EP2655565A2 - Paraffines normales lourde de haute pureté utilisant des systèmes intégrés - Google Patents

Paraffines normales lourde de haute pureté utilisant des systèmes intégrés

Info

Publication number
EP2655565A2
EP2655565A2 EP11851587.3A EP11851587A EP2655565A2 EP 2655565 A2 EP2655565 A2 EP 2655565A2 EP 11851587 A EP11851587 A EP 11851587A EP 2655565 A2 EP2655565 A2 EP 2655565A2
Authority
EP
European Patent Office
Prior art keywords
stream
aromatics
unit
hydrocarbons
heavy
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.)
Withdrawn
Application number
EP11851587.3A
Other languages
German (de)
English (en)
Inventor
Stephen W. Sohn
Andrea G. Bozzano
Jeffrey L. PIEPER
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.)
Honeywell UOP LLC
Original Assignee
UOP LLC
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 UOP LLC filed Critical UOP LLC
Publication of EP2655565A2 publication Critical patent/EP2655565A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
    • C10G67/06—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including a sorption process as the refining step in the absence of hydrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
    • C10G25/06—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with moving sorbents or sorbents dispersed in the oil
    • C10G25/08—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with moving sorbents or sorbents dispersed in the oil according to the "moving bed" method
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
    • C10G25/12—Recovery of used adsorbent
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/44—Hydrogenation of the aromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
    • C10G67/14—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including at least two different refining steps in the absence of hydrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G7/00—Distillation of hydrocarbon oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/30—Aromatics

Definitions

  • the invention relates to adsorption separation processes.
  • the invention is specifically directed at a process to improve the capacity and purity of normal paraffins.
  • These beds may be considered to be portions of a single large bed whose movement is simulated.
  • the moving bed simulation may be simply described as dividing the bed into series of fixed beds and moving the points of introducing and withdrawing liquid streams past the series of fixed beds instead of moving the beds past the introduction and withdrawal points.
  • a rotary valve used in the Broughton process may be described as accomplishing the simultaneous interconnection of two separate groups of conduits.
  • a flush stream is used to prevent undesirable mixing of components.
  • the flush substance is chosen to be one which is not undesirable for mixing with either main stream, that being purged or that which enters the pipeline after flushing is completed.
  • a second group consists of the conduits associated with the individual beds, that is, which supply and remove fluid from the beds, one conduit being connected between each two beds. It is to be noted that each conduit of the second group serves that dual function of supply and removal, so that it is unnecessary to provide conduits for supplying fluid separate from those for removing fluid.
  • Adsorption separation uses expensive equipment, and the equipment is not readily replaced to increase the production of a product stream. With increasing demand for the products from adsorption separation processes, increasing the throughput and recovery of the products is desirable without having to replace the equipment.
  • the present invention improves the purity of a normal paraffin stream by selectively removing aromatic compounds from the extract stream.
  • the process is for the production of a purified heavy normal paraffin.
  • a hydrocarbon stream is passed to a prefractionation unit to separate out a selected range of hydrocarbons.
  • the prefractionation unit generates a first stream comprising light ends, a second stream comprising heavy ends, and a third stream comprising hydrocarbons in the desired range.
  • the third stream is passed to a hydroprocessing unit where under a hydrogen atmosphere, contaminants within the stream are hydrogenated and removed, creating an effluent stream having reduced contaminants.
  • the effluent stream is processed in an adsorption separation unit, where an extract stream comprising normal paraffins is generated, and a raffinate stream comprising non-normal hydrocarbons is generated.
  • the extract stream is passed to an aromatics adsorption unit to selectively remove aromatic compounds that remain in the extract stream.
  • the aromatics adsorption unit creates a process stream with a reduced heavy aromatic concentration.
  • the process stream is passed to a separation unit to remove residual desorbent and light aromatics.
  • the desorbent and light aromatics are components left in the aromatics adsorption unit during the regeneration of the aromatics adsorbent.
  • Figure 1 is a process flow of the present invention showing the improvement to achieve a high purity normal paraffin
  • Figure 2 is the process for the regeneration of the aromatics adsorber.
  • a high purity heavy normal paraffin is required for some applications.
  • the high purity also includes having a low aromatic content.
  • Conventional methods for producing a heavy normal paraffin result in a product that contains an aromatic content greater than 0.5% by weight.
  • the high purity heavy normal paraffins require a purity of greater than 99.5 wt.% with an aromatic content less than 100 ppm by weight.
  • Conventional methods use a high pressure hydrogenation process to saturate the aromatics, but this does not increase the overall purity of the heavy normal paraffin.
  • Linear alkylbenzenes (LABs) and secondary alkane sulfonates (SASs) are types of surfactant components used for the production of detergents.
  • the production of LABs requires a feedstream of linear olefins, which in turn can be produced from linear paraffins.
  • the linear olefins useful for producing SASs for detergent production have linear carbons chains in the 10 to 20 range, and preferably in the 14 to 17 range.
  • the linear olefins for producing LABs for detergent production have linear carbon chains in the 10 to 20 range, and are preferably grouped to within a range of 4 linear carbon chains, with some examples as 10 to 13, 1 1 to 14, and 14 tol7.
  • LGO light gas oil
  • This also can include hydrocarbons in the kerosene range.
  • the present invention takes a portion of the feedstream, either LGO or other hydrocarbon stream, and further separates the material to provide a purified normal paraffin stream.
  • the present invention is a process for the purification of a heavy normal paraffin.
  • the process includes passing a hydrocarbon feedstream 8 to a prefractionation unit 10.
  • the prefractionation unit 10 separates the feedstream into three streams.
  • the unit 10 generates a first stream 12 of the heavy hydrocarbons, a second stream 14 of light hydrocarbons, and a third stream 16 of intermediate hydrocarbons.
  • the intermediate hydrocarbons are a desired selected group of hydrocarbons in the range of C14 to CI 7 hydrocarbons.
  • the third stream 16 includes normal paraffins, aromatics, branched paraffins and other hydrocarbons.
  • the heavy stream 12 comprises hydrocarbons having 18 or more carbon atoms
  • the light stream 14 comprises hydrocarbons having 13 or fewer carbon atoms.
  • the third stream 16 is passed to a hydroprocessing unit 20, where contaminants, such as sulfur and nitrogen are reacted over a hydroprocessing catalyst under a hydrogen atmosphere 26 and removed. This is done to extend the life of the adsorbent in the adsorption separation unit 30.
  • the hydroprocessing unit 20 partially hydrogenates some of the unsaturated hydrocarbons, such as olefins and aromatics. Hydrogenating a portion of the olefins increases the paraffin content and can increase the yields of normal paraffins.
  • the hydroprocessing unit 20 generates an effluent stream 22 having a reduced contaminant content.
  • the effluent stream 22 is passed to an adsorption separation unit 30, where normal paraffins are separated from the non-normal paraffins and remaining types of hydrocarbons.
  • the adsorption separation unit 30 generates an extract stream 32 that includes normal paraffins and desorbent, but also includes a small amount of aromatic compounds that the process does not remove to a sufficiently low concentration.
  • the extract stream 32 is passed to a paraffin extract purification adsorbent system 40 to remove a significant portion of the residual aromatics in the adsorbent stream 32, and to generate a purified extract stream 42 containing normal paraffins and desorbent.
  • the extract stream 32 is not processed through an expensive fractionation column, but is passed directly to the adsorbent system 40.
  • the purified extract stream 42 is passed to an extract fractionation column 50 to separate the stream into a desorbent stream 52 and a normal paraffin product stream 54.
  • the desorbent stream 52 is re-used in both the adsorption separation unit 30 and the adsorbent system 40.
  • the normal paraffin product stream 54 has a heavy aromatic content of less than 0.5 wt%. Preferably, the process will be operated to reduce the heavy aromatic content to less than 100 ppm by weight.
  • the heavy aromatics include aromatic hydrocarbons having between 14 and 17 carbon atoms.
  • the adsorption units 40 eliminate the need for an extract fractionation column to separate the extract from the desorbent.
  • the extract stream 32 can be passed to a fractionation column before passing the extract stream to the adsorbent unit 40.
  • the desorbent is substantially removed from the extract stream 32, creating an extract stream with reduced desorbent content.
  • the extract stream with reduced desorbent content is passed to the adsorbent unit 40 and residual aromatics are removed.
  • the adsorption separation unit 30 also generates a raffinate stream 34 that includes the desorbent, non-normal paraffins and other hydrocarbons.
  • the raffinate stream 34 is passed to a raffinate fractionation column 60 to separate the raffinate stream 34 into a desorbent stream 62 and a bottoms stream 64 comprising non-normal paraffins, and other hydrocarbons.
  • the bottoms stream 64 can be passed to other processing units.
  • the desorbent stream 62 is re-used in the adsorption separation unit 30.
  • the adsorption separation system used for the continuous processing of hydrocarbons uses a simulated moving bed system, wherein the adsorption separation simulates the counter-current contact of a feedstream with an adsorbent.
  • the fluid flows down a column of beds, and the solid adsorbent moves up the column of beds.
  • the process has four zones: an adsorption zone where the feedstream contacts the adsorbent and selectively adsorbs the desired components thereby creating a raffinate stream; a purification zone where undesired components are flushed from the system to prevent contamination of the desorption zone; a desorption zone, where a liquid desorbent is added to displace the adsorbed component in the adsorbent beds thereby creating an extract stream; a buffer to prevent the contamination of liquid from desorption zone with the liquid in the adsorption zone. More information on the process is available in numerous patents and references, including US 5,912,395, which is incorporated by reference in its entirety.
  • the adsorption process in the present invention uses molecular sieving where the pores in the adsorbent are sized to allow for normal paraffins, but non-linear molecules are prevented from entering the pores.
  • the process of adsorbing heavy aromatics in the adsorbent unit 40 generates some light aromatics in the purified extract stream 42.
  • the light aromatics include aromatics in the C6 to C8 range, and are light components that are used in the regeneration of the adsorbent in the adsorbent unit 40.
  • the purified extract stream 42 when passed to the separation unit 50 includes in the overhead stream 52 light aromatics which can be re-used in the adsorbent unit 40.
  • the process is a continuous process, and can include two or more adsorbers in the heavy aromatic adsorbent units 40, where at least one adsorber is on-line and processing the extract stream 32, and one adsorber is off-line.
  • the regeneration process includes a first step of passing a stream 44 of purge material through the adsorbent unit 40.
  • the purge stream 46 is then passed to a fractionation unit 70.
  • a desorbent stream 48 is introduced to the adsorption unit 40.
  • a desorption stream which is separate from the purge stream 46 is generated carrying the heavy aromatic components to the fractionation unit 70.
  • the invention comprises six adsorbers in the adsorbent unit 40, with four of the adsorbers on-line, while a fifth adsorber is being purged and a sixth adsorber is being regenerated.
  • the process can include more or less adsorbers in the adsorption unit 40, depending on the size of the process streams.
  • the purge material can comprise a hydrocarbon stream having a different boiling point than the material in the C14 to C17 range.
  • a light material such as hydrocarbons in the C5 to CIO range is appropriate for displacing larger hydrocarbons left behind in the adsorbent unit 40.
  • a selection for the purge stream is a mixture of n-pentane and isooctane.
  • the adsorbent is selected to preferentially adsorb aromatic compounds.
  • the desorbent needs to be selected to displace the adsorbed aromatic compound, and to have a different boiling point from the adsorbed material.
  • a light aromatic compound in the C6 to C8 range is an appropriate choice.
  • para-xylene is selected for desorbing the heavy aromatics from the aromatics adsorption unit 40.
  • para-xylene is beneficial to the process, as para-xylene is also used in the adsorption separation unit 30, to purge material in the zone flush of the adsorption separation unit 30.
  • the choice of purge material for the aromatics adsorption unit 40 is the same as the desorbent mixture for use in the adsorption separation unit 30.
  • the process benefits by having the desorbent and purge materials do double duty in that the desorbent and purge materials are used in both adsorption units.
  • the fractionation unit 70 receives the purge stream 46 and the desorption stream which is separate from the purge stream 46 to separate the material recovered from the adsorption unit 40 during regeneration.
  • the separated streams include a first stream 72 comprising the purge material, a second stream 74 comprising the desorbent and a residual amount of the treated feedstream, and a third stream 76 comprising the heavy aromatics in the C14 to C17 range.
  • the heavy aromatics can be returned to the LGO process stream, or other process units.
  • the fractionation unit 70 can comprise a divided wall column or can comprise two separate columns.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

L'invention porte sur un procédé pour la production d'un courant de produit à base de paraffines normales purifiées. Le procédé comprend le passage d'un courant d'hydrocarbures comprenant les paraffines normales souhaitées dans un système de séparation par adsorption. Un courant de procédé produit à partir du système de séparation et comprenant les paraffines normales est amené à passer vers une unité d'adsorption pour l'adsorption sélective de composés aromatiques à partir du courant de procédé, ce qui produit de cette manière un produit purifié.
EP11851587.3A 2010-12-22 2011-12-09 Paraffines normales lourde de haute pureté utilisant des systèmes intégrés Withdrawn EP2655565A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12/976,295 US20120160742A1 (en) 2010-12-22 2010-12-22 High Purity Heavy Normal Paraffins Utilizing Integrated Systems
PCT/US2011/064142 WO2012087612A2 (fr) 2010-12-22 2011-12-09 Paraffines normales lourde de haute pureté utilisant des systèmes intégrés

Publications (1)

Publication Number Publication Date
EP2655565A2 true EP2655565A2 (fr) 2013-10-30

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP11851587.3A Withdrawn EP2655565A2 (fr) 2010-12-22 2011-12-09 Paraffines normales lourde de haute pureté utilisant des systèmes intégrés

Country Status (4)

Country Link
US (1) US20120160742A1 (fr)
EP (1) EP2655565A2 (fr)
CN (1) CN103261377A (fr)
WO (1) WO2012087612A2 (fr)

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WO2018083143A1 (fr) 2016-11-07 2018-05-11 Shell Internationale Research Maatschappij B.V. Processus de préparation de paraffines normales
WO2018083140A1 (fr) 2016-11-07 2018-05-11 Shell Internationale Research Maatschappij B.V. Composition de paraffine normale
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US10227533B2 (en) 2015-09-04 2019-03-12 Shell Oil Company Process to prepare paraffins and waxes
WO2018083149A1 (fr) 2016-11-07 2018-05-11 Shell Internationale Research Maatschappij B.V. Procédé de préparation de paraffines normales
WO2018083143A1 (fr) 2016-11-07 2018-05-11 Shell Internationale Research Maatschappij B.V. Processus de préparation de paraffines normales
WO2018083140A1 (fr) 2016-11-07 2018-05-11 Shell Internationale Research Maatschappij B.V. Composition de paraffine normale
US10934492B2 (en) 2016-11-07 2021-03-02 Shell Oil Company Process to prepare normal paraffins

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