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WO2021153865A1 - Système de catalyseur à base de porphyrine, cathode utilisant un système de catalyseur pour batterie au lithium, et batterie au lithium comprenant une cathode pour batterie au lithium - Google Patents

Système de catalyseur à base de porphyrine, cathode utilisant un système de catalyseur pour batterie au lithium, et batterie au lithium comprenant une cathode pour batterie au lithium Download PDF

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Publication number
WO2021153865A1
WO2021153865A1 PCT/KR2020/009940 KR2020009940W WO2021153865A1 WO 2021153865 A1 WO2021153865 A1 WO 2021153865A1 KR 2020009940 W KR2020009940 W KR 2020009940W WO 2021153865 A1 WO2021153865 A1 WO 2021153865A1
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WIPO (PCT)
Prior art keywords
porphyrin
metal
lithium battery
catalyst
catalyst system
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Ceased
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PCT/KR2020/009940
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English (en)
Korean (ko)
Inventor
류원희
김현수
김보란
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Sookmyung Womens University SWU
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Sookmyung Womens University SWU
Priority date (The priority date 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 date listed.)
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Priority claimed from KR1020200009670A external-priority patent/KR102287467B1/ko
Priority claimed from KR1020200009671A external-priority patent/KR102287470B1/ko
Priority claimed from KR1020200009672A external-priority patent/KR102287471B1/ko
Application filed by Sookmyung Womens University SWU filed Critical Sookmyung Womens University SWU
Publication of WO2021153865A1 publication Critical patent/WO2021153865A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • B01J31/16—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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M12/00—Hybrid cells; Manufacture thereof
    • H01M12/08—Hybrid cells; Manufacture thereof composed of a half-cell of a fuel-cell type and a half-cell of the secondary-cell type
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
    • H01M4/90—Selection of catalytic material
    • 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
    • Y02E60/10—Energy storage using batteries

Definitions

  • the following description relates to a porphyrin-based catalyst system, a lithium battery positive electrode using the catalyst system, and a lithium battery including the lithium battery positive electrode.
  • lithium-air battery having a greater energy density than that of a lithium ion battery is attracting attention.
  • lithium-air batteries use oxygen in the atmosphere as an active material (active material: a material that chemically reacts to produce electrical energy when the battery is discharged), unlike lithium-ion batteries, so there is an advantage in terms of supply and demand of raw materials.
  • lithium-air batteries mainly use a positive electrode composed of porous carbon for smooth oxygen movement, and during discharge, lithium ions move from the negative electrode to the air electrode and oxygen reduction reaction (2Li + + O 2 +2e - ⁇ Li 2 O 2 , Oxygen reduction reaction, ORR) produces electricity, and the standard voltage at this time is thermodynamically reacted at 2.96V according to the Nernst formula. Conversely, if a voltage higher than the standard voltage is applied from the outside, the reverse reaction of oxygen evolution (Li 2 O 2 ⁇ 2Li + + O 2 +2e - , Oxygen Evolution Reaction, OER) takes place at the cathode and charging is performed.
  • oxygen evolution Li 2 O 2 ⁇ 2Li + + O 2 +2e - , Oxygen Evolution Reaction, OER
  • noble metal catalysts such as Au, Ag, Pt, Pd, Ru or Ir, MnO 2 , Mn 2 O 3 , Mn 3 O 4 , Co 3 O 4 , CuO, Fe 2 Transition metal oxide-based catalysts such as O 3 , NiO, CeO 2 , LaMnO 3 , MnCo 2 O 4 or Ba 0.5 Sr 0.5 Co 0.2 Fe 0.8 O 3 are combined with carbon materials and introduced into the cathode to improve battery efficiency has been going on a lot.
  • the problem of deactivation of the catalyst surface due to the lithium oxide or lithium carbonate-based surface product and the price increase of the transition metal oxide occurred.
  • Patent Document 0001 Republic of Korea Patent Publication No. 10-2017-0089122
  • a porphyrin-based catalyst system for a lithium battery is provided.
  • a positive electrode for a lithium battery to which the catalyst system is applied is provided.
  • It provides a lithium battery including the positive electrode for the lithium battery.
  • It provides a catalyst system comprising a porphyrin-based catalyst in which the central metal of porphyrin is substituted with a transition metal.
  • the transition metal is at least one of titanium (Ti), copper (Cu), iron (Fe), zinc (Zn), vanadium (V), manganese (Mn), nickel (Ni) and cobalt (Co) It may be characterized in that it contains a metal of.
  • the porphyrin-based catalyst may be characterized in that it is included in an electrolyte that transfers lithium ions generated in the negative electrode for a lithium battery to the positive electrode for a lithium battery.
  • the oxidation number of the ion of the central metal changes and the electron transfer reaction for the positive electrode for the lithium battery (electron transfer reaction) can be characterized by deriving.
  • the degree of promoting the charge reaction (Oxygen Evolution Reaction, OER) and the discharge reaction (Oxygen Reduction Reaction, ORR) according to the redox potential of the metal ion according to the type of the substituted metal as the central metal of the porphyrin may be characterized as being different.
  • the ion of the substituted metal as the central metal of the porphyrin binds and desorbs with oxygen as the active material of the positive electrode for a lithium battery in an oxygen atmosphere.
  • the ion of the substituted metal as the central metal of the porphyrin binds to and desorbs oxygen as an active material of the positive electrode for a lithium battery in an air atmosphere.
  • the performance of a lithium battery may be improved by utilizing porphyrin as a catalyst included in the electrolyte.
  • FIG. 1 is a view showing the operating principle of a porphyrin-based redox mediator (Redox Mediator, RM) as a catalyst for a lithium battery according to an embodiment of the present invention.
  • Redox Mediator RM
  • FIGS. 2 and 3 are graphs illustrating examples of CV (cyclic voltammetry) measurement results in an oxygen purge cell using a porphyrin catalyst including various metal ions, according to an embodiment of the present invention.
  • FIGS. 4 and 5 are graphs showing examples of charge/discharge curves in an oxygen purge cell using a porphyrin catalyst including various metal ions in an embodiment of the present invention.
  • 6 and 7 are graphs showing examples of CV measurement results in an air purge cell using a porphyrin catalyst including various metal ions in an embodiment of the present invention.
  • FIGS. 8 and 9 are graphs showing examples of charge/discharge curves in an air purge cell using a porphyrin catalyst including various metal ions in an embodiment of the present invention.
  • FIG. 10 is a graph showing an example of CV measurement results in an oxygen purge cell when nickel and vanadium are mixed according to an embodiment of the present invention.
  • FIG. 11 is a graph showing an example of CV measurement results in an oxygen purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • FIG. 12 is a graph illustrating an example of CV measurement results in an air purge cell when nickel and vanadium are mixed according to an embodiment of the present invention.
  • FIG. 13 is a graph illustrating an example of CV measurement results in an air purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • FIG. 14 is a graph illustrating an example of a charge/discharge curve in an oxygen purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • 15 is a graph illustrating an example of a charge/discharge curve in an air purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • FIG. 1 is a view showing the operating principle of a porphyrin-based redox mediator (Redox Mediator, RM) as a catalyst for a lithium battery according to an embodiment of the present invention.
  • Redox Mediator RM
  • Porphyrin is a rich raw material that is commonly found in natural chlorophyll or blood. When porphyrin is used as a raw material for a catalyst for lithium batteries, it has a very large price competitiveness.
  • hemoglobin Hb
  • Hb is a respiratory molecule found in the red blood cells of vertebrates, and functions to transport oxygen from the lungs to the body cells and carbon dioxide from the body cells to the lungs.
  • One hemoglobin molecule consists of four polypeptide chains, and each polypeptide chain contains one heme group consisting of a tetrapyridyl ring chelated to an Fe 2+ ion.
  • the iron atom of the hemoglobin molecule reversibly binds to a molecule of oxygen, which is then transported to somatic cells as the blood circulates. Then, the oxygen is released from the hemoglobin molecules in the tissue, and then the oxygen-free hemoglobin molecules absorb carbon dioxide, which returns to the lungs and then is released from the lungs. That is, hemoglobin serves to transport oxygen or carbon dioxide in a living body. Chlorophyll also binds and desorbs oxygen.
  • the porphyrin-based electrolyte catalyst has a complex function of actively repeating binding and desorption with oxygen molecules.
  • Scheme 1 below shows an electron transfer reaction by a conventional redox mediator
  • Scheme 2 below shows an electron transfer reaction by a porphyrin-based redox mediator that repeats active binding and desorption with oxygen molecules. An electron transfer reaction is shown.
  • M in Scheme 2 may mean a metal ion located at the center of the porphyrin structure.
  • the oxidation number changes (M 2+ ⁇ M 3+ + e - ), and the electrochemical redox driving voltage (Redox potential) may change depending on the type of metal ion.
  • OER Oxygen Evolution Reaction
  • ORR Oxygen Reduction Reaction
  • porphyrin-based redox mediator can tune the reaction voltage of the soluble catalyst by substituting the central metal (M), and various functional groups (eg, CO 2 H, SCH 3 , NO 2 ) , OH, NH 2 , SH) can be tuned to tune the type of substance group that reacts to the soluble catalyst.
  • M central metal
  • various functional groups eg, CO 2 H, SCH 3 , NO 2 ) , OH, NH 2 , SH
  • porphyrin as an electrolyte catalyst, the performance of a lithium battery such as a lithium oxygen battery or a lithium-air battery in an atmospheric atmosphere can be improved, and the redox characteristics of the electrolyte catalyst by substituting a central metal ion and Catalyst activity can be adjusted during charging and discharging.
  • porphyrin catalyst for charge reaction activity the porphyrin catalyst for discharge reaction activity
  • a porphyrin catalyst having bifunctionality during charge and discharge can be provided.
  • FIGS. 2 and 3 are graphs illustrating examples of CV (cyclic voltammetry) measurement results in an oxygen purge cell using a porphyrin catalyst including various metal ions, according to an embodiment of the present invention.
  • the graphs of FIGS. 2 and 3 show the case of using an electrolyte in which lithium bismide (LiTFSI) and tetraethylene glycol dimethyl ether (TEGDME) are mixed, and using various electrolyte catalysts under the condition that the scan rate is 5 mVs ⁇ 1 .
  • CV measurement results in an oxygen purge cell (O 2 Purged Cell) are shown.
  • various electrolyte catalysts as shown in FIGS.
  • a cell that does not introduce a porphyrin catalyst, a porphyrin (Ti-Porphyrin) in which a titanium ion is substituted with a central metal ion, and a copper ion is substituted with a central metal ion
  • a porphyrin (Cu-Porphyrin)
  • a porphyrin substituted with an iron ion for a central metal ion (Fe-Porphyrin)
  • a porphyrin substituted with a zinc ion for a central metal ion Zn-Porphyrin
  • a porphyrin substituted with a vanadium ion for a central metal ion V-Porphyrin
  • porphyrin substituted with manganese ion with a central metal ion (Mn-Porphyrin), porphyrin substituted with nickel ion with a central metal ion (Ni-Porphyrin), porphyrin substitute
  • the catalytic activity of the oxygen evolution reaction was high in the order of Zn-Porphyrin, Ni-Porphyrin, V-Porphyrin, Cu-Porphyrin, Fe-Porphyrin, and Co-Porphyrin.
  • the oxygen reduction reaction is in the order of Mn-Porphyrin, Fe-Porphyrin, Zn-Porphyrin, V-Porphyrin, Ni-Porphyrin, Cu-Porphyrin, Co-Porphyrin, and Ti-Porphyrin.
  • the catalytic activity was high.
  • the graphs of FIGS. 2 and 3 show that the catalytic activity in the oxygen purge cell of the porphyrins substituted with specific metal ions is higher than that of the cell (Pristine) or Cu-centered Chlorophyllin without the introduction of the porphyrin catalyst. indicates relatively high.
  • the porphyrin catalyst suitable for the charge reaction activity in the oxygen purge cell and the porphyrin catalyst suitable for the discharge reaction activity are different.
  • FIGS. 4 and 5 are graphs showing examples of charge/discharge curves in an oxygen purge cell using a porphyrin catalyst including various metal ions in an embodiment of the present invention.
  • the reaction start voltage of the discharge is about 2.87 V, which is higher than 2.5 V in the cell (pristine) without the introduction of the porphyrin catalyst, indicating that it is excellent in the discharge region (ORR region).
  • the discharge overpotential is greater than that of the cell without the porphyrin catalyst (Pristine) in the ORR region, and the other porphyrins have a significant difference from the cell without the porphyrin catalyst (Pristine).
  • FIGS. 6 and 7 are graphs showing examples of CV measurement results in an air purge cell using a porphyrin catalyst including various metal ions in an embodiment of the present invention.
  • the graphs of FIGS. 6 and 7 show the case of using an electrolyte in which lithium bismide (LiTFSI) and tetraethylene glycol dimethyl ether (TEGDME) are mixed, and using various electrolyte catalysts under the condition that the scan rate is 5 mVs ⁇ 1 .
  • CV measurement results in an air purged cell are shown. According to these measurement results, in the oxygen evolution reaction (OER), unlike in the oxygen purge cell described with reference to FIGS.
  • OER oxygen evolution reaction
  • the graphs of FIGS. 6 and 7 show the catalytic activity in the air purge cell of the porphyrins substituted with specific metal ions rather than the cells (Pristine) or Cu-centered chlorophyllin without the introduction of the porphyrin catalyst. This indicates that it is relatively high.
  • the porphyrin catalyst suitable for the charge reaction activity and the porphyrin catalyst suitable for the discharge reaction activity are different.
  • FIGS. 8 and 9 are graphs showing examples of charge/discharge curves in an air purge cell using a porphyrin catalyst including various metal ions in an embodiment of the present invention.
  • all types of porphyrins have a lower overvoltage than the cell (Pristine) without introducing the porphyrin catalyst in the charging region (OER region) (Mn-Porphyrin > Co-Porphyrin, Ni-Porphyrin, Fe-Porphyrin > Zn-Porphyrin, Ti-Porphyrin, V-Porphyrin > Cu-Porphyrin > Cu-centered chloropyllin).
  • the discharge region ORR region
  • most of the porphyrins are similar to the cell (Pristine) to which the porphyrin catalyst is not introduced.
  • the porphyrin catalyst suitable for the charge reaction activity and the porphyrin catalyst suitable for the discharge reaction activity are different in both the oxygen purge cell and the air purge cell.
  • the porphyrin catalyst for charge reaction activity and the porphyrin catalyst for discharge reaction activity are distinguished, and two different porphyrin catalysts are appropriately mixed to describe a porphyrin catalyst having bifunctionality during charge and discharge.
  • FIG. 10 is a graph showing an example of CV measurement results in an oxygen purge cell when nickel and vanadium are mixed according to an embodiment of the present invention.
  • a porphyrin catalyst using nickel (Ni) ions as a central metal ion and a porphyrin catalyst using vanadium (V) as a central metal ion are mixed (Ni + V blending) and added to the electrolyte in the oxygen purge cell.
  • CV measurement results are shown.
  • FIG. 11 is a graph showing an example of CV measurement results in an oxygen purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • a porphyrin catalyst using zinc (Zn) ions as a central metal ion and a porphyrin catalyst using manganese (Mn) as a central metal ion are mixed (Zn + Mn blending) in an oxygen purge cell added to the electrolyte.
  • CV measurement results are shown.
  • FIG. 11 is a graph showing an example of CV measurement results in an oxygen purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • Zn zinc
  • Mn manganese
  • Zn + Mn blending also shows a similar shape to that in the case of using only Mn-porphyrin rather than simultaneously having a catalytic effect when using each of Zn-porphyrin and Mn-porphyrin as a catalyst.
  • FIG. 12 is a graph illustrating an example of CV measurement results in an air purge cell when nickel and vanadium are mixed according to an embodiment of the present invention.
  • a porphyrin catalyst using nickel (Ni) ions as a central metal ion and a porphyrin catalyst using vanadium (V) as a central metal ion are mixed (Ni + V blending) in an air purge cell added to the electrolyte.
  • CV measurement results are shown.
  • the graph of FIG. 12 shows that when Ni + V blending is compared with each of Ni-porphyrin and V-porphyrin individually, the effect is reduced.
  • FIG. 13 is a graph illustrating an example of CV measurement results in an air purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • a porphyrin catalyst using zinc (Zn) ions as a central metal ion and a porphyrin catalyst using manganese (Mn) as a central metal ion are mixed (Zn + Mn blending) in an air purge cell added to the electrolyte.
  • CV measurement results are shown.
  • the graph of FIG. 13 shows that in the case of Zn + Mn blending, the catalytic effect of air Zn-porphyrin and Mn-porphyrin is simultaneously shown, and the catalytic effect is shown in both the ORR region and the OER region.
  • FIG. 14 is a graph illustrating an example of a charge/discharge curve in an oxygen purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • a porphyrin catalyst using zinc (Zn) ions as a central metal ion and a porphyrin catalyst using manganese (Mn) as a central metal ion are mixed (Zn + Mn blending) in the air purge cell added to the electrolyte.
  • Zn + Mn blending manganese
  • FIG. 15 is a graph illustrating an example of a charge/discharge curve in an air purge cell when zinc and manganese are mixed according to an embodiment of the present invention.
  • a porphyrin catalyst using zinc (Zn) ions as a central metal ion and a porphyrin catalyst using manganese (Mn) as a central metal ion are mixed (Zn + Mn blending) in the air purge cell added to the electrolyte.
  • Zn + Mn blending manganese
  • titanium (Ti), copper (Cu), iron (Fe), zinc (Zn), vanadium (V), manganese (Mn), nickel (Ni) and cobalt (Co) as the central metal ion of the porphyrin catalyst ) of at least one metal is described, but the metal ion that can be substituted at the center of the porphyrin catalyst can be extended to the ion of the transition metal.

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  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
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  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
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Abstract

L'invention concerne un système de catalyseur à base de porphyrine, une cathode utilisant le système de catalyseur pour une batterie au lithium, et une batterie au lithium comprenant la cathode pour une batterie au lithium. Un système de catalyseur à base de porphyrine selon un mode de réalisation peut comprendre un catalyseur à base de porphyrine dans lequel le noyau métallique de la porphyrine est substitué par un métal de transition.
PCT/KR2020/009940 2020-01-28 2020-07-28 Système de catalyseur à base de porphyrine, cathode utilisant un système de catalyseur pour batterie au lithium, et batterie au lithium comprenant une cathode pour batterie au lithium Ceased WO2021153865A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR10-2020-0009671 2020-01-28
KR1020200009670A KR102287467B1 (ko) 2020-01-28 2020-01-28 서로 다른 중심 금속의 포피린들에 기반한 촉매 시스템, 상기 촉매 시스템을 이용한 리튬 전지용 양극 및 상기 리튬 전지용 양극을 포함하는 리튬 전지
KR1020200009671A KR102287470B1 (ko) 2020-01-28 2020-01-28 포피린 기반의 촉매 시스템, 상기 촉매 시스템을 이용한 리튬 전지용 양극 및 상기 리튬 전지용 양극을 포함하는 리튬 전지
KR10-2020-0009672 2020-01-28
KR1020200009672A KR102287471B1 (ko) 2020-01-28 2020-01-28 포피린 기반의 촉매 시스템을 이용한 리튬 전지용 양극 및 상기 리튬 전지용 양극을 포함하는 리튬 전지
KR10-2020-0009670 2020-01-28

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115458816A (zh) * 2022-09-30 2022-12-09 储天新能源科技（长春）有限公司 一种有机电解液及锌离子电池和其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110306584A1 (en) * 2006-10-06 2011-12-15 Trustees Of Princeton Porphyrin Catalysts and Methods of Use Thereof
US20170067168A1 (en) * 2014-05-05 2017-03-09 Centre National De La Recherche Scientifique (Cnrs) Porphyrin molecular catalysts for selective electrochemical reduction of co2 into co
KR20170059301A (ko) * 2015-11-20 2017-05-30 현대자동차주식회사 리튬-공기 전지용 액상 촉매
KR20170068426A (ko) * 2017-06-09 2017-06-19 삼성전자주식회사 리튬 공기 전지
WO2018171251A1 (fr) * 2017-03-20 2018-09-27 江南大学 Catalyseur de métalloporphyrines à support solide et son application dans la préparation d'acide maléique

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110306584A1 (en) * 2006-10-06 2011-12-15 Trustees Of Princeton Porphyrin Catalysts and Methods of Use Thereof
US20170067168A1 (en) * 2014-05-05 2017-03-09 Centre National De La Recherche Scientifique (Cnrs) Porphyrin molecular catalysts for selective electrochemical reduction of co2 into co
KR20170059301A (ko) * 2015-11-20 2017-05-30 현대자동차주식회사 리튬-공기 전지용 액상 촉매
WO2018171251A1 (fr) * 2017-03-20 2018-09-27 江南大学 Catalyseur de métalloporphyrines à support solide et son application dans la préparation d'acide maléique
KR20170068426A (ko) * 2017-06-09 2017-06-19 삼성전자주식회사 리튬 공기 전지

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115458816A (zh) * 2022-09-30 2022-12-09 储天新能源科技（长春）有限公司 一种有机电解液及锌离子电池和其制备方法

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