JP7128622B2 - ヒドロホルミル化プロセス - Google Patents
ヒドロホルミル化プロセス Download PDFInfo
- Publication number
- JP7128622B2 JP7128622B2 JP2017529301A JP2017529301A JP7128622B2 JP 7128622 B2 JP7128622 B2 JP 7128622B2 JP 2017529301 A JP2017529301 A JP 2017529301A JP 2017529301 A JP2017529301 A JP 2017529301A JP 7128622 B2 JP7128622 B2 JP 7128622B2
- Authority
- JP
- Japan
- Prior art keywords
- vaporizer
- stream
- catalyst
- kpa
- psia
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00033—Continuous processes
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462087572P | 2014-12-04 | 2014-12-04 | |
| US62/087,572 | 2014-12-04 | ||
| PCT/US2015/061332 WO2016089602A1 (en) | 2014-12-04 | 2015-11-18 | Hydroformylation process |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020160278A Division JP2021008477A (ja) | 2014-12-04 | 2020-09-25 | ヒドロホルミル化プロセス |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017537918A JP2017537918A (ja) | 2017-12-21 |
| JP2017537918A5 JP2017537918A5 (enExample) | 2020-02-20 |
| JP7128622B2 true JP7128622B2 (ja) | 2022-08-31 |
Family
ID=54705909
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017529301A Active JP7128622B2 (ja) | 2014-12-04 | 2015-11-18 | ヒドロホルミル化プロセス |
| JP2020160278A Pending JP2021008477A (ja) | 2014-12-04 | 2020-09-25 | ヒドロホルミル化プロセス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020160278A Pending JP2021008477A (ja) | 2014-12-04 | 2020-09-25 | ヒドロホルミル化プロセス |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10023516B2 (enExample) |
| EP (1) | EP3230248B1 (enExample) |
| JP (2) | JP7128622B2 (enExample) |
| KR (1) | KR102507703B1 (enExample) |
| CN (1) | CN107001218B (enExample) |
| BR (1) | BR112017011447B1 (enExample) |
| CA (1) | CA2969527C (enExample) |
| MX (1) | MX381950B (enExample) |
| MY (1) | MY184826A (enExample) |
| PL (1) | PL3230248T3 (enExample) |
| RU (1) | RU2699368C2 (enExample) |
| TW (1) | TWI586644B (enExample) |
| WO (1) | WO2016089602A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3374340T3 (pl) | 2015-11-10 | 2022-04-11 | Dow Technology Investments Llc | Sposób wytwarzania aldehydów |
| RU2751511C9 (ru) | 2016-02-11 | 2021-08-18 | Дау Текнолоджи Инвестментс Ллк | Способы превращения олефинов в спирты, простые эфиры или их комбинации |
| CN107469860B (zh) * | 2017-08-22 | 2020-05-19 | 中国海洋石油集团有限公司 | 一种提高铑/双亚膦酸酯催化剂稳定性的方法 |
| TWI793216B (zh) | 2017-12-07 | 2023-02-21 | 美商陶氏科技投資公司 | 氫甲醯化方法 |
| MY203235A (en) * | 2018-11-29 | 2024-06-19 | Dow Technology Investments Llc | Hydroformylation process |
| GB201907659D0 (en) | 2019-05-30 | 2019-07-17 | Johnson Matthey Davy Technologies Ltd | Process |
| WO2021247177A1 (en) | 2020-06-05 | 2021-12-09 | SCION Holdings LLC | Alcohols production |
| EP4161696A4 (en) * | 2020-06-05 | 2025-05-28 | Scion Holdings LLC | BRANCHED ALCOHOLS |
| WO2021247516A1 (en) | 2020-06-05 | 2021-12-09 | SCION Holdings LLC | Branched alcohols |
| US12221404B2 (en) | 2020-06-05 | 2025-02-11 | SCION Holdings LLC | Composition comprising branched aldehydes |
| ES2974422T3 (es) * | 2020-07-30 | 2024-06-27 | Evonik Oxeno Gmbh & Co Kg | Procedimiento para la preparación de aldehídos y separación del sistema catalítico mediante separación por membrana |
| GB202012930D0 (en) * | 2020-08-19 | 2020-09-30 | Johnson Matthey Davy Technologies Ltd | Process for hydroformylation with removal of dissolved hydrogen |
| CN116261565A (zh) | 2020-10-13 | 2023-06-13 | 美国陶氏有机硅公司 | 具有醛官能团的有机硅化合物的制备 |
| CN112403401B (zh) * | 2020-11-06 | 2022-06-21 | 中国海洋石油集团有限公司 | 一种烯烃氢甲酰化制醛中醛和催化剂分离的装置和方法 |
| WO2022132372A1 (en) * | 2020-12-14 | 2022-06-23 | Dow Technology Investments Llc | Processes to improve catalytic metal accountability in hydroformylation processes |
| US12145904B2 (en) | 2020-12-17 | 2024-11-19 | SCION Holdings LLC | Branched products |
| CN118019747A (zh) | 2021-10-06 | 2024-05-10 | 陶氏环球技术有限责任公司 | 丙基亚胺官能化有机硅化合物和伯氨基丙基官能化有机硅化合物的制备 |
| KR20240074844A (ko) | 2021-10-06 | 2024-05-28 | 다우 글로벌 테크놀로지스 엘엘씨 | 프로필이민-작용성 유기규소 화합물 및 1차 아미노프로필-작용성 유기규소 화합물의 제조 |
| JP2024536162A (ja) | 2021-10-06 | 2024-10-04 | ダウ グローバル テクノロジーズ エルエルシー | イミン官能性有機ケイ素化合物及び一級アミノ官能性有機ケイ素化合物の調製 |
| WO2023086718A1 (en) | 2021-11-11 | 2023-05-19 | Dow Technology Investments Llc | Processes for recovering rhodium from hydroformylation processes |
| EP4437031A2 (en) | 2021-11-22 | 2024-10-02 | Dow Global Technologies LLC | Preparation of organosilicon compounds with carbinol functionality |
| CN118338965A (zh) | 2021-12-16 | 2024-07-12 | 陶氏技术投资有限责任公司 | 包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法 |
| EP4448170B1 (en) | 2021-12-16 | 2025-08-20 | Dow Technology Investments LLC | Compounds, transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes |
| EP4496833A1 (en) | 2022-03-21 | 2025-01-29 | Dow Global Technologies LLC | Preparation of organosilicon compounds with carboxy functionality |
| EP4508106A1 (en) | 2022-04-13 | 2025-02-19 | Dow Global Technologies LLC | Silicone - vinylester functional compounds and methods for their preparation and use in personal care compositions |
| KR20250003565A (ko) | 2022-04-13 | 2025-01-07 | 다우 실리콘즈 코포레이션 | 조성물, 우레탄 프리폴리머, 및 관련 방법 및 용도 |
| US20250145647A1 (en) | 2022-04-13 | 2025-05-08 | Dow Silicones Corporation | Preparation of organosilicon compounds with vinylester functionality |
| CN118843652A (zh) | 2022-04-13 | 2024-10-25 | 陶氏环球技术有限责任公司 | 制备聚醚官能有机硅化合物 |
| CN114773172B (zh) * | 2022-06-20 | 2022-10-18 | 中海油天津化工研究设计院有限公司 | 一种烯烃氢甲酰化制醛工艺优化方法 |
| GB202213997D0 (en) | 2022-09-26 | 2022-11-09 | Johnson Matthey Davy Technologies Ltd | Parallel zone hydroformylation reaction |
| WO2024123510A1 (en) | 2022-12-06 | 2024-06-13 | Dow Technology Investments Llc | Process of controlling heavies in a recycle catalyst stream |
| GB202303617D0 (en) | 2023-03-13 | 2023-04-26 | Johnson Matthey Davy Technologies Ltd | Method and apparatus for producing aldehyde |
| WO2025029369A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Process for improving rhodium/phosphite- based homogenous hydroformylation catalyst activity |
| WO2025029349A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Hydroformylation process |
| WO2025038266A1 (en) | 2023-08-14 | 2025-02-20 | Dow Global Technologies Llc | Cobalt catalyzed hydroformylation of vinyl-functional polyorganosiloxanes |
| WO2025170897A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Optimized gas-stripping hydroformylation process for oxo aldehydes |
| WO2025170887A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Gas distribution in gas-stripping hydroformylation reactor for oxo aldehydes |
| WO2025170886A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Purge for a gas-stripping hydroformylation reactor for oxo aldehydes |
| WO2025170891A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Composition of matter for gas-stripping oxo aldehydes hydroformylation process |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002161063A (ja) | 2000-09-29 | 2002-06-04 | Oxeno Olefinchemie Gmbh | オレフィンのヒドロホルミル化のためのロジウム触媒の安定化 |
| JP2011527287A (ja) | 2008-07-03 | 2011-10-27 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 循環触媒流中の重質物の制御プロセス |
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| US3415906A (en) | 1964-05-29 | 1968-12-10 | Hooker Chemical Corp | Phosphite phospholane and phosphorinane compounds |
| US3527809A (en) | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
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| DE2646792C2 (de) | 1975-10-23 | 1985-05-09 | Mitsubishi Petrochemical Co., Ltd., Tokio/Tokyo | Verfahren zur Herstellung einer α-(arylsubstituierten)-Propionsäure und/oder eines Esters derselben |
| US4247486A (en) | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
| US4518809A (en) | 1981-06-11 | 1985-05-21 | Monsanto Company | Preparation of pentyl nonanols |
| US4528403A (en) | 1982-10-21 | 1985-07-09 | Mitsubishi Chemical Industries Ltd. | Hydroformylation process for preparation of aldehydes and alcohols |
| GB8334359D0 (en) | 1983-12-23 | 1984-02-01 | Davy Mckee Ltd | Process |
| US4599206A (en) | 1984-02-17 | 1986-07-08 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| ZA851189B (en) * | 1984-02-17 | 1985-09-25 | Union Carbide Corp | Transition metal complex catalyzed reactions |
| US5110990A (en) | 1984-03-30 | 1992-05-05 | Union Carbide Chemicals & Plastics Technology Corporation | Process for recovery of phosphorus ligand from vaporized aldehyde |
| US4567302A (en) | 1984-07-20 | 1986-01-28 | Angus Chemical | Polymeric quaternary ammonium salts possessing antimicrobial activity and methods for preparation and use thereof |
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| US4835299A (en) | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
| US5113022A (en) | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
| US5001274A (en) | 1989-06-23 | 1991-03-19 | Union Carbide Chemicals And Plastics Company Inc. | Hydroformylation process |
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| DE4026406A1 (de) | 1990-08-21 | 1992-02-27 | Basf Ag | Rhodiumhydroformylierungskatalysatoren mit bis-phosphit-liganden |
| US5179055A (en) | 1990-09-24 | 1993-01-12 | New York University | Cationic rhodium bis(dioxaphosphorus heterocycle) complexes and their use in the branched product regioselective hydroformylation of olefins |
| US5102505A (en) | 1990-11-09 | 1992-04-07 | Union Carbide Chemicals & Plastics Technology Corporation | Mixed aldehyde product separation by distillation |
| TW213465B (enExample) | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
| US5360938A (en) | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
| DE4204808A1 (de) | 1992-02-18 | 1993-08-19 | Basf Ag | Verfahren zur herstellung von (omega)-formylalkancarbonsaeureestern |
| US5312996A (en) | 1992-06-29 | 1994-05-17 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process for producing 1,6-hexanedials |
| US5364950A (en) | 1992-09-29 | 1994-11-15 | Union Carbide Chimicals & Plastics Technology Corporation | Process for stabilizing phosphite ligands in hydroformylation reaction mixtures |
| FR2700535B1 (fr) | 1993-01-19 | 1995-04-14 | Hoechst France | Procédé continu de fabrication industrielle du diméthoxyéthanal. |
| US5426238A (en) | 1993-06-10 | 1995-06-20 | Mitsubishi Kasei Corporation | Method for producing an aldehyde |
| BE1008017A3 (nl) | 1994-01-06 | 1995-12-12 | Dsm Nv | Werkwijze voor de bereiding van 5-formylvaleriaanzure ester. |
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| US5648553A (en) | 1994-12-09 | 1997-07-15 | Mitsubishi Chemical Corporation | Method for producing aldehydes |
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| US5731472A (en) | 1995-12-06 | 1998-03-24 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
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| JP3812095B2 (ja) | 1997-10-28 | 2006-08-23 | 三菱化学株式会社 | アルデヒド類の製造方法及びこれに用いるビスホスファイト |
| DE19913352A1 (de) | 1999-03-24 | 2000-09-28 | Basf Ag | Katalysator, umfassend einen Komplex eines Metalls der VIII. Nebengruppe auf Basis eines Phospinamiditliganden |
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| CA2575122C (en) | 2004-08-02 | 2013-06-25 | Union Carbide Chemicals & Plastics Technology Corporation | Stabilization of a hydroformylation process |
| MY146608A (en) | 2007-03-20 | 2012-09-14 | Dow Technology Investments Llc | Hydroformylation process with improved control over product isomers |
| KR101060375B1 (ko) | 2007-05-29 | 2011-08-29 | 주식회사 엘지화학 | 하이드로포르밀화 방법 및 장치 |
| KR101310552B1 (ko) | 2010-04-20 | 2013-09-23 | 주식회사 엘지화학 | 올레핀의 하이드로포르밀화에 의한 알데히드 제조 방법 |
| EP2491062B1 (en) | 2010-05-17 | 2013-12-11 | Dow Global Technologies LLC | Process for selectively polymerizing ethylene and catalyst therefor |
| CN102826972B (zh) | 2011-06-17 | 2015-05-13 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化反应制备醛的方法 |
| US9422383B2 (en) | 2011-12-20 | 2016-08-23 | Dow Global Technologies Llc | Ethylene/alpha-olefin/nonconjugated polyene interpolymers and processes to form the same |
| DE102012223572A1 (de) | 2012-12-18 | 2014-06-18 | Evonik Industries Ag | Steuerung der Viskosität von Reaktionslösungen in Hydroformylierungverfahren |
-
2015
- 2015-11-08 MY MYPI2017000834A patent/MY184826A/en unknown
- 2015-11-18 CN CN201580064234.5A patent/CN107001218B/zh active Active
- 2015-11-18 US US15/522,137 patent/US10023516B2/en active Active
- 2015-11-18 PL PL15801645T patent/PL3230248T3/pl unknown
- 2015-11-18 RU RU2017121307A patent/RU2699368C2/ru active
- 2015-11-18 KR KR1020177016356A patent/KR102507703B1/ko active Active
- 2015-11-18 CA CA2969527A patent/CA2969527C/en active Active
- 2015-11-18 JP JP2017529301A patent/JP7128622B2/ja active Active
- 2015-11-18 WO PCT/US2015/061332 patent/WO2016089602A1/en not_active Ceased
- 2015-11-18 EP EP15801645.1A patent/EP3230248B1/en active Active
- 2015-11-18 MX MX2017006792A patent/MX381950B/es unknown
- 2015-11-18 BR BR112017011447-0A patent/BR112017011447B1/pt active IP Right Grant
- 2015-11-25 TW TW104139257A patent/TWI586644B/zh active
-
2020
- 2020-09-25 JP JP2020160278A patent/JP2021008477A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002161063A (ja) | 2000-09-29 | 2002-06-04 | Oxeno Olefinchemie Gmbh | オレフィンのヒドロホルミル化のためのロジウム触媒の安定化 |
| JP2011527287A (ja) | 2008-07-03 | 2011-10-27 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 循環触媒流中の重質物の制御プロセス |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3230248B1 (en) | 2019-12-25 |
| JP2017537918A (ja) | 2017-12-21 |
| TW201620863A (zh) | 2016-06-16 |
| RU2017121307A3 (enExample) | 2019-02-01 |
| CN107001218A (zh) | 2017-08-01 |
| JP2021008477A (ja) | 2021-01-28 |
| BR112017011447B1 (pt) | 2020-12-15 |
| MX2017006792A (es) | 2017-09-08 |
| PL3230248T3 (pl) | 2020-05-18 |
| WO2016089602A1 (en) | 2016-06-09 |
| RU2017121307A (ru) | 2018-12-19 |
| CA2969527A1 (en) | 2016-06-09 |
| MX381950B (es) | 2025-03-13 |
| US20170355656A1 (en) | 2017-12-14 |
| KR102507703B1 (ko) | 2023-03-09 |
| CA2969527C (en) | 2023-08-22 |
| RU2699368C2 (ru) | 2019-09-05 |
| MY184826A (en) | 2021-04-24 |
| US10023516B2 (en) | 2018-07-17 |
| BR112017011447A2 (pt) | 2018-02-27 |
| KR20170093152A (ko) | 2017-08-14 |
| EP3230248A1 (en) | 2017-10-18 |
| TWI586644B (zh) | 2017-06-11 |
| CN107001218B (zh) | 2021-02-26 |
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