MX365001B - Catalizador de hidrogenacion y deshidrogenacion, y metodos para hacerlo y usarlo. - Google Patents

Catalizador de hidrogenacion y deshidrogenacion, y metodos para hacerlo y usarlo.

Info

Publication number
MX365001B
MX365001B MX2014001887A MX2014001887A MX365001B MX 365001 B MX365001 B MX 365001B MX 2014001887 A MX2014001887 A MX 2014001887A MX 2014001887 A MX2014001887 A MX 2014001887A MX 365001 B MX365001 B MX 365001B
Authority
MX
Mexico
Prior art keywords
catalysts
hydrogenation
dehydrogenation
catalyze
present application
Prior art date
Application number
MX2014001887A
Other languages
English (en)
Other versions
MX2014001887A (es
Inventor
Goussev Dmitri
Spasyuk Denis
Original Assignee
Goussev Dmitri
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.)
Filing date
Publication date
Application filed by Goussev Dmitri filed Critical Goussev Dmitri
Publication of MX2014001887A publication Critical patent/MX2014001887A/es
Publication of MX365001B publication Critical patent/MX365001B/es

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Classifications

    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
    • B01J31/2471—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom
    • 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
    • B01J31/20—Carbonyls
    • 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
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
    • C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B31/00—Reduction in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/002—Osmium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C07F15/0053—Ruthenium compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
    • 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
    • B01J2231/76—Dehydrogenation
    • B01J2231/763—Dehydrogenation of -CH-XH (X= O, NH/N, S) to -C=X or -CX triple bond species
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0202—Polynuclearity
    • B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • 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
    • B01J2531/821—Ruthenium
    • 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
    • B01J2531/825—Osmium
    • 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
    • B01J31/189—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 containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Combustion & Propulsion (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Hydrogen, Water And Hydrids (AREA)
  • Pyridine Compounds (AREA)

Abstract

La presente solicitud describe complejos útiles como catalizadores para la síntesis química orgánica que incluye la hidrogenación y deshidrogenación de compuestos insaturados o deshidrogenación de sustratos. La gama de compuestos de sustrato de hidrogenación incluye ésteres, lactonas, aceites y grasas, que dan por resultados alcoholes, dioles y trioles como productos de reacción. Los catalizadores de la solicitud actual se pueden utilizar para catalizar una reacción de hidrogenación bajo condiciones sin solvente. Los presentes catalizadores también permiten que la hidrogenación proceda sin base adicionada, y se pueden utilizar en lugar de los métodos de reducción convencionales que emplean hidruros de elementos del grupo principal. Además, los catalizadores de la presente solicitud pueden catalizar una reacción de deshidrogenación bajo condiciones homogéneas y/o sin aceptor. Como tales, los catalizadores proporcionados en la presente pueden ser útiles en reducir sustancialmente el costo y mejorar el perfil ambiental de los procesos de fabricación para una variedad de sustancias químicas.
MX2014001887A 2011-08-18 2012-08-20 Catalizador de hidrogenacion y deshidrogenacion, y metodos para hacerlo y usarlo. MX365001B (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161524815P 2011-08-18 2011-08-18
US201261593840P 2012-02-01 2012-02-01
PCT/CA2012/050571 WO2013023307A1 (en) 2011-08-18 2012-08-20 Hydrogenation and dehydrogenation catalyst, and methods of making and using the same

Publications (2)

Publication Number Publication Date
MX2014001887A MX2014001887A (es) 2014-05-27
MX365001B true MX365001B (es) 2019-05-17

Family

ID=47714662

Family Applications (1)

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MX2014001887A MX365001B (es) 2011-08-18 2012-08-20 Catalizador de hidrogenacion y deshidrogenacion, y metodos para hacerlo y usarlo.

Country Status (10)

Country Link
US (2) US10583427B2 (es)
EP (1) EP2744815B1 (es)
JP (3) JP2014524428A (es)
CN (2) CN103857687B (es)
BR (1) BR112014006964B1 (es)
CA (1) CA2845017C (es)
ES (1) ES2719798T3 (es)
MX (1) MX365001B (es)
SG (1) SG11201400146RA (es)
WO (1) WO2013023307A1 (es)

Families Citing this family (16)

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Publication number Priority date Publication date Assignee Title
GB201208589D0 (en) 2012-05-16 2012-06-27 Givaudan Sa Improvements in or relating to organic compounds
WO2014139030A1 (en) * 2013-03-15 2014-09-18 Goussev Dmitri Complex catalysts based on amino-phosphine ligands for hydrogenation and dehydrogenation processes
CN105308058B (zh) * 2013-06-20 2018-10-12 株式会社可乐丽 包含三齿氨基二碳烯配体的金属配合物和使用其的氢化还原方法
GB201401230D0 (en) 2014-01-24 2014-03-12 Givaudan Sa Improvements in or relating to organic compounds
CN104804041B (zh) * 2014-01-26 2018-07-13 中国科学院上海有机化学研究所 Ncp配体、其铱络合物、合成方法、中间体及应用
EP3233800A4 (en) * 2014-12-19 2018-08-01 Dow Silicones Corporation Ligand components, associated reaction products, activated reaction products, hydrosilylation catalysts and hydrosilylation curable compositions including the ligand components, and associated methods for preparing same
EP3310745B1 (en) * 2015-06-17 2022-08-10 Firmenich SA Hydrogenation of aldehyde or ketone compounds with fe/tridentate ligands complexes
CN104926602A (zh) * 2015-07-09 2015-09-23 武汉工程大学 一种癸酮催化氢化制备癸醇的方法
CN106050480B (zh) * 2016-07-06 2018-09-14 浙江大学 适用于氢能汽车的液体有机氢化物车载供氢系统
WO2019138000A1 (en) 2018-01-10 2019-07-18 Basf Se Use of a ruthenium catalyst comprising a tetradentate ligand for hydrogenation of esters and/or formation of esters and a ruthenium complex comprising said tetradentate ligand
WO2019175158A1 (en) 2018-03-16 2019-09-19 Firmenich Sa Hydrogenation of carbonyls with tetradentate pnnp ligand ruthenium complexes
CN111153940B (zh) * 2018-11-08 2022-06-21 中国科学院上海有机化学研究所 Pnn三齿配体、钌络合物、其制备方法和应用
IL264043A (en) * 2018-12-31 2020-06-30 Yeda Res & Dev A reversible liquid organic system for storing and releasing hydrogen, based on ethylene glycol
CN109705169B (zh) * 2019-01-30 2021-05-18 苏州大学 双茂基稀土金属配合物在催化胺硼烷脱氢偶联中的应用
CN114080379B (zh) * 2019-07-03 2024-02-23 巴斯夫欧洲公司 在Ru-PNN配合物存在下将酯类氢化为醇类
CN112570032A (zh) * 2020-11-17 2021-03-30 广东仁康达材料科技有限公司 一种水溶性氢甲酰化催化剂及其应用

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JP5388570B2 (ja) 2005-04-05 2014-01-15 フイルメニツヒ ソシエテ アノニム Ｒｕ／四座配位子錯体を用いたエステルの水素化
SG163603A1 (en) 2005-07-21 2010-08-30 Chevron Phillips Chemical Co Diimine metal complexes, methods of synthesis, and methods of using in oligomerization and polymerization
JP5294303B2 (ja) 2008-03-31 2013-09-18 国立大学法人神戸大学 新規なｎ，ｎ，ｐ−三座シッフ塩基配位子化合物および該化合物を用いた不斉合成

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Publication number Publication date
US10583427B2 (en) 2020-03-10
JP6616757B2 (ja) 2019-12-04
JP2017078058A (ja) 2017-04-27
CN110105399B (zh) 2022-08-05
CA2845017C (en) 2020-09-08
EP2744815B1 (en) 2019-01-16
BR112014006964B1 (pt) 2020-11-17
CN103857687B (zh) 2020-10-16
WO2013023307A1 (en) 2013-02-21
BR112014006964A2 (pt) 2017-06-13
ES2719798T3 (es) 2019-07-16
CN103857687A (zh) 2014-06-11
EP2744815A1 (en) 2014-06-25
MX2014001887A (es) 2014-05-27
JP2014524428A (ja) 2014-09-22
SG11201400146RA (en) 2014-04-28
US20200147597A1 (en) 2020-05-14
EP2744815A4 (en) 2015-04-01
CA2845017A1 (en) 2013-02-21
CN110105399A (zh) 2019-08-09
US20140328748A1 (en) 2014-11-06
US11305268B2 (en) 2022-04-19
JP2020002142A (ja) 2020-01-09

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