AR080756A1 - Deshidratacion e isomerizacion esqueletica simultaneas de isobutanol en catalizadores acidos - Google Patents
Deshidratacion e isomerizacion esqueletica simultaneas de isobutanol en catalizadores acidosInfo
- Publication number
- AR080756A1 AR080756A1 ARP110100834A ARP110100834A AR080756A1 AR 080756 A1 AR080756 A1 AR 080756A1 AR P110100834 A ARP110100834 A AR P110100834A AR P110100834 A ARP110100834 A AR P110100834A AR 080756 A1 AR080756 A1 AR 080756A1
- Authority
- AR
- Argentina
- Prior art keywords
- isobutanol
- stream
- butenes
- butene
- reactor
- Prior art date
Links
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 title abstract 12
- 230000018044 dehydration Effects 0.000 title abstract 4
- 238000006297 dehydration reaction Methods 0.000 title abstract 4
- 238000006317 isomerization reaction Methods 0.000 title abstract 4
- 239000003377 acid catalyst Substances 0.000 title 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002808 molecular sieve Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/82—Phosphates
- B01J29/84—Aluminophosphates containing other elements, e.g. metals, boron
- B01J29/85—Silicoaluminophosphates [SAPO compounds]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
- C07C11/09—Isobutene
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2518—Catalytic processes with crystalline alumino-silicates, e.g. molecular sieves
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
- C07C5/2775—Catalytic processes with crystalline alumino-silicates, e.g. molecular sieves
-
- 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
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
-
- 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
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (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
La presente solicitud (en una primera realizacion) se refiere a un procedimiento para la deshidratacion e isomerizacion esquelética simultáneas de isobutanol para preparar olefinas sustancialmente correspondientes, que tienen el mismo numero de carbonos y que consisten sustancialmente en una mezcla de n-butenos e iso-buteno, comprendiendo dicho procedimiento: a) introducir en un reactor una corriente (A) que comprende isobutanol, opcionalmente agua, opcionalmente un componente inerte, b) poner en contacto dicha corriente con un catalizador en dicho reactor, en condiciones eficaces para deshidratar e isomerizar esqueléticamente al menos una parte del isobutanol, para preparar una mezcla de n-butenos e iso-buteno, c) recuperar de dicho reactor una corriente (B), retirar el agua, el componente inerte si lo hubiera y el isobutanol no convertido si lo hubiera, para conseguir una mezcla de n-butenos e iso-buteno, en el que, la WHSV del isobutanol es al menos 1 h-1 o la temperatura es de 200sC a 600sC, y el catalizador es capaz de realizar simultáneamente la deshidratacion y la isomerizacion esquelética del buteno. El catalizador es un silicato cristalino del grupo de FER, MWW, EUO, MFS, ZSM-48, MTT, MFI, MEL o TON, que tiene un índice de Si/Al mayor de 10, o un silicato cristalino desaluminado del grupo de FER, MWW, EUO, MFS, ZSM-48, MTT, MFI, MEL o TON, que tiene un índice de Si/Al mayor de 10, o un silicato cristalino modificado con fosforo del grupo de FER, MWW, EUO, MFS, ZSM-48, MTT, MFI, MEL o TON, que tiene un índice de Si/Al mayor de 10, o un tamiz molecular de silicoaluminafosfato del grupo de AEL, o una alumina silicatada, zirconada, titanada o fluorada. Ventajosamente la corriente (B) se fracciona en una etapa d) para producir una corriente de n-butenos (N) y retirar la parte esencial de isobuteno opcionalmente reciclado con la corriente (A) al reactor de deshidratacion/isomerizacion de la etapa b).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10156537A EP2366682A1 (en) | 2010-03-15 | 2010-03-15 | Simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts |
| EP10159463A EP2374781A1 (en) | 2010-04-09 | 2010-04-09 | Simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts |
| EP10161125 | 2010-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR080756A1 true AR080756A1 (es) | 2012-05-09 |
Family
ID=44242479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110100834A AR080756A1 (es) | 2010-03-15 | 2011-03-15 | Deshidratacion e isomerizacion esqueletica simultaneas de isobutanol en catalizadores acidos |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9233886B2 (es) |
| EP (1) | EP2547638B1 (es) |
| JP (1) | JP5784646B2 (es) |
| KR (1) | KR101544257B1 (es) |
| CN (1) | CN102892729B (es) |
| AR (1) | AR080756A1 (es) |
| BR (1) | BR112012023262B1 (es) |
| CA (1) | CA2791218C (es) |
| CO (1) | CO6602154A2 (es) |
| DK (1) | DK2547638T3 (es) |
| EA (1) | EA025806B1 (es) |
| ES (1) | ES2603029T3 (es) |
| MY (1) | MY158968A (es) |
| PE (1) | PE20130759A1 (es) |
| PL (1) | PL2547638T3 (es) |
| WO (1) | WO2011113834A1 (es) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2583957A1 (de) * | 2011-10-18 | 2013-04-24 | LANXESS Deutschland GmbH | Lineare Butene aus Isobutanol |
| JP5797545B2 (ja) * | 2011-12-26 | 2015-10-21 | 旭化成ケミカルズ株式会社 | 触媒前駆体の熱処理方法、触媒の製造方法、並びにプロピレンの製造方法 |
| FR2988718B1 (fr) * | 2012-03-29 | 2014-04-11 | Ifp Energies Now | Procede de deshydratation et d'isomerisation d'alcools utilisant un solide de type aluminosilicate non zeolithique |
| US10464860B2 (en) | 2014-05-07 | 2019-11-05 | Mitsubishi Chemical Corporation | Method for producing isobutylene from isobutanol |
| EP2949635A1 (de) * | 2014-05-28 | 2015-12-02 | Linde Aktiengesellschaft | Verfahren zur Herstellung von Produktolefinen durch katalytische Dehydratisierung geeigneter Reaktanden |
| FR3026406B1 (fr) * | 2014-09-26 | 2016-12-09 | Ifp Energies Now | Procede de deshydratation isomerisante d'une charge alcool primaire substitue en position 2 par un groupement alkyl sur un catalyseur comprenant une zeolithe de type fer |
| US10512903B2 (en) | 2014-09-26 | 2019-12-24 | Total Research & Technology Feluy | Modified crystalline aluminosilicate for dehydration of alcohols |
| CN105585396B (zh) * | 2014-10-20 | 2018-03-20 | 中国石油化工股份有限公司 | 一种由含氧化合物制取低碳烯烃的方法 |
| KR101871641B1 (ko) | 2015-04-22 | 2018-06-26 | 미쯔비시 케미컬 주식회사 | 이소부틸렌 제조용 촉매 및 이소부틸렌의 제조 방법 |
| KR101966773B1 (ko) | 2015-05-13 | 2019-04-08 | 주식회사 엘지화학 | 이성질화 반응을 이용한 노말부텐의 분리방법 및 노말부텐을 분리하기 위한 공정시스템 |
| WO2017005719A1 (en) | 2015-07-09 | 2017-01-12 | Total Research & Technology Feluy | Modified crystalline aluminosilicate for dehydration of alcohols |
| EP3162763A1 (en) | 2015-10-30 | 2017-05-03 | Total Research & Technology Feluy SA | Simultaneous dehydration and skeletal isomerisation of isobutanol on ti-containing zeolite catalysts |
| WO2018047773A1 (ja) | 2016-09-06 | 2018-03-15 | 三菱ケミカル株式会社 | イソブチレンの分離精製方法およびイソブチレンの製造方法 |
| WO2018046515A1 (en) | 2016-09-09 | 2018-03-15 | Total Research & Technology Feluy | Process for dehydration of mono-alcohol(s) using a modified crystalline aluminosilicate |
| FR3056982A1 (fr) * | 2016-09-30 | 2018-04-06 | IFP Energies Nouvelles | Procede de production d'isoprene biosource mettant en œuvre une etape de deshydratation de butanols, une etape de metathese et une etape de deshydrogenation |
| MY190183A (en) * | 2016-10-06 | 2022-03-31 | Shell Int Research | Alkylaromatic conversion catalyst |
| FR3058414B1 (fr) | 2016-11-08 | 2019-08-16 | IFP Energies Nouvelles | Procede de deshydratation isomerisante d'un alcool primaire non lineaire sur un catalyseur comprenant une zeolithe de type fer et un liant aluminique |
| FR3058415B1 (fr) * | 2016-11-08 | 2018-12-07 | IFP Energies Nouvelles | Procede de deshydratation isomerisante d'une charge alcool primaire non lineaire en presence d'injection d'eau et d' un catalyseur comprenant une zeolithe de type fer ou mfs |
| FR3058413A1 (fr) | 2016-11-08 | 2018-05-11 | IFP Energies Nouvelles | Procede de deshydratation isomerisante d'une charge d'un monoalcool primaire non lineaire sur un catalyseur comprenant une zeolithe de type fer et un alcalin |
| CA2965062A1 (en) * | 2017-04-25 | 2018-10-25 | Nova Chemicals Corporation | Complex comprising odh unit with integrated oxygen separation module |
| CN107118069A (zh) * | 2017-06-17 | 2017-09-01 | 安徽海德石油化工有限公司 | 一种利用异丁醇脱水制备异丁烯的方法 |
| FR3068692B1 (fr) * | 2017-07-10 | 2019-08-16 | IFP Energies Nouvelles | Procede de deshydratation des alcools en olefines comprenant une etape de selectivation du catalyseur |
| EP3678774A4 (en) * | 2017-09-07 | 2021-05-05 | BASF Corporation | ZEOLITE WITH REDUCED EXTRA FRAME ALUMINUM |
| FR3074803B1 (fr) | 2017-12-13 | 2019-11-29 | IFP Energies Nouvelles | Procede d’elimination simultanee d’isobutanal et d’ethanol de charges olefiniques par adsorption sur un materiau a base d’oxyde refractaire poreux |
| FR3077818B1 (fr) | 2018-02-09 | 2020-02-28 | IFP Energies Nouvelles | Procede de separation d'olefines non lineaires d'une charge olefinique par distillation reactive |
| CN108218654A (zh) * | 2018-02-12 | 2018-06-29 | 安徽海德化工科技有限公司 | 一种利用异丁醇制备异辛烷的方法 |
| FR3080546B1 (fr) | 2018-04-25 | 2022-12-16 | Ifp Energies Now | Procede de deshydratation isomerisante de monoalcool primaire non lineaire sur un catalyseur zeolithique quadrilobe de type fer |
| BR112022004989A2 (pt) | 2019-09-30 | 2022-06-21 | Gevo Inc | Simultâneas desidratação, dimerização, e metátese de álcoois c2-c5 |
| CN113877624B (zh) * | 2020-07-03 | 2024-01-26 | 中国石油化工股份有限公司 | 一种碳四烯烃骨架正构化方法及其应用 |
| WO2022226371A2 (en) | 2021-04-23 | 2022-10-27 | Gevo, Inc. | Systems and processes for catalytic conversion of c1-c5 alcohols to c2-c5 olefin mixtures |
| FR3157389A1 (fr) | 2023-12-22 | 2025-06-27 | Axens | Procédé de production de bioalkylat ou d’essence biosourcée |
| WO2025202393A1 (en) | 2024-03-28 | 2025-10-02 | Basf Se | A process for preparing at least one alkene |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE890953C (de) * | 1938-08-21 | 1953-10-29 | Basf Ag | Verfahren zur Herstellung von Butylen-Isobutylen-Gemischen |
| ZA966107B (en) | 1995-07-21 | 1997-02-03 | Shell Int Research | Dehydration of primary alcohols. |
| US6768035B2 (en) * | 2002-01-31 | 2004-07-27 | Chevron U.S.A. Inc. | Manufacture of high octane alkylate |
| JP4431408B2 (ja) * | 2004-01-16 | 2010-03-17 | 新日本石油株式会社 | イソブテンの異性化によるｎ−ブテン類の製造方法 |
| US6977318B2 (en) * | 2004-05-04 | 2005-12-20 | Equistar Chemicals, Lp | Propylene production |
| DE102005062700A1 (de) * | 2005-12-28 | 2007-07-05 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Buten aus technischen Mischungen von C4-Kohlenwasserstoffen |
| US20080132741A1 (en) | 2006-06-16 | 2008-06-05 | D Amore Michael B | Process for making butenes from dry isobutanol |
| WO2008130995A2 (en) | 2007-04-18 | 2008-10-30 | E. I. Du Pont De Nemours And Company | Fermentive production of isobutanol using highly active ketol-acid reductoisomerase enzymes |
| CN101939277A (zh) * | 2008-02-07 | 2011-01-05 | 道达尔石油化学产品研究弗吕公司 | 醇在结晶硅酸盐上的脱水 |
| EP2090561A1 (en) | 2008-02-07 | 2009-08-19 | Total Petrochemicals Research Feluy | Dehydration of alcohols on crystalline silicates |
| US20110098518A1 (en) * | 2008-02-07 | 2011-04-28 | Delphine Minoux | Dehydration of Alcohols in the Presence of an Inert Component |
| EP2108634A1 (en) * | 2008-04-11 | 2009-10-14 | Total Petrochemicals Research Feluy | Dehydration of alcohols on crystalline silicates |
| US7982086B2 (en) * | 2009-02-03 | 2011-07-19 | Catalytic Distillation Technologies | Deisobutenizer |
-
2011
- 2011-03-15 AR ARP110100834A patent/AR080756A1/es not_active Application Discontinuation
- 2011-03-15 EP EP11708283.4A patent/EP2547638B1/en active Active
- 2011-03-15 DK DK11708283.4T patent/DK2547638T3/en active
- 2011-03-15 WO PCT/EP2011/053902 patent/WO2011113834A1/en not_active Ceased
- 2011-03-15 PE PE2012001548A patent/PE20130759A1/es not_active Application Discontinuation
- 2011-03-15 BR BR112012023262-2A patent/BR112012023262B1/pt not_active IP Right Cessation
- 2011-03-15 KR KR1020127024104A patent/KR101544257B1/ko not_active Expired - Fee Related
- 2011-03-15 MY MYPI2012003837A patent/MY158968A/en unknown
- 2011-03-15 JP JP2012557529A patent/JP5784646B2/ja not_active Expired - Fee Related
- 2011-03-15 CA CA2791218A patent/CA2791218C/en not_active Expired - Fee Related
- 2011-03-15 EA EA201270737A patent/EA025806B1/ru not_active IP Right Cessation
- 2011-03-15 PL PL11708283T patent/PL2547638T3/pl unknown
- 2011-03-15 ES ES11708283.4T patent/ES2603029T3/es active Active
- 2011-03-15 US US13/582,759 patent/US9233886B2/en not_active Expired - Fee Related
- 2011-03-15 CN CN201180024174.6A patent/CN102892729B/zh not_active Expired - Fee Related
-
2012
- 2012-09-14 CO CO12158684A patent/CO6602154A2/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| PL2547638T3 (pl) | 2017-02-28 |
| CN102892729A (zh) | 2013-01-23 |
| CA2791218A1 (en) | 2011-09-22 |
| DK2547638T3 (en) | 2016-12-12 |
| CA2791218C (en) | 2014-11-25 |
| JP2013522270A (ja) | 2013-06-13 |
| KR101544257B1 (ko) | 2015-08-12 |
| MY158968A (en) | 2016-11-30 |
| KR20120128685A (ko) | 2012-11-27 |
| EA201270737A1 (ru) | 2013-02-28 |
| EP2547638A1 (en) | 2013-01-23 |
| CO6602154A2 (es) | 2013-01-18 |
| PE20130759A1 (es) | 2013-06-21 |
| BR112012023262B1 (pt) | 2018-06-19 |
| WO2011113834A1 (en) | 2011-09-22 |
| CN102892729B (zh) | 2015-08-05 |
| US9233886B2 (en) | 2016-01-12 |
| ES2603029T3 (es) | 2017-02-23 |
| EA025806B1 (ru) | 2017-01-30 |
| US20130204057A1 (en) | 2013-08-08 |
| JP5784646B2 (ja) | 2015-09-24 |
| EP2547638B1 (en) | 2016-08-17 |
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