alpha olefins production expertise - conference websites · 4 differentiating and integrated offer...

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Alpha Olefins

Production Expertise

Fabien Lundy

2

Introduction

Production of 1-butene Co-monomer

• Recovering Native 1-butene from Raw C4 Cut

• AlphaButol®: On-purpose Ethylene to 1-butene

Production of 1-hexene Co-monomer

• AlphaHexol™: On-purpose Ethylene to 1-hexene

Agenda

Axens – Egypt Downstream Summit, February 2016

3

Introduction






Agenda


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Differentiating and integrated offer to its customers

Axens Major Actor


Technology supply • Pioneering technologies

• Conditions for optimum

performances

• Flexible design

Innovative high

efficiency internals • EquiFlow trays

• Catapac dense loading

Catalyst supply • Continuous R&D

• Cost effective product

developments

• LD series and more

Follow-up all along

the life of the unit • Troubleshooting

• Contamination experience

• Advanced process control

Continuous improvement process

5

0

100

200

300

400

500

600

700

800

900

1980 1990 2000 2010 2020 2030

On Demand Alpha Olefins Production

Co-monomer requirements: 1-butene and 1-hexene for

polyethylene applications

World demand index Annual growth

1980-2030

~ 4 %

~ 3 %

~ 2 %

~ 1 %

GDP*: Gross Domestic Product Source : Total

Polymer demand

GDP*

Oil prod.

Gas prod.

Sustained growth for

LLDPE and HDPE

demand

• 1-butene and 1-hexene

2010-2015 AAGR ~ 5 %


1-butene and

1-hexene sourcing?

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Co-monomers Sourcing

1-butene and 1-hexene in C4 and C6 fractions

1-butene and 1-hexene sourcing?

• Beyond simple distillation to extract the desired isomer

• New technology answers: on-purpose ethylene oligomerization


1-hexene 1-butene

AlphaButol® & AlphaHexol™ dedicated processes

for polymer grade 1-butene and 1-hexene

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Axens Technologies for Ethylene Plants

MAPD selective

hydrogenation

C4 acetylenes

selective

hydrogenation

Purification

Multibed

Dimerization

AlphaButol

Trimerization

AlphaHexol

Butadiene

BD rich

selective

hydrogenation

Butadiene

Extraction

C4

etherification

Catacol

Skeletal

isomerization

Iso-5

C4/C5 olefins

hydrogenation

C5 etherification

Catacol

Pygas 1st Stage

Hydrogenation

(GHU-1)

Pygas 2nd Stage

Hydrogenation

(GHU-2)

BD lean selective

hydro

2-butene

maximization

Isobutene

Purif

Isopure

Oligomerization

Selectopol

Polynaphtha

PolyFuel

Olefins

hydrogenation

Aromatics recovery

Sulfolane

Morphylane

Dimerization

Dimersol-X

Hydration

Dehydrogenation

Super

fractionation

BD lean selective

hydro

1-butene

maximization

Ste

am

Cra

ck

er

Fu

rna

ce

s &

Dis

tilla

tio

n S

ec

tio

n

Removal of

arsenic &

mercury

RAM II

1-hexene

Propylene

Butadiene

1-butene

Isobutane

Isobutene

Octenes

N-butane

MEK

MTBE, ETBE

Solvents

TAME, TAEE

Benzene

Toluene

Mixed xylenes

to car

fuels pool Condensates

Ethylene

Benzene production

(HydroDeAlkylation)

Benzene

saturation

Cyclohexane Cyclohexane

C3/C4 total

hydrogenation

C5

C6+ C6-C8

C9+

2-butenes

rich cut

Advanced Pygas

Upgrading

APU


Dimerization

AlphaButol 1-butene

Butadiene

BD rich

selective

hydrogenation

C4 etherification

Catacol

Super

fractionation

BD lean selective

hydro

1-butene

maximization

Trimerization

AlphaHexol 1-hexene

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Axens: long and extensive experience in the field of

heterogeneous catalysis

Heterogeneous catalysis: successful but with

identified fields for improvement

• Distribution

• Handling poisoning

• Controlling exotherms

• Evolution of the catalytic activity over time

Developing breakthroughs to improve the situation

Homogeneous Catalysis


Homogeneous catalysis

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Research initiated mid 60’s: > 50 years involvement

Several processes applying this breakthrough technology

Maintained know-how along the years

Yves Chauvin: Nobel prize in chemistry 2005

Axens Experience in Homogeneous Catalysis


More than 100 references

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Introduction






Agenda


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1-butene from Raw C4 Cut (1/3)


BD transformed

into n-butenes

or extracted

Handling the butadiene rich cut

BD

Or

BD rich cut selective

hydrogenation

BD extraction

MTBE

Isobutene

removed

Methanol

Specific know-how.

Catalytic distillation

involved

MTBE High

Conversion

Hydrogen

BD spec

ensured

BD traces

hydrogenation with

1-butene

maximization

2-butenes+n-butane

1-butene

Isobutane

rich cut

C4 Fraction

Recovered

Raw C4 cut from debutanizer

overhead

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Axens: single source supplier for all technologies

• High conversion MTBE

• Selective hydrogenation maximizing 1-butene production

• Superfractionation

• Purification (if required)

• Ancillary services

› Single source designer

› Single source operation support, advanced control

Latest started plant with Axens’ technology: 4Q42011

Specific technology items

• Catacol™& “Doublets” for catalytic distillation

• Highly selective catalyst towards 1-butene

• Heat pump option

1-butene from Raw C4 Cut (2/3)


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Introduction






Agenda


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Axens Answer to Alpha Olefins Sourcing


98.0

98.5

99.0

99.5

100.0

1-b

ute

ne

pu

rity

, vo

l%

Date

Typical required specification: 99.0 %

• On-site production

• On-demand capacity

• High and constant co-monomer quality

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Selectivity On-purpose Mechanism


M M

H

M

Catalysts +

co-catalysts

2 C2H4

Selective formation of the alpha-olefin

• Not a chain growth mechanism

• Highly selective towards desired oligomer

Mechanism in brief

• Activation of catalyst complex

• Concerted coupling of ethylene

• Stabilized metallacycle intermediate

• Intramolecular hydrogen transfer

• Metallacycle opening: alpha olefin

formation

Selectivity induced by the stability of the metallacyclic

intermediate = Axens’ know-how in catalyst design

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Polymer grade 1-butene for

LLDPE & HPDE

Process simplicity and

ease of operation

High flexibility

Low operating temperature

and pressure

Operating in liquid phase

with no solvent required

No heat input

to the reaction section

Carbon steel equipment

AlphaButol Key Features


Selective ethylene

dimerization mechanism

Ethylene

feed

Reactor

Recycle

column 1-butene

C6+ cut Catalyst

removal

Catalyst

preparation

and storage

1-butene

column

Spent catalyst

LnM + L n M

1-butene 2 C2H4

M = Metal

Ln = Ligand

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Introduction






Agenda


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Similar to AlphaButol, backed by

extensive industrial experience in

homogeneous catalysis

Polymer grade 1-hexene suitable

for LLDPE & HPDE

Efficient ethylene feed use

Process simplicity and

ease of operation

High flexibility

Mild operating temperature

and pressure

Carbon Steel Equipment

AlphaHexol Key Features


Selective ethylene

trimerization mechanism LnM +

1-hexene 3 C2H4

M = Metal

Ln = Ligand

LnM

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Succeeding in alpha-olefins production

1-butene production

• Extensive know-how of different available pathways

• Native 1-butene recovery from native raw C4 cut

› Scheme involving several steps

› Axens: single source supplier of all necessary technologies

• AlphaButol®: on-purpose ethylene dimerization

1-hexene production

• AlphaHexol™: on-purpose ethylene trimerization

Conclusion


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Axens Succeed Together Blog

axens.net/blog

alpha olefins production expertise - conference websites · 4 differentiating and integrated offer...

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