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1-Hexene Co-Monomer for

Polyethylene: Technology and


Modularization Option

Valrie GEORGES, Prosernat


Gildas ROLLAND, Axens
Agenda
Searching for an Optimized 1-Hexene Solution

Modul a r
AlphaHexol
Polyethylene Co-Monomers Market
Outlook
1-Hexene Comonomer Production
Technology
Axens Modularization Solution
Efficiency

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 2
Agenda
Searching for an Optimized 1-Hexene Solution

Modul a r
AlphaHexol
Polyethylene Co-Monomers Market
Outlook
1-Hexene Comonomer Production
Technology
Axens Modularization Solution
Efficiency

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 3
Polyethylenes Market Outlook
Their market is growing fast +4.2160
% +2.9% +5.4%
140

120

WORLD
LLDPE
100

80 LDPE
60 HDPE
40

20

0
2016 2025 Source: Axens

50
+4.6% +3.0% +6.6%

Middle East & Africa


40

30

20

10

0
2016 2025
27% 33%
24% 30%
29% 35%

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 4
Polyethylenes Market Outlook
Their market is growing fast +4.2160
% +2.9% +5.4%

LLDPE and HDPE main drivers 140

120

WORLD
LLDPE
Selection=f (properties / application) 100

80 LDPE
Mechanical resistance, 60 HDPE
Translucence, 40

20

Properties=f (co-monomer type, %) 2016 2025 Source: Axens

Co-monomers for LL and H 50


+4.6% +3.0% +6.6%

Middle East & Africa


40
1-butene 30

1-hexene 20

Co-monomers demand growing


10

0
2016 2025
27% 33%
24% 30%
29% 35%

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 5
Iran Ethylene Production Outlook
1-Butene & 1-Hexene Sourcing

Tabriz 1-Hexene?
No installed production in Iran
Mahabad
Ethylene availability: yes
Large ethylene crackers
ARPC Shazand West ethylene pipeline
Khorramabad
MTO & Makran development area
BIPC
AKPC
Marun Why? Where? How?
Bandar Imam Gachsaran
JAM
Arya Sasol
Kavian
Morvarid
Operating ethylene plant
Assaluyeh
West ethylene pipeline
1-hexene plant

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 6
Positive Elements for 1-Hexene Dvpt in Iran
Uptake
LLDPE and HDPE increasing demand worldwide and in Iran
Local and/or export markets accessibles
Strategic location of Iran
1-hexene liquid co-monomer
Production
On-purpose technology ready
High quality
High yield
Similarity to AlphaButol

AlphaHexol trimerization
process for 1-hexene

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 7
Agenda
Searching for an Optimized 1-Hexene Solution

Modul a r
AlphaHexol
Polyethylene Co-Monomers Market
Outlook
1-Hexene Co-Monomer Production
Technology
Axens Modularization Solution
Efficiency

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 8
Ethylene Trimerization Technology
Pathways to 1-hexene
Status Reason
Extraction from
steam cracker C6 cut Too many coboilers, contamination,

No expansion possible: specific to


Fischer Tropsch C6
olefins separation South African FT units. No further unit
of same kind to be built.

Full range process ~ Low purity, low yield

On-purpose High purity, high yield


trimerization Open licensing: available in Iran

Ethylene trimerization technology best candidate

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 9
Axens AlphaHexol Trimerization Technology

Among the suite of homogeneous catalysis licensing


Cyclohexane Dimersol AlphaButol AlphaHexol
> 100
Nb of ref. 36 38 33 1
Offered since 1976 1977 1987 2011
references

Extensive, continuous R&D involvement


Development started in the 60s
Researcher Pr Chauvin Nobel Prize in Chemistry 2005
Legacy to his team
Nobel Prize Laureate Yves Chauvin

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 10
Axens AlphaHexol Trimerization Technology
From one benchmark to another?
Strong similarity AlphaHexol / AlphaButol
High performance processes
Quality
Key features for AlphaHexol polymer grade 1-hexene
1-hexene purity: > 99%
Yield towards 1-hexene: > 85%
Operation flexibility 1-hexene
AlphaButol know-how reused others

Pilot data sample GC

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 11
Axens AlphaHexol Trimerization Technology
From one benchmark to another?
Strong similarity AlphaHexol / AlphaButol
Chemistry
Homogeneous catalysis Near perfect distribution
Continuous poison control
Feed, catalyst
& products
by catalyst renewal
soluble together Ease of heat removal and
accurate temperature
Isomer specific control

Insaturation
L1 Controlled active metal
available for electronic configuration
reaction
L2
M Ensure desired isomer
L3 formation
Coordination
sphere
L4
Ligand

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 12
Axens AlphaHexol Trimerization Technology
From one benchmark to another?
Strong similarity AlphaHexol / AlphaButol
Chemistry catalyst precursor +
alkyl aluminium
Mechanism,
Same hybrid transfer
M 2 C2 H 4
principle
Same TEA alkyl aluminium
H
High selectivity
High product purity
No Cl, no aromatics M

M
C 2H 4

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 13
Axens AlphaHexol Trimerization Technology
From one benchmark to another?
Strong similarity AlphaHexol / AlphaButol
Evolution to switch from 1-butene to 1-hexene
Catalyst selection for C6 selectivity
Specific operating window: T,P, residence time
Among induced changes:
Thermal integration
Operation above waxes
melting point
Fouling elimination

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 14
Axens AlphaHexol Trimerization Technology
From one benchmark to another?
Strong similarity AlphaHexol / AlphaButol
Scheme and design
Ethylene

Reaction
Catalyst
Distillation
-olefin
neutralization and
Section Section
removal section Purges, by-

products
Spent catalyst
Catalysts and
alkyl aluminium

Moderate T, P ; use of carbon steel ; catalyst removal system,


conventional distillation
AlphaButol operators know-how re-used

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 15
Towards Standardization?
Catalysts and
alkyl aluminium

Alkyl aluminium TEA


Same for AlphaButol and
AlphaHexol
Mutualized in dual 1-butene +
1-hexene complex
Sophisticated although quite
standard section for all our
designs
Time and cost savings if
standardized to another level?

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 16
From Idea to Implementation
Operating
15 kta 1-butene
plant

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 17
Agenda
Searching for an Optimized 1-Hexene Solution

Modul a r
AlphaHexol
Polyethylene Co-Monomers Market
Outlook
1-Hexene Comonomer Production
Technology
Axens Modularization Solution
Efficiency

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 18
Modularization: Some Definitions
PAU: Pre-Assembled Unit, Loose equipment: not pre-
physically transportable in assembled: ex. large
1 piece column, large drum,

h l, L, h, weight compliance
with transport and site
constraints
l
L

Interconnexions:
connecting lines and Module: sum of PAU
equivalent from PAU to constituting a signifying
others and loose block/unit
Example of NHT/CCR reformer Axens technologies with modularization approach

equipment

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 19
Ready to Plug In Concept Drivers?
Site specific decision depending on several factors
Safety Cost & Schedule Technical
Implementation Reduced time to No limitation due
within operating production, better NPV to hot, cold, off-
process units Skilled and adapted shore conditions
Workforce in tools & workforce at Remote area
dedicated yard efficiency troublefree
equipped Workforce availability Plot space
workshops ensured optimization
Harsh climates Price

Key constraints review allow identifying the


interest of modularization for each project

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 20
Advantages of Modularization through Axens
Axens one stop shop advantage

Detail Shipping,
Basic Tech
Engineeri installati
Design Services
ng on
Modulari
Procure
zation Start-Up
ment
study
Manufact
uring
1 process, 1 unit, 1 single point
responsibility: Axens

Know-how from project conception to operation

Shared know-how, process understanding and commitment


No losses (time, technical) at interfaces between various actors
Schedule efficient: better time to production thus NPV

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 21
Schedule Efficiency with Axens Modularization
Licensor and modularization Axens modular schedule timeline
or stick built option selection Stick built approach timeline
100% time
Basic saved Axens Time saving
engineering single source through modular Modular
EPC bidding
basic engineering unit
FEED + detail advanced
engineering
~30% production
Procurement
reduction of time
Site civil work Simulatneous
Simultaneous Successive

Equipment installation /
start of activites
activites project activities
module constr +
transport + installation schedule
Pre-comm/
comm
Trial fit and factory
Start-up & acceptance saves
test-run time
Successful
performance test.
Unit on stream

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 22
Schedule Efficiency with Axens Modularization
Licensor and modularization Axens modular schedule timeline
Detail Shipment
stick built option decision Stick built approach timeline
engineering
Basic
engineering

EPC bidding

FEED + detail
engineering

Procurement
Site
Trial fit assembly,
Site civil work
operation
Equipment installation /
module constr +
transport + installation
Pre-comm/
comm
Start-up &
test-run

alpha olefin 1-
butene unit example From modular design KOM to operation

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 23
References
Axens AlphaHexol
1 licensed unit, 25 kta
Modular Prosernat realizations
> 450, all processes included
~25 in Iran

Iran - Bandar Assalouyeh


Aromatics complex/CCR
item. (Axens technology)

Iran - South Pars 2 & 3.


TEG dehydration. (Prosernat technology)

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 24
Combination for Success

Modul a r
AlphaHexol
Performance trimerization technology
NPV optimization via modularization
Most advanced combination through
Axens single responsibility provider
Technolgy
Modular unit construction
Start-up and assistance

Axens' Iran Seminar - Petrochemicals Day - 27 Tir 1396 (18 July 2017) 25
Thank you! And see you on Axens Blog
axens.net/blog

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