Production of benzene

Introduction*
Benzene is an organic chemical compound with the molecular formula
.C6H6
Its molecule is composed of 6 carbon atoms joined in a ring, with one
hydrogen atom attached to each carbon atom. Because its molecules
contain only carbon and hydrogen atoms, and it is classed as a
.hydrocarbon
Benzene is a natural constituent of crude oil, and is one of the most
.elementary petrochemicals
Physical properties of benzene*
Property Numerical Value

Aniline point Co 30-<

API gravity ,15.56 Co 28.5

Boiling point, at 760 mmHg Co 80.099

color Colorless

Critical density kg/m3 304.4

Critical temperature Co 289.45

Crtical pressure kPa 4924.4

Density, at 25 C o
kg/m3 873.68

Calorific value (gross) at 25 C cal/gm 10102.4

Calorific value (net) at 25 C cal/gm 9698.4

,Flammability in air %vol 1.2-7.8

,Flash point (closed cup) Co 11-

Std enthalpy of combustion at 25 Co kJ/mol 3267.6

Std enthalpy of formation at 25 C o

Kj/mol 48.7

,Heat of fusion kJ/(kg .mol) 9847

Heat of vaporization at 80.1 Co kJ/(kg. mol) ,33871

,Ignition temperature in air Co 538

,Melting point Co 5.53

Molar mass 78.11

Refractive index 1.49792

Solubility in water 1.53g/L(0 Co) , 3.94g/L(100 Co)

Solubility of water in benzene at 25 Co g/100g benzene 0.05

Surface tension, at25 Co mN/m 28.18

Vapor pressure, at26.075 C o

kPa 13.33

Viscosity, at 20C o
cP 0.6468
 Chemical propertieses*
Substitution: Under suitable conditions, one or more of hydrogen- •
atoms of benzene can be replaced by atoms such as halogens, or by
groups such as nitro & sulfonic acid groups. Electrophilic substitution:
When a monosubstitution product of benzene is subjected to the
action of an electrophile, the rate of further substitution is increased
by some groups and decreased by some other groups. It also
.influence the direction of the second
 :Oxidation-

Oxidation: Benzene can be oxidized to a number of different •

products. An important reaction is the catalytic oxidation of benzene
to maleic anhydride and byproducts. The oxidation proceeds with air
or oxygen at elevated temperatures with a vanadium pentoxide and
.molybdenum oxide catalyst
 :Reduction-

Reduction: Benzene can be reduced to cyclohexane. At room •

temperature & ordinary pressure, benzene, either alone or in hexane
or cyclohexane solution, is quantitatively reduced with hydrogen
.using nickel catalyst
 :Pyrolysis-

Pyrolysis: When benzene is passed through a red-hot iron tube, •

bubbled through molten lead or pumice, or passed at elevated
temperatures over vanadium compounds, condensation takes place
with the formation of biphenyl. At temperatures above 750 Co,
benzene decomposes largely into carbon & hydrogen
 :Halogenation-

Depending on the conditions, either substitution or addition products

can be obtained by the halogenation of benzene. Chlorine or bromine
reacts with hot benzene in the presence of carriers such as ferric
halides to give substitution products such as chlorobenzene or
. bromobenzene
 :Nitration-

The nitration of benzene to a monoderivative occurs readily in yields as

high as 98% when a mixture of concentrated nitric and sulfuric acids is
.used at 50-55 Co

Sulfonation: Benzene can be sulfonated with concentrated or fuming •

.sulfuric acid to benzenesulfonic acid
 :Alkylation-

Alkylation: Alkylbenzenes, such as ethylbenzene & cumene, are •

produced commercially by the reaction of benzene with ethylene &
propylene in the liquid or vapor phase in presence of anhydrous
.aluminium chloride or solid phosphoric acid as the catalyst
 Uses of Benzene*

. Manufacturing of Insecticides-
.Manufacturing of Nitrobenzene, chlorobenzene -
. Manufacturing of dyes, drugs , plastics-
. Manufacturing of sulphonic acid, styrene-
. Manufacturing of motor fuel ( when mixed with petrol ) -
.Use as a solvent also as a base material for making medicines -
Benzene is used primarily as a solvent in the chemical and pharmaceutical
industries, as a starting material and intermediate in the synthesis of numerous
.chemicals, and in gasoline
 Raw Material for Toluene*
hydrodealkylation
Toluene : (C6H5CH3) is a noncorrosive, volatile liquid with an aromatic odour. Its
solubility in water is 535 mg/litre. The odour threshold varies considerably; a
.geometric mean of 11 ppm has been estimated from published data

: Hydrogen
Hydrogen is the lightest and most abundant of all elements. About 90 % of all atoms in
the universe are hydrogen . In normal temperatures, hydrogen is a colorless and
odorless flammable gas . Energy content per kilogram of hydrogen is three times larger
than for gasoline. However, energy content per volume is low, due to low density of
. gaseous state .Hydrogen burns cleanly - The product of combustion is pure water
 Manufacturing Process*

The major processes for producing benzene include:

-Catalytic reforming.
.Toluene Hydrodealkylation-
.Toluene disproportionation-
.Pyrolysis gasoline-
.Production from coal tar-
 Reaction & Thermodynamic*

Catalytic Reforming-1

.hexane, C6H14 loses hydrogen and turns into benzene-

:methylbenzene (toluene) is made from heptane-

 Toluene Hydrodealkylation-2
Hydrodealkylation of aromatics, usually toluene, is used though heavier
:aromatics are used as well. The reaction that takes place is as follows
C6H5CH3 + H2 ------------> C6H6 +CH4

:The reaction with more alkylated benzenes is

C6H4(CH3)2 + H2 --------------> C6H5CH3 --------------> C6H6 +CH4
 PG purge
compressor
RG .yH2

95% H2 H2 120 90 f

FG C1 177 product

tol uene col umn

Cool er

Benzene column
stabilizer
fuel benzene Ff S

FF 1150 F 500 psi 150 psia

Feed- effl uent furnace reactor
Heat exchanger
Toluene T2=625 FO FT

1150 f Quench

511 f 445 f 358 f 267 f 120 f 90 f

571 505 418 327 cool er 100

cool er cool er cooler cooler flash
100 f
450 ps i
Toluene disproportionation-3
 Pyrolysis gasoline-4

Pyrolysis gasoline is the by-product of steam cracking of paraffin gases, naphthas,

gas oils and other hyrdrocarbons used to make ethylene. Pyrolysis gasoline can
contain up to and including 5% diolefins. This makes the compound unstable. It
.also contains 60% aromatics, 50% of which is benzene
Benzene is extracted through solvent extraction and then distillation. This process
makes up 30-35% of the world's benzene production. The benzene extraction from
:pyrolysis gasoline is carried out in the following steps
. Hydro-treating-
.Secondary Hydrogenation-
.Solvent Extraction-
Fractionation-
 Effects of benzene*

:Toxic effects-
. benzene can cause aplastic anaemia
: Observations in humans-
.Benzene vapor is irritating to the respiratory tract
benzene is also irritating to skin.. Following acute inhalation of high levels of
.benzene
:Inhalation-
Mouse: Anemia, lymphocytopenia and bone-marrow hypoplasia were found
in 50 male AKR/J mice, 6 weeks of age at the start of the study, which were
.exposed to 300
 The pollution treatment ways*

.Applied a limited strategy to minimize the harmful to the lowest limits-

.Building the plant far away from the housing places-
Applied a strict system to save and transport products and raw Materials to-
.minimize health and environment harmful
Know the equipment's efficiency in the plant and know the rate of Harmful-
.materials release from the plant
Making a checkup for workers and the area population periodical to Know if there-
.is any diseases
.Evaluate the dangerous to try to minimize it by safer way-
 Production of benzene
: Students names
Ahmed Al-hashemi
Mohammed bawazier
Saeed bashnini
Ahmed bagubair
Mohammed alkatheri
Abdullah benlahoul
Yamany balhage
 :Introduction*
Benzene is an organic chemical compound with
.the molecular formula C6H6
Its molecule is composed of 6 carbon atoms Raw material*
joined in a ring, with one hydrogen atom
attached to each carbon atom. Because its Toluene-
molecules contain only carbon and hydrogen
.atoms, and it is classed as a hydrocarbon
Hydrogen-
Benzene is a natural constituent of crude oil, and
.is one of the most elementary petrochemicals

Uses of Benzene*
. Manufacturing of Insecticides-
.Manufacturing of Nitrobenzene, chlorobenzene- *Methods and process
. Manufacturing of dyes, drugs , plastics-
-Catalytic reforming.
. Manufacturing of sulphonic acid, styrene-
Manufacturing of motor fuel ( when mixed with petrol- .Toluene Hydrodealkylation-
Use as a solvent also as a base material for making- .Toluene disproportionation-
.medicines .Pyrolysis gasoline-
Benzene is used primarily as a solvent in the chemical-
and pharmaceutical industries, as a starting material .Production from coal tar-
and intermediate in the synthesis of numerous
.chemicals, and in gasoline
Reaction & Thermodynamic* :Toxic effects-
: Catalytic Reforming-1
. benzene can cause aplastic anaemia
:hexane, C6H14 loses hydrogen and turns into benzene- : Observations in humans-
.Benzene vapor is irritating to the respiratory tract
benzene is also irritating to skin.. Following acute
.inhalation of high levels of benzene
:Inhalation-
:methylbenzene (toluene) is made from heptane- Mouse: Anemia, lymphocytopenia and bone-
marrow hypoplasia were found in 50 male AKR/J
mice, 6 weeks of age at the start of the study,
.which were exposed to 300

:Toluene Hydrodealkylation-2
Hydrodealkylation of aromatics, usually toluene, is used though heavier
:aromatics are used as well. The reaction that takes place is as follows
C6H5CH3 + H2 ------------> C6H6 +CH4
The pollution treatment ways*
Applied a limited strategy to minimize the harmful to the -
:The reaction with more alkylated benzenes is .lowest limits
.Building the plant far away from the housing places -
C6H4(CH3)2 + H2 --------------> C6H5CH3 --------------> C6H6 +CH4 Applied a strict system to save and transport products and -
.raw Materials to minimize health and environment harmful
: Toluene disproportionation-3 Know the equipment's efficiency in the plant and know -
Alkylated aromatics are transalkylated to produce benzene and alkylated .the rate of Harmful materials release from the plant
Making a checkup for workers and the area population -
benzenes. An example of such a method is the Tatoray process. In this .periodical to Know if there is any diseases
process, toluene and C9 aromatics are converted to benzene and xylen .Evaluate the dangerous to try to minimize it by safer way -
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