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WO2003010136A1 - Complexes organometalliques, catalyseurs les contenant et procede de preparation d'esters carboxyliques - Google Patents

Complexes organometalliques, catalyseurs les contenant et procede de preparation d'esters carboxyliques Download PDF

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Publication number
WO2003010136A1
WO2003010136A1 PCT/JP2002/007051 JP0207051W WO03010136A1 WO 2003010136 A1 WO2003010136 A1 WO 2003010136A1 JP 0207051 W JP0207051 W JP 0207051W WO 03010136 A1 WO03010136 A1 WO 03010136A1
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WO
WIPO (PCT)
Prior art keywords
same
carboxylic esters
organometallic complexes
alkyl
preparation
Prior art date
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Ceased
Application number
PCT/JP2002/007051
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English (en)
Japanese (ja)
Inventor
Yasushi Kuroda
Tetsuo Nakajo
Keiji Maruoka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Resonac Holdings Corp
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Showa Denko KK
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Publication date
Application filed by Showa Denko KK filed Critical Showa Denko KK
Publication of WO2003010136A1 publication Critical patent/WO2003010136A1/fr
Anticipated expiration legal-status Critical
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06Aluminium compounds
    • C07F5/069Aluminium compounds without C-aluminium linkages
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2243At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2252Sulfonate ligands
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2252Sulfonate ligands
    • B01J31/2256Sulfonate ligands being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional ligands
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/226Sulfur, e.g. thiocarbamates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/09Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/44Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/003Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/20Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/26Zinc
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/31Aluminium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/32Gallium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/33Indium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/42Tin
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/48Zirconium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne des complexes organométalliques représentés par la formule générale (1), pouvant être utilisés avec avantage dans les systèmes de synthèse d'esters carboxyliques à partir d'aldéhydes, par exemple, la réaction de Tischenko. Dans cette formule, M représente un atome de métal, R représente un groupe C1-8 alkyle éventuellement ramifié ou un groupe aromatique ou aralkyle éventuellement substitué, L représente un groupe organique, contenant un ou plusieurs cycles aromatiques, pouvant former un cycle composé de cinq à sept éléments, X, Y et M compris, et X et Y représentent chacun, de façon indépendante, -O-, un groupe -NR1-, -N(SO2R2)-, ou analogue (sous réserve des cas dans lesquels X et Y sont identiques), R1 représentant éventuellement un groupe C¿1-8? alkyle éventuellement ramifié qui peut être halogéné et R?2¿ représentant un groupe C¿1-10? alkyle éventuellement ramifié pouvant être halogéné.
PCT/JP2002/007051 2001-07-25 2002-07-11 Complexes organometalliques, catalyseurs les contenant et procede de preparation d'esters carboxyliques Ceased WO2003010136A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2001223862 2001-07-25
JP2001-223862 2001-07-25
JP2001-292276 2001-09-25
JP2001292276A JP2003104953A (ja) 2001-07-25 2001-09-25 有機金属錯体化合物および該化合物を用いたカルボン酸エステル製造方法

Publications (1)

Publication Number Publication Date
WO2003010136A1 true WO2003010136A1 (fr) 2003-02-06

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PCT/JP2002/007051 Ceased WO2003010136A1 (fr) 2001-07-25 2002-07-11 Complexes organometalliques, catalyseurs les contenant et procede de preparation d'esters carboxyliques

Country Status (3)

Country Link
JP (1) JP2003104953A (fr)
CN (1) CN1464875A (fr)
WO (1) WO2003010136A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004047990A1 (fr) * 2002-11-27 2004-06-10 Showa Denko K. K. Catalyseur destines a la preparation d'esters carboxyliques et processus de preparation d'esters carboxyliques avec ce catalyseur
CN109331875A (zh) * 2018-11-14 2019-02-15 山西大学 一种双核镁金属催化剂及其制备方法和应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116874411B (zh) * 2023-07-13 2024-04-16 西安欧得光电材料有限公司 一种1-溴咔唑的合成方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920444A (en) * 1970-12-21 1975-11-18 Minnesota Mining & Mfg Method comprising the use of N-substituted perfluoroalkyanesulfonamides as herbicidal and plant growth modifying agents, and composition
JPS55108430A (en) * 1979-02-13 1980-08-20 Japan Synthetic Rubber Co Ltd Rubber composition
JPH05230133A (ja) * 1992-02-19 1993-09-07 Mitsui Toatsu Chem Inc オレフィンの重合触媒及びそれを用いたポリオレフィンの製造方法
JPH05295023A (ja) * 1992-04-24 1993-11-09 Mitsui Toatsu Chem Inc オレフィンの重合用固体触媒及びそれを用いたポリオレフィンの製造方法
DE4238233A1 (de) * 1992-11-12 1994-05-19 Fahlberg List Pharma Gmbh N-Sulfonyl-aminophenole, ihre Verwendung als pharmazeutische Wirkstoffe und sie enthaltende Arzneimittel
US5591848A (en) * 1994-10-07 1997-01-07 The Penn State Research Foundation Spiroconjugated charge-transfer dyes for optical applications
WO1998012190A2 (fr) * 1996-09-11 1998-03-26 Krenitsky Pharmaceutical, Inc. Composes constituant pharmacologiquement des principes actifs et leur utilisation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920444A (en) * 1970-12-21 1975-11-18 Minnesota Mining & Mfg Method comprising the use of N-substituted perfluoroalkyanesulfonamides as herbicidal and plant growth modifying agents, and composition
JPS55108430A (en) * 1979-02-13 1980-08-20 Japan Synthetic Rubber Co Ltd Rubber composition
JPH05230133A (ja) * 1992-02-19 1993-09-07 Mitsui Toatsu Chem Inc オレフィンの重合触媒及びそれを用いたポリオレフィンの製造方法
JPH05295023A (ja) * 1992-04-24 1993-11-09 Mitsui Toatsu Chem Inc オレフィンの重合用固体触媒及びそれを用いたポリオレフィンの製造方法
DE4238233A1 (de) * 1992-11-12 1994-05-19 Fahlberg List Pharma Gmbh N-Sulfonyl-aminophenole, ihre Verwendung als pharmazeutische Wirkstoffe und sie enthaltende Arzneimittel
US5591848A (en) * 1994-10-07 1997-01-07 The Penn State Research Foundation Spiroconjugated charge-transfer dyes for optical applications
WO1998012190A2 (fr) * 1996-09-11 1998-03-26 Krenitsky Pharmaceutical, Inc. Composes constituant pharmacologiquement des principes actifs et leur utilisation

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Title
ANCHISI CARLO ET AL.: "Studies on the synthesis of heterocyclic compounds", J. HETEROCYCL. CHEM., vol. 13, no. 5, 1976, pages 1033 - 1036, XP002957699 *
ANDRAE K. ET AL.: "1,2-Phenyleneoxothio 3d-element compounds", Z. ANORG. ALLG. CHEM., vol. 498, 1983, pages 199 - 204, XP002957698 *
HANSON G. ET AL.: "Convenient routes of 4,4''-functionalized o-terphenyls and 2,2''-functionalized biphenyls", J. ORG.CHEM., vol. 46, no. 26, 1981, pages 5441 - 5443, XP002959801 *
STEGMANN HARTMUT B. ET AL.: "Transformation of 2,2-diphenyl-2-fluor-2,3-dihydro-1,3,2-benzoxazaphospholen", PHOSPHORUS SULFUR, vol. 8, no. 1, 1980, pages 59 - 66, XP002959802 *
TSUTOMU ISHIKAWA ET AL.: "Anomalous substituent effects in the bischler-napieralski reaction of 2-aryl aromatic formamides", JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 26, 2000, pages 9143 - 9151, XP002957700 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004047990A1 (fr) * 2002-11-27 2004-06-10 Showa Denko K. K. Catalyseur destines a la preparation d'esters carboxyliques et processus de preparation d'esters carboxyliques avec ce catalyseur
CN109331875A (zh) * 2018-11-14 2019-02-15 山西大学 一种双核镁金属催化剂及其制备方法和应用

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Publication number Publication date
CN1464875A (zh) 2003-12-31
JP2003104953A (ja) 2003-04-09

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