Toluene Toluene Toluene Hydrogen Chromium Platinum

1.
0 Introduction
In this chapter, the raw materials for the production of cumene is discussed
which are benzene and propylene. The properties and the applications of the
product formed which is cumene is also discussed in this section.
1.1 Benzene
Benzene is an organic compound with a chemical formula of C6H6 and is
classified as a hydrocarbon. Benzene is a clear, colourless, volatile and highly flammable,
liquid aromatic hydrocarbon that has a gasoline-like odour. This compound can be found
in crude oils, by product of coal distillation and as a by-product of oil-refining processes.
In industry benzene is used as a solvent for fats, resins, waxes, oils, inks, paints,
plastics, and rubber, and is used in the synthesis of numerous chemicals. It is also a
constituent in motor fuel, aid in the extraction of oils from seeds and nuts as well as in
photogravure printing. It is also used. Benzene is also used as a chemical intermediate
and in the manufacture of detergents, explosives, pharmaceuticals, and dyestuffs.
Figure 1.1 Structure of Benzene (Qalm, 2017)
Benzene is produced from the process of hydrodemethylation of toluene under
either catalytic or thermal conditions. In catalytic toluene hydrodealkylation, toluene is
first mixed with a hydrogen stream which is then passed through a vessel that is packed
with a catalyst of supported chromium or molybdenum oxides, platinum or platinum
oxides, on silica or alumina. The operating temperatures has a range from 500 to 595 C
and pressures are between 4-6 MPa (40-60 atm). This reaction is highly exothermic and
injection of quench hydrogen is placed at several places along the reaction to control the
temperature. Conversions per pass usually reach 90% and selectivity to benzene is often
more than 95%. This process occurs at lower temperatures and offers wide selectivity
but requires continuous regeneration of the catalyst. Products leaving the reactor pass
through a separator to remove unreacted hydrogen which is recycled to the feed. Further
fractionation is done to separate methane from the benzene product.
1.2 Propylene
Propylene is an unsaturated organic compound with a single double bond having a
chemical formula of C3H6. It is a colourless gas at room temperature with a naturally
pungent smell. Although similar to propane, it has a double bond which gives it a
combustion advantage and is extremely flammable and non-toxic. Propylene is an
alternative to propane for heating and cutting due to its combustion advantage and is
widely used as a fuel gas for high-velocity oxygen fuel (HVOF) processes. Moreover, the
chemical and plastics industries depends on propylene as a fuel gas. Other applications
include organic synthesis to produce materials such as phenol and acetone. Propylene
can be polymerised to form polypropylene plastic and be employed as a refrigerant, or in
calibration mixtures. In addition, it can be used to test the efficiency of gas burners and
engines. (The Linde Group, 2017)
Propylene can be obtained during the refining of gasoline and it can also be produced by
splitting, cracking and reforming hydrocarbon mixtures. According to ICIS (2007), there
are two sources of propylene which are as a byproduct from the steam cracking of liquid
feedstocks such as naphtha as well as LPGs, and from refineries using off-gases
produced in fluid catalytic cracking (FCC) units. The remainder of propylene is produced
using on-purpose technologies. For example, propane dehydrogenation (PDH) and
metathesis.
Figure 1.2 Structure of Propylene (CIEC, 2014)
1.3 Cumene
Cumene is the common name for isopropylbenzene, an organic compound that is
an aromatic hydrocarbon. It has a chemical formula of C 9H12. It is a constituent of crude
oil and refined fuels. Almost all cumene are produced as a pure compound on an
industrial scale is then converted to cumene hydroperoxide, which is used as an
intermediate in the synthesis of other industrially important chemicals such as phenol
and acetone. Cumene is produced from benzene and propylene in Friedel-Craft
Alkylation of benzene by propylene. (PubChem, 2017)
Figure 1.3 Structure of Cumene (Royal Society of Chemistry, 2015)

Cumene is a clear, colourless, flammable liquid with an aromatic odor. Cumene is less
dense than water and the vapors heavier than air. It may be toxic by inhalation,
ingestion and skin absorption. (PubChem, 2017).
Property Value
Molecular Weight 120.195 g/mol
Boiling Point 152C
Melting Point -96C
Flash Point 31C
Specific gravity at 20 C 0.862
Solubility at 25 C in water 61.3mg/L
Vapor Density relative to air 1:4.2
Vapor Pressure at 25 C 4.55 mmHg
Stability Volatile
Auto-Ignition Temperature 420C
Viscosity at 25C 0.737mPa.sec
Heat of Vaporisation at 25C 45.13kJ/mol
Table 1.1 Physical Properties of Cumene (PubChem, 2017)
Cumene is produced mainly for phenol and acetone production. However, it can also be
used as a blending component in gasoline pool, as a method to avoid benzene restrictions
in gasoline. It can be said that the use of cumene as a blending component will rise when
its price falls below its alternate octane value. (IHS Markit, 2016)
IHS Markit( 2016), Cumene, Available at:https://www.ihs.com/products/cumene-
chemical-economics-handbook.html Accessed on 25 February 2016
QALM (217), Benzene, Available at: http://qalm.weebly.com/benzene-molecule.html
Accessed on 26 February 2017
CIEC (2014), Poly(Propene) Poly(Propylene) , Available at:
http://www.essentialchemicalindustry.org/polymers/polypropene.html Accessed on: 26
February 2017
ICIS (2007), Propylene Production and Manufacturing Process, Available at:
https://www.icis.com/resources/news/2007/11/06/9076456/propylene-production-and-
manufacturing-process/ Accessed on 26 February 2017
Royal Society of Chemistry (2015), Cumene, Available at:
http://www.chemspider.com/Chemical-Structure.7128.html Accessed on 26 February
2017
PubChem (2017), Benzene, Available at:
https://pubchem.ncbi.nlm.nih.gov/compound/benzene#section=Physical-Description
Accessed on: 25 February 2017
PubChem (2017), Cumene, Available at:
https://pubchem.ncbi.nlm.nih.gov/compound/cumene#section=3D-Conformer Accessed
on: 25 February 2017

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1.

product formed which is cumene is also discussed in this section.

Benzene is an organic compound with a chemical formula of C6H6 and is

classified as a hydrocarbon. Benzene is a clear, colourless, volatile and highly flammable,

in crude oils, by product of coal distillation and as a by-product of oil-refining processes.

photogravure printing. It is also used. Benzene is also used as a chemical intermediate

and in the manufacture of detergents, explosives, pharmaceuticals, and dyestuffs.

Figure 1.1 Structure of Benzene (Qalm, 2017)

Benzene is produced from the process of hydrodemethylation of toluene under

either catalytic or thermal conditions. In catalytic toluene hydrodealkylation, toluene is

with a catalyst of supported chromium or molybdenum oxides, platinum or platinum

fractionation is done to separate methane from the benzene product.

Propylene is an unsaturated organic compound with a single double bond having a

chemical formula of C3H6. It is a colourless gas at room temperature with a naturally

combustion advantage and is extremely flammable and non-toxic. Propylene is an

can be polymerised to form polypropylene plastic and be employed as a refrigerant, or in

engines. (The Linde Group, 2017)

using on-purpose technologies. For example, propane dehydrogenation (PDH) and

Cumene is the common name for isopropylbenzene, an organic compound that is

an aromatic hydrocarbon. It has a chemical formula of C 9H12. It is a constituent of crude

industrial scale is then converted to cumene hydroperoxide, which is used as an

intermediate in the synthesis of other industrially important chemicals such as phenol

and acetone. Cumene is produced from benzene and propylene in Friedel-Craft

Alkylation of benzene by propylene. (PubChem, 2017)

Figure 1.3 Structure of Cumene (Royal Society of Chemistry, 2015)

ingestion and skin absorption. (PubChem, 2017).

used as a blending component in gasoline pool, as a method to avoid benzene restrictions

chemical-economics-handbook.html Accessed on 25 February 2016

QALM (217), Benzene, Available at: http://qalm.weebly.com/benzene-molecule.html

Accessed on 26 February 2017

CIEC (2014), Poly(Propene) Poly(Propylene) , Available at:

http://www.essentialchemicalindustry.org/polymers/polypropene.html Accessed on: 26

ICIS (2007), Propylene Production and Manufacturing Process, Available at:

manufacturing-process/ Accessed on 26 February 2017

Royal Society of Chemistry (2015), Cumene, Available at:

http://www.chemspider.com/Chemical-Structure.7128.html Accessed on 26 February

Accessed on: 25 February 2017

PubChem (2017), Cumene, Available at:

on: 25 February 2017

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