EP2376225A1 - Variation de l imprégnation en étain d un catalyseur pour la déshydrogénation d alcanes - Google Patents

Variation de l imprégnation en étain d un catalyseur pour la déshydrogénation d alcanes

Info

Publication number
EP2376225A1
EP2376225A1 EP09798881A EP09798881A EP2376225A1 EP 2376225 A1 EP2376225 A1 EP 2376225A1 EP 09798881 A EP09798881 A EP 09798881A EP 09798881 A EP09798881 A EP 09798881A EP 2376225 A1 EP2376225 A1 EP 2376225A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
dehydrogenation
shaped body
tin
oxide
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.)
Ceased
Application number
EP09798881A
Other languages
German (de)
English (en)
Inventor
Muhammad Iqbal Mian
Max Heinritz-Adrian
Sascha Wenzel
Oliver Noll
Meinhard Schwefer
Helmut Gehrke
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.)
ThyssenKrupp Industrial Solutions AG
Original Assignee
Uhde GmbH
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
Priority claimed from DE102008062782A external-priority patent/DE102008062782A1/de
Priority claimed from DE102009056539A external-priority patent/DE102009056539A1/de
Application filed by Uhde GmbH filed Critical Uhde GmbH
Publication of EP2376225A1 publication Critical patent/EP2376225A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
    • B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
    • B01J23/626—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with tin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0207—Pretreatment of the support
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
    • C07C5/333—Catalytic processes
    • C07C5/3335—Catalytic processes with metals
    • C07C5/3337—Catalytic processes with metals of the platinum group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/005—Spinels
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of zinc, cadmium or mercury
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of germanium, tin or lead
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/42—Platinum
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • the invention relates to a catalyst, the preparation of the catalyst and a method with this catalyst for the dehydrogenation of alkanes or alkyl substituents of hydrocarbons.
  • the dehydrogenation of hydrocarbons usually takes place in reactors, wherein a holding device is mounted with a suitable catalyst, and flows around a catalyst to be reacted mixture of hydrocarbons catalyst.
  • the catalyst should be designed so that it offers the largest possible surface area for the gas mixture flowing around.
  • a catalyst is a solid of, for example, cylinders, spheres, foams, or any other suitable form.
  • the shaped body may also contain catalytic substances for the dehydrogenation of hydrocarbons.
  • additional catalytic substances are applied by various methods on the surface of the moldings.
  • a catalyst is generally prepared by different methods.
  • First, the molded article is made, with the selected solids undergoing a shaping process such as sintering, pelleting, tabletting, molding or extrusion after milling, mixing.
  • a shaping process such as sintering, pelleting, tabletting, molding or extrusion after milling, mixing.
  • additional process steps such as drying and calcination can be used.
  • impregnation can be used to apply solution containing catalytic materials to the molding, and this process step can be repeated if desired.
  • After the impregnation step usually follow other steps such as drying, calcination, washing and repeated drying.
  • the patent EP 0559 509 B1 describes a process for the dehydrogenation of aliphatic saturated hydrocarbons, wherein a dehydrogenation catalyst is used which comprises at least one oxide of an element from Groups IIA, IIB, IMA, HIB, IVA and IVB of the Periodic Table, at least one Precious metal of the platinum family, containing at least one additional metal from the elements of group VIIB or IVA and at least one alkali or alkaline earth metal.
  • the catalyst also includes halogenated compounds and sulfur.
  • the impregnation step is followed by a washing process. Chloride ions are undesirable on the catalyst as they may damage equipment due to their corrosivity during the reaction.
  • the wash solution used is deionized water.
  • the support may be stabilized with calcium oxide, graphite, stearic acid or polyethylene.
  • Catalysts have the properties to reduce the activation energy of the reactants involved in a chemical reaction, and thus to accelerate the chemical reaction. In practice, however, the catalysts become ineffective by side reactions after some time of use, which of course will lead to a reduction in the reaction conversion. In the catalytic dehydrogenation of alkanes occur after a certain reaction time methane, ethane, carbon dioxide and other unwanted by-products, which later have to be separated from the product stream by complex processes. Another byproduct is coke formation on the catalyst, which greatly affects the activity of the catalyst. Therefore, much has been done in the prior art to increase the selectivity of the catalyst, thereby suppressing the Mauillonbil- fertil as possible, or to extend the service life of the catalyst.
  • GB 1346856 A discloses a process for the dehydrogenation of alkanes in the presence of water vapor.
  • the alkane to be dehydrogenated is passed over a catalyst which is supported on a support of zinc aluminate and tin dioxide and which is reacted with a compound of a metal from group VIII B of the periodic table. is soaked.
  • Examples are the metals nickel, platinum, ruthenium, rhodium, palladium, osmium, iridium or mixtures thereof.
  • the catalyst may also contain for activation compounds from the group of alkali metals, alkaline earth metals, or the germanium or tin compounds. Detection of tin compounds contained in the catalyst is not described.
  • the invention is therefore based on the object to produce a powerful catalyst with higher selectivity and longer life and to provide a method with this catalyst for the dehydrogenation of alkanes with little by-product formation and higher selectivity of the products over the prior art ,
  • the object is achieved in that a catalyst for the dehydrogenation of alkanes or alkyl substituents of hydrocarbons containing
  • a shaped body consisting of at least one or more oxides of elements of II. to IV. Main or subgroup of the Periodic Table or an oxide mixed compound constructed thereof; wherein the constituents serve as base material of the shaped body;
  • an additive component comprising an oxide of an element of IV. main group of the periodic table, which is added during the molding process;
  • an active surface component comprising a platinum compound
  • an additional surface component which includes a compound of an element of IV. Main Group of the Periodic Table.
  • a catalyst for carrying out a catalytic alkane dehydrogenation, the catalyst being based on a shaped body.
  • the shaped body consists of at least one or more oxides of elements of II. To IV. Main or subgroup of the Periodic Table or an oxide mixed compound constructed thereof. This mixture of compounds serves as base materials of the molded article. The content of the base materials can make up more than 90% of the components of the catalyst.
  • the additive component selected from an oxide of an element of main group IV of the Periodic Table with a minor proportion of 0.1% to 4% of the catalyst, is added during the shaping process. With the additional catalytically active substances of a platinum compound and with a compound of an element of the IV. Main group of the Periodic Table as a surface component of the catalyst of the invention is rounded off.
  • a preferred base material of the shaped body for the catalyst for the dehydrogenation of alkanes or alkyl substituents of hydrocarbons is zinc oxide with aluminum oxide (zinc aluminate).
  • This compound can be prepared, for example, by a calcination process of zinc oxide and alumina in a high-temperature furnace, with more than 50% being the major constituent of the catalyst.
  • the compound zinc aluminate can also be prepared, for example, by a precipitation reaction from an aqueous or alcoholic mixture of a zinc salt solution with an aluminum salt solution.
  • moldings which are built up with aluminum oxide, calcium oxide, zinc oxide, zirconium dioxide, magnesium dioxide or silicon dioxide as the main constituent are also suitable.
  • the molding material may also consist of mixed phases of selected substances of the aforementioned list. Of course, a combination of the materials within the scope claimed above may also be used as a molding material.
  • an oxide of an element of the IV. Main group of the Periodic Table tin dioxide is preferred.
  • the additional component has a low concentration in the molding, however, it can detect the characteristic reflection angles of 26.6 °, 33.8 ° and 51, 7 ° noticeable in the X-ray diffraction with the wavelength Cu-K 0 .
  • tin dioxide is uniformly distributed over the entire shaped body.
  • Catalytically active surface components on the molding additionally increase the service life of the catalyst during operation, on the one hand, the platinum compound with 0.01 to 1.0 mass percent of platinum and on the other hand tin in the form of a compound of an element of the IV.
  • Main group of the Periodic Table with the Proportion of 0.1 to 4.0 mass percent are preferred.
  • the additional surface component may also be germanium.
  • Sintering, pelletizing, tableting, prilling or extrusion process are examples of suitable shaping processes, the optimum shape of the shaped body being chosen depending on the holding device of the catalyst and / or of the reactor.
  • the shaped body After the molding process, the shaped body must optionally be calcined or dried. Only then can the active and additional catalytic surface components be applied to the molding by means of impregnation, precipitation or impregnation, for example in the form of salt in aqueous solution, simultaneously or consecutively. If necessary, the process steps can be repeated.
  • an oxidic compound is preferred for the shaped body.
  • the solids of the oxidic compounds are pulverized, mixed with binders and subjected to a shaping process.
  • Further favored variants for the shaped body are also a water-soluble tin salt and one or more water-soluble salts of the metals aluminum zinc calcium or magnesium.
  • the aqueous or alcoholic solutions are optionally mixed with deionized water, neutralized and precipitated. After precipitation, the material thus obtained is filtered, dried and processed by a suitable shaping process to the desired shaped body.
  • Well-suited forming processes are typically tableting or extrusion. The type of shaping process is left to the skilled person. The goal is usually to obtain an abrasion-resistant molded body with sufficiently high porosity.
  • a platinum compound which is particularly suitable for impregnation is hexachloroplatinic acid or its salts.
  • other soluble platinum compounds such as platinum (II) halides, platinum (IV) halides are also operational.
  • a compound of an element of IV Main group of the periodic table, a water-soluble tin compound such as stannous chloride or stannous nitrate is gladly taken.
  • a water-soluble tin compound such as stannous chloride or stannous nitrate is gladly taken.
  • the impregnation of the molding with the specified surface component in solutions can be carried out consecutively or simultaneously.
  • the impregnation is typically carried out by spraying or impregnating the shaped body with the solution containing the catalytically active substances.
  • other methods are suitable as impregnation, which ensure a uniform distribution of the substances to be impregnated on the molding.
  • the molding undergoes, as needed, the subsequent process steps calcination, washing and / or drying. Some process steps can also be repeated. Thereafter, the desired catalyst is finished.
  • a process for the dehydrogenation of alkanes or alkyl substituents of hydrocarbons is also claimed wherein an alkane or hydrocarbon to be dehydrogenated is passed in admixture with quasi-inert gases through a dehydrogenation reactor charged with the catalyst of the invention.
  • a dehydrogenation reactor charged with the catalyst of the invention.
  • the usual conditions of alkane dehydrogenation are used.
  • the alkane dehydrogenation is carried out at a temperature of 480 to 820 0 C.
  • the reaction produces the desired alkene and hydrogen, with the alkene being taken out, and unreacted alkane and water vapor being recycled through the reactor.
  • This reaction step is preferably carried out adiabatically or allothermally with external heating. In principle, however, any method and / or device which can carry out such a dehydrogenation reaction is suitable.
  • Suitable quasi-inert gases are, for example, water vapor, carbon dioxide or nitrogen. It is also common in some processes to add hydrogen to suppress coking.
  • the catalyst according to the invention By carrying out the process with the catalyst according to the invention, one obtains, depending on the reaction carried out, improved conversions and thus an increased reaction rate. In particular, however, one obtains improved selectivity, which corresponds to a reduced formation of by-products. This also requires less catalyst.
  • the catalyst according to the invention also has a significantly increased service life. This also contributes to lower operating costs of the entire process.
  • the alkane dehydrogenation process step with a subsequent hydrogen combustion process step and to use the catalyst according to the invention.
  • the hydrogen is removed from the equilibrium and this shifted in the desired direction, on the other hand thereby heat whereby the gas can be redirected through the dehydrogenation reactor without further heating to react unreacted alkane.
  • This process step is preferably carried out at a temperature of 480 to 820 0 C.
  • the hydrogen is lyst oxidized at a temperature of 480-820 0 C. Since the hydrogen combustion is exothermic, the heat that develops in this process step for the further endothermic dehydrogenation can be used.
  • the catalyst Due to a slight but steady coking, the catalyst must nevertheless be regenerated at regular intervals. This is usually done by passing an oxygen-containing gas, whereby the carbonaceous deposits are burned on the catalyst.
  • the first shaped body which is the basis of variants (1) and (2), contains 0.95% tin.
  • the variant (1) contains no additional impregnated tin
  • the variant (2) contains 0.48% tin, which was applied together with the platinum.
  • the variant (2) shows over variant (1) a higher selectivity.
  • the second shaped body which forms the basis of variants (3) and (4), contains no tin.
  • the variant (3) with an impregnated tin content of 0.95%, which corresponds to the tin content of variant (1) shows in comparison to this also a significant increase in the selectivity at the same conversion, but remains below the selectivity of variant (2).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

L’invention concerne un catalyseur servant à la déshydrogénation des alcanes ou des substituants alkyl d’hydrocarbures, comprenant un corps moulé qui est composé d’au moins un ou de plusieurs oxydes d’éléments du deuxième au quatrième groupe principal ou auxiliaire de la classification périodique ou d’un mélange d’oxydes produit à partir de ces derniers. Les constituants sont utilisés comme matériau de base du corps moulé ; on ajoute au cours du processus de formage un composant additionnel qui contient un oxyde d’un élément du quatrième groupe principal de la classification périodique ; et on sélectionne un composé platine et un composé d’un élément du quatrième groupe principal de la classification périodique en tant que composant de surface du catalyseur. L’invention concerne également la fabrication du catalyseur avec les matériaux revendiqués au moyen des différentes étapes du procédé, ainsi qu’un procédé de déshydrogénation d’alcanes utilisant le catalyseur selon l’invention.
EP09798881A 2008-12-18 2009-12-15 Variation de l imprégnation en étain d un catalyseur pour la déshydrogénation d alcanes Ceased EP2376225A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102008062782A DE102008062782A1 (de) 2008-12-18 2008-12-18 Variation der Zinnimprägnierung eines Katalysators zur Alkandehydrierung
DE102009056539A DE102009056539A1 (de) 2009-12-03 2009-12-03 Variation der Zinnimprägnierung eines Katalysators zur Alkandehydrierung
PCT/EP2009/008976 WO2010069548A1 (fr) 2008-12-18 2009-12-15 Variation de l’imprégnation en étain d’un catalyseur pour la déshydrogénation d’alcanes

Publications (1)

Publication Number Publication Date
EP2376225A1 true EP2376225A1 (fr) 2011-10-19

Family

ID=42084540

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09798881A Ceased EP2376225A1 (fr) 2008-12-18 2009-12-15 Variation de l imprégnation en étain d un catalyseur pour la déshydrogénation d alcanes

Country Status (15)

Country Link
US (1) US20110301392A1 (fr)
EP (1) EP2376225A1 (fr)
JP (1) JP2012512015A (fr)
KR (1) KR20110097953A (fr)
CN (1) CN102256702A (fr)
AR (1) AR074809A1 (fr)
BR (1) BRPI0917752A2 (fr)
CA (1) CA2747085A1 (fr)
CL (1) CL2011001494A1 (fr)
EA (1) EA023151B1 (fr)
EG (1) EG27110A (fr)
MX (1) MX2011006487A (fr)
MY (1) MY191090A (fr)
WO (1) WO2010069548A1 (fr)
ZA (1) ZA201105242B (fr)

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WO2014118194A2 (fr) 2013-01-29 2014-08-07 IFP Energies Nouvelles Catalyseur comprenant des oxydes mixtes des éléments aluminium, zinc et manganèse et son utilisation en déshydrogenation
KR101477413B1 (ko) * 2013-07-30 2014-12-29 삼성토탈 주식회사 노르말-부탄의 직접 탈수소화 반응용 백금-주석-금속-알루미나 촉매의 제조방법 및 상기 촉매를 이용한 c4 올레핀의 제조방법
JP6446033B2 (ja) * 2014-03-31 2018-12-26 三井化学株式会社 不飽和炭化水素の製造方法
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JP7064896B2 (ja) * 2018-02-15 2022-05-11 Ｅｎｅｏｓ株式会社 不飽和炭化水素の製造方法
BR112023025118A2 (pt) 2021-06-02 2024-02-20 Exxonmobil Chemical Patents Inc Processos para regeneração de catalisadores e para aperfeiçoamento de alcanos e/ou hidrocarbonetos alquil aromáticos

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Also Published As

Publication number Publication date
BRPI0917752A2 (pt) 2019-09-24
ZA201105242B (en) 2012-03-28
MY191090A (en) 2022-05-30
EG27110A (en) 2015-06-16
EA201190060A1 (ru) 2012-01-30
MX2011006487A (es) 2011-09-30
WO2010069548A1 (fr) 2010-06-24
EA023151B1 (ru) 2016-04-29
CL2011001494A1 (es) 2011-10-28
KR20110097953A (ko) 2011-08-31
JP2012512015A (ja) 2012-05-31
AR074809A1 (es) 2011-02-16
CN102256702A (zh) 2011-11-23
WO2010069548A4 (fr) 2010-08-19
CA2747085A1 (fr) 2010-06-24
US20110301392A1 (en) 2011-12-08

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