CN102076826A - Process and apparatus for separating para-xylene from mixture of c8 and c9 aromatic hydrocarbons - Google Patents
Process and apparatus for separating para-xylene from mixture of c8 and c9 aromatic hydrocarbons Download PDFInfo
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/02—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material
- C10G25/03—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material with crystalline alumino-silicates, e.g. molecular sieves
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/40—Extractive distillation
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
- B01D2253/10—Inorganic adsorbents
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- B01D2256/24—Hydrocarbons
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1096—Aromatics or polyaromatics
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4081—Recycling aspects
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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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/30—Aromatics
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Abstract
The invention includes at least two adsorptive separation zones to separate para-xylene from a feed stream comprising C8 aromatic hydrocarbons and at least one C9 aromatic hydrocarbon component. An adsorbent comprising X or Y zeolite and a heavy desorbent are used in the first adsorptive separation zone to produce an extract stream comprising para-xylene and a raffinate stream comprising para-xylene depleted C8 aromatic hydrocarbons, the C9 aromatic hydrocarbon, and the desorbent. The raffinate stream is separated in a raffinate distillation zone to produce a stream comprising the first desorbent component and the C9 aromatic hydrocarbon which stream is further separated in a second adsorptive distillation zone to produce a stream comprising the desorbent and a C9 aromatic hydrocarbon stream.
Description
Invention field
The present invention relates to be used for from the method and apparatus of the mixture separating paraxylene of the C8 aromatic hydrocarbons that contains at least a C9 aromatic hydrocarbons.Especially, the present invention includes at least two fractionation by adsorption steps.
Background of invention
P-Xylol is important starting material in chemistry and the fiber industry.For example, the terephthalic acid derived from p-Xylol is used to prepare polyester textile.P-Xylol usually from the mixture of p-Xylol and at least a other C8 aromatic hydrocarbons the combination by crystallization, fractionation by adsorption or these two kinds of technology separate.
US 3,392,113 disclose the circulation means of the incoming mixture that is used for the separation of the fluid compound, by make charging and at least a compound to described incoming mixture have optionally solid adsorbent for example molecular sieve contact, and feed the fluid strippant then to contact with sorbent material, replace the compound of the selective adsorption that is obtained thus, described strippant contains the aromatics and/or the oxide impurity of trace usually, it changes the absorption of described method and the kinetics of desorb undesirably in a plurality of absorption-desorption circulations, or speed, stablize dynamics methods and strippant is contacted with independent solid adsorbent beds remove described impurity by in desorption procedure, utilizing.
US 5,012, and 038 approval uses p-diethylbenzene (p-DEB) as being used for from the strippant of C8 aromatic hydrocarbons mixture separating paraxylene usually.Also known use p-DEB has limited in the incoming mixture C9 aromatic hydrocarbons to less than 0.1 weight % as strippant.This requirement is satisfied by at first distillation is next in so-called xylene separator usually.Otherwise C9 aromatic hydrocarbons is built up in the round-robin strippant in the method gradually, because C9 aromatic hydrocarbons is difficult to separate with p-DEB by simple fractionation, and for economic reasons must be with this strippant recirculation.
US 5,012, and 038 and other patent such as US 4,886,930, US 5,057, and 643, US 5,171,922, US 5,177, and 295 and US 5,495,061 disclose the strippant that uses boiling point to be higher than p-DEB with from the C9 aromaticity content greater than separating paraxylene the incoming mixture of 0.1 weight %.Subsequently by fractionation separation of C 9 aromatic hydrocarbons from more high boiling strippant.But although more high boiling strippant provides benefit, p-DEB remains through being usually used in the strippant of p-Xylol fractionation by adsorption.
Summary of the invention
The present invention relates to be used for method and apparatus from the incoming flow separating paraxylene that comprises C8 aromatic hydrocarbons and at least a C9 aromatic component.In one embodiment, this method can comprise makes sorbent material contact in first adsorptive separation zone with first desorbent stream that comprises the first strippant component with incoming flow, makes extract flow that comprises p-Xylol and the raffinate stream that comprises C8 aromatic hydrocarbons, C9 aromatic component and the first strippant component of removing p-Xylol thus; Raffinate stream is separated in the raffinate distillation zone, make second desorbent stream that comprises the first strippant component and C9 aromatic component thus; Second desorbent stream is separated in second adsorptive separation zone, make the 3rd desorbent stream that C9 aromatic hydrocarbons flows and comprise the first strippant component thus.
In another embodiment, the present invention can comprise separating paraxylene from the incoming flow that comprises C8 aromatic hydrocarbons and at least a C9 aromatic component, this method comprises: (a) make first sorbent material that comprises Y zeolite or X zeolite and this incoming flow and comprise first desorbent stream of boiling point at least 150 ℃ the first strippant component contact first raffinate stream that makes first extract flow that comprises the p-Xylol and the first strippant component thus and comprise C8 aromatic hydrocarbons, C9 aromatic component and the first strippant component of removing p-Xylol in first adsorptive separation zone; (b) make first extract flow lead to the extract distillation zone, make second desorbent stream and the p-Xylol product stream that comprise the first strippant component thus; (c) make first raffinate stream lead to the raffinate distillation zone, the raffinate product stream that makes the 3rd desorbent stream that comprises the first strippant component and C9 aromatic component thus and comprise the C8 aromatic hydrocarbons of removing p-Xylol; (d) make at least a portion the 3rd desorbent stream and the desorbent stream that comprises the second strippant component lead to second adsorptive separation zone that comprises second strippant, make second extract flow that comprises the first strippant component and the second strippant component thus and comprise the C9 aromatic component and second raffinate stream of the second strippant component.
In one embodiment, the first strippant component is p-diethylbenzene (p-DEB).In another embodiment, this first adsorptive separation zone is operated with simulation moving-bed pattern.In another embodiment, this first desorbent stream can comprise the nearly C9 aromatic hydrocarbons of 25 weight %.Other embodiment of the present invention comprises disclosed other detailed description in the context, comprises preferred and optional feature.
In another embodiment, the present invention is the device that comprises adsorptive separation zone, extract distillation zone, raffinate distillation zone and second adsorptive separation zone; Wherein the extract conduit provides the fluid from first adsorptive separation zone to the extract distillation zone to be communicated with, the raffinate conduit provides the fluid from first adsorptive separation zone to the raffinate distillation zone to be communicated with, C9 aromatic hydrocarbons conduit provides the fluid from the raffinate distillation zone to second adsorptive separation zone to be communicated with, and circulation duct provides, and at least one fluid to first adsorptive separation zone is communicated with from extract distillation zone and raffinate distillation zone.
In another embodiment, the present invention can comprise the device that is used for from the incoming flow separating paraxylene that comprises C8 aromatic hydrocarbons and at least a C9 aromatic component, this device comprises: (a) first adsorptive separation zone, be used for comprising first adsorbent chamber that contains first sorbent material from this incoming flow separating paraxylene; (b) feed conduit, the fluid that provides charging to flow to first adsorptive separation zone is communicated with; (c) strippant conduit provides the first strippant component to be communicated with to the fluid of first adsorptive separation zone; (d) the first extract distillation zone comprises the extract distillation tower; (e) the first extract conduit provides the fluid from first adsorptive separation zone to the first extract distillation zone to be communicated with; (f) raffinate distillation zone comprises the raffinate distillation tower; (g) the first raffinate conduit provides the fluid from first adsorptive separation zone to the raffinate distillation zone to be communicated with; (h) second adsorptive separation zone is used for the C9 aromatic component is separated with the first strippant component, comprises the second strippant chamber of containing second strippant; (i) C9 aromatic hydrocarbons conduit provides the C9 aromatic component and the first strippant component fluid from the raffinate distillation zone to second adsorptive separation zone to be communicated with; (j) circulation duct provides the first strippant component at least one fluid to first adsorptive separation zone from the first extract distillation zone and raffinate distillation zone to be communicated with.
In another embodiment, circulation duct provides the first strippant component to be communicated with from extract and the two fluid to first adsorptive separation zone of raffinate distillation zone.In another embodiment, the second extract conduit that the fluid that this device further comprises to be provided from second adsorptive separation zone to the second extract distillation zone is communicated with, and second circulation duct that provides fluid to be communicated with from the second extract distillation zone to first adsorptive separation zone.Other embodiment of the present invention comprises disclosed other detailed description in the context, comprises preferred and optional feature.
Thus, on the one hand the present invention by make the C9 aromatic component can with the strippant component fractionation by adsorption of in fractionation by adsorption p-Xylol from the incoming mixture that comprises C8 aromatic hydrocarbons and at least a C9 aromatic hydrocarbons, using, bigger handiness is provided.On the other hand, the present invention by make p-Xylol can be from incoming mixture fractionation by adsorption, bigger handiness is provided, wherein desorbent stream can comprise the nearly C9 aromatic hydrocarbons of 25 weight %.
Description of drawings
Fig. 1 is the simplified flow chart of embodiment of the present invention.
Fig. 2 is the simplified flow chart of having set forth embodiment of the present invention, and wherein the raffinate distillation zone produces three product streams.
Fig. 3 is the simplified flow chart of adsorptive separation zone of the present invention, and it has set forth the fixed bed embodiment.
Fig. 4 is the simplified flow chart of adsorptive separation zone of the present invention, and it has set forth simulation moving-bed embodiment.
Accompanying drawing is intended to illustrate the present invention and is not the scope of the invention that is intended to limit as providing in the claim.Accompanying drawing is the synoptic diagram of simplifying, and the illustrative embodiments that it has shown process flow sheet comprises process island, helps to understand the present invention.The detailed content of process island well known in the art, as pump, control valve, instrument, heat recovery circuit and for understanding the present invention and nonessential similar hardware do not illustrate.
Detailed Description Of The Invention
Adopt two fractionation by adsorption steps or Qu Laicong to comprise separating paraxylene in the incoming flow of C8 aromatic hydrocarbons and at least a C9 aromatic component.One or more equipments unit and/or one or more subarea can be represented in term used herein " district ".The equipment unit can comprise for example one or more containers, well heater, separator, interchanger, conduit, pump, compressor and controller.In addition, the equipment unit may further include one or more districts or subarea.
Incoming flow is at least a mixture that comprises at least two kinds of C8 aromatic hydrocarbons, p-Xylol and m-xylene, o-Xylol and ethylbenzene.This incoming flow also comprises at least a C9 aromatic component, such as any of the isomer of propylbenzene, ethyl methyl benzene and Three methyl Benzene.This incoming flow can comprise several or whole C8 and C9 aromatic hydrocarbons, for example, and in charging during derived from one or more olein sweetening process such as catalytic reforming, steam cracking, crystallizer mother liquor, alkyl exchange and xylene isomerization.
To can contain the nearly C9 aromatic hydrocarbons of 25 weight % by the charging that the present invention handles.Be expected at and use incoming flow in this method with at least 0.1 weight %C9 aromatic hydrocarbons.In one embodiment, this incoming flow can comprise the C9 aromatic hydrocarbons of 0.3 weight %～5 weight %.In another embodiment, this incoming flow can comprise the C9 aromatic hydrocarbons of 6 weight %～15 weight %.In one embodiment, this incoming flow can not contain the C10+ aromatic hydrocarbons that surpasses 10 quality ppm.
Fig. 1 has set forth the schema of embodiment of the present invention.Incoming flow and strippant flow point Tong Guo feed conduit 1 and strippant conduit 3 introducing adsorptive separation zone 100.Adsorptive separation zone 100 comprises adsorbent chamber 110, and it contains in the relative charging other C8 aromatic hydrocarbons for p-Xylol sorbent material selectively.Adsorptive separation zone 100 produces the raffinate stream of being carried by the extract flow of extract conduit 5 conveyings and raffinate conduit 7.As shown in FIG., logistics and they therein the reference numerals of mobile pipeline or conduit be identical.For example, reference numerals 7 can identical accuracy be used as the raffinate stream of raffinate conduit 7, raffinate pipeline 7, raffinate stream 7 and 7 conveyings of raffinate conduit.
Adsorptive separation technology is well known in the art.In brief, incoming flow and desorbent stream are introduced in the adsorbent chamber that can comprise one or more containers that contain sorbent material.During the adsorption step, sorbent material contacts with charging, and optionally keeps a feed component or a class feed component with respect to remaining feed component.By sorbent material is contacted with strippant, the feed component of selective retention is discharged or desorb from sorbent material.Thus, adsorptive separation technology produces the extract flow of the component comprise selective adsorption or a class component and comprises by the raffinate stream of the residue feed component of still less selective adsorption.Desorbent stream can comprise one or more strippant components, and a plurality of desorbent stream of also known use in this area.Extract and the raffinate stream passed through via adsorbent chamber typically also comprise one or more strippant components.
Well-known multiple adsorption separation technology among the present invention comprises as the fixed bed with intermittence or the operation of rocking bed pattern, moving-bed and simulation moving-bed (SMB).The present invention is intended to be limited by specific adsorption separation technology or operator scheme.Out of Memory about fractionation by adsorption principle and detailed content obtains easily, for example Kirk-Othmer Encyclopedia of Chemical Technology the 1st rolls up, the 3rd edition, Adsorptive Separation (Liquids) 563-581 page or leaf, 1978, and Preparative and Production Scale Chromatography, G.Ganetsos and P.E.Barker compile, and 1993.
Because these various adsorptive separation technologies are operated with identical basic chromatogram separation principle, so the following discussion of sorbent material and strippant is applicable to various adsorption separation technologies or pattern.The function of sorbent material and strippant and performance are well-known in the chromatographic separation of liquid ingredient, but as a reference, and with US 4,642,397 are incorporated herein.
With respect to other C8 aromatic hydrocarbons to p-Xylol selectively sorbent material be suitable for adsorptive separation zone 100.It is well known in the art that X is used for p-Xylol is separated with other C8 aromatic hydrocarbons with Y zeolite.Randomly, these zeolites can contain IUPAC the 1st or 2 family's ions on tradable positively charged ion site.In one embodiment, sorbent material comprises X zeolite or Y zeolite.Randomly, sorbent material can comprise barium, potassium or barium and potassium the two.
Also known crystalline aluminosilicate, i.e. zeolite with the form of accumulation body with high physical strength and wear resistance, is used for the fractionation by adsorption of various mixtures.The method that is used for crystal powder is formed this accumulation body comprises inorganic adhesive, be generally the clay that comprises silicon-dioxide and aluminum oxide is added in the high purity zeolite powder of moist mixture.Blended clay zeolite mixture is extruded into cylindrical particle or forms bead, subsequently with its calcining so that clay is converted into the amorphous binder of suitable great machinery intensity.As tackiness agent, use the permeable organic polymer of clay, water or the silica of kaolin form usually.
The pipeline or the desorbent stream in the conduit 3 that adopt in the adsorptive separation zone 100 can comprise one or more strippant components.Suitable strippant component is " weight ", and promptly they have at least 150 ℃ boiling point.In one embodiment, the strippant component has the boiling point more than 160 ℃.In another embodiment, the strippant component has the boiling point more than 170 ℃.The example that is suitable for the strippant component in the logistics 3 of adsorptive separation zone 100 comprises: p-diethylbenzene, diethyl toluene, 1,2,3,4-tetraline, alkyl and dialkyl group-1,2,3,4-tetrahydronaphthalenderivatives derivatives, indane, naphthalene, methylnaphthalene, to dimethylnaphthalene, and composition thereof.In one embodiment, desorbent stream 3 comprises p-diethylbenzene (p-DEB).
In one embodiment, the present invention recognizes that the strippant of introducing adsorptive separation zone 100 can comprise the nearly C9 aromatic hydrocarbons of 25 weight %.In one embodiment, desorbent stream 3 can comprise the C9 aromatic hydrocarbons of at least 0.7 weight %.In another embodiment, the C9 aromaticity content scope of the desorbent stream in the pipeline 3 of introducing adsorptive separation zone 100 is 1～5 weight %; In another embodiment, this scope is the C9 aromatic hydrocarbons of 3～15 weight %.
In the adsorptive separation zone 100, adsorption conditions will comprise 20～300 ℃ temperature range.In one embodiment, the adsorption temp scope is 20～250 ℃, in another embodiment, and 40～200 ℃ of this scopes.Adsorptive pressure is enough to keep liquid phase, and it can be 1～40 crust (gauge pressure).Desorption condition can comprise the temperature and pressure scope identical with being used for adsorption conditions.In the fixed bed embodiment, adsorptive separation zone 100 can adopt the vapor phase adsorption conditions, and the strippant quantity that is retained on the sorbent material is minimized.
The raffinate stream conduit 7 that shifts out from adsorptive separation zone 100 comprises strippant component and more weak adsorbed feed component such as ethylbenzene, o-Xylol, m-xylene and most of C9 aromatic hydrocarbons.Though may there be a spot of p-Xylol, this raffinate stream C8 aromatic hydrocarbons can be called the C8 aromatic hydrocarbons of removing p-Xylol.The extract flow conduit 5 that shifts out from adsorptive separation zone 100 comprise strippant component and the strongest adsorbed feed component (comprise p-Xylol and if present toluene and to ethyl methyl benzene).
As shown in fig. 1, will lead to extract distillation zone 200 from the extract flow 5 that adsorptive separation zone 100 is discharged.Extract distillation zone 200 comprises extract distillation tower 210, and is created in p-Xylol product stream in the pipeline 215 and the desorbent stream that shifts out in conduit 220.Extract product stream 215 can comprise from the whole basically p-Xylol in the extract flow 5 of adsorptive separation zone 100.The compound or a compounds of at least 90%, preferably at least 95% and optimally at least 99% (by weight) in the logistics can be represented to be generally in term used herein " whole basically ".In one embodiment, p-Xylol product stream 215 is from the cat head of extract distillation tower 210 or lightweight stream, and desorbent stream 220 is from the bottom of the tower of extract distillation tower 210 or heavy stream.In one embodiment, can make conduit 250 recirculation of at least a portion desorbent stream 220 by choosing wantonly of shifting out, the desorbent stream 3 that provides at least a portion in adsorptive separation zone 100, to use thus from extract distillation zone 200.Thus, the circulation duct that provides from extract distillation zone 200 to adsorptive separation zone 100 fluid to be communicated with can be the pipeline 220,250 of the fluid flow path these districts of definition and a part of 3.Just, as the other parts of specification sheets, the conduit that provides fluid to be communicated with can comprise a plurality of conduits or its part herein, thus the fluid flow path of definition expectation.
It will be appreciated by the skilled addressee that the technical process in described each district is enough to implement the present invention with being connected herein.Unless point out on the contrary, otherwise accurate tie point is also nonessential for the present invention within these districts.For example, this area is well-known, can directly deliver in the tower to the logistics of distillation zone, perhaps can at first this logistics be delivered in this district other the device as heat exchanger with attemperation, and/or pump with the adjusting pressure.Equally, leave the logistics in district and can directly pass through via distillation tower, perhaps they can pass through via cat head or reboiler section before leaving the distillation zone.
From also can existing ethyl methyl benzene (p-MEB) in the extract flow 5 of adsorptive separation zone 100, and can between the p-Xylol 215 of extract distillation zone 200 and strippant 220 products, distribute with various ratios.Influence factor that p-MEB distributes and comprise parameter between product such as the boiling point of the strippant component of the design of distillation tower and operation and employing.As being familiar with herein, the desorbent stream 3 of introducing adsorptive separation zone 100 can contain the nearly C9 aromatic hydrocarbons of 25 weight %, and it can comprise p-MEB.Owing to be desirably in circulant solution vapor in this technology for economic reasons, therefore can control p-MEB unacceptable accumulation in extract distillation zone desorbent stream 220 in many ways.
In one embodiment, can limit the p-MEB content in the incoming flow 1 of adsorptive separation zone 100, make the p-MEB quantity in the incoming flow 1 be no more than 0.05 weight % of p-Xylol in the incoming flow 1.In the selection of Xian Shiing, do not purify stream and can remove the strippant that contain p-MEB of a part, and more highly purified strippant can be introduced in the schema as a supplement from pipeline 220.In another embodiment, the design of extract distillation zone 210 and operation have improved the p-MEB quantity in the p-Xylol product 215.Contain the p-Xylol of at least 99.7 weight % though often expect p-Xylol product 215, always do not need from p-Xylol product 215, to remove p-MEB.For example, with preparation during terephthalic acid, the oxidation of p-MEB obtains same products with the oxidation of p-Xylol product.Thus, not removing p-MEB from p-Xylol product 215 may be favourable actually.
As shown in fig. 1, the raffinate stream 7 in self-priming Fufen abscission zone 100 is led to raffinate distillation zone 300 in the future.Raffinate distillation zone 300 comprises raffinate distillation tower 310 and produces raffinate product stream 315 and desorbent stream 320.In one embodiment, be raffinate product stream 315 from the cat head of raffinate distillation tower 310 or lightweight stream, and be desorbent stream 320 from the cat head or the heavy stream of distillation tower 310.Basically whole C8 aromatic hydrocarbons (removing the C8 aromatic hydrocarbons of p-Xylol) in raffinate product stream 315 raffinate stream 7 that can comprise from adsorptive separation zone 100.The desorbent stream 320 that shifts out from raffinate distillation zone 300 can comprise whole basically strippant in the raffinate stream 7 that shifts out from adsorptive separation zone 100.In one embodiment, can be by optional conduit 350 with at least a portion desorbent stream 320 circulations that raffinate distillation zone 300 produces, the desorbent stream 3 of the introducing that at least a portion uses in adsorptive separation zone 100 is provided thus.
It is 152～176 ℃ boiling point that C9 aromatic hydrocarbons has scope.Thus, if the boiling point of strippant component is not enough high as when p-DEB is the strippant component, will lead to raffinate distillation zone strippant 320 streams from number of C 9 aromatic hydrocarbons in the raffinate stream 7 of adsorptive separation zone 100.Adsorptive separation zone 400 prevents that unacceptable C9 aromatic hydrocarbons is built up in the desorbent stream 3 (can be recycled to adsorptive separation zone 100).In the embodiment when the strippant component has the boiling point higher than p-DEB, also can adopt adsorptive separation zone 400.Though can more high boiling strippant be separated with C9 aromatic hydrocarbons by distillation, the invention provides the alternative route of the C9 aromaticity content of these strippants of control, it need not the strippant that the raffinate distillation tower provides no C9 aromatic hydrocarbons.
Incoming flow 380 to adsorptive separation zone 400 comprises the desorbent stream 320 of at least a portion from raffinate distillation zone 300, and it comprises from the strippant component of first adsorptive separation zone 100 and C9 aromatic hydrocarbons.Thus, provide conduit 320 that the fluid of 300 to second adsorptive separation zone 400 from the raffinate distillation zone is communicated with and 380 or its part also can be described as C9 aromatic hydrocarbons conduit.As described in about adsorptive separation zone 100, the present invention is intended to be limited by specific adsorption separation technology or operator scheme, and previously mentioned any technology or pattern can adopt in adsorptive separation zone 400.The desorbent stream that adsorptive separation zone 400 also need be provided by conduit 20.For fear of obscuring, term " the first strippant component " will be illustrated in the strippant of use in first adsorptive separation zone 100, and the strippant of the strippant in second adsorptive separation zone 400 is introduced and is used as in term " the second strippant component " expression simultaneously by conduit 20.
In one embodiment, adsorptive separation zone 400 adsorption conditionses can comprise 20～300 ℃ temperature range, and in another embodiment, this temperature range is 20～250 ℃, randomly 40～200 ℃.Adsorptive pressure is enough to keep liquid phase, and it can be 1～40 crust (gauge pressure).Desorption condition can comprise the temperature and pressure scope identical with being used for adsorption conditions.In the fixed bed embodiment, second adsorptive separation zone 400 can adopt the vapor phase desorption condition, makes thus introducing logistics 380 to minimize with the quantity that begins adsorption/desorption circulation time next time and be retained in second absorbent component on the sorbent material.
In another embodiment, second sorbent material with respect to the C9 aromatic component for molecular diameter and p-diethylbenzene (p-DEB) quite or the first littler strippant component selective.For example, second sorbent material can comprise the MFI type zeolite (can obtain) of Structure Commission of the International Zeolite Association regulation on network address www.iza-structure.org/databases.Thus, be applicable to the first strippant component in this embodiment comprise p-DEB, 1,2,3,4-tetralin, indane, naphthalene, methylnaphthalene, to dimethylnaphthalene.As before, the second strippant component can be selected from this identical classification, except the first strippant component itself.Second sorbent material can be identical with first sorbent material, and perhaps second sorbent material can be different from first sorbent material.For para-selectivity or molecular diameter selective adsorbent, the first strippant component will be discharged from second adsorptive separation zone 400 in extract flow 420, and C9 aromatic hydrocarbons will be discharged in raffinate stream 430 simultaneously.
Second strippant that uses in the adsorptive separation zone 400 can comprise one or more components.For example, lightweight strippant component such as benzene and toluene are second strippants that suits, and can contain a spot of non-aromatics, for example less than 10 weight %.In one embodiment, the boiling point of the boiling point of the second strippant component and the first strippant component and C9 aromatic hydrocarbons differs at least 5 ℃.Use second strippant heavier,, can provide the energy saving if in optional step with in distinguishing they are being separated like that as discussed below than first strippant.In one embodiment, the first strippant component is p-DEB, and the second strippant component is benzene, toluene, indane, naphthalene, methylnaphthalene or to dimethylnaphthalene.
The raffinate stream that shifts out from adsorptive separation zone 400 in conduit 430 comprises the second strippant component and C9 aromatic component.In an embodiment that does not show,, make C9 aromatic product stream thus and can be recycled to logistics second adsorptive separation zone 400, that comprise the second strippant component raffinate stream 430 fractionation in the distillation zone.
The extract flow that shifts out from adsorptive separation zone 400 in conduit 420 comprises the first strippant component and the second strippant component.As shown in fig. 1, part or all extract flow 420 can be led to the optional distillation zone 500 that comprises distillation tower 510, be created in the desorbent stream that comprises the first strippant component in the conduit 550 thus, it is recycled to first adsorptive separation zone 100.Also as shown in the figure, can randomly in conduit 460, part or all extract flow 420 be led to extract distillation zone 200, wherein can be as described above separate with the first strippant component (for example being respectively toluene and p-DEB) and reclaim second.Randomly, can part or all lightweight be flowed 230 recirculation, provide at least a portion to introduce the second strippant component stream 20 of second adsorptive separation zone 400 thus by conduit 270.In one embodiment, can be with from first at least a in extract desorbent stream 220, raffinate desorbent stream 320 and the second adsorptive separation zone extract flow 420 strippant component recirculation, the desorbent stream 3 that provides at least a portion to be used for first adsorptive separation zone 100 thus.The flow velocity of each logistics among each schema options that can comprise the first strippant component by adjusting, control feed C9 aromaticity content and other specification of the desorbent stream 3 of adsorptive separation zone 100.In one embodiment, can operate second adsorptive separation zone 400 off and on.
In the embodiment as shown in Figure 2, raffinate distillation zone 300 produces the 3rd and flows out logistics 318.Such as previously discussed, the those of ordinary skill in distillation field is realized three product streams easily.Set forth the second optional raffinate distillation tower 311 among Fig. 2.Raffinate product stream 315 comprises the C8 aromatic hydrocarbons of removing p-Xylol, and desorbent stream 320 comprises the first strippant component and C9 aromatic hydrocarbons.The 3rd flows out logistics 318 has the boiling point higher than desorbent stream 320.Thus, in this embodiment, desorbent stream 320 is an intermediary raffinate product stream, and logistics 318 is from the bottom product of raffinate distillation zone 310 and can be referred to as another desorbent stream, because it comprises the first strippant component.Though can be in each of logistics 315,318 and 320 from a part of C9 aromatic hydrocarbons in the raffinate stream 7 of first adsorptive separation zone 100, the C9 density of aromatic hydrocarbon (weight %) in the desorbent stream 318 is less than the C9 density of aromatic hydrocarbon (weight %) in the desorbent stream 320.In embodiment shown in Figure 2, the more highly enriched C9 aromatic hydrocarbons of at least a portion is passed through via conduit 320 and 380, it is separated with the first strippant component in second adsorptive separation zone 400.Desorbent stream 318 recirculation of C9 aromatic hydrocarbons that at least a portion had lower concentration are to form a part of desorbent stream 3.
Because the present invention is not limited to the type or the pattern of fractionation by adsorption, so those of ordinary skills can be applied to each adsorptive separation zone with following description easily, although they are only described once.In the intermittent mode embodiment, adsorptive separation zone comprises adsorbent chamber, and it has one or more containers that are included in the sorbent material in one or more beds.Intermittent mode operation is by in turn introducing charging in adsorbent chamber and strippant is subsequently formed.Make alternative absorption of sorbent material experience and desorption procedure thus, produce the raffinate stream and the extract flow that alternately flow out adsorbent chamber.In one embodiment, second adsorptive separation zone 400 can be operated with intermittent mode, as shown in Figure 3.The raffinate distillation zone strippant of introducing by conduit 380 is the second adsorption zone charging, and introduces the second adsorption zone strippant that comprises the second strippant component in conduit 20.Thus, conduit 380 and 20 is alternately working aspect the fluid connection that is provided to adsorptive separation zone 400.Equally, raffinate 430 and extract 420 conduits alternately work providing respectively aspect the fluid connection of the raffinate of adsorptive separation zone 400 and extract flow.As shown, logistics can be via each inlet or common inlet, and it has control mobile valve (not shown), enters or leave adsorbent chamber.
In the rocking bed pattern, the strippant chamber comprises at least two adsorbent beds or container, its each operate with intermittent mode, wherein adsorbent bed can be operated under adsorption/desorption round-robin different step.The rocking bed pattern can realize continuous production when adsorbent chamber is included in enough containers of adsorption/desorption round-robin different time point operation, the more uniform product quality from whole adsorptive separation zone is provided thus.The two is the type of ADSORPTION IN A FIXED BED separating technology for intermittent mode and rocking bed pattern.In ADSORPTION IN A FIXED BED was separated, desorption condition can be similar to adsorption conditions.In another embodiment, can adopt the vapor phase desorption condition, make thus to minimize with the strippant quantity that begins next adsorption/desorption circulation time and be retained on the sorbent material introducing charging.For example, can reduce desorption pressures and/or can improve temperature with respect to adsorption conditions.In one embodiment, at least one in first adsorptive separation zone 100 and second adsorptive separation zone 400 is the ADSORPTION IN A FIXED BED disengaging zone, and distinguish in 100 and 400 one or both of can be with intermittently or the operation of rocking bed pattern.
Arbitrary adsorptive separation zone or the two also can be operated with moving-bed fractionation by adsorption system, and wherein sorbent material moves via adsorbent chamber, introduce charging and desorbent stream simultaneously and discharge extract and raffinate stream at independent place, fixed position from adsorbent chamber.
In one embodiment, at least one in first adsorptive separation zone 100 and second adsorptive separation zone 400 is simulation moving-bed (SMB) adsorptive separation zone.In another embodiment, first adsorptive separation zone 100 is simulated moving bed adsorption disengaging zone, and second adsorptive separation zone 400 is ADSORPTION IN A FIXED BED disengaging zone.
[0050] Fig. 4 has described wherein adsorptive separation zone 100 with the embodiment of simulation bed (SMB) operation, comprises that having at least eight transmits the adsorbent chamber 110 that point 115, fluid distributor 120 and at least one are transmitted pipeline 125 (be provided at each transmit point be communicated with fluid between the fluid distributor).Adsorbent chamber 110 contains many to the p-Xylol independent bed 112 of sorbent material selectively.Each bed transmit to be put and to be in during fluid is communicated with one.In one embodiment, adsorbent chamber has 16 transmission points.In another embodiment, adsorbent chamber comprises two placed in-line containers, and each container has 12 and transmits point.
In the SMB embodiment, four main technique are flowed: charging, strippant, extract and raffinate stream feed adsorptive separation zone simultaneously and therefrom discharge, and adsorb simultaneously and desorption procedure.The fluid that feed conduit 1 and strippant conduit 3 are provided to fluid distributor 120 is communicated with.Raffinate conduit 7 and extract conduit 5 provide the fluid from fluid distributor 120 to be communicated with.Fluid distributor passes through to transmit pipeline 125 and transmits and select 115 with process flow importing and derivation strippant chamber 110.At least four are transmitted pipeline/transmission point to working in the given time.Just, each of four main technique stream is flowed through one and is transmitted pipeline/right.When optional logistics flows into or flow out adsorbent chamber, transmission pipeline in addition/to also working.US 3,201,491 and US 4,319,929 in provided the example of optional logistics.
In the SMB adsorptive separation technology, step in the adsorbent chamber or operational zone are defined as follows by the position of input and input logistics.District 1, adsorption zone are included in the sorbent material between the outlet of feed entrance and raffinate.District 2, zone purification are included in the sorbent material between the outlet of feed entrance and extract, and are positioned at the upstream in district 1.District 3, desorption zone are included in the strippant between extract outlet and the strippant inlet, and are positioned at the upstream in district 2.Optional district 4, buffer zone when using this district, are included in the sorbent material between strippant inlet and the raffinate outlet.Can be about device and other detailed content of technology in the SMB technology for example at US 3,208,833, US 3,214,247, US3,392,113, US 3,455, and 815, US 3,523,762, US 3,617,504, US 4,133,842 and US 4,434,051 in find.
In another wide in range embodiment, the present invention is the device that is used for from the incoming flow separating paraxylene that comprises C8 aromatic hydrocarbons and C9 aromatic hydrocarbons, this device comprises: (a) be used for the simulated moving bed adsorption disengaging zone from this incoming flow separating paraxylene, it comprises: (i) have at least eight adsorbent chamber of transmitting point, this transmission point provides with the fluid of contained first sorbent material in this adsorbent chamber and is communicated with; The fluid distributor that (ii) comprises feed entrance, strippant inlet, raffinate outlet, extract outlet; (iii) at least one is used for the transmission pipeline that each transmits point, and it provides from fluid distributor and is communicated with to the fluid that transmits point; (b) feed conduit, its fluid that provides charging to flow to simulated moving bed adsorption disengaging zone feed entrance is communicated with; (c) the first strippant conduit, it provides the first strippant component to be communicated with to the fluid of simulated moving bed adsorption disengaging zone strippant inlet; (d) the first extract distillation zone, it comprises the extract distillation tower; (e) the first extract conduit, it provides the fluid connection that exports to the first extract distillation zone from simulated moving bed adsorption disengaging zone extract; (f) raffinate distillation zone, it comprises the raffinate distillation tower; (g) the first raffinate conduit, it provides the fluid from the simulated moving bed adsorption disengaging zone to the raffinate distillation zone to be communicated with; (h) be used for C9 aromatic component and the isolating ADSORPTION IN A FIXED BED of first strippant component disengaging zone, it comprises second adsorbent chamber that contains second sorbent material; (i) C9 aromatic hydrocarbons conduit, it provides the C9 aromatic component and the first strippant component fluid from the raffinate distillation zone to the ADSORPTION IN A FIXED BED disengaging zone to be communicated with; (j) circulation duct, it provides the first strippant component at least one fluid to simulated moving bed adsorption disengaging zone strippant inlet from the first extract distillation zone and raffinate distillation zone to be communicated with.
This device may further include the second strippant conduit, it provides the fluid from the first strippant component of raffinate distillation zone to be communicated with, and wherein circulation duct provides the fluid of the inlet from the second strippant conduit to simulated moving bed adsorption disengaging zone strippant to be communicated with.
In another embodiment, circulation duct provides the first strippant component to be communicated with from the first extract distillation zone to the fluid of simulated moving bed adsorption disengaging zone strippant inlet.Randomly, second circulation duct provides the first strippant component to be communicated with from the raffinate distillation zone to the fluid of simulated moving bed adsorption disengaging zone strippant inlet.
In another embodiment, this device further comprises the second extract distillation zone, the second extract conduit and the 3rd circulation duct, wherein the second extract conduit provides the fluid of the first strippant component from the ADSORPTION IN A FIXED BED disengaging zone to the second extract distillation zone to be communicated with, and the 3rd cycling stream provides the first strippant component to be communicated with from the second extract distillation zone to the fluid of simulated moving bed adsorption disengaging zone strippant inlet.
Claims (10)
1. be used for from the method for the incoming flow separating paraxylene that comprises C8 aromatic hydrocarbons and at least a C9 aromatic component, this method comprises:
(a) making first sorbent material that comprises Y zeolite or X zeolite is that first desorbent stream of the first strippant component of 150C contacts first raffinate stream that makes first extract flow that comprises the p-Xylol and the first strippant component thus and comprise C8 aromatic hydrocarbons, C9 aromatic component and the first strippant component of removing p-Xylol in first adsorptive separation zone at least with this incoming flow with comprising boiling point;
(b) make first extract flow lead to the first extract distillation zone, make second desorbent stream and the p-Xylol product stream that comprise the first strippant component thus;
(c) make first raffinate stream lead to the raffinate distillation zone, the raffinate product stream that makes the 3rd desorbent stream that comprises the first strippant component and C9 aromatic component thus and comprise the C8 aromatic hydrocarbons of removing p-Xylol;
(d) make at least a portion the 3rd desorbent stream and the logistics that comprises the second strippant component lead to second adsorptive separation zone that comprises second sorbent material, make second extract flow that comprises the first strippant component and the second strippant component thus and comprise the C9 aromatic component and second raffinate stream of the second strippant component.
2. the process of claim 1 wherein that this first strippant component is selected from p-diethylbenzene, diethyl toluene, 1,2,3,4-tetralin, 1,2,3,4-tetralin derivative, indane, naphthalene, methylnaphthalene and to dimethylnaphthalene.
3. the method for claim 1, wherein this raffinate distillation zone further produces the 4th desorbent stream, the 4th desorbent stream has the C9 aromatic hydrocarbons weight % concentration lower than the C9 aromatic hydrocarbons weight % concentration of the 3rd desorbent stream, and at least a portion the 4th desorbent stream is recycled to step (a) at least a portion as first desorbent stream.
4. the method for claim 1, it further comprises: make second extract flow lead to the second extract distillation zone, make the 5th desorbent stream that comprises the first strippant component thus, and make at least a portion the 5th desorbent stream be recycled to step (a) at least a portion as first desorbent stream.
5. the method for claim 1, it further comprises: make at least a at least a portion of second desorbent stream and the 3rd desorbent stream be recycled to step (a) at least a portion as first desorbent stream.
6. the method for claim 1, it further comprises: make at least a portion second extract flow be recycled to the first extract distillation zone.
7. the process of claim 1 wherein that this first desorbent stream comprises the C9 aromatic hydrocarbons that is no more than 25 weight %.
8. the process of claim 1 wherein that this first adsorptive separation zone is the simulated moving bed adsorption disengaging zone, it is operated under the pressure range of 20～30 ℃ temperature range and 1～40 crust (gauge pressure) with convection model, and this first strippant zeolite further comprises barium.
9. be used for from the device of the incoming flow separating paraxylene that comprises C8 aromatic hydrocarbons and at least a C9 aromatic component, this device comprises:
(a) first adsorptive separation zone is used for comprising first adsorbent chamber that contains first sorbent material from this incoming flow separating paraxylene;
(b) feed conduit, the fluid that provides charging to flow to first adsorptive separation zone is communicated with;
(c) strippant conduit provides the first strippant component to be communicated with to the fluid of first adsorptive separation zone;
(d) the first extract distillation zone comprises the extract distillation tower;
(e) the first extract conduit provides the fluid from first adsorptive separation zone to the first extract distillation zone to be communicated with;
(f) raffinate distillation zone comprises the raffinate distillation tower;
(g) the first raffinate conduit provides the fluid from first adsorptive separation zone to the raffinate distillation zone to be communicated with;
(h) second adsorptive separation zone is used for the C9 aromatic component is separated with the first strippant component, comprises second adsorbent chamber that contains second sorbent material;
(i) C9 aromatic hydrocarbons conduit provides the C9 aromatic component and the first strippant component fluid from the raffinate distillation zone to second adsorptive separation zone to be communicated with; With
(j) circulation duct provides the first strippant component at least one fluid to first adsorptive separation zone from the first extract distillation zone and raffinate distillation zone to be communicated with.
10. the device of claim 1, the raffinate product conduit that it the p-Xylol product conduit that provides the fluid from the first extract distillation zone to be communicated with further is provided, provide the second strippant conduit that the fluid from the first extract distillation zone is communicated with and provide the fluid from the raffinate distillation zone to be communicated with.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/146,975 US7972568B2 (en) | 2008-06-26 | 2008-06-26 | Apparatus for separating para-xylene from a mixture of C8 and C9 aromatic hydrocarbons |
| US12/146,901 US7838713B2 (en) | 2008-06-26 | 2008-06-26 | Process for separating para-xylene from a mixture of C8 and C9 aromatic hydrocarbons |
| US12/146,975 | 2008-06-26 | ||
| US12/146,901 | 2008-06-26 | ||
| PCT/US2009/047580 WO2009158242A2 (en) | 2008-06-26 | 2009-06-17 | Process and apparatus for separating para-xylene from a mixture of c8 and c9 aromatic hydrocarbons |
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| CN102076826A true CN102076826A (en) | 2011-05-25 |
| CN102076826B CN102076826B (en) | 2013-10-09 |
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| CN200980124301.2A Active CN102076826B (en) | 2008-06-26 | 2009-06-17 | Process and apparatus for separating para-xylene from mixture of c8 and c9 aromatic hydrocarbons |
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| JP (1) | JP5559782B2 (en) |
| KR (1) | KR101591544B1 (en) |
| CN (1) | CN102076826B (en) |
| PL (1) | PL215253B1 (en) |
| RU (1) | RU2491322C2 (en) |
| SG (1) | SG175654A1 (en) |
| WO (1) | WO2009158242A2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103012045A (en) * | 2011-09-28 | 2013-04-03 | 中国石油化工股份有限公司 | Method for adsorbing and separating m-xylene from C8 aromatics |
| CN105531250A (en) * | 2013-09-27 | 2016-04-27 | 环球油品公司 | Systems and methods for producing desired xylene isomers |
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| US8704031B2 (en) * | 2010-06-30 | 2014-04-22 | Uop Llc | Adsorptive process for separation of C8 aromatic hydrocarbons |
| US8697928B2 (en) * | 2011-12-15 | 2014-04-15 | Uop Llc | Process and apparatus for para-xylene production using multiple adsorptive separation units |
| BR112015008035A2 (en) * | 2012-10-10 | 2017-07-04 | Gtc Technology Us Llc | processes and systems for obtaining aromatics from hydrocarbon catalytic cracking |
| US9522862B2 (en) * | 2014-06-30 | 2016-12-20 | Uop Llc | Simulated moving bed separators and methods for isolating a desired component |
| FR3023841B1 (en) * | 2014-07-18 | 2016-07-15 | Ifp Energies Now | PROCESS FOR PRODUCING PARAXYLENE COMPRISING TWO SIMUL MOBILE BED SEPARATION UNITS AND TWO ISOMERIZING UNITS, ONE OF WHICH IS GAS PHASE |
| 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. |
| FR3023840B1 (en) * | 2014-07-18 | 2016-07-15 | Ifp Energies Now | PROCESS FOR THE PRODUCTION OF HIGH PURITY PARAXYLENE FROM XYLENE CUTTING USING TWO SERIES MOBILE BED SEPARATION UNITS OPERATING IN SERIES AND TWO ISOMERIZING UNITS |
| US10287222B1 (en) * | 2017-10-20 | 2019-05-14 | Uop Llc | Process and apparatus for desorbent recovery |
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- 2009-06-17 KR KR1020107027743A patent/KR101591544B1/en active IP Right Grant
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- 2009-06-17 JP JP2011516446A patent/JP5559782B2/en not_active Expired - Fee Related
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| CN103012045A (en) * | 2011-09-28 | 2013-04-03 | 中国石油化工股份有限公司 | Method for adsorbing and separating m-xylene from C8 aromatics |
| CN103012045B (en) * | 2011-09-28 | 2015-09-23 | 中国石油化工股份有限公司 | The method of adsorption separation of m-Xylene from C8 aronmatic |
| CN105531250A (en) * | 2013-09-27 | 2016-04-27 | 环球油品公司 | Systems and methods for producing desired xylene isomers |
| CN105531250B (en) * | 2013-09-27 | 2019-04-09 | 环球油品公司 | The system and method for being used to prepare required xylene isomer |
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| Publication number | Publication date |
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| JP5559782B2 (en) | 2014-07-23 |
| CN102076826B (en) | 2013-10-09 |
| WO2009158242A2 (en) | 2009-12-30 |
| PL393468A1 (en) | 2011-07-18 |
| WO2009158242A3 (en) | 2010-03-25 |
| SG175654A1 (en) | 2011-11-28 |
| JP2011525919A (en) | 2011-09-29 |
| KR20110021872A (en) | 2011-03-04 |
| PL215253B1 (en) | 2013-11-29 |
| KR101591544B1 (en) | 2016-02-03 |
| RU2491322C2 (en) | 2013-08-27 |
| RU2011102767A (en) | 2012-08-10 |
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