CN112209830B - 醋酸乙烯酯的生产方法 - Google Patents
醋酸乙烯酯的生产方法 Download PDFInfo
- Publication number
- CN112209830B CN112209830B CN202011127390.0A CN202011127390A CN112209830B CN 112209830 B CN112209830 B CN 112209830B CN 202011127390 A CN202011127390 A CN 202011127390A CN 112209830 B CN112209830 B CN 112209830B
- Authority
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- China
- Prior art keywords
- tower
- ethyl acetate
- acetic acid
- vinyl acetate
- phase
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- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 title claims abstract description 181
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 419
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 385
- 239000007789 gas Substances 0.000 claims abstract description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 72
- 229910001868 water Inorganic materials 0.000 claims abstract description 72
- 238000000926 separation method Methods 0.000 claims abstract description 66
- 239000005977 Ethylene Substances 0.000 claims abstract description 54
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 51
- 238000000605 extraction Methods 0.000 claims abstract description 49
- 238000000895 extractive distillation Methods 0.000 claims abstract description 36
- 230000008569 process Effects 0.000 claims abstract description 33
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 24
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 23
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 23
- 239000001301 oxygen Substances 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 239000012535 impurity Substances 0.000 claims abstract description 15
- 238000010521 absorption reaction Methods 0.000 claims abstract description 12
- 238000007872 degassing Methods 0.000 claims abstract description 11
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 11
- 238000011084 recovery Methods 0.000 claims abstract description 11
- 230000018044 dehydration Effects 0.000 claims abstract description 10
- -1 Aldehyde ester Chemical class 0.000 claims abstract description 9
- 238000003795 desorption Methods 0.000 claims abstract description 9
- 238000007670 refining Methods 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 17
- 238000005191 phase separation Methods 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000005416 organic matter Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 description 74
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 22
- 239000007788 liquid Substances 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 238000009835 boiling Methods 0.000 description 15
- 239000012295 chemical reaction liquid Substances 0.000 description 14
- 239000003570 air Substances 0.000 description 13
- 239000001569 carbon dioxide Substances 0.000 description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000012495 reaction gas Substances 0.000 description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000004064 recycling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000005265 energy consumption Methods 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000005262 decarbonization Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- 230000001174 ascending effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000498 cooling water Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005261 decarburization Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- HDERJYVLTPVNRI-UHFFFAOYSA-N ethene;ethenyl acetate Chemical group C=C.CC(=O)OC=C HDERJYVLTPVNRI-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000013178 mathematical model Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/15—Vinyl acetate
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011127390.0A CN112209830B (zh) | 2020-10-20 | 2020-10-20 | 醋酸乙烯酯的生产方法 |
| JP2022576527A JP7486847B2 (ja) | 2020-10-20 | 2021-09-23 | エチレンアセタートの製造方法 |
| PCT/CN2021/119874 WO2022083396A1 (zh) | 2020-10-20 | 2021-09-23 | 醋酸乙烯酯的生产方法 |
| EP21881815.1A EP4144716B1 (en) | 2020-10-20 | 2021-09-23 | Method for producing vinyl acetate |
| US18/023,300 US11939286B2 (en) | 2020-10-20 | 2021-09-23 | Method for producing vinyl acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011127390.0A CN112209830B (zh) | 2020-10-20 | 2020-10-20 | 醋酸乙烯酯的生产方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112209830A CN112209830A (zh) | 2021-01-12 |
| CN112209830B true CN112209830B (zh) | 2021-08-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011127390.0A Active CN112209830B (zh) | 2020-10-20 | 2020-10-20 | 醋酸乙烯酯的生产方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11939286B2 (https=) |
| EP (1) | EP4144716B1 (https=) |
| JP (1) | JP7486847B2 (https=) |
| CN (1) | CN112209830B (https=) |
| WO (1) | WO2022083396A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112299989B (zh) * | 2020-10-20 | 2021-08-31 | 天津大学 | 醋酸乙烯生产工艺及装置 |
| CN112209830B (zh) * | 2020-10-20 | 2021-08-27 | 天津大学 | 醋酸乙烯酯的生产方法 |
| CN113861026B (zh) * | 2021-10-29 | 2022-09-06 | 天津大学 | 一种乙炔法合成的醋酸乙烯及醋酸的精制方法 |
| CN117959746A (zh) * | 2022-10-25 | 2024-05-03 | 中国石油化工股份有限公司 | 一种醋酸乙烯制备过程中脱除醋酸乙酯的系统及方法 |
| CN115745794B (zh) * | 2022-11-16 | 2023-06-20 | 天津大学 | 乙烯法醋酸乙烯生产工艺及装置 |
| CN116651016B (zh) * | 2023-06-13 | 2025-11-21 | 山东中盛药化设备有限公司 | 一种用于聚醚醚酮的分离提纯系统及工艺 |
| CN116924877A (zh) * | 2023-07-26 | 2023-10-24 | 天津大学 | 醋酸乙烯合成过程循环气精制工艺及装置 |
| CN119751195B (zh) * | 2025-03-10 | 2025-07-01 | 华东理工大学 | 一种含密封油的乙烯气体中的乙烯的回收方法和回收装置 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1248855A (en) * | 1968-10-25 | 1971-10-06 | Du Pont | Purification of vinyl acetate |
| CN1769259A (zh) * | 2004-11-04 | 2006-05-10 | 塞拉尼斯化学品欧洲有限公司 | 制备醋酸乙烯酯的方法 |
| WO2008019873A1 (en) * | 2006-08-17 | 2008-02-21 | Celanese Chemicals Europe Gmbh | Process for working up vinyl acetate |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3905875A (en) * | 1968-05-10 | 1975-09-16 | Bayer Ag | Process for the purification of crude liquid vinyl acetate |
| GB1305367A (https=) * | 1970-07-01 | 1973-01-31 | ||
| US4897161A (en) * | 1989-03-20 | 1990-01-30 | Lloyd Berg | Separation of vinyl acetate from ethyl acetate by extractive distillation |
| DE19825254C1 (de) * | 1998-06-05 | 1999-11-11 | Celanese Gmbh | Verfahren zur Aufarbeitung von rohem, flüssigem Vinylacetat |
| CN104718182B (zh) * | 2012-08-30 | 2016-08-31 | 国际人造丝公司 | 具有用于预脱水塔的侧线式反应器的乙酸乙烯酯制造方法 |
| CN102936198B (zh) * | 2012-10-12 | 2016-05-25 | 天津大学 | 生产醋酸乙烯的方法 |
| CN112209830B (zh) * | 2020-10-20 | 2021-08-27 | 天津大学 | 醋酸乙烯酯的生产方法 |
-
2020
- 2020-10-20 CN CN202011127390.0A patent/CN112209830B/zh active Active
-
2021
- 2021-09-23 WO PCT/CN2021/119874 patent/WO2022083396A1/zh not_active Ceased
- 2021-09-23 EP EP21881815.1A patent/EP4144716B1/en active Active
- 2021-09-23 JP JP2022576527A patent/JP7486847B2/ja active Active
- 2021-09-23 US US18/023,300 patent/US11939286B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1248855A (en) * | 1968-10-25 | 1971-10-06 | Du Pont | Purification of vinyl acetate |
| CN1769259A (zh) * | 2004-11-04 | 2006-05-10 | 塞拉尼斯化学品欧洲有限公司 | 制备醋酸乙烯酯的方法 |
| WO2008019873A1 (en) * | 2006-08-17 | 2008-02-21 | Celanese Chemicals Europe Gmbh | Process for working up vinyl acetate |
Non-Patent Citations (1)
| Title |
|---|
| 醋酸乙烯精馏装置的工艺流程模拟与优化;罗静;《中国优秀硕士学位论文工程科技Ⅰ辑》;20180815;全文 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US11939286B2 (en) | 2024-03-26 |
| JP7486847B2 (ja) | 2024-05-20 |
| JP2023531171A (ja) | 2023-07-21 |
| US20230312452A1 (en) | 2023-10-05 |
| EP4144716C0 (en) | 2025-05-14 |
| CN112209830A (zh) | 2021-01-12 |
| EP4144716A1 (en) | 2023-03-08 |
| WO2022083396A1 (zh) | 2022-04-28 |
| EP4144716B1 (en) | 2025-05-14 |
| EP4144716A4 (en) | 2024-06-19 |
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