EP1458662A1 - Recuperation de produit de separation par adsorption au moyen de la distillation fractionnee - Google Patents

Recuperation de produit de separation par adsorption au moyen de la distillation fractionnee

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Publication number
EP1458662A1
EP1458662A1 EP01992181A EP01992181A EP1458662A1 EP 1458662 A1 EP1458662 A1 EP 1458662A1 EP 01992181 A EP01992181 A EP 01992181A EP 01992181 A EP01992181 A EP 01992181A EP 1458662 A1 EP1458662 A1 EP 1458662A1
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EP
European Patent Office
Prior art keywords
stream
compound
fractionation
desorbent
adsorbent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01992181A
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German (de)
English (en)
Inventor
David A. Uop Llc HAMM
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell UOP LLC
Original Assignee
UOP LLC
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Filing date
Publication date
Application filed by UOP LLC filed Critical UOP LLC
Publication of EP1458662A1 publication Critical patent/EP1458662A1/fr
Withdrawn legal-status Critical Current

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • 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
    • B01D3/14—Fractional distillation or use of a fractionation or rectification column
    • B01D3/141—Fractional distillation or use of a fractionation or rectification column where at least one distillation column contains at least one dividing wall
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C07B63/04—Use of additives
    • 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

Definitions

  • the invention relates to a continuous adsorptive separation process used to separate chemical compounds such as C 8 aromatic hydrocarbons.
  • Adsorptive separation is one such method.
  • a feed mixture comprising two or more compounds of different skeletal structure is passed through one or more beds of an adsorbent which selectively adsorbs a compound of one skeletal structure while permitting other components of the feed stream to pass through the adsorption zone in an unchanged condition.
  • the flow of the feed through the adsorbent bed is stopped and the adsorption zone is then flushed to remove nonadsorbed materials surrounding the adsorbent.
  • the desired compound is desorbed from the adsorbent by passing a desorbent stream through the adsorbent bed.
  • the desorbent material is commonly also used to flush nonadsorbed materials from the void spaces around and within the adsorbent. This could be performed in a single large bed of adsorbent or in several parallel beds on a swing bed basis.
  • SMB simulated moving bed
  • the passage of the desorbent through the adsorbent dislodges the selectively retained compounds to produce an extract stream.
  • the extract stream contains a mixture of desorbent and the desired compounds, with these materials being then separated by distillation in a column referred to as the extract column. If more than one compound is retained on the adsorbent and removed as part of the extract, then it is necessary to perform yet another fractionation in a finishing column.
  • the subject invention is aimed at improving the economics of the fractionation employed in recovering the final desired compound from the extract stream.
  • S B processes typically employ a rotary valve and a plurality of lines to simulate the countercurrent movement of an adsorbent bed through adsorption and desorption zones. This is depicted, for instance, in US-A-3,205,166 and US-A- 3,201 ,491.
  • US-A-3, 510,423 provides a depiction of the customary manner of handling the raffinate and extract streams removed from an SMB process, with the desorbent being recovered, combined and recycled to the adsorption zone.
  • US-A-4, 036,745 describes the use of dual desorbents with a single adsorption zone to provide a higher purity paraffin extract.
  • US-A-4,006,197 extends this teaching on desorbent recycling to three component desorbent mixtures.
  • US-A- 5,177,295 describes the fractionation of a "heavy" desorbent used in the recovery of paraxylene from a mixture of aromatic hydrocarbons.
  • the invention is an improved simulated moving bed adsorptive separation process characterized by the use of an integrated fractional distillation column to separate a stream comprising two extract components plus the desorbent into three product streams in only a single fractionation column. That is, the three-component extract stream of the adsorptive separation zone is separated into three high purity process streams in a single dividing wall column. A portion of the column is divided by a vertical wall into parallel fractionation zones with one receiving the extract stream and the other delivering a product stream of the adsorptive separation zone. The desorbent is preferably rejected from the bottom portion of the column. A light product may be recovered overhead. This reduces the capital and operating costs of the required separation and thus of the adsorption process.
  • One broad embodiment of the invention may be characterized as a simulated moving bed adsorptive separation process which comprises passing a feed stream comprising a first, second and third chemical compounds into an adsorption zone comprising a bed of a selective adsorbent maintained at adsorption promoting conditions under which the first compound is selectively retained on a quantity of the selective adsorbent compared to the second compound, with the third compound having a boiling point sufficiently different from the first and second compounds to allow its facile separation by fractional distillation and with the third compound being adsorbed onto the adsorbent to a lesser extent than said first chemical compound, and thus forming a raffinate stream comprising the second compound and a desorbent formerly present in the quantity of the selective adsorbent; passing a desorbent stream comprising a desorbent compound into contact with said quantity of the selective adsorbent, which has retained the first chemical compound, under desorption promoting conditions to yield an extract stream comprising the desorbent compound, the first compound and the third compound;
  • the Drawing is a highly simplified process flow diagram showing the extract stream recovered from the adsorbent chamber 14 being passed into the left hand fractionation zone of a single dividing wall product recovery column 6.
  • Adsorptive separation is widely used to perform the separations mentioned above.
  • a desorbent provides the driving force to release the compounds selectively retained upon an adsorbent. Therefore the adsorbent must be continuously cycled between exposure to the feed stream and to a desorbent stream. As described below, this forms at least two effluent streams, the raffinate stream containing unadsorbed compounds and the extract stream containing the desired desorbent compound, which may comprise an admixture of several compounds, and the desorbent. It is an objective of the subject invention to provide a more economical process for recovering the desorbent compound from these two streams produced during adsorptive separation.
  • a single integrated column containing parallel fractionation zones in a single column is employed instead of individual columns.
  • Each fractionation zone occupies only a portion of the cross-section of the column, and both zones are in open communication at both ends with a larger area undivided section of the column. This open communication at both the top or bottom end of the fractionation zones allows adaptation of the process to a desorbent having a lower or a higher boiling point than the raffinate and extract components of the feed.
  • the Drawing illustrates a portion of a simulated moving bed adsorptive separation process having a single adsorbent chamber 14. Only one of the two columns employed in the process is shown. The other column may be of conventional design similar to the depicted column.
  • the process is being employed to separate a feed stream of line 1 comprising a minor amount of toluene and a mixture of several C 8 aromatic hydrocarbons including paraxylene.
  • the feed will normally also comprise metaxylene, orthoxylene and ethylbenzene.
  • the toluene is a remnant of imprecise upstream fractionation. The very close volatilities of these Cs aromatic compounds makes it impractical to separate them on a commercial scale by fractional distillation.
  • the feed stream of line 1 is passed into a rotary valve 2.
  • This rotary valve has a number of ports corresponding to the number of adsorption chamber process streams plus the number of sub beds of adsorbent located in the one or more adsorbent chambers used in the process.
  • the adsorbent chamber(s) may contain from 8 to 24 adsorbent sub beds, there are a large number of bed lines involved in the process and 12 to 30 separate lines normally connect to the rotary valve 2. For simplicity only those bed lines in use at the moment in time being depicted are shown on the drawing. The flows at other times are similar but occur via different bed lines not shown.
  • the rotary valve 2 directs the feed stream into bed line 3 which carries it to the adsorbent chamber 14.
  • the feed stream enters into the adsorbent chamber at a boundary between two of the sub beds and is distributed across the cross-section of the chamber. It then flows downward through several sub- beds of adsorbent containing particles.
  • the adsorbent selectively retains one compound or structural class of compound, which in this instance is paraxylene.
  • the adsorbent also retains some toluene.
  • the other C 8 components of the feed stream continue to flow downward and are removed from the adsorbent chamber in the raffinate stream carried by line 4.
  • the raffinate stream will also comprise a varying amount of desorbent compound(s) flushed from the inter-particle void volume of the adsorbent by the flowing feed stream and also removed from the surface of the adsorbent.
  • This desorbent is present in the bed prior to the adsorption step due to the prior performance of the desorption step.
  • the raffinate stream enters the rotary valve 2 and is then directed by the valve into line 24.
  • Line 24 carries the raffinate stream to a fractionation zone which is not shown in order to simplify the drawing. This may be a conventional or dividing wall column. Simultaneous to the adsorption procedure a stream of desorbent is continuously passed into the adsorbent chamber 14 via line 12.
  • the desorbent is distributed across the cross section of the column and moves downward through several beds of adsorbent which form a desorption zone.
  • the desorbent removes paraxylene and toluene from the adsorbent. This creates a mixture of paraxylene, toluene and desorbent which flows through the section of the adsorbent chamber functioning as the desorption zone.
  • This material is removed from the bottom of the chamber 14 and returned to the top of the chamber via a line not shown referred to in the art as the "pump around" line. This stream flows through more adsorbent at the top of the chamber forming the remainder of the desorption zone. It is then removed from the adsorbent chamber 14 via line 13 as the extract stream and passed into the rotary valve 2.
  • the rotary valve directs the extract stream of line 13 into line 15.
  • Line 15 delivers the extract stream into a first vertical fractionation zone occupying a large portion of the left hand side of the mid section of the fractional distillation column 6.
  • This fractionation zone contains 30-50 fractionation trays 21 and is separated from a parallel second fractionation zone occupying the other half of the column cross-section by a substantially fluid tight vertical wall 19.
  • the vertical wall is not necessarily centered in the column, and the two fractionation zones may differ in cross-sectional area or shape.
  • the vertical wall 19 divides a large vertical portion of the column 6 into two parallel fractionation zones. The two zones are isolated from each other for the height of this wall, but communicate at the top and bottom ends.
  • the toluene present in the extract stream of line 15 is driven upward in the first fractionation zone and enters the top of the column 6.
  • the top of the column is a purification zone which is designed to separate extract components from the toluene. This purification zone can also be used for a separation of different desorbent components when a multi-component desorbent stream is employed.
  • a toluene-rich vapor stream is removed from the top of column 6 via line 7 and passed through an overhead condenser not shown to form liquid delivered to the receiver 8.
  • a stream of liquid phase toluene is removed from the receiver and divided into a first portion which is returned to the top of the fractionation column 6 as reflux and a second portion which is removed from the process via line 25.
  • the term "rich" is intended to indicate a concentration of the indicated compound or class of compounds greater than 50 and preferably greater than 75 mol percent.
  • the bottom of column 6 also comprises an undivided fractionation zone. This zone can receive liquid draining from both the first and second fractionation zones. This liquid is subjected to fractional distillation which drives C 8 aromatic hydrocarbons upwards as vapor while concentrating the less volatile desorbent into a bottoms liquid removed via line 19. This separation is effected through the use of a reboiler not shown providing vapor to the bottom undivided fractionation zone.
  • the desorbent rich bottoms liquid is combined with a desorbent stream of line 22, which is obtained from the column receiving the raffinate of line 24.
  • the recovered desorbent is then passed to the rotary valve 2 via line 23 for reuse in the process.
  • the undivided bottom section of the column 6 is depicted as separated from the two parallel fractionation zones by a gas flow control or gas trap out tray 12 located just bellow the bottom of wall 19. A slight gap at this point allows horizontal liquid flow between the parallel fractionation zones.
  • This tray may have liquid sealed perforations allowing the normal downward flow of liquid, but its structure is such that the upward flow of vapor is at least greatly restricted.
  • the tray may totally block the upward vapor flow.
  • the use of this tray is preferred as it provides a means to positively control the division of the upward gas flow between the two fractionation zones, which is a prime means of controlling performance of the two zones.
  • the total vapor flow is, therefore, preferably removed from the column via line 16 and divided between lines 18 and 20 which feed the vapor to the bottom of the two parallel fractionation zones.
  • the gas flow may be controlled by one or more flow control valves or by adjusting the relative liquid levels in the bottom of the two zones. This is described in some detail in previously cited US-A-4,230,533 for a slightly different arrangement.
  • a preferred embodiment of the invention may, therefore, be characterized as a simulated moving bed adsorptive separation process for the separation of xylene isomers, which process comprises passing a feed stream comprising a para-xylene, meta-xylene and toluene into an adsorption zone comprising a bed of a selective adsorbent maintained at adsorption promoting conditions under which the para-xylene is selectively retained on the selective adsorbent, with toluene being also adsorbed onto the adsorbent to a lesser extent than paraxylene, and thus forming a raffinate stream comprising meta xylene; passing a desorbent into contact with said bed of the selective adsorbent, which has retained para-xylene and toluene under desorption promoting conditions to yield an extract stream comprising the desorbent compound, para-xylene and toluene; passing the extract stream into a dividing wall fractionation column operated at fractionation conditions and divided into at least
  • the trays of the base case include 50 in the extract column and 60 in the finishing column.
  • the dividing wall column requires a total reboiling duty of 93 MMBTU/hr versus 110 MMBTU/hr for the conventional column pair.
  • the dividing wall column requires a total condenser duty of 87 MMBTU/hr versus 109 for the standard two-column case.
  • Other economies are derived from a reduction in control systems, piping, pumps and plot space.
  • Operating conditions for adsorption include, in general, a temperature range of from 20 to 250°C, with from 60 to 200°C being preferred. Temperatures from 90°C to 160°C are highly preferred for the second adsorption zone.
  • Adsorption conditions also preferably include a pressure sufficient to maintain the process fluids in liquid phase; which may be from atmospheric to 600 psig.
  • Desorption conditions generally include the same temperatures and pressure as used for adsorption conditions. It is generally preferred that an SMB process is operated with an A:F flow rate through the adsorption zone in the broad range of 1:1 to 5:1.0 where A is the volume rate of "circulation" of selective pore volume in the adsorbent and F is the feed flow rate.
  • the practice of the subject invention requires no significant variation in operating conditions, adsorbent or desorbent composition within the adsorbent chambers. That is the adsorbent preferably remains at the same temperature throughout the process.
  • the success of a particular adsorptive separation is determined by many factors. Predominant in these factors are the composition of the adsorbent (stationary phase) and desorbent (mobile phase) employed in the process. The remaining factors are basically related to process conditions.
  • the subject process is not believed to be limited to use with any particular form of adsorbent.
  • the adsorbents employed in the process preferably comprise a molecular sieve such as a type A, X or Y zeolite or silicalite.
  • Silicalite is well described in the literature. It is disclosed and claimed in US-A-4,061 ,724. A more detailed description is found in the article, "Silicalite, A New Hydrophobic Crystalline Silica Molecular Sieve," Nature, Vol. 271, Feb. 9, 1978 which is incorporated herein by reference for its description and characterization of silicalite.
  • the active component of the adsorbents is normally used in the form of particle agglomerates having high physical strength and attrition resistance.
  • the agglomerates contain the active adsorptive material dispersed in an amorphous, inorganic matrix or binder, having channels and cavities therein which enable fluid to access the adsorptive material.
  • Methods for forming the crystalline powders into such agglomerates include the addition of an inorganic binder, generally a clay comprising a silicon dioxide and aluminum oxide, to a high purity adsorbent powder in a wet mixture.
  • the binder aids in forming or agglomerating the crystalline particles.
  • the blended clay-adsorbent mixture may be extruded into cylindrical pellets or formed into beads which are subsequently calcined in order to convert the clay to an amorphous binder of considerable mechanical strength.
  • the adsorbent may also be bound into irregular shaped particles formed by spray drying or crushing of larger masses followed by size screening.
  • the adsorbent particles may thus be in the form of extrudates, tablets, spheres or granules having a desired particle range, preferably from 1.9 mm to 250 microns (16 to 60 Standard U.S. Mesh).
  • Clays of the kaolin type, water permeable organic polymers or silica are generally used as binders.
  • the active molecular sieve component of the adsorbents will ordinarily be in the form of small crystals present in the adsorbent particles in amounts ranging from 75 to 98-wt.% of the particle based on volatile-free composition. Volatile-free compositions are generally determined after the adsorbent has been calcined at 900°C in order to drive off all volatile matter.
  • the remainder of the adsorbent will generally be the inorganic matrix of the binder present in intimate mixture with the small particles of the silicalite material. This matrix material may be an adjunct of the manufacturing process for the silicalite, for example, from the intentionally incomplete purification of the silicalite during its manufacture.
  • an adsorbent is often greatly influenced by a number of factors not related to its composition such as operating conditions, feed stream composition and the water content of the adsorbent.
  • the optimum adsorbent composition and operating conditions for the process are therefore dependent upon a number of interrelated variables.
  • One such variable is the water content of the adsorbent which is expressed herein in terms of the recognized Loss on Ignition (LOI) test.
  • LOI Loss on Ignition
  • the volatile matter content of the zeolitic adsorbent is determined by the weight difference obtained before and after drying a sample of the adsorbent at 500°C under an inert gas purge such as nitrogen for a period of time sufficient to achieve a constant weight.
  • the water content of the adsorbent results in an LOI at 900°C of less than 7.0% and preferably within the range of from 0 to 4.0 wt.%.
  • the hydration level of the sieve is normally controlled by controlled water injection, as via the desorbent stream.
  • the desorbent may be a mixture of two or more compounds.
  • a preferred desorbent for the separation of normal C 9 - C 11 paraffins from kerosene comprises a mixture of a normal paraffin and a cycloparaffin (naphthene).
  • a mixture in which the normal and cycloparaffins have the same carbon number is highly preferred, with carbon numbers of the desorbent compounds being in the general range of 5 to 8.
  • the preferred normal paraffin is n-hexane, and the desorbent may range from 0 to 100% normal paraffin.
  • the desorbent may also be 100% cycloparaffin.
  • the desorbents preferred for the separation of C 8 aromatic hydrocarbons differs from those preferred for paraffin separations.
  • the preferred "light" desorbent which is removed overhead in the subject process is toluene.
  • a preferred heavy desorbent is para-diethylbenzene, which may be used in admixture with a saturated hydrocarbon.
  • Other heavy desorbents for this separation include Indane and Indan derivatives, diethyltoluene and Tetralin derivatives as described in U.S. patent 5,107,062.
  • a related SMB processing technique is the use of "zone flush.”
  • the zone flush forms a buffer zone between the feed and extract bed lines to keep the desorbent e.g. normal pentane, from entering the adsorption zone. While the use of a zone flush requires a more complicated, and thus more costly rotary valve, the use of zone flush is preferred in the adsorption zones when high purity extract product are desired.
  • a quantity of the mixed component desorbent recovered overhead from the extract and/or raffinate columns is passed into a separate splitter column. A high purity stream of the lower strength component of the mixed component desorbent is recovered and used as the zone flush stream.
  • SMB Technology has been applied to a wide variety of chemicals in addition to those described above.
  • US-A-4,467,126 describes the recovery of a di-substituted benzene such as a nitrotoluene isomer.
  • the separation of 2,6 di methyl naphthalene is described in US-A-5,004,853 and 2,7 di isopropylnaphthalene in US-A-5,012,039.
  • SMB technology has been extended to the separation of sugars, to the separation of chiral compounds and to more complicated organics such as fatty acids and triglycerides as described in US-A- 5,225,580. It is believed the subject process can be applied to any such SMB process requiring desorbent recovery from extract or raffinate components, especially when a third component separable by fractionation is also present.
  • a “feed mixture” is a mixture containing one or more extract components and one or more raffinate components to be separated by the process.
  • feed stream indicates a stream of a feed mixture which is passed into contact with the adsorbent used in the process.
  • An “extract component” is a compound or class of compounds that is more selectively adsorbed by the adsorbent while a “raffinate component” is a compound or type of compound that is less selectively adsorbed.
  • desorbent material shall mean generally a material capable of desorbing an extract component from the adsorbent.
  • raffinate stream or "raffinate output stream” means a stream in which a raffinate component is removed from the adsorbent bed after the adsorption of extract compounds.
  • the composition of the raffinate stream can vary from essentially 100% desorbent material to essentially 100% raffinate components.
  • extract stream or "extract output stream” means a stream in which an extract material, which has been desorbed by a desorbent material, is removed from the adsorbent bed.
  • the composition of the extract stream can vary from essentially 100% desorbent material to essentially 100% extract components.
  • the extract stream may be rich in the desired compound or may only contain an increased concentration.
  • Zone I the adsorption zone.
  • Zone II liquid which contains the undesired isomer(s), that is, with raffinate.
  • This liquid is removed from the adsorbent in Zone II, referred to as a purification zone.
  • the undesired raffinate components are flushed from the void volume of the adsorbent bed by a material which is easily separated from the desired component by fractional distillation.
  • Zone III of the adsorbent chamber(s) the desired isomer is released from the adsorbent by exposing and flushing the adsorbent with the desorbent (mobile phase). The released desired component and accompanying desorbent are removed from the adsorbent in the form of the extract stream.
  • Zone IV is a portion of the adsorbent located between Zones I and III which is used to segregate Zones I and III.
  • desorbent is partially removed from the adsorbent by a flowing mixture of desorbent and undesired components of the feed stream. The liquid flow through Zone IV prevents contamination of Zone III by Zone I liquid by flow cocurrent to the simulated motion of the adsorbent from Zone III toward Zone I.
  • upstream and downstream are used herein in their normal sense and are interpreted based upon the overall direction in which liquid is flowing in the adsorbent chamber. That is, if liquid is generally flowing downward through a vertical adsorbent chamber, then upstream is equivalent to an upward or higher location in the chamber.

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

Abstract

Il est possible de réduire les frais de construction et de fonctionnement occasionnés par la récupération du produit d'extrait ou de raffinat d'une unité de traitement de séparation par adsorption à lit mobile simulé, en utilisant une colonne à cloison pour réaliser la séparation. Le système de raffinat ou d'extrait est passé dans la colonne, à un point intermédiaire situé sur le premier côté de la cloison, la colonne distribuant le produit de séparation par adsorption faisant office d'organe de soutirage latéral depuis le côté opposé de la cloison. Un flux d'impuretés coadsorbées est retiré en un flux de distillat de tête, et un désorbant est récupéré en un flux net de queue de distillation.
EP01992181A 2001-12-18 2001-12-18 Recuperation de produit de separation par adsorption au moyen de la distillation fractionnee Withdrawn EP1458662A1 (fr)

Applications Claiming Priority (1)

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PCT/US2001/049104 WO2003051799A1 (fr) 2001-12-18 2001-12-18 Recuperation de produit de separation par adsorption au moyen de la distillation fractionnee

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EP1458662A1 true EP1458662A1 (fr) 2004-09-22

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EP (1) EP1458662A1 (fr)
JP (1) JP2005511773A (fr)
KR (1) KR100845665B1 (fr)
CN (1) CN1297524C (fr)
AU (1) AU2002232649A1 (fr)
WO (1) WO2003051799A1 (fr)

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CN113321569B (zh) * 2021-05-31 2022-08-26 烟台大学 一种萃取精馏分离异丙醚、异丙醇和水的方法
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CN1582266A (zh) 2005-02-16
KR20040075881A (ko) 2004-08-30
CN1297524C (zh) 2007-01-31
JP2005511773A (ja) 2005-04-28
KR100845665B1 (ko) 2008-07-10
AU2002232649A1 (en) 2003-06-30
WO2003051799A1 (fr) 2003-06-26

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