EP2632879A2 - Process for the production of purified xylene isomers - Google Patents
Process for the production of purified xylene isomersInfo
- 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- Withdrawn
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.
Landscapes
- 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
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11836892.7A EP2632879A4 (en) | 2010-10-29 | 2011-10-21 | Process for the production of purified xylene isomers |
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 (en) | 2010-10-29 | 2011-10-21 | Process for the production of purified xylene isomers |
EP11836892.7A EP2632879A4 (en) | 2010-10-29 | 2011-10-21 | Process for the production of purified xylene isomers |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2632879A2 true EP2632879A2 (en) | 2013-09-04 |
EP2632879A4 EP2632879A4 (en) | 2015-12-16 |
Family
ID=43247470
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP11836892.7A Withdrawn EP2632879A4 (en) | 2010-10-29 | 2011-10-21 | Process for the production of purified xylene isomers |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP2632879A4 (en) |
JP (1) | JP5745635B2 (en) |
KR (1) | KR101530139B1 (en) |
CN (1) | CN103201241A (en) |
SG (1) | SG189199A1 (en) |
WO (1) | WO2012058106A2 (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SG189261A1 (en) * | 2010-10-29 | 2013-05-31 | Exxonmobil Chem Patents Inc | Process for the production of paraxylene |
US9309169B2 (en) | 2012-11-30 | 2016-04-12 | Exxonmobil Chemical Patents Inc. | Process for the production of purified xylene isomers |
CN104870409A (en) * | 2012-11-30 | 2015-08-26 | 埃克森美孚化学专利公司 | Energy efficient processes for xylenes production |
US9266796B2 (en) * | 2013-09-27 | 2016-02-23 | Uop Llc | Systems and methods for producing desired xylene isomers |
ES2749869T3 (en) * | 2014-02-13 | 2020-03-24 | Bp Corp North America Inc | Energy efficient fractionation procedure to separate reactor effluent from TOL / a9 + transalkylation procedures |
FR3023842B1 (en) * | 2014-07-18 | 2017-11-24 | Ifp Energies Now | PROCESS FOR PRODUCING HIGH PURITY PARAXYLENE FROM XYLENE CUT, METHOD USING SIMUL MOBILE BED SEPARATION UNIT AND TWO ISOMERIZING UNITS, ONE IN GAS PHASE AND THE OTHER IN LIQUID PHASE. |
TW201733915A (en) * | 2015-11-13 | 2017-10-01 | 艾克頌美孚研究工程公司 | Reverse osmosis membranes and separations |
CN110283033B (en) * | 2019-06-28 | 2021-11-02 | 中国石油天然气集团有限公司 | Multi-region coordinated control microcirculation high-capacity adsorption crystallization coupled aromatic hydrocarbon production method and system |
WO2023044278A1 (en) * | 2021-09-16 | 2023-03-23 | Exxonmobil Chemical Patents Inc. | Xylene isomer separation processes |
CN114534771B (en) * | 2022-03-03 | 2022-09-16 | 大庆亿鑫化工股份有限公司 | Isomerization catalyst for mixed xylene and separation method of o-xylene |
WO2023244389A1 (en) * | 2022-06-14 | 2023-12-21 | Exxonmobil Chemical Patents Inc. | Production of p-xylene by liquid-phase isomerization in the presence of c9+ aromatic hydrocarbons and separation thereof |
Family Cites Families (12)
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 |
BR9913240A (en) * | 1998-08-25 | 2001-05-15 | Mobil Oil Corp | Para-xylene production process |
US5998688A (en) * | 1998-08-25 | 1999-12-07 | Mobil Oil Corporation | Xylene isomerization process using toluene co-feed |
FR2792632B1 (en) * | 1999-04-22 | 2004-02-13 | Inst Francais Du Petrole | PROCESS FOR THE PRODUCTION OF PARAXYLENE INCLUDING AN ADSORPTION STAGE, A LIQUID PHASE ISOMERIZATION STAGE AND A GAS PHASE ISOMERIZATION STAGE WITH A ZEOLITH OF EU0 TYPE |
FR2844790B1 (en) * | 2002-09-20 | 2004-10-22 | Inst Francais Du Petrole | PARAXYLENE AND STYRENE CO-PRODUCTION PROCESS |
FR2862638B1 (en) * | 2003-11-26 | 2005-12-30 | Inst Francais Du Petrole | PROCESS FOR THE PRODUCTION OF PARAXYLENE COMPRISING AN ADSORPTION STEP AND TWO STEPS OF ISOMERIZATION |
FR2883283B1 (en) * | 2005-03-16 | 2007-05-18 | Inst Francais Du Petrole | PROCESS FOR COMBINED PRODUCTION OF PARAXYLENE AND BENZENE OF ENHANCED PRODUCTIVITY |
WO2007127049A2 (en) * | 2006-04-25 | 2007-11-08 | Exxonmobil Chemical Patents Inc. | Process for producing para-xylene |
KR100843435B1 (en) * | 2007-04-27 | 2008-07-03 | 삼성토탈 주식회사 | A separation method of aromatic compounds comprising simulated moving bed xylene mixture pre-treatment process and additional xylene isomerization process |
SG189261A1 (en) * | 2010-10-29 | 2013-05-31 | Exxonmobil Chem Patents Inc | Process for the production of paraxylene |
-
2011
- 2011-10-21 WO PCT/US2011/057226 patent/WO2012058106A2/en active Application Filing
- 2011-10-21 SG SG2013024104A patent/SG189199A1/en unknown
- 2011-10-21 CN CN2011800523988A patent/CN103201241A/en active Pending
- 2011-10-21 EP EP11836892.7A patent/EP2632879A4/en not_active Withdrawn
- 2011-10-21 JP JP2013535109A patent/JP5745635B2/en not_active Expired - Fee Related
- 2011-10-21 KR KR1020137010668A patent/KR101530139B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP2632879A4 (en) | 2015-12-16 |
KR20130091345A (en) | 2013-08-16 |
JP2014501700A (en) | 2014-01-23 |
WO2012058106A2 (en) | 2012-05-03 |
SG189199A1 (en) | 2013-05-31 |
JP5745635B2 (en) | 2015-07-08 |
WO2012058106A3 (en) | 2012-07-05 |
KR101530139B1 (en) | 2015-06-18 |
CN103201241A (en) | 2013-07-10 |
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Ipc: C07C 7/14 20060101ALI20151110BHEP Ipc: C07C 15/08 20060101ALI20151110BHEP Ipc: C07C 7/13 20060101ALI20151110BHEP Ipc: C07C 5/27 20060101AFI20151110BHEP Ipc: C07C 7/00 20060101ALI20151110BHEP |
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