WO2010059317A2 - Procédé de séparation - Google Patents

Procédé de séparation Download PDF

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Publication number
WO2010059317A2
WO2010059317A2 PCT/US2009/060833 US2009060833W WO2010059317A2 WO 2010059317 A2 WO2010059317 A2 WO 2010059317A2 US 2009060833 W US2009060833 W US 2009060833W WO 2010059317 A2 WO2010059317 A2 WO 2010059317A2
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WO
WIPO (PCT)
Prior art keywords
compound
feedstream
concentration
modified
distributive
Prior art date
Application number
PCT/US2009/060833
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English (en)
Other versions
WO2010059317A3 (fr
Inventor
John R. Porter
Dana L. Pilliod
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 KR1020117014022A priority Critical patent/KR101362490B1/ko
Priority to CN2009801458103A priority patent/CN102215930A/zh
Priority to JP2011536366A priority patent/JP5662938B2/ja
Priority to EP09827944.1A priority patent/EP2364192A4/fr
Publication of WO2010059317A2 publication Critical patent/WO2010059317A2/fr
Publication of WO2010059317A3 publication Critical patent/WO2010059317A3/fr

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Classifications

    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/02—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor with moving adsorbents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
    • B01D15/1814—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns recycling of the fraction to be distributed
    • B01D15/1821—Simulated moving beds
    • B01D15/1828—Simulated moving beds characterized by process features
    • B01D15/1835—Flushing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
    • B01D15/1814—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns recycling of the fraction to be distributed
    • B01D15/1821—Simulated moving beds
    • B01D15/1842—Simulated moving beds characterized by apparatus features

Definitions

  • the invention relates to absorption-type separation and/or purification processes.
  • Adsorption from the liquid phase has long been used for removal of contaminants present at low concentrations in process streams.
  • the commercial use of adsorption for the recovery of major components of feed streams as pure products is a comparatively recent development.
  • Examples of bulk separation include the separation of linear paraffins from branched-chain cyclic hydrocarbons, separation of olefins from paraffins, and the separation of C8 aromatic isomers, which include xylenes and ethylbenzene.
  • these processes use zeolitic adsorbents because of the particularly useful selectivities developed, but the technology and theory are equally applicable to suitably selective nonsieve adsorbents such as alumina, charcoal, metal oxides, and so on.
  • SMB have recently also been used for separation on a smaller scale, such as for separating pharmaceuticals, biochemicals, and fragrances.
  • the simulation involves holding the adsorbent in place in one or more cylindrical adsorbent chambers.
  • the positions at which the streams involved in the process enter and leave the chambers are slowly shifted along the length of the beds by means of, for example, a rotary valve, which functions on the same principle as a multi-port stopcock.
  • each line carries one of the four process streams at some point in the cycle.
  • the feedstream is connected to a series of beds in sequence, first to bed no. 1, then to bed no. 2, and so forth for numerous beds, generally being between 12 and 24. These beds may be considered to be portions of a single large bed whose movement is simulated.
  • Each time the feedstream destination is changed it is also necessary to change the destinations (or origins) of at least three other steams, which may be streams entering the beds, such as the feedstream, or leaving the beds, such as the extract and raffinate. Desorbent and various flushes may also enter and leave the beds.
  • 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 steams past the series of fixed beds instead of moving the beds past the introduction and withdrawal points. See U.S. Patent Application 2008036913.
  • the general technique employed in the performance of SMB technology is well described in the literature. For instance a general description directed to the recovery of p- xylene was presented at page 70 of the September 1970 edition of Chemical Engineering Progress (Vol. 66, No 9). A generalized description of the process with an emphasis on mathematical modeling was given at the International Conference on "Fundamentals of Adsorption", Schloss Elmau, Upper Bavaria, Germany on May 6-11, 1983 by D. B. Broughton and S. A. Gembicki.
  • U.S. Patent No. 2,985,589 describes the idea of moving ports on fixed beds and an accompanying rotary valve to distribute stream flows among the fixed beds. See also U.S. Patent Nos. 3,040,777; 3,192,954; 3,422,848. Processes utilizing a rotary valve in an SMB process are described in numerous U.S. Patents such as 3,201,491 and 3,291,726. In U.S. Patent No. 3,706,812, columns are linked together through tees connected to rotary valves, as shown in Figure 1 of the patent. The disclosed system incorporated a check valve between each column and its tee to maintain correct directional flow. The patent also disclosed the use of solenoid valves to move the ports through the columns.
  • a rotary valve as used in SMB may be described as accomplishing the simultaneous interconnection of at two separate groups of conduits.
  • the cyclical advancement of the streams through the solids may also be accomplished by utilizing a manifold arrangement to cause the fluid to flow in a counter current manner with respect to the solids.
  • the valves in the manifold may be operated in a sequential manner to effect the shifting of the steams in the same direction as overall fluid flow throughout the adsorbent solids. See U.S. Patent 3,706,812.
  • UOP SorbexTM Processes which include the ParexTM, MolexTM, and OlexTM processes described above, makes use of a rotary valve that typically distributes net in streams (feed and desorbent), net out streams (extract and raffmate), and assorted flushes (primary flush in, secondary flush in and flush out) to and from the appropriate sieve beds inside the sieve chambers in the SMB unit.
  • the net in, net out and assorted flush streams are sequentially cycled through the various bed lines.
  • the assorted flush streams are necessary to avoid contamination caused by the sharing of the bed lines from the other net in and net out streams.
  • SorbexTM Process units typically process several streams that have significantly different compositions.
  • extract and raffmate are relative terms depending on the nature of the components being separated, the preference of the solids, and the nature of the apparatus or system, as used herein the term “extract” will mean a stream comprising product and desorbent and the term “raffmate” will mean a stream comprising by-products and desorbent.
  • feedstreams having differing compositions for instance feedstreams having higher concentrations of p- xylenes than equilibrium provided by a mixture of xylenes, such as provided by the Mobil Selective Toluene Disproportionation (STDPTM) or Mobil Toluene to P-xylene (MTPXTM) processes, providing feedstreams having >90 wt% p-xylene (see U.S.
  • the present inventors have surprisingly discovered that by providing parallel rotary valves configured or plumbed to operate independently provide, in embodiments, increased capability for additional feed and flush streams, which in embodiments substantially results in either increasing the capacity of a unit or decrease the energy requirement of a unit at constant capacity. This allows the designer and/or operator to optimize multiple feed locations, maintain or increase the number of flushes, such as to flush raff ⁇ nate from the bed lines and flush desorbent into the sieve chambers between the raffinate and desorbent.
  • the invention is directed to parallel distributive valves, preferably rotary valves, configured or plumbed to operate independently in an SMB system.
  • the system comprises at least two rotary valves having crossover piping configured or plumbed differently within each rotary valve so that two separate feeds, one to each rotary valve, may be utilized simultaneously or step-wise within the simulated moving bed absorptive separation system.
  • the invention also concerns a process of using the SMB system according to the invention, comprising the use of two separate feeds in an SMB system having parallel distributive valves.
  • the process comprises the purification of plural feedstreams within an SMB system without the necessity of merging feedstreams.
  • the feedstreams comprises at least two selected from equilibrium xylenes (about 23 wt%), a concentrated p-xylene stream from a selective toluene disproportionation unit (>90 wt%) and filtrate from a crystallizer which is low in p- xylene concentration ( ⁇ 10 wt%).
  • FIG. 1-3 illustrate schematically embodiments of the present invention with respect to a SMB system, such as a SorbexTM Process. More specifically, improvements provided by the present invention include, but are not limited to the following:
  • one rotary valve is configured to flush raffinate out of the bed lines and a second rotary valve is configured to use the raffinate flush out to flush desorbent back into the sieve chambers;
  • an SMB system is provided with at least two distributive valves plumbed independently to allow for simultaneous processing of at least two different feedstreams.
  • the two feeds preferably two different feeds, which in embodiments may be feeds selected from the group consisting of (i) an equilibrium mixture of xylenes; (ii) a mixture of xylenes from a selective toluene disproportion unit having an amount of p-xylene greater than an equilibrium concentration; and (iii) and a mixture of xylenes from a crystallization process having an amount of p- xylene less than an equilibrium concentration, are fed independently to each rotary valve A and B through lines 1 and 2, respectively.
  • the second rotary valve B is configured (plumbed) differently from the first rotary valve A with respect to the bed lines.
  • Parallel rotary valves A and B are configured independently to allow optimization of more than one feed.
  • the three product streams (Raffinate 21, Extract .15 and Extract Flush Out 18) are withdrawn from the same location (sieve chamber 101).
  • the extract is a mixture of desorbent and p-xylene.
  • the raffinate is a mixture of desorbent and p- xylene-depleted xylenes.
  • Extract Flush Out is a mixture of desorbent and p-xylene.
  • Each of these streams may, in more preferred embodiments, be purified downstream (not shown in the schematic) by, for instance, distillation, and the desorbent recycled to the system.
  • the raffinate stream is sent to an isomerization unit (also not shown in the schematic but per se well known in the art) and then may also be recycled as a feedstream in the case where the feedstream to rotary valve A or B is an equilibrium mixture of xylenes.
  • the Desorbent is a component or mixture of components which has an affinity for the sieve which is similar to the component being separated. In the case of p-xylene separations, the desorbent is typically para-diethylbenzene (PDEB).
  • the Feed Flush In is a stream which flushes out the "contaminants" (feed) which lie in the SMB process bed lines.
  • this stream is either PDEB, p-xylene or recycled line Flush Out.
  • the secondary feed flush provides additional bed line flushing closer to the bed line where extract is removed.
  • the secondary feed flush is typically PDEB.
  • the C 8 aromatics feed to a SMB unit typically comes from a number of sources, e.g., reformate, transalkylation, toluene disproportionation, selective toluene disproportionation, xylene isomerization, filtrate from a p-xylene crystallizer, and so on.
  • sources e.g., reformate, transalkylation, toluene disproportionation, selective toluene disproportionation, xylene isomerization, filtrate from a p-xylene crystallizer, and so on.
  • composition of these feeds varies widely in p-xylene purity (e.g., from about 3 wt%, or about 6 wt%, or about 9 wt% to about 80 wt% or about 90 wt%, or about 92 wt%, or about 94 wt%) and also ethylbenzene content (e.g., from about 1 wt% to about 25 wt%), and the feed may be a mixture of xylenes and ethylbenzenes from different sources, so each C 8 isomer may vary from in the feedstream from trace impurity level to 99 wt% or even higher.
  • Ethylbenzene is most notable as it is typically the most difficult isomer to separate from p-xylene.
  • mixing of feedstreams having different concentrations is, generally, thermodynamically inefficient considering that one of the advantages of the present invention is that two disparate feedstreams having in common at least one final product of interest may be processed in an SMB system, without mixing, to derive a common extract comprising said final product of interest.
  • the diverse feedstreams may be selected from refinery and/or chemical plant feedstreams, such as the C 8 aromatics feed discussed above with respect to an SMB process such as the ParexTM Process, include paraffin and/or olefins feedstream.
  • the final product of interest may be p-xylene, o-xylene, m-xylene, ethylene benzene, or mixtures thereof, cumene, one or more paraffins, one or more olefins, fructose and the like.
  • one rotary valve, A is configured or plumbed to flush Raffmate out of the bed lines and the other rotary valve, B, is configured to use the Raffmate Flush Out to flush desorbent back into the sieve chambers.
  • the parallel rotary valve configuration can also be utilized to increase the number of flushes in the SMB Process.
  • the three product streams (Raffmate 21, Extract _15 and Extract Flush Out 18) are withdrawn from the same bed line for each rotary valve A and B.
  • the streams split (e.g., as shown with respect to line 13, into lines 13A and 13B (other notations omitted for convenience of view) to _15 and _18 and flow through each rotary valve before recombining QA, 3B; 5A, 5B; and 8A, 8B; respectively) at the outlet (streams indicated as Raffinate 3, Extract 5 and Flush Out 8).
  • the streams may be sent downstream (plumbing not shown) for further processing, as discussed elsewhere herein, such as distillation followed by recycling.
  • Stream 9 (Raffinate Flush Out) is routed through through bed line IQB to Rotary valve B and this same stream is used as stream IJ) (desorbent flush in), which is routed through rotary valve A into a location between the raffinate withdrawal point _13 and the desorbent feed point 14.
  • Stream 9 which in a preferred embodiment is a mixture of p-xylene depleted xylenes and paradiethylbenzene, will be displacing a bed line full of desorbent (paradiethylbenzene) back into the chamber. By doing so, the desorbent will be fully utilized in the SMB process. In preferred embodiments the rate of this flushing does not exceed the bed line volume/rotary valve stepping rate as this would introduce p-xylene depleted mixed xylenes into a location very close to the desorbent. This could result in contamination of the p-xylene product.
  • FIG. 3 The embodiment of the invention shown in Figure 3 utilizes both feed optimization such as illustrated above in Figure 1 and the optimized flushing as illustrated above in Figure 2.
  • Feeds 1 and 2 are fed by lines IA and 2B, respectively, to rotary valves A and B, respectively, and then to different locations in sieve chamber 102 by streams IJ. and 12.
  • the three product streams (Raffinate 13, Extract _15 and Extract Flush Out 18) are withdrawn from the same location (bed line).
  • Stream 9 (Raff ⁇ nate flush out) is routed through line 9B to Rotary valve B and this same stream is used as stream IQA (desorbent flush in), which is routed through rotary valve A into a location between the raff ⁇ nate withdrawal point and the desorbent feed point.
  • Stream 9 a mixture of p-xylene depleted xylenes and paradiethylbenzene, will be displacing a bed line full of desorbent (paradiethylbenzene) back into the chamber 102. Again, this more fully utilizes the desorbent in the SMB process.
  • the rate of this flushing does not exceed the bed line volume/rotary valve stepping rate as this would introduce p-xylene depleted mixed xylenes into a location very close to the desorbent. This could result in contamination of the p-xylene product.
  • the raff ⁇ nate flush out can be routed through one rotary valve with the disposition of that stream being the raffinate tower feed. Instead of recycling raff ⁇ nate flush out to desorbent flush in (as per Figure 2), the second rotary valve can be plumbed to provide further (secondary) feed flushing capability.
  • an addition preferred embodiments would include increasing the number of raffinate and desorbent streams.
  • Desorbent streams with different composition can be simultaneously fed to different points in the SMB process unit by plumbing the parallel rotary valves differently.
  • the desorbent stream to the rotary valve is a mixture of desorbent which is separated in and recycled from the towers that fractionate the raffinate and extract.
  • the composition of the desorbent from the raffinate tower is slightly different than the composition of the desorbent from the extract tower.
  • the impurities in the desorbent from the raffinate tower are p-xylene-depleted C8 aromatics (predominantly o-xylene since it is the highest boiling C8 aromatic).
  • the impurity in the desorbent from the extract tower is predominantly p-xylene.
  • the process further comprises feeding those streams independently into different points in the sieve beds. In addition, this optimization would allow relaxation of the tower specifications and reduction in energy input.

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé amélioré de séparation et/ou de purification par absorption comportant deux vannes rotatives.
PCT/US2009/060833 2008-11-19 2009-10-15 Procédé de séparation WO2010059317A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
KR1020117014022A KR101362490B1 (ko) 2008-11-19 2009-10-15 분리 방법
CN2009801458103A CN102215930A (zh) 2008-11-19 2009-10-15 分离方法
JP2011536366A JP5662938B2 (ja) 2008-11-19 2009-10-15 分離方法
EP09827944.1A EP2364192A4 (fr) 2008-11-19 2009-10-15 Procédé de séparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11609708P 2008-11-19 2008-11-19
US61/116,097 2008-11-19

Publications (2)

Publication Number Publication Date
WO2010059317A2 true WO2010059317A2 (fr) 2010-05-27
WO2010059317A3 WO2010059317A3 (fr) 2010-07-22

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PCT/US2009/060833 WO2010059317A2 (fr) 2008-11-19 2009-10-15 Procédé de séparation

Country Status (7)

Country Link
US (1) US8168845B2 (fr)
EP (1) EP2364192A4 (fr)
JP (1) JP5662938B2 (fr)
KR (1) KR101362490B1 (fr)
CN (1) CN102215930A (fr)
TW (1) TWI450889B (fr)
WO (1) WO2010059317A2 (fr)

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KR100963746B1 (ko) * 2008-03-13 2010-06-14 삼성토탈 주식회사 유사 이동층 분리법에 의한 방향족 화합물의 분리방법
SG10201402262QA (en) * 2009-05-29 2014-08-28 Exxonmobil Chem Patents Inc Parex Unit Feed
US8569564B2 (en) 2010-03-30 2013-10-29 Exxonmobil Chemical Patents Inc. Separation system
US8329975B2 (en) * 2010-12-20 2012-12-11 Uop Llc Elimination of residual transfer line raffinate from feed to increase normal paraffin separation unit capacity
CN103619432B (zh) 2011-03-23 2015-09-30 埃克森美孚化学专利公司 在吸附分离系统中减少冲洗体积
US8933288B2 (en) * 2013-03-20 2015-01-13 Uop Llc System and process for flushing residual fluid from transfer lines in simulated moving bed adsorption
US9522863B2 (en) 2014-02-28 2016-12-20 Exxonmobil Chemical Patents Inc. Xylene separation process
WO2016003612A1 (fr) 2014-06-30 2016-01-07 Exxonmobil Chemical Patents Inc. Procédés de production de para-xylène
WO2016003613A2 (fr) 2014-06-30 2016-01-07 Exxonmobil Chemical Patents Inc. Procédé de production de xylènes
US10226719B2 (en) 2014-09-30 2019-03-12 Exxonmobil Chemical Patents Inc. Adsorptive separation of multi-component fluid mixtures
US9464012B2 (en) 2014-11-20 2016-10-11 Exxonmobil Chemical Patents Inc. Xylene separation process and apparatus
US20170073285A1 (en) * 2015-09-10 2017-03-16 Uop Llc Processes and apparatuses for toluene methylation in an aromatics complex
US9878968B2 (en) 2016-04-26 2018-01-30 Exxonmobil Chemical Patents Inc. Xylene separation process
CN109153603A (zh) 2016-05-13 2019-01-04 洛科威国际有限公司 用于矿物纤维的包含至少一种水胶体的粘结剂组合物
WO2017201159A1 (fr) 2016-05-20 2017-11-23 Exxonmobil Chemical Patents Inc. Procédé de séparation de xylène
KR101989693B1 (ko) * 2017-11-24 2019-06-14 한화토탈 주식회사 디에틸벤젠 이성질체 혼합물로부터 유사 이동층 공정을 이용한 1,4-디에틸벤젠 분리 방법
CN111448178B (zh) 2017-12-05 2023-01-06 埃克森美孚化学专利公司 二甲苯生产方法和系统
US11027221B2 (en) 2018-10-19 2021-06-08 Uop Llc Process for a dual extract flush

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US8168845B2 (en) 2012-05-01
EP2364192A4 (fr) 2014-03-12
US20100125163A1 (en) 2010-05-20
EP2364192A2 (fr) 2011-09-14
JP2012509162A (ja) 2012-04-19
WO2010059317A3 (fr) 2010-07-22
TW201033174A (en) 2010-09-16
TWI450889B (zh) 2014-09-01
CN102215930A (zh) 2011-10-12
KR20110098744A (ko) 2011-09-01
KR101362490B1 (ko) 2014-02-13

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