EP2632879A2 - Procédé de production d'isomères de xylène purifiés - Google Patents

Procédé de production d'isomères de xylène purifiés

Info

Publication number
EP2632879A2
EP2632879A2 EP11836892.7A EP11836892A EP2632879A2 EP 2632879 A2 EP2632879 A2 EP 2632879A2 EP 11836892 A EP11836892 A EP 11836892A EP 2632879 A2 EP2632879 A2 EP 2632879A2
Authority
EP
European Patent Office
Prior art keywords
stream
unit
liquid phase
aromatics
product
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Withdrawn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
EP11836892.7A
Other languages
German (de)
English (en)
Other versions
EP2632879A4 (fr
Inventor
Dana Lynn Pilliod
John Di-Yi Ou
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.)
ExxonMobil Chemical Patents Inc
Original Assignee
ExxonMobil Chemical Patents Inc
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 ExxonMobil Chemical Patents Inc filed Critical ExxonMobil Chemical Patents Inc
Priority to EP11836892.7A priority Critical patent/EP2632879A4/fr
Publication of EP2632879A2 publication Critical patent/EP2632879A2/fr
Publication of EP2632879A4 publication Critical patent/EP2632879A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/067—C8H10 hydrocarbons
    • C07C15/08—Xylenes
    • 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
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
    • C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
    • 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
    • C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
    • C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/14—Purification; Separation; Use of additives by crystallisation; Purification or separation of the crystals

Definitions

  • the invention relates generally to the production of paraxylene and orthoxylene, including xylene isomerization, and also to an apparatus for the practice of said process.
  • the xylene isomers are important intermediates, which find wide and varied application in chemical syntheses.
  • paraxylene (PX) is a feedstock for terephthalic acid which finds use in the manufacture of synthetic fibers
  • metaxylene (MX) is used in the manufacture of dyes
  • orthoxylene (OX) is used as a feedstock for phthalic anhydride, which finds use in the manufacture of plasticizers.
  • Xylenes are found in various fractions, such as coal tar distillate, petroleum reformates, and pyrolysis liquids in admixture with other compounds of like boiling point.
  • the aromatic components are readily separated from non-aromatics by methods such as solvent extraction.
  • a fraction may then be obtained readily, such as by distillation, consisting essentially of C8 aromatics.
  • C8 aromatics aromatic hydrocarbons having 8 carbon atoms, including particularly ethylbenzene and the xylene isomers paraxylene (p- xylene or PX), orthoxylene (o-xylene or OX), and metaxylene (m-xylene or MX).
  • the feed streams to the system comprise C8+ aromatics and may come from one or more sources, including C8+ reformate 1 (see, for instance, U.S. Patent No. 7,179,367), C8+ Selective Toluene Disproportionation Product 17 (see, for instance, U.S. Patent Application Serial No. 12/042,433 now granted as U.S. Patent No. 7,989,672), C8+ transalkylation product 2 (see, for instance, U.S. Patent No. 7,663,010), C8+ toluene disproportionation product 15 (see, for instance, U.S. Patent No.
  • vapor phase xylenes isomerization 13 establishes a near- equilibrium balance of xylene isomers in stream 19 using one or more of a variety of catalysts, per se well-known in the art, which may also convert ethylbenzene to benzene and ethane or may convert ethylbenzene to near-equilibrium xylene isomers.
  • the xylenes isomerization product stream 19 passes to detoluenization fractionation 18 which removes C7 and lighter materials in stream 11 to yield isomerate recycle stream 10. Isomerate recycle stream 10 is processed in the OX and C9+ aromatics removal unit 16.
  • U.S. Patent No. 3,856,874 describes splitting the effluent stream from PX separation, passing the independent streams over different catalysts, then combining the isomerized streams and recycling.
  • U.S. Patent No. 7,439,412 teaches a process for recovering one or more high purity xylene isomers from a C8+ aromatic feedstream including the use of an isomerization unit under liquid phase conditions.
  • the product of the liquid phase isomerization unit is returned to the first fractionation tower in the system. See also U.S. Patent No. 7,626,065.
  • U.S. Patent No. 7,553,998 teaches a process for recovering one or more high- purity xylene isomers from a feed having substantial content of C9+ aromatic hydrocarbons comprising de-ethylation of heavy aromatics followed by fractionation and then passing the stream to a C8 aromatic isomer recovery to recover high-purity xylene isomer with lowered energy costs.
  • Streams passing through an isomerization unit under liquid isomerization conditions are split, with a portion sent to an isomer recovery unit, and a portion is purged.
  • U.S. Application Serial No. 12/612,007 (published as 2010/0152508) describes a process for producing a PX-rich product, the process comprising: (a) providing a PX-depleted stream; (b) isomerizing at least a portion of the PX-depleted stream to produce an isomerized stream having a PX concentration greater than the PX-depleted stream, a benzene concentration of less than 1,000 ppm, and a C9+ hydrocarbons concentration of less than 5,000 ppm; and (c) separating the isomerized stream by selective adsorption.
  • Provisional Application No. 61/326,445, filed April 21, 2010, is directed to a xylenes isomerization process, including a liquid phase isomerization, for the production of equilibrium or near-equilibrium xylenes, wherein the process conditions include a temperature of less than 295°C and a pressure sufficient to maintain the xylenes in liquid phase that uses at most only ppm levels of hydrogen and that in embodiments can be regenerated numerous times by a very simple in situ procedure.
  • the invention is directed to a process for producing paraxylene comprising first separating a feed comprising C8+ aromatics into an overhead, or first stream comprising PX and MX and a bottoms product, or second stream comprising OX and C9+ aromatics, separating the PX and MX stream in a PX recovery unit to recover a PX-rich stream and a PX-depleted stream, then separating said PX depleted (C8 aromatics) stream through a parallel configuration of vapor phase xylenes isomerization and liquid phase xylenes isomerization.
  • the OX and C9+ aromatics stream may then be separated downstream of the first separating step, such as by fractionation.
  • a benzene separation step occurs between the first fractionation and the PX recovery unit, and/or a benzene separation step downstream from the isomerization step(s). There may also be, in embodiments, a toluene separation step, such as downstream of said isomerization step(s).
  • the liquid phase isomerization product is recycled to one or more of the first fractionation step, the benzene separation step (where present), and the PX recovery step.
  • the invention also relates to an apparatus for the production of paraxylene comprising a first fractionation column operating at conditions suitable for the separation of a C8+ aromatics stream into an overheads comprising PX and MX, and a bottoms product comprising OX and C9+ aromatics.
  • the overheads stream fluidly connected with a PX recovery unit, wherein said PX recovery unit provides a PX-enriched stream, a PX-depleted stream, and the bottoms product stream is fluidly connected with an OX/C9+ separation step.
  • the improvement comprising dividing a conduit carrying said PX-depleted stream so that a portion of said PX-depleted stream is passed to a vapor phase isomerization unit, and another portion of said PX-depleted stream is passed to a liquid phase isomerization unit.
  • said liquid phase isomerization unit is fluidly connected so as to provide liquid phase isomerate recycle to said first fractionation column and/or to said PX recovery unit.
  • said PX recovery unit is selected from at least one of a crystallizer and an adsorptive separator.
  • At least one other fractionator upstream of said first fractionator, wherein said at least one other fractionator operates under conditions suitable for removing benzene from a stream comprising xylenes or for removing toluene from a stream comprising xylenes, and optionally wherein both said fractionator for removing benzene and said fractionator for removing toluene are provided upstream of said first fractionator.
  • Figure 1 is a schematic illustrating typical commercial processing of C8+ aromatics to produce paraxylene.
  • Figure 2 is a schematic illustrating an embodiment of the invention.
  • Figures 3 and 4 represent a comparison of two systems, the former returning liquid isomerization product to the rerun tower and the latter returning liquid isomerization product to PX recovery unit.
  • a system having parallel configuration of vapor phase and liquid phase isomerization units. This configuration significantly reduces energy consumption by minimizing the amount of isomerate recycle from the vapor phase xylene isomerization and controlling the amount of C9+ aromatics that are processed in the OX and C9+ aromatics removal and subsequent OX recovery.
  • Figure 2 illustrates a specific embodiment of the invention. It will be understood by one of skill in the art that Figure 2 is merely representative of the present invention and that many variations thereof can be readily envisioned. Moreover, various valves, compressors, and the like are not shown for convenience of view but would also be readily apparent to one of skill in the art.
  • fractionator 16 As shown in Figure 2, various feed sources comprising C8+ aromatic hydrocarbons, such as 1, 2, 15, and 17, as identified above, are sent to fractionator 16, which removes C9+ aromatics and substantially all OX from the feed.
  • the lights are sent overhead to PX recovery 12 with intermediate removal of benzene purge 22 in fractionator 23.
  • the overhead is sent via line 6 to PX recovery, which may be provided by a crystallization unit or selective adsorption unit (such as a Parex unit), per se known in the art.
  • PX is taken off in line 7 and the PX-depleted stream comprising C8 aromatics is split and sent in parallel to vapor phase xylenes isomerization 13, having a source of hydrogen 9, and liquid phase xylene isomerization 20 via lines 30 and 40, respectively.
  • Isomerate recycle 10 from vapor phase xylenes isomerization 13 is decreased by this process scheme and the amount of C9+ aromatics that are processed in the OX and C9+ aromatics removal 16 is better controlled.
  • the flow of PX-depleted C8 aromatics 8 is minimized through vapor phase xylenes isomerization 13 to minimize energy by reducing the amount of PX-depleted C8 aromatics stream 8 that is vaporized in vapor phase xylenes isomerization 13 and the associated amount of isomerate recycle stream 10 which contains a much higher concentration of by-product C9+ aromatics than liquid phase xylenes isomerization product 21.
  • the vapor phase isomerate in conduit 19 is passed through detoluenization fractionation 18, which removes C7 and lighter materials (C7-) in stream 11 to yield isomerate recycle stream 10.
  • Liquid phase isomerate recycle stream 21 which is the product from liquid phase xylenes isomerization 20 is sent to OX and C9+ aromatics removal 16 at a higher feed location in the column so as to minimize energy consumption due to its lower concentration of C9+ aromatics.
  • the product from the liquid phase isomerization can be sent via conduit 50 to benzene removal fractionator 23 as shown in Figure 2, and/or directly back to PX recovery via conduit 60.
  • the amount of energy savings on the OX and C9+ aromatics removal 16 and the subsequent OX fractionation 14 can result in as much as a 75% reduction in the overall energy consumption of the process for the production of PX and OX.
  • the bottoms product 3 from fractionator 16 may be advantageously fractionated in 14 to yield an overheads product 4 of OX and bottoms product of C9+ aromatic hydrocarbons.
  • FIG. 2 also shows that the liquid phase isomerate recycle stream 21 can be optionally sent to one or more locations which include OX and C9+ aromatics removal 16, benzene removal 23, and directly to PX recovery 12.
  • the amount sent to each location is determined by the need to remove by-products which include benzene, and C9+ aromatics.
  • the by-products from liquid phase xylenes isomerization 20 in the liquid phase isomerate recycle stream 21 may need to be removed down to a level that is acceptable for PX recovery 12 especially if selective adsorption is used for recovering paraxylene.
  • the C9+ aromatics can be removed in the OX and C9+ aromatics removal 16 or in one or more devices that employ separation techniques such as membrane, extraction, and adsorption.
  • benzene can be removed using one or more devices that employ separation techniques such as distillation, extraction, membrane, and adsorption.
  • separation techniques such as distillation, extraction, membrane, and adsorption.
  • the C9+ aromatics and benzene can be removed simultaneously using one or more devices that employ separation techniques such as distillation, extraction, membrane, and adsorption.
  • Process A ( Figure 3) sent the product from the liquid phase isomerization unit 20 to the rerun tower 16, while Process B ( Figure 4) sent the product to the Parex unit 12.
  • the vapor phase isomerate from vapor phase isomerization unit 13 is passed through detoluenization fractionator 18 in the same manner and to the same effect as in Figures 1 and 2, and the equilibrium or near equilibrium xylene isomerate sent back to the rerun tower 16.
  • the simulations show that using the process according to the invention, there are significant energy savings of 13.10 MW (mega Watts) for Process B ( Figure 4), and 12.45 MW for Process A ( Figure 3), compared to the base case of Figure 1.
  • this invention relates to:
  • a process for producing paraxylene comprising:
  • an apparatus for the production of paraxylene (PX) and orthoxylene (OX) comprising a first fractionation column operating at conditions suitable for the separation of a C8+ aromatics stream into an overheads comprising PX and metaxylene (MX) and a bottoms product stream comprising OX and C9+ aromatics, the overheads stream fluidly connected with a PX recovery unit, wherein said PX recovery unit provides a PX-enriched stream and a PX-depleted stream, the improvement comprising dividing a conduit carrying said PX- depleted stream so that a portion of said PX-depleted stream is passed to a vapor phase isomerization unit and another portion of said PX-depleted stream is passed to a liquid phase isomerization unit.
  • PX paraxylene
  • OX orthoxylene
  • liquid phase isomerization unit is fluidly connected so as to provide liquid phase isomerate recycle to said first fractionation column and/or to said PX recovery unit.
  • Trade names used herein are indicated by aTM symbol or ® symbol, indicating that the names may be protected by certain trademark rights, e.g., they may be registered trademarks in various jurisdictions. All patents and patent applications, test procedures (such as priority documents, ASTM methods, UL methods, and the like), and other documents cited herein are fully incorporated by reference to the extent such disclosure is not inconsistent with this invention and for all jurisdictions in which such incorporation is permitted. When numerical lower limits and numerical upper limits are listed herein, ranges from any lower limit to any upper limit are contemplated.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production de paraxylène et d'orthoxylène, consistant à réduire la quantité d'isomérat à recycler provenant de l'isomérisation de xylènes en phase vapeur, par utilisation d'un agencement parallèle d'unités d'isomérisation en phase vapeur et en phase liquide.
EP11836892.7A 2010-10-29 2011-10-21 Procédé de production d'isomères de xylène purifiés Withdrawn EP2632879A4 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11836892.7A EP2632879A4 (fr) 2010-10-29 2011-10-21 Procédé de production d'isomères de xylène purifiés

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US40808110P 2010-10-29 2010-10-29
EP10192324 2010-11-24
PCT/US2011/057226 WO2012058106A2 (fr) 2010-10-29 2011-10-21 Procédé de production d'isomères de xylène purifiés
EP11836892.7A EP2632879A4 (fr) 2010-10-29 2011-10-21 Procédé de production d'isomères de xylène purifiés

Publications (2)

Publication Number Publication Date
EP2632879A2 true EP2632879A2 (fr) 2013-09-04
EP2632879A4 EP2632879A4 (fr) 2015-12-16

Family

ID=43247470

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11836892.7A Withdrawn EP2632879A4 (fr) 2010-10-29 2011-10-21 Procédé de production d'isomères de xylène purifiés

Country Status (6)

Country Link
EP (1) EP2632879A4 (fr)
JP (1) JP5745635B2 (fr)
KR (1) KR101530139B1 (fr)
CN (1) CN103201241A (fr)
SG (1) SG189199A1 (fr)
WO (1) WO2012058106A2 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG10201508779UA (en) * 2010-10-29 2015-11-27 Exxonmobil Chem Patents Inc Process for the production of paraxylene
WO2014085178A1 (fr) 2012-11-30 2014-06-05 Exxonmobil Chemical Patents Inc. Procédés à haut rendement énergétique pour la production de xylènes
US9309169B2 (en) 2012-11-30 2016-04-12 Exxonmobil Chemical Patents Inc. Process for the production of purified xylene isomers
US9266796B2 (en) * 2013-09-27 2016-02-23 Uop Llc Systems and methods for producing desired xylene isomers
KR102319222B1 (ko) * 2014-02-13 2021-10-28 비피 코포레이션 노쓰 아메리카 인코포레이티드 Tol/a9+ 알킬 교환반응 프로세스들로부터 반응기 유출물을 분리하기 위한 에너지 효율적 분별 프로세스
FR3023842B1 (fr) * 2014-07-18 2017-11-24 Ifp Energies Now Procede de production de paraxylene a haute purete a partir d'une coupe xylene, procede utilisant une unite de separation en lit mobile simule et deux unites d'isomerisation, l'une en phase gaz l'autre en phase liquide.
TW201733664A (zh) * 2015-11-13 2017-10-01 艾克頌美孚研究工程公司 烴逆滲透膜及分離
CN110283033B (zh) * 2019-06-28 2021-11-02 中国石油天然气集团有限公司 多区协控微循环高容量吸附结晶耦合芳烃生产方法及系统
WO2023044278A1 (fr) * 2021-09-16 2023-03-23 Exxonmobil Chemical Patents Inc. Procédés de séparation d'isomères de xylène
CN114534771B (zh) * 2022-03-03 2022-09-16 大庆亿鑫化工股份有限公司 一种混合二甲苯的异构化催化剂和邻二甲苯的分离方法
WO2023244389A1 (fr) * 2022-06-14 2023-12-21 Exxonmobil Chemical Patents Inc. Production de p-xylène par isomérisation en phase liquide en présence d'hydrocarbures aromatiques en c9+ et séparation de ceux-ci

Family Cites Families (12)

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Publication number Priority date Publication date Assignee Title
US3856874A (en) * 1973-09-13 1974-12-24 Mobil Oil Corp Xylene isomerization
US4236996A (en) * 1979-05-25 1980-12-02 Mobil Oil Corporation Xylene isomerization
US5705726A (en) * 1994-11-18 1998-01-06 Mobil Oil Corporation Xylene isomerization on separate reactors
US5998688A (en) * 1998-08-25 1999-12-07 Mobil Oil Corporation Xylene isomerization process using toluene co-feed
BR9913240A (pt) * 1998-08-25 2001-05-15 Mobil Oil Corp Processo de produção de para-xileno
FR2792632B1 (fr) * 1999-04-22 2004-02-13 Inst Francais Du Petrole Procede de production de paraxylene comprenant une etape d'adsorption, une etape d'isomerisation en phase liquide et une etape d'isomerisation en phase gazeuse avec une zeolithe de type eu0
FR2844790B1 (fr) * 2002-09-20 2004-10-22 Inst Francais Du Petrole Procede de coproduction de paraxylene et de styrene
FR2862638B1 (fr) * 2003-11-26 2005-12-30 Inst Francais Du Petrole Procede de production de paraxylene comprenant une etape d'adsorption et deux etapes d'isomerisation
FR2883283B1 (fr) * 2005-03-16 2007-05-18 Inst Francais Du Petrole Procede de production combinee de paraxylene et de benzene de productivite amelioree
BRPI0710917A2 (pt) * 2006-04-25 2012-02-22 Exxonmobil Chemical Patents Inc processo para a produção de um produto e de uma corrente ricos em para -xileno
KR100843435B1 (ko) * 2007-04-27 2008-07-03 삼성토탈 주식회사 유사 이동층 크실렌 혼합물 전처리 공정 및 추가의 크실렌이성질화 공정을 포함하는 방향족 화합물의 분리 방법
SG10201508779UA (en) * 2010-10-29 2015-11-27 Exxonmobil Chem Patents Inc Process for the production of paraxylene

Also Published As

Publication number Publication date
WO2012058106A3 (fr) 2012-07-05
CN103201241A (zh) 2013-07-10
WO2012058106A2 (fr) 2012-05-03
JP5745635B2 (ja) 2015-07-08
KR101530139B1 (ko) 2015-06-18
KR20130091345A (ko) 2013-08-16
EP2632879A4 (fr) 2015-12-16
SG189199A1 (en) 2013-05-31
JP2014501700A (ja) 2014-01-23

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