BUTADIENE

G RO U P M E M B E R S :
• MUHAMMAD AIMAN (2015636834)
• N U R NA B I L A A K M A L ( 2 0 1 5 8 3 7 3 3 4 )
• P U T R I A N I NA R I S A ( 2 0 1 5 6 3 6 8 5 6 )

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 !
1,3-Butadiene
1,2-Butadiene
Gasoline
like odor
BUTADIENE
Monomer Soluble
Colorless Gas in Water
 !
E. Caventou Russian chemist,
isolated a
1863 previously 1910 Sergei Lebedev
polymerized
unknown butadiene and
hydrocarbon from obtained a material
the pyrolysis of with rubber-like
amyl alcohol. properties.

This hydrocarbon Eduard Tschunker &

was identified as Walter Bock, made a
butadiene by copolymer of styrene
Henry Edward and butadiene that
Armstrong. could be used in
1886 1929 automobile tires.
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REACTION MECHANISM !

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1. Oxidative Dehydrogenation of
Propylene
(Raw material producing product)

C3H6  C4H8 + C2H4 + C5H10 + C6H12

C4H8 (2-butene) + 0.5 O2  C4H6 (1,3-butadiene) + H2O

• Catalyst used is SiO2

• Modern catalyst (Multi-metal oxide catalyst)

• Highly exothermic reaction

• N-methyl-pyrrolidone (NMP) as solvent
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1. Oxidative dehydrogenation of
propylene

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 Metathesis of propylene to 2-butane
Mechanism

2(C3H6)  C4H8 + C2H4

- Side reaction

• Products: cis-2-butane & trans-2- 2-Butene  1-Butene

(isomerization)
butane
• By-products: 1-butene, pentene & 2(1-Butene)  C2H4 + C6H12
hexane
C3H6 + 1-Butene  C2H4 + 8
 Distillation
• Ethylene will be separated and sold
off at an industry

• Propylene will be recovered in the

distillate and recycled back into the
metathesis feed

• The butene products will be separated

Butene Recovery from the side products (C5 & C6), to
undergo the oxidative
dehydrogenation
 Oxidative
Dehydrogenation
• Shell & Tube PBR
• Multi-Metal Oxide Catalyst
• Highly Exothermic
Extractive
Distillation
• The high-purity 1,3-butadiene that
this system will be producing requires
higher purity of butadiene.
• N-methylpyrrolidone (NMP) act as a
solvent to remove 1,3 butadiene from
the remaining C4’s
 2. Steam Cracking of Paraffinic
Hydrocarbon
• Main product is ethylene, butadiene as co-product with 4.3%
production.
• The steam is a homogenous catalyst in steam cracking that inhibits
coke formation and thus allows the cracker to operate at the high
temperatures that ensure high selectivity to light olefins without
excessive coke formation.
• Steam cracking involves diluting saturated hydrocarbons with steam
and heating up to high temperatures in the absence of oxygen to
produce smaller hydrocarbons and unsaturated olefins.
 2. Steam Cracking of Paraffinic
Hydrocarbon
• Very high reaction temperature.
• Parameters such as temperature, pressure, and residence time all
have effects on the cracking reaction.
• For the conventional steam cracking process, ethylene yields are
improved by raising the cracking temperature and reducing
residence time, i.e., increasing the cracking severity.
• The residence time is reduced to milliseconds to improve yield (to
avoid undesirable over cracking – formation of coke), resulting in
gas velocities faster than the speed of sound.
Steam Cracking of Paraffinic Hydrocarbon

Mechanism
C2H6 C2H4 + H2

2(C2H6)  C3H8 + CH4

C3H6 C2H2 + CH4

C2H2 + C2H4  C4H6

C2H4 + C2H6  C3H6 + CH4

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Steam Cracking of Paraffinic Hydrocarbon
16
 Process
1. Hydrocarbon feed heated with steam to 1050 OC and fed to Cr-Ni reactor
tube.

2. Cracked product exit at 850 OC and are rapidly quenched to 300 0C to

prevent secondary reaction

3. Product scrubbed to remove H2S and CO2 then dried.

4. The C2 & C3 component separated by low temperature fraction

distillation.

5. The C4 component be separated by chemical mean because their boiling

point are too similar 17
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 Improve the performance steam
• To carry out the reaction in thecracking
presence of a catalyst

• The main technology developments in catalytic steam cracking using metal oxide
and zeolite based catalysts. A promising technology, although still in laboratory
research stage, is Japan's AIST process using a lanthanum-modified ZSM-5
catalyst.

• When cracking light naphtha at 650°C (1200°F), the process achieves an overall
ethylene-plus-propylene yield of about 70 wt% and provides significant potential
savings in both investment and production costs. 20
3. Two Step Conversions of Ethanol to
Butadiene
Section 1 C2H5OH  CH3CHO + H2
2(C2H5OH)  C4H8O2 + 2H2

• Catalyst : BASF K-310 (CuO/ZnO/Al2O3)

• Conversion of Ethanol : 52.7%
• Selectivity : (CH3CHO = 87.5%) and (C4H8O2 = 12.5%)

Specification: Type : packed bed reactor

Temperature : 392 F
Pressure:14.7psia

Section 2: Section all hydrogen gas

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Section 3 C2H5OH + CH3CHO  C4H6 + 2(H2O) (MAIN)
2(CH3CHO)  C4H8O2
C2H5OH  C2H4 + H2O (BY -PRODUCT)

• Catalsyt : Mg0/SiO2
• Conversion of Ethanol and Acetaldehyde = 48%
• Selectivity (Butadiene = 68%, Ethylene = 26%, Ethyl Acetate =
9%)

Specification: Type = Packed Bed Reactor

Temperature = 662F
Pressure = 14.7psia)
Section 4 Catalyst Used
• Multi-metal oxide
catalyst
• Mg0/SiO2
• BASF K-310
(CuO/ZnO/Al2O3)
 Hazard SAFETY !
• Extremely Flammable Gas
4
Flashpoint : -76 °C 2 2
Ignition Temp. : 414°C

• Thermal decomposition may produce

CO or CO2.
Normally unstable and readily
Intense orviolent
Rapidly
undergo continued
vaporize exposure
at normalcould
decomposition but
• May react violently with oxidants &
cause temporary
atmospheric
do incapacitation
pressure
not detonate. and or
May react
form explosive mixture with air. possiblewith
temperature,
violently residual
or waterinjury
is readily unless
dispersed
or may form
prompt
in airmedical
potentiallyand willattention
burn
explosive is given.
readily.
mixtures with
• Carcinogenic (long term exposure) water.
Entry Route SAFETY !
& Effects
SKIN EYE INGESTION INHALATION
Entry: Absorption Entry: Vapor Entry: Nose

Effects: Cause Effects: Cause minor Effect: Dizziness,

irritation. Due to its discomfort or blurring of vision
rapid rate of irritation and nausea. An
evaporation, it can anesthetic that cause
cause tissue freezing First aid: Seek Unlikely. respiratory paralysis
or frostbite. immediate medical or death.
advice. Never apply
First aid: Remove oil or ointment into First aid: Prompt
contaminated the eyes without medical attention.
clothing & flush consulting medical Quickly remove from
affected area with expertise. contaminated area.
warm water & soap.
Storage & SAFETY !
Handling Cylinders should
be stored upright
Keep away from open flame. No and firmly secured
smoking near the area or product.

Secured in cool,
dry and well-
ventilated areas.
Do not drag, slide or
roll the cylinders. !
Valve protection caps
must remain in place.
Control & SAFETY !
Protection

PPE
Local exhaust
preventing
accumulation
above exposure limit.
(Hood with forced
ventilation)
Fire Fighting
Measure
SAFETY !
• Leaking gas can be ignited by
flames, sparks or any other
ignition sources at the
locations.
• If leaking gas catches fire, do
not extinguish flames if the
source of fuel is shut off.
• Unburned vapors may spread
from the leak, creating an
explosive re-ignition hazard.
CO2, Dry
chemical, water
spray / fog
• Immediately cool
containers with water
from maximum safe
distance.
• If it is safe, stop the gas
flow or remove ignition
sources or remove the
containers away from the
fire area.
APPLICATION
OF
BUTADIENE
32
 WASTE MANAGEMENT

• The purpose of this process is to reduce the waste from

butadiene industry.

• It includes minimization, processing, storage, recycling,

and final disposal of product.

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Reduce
• Pollution can be minimized by reducing the need to
harvest new raw material.
• Reduces greenhouse gas emissions that contribute to
global climate change

Recycle Reuse
• It is an excellent way to dispose of • Damaged tires can be
unwanted butadiene products repaired and used again.
• Many useful products can be produce.
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 SUSTAINABILITY !
To create and maintain the
conditions under which
humans and nature can
exist in productive
harmony to support
present and future
generations
Objectives

• Work to more efficient of uses of

butadiene.
• Build sustainable awareness to the butadiene value.
• To increase the economy of butadiene.
• To develop more environment-friendly products.
• Contribute to climate protection.
How ? • Switch to
Renewable
energy

• Develop new product

• Reduce waste from process

Recycle
process

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