US20050171218A1 - Process for the conversion of a synthesis gas to hydrocarons in the presence of beta-SiC and effluent from this process - Google Patents

Process for the conversion of a synthesis gas to hydrocarons in the presence of beta-SiC and effluent from this process Download PDF

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US20050171218A1
US20050171218A1 US11/027,706 US2770605A US2005171218A1 US 20050171218 A1 US20050171218 A1 US 20050171218A1 US 2770605 A US2770605 A US 2770605A US 2005171218 A1 US2005171218 A1 US 2005171218A1
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mol
hydrocarbons
process according
catalyst
hydrocarbon effluent
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Sabine Savin-Poncet
Marc-Jacques Ledoux
Cuong Pham-Huu
Jacques Bousquet
Behrang Madani
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Total Marketing Services SA
TotalEnergies SE
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Total SE
Total France SA
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Assigned to TOTAL FRANCE, TOTAL S.A. reassignment TOTAL FRANCE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SAVIN-PONCET, SABINE, LEDOUX, MARC-JACQUES, MADANI, BEHRANG, PHAM-HUU, CUONG, BOUSQUET, JACQUES
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Priority to US11/411,085 priority Critical patent/US7393877B2/en
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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
    • C10G2/00—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon
    • C10G2/30—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen
    • C10G2/32—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts
    • C10G2/33—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts characterised by the catalyst used
    • C10G2/331—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts characterised by the catalyst used containing group VIII-metals
    • C10G2/332—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts characterised by the catalyst used containing group VIII-metals of the iron-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
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/75—Cobalt
    • 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
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/88—Molybdenum
    • B01J23/882—Molybdenum and cobalt
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B01J27/22—Carbides
    • B01J27/224—Silicon carbide
    • 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
    • B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
    • 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
    • B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
    • B01J35/56—Foraminous structures having flow-through passages or channels, e.g. grids or three-dimensional monoliths
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/02—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon from oxides of a carbon
    • C07C1/04—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon from oxides of a carbon from carbon monoxide with hydrogen
    • C07C1/0425—Catalysts; their physical properties
    • C07C1/043—Catalysts; their physical properties characterised by the composition
    • C07C1/0435—Catalysts; their physical properties characterised by the composition containing a metal of group 8 or a compound thereof
    • 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
    • C10G2/00—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon
    • C10G2/30—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen
    • C10G2/32—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts
    • C10G2/33—Production of liquid hydrocarbon mixtures of undefined composition from oxides of carbon from carbon monoxide with hydrogen with the use of catalysts characterised by the catalyst used
    • 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
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
    • C07C2523/28—Molybdenum
    • 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
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/75—Cobalt
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/20—Carbon compounds
    • C07C2527/22—Carbides
    • C07C2527/224—Silicon carbide

Definitions

  • the present invention relates to a process for the conversion of synthesis gas to C 2 + hydrocarbons by Fischer-Tropsch synthesis. It also relates to a Fischer-Tropsch synthesis process which produces an effluent exhibiting a specific distribution of the liquid fraction, and to this effluent.
  • U.S. Pat. Nos. 5,648,312, 5,677,257 and 5,710,093 disclose a specific catalytic support suitable for the FT synthesis (capable of being employed in a fixed bed, an ebullating bed or as a slurry).
  • the catalytic entity in these documents is a metal from Group IVB or VIII, or a mixture, in particular zirconium and cobalt.
  • This support is obtained in particular by the formation of a suspension of silica and of silicon carbide in a basic solution, the formation of drops and then their separation as spheres, and then the transfer of the spheres into an acidic solution to result in a catalytic support comprising a substantially homogeneous mixture of silica and of SiC.
  • a catalytic support comprising a substantially homogeneous mixture of silica and of SiC.
  • Processes for the synthesis of hydrocarbons from synthesis gas use this catalytic support, which is a homogeneous mixture of particles of silica and of SiC, in an amount of 10 to 50% of the support, the support having a specific surface of at least approximately 30 m 2 /g (preferably of greater than 40 m 2 /g), mean pore diameters of at least approximately 150 ⁇ and a particle size of at least 0.1 mm.
  • the SiC necessarily has the alpha form in these documents, the binder of this SiC being the silica.
  • the specific surface is conferred by the silica binder rather than by the form of the SiC; the latter is used in fact more as a heat sink rather than as a support as such.
  • silica and/or of alumina as binder can have a negative effect on the thermal conductivity of the support.
  • this binder, as support additionally exhibits the disadvantage of reacting with the catalytic entity, thus resulting in a loss in the activity over time.
  • the invention provides a novel FT synthesis process using a novel catalytic support comprising ⁇ -SiC.
  • a support is thus obtained which, in comparison with the supports of the prior art, is particularly suitable for the exothermic reaction of the FT synthesis.
  • the invention provides a process for the conversion of carbon monoxide to C 2 + hydrocarbons in the presence of hydrogen and of a catalyst comprising a metal and a support comprising silicon carbide, characterized in that the support comprises more than 50% by weight of silicon carbide in the beta form.
  • a further subject-matter of the invention is a process for the conversion of carbon monoxide to C 2 + hydrocarbons in the presence of hydrogen and of a catalyst, characterized in that the hydrocarbon effluent comprises more than 70 mol % of a mixture comprising from 50 to 90 mol % of C 6 to C 12 hydrocarbons and from 10 to 50 mol % of C 13 to C 24 hydrocarbons.
  • a further subject-matter of the invention is a C 2 + hydrocarbon effluent comprising hydrocarbons, methane and CO 2 which comprises more than 70 mol % of a mixture comprising from 50 to 90 mol % of C 6 to C 12 hydrocarbons and from 10 to 50 mol % of C 13 to C 24 hydrocarbons.
  • FIG. 1A gives the results of the yields of the various fractions as a function of the time under flow for a first embodiment
  • FIG. 1B gives the distribution of the hydrocarbons within the liquid fraction for this first embodiment
  • FIG. 2A gives the results of the yields of the various fractions as a function of the time under flow for a second embodiment
  • FIG. 2B gives the distribution of the hydrocarbons within the liquid fraction for the second embodiment
  • FIGS. 3A and 3B give the results of the yields of the various fractions as a function of the time under flow for third and fourth embodiments;
  • FIG. 4A gives the results of the yields of the various fractions as a function of the time under flow for a fifth embodiment
  • FIG. 4B gives the distribution of the hydrocarbons within the liquid fraction for this fifth embodiment.
  • the beta-SiC is prepared by a gas/solid reaction between intimately mixed (without liquid) SiO vapour and solid carbon.
  • ⁇ -SiC For further details with regard to the ⁇ -SiC, reference may be made to the following patent applications and patents, incorporated by reference in the present application: EP-A-0 313 480, EP-A-0 440 569, U.S. Pat. No. 5,217,930, EP-A-0 511 919, EP-A-0 543 751 and EP-A-0 543 752.
  • the ⁇ -SiC is characterized in particular in that it exists in the pure state without binder.
  • the crystals are of face-centred cubic type.
  • the specific surface of the ⁇ -SiC is between 5 and 40 m 2 /g and preferably between 10 and 25 m 2 /g.
  • the ⁇ -SiC can be prepared in the form of a powder, grains, extrudates (without binder), foam, monolith, and the like.
  • the size of the SiC can vary according to the type of process employed (fixed bed, ebullating bed, slurry bed). It is thus possible, according to one alternative form, to use a size of between 0.1 and 20 mm, preferably between 1 and 15 mm. According to another alternative form, it is possible to use a size of between 1 and 200 ⁇ m, preferably between 5 and 150 ⁇ m.
  • This ⁇ -SiC has very good mechanical properties. Because of its very good thermal conductivity, generally much greater than that of metal oxides, hot spots are limited to the surface of the catalyst. The selectivity is thus improved.
  • the support of the catalyst comprises from 50 to 100% by weight of beta silicon carbide in the particulate state and preferably 100% of the said silicon carbide.
  • Use may conventionally be made, as main metal catalyst, of metals from Group VIII, for example in particular cobalt, iron or ruthenium, cobalt being particularly preferred.
  • Use may also be made conventionally, at the same time, of a promoter. Mention may be made, among the promoters, of another metal from Group VIII or also of metals chosen from the group consisting of Zr, K, Na, Mn, Sr, Cu, Cr, W, Re, Pt, Ir, Rh, Pd, Ru, Ta, V, Mo and their mixtures. Mo is preferred.
  • the content of main metal, in particular cobalt, is conventionally greater than 5%, typically between 10 and 50%, of the final weight of the catalyst, in particular between 20 and 35% by weight.
  • the content of promoter, in particular molybdenum, is conventionally between 0.1 and 15% of the final weight of the catalyst, in particular between 2 and 10% by weight.
  • a primary metal/promoter ratio by weight is conventionally from 10:1 to 3:1.
  • the catalytic metal is deposited conventionally.
  • use may be made of the impregnation of the pore volume by a salt of the metal, for example cobalt nitrate.
  • Use may also be made of the evaporated drop (also known as egg shell) method, by dropwise addition of a metal salt solution at ambient temperature to a support at high temperature, resulting in deposition essentially at the surface, for example a cobalt nitrate solution under air to a support at 200° C.
  • the catalytic bed can be fixed, ebullating or as a slurry.
  • a fixed bed will be preferred.
  • the Fischer-Tropsch synthesis reaction is generally carried out under the following operating conditions:
  • the present invention also relates to an FT synthesis process which produces a hydrocarbon effluent which comprises at least 70 mol % of C 5 to C 25 hydrocarbons and in which the distribution is centred around relatively light hydrocarbons, approximately from C 7 to C 10 .
  • This type of distribution is not conventional, in particular for a process carried out in a fixed bed.
  • the hydrocarbon effluent comprises more than 70 mol % of a mixture comprising from 50 to 90 mol % of C 6 to C 12 hydrocarbons and from 10 to 50 mol % of C 13 to C 24 hydrocarbons.
  • the hydrocarbon effluent comprises at most 10 mol % of branched hydrocarbons and olefins and/or less than 2 mol % of C 1 to C 20 alcohol.
  • the content of methane and of CO 2 is less than 20 mol %.
  • Another subject-matter of the invention is this specific FT synthesis effluent.
  • the support based on ⁇ -SiC in the form of grains with a diameter of between 0.4 and 1 mm, is impregnated by the pore volume method with an aqueous solution comprising the cobalt salt in the nitrate form.
  • the weight of the precursor salt is calculated in order to have a final cobalt charge of 30% by weight with respect to the weight of catalyst after calcination and reduction.
  • the impregnated product is subsequently dried under air at 100° C. for 2 h and then calcined under air at 350° C. for 2 h, in order to convert the precursor salt to its corresponding oxide.
  • the product after calcination is reduced under a stream of hydrogen at 400° C. for 2 h in order to obtain the metallic form of the active phase.
  • the Fischer-Tropsch synthesis reaction is carried out under the following conditions:
  • FIG. 1A The results obtained, expressed in terms of yields of the various fractions, are presented in FIG. 1A as a function of the time under flow.
  • the catalyst based on Co/P-SiC exhibits a very good activity for the formation of liquid hydrocarbons from the CO/H 2 mixture.
  • the distribution of the hydrocarbons within the liquid fraction (C 4 + ) is presented in FIG. 1 B. From the results obtained, the liquid fraction is essentially composed of paraffin hydrocarbons ranging from C 6 to C 25 , i.e.
  • the support based on ⁇ -Sic in the form of grains with a diameter of between 0.4 and 1 mm, is impregnated by the pore volume method with an aqueous solution comprising the cobalt salt in the nitrate form and an aqueous solution comprising an ammonium molybdate tetrahydrate.
  • the weight of the precursor salt is calculated in order to have a final cobalt charge of 30% by weight with respect to the weight of the catalyst and a molybdenum charge of 5% by weight with respect to the weight of the catalyst, after calcination and reduction.
  • the preparation of the catalyst is the same as in Example 1.
  • the Fischer-Tropsch synthesis reaction is carried out under the same conditions as in Example 1.
  • the concentration of the olefinic and branched hydrocarbons likewise remains low (less than 1% on average).
  • the support based on ⁇ -SiC is identical to that of Example 2.
  • the Fischer-Tropsch synthesis reaction is carried out under the following conditions:
  • the yield of the fraction comprising liquid hydrocarbons is always higher compared with that obtained in the absence of molybdenum on the catalyst, this being the case whatever the reaction temperature.
  • the presence of molybdenum reduces the formation of the light products, such as CO 2 and CH 4 , and promotes the formation of the liquid hydrocarbons, this being the case whatever the reaction temperature, i.e. 200° C. or 210° C. It should also be noted that, in the presence of molybdenum, the activity in the Fischer-Tropsch synthesis of the catalyst is more stable than in the absence of molybdenum.
  • the support based on ⁇ -SiC in the form of a monolith with a mean cell opening size of approximately 500 ⁇ m, is impregnated by the pore volume method with an aqueous solution comprising the cobalt salt in the nitrate form.
  • the impregnation process is the same as in Example 1.
  • the Fischer-Tropsch synthesis reaction is carried out under the following conditions:
  • FIG. 4A The results obtained, expressed in terms of yields of the various fractions, are presented in FIG. 4A as a function of the time under flow.
  • FIG. 4B gives the distribution of the hydrocarbons within the liquid fraction (C 4 + ).
  • the yield of liquid products remains high despite the reaction temperature of 220° C. This is attributed to the high thermal conductivity of the support based on ⁇ -SiC, which prevents hot spots and improves the selectivity.
  • the results are of the same nature as those obtained in Example 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US11/027,706 2003-12-31 2005-01-03 Process for the conversion of a synthesis gas to hydrocarons in the presence of beta-SiC and effluent from this process Abandoned US20050171218A1 (en)

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FR0315622A FR2864532B1 (fr) 2003-12-31 2003-12-31 Procede de transformation d'un gaz de synthese en hydrocarbures en presence de sic beta et effluent de ce procede
FR0315622 2003-12-31

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US11/411,085 Expired - Fee Related US7393877B2 (en) 2003-12-31 2006-04-26 Process for the conversion of a synthesis gas to hydrocarbons in the presence of beta-SiC and effluent from this process

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US (2) US20050171218A1 (de)
EP (1) EP1702025B1 (de)
JP (1) JP4833856B2 (de)
AR (1) AR048578A1 (de)
AT (1) ATE499429T1 (de)
AU (1) AU2004314967B2 (de)
BR (1) BRPI0417920B1 (de)
CA (1) CA2549036C (de)
DE (1) DE602004031558D1 (de)
ES (1) ES2363856T3 (de)
FR (1) FR2864532B1 (de)
MX (1) MXPA06007480A (de)
PE (1) PE20051044A1 (de)
PT (1) PT1702025E (de)
RU (1) RU2356934C2 (de)
WO (1) WO2005073345A1 (de)

Cited By (2)

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US20060194888A1 (en) * 2003-12-31 2006-08-31 Total France Process for the conversion of a synthesis gas to hydrocarbons in the presence of beta-SiC and effluent from this process
WO2012038621A1 (fr) 2010-09-23 2012-03-29 Centre National De La Recherche Scientifique (C.N.R.S.) Procédé utilisant un réacteur à plaques pour la synthèse fischer-tropsch

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Publication number Priority date Publication date Assignee Title
FR2887545B1 (fr) * 2005-06-27 2007-08-10 Total Sa Procede de transformation d'un gaz de synthese en hydrocarbures en presence de mousse de sic
EP2204235A1 (de) 2008-12-19 2010-07-07 Total Petrochemicals Research Feluy Katalysator und Verfahren zur selektiven Hydrierung von Alkinen und Dienen
EP2204236A1 (de) 2008-12-19 2010-07-07 Total Petrochemicals Research Feluy Katalysator und Verfahren zur Hydrierung von Kohlenwasserstoff-Ausgangsmaterialien
WO2014140973A1 (en) 2013-03-14 2014-09-18 Sasol Technology (Pty) Limited A hydrocarbon synthesis process using a cobalt-based catalyst supported on a silicon carbide comprising support
WO2014207096A1 (en) 2013-06-27 2014-12-31 Sicat Method for manufacturing shaped beta-sic mesoporous products and products obtained by this method

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WO2005073345A1 (fr) 2005-08-11
RU2356934C2 (ru) 2009-05-27
ES2363856T3 (es) 2011-08-18
US20060194888A1 (en) 2006-08-31
DE602004031558D1 (de) 2011-04-07
FR2864532B1 (fr) 2007-04-13
PT1702025E (pt) 2011-05-25
CA2549036A1 (fr) 2005-08-11
AU2004314967B2 (en) 2011-12-01
BRPI0417920B1 (pt) 2014-08-26
AU2004314967A1 (en) 2005-08-11
FR2864532A1 (fr) 2005-07-01
EP1702025B1 (de) 2011-02-23
RU2006125385A (ru) 2008-02-10
JP2007517101A (ja) 2007-06-28
CA2549036C (fr) 2012-08-07
BRPI0417920A (pt) 2007-04-10
ATE499429T1 (de) 2011-03-15
JP4833856B2 (ja) 2011-12-07
AR048578A1 (es) 2006-05-10
MXPA06007480A (es) 2007-01-26
EP1702025A1 (de) 2006-09-20

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