BR112017022224A2 - processos integrados para produzir, e processo para preparar uma composição - Google Patents
processos integrados para produzir, e processo para preparar uma composiçãoInfo
- Publication number
- BR112017022224A2 BR112017022224A2 BR112017022224A BR112017022224A BR112017022224A2 BR 112017022224 A2 BR112017022224 A2 BR 112017022224A2 BR 112017022224 A BR112017022224 A BR 112017022224A BR 112017022224 A BR112017022224 A BR 112017022224A BR 112017022224 A2 BR112017022224 A2 BR 112017022224A2
- Authority
- BR
- Brazil
- Prior art keywords
- solvent
- derivative
- feed
- oxidation
- preparing
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 abstract 5
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 3
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
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- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/066—Zirconium or hafnium; Oxides or hydroxides 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- 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
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/656—Manganese, technetium or rhenium
- B01J23/6562—Manganese
-
- 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
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- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B33/00—Oxidation in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/80—Solid-state polycondensation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino-carboxylic acids or of polyamines and polycarboxylic acids
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- 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
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
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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
- 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)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
trata-se de um processo integrado para a produção de ácido 2,5-furanodicarboxílico e/ou um derivado do mesmo a partir de uma alimentação que contém açúcar de seis carbonos que compreende: a) desidratar uma alimentação que compreende uma unidade de açúcar de seis carbonos, na presença de uma fonte de bromo e de um solvente, para gerar uma alimentação de oxidação que compreende pelo menos um dentre 5-hidroximetilfurfural e/ou um derivado ou derivados de 5-hidroximetilfurfural no solvente, juntamente com pelo menos uma espécie que contém bromo; b) colocar a alimentação de oxidação proveniente da etapa (a) em contato com um catalisador de metal e com uma fonte de oxigênio sob condições de oxidação para produzir uma mistura de produto de oxidação que compreende ácido 2,5-furanodicarboxílico (fdca) e/ou um derivado do mesmo, o solvente e um catalisador residual; c) purificar e separar a mistura obtida na etapa (b) para obter fdca e/ou um derivado do mesmo e o solvente; e d) reciclar pelo menos uma porção do solvente obtido na etapa (c) para a etapa (a).
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562147280P | 2015-04-14 | 2015-04-14 | |
US62/147,280 | 2015-04-14 | ||
US201562201295P | 2015-08-05 | 2015-08-05 | |
US62/201,295 | 2015-08-05 | ||
PCT/US2016/027191 WO2016168233A1 (en) | 2015-04-14 | 2016-04-13 | Processes for producing 2,5-furandicarboxylic acid and derivatives thereof and polymers made therefrom |
Publications (2)
Publication Number | Publication Date |
---|---|
BR112017022224A2 true BR112017022224A2 (pt) | 2018-07-03 |
BR112017022224B1 BR112017022224B1 (pt) | 2022-05-03 |
Family
ID=57127308
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR112017022224-8A BR112017022224B1 (pt) | 2015-04-14 | 2016-04-13 | Processo integrado para produzir ácido 2,5-furanodicarboxílico e/ou um derivado do mesmo |
Country Status (11)
Country | Link |
---|---|
US (3) | US10538499B2 (pt) |
EP (3) | EP4306568A3 (pt) |
CN (2) | CN114262312B (pt) |
BR (1) | BR112017022224B1 (pt) |
DK (1) | DK3283470T3 (pt) |
ES (1) | ES2965441T3 (pt) |
FI (1) | FI3283470T3 (pt) |
HU (1) | HUE065368T2 (pt) |
PL (1) | PL3283470T3 (pt) |
WO (1) | WO2016168233A1 (pt) |
ZA (1) | ZA201707639B (pt) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUE065368T2 (hu) | 2015-04-14 | 2024-05-28 | Du Pont | Eljárás 2,5-furándikabonsav és származékai elõállítására |
CA3010631A1 (en) | 2016-01-13 | 2017-07-20 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
BR112020000611B1 (pt) | 2017-07-12 | 2024-03-05 | Stora Enso Oyj | Produtos purificados de via de ácido 2,5-furanoodicarboxílico |
WO2019014393A1 (en) * | 2017-07-12 | 2019-01-17 | Stora Enso Oyj | NOVEL PROCESSES FOR PREPARING 2,5-FURANDICARBOXYLIC ACID |
EP3498699A1 (en) | 2017-12-13 | 2019-06-19 | Basf Se | Chromatography method for the purification of furfural derivatives |
CN108531434B (zh) * | 2018-04-04 | 2020-12-29 | 江南大学 | 一种提高拉乌尔菌2,5-呋喃二甲酸产量的方法 |
EP3774754A4 (en) * | 2018-04-13 | 2021-04-28 | Archer Daniels Midland Company | DEHYDRATION AND CYCLIZATION OF ALPHA, BETA-DIHYDROXYCARBONYL COMPOUNDS TO 2-SUBSTITUTE FURAN DERIVATIVES |
DE102018208507A1 (de) * | 2018-05-29 | 2019-12-05 | Südzucker AG | Anolytfraktion-katalysierte HMF-Herstellung |
KR102176738B1 (ko) * | 2018-07-09 | 2020-11-09 | 한국생산기술연구원 | 퓨란-2,5-디알킬카르복실레이트의 제조방법 |
KR20210152497A (ko) * | 2019-04-15 | 2021-12-15 | 스토라 엔소 오와이제이 | 용매의 회수 및 휴민 물질 및 그의 조성물의 단리를 위한 방법 |
CN111072601B (zh) * | 2020-01-04 | 2023-02-03 | 烟台大学 | 一种5-羟甲基糠醛制备2,5-呋喃二甲醛的方法 |
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BR112022024693A2 (pt) * | 2020-06-04 | 2023-02-28 | Archer Daniels Midland Co | Processo para a determinação de aldeídos solúveis em uma composição, e processo para o monitoramento de aldeídos solúveis em uma composição |
CN113372302A (zh) * | 2020-09-04 | 2021-09-10 | 浙江糖能科技有限公司 | 2,5-四氢呋喃二甲醇二酸酯及其制备方法、应用 |
WO2022081495A1 (en) * | 2020-10-13 | 2022-04-21 | Archer Daniels Midland Company | Oxidative pretreatment of carbohydrate dehydration products comprising humins |
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CN113121477A (zh) * | 2021-06-02 | 2021-07-16 | 宁波国生科技有限公司 | 一种2,5-四氢呋喃二甲酸的制备方法 |
CN115028608B (zh) * | 2022-05-07 | 2024-05-10 | 浙江恒逸石化研究院有限公司 | 一种5-羟甲基糠醛、5-烷酰氧基甲基糠醛和2,5-呋喃二甲酸的联产方法 |
CN115141167B (zh) * | 2022-07-25 | 2023-07-04 | 合肥利夫生物科技有限公司 | 一种无金属催化果糖一锅法制备呋喃二甲酸的方法 |
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2016
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- 2016-04-13 CN CN202111508913.0A patent/CN114262312B/zh active Active
- 2016-04-13 US US15/564,590 patent/US10538499B2/en active Active
- 2016-04-13 CN CN201680022208.0A patent/CN107848995B/zh active Active
- 2016-04-13 DK DK16780582.9T patent/DK3283470T3/da active
- 2016-04-13 ES ES16780582T patent/ES2965441T3/es active Active
- 2016-04-13 EP EP23209530.7A patent/EP4306568A3/en active Pending
- 2016-04-13 PL PL16780582.9T patent/PL3283470T3/pl unknown
- 2016-04-13 WO PCT/US2016/027191 patent/WO2016168233A1/en unknown
- 2016-04-13 EP EP16780582.9A patent/EP3283470B1/en active Active
- 2016-04-13 EP EP23209651.1A patent/EP4306569A3/en active Pending
- 2016-04-13 FI FIEP16780582.9T patent/FI3283470T3/fi active
- 2016-04-13 BR BR112017022224-8A patent/BR112017022224B1/pt active IP Right Grant
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US20200339527A1 (en) | 2020-10-29 |
EP4306569A3 (en) | 2024-04-10 |
EP4306568A3 (en) | 2024-04-10 |
HUE065368T2 (hu) | 2024-05-28 |
ES2965441T3 (es) | 2024-04-15 |
CN107848995A (zh) | 2018-03-27 |
CN114262312A (zh) | 2022-04-01 |
CN107848995B (zh) | 2021-12-28 |
FI3283470T3 (fi) | 2023-12-13 |
EP4306569A2 (en) | 2024-01-17 |
US11028063B2 (en) | 2021-06-08 |
CN114262312B (zh) | 2024-08-20 |
DK3283470T3 (da) | 2023-12-11 |
EP4306568A2 (en) | 2024-01-17 |
US10745369B2 (en) | 2020-08-18 |
WO2016168233A1 (en) | 2016-10-20 |
US20180093961A1 (en) | 2018-04-05 |
EP3283470B1 (en) | 2023-11-15 |
US20200095218A1 (en) | 2020-03-26 |
US10538499B2 (en) | 2020-01-21 |
EP3283470A1 (en) | 2018-02-21 |
PL3283470T3 (pl) | 2024-05-06 |
EP3283470A4 (en) | 2018-11-21 |
ZA201707639B (en) | 2019-04-24 |
BR112017022224B1 (pt) | 2022-05-03 |
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