stream of the system consists of
Dichlorobenzene, Trichlorobenzenes and
Tetrachlorobenzenes, which is sent to the
other distillation columns for further processing.

16. Production
Dichlorobenzene
 The overhead stream from 857 Column consists of
97% pure PDCB, the remainder being 2% MDCB
and 1% ODCB is sent to the MWB Crystallizer
for further purification.
 The bottom stream from 856 Column that consists
of a mixture of ODCB with TCB's and a small amount
of Tetra's is sent to the 130R column for the
ODCB purification.
 The overhead stream-ODCB is sent to the
storage tank
 The bottom stream is sent to a holding tank as feed
for the Tri plant.

17. MWB
Crystalizer
 The MWB Crystallizer is a falling film crystallization
process that separates PDCB from a mixture
of PDCB, ODCB, and MDCB.
 There are two streams that leave this process,
the pure PDCB that is sent to a storage tank,
and the Eutectic steam, a mixture of MDCB,
and ODCB that is sent to an holding tank
for further processing

18. Fluorobenzene
 Fluorobenzene is used to
control carbon content in steel
manufacturing. It is an
intermediate for
pharmaceuticals, pesticides and
other organic compounds.

19. Mono Chlorobenzene
 Nitrochlorobenzene, 48 percent;
 Polysulfone polymers, 26
percent;
 Solvents in various formulations
and for processing isocyanates,
6 Percent
 Miscellaneous, 20 percent.

20. Ortho Dichlorobenzene
 Miscellaneous solvent uses
(paint removers, engine cleaners
and deinking solvents), 67
percent
 Toluene diisocyanate process
solvents, 33 percent

21. Para Dichlorobenzene
 Polyphenylene sulfide (PPS)
resin, 52 percent
 Room deodorants, 22 Percent
 Moth control, 15 percent
 Miscellaneous, including dye
and pesticide intermediate uses,
11 percent.

22. Bromobenzene
Bromobenzene dapat digunakan
untuk mempersiapkan reagen
yang sesuai pereaksi Grignard,
bromida phenylmagnesium . Ini
dapat digunakan, misalnya
dalam reaksi dengan karbon
dioksida untuk mempersiapkan
asam benzoat.
Bromobenzene digunakan
sebagai bahan dalam pembuatan
phencyclidine.

23. Iodobenzene
 Iodobenzene can react with
magnesium to form
the Grignard reagent,
phenylmagnesium iodide.
 Iodobenzene reacts with
chlorine to give the
complex, iodobenzene
dichloride, which is used as an
oxidant.