PCE2 UNIT-II-C4 and C5 Compounds

Unit-II
C4 & C5 Compounds
Introduction
 C4 olefins and their derivatives offer many potential applications for
manufacture of a large number of intermediates which are being used in
synthetic, plastics, stabilizers, plasticizers, solvents, gasoline additives,
antioxidants, herbicides, etc.,
 C5 hydrocarbons are used as feedstock for a wide variety of end
products such as chemical intermediates, thermoplastics, elastomers,
insecticides, pharmaceuticals, solvents, etc.,
 according to chem. systems, global demand for butadiene, isobutylene
and butene will climb 11.2, 18.8 and 1.7 million tones, respectively by
2010.
Product profile of C4 Olefins
Product profile of C5 Chemicals
Butadiene
Butadiene is produced commercially by three processes:
 Steam cracking of paraffinic hydrocarbons: in this process,
butadiene is a co-product in the manufacture of ethylene (the
ethylene co-product process).
 Catalytic Dehydrogenation of n-butane and n-butene (the
Houdary process).
 Oxidative dehydrogenation of n-butene (the oxo-d or o- x-d
process).
1. Steam Cracking of Paraffinic Hydrocarbons
Catalyst: Chromia-alumina 2. Catalytic Dehydrogenation of Butanes
Temp: 600-6700c (the Houdary process)
Pressure: 15-70 kPa
Space velocity: 1-3 hr-1
 In the Houdary process, n-butane is dehydrogenated over
chromium/alumina catalysts.
 The reactors normally operate at 12-15 centimeters Hg absolute
pressure and approximately 1100-1260 °F (600-680 °C).
 Three or more reactors can be used to simulate continuous
operation: while the first reactor is on-line, the second is being
regenerated, and the third is being purged prior to regeneration.
 Residence time for feed in the reactor is approximately 5-15
minutes. As the endothermic reaction proceeds, the temperature
of the catalyst bed decreases and a small amount of coke is
deposited.
 In the regeneration cycle, this coke is burned with preheated air,
which can supply essentially all of the heat required to bring the
reactor up to the desired reaction temperature.
 The reactor effluent goes directly to a quench tower, where it is
cooled. This stream is compressed before feeding an
absorber/stripper system, where a C4 concentrate is produced to
be fed to a butadiene extraction system for the recovery of high
purity butadiene.
Catalyst: Chromium/Iron
Temp: 620-6800c
Pressure: 0.15-0.18MPa 3. Catalytic Dehydrogenation of Butenes
Steam to Butane : 8-10:1
Space velocity: 1-3 hr-1
oxygen/butene molar
ratio of approximately 3. Oxidative dehydrogenation of n-butene (the oxo-d or o- x-d
0.55 process).
low pressure and
temperature
approximately 930-1110
°F (500-600 °C)
 In general, in an oxydehydrogenation process, a mixture of n-butenes, air and
steam is passed over a catalyst bed generally at lowpressure and approximately
930-1110 °F (500-600 °C).
 The heat from the exothermic reaction can be removed by circulating molten heat
transfer salt, or by using the stream externally for steam generation. An alternate
method is to add steam to the feed to act as a heat sink. The heat can then be
recovered from the reactor effluent.
 Reaction yields and selectives can range from 70-90%, making it unnecessary to
recover and recycle feedstock. (Yield losses can produce the CO2.)
 a mixture of air, steam, and n-butenes is passed over the dehydrogenation
catalyst in a continuous process.
 The air feed rate is such that an oxygen/butene molar ratio of approximately 0.55
is maintained, and the oxygen is totally consumed. A steam to butene ratio of
10:1 has been reported as necessary to absorb the heat of reaction and to limit
the temperature rise.
 The reactor effluent is cooled and the C4 components are recovered in an
absorber/degasser/stripper column combination.
 The lean oil flows from the bottom of the stripper back to the absorber, with a
small amount passing through a solvent purification area.
1- BUTENE
Processes:
1. 1-butene from C4 cut from FCC and steam crackers after recovery of butadiene.
2. Alpha butol process(selective dimerization of ethylene) – commercial process.
1-butene from C4 cut from FCC and steam crackers after

recovery of butadiene.
Sources: Butadiene free C4 fractions from steam cracking(27% butene) and FCC
cracker effluent (13%).
n- BUTENES
• 1-Butene and 2-Butene find applications in the manufacture
of sec-butanol, methyl ethyl ketone, acetic acid, maleic
anhydride and butadiene.
• 1- Butene finds application in the manufacture of polybutene
and butylene oxide
• 2-Butene can be made by isomerization of 1-butene
ISOBUTYLENE
Process:
1. Isobutene from C4 cut from FCC and steam cracker.
ISOBUTYLENE
Process:
2. Isobutene from C4 cut from FCC and steam cracker after
recovery of butadiene
Uses:
Isobutylene is used in the manufacture of tert-butyl alcohol;
methyl-tert-butyl alcohol, isobutylene oxide; 1,2-disobutylene
glycol; methacrylic acid; etc.,
C5 compounds
Cyclopentadiene and Dicyclopentadiene
• Cyclopentadiene and dicyclopentadiene are two
versatile chemical building blocks.
• Cyclopentadiene is used in the production of
premium white hydrocarbon resin which is used
hygiene applications.
• Dicyclopentadiene finds application in the
manufacture of unsaturated polyester resins –which
find application in non-reinforced and fibre
reinforced resins.
• Cyclopentadiene finds application in the manufacture
of ethylidiene norbornene-which is used in the
manufacture of ethylene propylene tert polymer.
Process Technology:
C5 stream of steam cracker represents the principle source
of cyclopentadiene and dicyclopentadiene.
Separation of cyclopentadiene and dicyclopentadiene first
involves the dimerization of C5 stream, which dimerizes
cyclopentadiene to dicyclopentadiene.
Dicyclopentadiene from the C5 stream is separated by
distillation.
The low purity dicyclopentadiene stream from distillation
column is first cracked to cyclopentadiene in the cracking
reactor and then fractionating the C5 components
Dicyclopentadiene Refining Process

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Unit-II

1-butene from C4 cut from FCC and steam crackers after

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