Benzene

Toluene

Xylene

AROMATIC S

OUTLINE
I. Definition
II. Aromatic Compounds
III.Production
A. Feedstock Consideration
B. Reforming Process
C. Solvent Extraction
IV. Important Intermediates
A. Ethylbenzene
B. Styrene
B. Cumene
C. Phenol

What is an Aromatic?
Also called arene (or sometimes aryl
hydrocarbon) is a hydrocarbon with
alternating double and single bonds between
carbon atoms forming rings.

The term was coined as such simply because

many of the compounds have a sweet or
pleasant odor

BENZENE (C6H6)
It is sometimes abbreviated PhH (PhenylHydrogen).
It is a colorless and highly flammable liquid
with a sweet smell.

It is an important component of gasoline,

comprising a few percent of its mass.

Most non-industrial applications have been

limited by benzene's carcinogenicity

BENZENE (C6H6)
STRUCTURES

TOLUENE (C7H8)
Also called methyl benzene and formerly
known as toluol
It is s clear, water-insoluble liquid with the
typical smell of paint thinners
Used as an industrial feedstock and as a
solvent

Also used as an inhalant drugs for its

intoxicating properties

XYLENE (C8H10)
Also called dimethyl benzene
(from Greek word xylo which means "wood")
Is an aromatic hydrocarbon consisting of
a benzene ring with two methyl substituents
Are major petrochemical, produced
by catalytic reforming and also by coal
carbonisation in the manufacture of coke
fuel.
xylenes are found in small quantities
in gasoline and airplane fuels

XYLENE (C8H10)

DERIVATIVES

AROMATIC PRODUCTION

FEEDSTOCK
Reformed naphtha

70%

Pygas by product
(from ethylene plant)

23%

Coal liquids

7%

AROMATIC PRODUCTION
7. Removal of
combustion gases

6. Removal of
sulphur
compounds

4. Separation of C1C4 hydrocarbons

5. Distillation to separate
C5-C6 HC from C7-C9
HC

3.Reactors for
cracking

2. isomerisation
reactors

1. A reactor in which the C6-C8

stream is being dehydrogenated
to BTX (reforming)

AROMATIC PRODUCTION

1. reforming reaction which

produces aromatic hydrocarbons
which takes place in reactor 1

REFORMING PROCESS
Operating Conditions
Older processes operate at 20 atmospheres
pressure, but modern plants run at a lower
pressure of 5 atmospheres and use continuous
catalyst regeneration. This means the catalyst is
withdrawn on a continuous basis and conveyed
through a regeneration system before being
returned to the reactor.

REFORMING PROCESS
During the reforming of naphtha, mainly

straight chain alkanes, with 6 - 8 carbon atoms,

are re-formed into molecules with the same
number

of

structures.

carbon

atoms

but

different

REFORMING PROCESS
CHEMICAL REACTIONS

REFORMING PROCESS
CHEMICAL REACTIONS

EXTRACTION OF
AROMATICS
A typical composition of BTX obtained by

reforming is benzene (15%), toluene (40%)

and xylene (45%)
Aromatic compounds
from

the

solvent

non-aromatic

extraction

are separated
compounds

(and

are

by

then

fractionally distilled into benzene, toluene

and xylene.

EXTRACTION OF
AROMATICS

INTERMEDIATES
1. Ethylbenzene (EB)
is a colorless aromatic liquid with a boiling
point of 136.2C,

The main process for producing EB is the

catalyzed alkylation of benzene with ethylene:

INTERMEDIATES
2. Styrene
also known as ethenylbenzene, vinylbenzene,
and phenylethene, is an organic compound

with the chemical formula C6H5CH=CH2

Styrene is the precursor to polystyrene and
several copolymers
Dehydrogenation: Ethylbenzene Styrene + Hydrogen

DERIVATIVE
2. Cumene
a liquid, is soluble in many organic solvents but
not in water,

The main process for producing cumene is a

synthetic route where benzene is alkylated with
propylene to isopropylbenzene.

DERIVATIVE
4. Phenol
is an aromatic organic compound with the
molecular formula C6H5OH
It is an important industrial commodity as a
precursor to many materials and useful
compounds. Its major uses involve its
conversion to plastics or related materials
Causticization: Benzyl chloride + NaOH sodium benzoate
Hydrolysis: Sodium benzoate + HCl (aq) Phenol + NaCl (aq)