US20040218547A1 - Process modification to maximize benzene production - Google Patents

Process modification to maximize benzene production Download PDF

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Publication number
US20040218547A1
US20040218547A1 US10/425,650 US42565003A US2004218547A1 US 20040218547 A1 US20040218547 A1 US 20040218547A1 US 42565003 A US42565003 A US 42565003A US 2004218547 A1 US2004218547 A1 US 2004218547A1
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United States
Prior art keywords
benzene
precursors
aromatics
reformer
toluene
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Abandoned
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US10/425,650
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English (en)
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William Rhodey
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Individual
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Priority to US10/425,650 priority Critical patent/US20040218547A1/en
Priority to CA2465465A priority patent/CA2465465C/fr
Publication of US20040218547A1 publication Critical patent/US20040218547A1/en
Priority to US11/701,931 priority patent/US8889943B2/en
Priority to US14/543,117 priority patent/US9611190B2/en
Priority to US15/436,025 priority patent/US10113123B2/en
Abandoned legal-status Critical Current

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    • 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
    • C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
    • C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
    • C10G69/08—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one step of reforming naphtha
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
    • C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
    • C01B3/32—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air
    • C01B3/34—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/367—Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
    • C07C5/393—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation with cyclisation to an aromatic six-membered ring, e.g. dehydrogenation of n-hexane to benzene
    • C07C5/41—Catalytic processes
    • C07C5/415—Catalytic processes with metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
    • C07C5/393—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation with cyclisation to an aromatic six-membered ring, e.g. dehydrogenation of n-hexane to benzene
    • C07C5/41—Catalytic processes
    • C07C5/415—Catalytic processes with metals
    • C07C5/417—Catalytic processes with metals of the platinum group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/005—Processes comprising at least two steps in series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
    • C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/064—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing iron group metals, noble metals or copper
    • C07C2529/068—Noble metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/076—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • 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

  • This invention relates to a new concept to maximize benzene production using refinery and aromatics extraction processes in a unique operating sequence and mode tailored to maximize the amount of benzene produced and minimize the operating and capital costs to produce benzene.
  • refinery aromatics are produced from a naphtha reformer unit.
  • the naphtha reformer produces aromatics including benzene, toluene and xylenes in various concentrations.
  • An aromatics extraction unit recovers aromatics either from the whole reformate stream or a fractionated portion of reformate. Both benzene and a portion of the xylenes, para-xylene, can be used directly in the production of petrochemical derivatives.
  • Toluene on the other hand has a limited market in terms of petrochemical derivatives and TNT precursors.
  • toluene and xylenes are processed in a hydro-dealkylation unit at a considerable cost and production of low value fuel gas from an expensive feedstock to produce additional benzene.
  • toluene can be processed in a toluene disproportioning unit to benzene and lower value products.
  • a direct route to benzene from benzene precursors is more cost effective in these times of competitive commodity business and minimization of costs.
  • the genesis of this process idea is to fractionate benzene precursors from the naphtha feed to the naphtha reformer and also collect benzene precursors from condensate or natural gasoline utilizing extractive distillation and feed the resulting concentrated benzene precursor stream to a specified low severity high yield naphtha reformer. At the same time, recover the hydrogen co-product to hydrotreat the condensate and benzene precursor concentrated stream.
  • the cost of this process is substantially lower than that of a reformer at high severity to yield BTX aromatics and meet the gasoline octane specification.
  • High severity reforming results in a significant volume loss across the naphtha reformer and may crack some benzene precursors to lower value products.
  • the toluene and xylenes produced in the reformer need to be processed in a high cost hydro-dealkyation unit to produce benzene or feed toluene to a toluene disproportioning unit to produce benzene.
  • Another option envisaged by this process idea is to not only concentrate die benzene precursors but also the xylene precursors prior to the naphtha reformer. Additional xylene precursors would originate from condensate or other refinery streams high in benzene and xylene precursors. In this mode of operation, the naphtha reformer will produce xylenes for the para xylenes market.
  • the normal refinery configuration is shown on the figure labelled “Present Refinery Configuration”.
  • Crude can be a combination of crudes and intermediate refinery feedstocks resembling crude oil.
  • the overheads for the crude unit whole range naphtha, is processed in a naphtha splitter producing an overhead stream normally called Light Straight Run or LSR and a bottoms stream of heavy naphtha.
  • This material after hydrotreating to remove Sulphur, along with other intermediate refinery sweet naphtha streams is fed to a naphtha reformer.
  • the purpose of the naphtha reformer is to produce re-formulate naphtha components in to those that constitute gasoline product.
  • these are aromatics including benzene, toluene and xylenes as well as other aromatics that allow this product; reformate, to have an octane quality sufficient to meet gasoline octane specifications.
  • reformate to have an octane quality sufficient to meet gasoline octane specifications.
  • the proper boiling point and all the gasoline specifications are met by blending LSR and reformate and other gasoline components such as butane, alkylate, methyl tertiary butyl ether, ethanol and catalytic cracker gasoline.
  • reformate is processed in an aromatics extraction process of which there are two basic types, solvent and extractive distillation.
  • the aromatics consisting of benzene, toluene and xylenes are further fractionated usually into benzene and a toluene/xylene mix.
  • Additional benzene can be produced from toluene and xylenes by hydro de-alkylation and/or toluene disproportioning.
  • the xylenes can be further processed to obtain para and ortho xylene for other petrochemical derivative production. Producing benzene from these two processes introduces additional capital and loss of expensive feedstock to lower value fuel gas and hydrogen if there is a need.
  • the reformer normally produces benzene and control of benzene in the gasoline can be accommodated by the extraction of benzene in the aromatics extraction unit as detailed above. There are 3 other ways to control the benzene production:
  • a process to maximize benzene production is shown in the figure “Modified Refinery Configuration”.
  • the process does not have to be in a refinery setting but may be a “stand alone” benzene producer and/or a benzene precursor concentrator feeding an existing refinery; the splitter, hydrotreater aromatics extraction/fractionation, and specific reformer would constitute an “off site” plant.
  • the refinery scheme would be modified to split naphtha into a C6+ bottoms product and C5 top product.
  • the process involves recovering C6 components from the hydrotreater as a separate stream and routing them to the aromatics extraction process.
  • the remainder of the hydrotreated naphtha is routed to the reformer to produce gasoline.
  • the light gasoline components are routed to the hydrotreater and the C6s are routed to the aromatics extraction process to recover aromatics comprised of predominately benzene with some small amounts of toluene and xylenes.
  • a further stream of benzene rich condensate or natural gasoline is routed to the naphtha splitter.
  • This material is typically composed of C4-C7s having the majority of components in the C5-C6 ranges.
  • the stream contains a high proportion of benzene precursors notably methyl cyclo pentane and cyclohexanes.
  • a separate low sulphur condensate containing no sulphur components and usually a stream from a refinery that is rich in benzene can be processed in the modified refinery. It is usually light reformate as produced in a normal refinery configuration but originating from a refinery or process that has no benzene removal or saturation process. This material can be directed to the aromatics extraction unit to be treated in a smaller fashion to other benzene rich streams.
  • the aromatics extraction unit is basically an extractive distillation of benzene that does not recover the benzene precursors with the benzene steam. Small amounts of toluene and xylenes contained in the feed would be recovered as gasoline components.
  • This material can be fractionated from the remaining components by distillation. This material will be routed to a second smaller reformer whose only function is to produce benzene from a stream high in benzene precursors. The benzene product is routed to the same aromatics extraction process to recover additional benzene.
  • Precursors not refined to aromatics are recycled to this reformer by the C6 distillation of the raffinate stream in the aromatics extraction process.
  • a sulphur guard bed may be required to remove traces of sulphur prior to reforming or the stream may be recycled to the hydrotreater.
  • Monitoring of the reformer would be undertaken to note whether the amount of C6's are increasing significantly. If so, a slipstream of this material would be routed to the gasoline pool.
  • the operation of the second reformer would be optimized to produce benzene. Production of toluene and xylenes would be minimized. Severity and feedstock variables would be monitored to meet the criteria of maximum benzene production. Older reformer technology may be utilized in this reformer, as the objective is benzene production. It is also assumed that the specific market location may not need other aromatics such as toluene and xylenes.
  • the C5s and the C6s leaving a boiling range including iso hexanes and lighter could be routed directly to the gasoline pool.
  • the remaining C6s and C7 to C11s could be routed directly to the aromatics extraction unit rather than a reformer unit to recover all the aromatics from the naphtha fraction.
  • a separate splitter can be built on the condensate stream that could be designed to handle a stream of C6's as overheads and C8's as the bottom product.
  • This combined material would be routed after hydrotreating to the aromatics extraction process to recover benzene and xylenes.
  • the resulting raffinate stream would be routed to the gasoline pool to meet the octane specification of gasoline.
  • the mid stream C7's would be routed to the primary reformer. In this way, the benzene precursors are concentrated as in the modified refinery configuration and the aromatics extaction unit can recover the naturally occurring xylenes.
  • the xylene precursors could be recovered after the aromatics extraction unit to be processed in the primary reformer to produce additional xylenes.
  • the modified process configuration does not include toluene and xylenes feedstock processes to produce additional benzene. These processes are costly and produce products of lower value.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Water Supply & Treatment (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Inorganic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US10/425,650 2003-04-30 2003-04-30 Process modification to maximize benzene production Abandoned US20040218547A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US10/425,650 US20040218547A1 (en) 2003-04-30 2003-04-30 Process modification to maximize benzene production
CA2465465A CA2465465C (fr) 2003-04-30 2004-04-28 Modification d'une methode de production de benzene visant a en maximiser le rendement
US11/701,931 US8889943B2 (en) 2003-04-30 2007-02-02 Process and system for extraction of a feedstock
US14/543,117 US9611190B2 (en) 2003-04-30 2014-11-17 Process and system for extraction of a feedstock
US15/436,025 US10113123B2 (en) 2003-04-30 2017-02-17 Process and system for extraction of a feedstock

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10/425,650 US20040218547A1 (en) 2003-04-30 2003-04-30 Process modification to maximize benzene production

Related Child Applications (2)

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US11/701,931 Continuation US8889943B2 (en) 2003-04-30 2007-02-02 Process and system for extraction of a feedstock
US11/701,931 Continuation-In-Part US8889943B2 (en) 2003-04-30 2007-02-02 Process and system for extraction of a feedstock

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US20040218547A1 true US20040218547A1 (en) 2004-11-04

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US10/425,650 Abandoned US20040218547A1 (en) 2003-04-30 2003-04-30 Process modification to maximize benzene production
US11/701,931 Expired - Fee Related US8889943B2 (en) 2003-04-30 2007-02-02 Process and system for extraction of a feedstock
US14/543,117 Expired - Lifetime US9611190B2 (en) 2003-04-30 2014-11-17 Process and system for extraction of a feedstock
US15/436,025 Expired - Fee Related US10113123B2 (en) 2003-04-30 2017-02-17 Process and system for extraction of a feedstock

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US11/701,931 Expired - Fee Related US8889943B2 (en) 2003-04-30 2007-02-02 Process and system for extraction of a feedstock
US14/543,117 Expired - Lifetime US9611190B2 (en) 2003-04-30 2014-11-17 Process and system for extraction of a feedstock
US15/436,025 Expired - Fee Related US10113123B2 (en) 2003-04-30 2017-02-17 Process and system for extraction of a feedstock

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2149594A1 (fr) * 2008-07-28 2010-02-03 Mohammadreza Pircheraghali Production d'essence selon un nouveau procédé mélangeant des découpes de matériaux de pétrole
US8889943B2 (en) 2003-04-30 2014-11-18 William George Rhodey Process and system for extraction of a feedstock
US11046898B1 (en) * 2020-05-15 2021-06-29 Saudi Arabian Oil Company Systems and processes for separating and upgrading hydrocarbons integrating a refinery system with steam cracking of an aromatic bottoms stream

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8926830B2 (en) 2011-04-29 2015-01-06 Uop Llc Process for increasing aromatics production
US9150467B2 (en) * 2013-07-23 2015-10-06 Uop Llc Processes and apparatuses for preparing aromatic compounds

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8889943B2 (en) 2003-04-30 2014-11-18 William George Rhodey Process and system for extraction of a feedstock
US9611190B2 (en) 2003-04-30 2017-04-04 William George Rhodey Process and system for extraction of a feedstock
US10113123B2 (en) 2003-04-30 2018-10-30 William George Rhodey Process and system for extraction of a feedstock
EP2149594A1 (fr) * 2008-07-28 2010-02-03 Mohammadreza Pircheraghali Production d'essence selon un nouveau procédé mélangeant des découpes de matériaux de pétrole
WO2010012985A1 (fr) * 2008-07-28 2010-02-04 Smyth, Gyles Darren Production d’essence utilisant un nouveau procédé, mélange de fractions de matières de pétrole
US11046898B1 (en) * 2020-05-15 2021-06-29 Saudi Arabian Oil Company Systems and processes for separating and upgrading hydrocarbons integrating a refinery system with steam cracking of an aromatic bottoms stream

Also Published As

Publication number Publication date
US10113123B2 (en) 2018-10-30
US20170158974A1 (en) 2017-06-08
US9611190B2 (en) 2017-04-04
US20150071850A1 (en) 2015-03-12
CA2465465C (fr) 2013-08-13
US20070129590A1 (en) 2007-06-07
US8889943B2 (en) 2014-11-18
CA2465465A1 (fr) 2004-10-30

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