WO2007014593A1 - Method for producing linear alpha-olefins with improved product distribution - Google Patents

Method for producing linear alpha-olefins with improved product distribution Download PDF

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Publication number
WO2007014593A1
WO2007014593A1 PCT/EP2006/005645 EP2006005645W WO2007014593A1 WO 2007014593 A1 WO2007014593 A1 WO 2007014593A1 EP 2006005645 W EP2006005645 W EP 2006005645W WO 2007014593 A1 WO2007014593 A1 WO 2007014593A1
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WO
WIPO (PCT)
Prior art keywords
reactor
catalyst components
olefins
catalyst
linear alpha
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2006/005645
Other languages
French (fr)
Inventor
Peter Fritz
Heinz BÖLT
Karl-Heinz Hoffmann
Hans-Jörg ZANDER
Fuad Mosa
Turky Al Jasser
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Linde GmbH
Saudi Basic Industries Corp
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Linde GmbH
Saudi Basic Industries Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Linde GmbH, Saudi Basic Industries Corp filed Critical Linde GmbH
Priority to JP2008524372A priority Critical patent/JP2009502989A/en
Publication of WO2007014593A1 publication Critical patent/WO2007014593A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/26—Catalytic processes with hydrides or organic compounds
    • C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2445—Stationary reactors without moving elements inside placed in parallel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron

Definitions

  • the present invention relates to a method for preparing of linear alpha-olefins by oligomerizing of ethylene in the presence of an organic solvent and a homogenous catalyst comprising a zirconium component and an organoaluminum component.
  • a catalyst is utilized in that process comprising a zirconium component and an organoaluminum component which acts as an activator.
  • DE 43 38 414 Cl discloses a process for the production of linear alpha-olefins, wherein one reactor is utilized into which a catalyst solution and ethylene are introduced. That process results in a product distribution of linear alpha-olefins having C 2 -C 28 carbon atoms. It is already known in the field of the art that the product distribution may be varied by changing the ratio of the catalyst components, i.e. the ratio Al/Zr. The nature of the catalyst drives the distribution either to the light or heavy products.
  • This object is achieved in that the method is carried out in more than one reactor being operated in parallel, wherein for each reactor the method conditions and parameters are independently adjustable.
  • the Al/Zr ratio for the catalyst components is adjustable.
  • temperature and pressure may be individually adjustable in each reactor.
  • each reactor has at least one feed line for introducing the catalyst components, each dissolved in a solvent, into the reactor.
  • the catalyst components may be pre-mixed prior to introduction into the reactor.
  • each reactor has two feed lines to introduce the catalyst components separately into the reactor.
  • the outlet of some or all reactors is blended.
  • control device controls the amount and rate of introduction of catalyst and/or catalyst components.
  • the organoaluminum component may be Al(C 2 Hs) 3 , Al 2 Cl 3 (C 2 Hs) 3 or A1C1(C 2 H 5 ) 2 .
  • the production flexibility may be increased and the product distribution may be adjusted according to market requirements, if a method is utilized wherein more than one reactor is operated in parallel, wherein for each reactor the method conditions and parameters may be adjusted independently from the other ones.
  • the product distribution of each available reactor is adjusted individually, so that the required overall distribution can be met and market requirements may be fulfilled.
  • the production quantity of specific products can be maintained even during shutdown of one reactor (e.g. for maintenance and cleaning) by adjustment of the reactors remaining on stream.
  • FIG. 1 illustrates a schematic diagram of a plant for the production of linear alpha olefins having four reactors to be operated in parallel.
  • the method for preparing of linear alpha-olefins is conducted in a plant having more than one reactor being operated in parallel.
  • the figure shows four reactors 1.
  • one catalyst component for example the zirconium component
  • a further distribution line 3 is provided to introduce the second catalyst component, for example the organoaluminum component, into each reactor.
  • the zirconium component and organoaluminum component are mixed directly in the reactor.
  • the catalyst components may be pre- mixed prior to introduction into each reactor, so that only one common distribution line is required.
  • each reactor is provided with separate lines for introducing the catalyst components, so that it is possible to introduce in each reactor different catalyst components, for example different organoaluminum compounds to influence the production flexibility.
  • each control device 4 for controlling the amount and rate of the catalyst components to be introduced is additionally provided.
  • Each control device 4 is thus employed to control all method conditions and parameters in each reactor 1, e.g. also temperature and pressure. Of course, only once control device 4 may be necessary to control all reactors.
  • Each reactor is also provided with an ethylene feed line 5.
  • the catalyst components are dissolved in a solvent, wherein toluene is preferably utilized.
  • At least one discharge line 6 is provided for each reactor to discharge the reaction products.
  • One skilled in the art is aware that several discharge lines are to be provided to remove both gaseous and liquid compounds from the reactor, which are omitted in the figure for -A-
  • the discharge lines 6 of each reactor may combine so that the products obtained in the reactors may be mixed.
  • the reaction conditions and parameters may be adjusted in each reactor individually, the production flexibility and especially the product distribution may be optimized to fulfill market requirements.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention relates to a method for preparing of linear alpha-olefins by oligomerizing of ethylene in the presence of an organic solvent and a homogenous catalyst comprising of a zirconium component and an organoaluminum component, characterized in that the method is carried out in more than one reactor being operated in parallel, wherein for each reactor the method conditions and parameters are independently adjustable.

Description

Method for producing linear alpha-olefms with improved product distribution
The present invention relates to a method for preparing of linear alpha-olefins by oligomerizing of ethylene in the presence of an organic solvent and a homogenous catalyst comprising a zirconium component and an organoaluminum component.
Methods for the production of linear alpha-olefins are widely known in the art. Usually, a catalyst is utilized in that process comprising a zirconium component and an organoaluminum component which acts as an activator.
For example, DE 43 38 414 Cl discloses a process for the production of linear alpha-olefins, wherein one reactor is utilized into which a catalyst solution and ethylene are introduced. That process results in a product distribution of linear alpha-olefins having C2-C28 carbon atoms. It is already known in the field of the art that the product distribution may be varied by changing the ratio of the catalyst components, i.e. the ratio Al/Zr. The nature of the catalyst drives the distribution either to the light or heavy products.
However, even changing the Al/Zr ratio does not meet the market requirements in all cases. It is therefore an object of the present invention to provide a method for preparing of linear alpha- olefins which overcomes the drawbacks of the prior art. Especially, the method shall be provided showing improved product flexibility, especially with regard to product distribution.
This object is achieved in that the method is carried out in more than one reactor being operated in parallel, wherein for each reactor the method conditions and parameters are independently adjustable.
Preferably, wherein the Al/Zr ratio for the catalyst components is adjustable. Additionally, temperature and pressure may be individually adjustable in each reactor.
In one embodiment, each reactor has at least one feed line for introducing the catalyst components, each dissolved in a solvent, into the reactor.
The catalyst components may be pre-mixed prior to introduction into the reactor.
Alternatively, each reactor has two feed lines to introduce the catalyst components separately into the reactor.
Most preferred, the outlet of some or all reactors is blended.
Additionally, the amount and rate of introduction of catalyst and/or catalyst components are controlled by a control device.
Preferably, the zirconium component has the formula ZrCl4-01Xm, wherein X = OCOR or OSO3R' with R and R' being independently alkyl, alkene and phenyl, and wherein O < m < 4.
Finallly, the organoaluminum component may be Al(C2Hs)3, Al2Cl3(C2Hs)3 or A1C1(C2H5)2.
Surprisingly, it was found that the production flexibility may be increased and the product distribution may be adjusted according to market requirements, if a method is utilized wherein more than one reactor is operated in parallel, wherein for each reactor the method conditions and parameters may be adjusted independently from the other ones. Thus, the product distribution of each available reactor is adjusted individually, so that the required overall distribution can be met and market requirements may be fulfilled. As a further advantage of the method according to the present invention, the production quantity of specific products can be maintained even during shutdown of one reactor (e.g. for maintenance and cleaning) by adjustment of the reactors remaining on stream.
Additional advantages and features of the inventive method are further illustrated with reference to the accompanying drawing, wherein the figure illustrates a schematic diagram of a plant for the production of linear alpha olefins having four reactors to be operated in parallel.
According to the invention, the method for preparing of linear alpha-olefins is conducted in a plant having more than one reactor being operated in parallel. The figure shows four reactors 1. Into each reactor 1 , one catalyst component, for example the zirconium component, may be introduced through a distribution line 2. A further distribution line 3 is provided to introduce the second catalyst component, for example the organoaluminum component, into each reactor. Thus, the zirconium component and organoaluminum component are mixed directly in the reactor. According to another embodiment of the invention, the catalyst components may be pre- mixed prior to introduction into each reactor, so that only one common distribution line is required. In a further embodiment (not shown), it is possible that each reactor is provided with separate lines for introducing the catalyst components, so that it is possible to introduce in each reactor different catalyst components, for example different organoaluminum compounds to influence the production flexibility.
For each reactor a control device 4 for controlling the amount and rate of the catalyst components to be introduced is additionally provided. Each control device 4 is thus employed to control all method conditions and parameters in each reactor 1, e.g. also temperature and pressure. Of course, only once control device 4 may be necessary to control all reactors. Each reactor is also provided with an ethylene feed line 5. Of course, the catalyst components are dissolved in a solvent, wherein toluene is preferably utilized.
Additionally, at least one discharge line 6 is provided for each reactor to discharge the reaction products. Someone skilled in the art is aware that several discharge lines are to be provided to remove both gaseous and liquid compounds from the reactor, which are omitted in the figure for -A-
the purpose of clarity. The discharge lines 6 of each reactor may combine so that the products obtained in the reactors may be mixed. As the reaction conditions and parameters may be adjusted in each reactor individually, the production flexibility and especially the product distribution may be optimized to fulfill market requirements.
The features disclosed in the foregoing description, in the claims and in the drawings may, both separately and in any combination thereof, be material for realizing the invention in diverse forms thereof.

Claims

Claims
1. Method for preparing of linear alpha-olefins by oligomerizing of ethylene in the presence of an organic solvent and a homogenous catalyst comprising a zirconium component and an organoaluminum component, characterized in that the method is carried out in more than one reactor being operated in parallel, wherein for each reactor the method conditions and parameters are independently adjustable.
2. Method according to claim 1, wherein the Al/Zr ratio for the catalyst components is adjustable.
3. Method according to claim 1 or 2, wherein temperature and pressure are individually adjustable in each reactor.
4. Method according to any of the preceding claims, wherein each reactor has at least one feed line for introducing the catalyst components, each dissolved in a solvent, into the reactor.
5. Method according to any of the preceding claims, wherein the catalyst components are pre-mixed prior to introduction into the reactor.
6. Method according to claim 4, wherein each reactor has two feed lines to introduce the catalyst components separately into the reactor.
7. Method according to any of the preceding claims, wherein the outlet of some or all reactors is blended.
8. Method according to any of the preceding claims, wherein the amount and rate of introduction of catalyst and/or catalyst components are controlled by a control device.
9. Method according to any of the preceding claims, wherein the zirconium component has the formula ZrCl4-mXm, wherein X = OCOR or OSO3R' with R and R' being independently alkyl, alkene and phenyl, and wherein O < m < 4.
10. Method according to any of the preceding claims, wherein the organoaluminum component is Al(C2Hj)3, Al2Cl3(C2Hs)3 or AlCl(C2Hs)2.
PCT/EP2006/005645 2005-08-02 2006-06-13 Method for producing linear alpha-olefins with improved product distribution Ceased WO2007014593A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2008524372A JP2009502989A (en) 2005-08-02 2006-06-13 Process for the production of linear alpha olefins with improved product distribution

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05016762.6 2005-08-02
EP05016762A EP1749807A1 (en) 2005-08-02 2005-08-02 Method for producing linear alpha-olefins with improved product distribution

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JP (1) JP2009502989A (en)
CN (1) CN101258117A (en)
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US8845542B2 (en) 2009-09-09 2014-09-30 Unex Corporation Blood vessel function inspecting apparatus

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CN103118777B (en) 2010-05-24 2016-06-29 希路瑞亚技术公司 nanowire catalyst
CN103764276B (en) 2011-05-24 2017-11-07 希路瑞亚技术公司 Catalysts for the Oxidative Coupling of Methane
US20130158322A1 (en) 2011-11-29 2013-06-20 Siluria Technologies, Inc. Polymer templated nanowire catalysts
CA3092028C (en) 2012-01-13 2022-08-30 Lummus Technology Llc Process for separating hydrocarbon compounds
US9446397B2 (en) 2012-02-03 2016-09-20 Siluria Technologies, Inc. Method for isolation of nanomaterials
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US9969660B2 (en) 2012-07-09 2018-05-15 Siluria Technologies, Inc. Natural gas processing and systems
WO2014089479A1 (en) * 2012-12-07 2014-06-12 Siluria Technologies, Inc. Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products
WO2014143880A1 (en) 2013-03-15 2014-09-18 Siluria Technologies, Inc. Catalysts for petrochemical catalysis
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US10519077B2 (en) 2015-09-18 2019-12-31 Chevron Phillips Chemical Company Lp Ethylene oligomerization/trimerization/tetramerization reactor
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Also Published As

Publication number Publication date
JP2009502989A (en) 2009-01-29
EP1749807A1 (en) 2007-02-07
RU2008107950A (en) 2009-09-10
CN101258117A (en) 2008-09-03

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