DK3242964T3 - Elektrokemisk og fotoelektrokemisk oxidering af 5-hydroxymethylfurfural til 2,5-furandicarboxylsyre og 2,5-diformylfuran - Google Patents
Elektrokemisk og fotoelektrokemisk oxidering af 5-hydroxymethylfurfural til 2,5-furandicarboxylsyre og 2,5-diformylfuran Download PDFInfo
- Publication number
- DK3242964T3 DK3242964T3 DK16735346.5T DK16735346T DK3242964T3 DK 3242964 T3 DK3242964 T3 DK 3242964T3 DK 16735346 T DK16735346 T DK 16735346T DK 3242964 T3 DK3242964 T3 DK 3242964T3
- Authority
- DK
- Denmark
- Prior art keywords
- diformylfuran
- hydroxymethylfurfural
- electrochemical
- furandicarboxylic acid
- photoelectrochemical oxidation
- Prior art date
Links
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 title 2
- PXJJKVNIMAZHCB-UHFFFAOYSA-N 2,5-diformylfuran Chemical compound O=CC1=CC=C(C=O)O1 PXJJKVNIMAZHCB-UHFFFAOYSA-N 0.000 title 1
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title 1
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title 1
- 230000003647 oxidation Effects 0.000 title 1
- 238000007254 oxidation reaction Methods 0.000 title 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/042—Electrodes formed of a single material
- C25B11/043—Carbon, e.g. diamond or graphene
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
- C25B11/052—Electrodes comprising one or more electrocatalytic coatings on a substrate
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
- C25B11/073—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
- C25B11/073—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material
- C25B11/075—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material consisting of a single catalytic element or catalytic compound
- C25B11/081—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material consisting of a single catalytic element or catalytic compound the element being a noble metal
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/051—Electrodes formed of electrocatalysts on a substrate or carrier
- C25B11/073—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material
- C25B11/075—Electrodes formed of electrocatalysts on a substrate or carrier characterised by the electrocatalyst material consisting of a single catalytic element or catalytic compound
- C25B11/087—Photocatalytic compound
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/07—Oxygen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/21—Photoelectrolysis
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
- C25B9/17—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
- C25B9/50—Cells or assemblies of cells comprising photoelectrodes; Assemblies of constructional parts thereof
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
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- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/36—Hydrogen production from non-carbon containing sources, e.g. by water electrolysis
-
- 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
- Y02P20/133—Renewable energy sources, e.g. sunlight
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Hybrid Cells (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/592,031 US9598780B2 (en) | 2015-01-08 | 2015-01-08 | Electrochemical and photoelectrochemical oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and 2,5-diformylfuran |
| PCT/US2016/012312 WO2016112091A1 (en) | 2015-01-08 | 2016-01-06 | Electrochemical and photoelectrochemical oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and 2,5-diformylfuran |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3242964T3 true DK3242964T3 (da) | 2022-02-07 |
Family
ID=56356381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK16735346.5T DK3242964T3 (da) | 2015-01-08 | 2016-01-06 | Elektrokemisk og fotoelektrokemisk oxidering af 5-hydroxymethylfurfural til 2,5-furandicarboxylsyre og 2,5-diformylfuran |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US9598780B2 (da) |
| EP (1) | EP3242964B1 (da) |
| BR (1) | BR112017014218B1 (da) |
| CA (1) | CA2971615C (da) |
| DK (1) | DK3242964T3 (da) |
| WO (1) | WO2016112091A1 (da) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9885119B2 (en) | 2015-02-12 | 2018-02-06 | Wisconsin Alumni Research Foundation | Electrochemical and photoelectrochemical reduction of furfurals |
| EP3297995B1 (en) * | 2015-05-21 | 2019-07-10 | Avantium Knowledge Centre B.V. | Process for the preparation of an aromatic dicarboxylic acid |
| EP3297996B1 (en) | 2015-05-21 | 2019-07-10 | Avantium Knowledge Centre B.V. | Process for the purification of a carboxylic acid-containing composition |
| US10392715B2 (en) | 2016-08-29 | 2019-08-27 | Wisconsin Alumni Research Foundation | Electrochemical reductive amination of furfural-based molecules |
| US11060197B2 (en) * | 2016-11-24 | 2021-07-13 | Avantium Knowledge Centre B.V. | Process for treating a dicarboxylic acid composition |
| US10669639B2 (en) | 2017-09-05 | 2020-06-02 | Wisconsin Alumni Research Foundation | Eletrochemical oxidation of 5-hydroxymethylfurfural using copper-based anodes |
| US11142833B2 (en) | 2017-10-09 | 2021-10-12 | Wisconsin Alumni Research Foundation | Electrochemical oxidation of aromatic aldehydes in acidic media |
| DE102017123797A1 (de) * | 2017-10-12 | 2019-04-18 | Synphabase Ag | Furandicarbonsäure |
| CN108130554A (zh) * | 2017-10-31 | 2018-06-08 | 天津工业大学 | 一种次氯酸钠电催化5-hmf制备fdca的方法 |
| CN108531936B (zh) * | 2018-04-29 | 2019-11-05 | 浙江工业大学 | 一种生物质类化合物电催化氧化制取2,5-呋喃二甲酸的方法 |
| DE102018208507A1 (de) | 2018-05-29 | 2019-12-05 | Südzucker AG | Anolytfraktion-katalysierte HMF-Herstellung |
| CN110106514B (zh) * | 2019-05-13 | 2020-09-29 | 浙江大学 | 一种5-羟甲基糠醛电化学氧化制备2,5-呋喃二甲酸的方法 |
| CN112921341B (zh) * | 2021-01-25 | 2022-06-21 | 北京化工大学 | 高效小分子催化氧化与产氢耦合的反应系统 |
| CN113755863B (zh) * | 2021-09-13 | 2022-05-06 | 中山大学 | 一种非贵金属催化剂同步电化学还原胺化和氧化醛基制备高值品的方法 |
| CN113861142B (zh) * | 2021-10-14 | 2023-04-07 | 新乡学院 | 一种2,5-呋喃二甲酸及其制备方法 |
| FR3129955B1 (fr) | 2021-12-03 | 2023-11-17 | Ifp Energies Now | Procédé d’électro-oxydation d’un composé furanique |
| CN114438525B (zh) * | 2022-01-24 | 2023-08-15 | 吉林大学 | 一种糠醛阴极电化学转化合成糠酸的方法 |
| CN114481170B (zh) * | 2022-01-24 | 2023-08-15 | 吉林大学 | 一种由糠醛线性成对电化学合成糠酸的方法 |
| CN114592204B (zh) * | 2022-03-08 | 2023-06-13 | 郑州大学 | 一种用于糠醛和5-羟甲基糠醛电氧化的装置及方法 |
| CN114574881B (zh) * | 2022-03-09 | 2024-04-09 | 厦门大学 | 一种电催化氧化醛醇类物质制备多元羧酸的方法 |
| CN114737215B (zh) * | 2022-03-31 | 2023-11-14 | 福建工程学院 | 一种镍钨复合电极的制备方法及其在电催化氧化中的应用 |
| CN116590724A (zh) * | 2022-12-09 | 2023-08-15 | 浙江工业大学台州研究院 | 一种锰掺杂硫化镍电催化剂在工业级电流密度下制取2,5-呋喃二甲酸的方法 |
| WO2024241311A1 (en) * | 2023-05-24 | 2024-11-28 | Technion Research & Development Foundation Limited | Photo-bio-electrochemical cell |
| CN119800383A (zh) * | 2024-12-31 | 2025-04-11 | 万华化学集团股份有限公司 | 一种成对电解法同时合成异辛醛和异辛酸的方法 |
| CN119985789B (zh) * | 2025-03-07 | 2025-09-19 | 中国科学院宁波材料技术与工程研究所 | 一种同时测定5-羟甲基糠醛及其氧化产物的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL161831B2 (pl) * | 1990-02-06 | 1993-08-31 | Univ Lodzki | Sposób otrzymywania kwasu 2,5-furanodikarboksytowego PL |
| JPH04362199A (ja) | 1991-06-06 | 1992-12-15 | Nec Corp | 電気めっき装置 |
| US7052587B2 (en) | 2003-06-27 | 2006-05-30 | General Motors Corporation | Photoelectrochemical device and electrode |
| AU2008323618B2 (en) * | 2007-11-16 | 2012-01-19 | 579453 Ontario Inc. | Photo electrodes |
| EP3666764A1 (en) | 2009-10-07 | 2020-06-17 | Furanix Technologies B.V | Method for the preparation of 2,5-furandicarboxylic acid and for the preparation of the dialkyl ester of 2,5-furandicarboxylic acid |
| IT1401911B1 (it) * | 2010-08-06 | 2013-08-28 | Novamont Spa | Processo per la sintesi di acido 2,5-furandicarbossilico |
| WO2013049711A1 (en) * | 2011-09-29 | 2013-04-04 | Bio Architecture Lab, Inc. | Methods for preparing 2,5-furandicarboxylic acid |
| WO2013082110A1 (en) * | 2011-12-02 | 2013-06-06 | Bio2Electric, Llc | Reactor, process, and system for the oxidation of gaseous streams |
| US11566332B2 (en) * | 2012-03-06 | 2023-01-31 | Board Of Trustees Of Michigan State University | Electrocatalytic hydrogenation and hydrodeoxygenation of oxygenated and unsaturated organic compounds |
| US8969534B2 (en) | 2013-02-20 | 2015-03-03 | Wisconsin Alumni Research Foundataion | Selective aerobic alcohol oxidation method for conversion of lignin into simple aromatic compounds |
| US9435043B2 (en) * | 2014-04-14 | 2016-09-06 | California Institute Of Technology | Oxygen evolution reaction catalysis |
| US9856567B2 (en) | 2014-06-16 | 2018-01-02 | Wisconsin Alumni Research Foundation | Synthesis of high-surface-area nanoporous BiVO4 electrodes |
| US10633749B2 (en) * | 2014-07-23 | 2020-04-28 | Board Of Trustees Of Michigan State University | Electrolyzer reactor and related methods |
| WO2016057894A1 (en) | 2014-10-10 | 2016-04-14 | The Penn State Research Foundation | Ammonia-based thermoelectrochemical systems and methods |
| EP3297995B1 (en) | 2015-05-21 | 2019-07-10 | Avantium Knowledge Centre B.V. | Process for the preparation of an aromatic dicarboxylic acid |
| US20180023199A1 (en) | 2016-07-19 | 2018-01-25 | Utah State University | Electrocatalytic hydrogen evolution and biomass upgrading |
| EP3366681A1 (en) | 2017-02-28 | 2018-08-29 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Production of 2,5-furandicarboxylic acid |
| US10669639B2 (en) | 2017-09-05 | 2020-06-02 | Wisconsin Alumni Research Foundation | Eletrochemical oxidation of 5-hydroxymethylfurfural using copper-based anodes |
-
2015
- 2015-01-08 US US14/592,031 patent/US9598780B2/en active Active
-
2016
- 2016-01-06 EP EP16735346.5A patent/EP3242964B1/en active Active
- 2016-01-06 WO PCT/US2016/012312 patent/WO2016112091A1/en not_active Ceased
- 2016-01-06 CA CA2971615A patent/CA2971615C/en active Active
- 2016-01-06 DK DK16735346.5T patent/DK3242964T3/da active
- 2016-01-06 BR BR112017014218-0A patent/BR112017014218B1/pt active IP Right Grant
-
2017
- 2017-02-01 US US15/421,750 patent/US10655233B2/en active Active
-
2020
- 2020-04-09 US US16/844,437 patent/US11136679B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CA2971615A1 (en) | 2016-07-14 |
| BR112017014218A2 (pt) | 2018-03-06 |
| US11136679B2 (en) | 2021-10-05 |
| EP3242964A1 (en) | 2017-11-15 |
| BR112017014218B1 (pt) | 2022-07-12 |
| US20200255960A1 (en) | 2020-08-13 |
| US20170145572A1 (en) | 2017-05-25 |
| US10655233B2 (en) | 2020-05-19 |
| US20160201204A1 (en) | 2016-07-14 |
| EP3242964B1 (en) | 2021-11-03 |
| EP3242964A4 (en) | 2018-11-14 |
| WO2016112091A1 (en) | 2016-07-14 |
| US9598780B2 (en) | 2017-03-21 |
| CA2971615C (en) | 2022-11-29 |
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