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UNIT-VIII

SYNTHETIC FIBERS

Introduction
Synthetic fibers are the indirect consequence of

a spectacular growth in petrochemical industry.


The demand is one of the three basic needs of
mankind-Food, cloth and shelter.
Real driving force for the development of
synthetic fibre industry have been due to the
availability of feed stock from petroleum and
petrochemical industry.
The synthetic fiber industry based on comprises
of polyamides, polyester, acrylics and
polypropylene fibers and enjoy a major share in
international business and marketing.

1929 polyamides were first discovered by W.H.Carothers.


1941- polyester fibers are invented and commercial

production started in 1951.


1954- reported the synthesis of acrylonitrile &
polyacrylonitrile.
Polyamides are Nylon 6 & Nylon 66, about 85-90% of the
total nylon produced which find application in synthetic
fiber and Nylon tyre yarn ( Continuous strand of twisted
thread of natural or synthetic fibers). Because of high
Melting point, nylon 66 is proffered over nylon 6 where
high temperature performance is required.
Some of the other Nylons are Nylon 4,6; nylon 6,9; nylon
6,12; nylon 11,; nylon 12,; nylon 12,12,; nylon 13,13;.
Nylons are exception all strong elastic, abrasion, resistance
and easy to wash resistant to damage from oil and many
chemicals, low in moisture absorbency.

Nylon 6 is the first synthetic fiber introduced in

India.
The installed capacity production of the nylon is
36000 & 76000 tones and 43000 & 86000
tones in 2010- 2011 respectively in India.

Classification of Fibre

Major synthetic fibres and their characteristics

Synthetic Fibres
Cyclohexane
Caprolactum
Adipic acid
Adiponitrile
Hexamethylene Diamine
Terephthalic acid & Dimethyl terephthalate
Acrylonitrile
Polyethylene terephthalate
Nylon 66
Nylon 6

CYCLOHEXANE C6H12
Cyclohexane is an important chemical

intermediate derived from benzene.


It is used for the manufacture of
Caprolactam,;
Adipic acid &Hexamethylene diamine used
for manufacture of Nylon 66; and
Caprolactam used for the manufacture of
Nylon 6.
Major portion of 90% of the Cyclohexane is
used in the manufacture of nylon fiber and
nylon molding resin and remaining 10% of
Cyclohexane ends up as solvents or in

Cyclohexane is made by catalytic hydrogenation of

benzene in liquid phase or the vapor phase.


UOP (universal oil products) hydrogenation process
use a liquid phase hydrogenation of benzene at 200 to
3000C in presence of platinum based catalyst
promoted by lithium salt at 3 Mpa.

IFP (Institut Francais du Petrole) process Cyclohexane

is produced by liquid phase hydrogenation of benzene


at 160-2000C and 4 MPa using Raney nickel catalyst.
Only the difference is the in the catalyst and the
temperature, slower lower temperature required and
this is the reaction that is taking place.

yclohexane from liquid phase hydrogenation of benze

This is the process flow diagram for the

manufacture of Cyclohexane, by the benzene.


Benzene that is going to the hydrogenation
tower and the from the hydrogenation tower the
product that is going to the high press. And from
the high press the hydrogen that is recycled to
the system and make up hydrogen, that is adjust
there and so the
offshore separation, it is going to the plus low
pressure. And from the low pressure again, the
light products that we are getting and then this
finally, we are getting the Cyclohexane from the
bottom of this flash low.

Caprolactam
Caprolactam is the principle raw material for nylon 6,.
It is a versatile material used as fibers, industrial yarns, and

flooring covering as well as for engineering plastics.


Global Caprolactam production and demand:

The major Caprolactam produced in India mainly GSFC (Vadodara)

& FACT (Travancore) .


I. Steps in the manufacture of Caprolactam from
Cyclohexane:
Process of manufacturing Caprolactam involves three basic steps.
Manufacture of Cyclohexanone
Manufacture of Hydroxylamine Sulphate
Manufacture of Caprolactam

1. Manufacture of cyclohexanone:
Cyclohexane is first prepared from benzene by
hydrogenation in a tubular reactor containing Ni
catalyst at 120-1800C & 10 atm.
Here benzene should be sulphur free to avoid
poisoning of the catalyst. For this purpose
desulphurization process is used.
Next, Cyclohexane is oxidized in a multi
compartment reactor at a temperature of 158-1600C
& 10 atm where the liquid flows in series from one
chamber to another using cobalt salt as catalyst.
The product stream is treated with NaOH to
neutralize acids, saopnify esters and to decompose
peroxides.
Sodium salts which are immiscible with the main
product stream are separated in a gravity settler.

The organic phase containing cyclohexane,

cyclohexanol, cyclohexanone is fed to a series of


three distillation columns where these are
separated.
Cyclohexane is separated as top product from
the last column.
Cyclohexanol is separated in the last column as
bottom product and is dehydrogenated to
cyclohexanone in the presence of zinc carbonate
and calcium carbonate catalysts at 4000C.
The unconverted cyclohexanol and
cyclohexanone after removal of light ends is
recycled to the third column for recovery of
cyclohexane.

2. Manufacture of Hydroxylamine sulphate:


Production of hydroxylamine sulphate involve:
I. Production of ammonium carbonate by absorption
of CO2 in 24% of aqueous ammonium solution.
II. Production of nitrous oxide from the mixture of NO
& NO2, which is produced by combustion of
ammonia in the presence of Pt-Rh catalyst at 850C.
III. Absorption of nitrous gases from the combustion of
ammonia in ammonium carbonate to yield
ammonium nitrite.
IV. Reacting SO2 with ammonium nitrite and
ammonium carbonate which results in the
production of hydroxylamine disulphonate and
V. Finally, hydrolysis of hydroxylamine disulphonate at
950C to yield hydroxylamine sulphate and
ammonium sulphate as a byproduct.

3. Manufacture of Caprolactum:
The first step in the manufacture of caprolactum

is the production of cyclohexanone oxime by


reacting cyclohexanone with hydroxylamine
sulphate in a multi-compartment reactor.
The Beckmann rearrangement of oxime to
caprolactum is carried out in the presence of
oleum at a temperature in the range of 75-80 0C
which is neutralized by ammonia.
During this process ammonium sulphate is
formed as a byproduct.
Caprolactum and ammonium sulphate are
passed through a series of extractors where
toluene is used as solvent.

Ammonium sulphate collected from the

extractor bottom is purified, crystallized


centrifuged and dried.
Caprolactum solution is concentrated in
multi effect evaporators and finally
purified.

Flow diagram for caprolactum from


Cyclohexanone

II. Caprolactum from Toluene


route:
Manufacture of caprolactum by the SINA
process using toluene as a raw material
involves three basic steps
Oxidation of toluene to benzoic acid
Hydrogenation of benzoic acid to
hexahydrobenzoic acid
Conversion of hexahydrobenzoic acid to
caprolactum.
Toluene is first converted to benzoic acid by
oxidation with air in the liquid phase at 1601700C & 8-10 atm using Cobalt salt as
catalyst.

The liquid stream is distilled to yield benzoic

acid in the vapour phase.


In the second step, hydrogenation of benzoic
acid to hexahydrobenzoic acid is performed in
the series of stirred reactors in the liquid
phase, in the presence of palladium catalyst at
1700C & 10-17 atm.
Unconverted hydrogen is recycled after
scrubbing with caustic soda.
Water catalyst are recovered as slurry by
centrifuging the liquid stream and recycling it.
The clean product is flash distilled under
vacuum.

In the next step, caprolactum is obtained by

reacting hexahydrobenzoic acid and nitrosyl


sulphuric acid in the presence of oleum.
Nitrosyl sulphuric acid (HNOSO4) is prepared
from ammonia by catalytic oxidation with air
in Pt-Rh followed by absorbing N2O3 gases in
oleum.

Various Routes for Caprolactam production

Various Routes for Caprolactam


production

Various Routes for Caprolactum


production

Adipic acid
It is the basic raw material for the manufacture of Nylon

66.
Nylon 66 is manufactured by the condensation
polymerization of adipic acid and Hexamethylene diamine.
due to its superior high temperature strength.
Overall global demand for adipic acid grew by 3.6% during
2000-10.
Nylon 66 is the major consumer of adipic acid.
It is mainly used in the manufacture of polyurethane,
plasticizers, unsaturated resins etc.,

Various routes for Adipic acid


manufacture

Process technology:
Cyclohexane is oxidized by air to form
cyclohexanol &cyclohexanone in presence of
cobalt naphthenate catalyst at temperature of
145-1500C.
The cyclohexanol and cyclohexanone mixture
is oxidized to adipic acid in presence of nitric
acid using ammonium metavanadate and
copper scrap at 60-800C.
The adipic acid formed is crystallized,
centrifuged and finally dried with hot air.

Manufacture of Adipic acid by two step oxidation process

Various routes for Adipic acid manufacture

Hexamethylene Diamine
Hexamethylene diamine is another intermediate for

the manufacture of Nylon 66.


Hexamethylene diamine is manufactured by the
catalytic hydrogenation of Adiponitrile.
Adiponitrile is manufactured using acrylonitrile,
butadiene or adipic acid.
Hexamethylene diamine by Hydrogenation of
Adiponitrile:
Hexamethylene diamine is manufactured by
catalytic hydrogenation of Adiponitrile in presence of
catalyst either by high pressure process (60-65 MPa)
or low pressure process (3 MPa).
Catalyst in low pressure is nickel whereas in case of
high pressure process it is cobalt and copper.

Manufacture of Hexamethylene Diamine

ADIPONITRILE (NC-(CH2)4-CN)
It is used for manufacture of Hexamethylene Diamine.

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