Energy Efficient Versalis/Lummus Cumene - Phenol ... · PDF fileTechnology for Minimizing...
Transcript of Energy Efficient Versalis/Lummus Cumene - Phenol ... · PDF fileTechnology for Minimizing...
A World of Solutions
Recent Advances in Cumene/Phenol/Acetone Technology:
Energy Efficient Versalis/Lummus Cumene - Phenol Technology for Minimizing Operating Costs
Ronald Venner
Ajay Gami
versalis technology conference : value to compete
15 November 2013
Bangkok, Thailand
Methanol
Butadiene
Butylene
Lummus Chemical Processes
Cumene
Polystyrene Styrene Ethylbenzene
Butadiene
Extraction
Maleic
Anhydride
Naphtha
AGO/VGO
Steam
Cracking
Ethane
LPG
Propane Dehydrogenation
Butanes
Propane
Propylene
Ethylene
Hydro-
dealkylation
C6-C8s
Benzene Aromatics
Saturation
C4s
Propylene
Polypropylene
Phenol
Dimethyl
Carbonate
Diphenyl
Carbonate
Olefins
Conversion
Dimerization
Butane Dehydrogenation
CO O2
Methanol to
Olefins Methanol
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Separation &
Isomerization
Paraxylene
Reformate or
Mixed Xylenes
Hexene-1 Comonomer
Production
Butene-1
Polycarbonate
BPA
Agenda
• Overview
• Cumene
• Phenol-Acetone
• Acetone Recycle
• Summary
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Technology Alliance
• Versalis SpA
• CB&I
Versalis Cumene-Phenol Experience
• Producing cumene and phenol since 1964
• Started liquid-phase cumene operation in 1996
• Plant operations at two sites – Mantova, Italy – 300,000 MTA
– Porto Torres, Italy – 200,000 MTA (recently shutdown)
• One phenol licensee plant in operation – Domo, Germany – 160,000 MTA
Over 45 years of cumene and phenol plant operations
experience
More than 98% on-stream factor
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Role of Partners
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Technology Licensing CB&I Versalis
Marketing and licensing
Process design
Training
Start-up assistance
Catalyst supply
Follow-up technical service
Technology Maintenance
Process enhancements
Catalyst R&D
Technology Development
Capacity (mta)
FCFC, Taiwan (Expansion) 400,000
GE Plastics, USA 300,000
Herdillia Chemicals, India 100,000
FCFC, Taiwan 200,000
Ertisa, Spain 86,000
Allied Chemical, USA 175,000
Kumho Chemicals, Korea 26,000
Dow Chemical, USA 182,000
Union Carbide, Puerto Rico 91,000
Georgia-Gulf, USA 82,000
Texaco Chemical, USA 43,000
BTL of Illinois, USA 39,000
Cumene/Phenol Technology Experience
Three new Versalis/Lummus technology projects:
Petronas, Malaysia – 203 kMTA phenol
FCFC, China - 450 kMTA cumene/300 kMTA phenol
Essar, India - 270 kMTA cumene/200 kMTA phenol
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Agenda
• Overview
• Cumene
• Phenol-Acetone
• Acetone Recycle
• Summary
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Versalis/Lummus Cumene Process
• State-of-the-art, liquid-phase, zeolite technology
• Highly experienced Versalis/Lummus partnership – Versalis: leading petrochemical company with production
plants based on PBE-type proprietary zeolite catalyst
– CB&I: long history of development and commercialization with zeolitic aromatic alkylation processes, both cumene and ethylbenzene
• Superior PBE-1 zeolite catalyst based technology
• High quality products suitable for all requirements
• Low investment and plant operating cost
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Chemistry – Alkylation & Transalkylation
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Alkylation
+ C 3 H
6
Transalkylation
C 3 H
6 + CH(CH3)2
,etc...
(Cumene)
(Diisopropylbenzene)
Other side products: n-propylbenzene, non-aromatics, heavies,
+ 2 , etc...
Other side products: EB, butylbenzene, heavies
(Propylene) (Benzene)
(Cumene) (Propylene)
(Diisopropylbenzene) (Cumene) (Benzene)
CH(CH3)2
[CH(CH3)2]2
[CH(CH3)2]2 CH(CH3)2
Propylene Cumene Residue
Alkylator Steam Steam
Heat Heat
Transalkylator Benzene Column
Cumene
Column
PIPB
Column
PIPB
Heat
CW Steam
Steam
Recycle
Recycle
Benzene
Heat
Water
Benzene
Cumene Process Flow Scheme
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PBE-1 Catalyst Advantages
• Versalis PBE-1 Proprietary Beta Zeolite – Alkylation and transalkylation
• Superior yield
• Superior catalyst formulation – Unique morphology
– Optimum zeolite acidity and porosity
– Demonstrated superior stability/durability
– Ease of regeneration
• Non-detectable catalyst deactivation rate – Extended catalyst life
– Unique catalyst performance tracking system
– Proprietary catalyst rejuvenation procedure
• High mono selectivity and negligible formation of coke
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Cumene Technology Highlights
• 99.7 wt% product yield
• 100% propylene conversion throughout entire run
• Ultra high cumene product purity of 99.95 wt% – N-propylbenzene (<300 wppm)
– low Bromine Index (< 1) without clay treatment
• Water injection allows for higher reactor operating temperatures without increasing impurity make
• Efficient LP steam production which is utilized in the phenol unit
• All carbon steel construction
• Simple operation and low maintenance
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Agenda
• Overview
• Cumene
• Phenol-Acetone
• Acetone Recycle
• Summary
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Versalis/Lummus Phenol Process
• State-of-the-art technology – Safe and reliable wet oxidation technology
based on gas lift reactors
– Optimized cleavage technology based on loop reactors
– Glycol based extractive distillation technology
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Cumene
Spent Air
CHP
CW
Air
OH
Phenol
Acetone
CH 3 - C - CH
3
O
Alpha-Methylstyrene
CH 3 - C - CH
3
H
CH 3 - C - CH
3
O
Acid
Cumene Hydroperoxide
CH 3 - C - CH
3
O OH
CH 3 - C
Acetophenone
CH 3 - C CH
2
OH
Dimethyl benzyl alcohol
Cumene
Acid
O 2
O 2
O 2
H 2
Process Chemistry
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OH
Phenol
Acetone
CH 3 - C - CH
3
O
Alpha-Methylstyrene
CH 3 - C - CH
3
H
CH 3 - C - CH
3
O
Acid
Cumene Hydroperoxide
CH 3 - C - CH
3
O OH
CH 3 - C
Acetophenone
CH 3 - C CH
2
OH
Dimethyl benzyl alcohol
Cumene
Acid
O 2
O 2
O 2
H 2
Process Chemistry
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• Oxidation
• Cumene stripping
• Cleavage
• Neutralization
• Acetone fractionation
• Phenol extraction
• AMS hydrogenation
• Dephenolation
Process Steps
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Cumene
Air
Fuel
Phenol
Acetone
Oxidation Cumene
Stripping Cleavage Dephenolation
AMS
Hydrogenation
Neutralization
Acetone
Fractionation
Phenol
Extraction
Technology Advantages
• High yield – Cumene consumption of < 1.31 kg/kg of
phenol
• Highest quality products – Only phenol/acetone process commercially
proven to produce pharmaceutical grade acetone
• Low environmental impact of air and water emissions
• Low energy consumption – Glycol based extractive distillation
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Agenda
• Overview
• Cumene
• Phenol-Acetone
• Acetone Recycle
• Summary
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• Over 90% of world’s phenol production currently via cumene hydroperoxide route that produces acetone as a by-product
• Phenol and acetone produced in fixed ratio:
0.62 ton of acetone per ton of phenol
• Market demands for phenol and acetone not in same ratio
OH
Phenol
Acetone
CH 3 - C - CH 3
O
CH 3 - C - CH
3
H
Acid
Cumene Hydroperoxide
- CH 3
O
OH
CH 3 - C
Cumene
O 2
Acetone Recycle Technologies
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Acetone Flexibility Solutions
Acetone Raw IPA Commercial Grade IPA
H2
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Raw IPA
Production
IPA Purification
Section
• Two new Versalis/Lummus technology solutions:
1. Alternate product
– Acetone to isopropyl alcohol (IPA)
2. Propylene feedstock reduction
– Acetone recycle to cumene (under development)
Agenda
• Overview
• Cumene
• Phenol-Acetone
• Acetone Recycle
• Summary
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Versalis/Lummus Partnership
• New technology solutions to minimize acetone byproduct
• State of the art commercially proven technologies
• Only licensor/operator with over 45 years of operating experience
• Unique position to offer full range of phenolic technologies for green polycarbonate production
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Methanol
Cumene Phenol
Dimethyl
Carbonate
Diphenyl
Carbonate
CO O2
Polycarbonate
BPA
Propylene Benzene