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WO2003010136A1 - Organometallic complexes, catalysts containing the same, and process for preparation of carboxylic esters - Google Patents

Organometallic complexes, catalysts containing the same, and process for preparation of carboxylic esters 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
Authority
WO
WIPO (PCT)
Prior art keywords
same
carboxylic esters
organometallic complexes
alkyl
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2002/007051
Other languages
French (fr)
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
Original Assignee
Showa Denko KK
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 Showa Denko KK filed Critical Showa Denko KK
Publication of WO2003010136A1 publication Critical patent/WO2003010136A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C07F5/069—Aluminium compounds without C-aluminium linkages
    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2252—Sulfonate ligands
    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2252—Sulfonate ligands
    • B01J31/2256—Sulfonate ligands being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional ligands
    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/226—Sulfur, e.g. thiocarbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides 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
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/09—Sulfonamides 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/44—Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
    • 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
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
    • B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/26—Zinc
    • 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
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/31—Aluminium
    • 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
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/32—Gallium
    • 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
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/33—Indium
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/42—Tin
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/48—Zirconium

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

Organometallic complexes characterized by being represented by the general formula (1), which can be advantageously used in the systems of synthesis of carboxylic esters from aldehydes, e.g., Tishchenko’s reaction: (1) wherein M is a metal atom; R is optionally branched C1-8 alkyl or an aromatic or aralkyl group which may be substituted; L is an organic group which has one or more aromatic rings and can form a ring composed of five to seven members inclusive of X, Y, and M; and X and Y are each independently -O-, -NR1-, -N(SO2R2)-, or the like (with proviso that the cases wherein X and Y are the same are excepted), R1 being optionally branched C1-8 alkyl which may be halogenated and R2 being optionally branched C1-10 alkyl which may be halogenated.
PCT/JP2002/007051 2001-07-25 2002-07-11 Organometallic complexes, catalysts containing the same, and process for preparation of carboxylic esters Ceased WO2003010136A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2001-223862 2001-07-25
JP2001223862 2001-07-25
JP2001292276A JP2003104953A (en) 2001-07-25 2001-09-25 Organometallic complex compound and method for producing carboxylic acid ester using the compound
JP2001-292276 2001-09-25

Publications (1)

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

Family

ID=26619210

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2002/007051 Ceased WO2003010136A1 (en) 2001-07-25 2002-07-11 Organometallic complexes, catalysts containing the same, and process for preparation of carboxylic esters

Country Status (3)

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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004047990A1 (en) * 2002-11-27 2004-06-10 Showa Denko K. K. Catalyst for the preparation of carboxylic esters and process for the preparation of carboxylic esters with the same
CN109331875A (en) * 2018-11-14 2019-02-15 山西大学 A kind of binuclear magnesium metal catalyst and its preparation method and application

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116874411B (en) * 2023-07-13 2024-04-16 西安欧得光电材料有限公司 Synthesis method of 1-bromocarbazole

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 (en) * 1992-02-19 1993-09-07 Mitsui Toatsu Chem Inc Olefin polymerization catalyst and method for producing polyolefin using the same
JPH05295023A (en) * 1992-04-24 1993-11-09 Mitsui Toatsu Chem Inc Solid catalyst for polymerizing olefin and production of polyolefin using the same
DE4238233A1 (en) * 1992-11-12 1994-05-19 Fahlberg List Pharma Gmbh Inhibiting 5- or 15-lipoxygenase or cyclo:oxygenase - using N-sulphonyl-aminophenol derivs., e.g. for treating asthma, inflammation or allergy
US5591848A (en) * 1994-10-07 1997-01-07 The Penn State Research Foundation Spiroconjugated charge-transfer dyes for optical applications
WO1998012190A2 (en) * 1996-09-11 1998-03-26 Krenitsky Pharmaceutical, Inc. Phenoxathiin derivatives as inhibitors of monoamine oxidase

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 (en) * 1992-02-19 1993-09-07 Mitsui Toatsu Chem Inc Olefin polymerization catalyst and method for producing polyolefin using the same
JPH05295023A (en) * 1992-04-24 1993-11-09 Mitsui Toatsu Chem Inc Solid catalyst for polymerizing olefin and production of polyolefin using the same
DE4238233A1 (en) * 1992-11-12 1994-05-19 Fahlberg List Pharma Gmbh Inhibiting 5- or 15-lipoxygenase or cyclo:oxygenase - using N-sulphonyl-aminophenol derivs., e.g. for treating asthma, inflammation or allergy
US5591848A (en) * 1994-10-07 1997-01-07 The Penn State Research Foundation Spiroconjugated charge-transfer dyes for optical applications
WO1998012190A2 (en) * 1996-09-11 1998-03-26 Krenitsky Pharmaceutical, Inc. Phenoxathiin derivatives as inhibitors of monoamine oxidase

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
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 (en) * 2002-11-27 2004-06-10 Showa Denko K. K. Catalyst for the preparation of carboxylic esters and process for the preparation of carboxylic esters with the same
CN109331875A (en) * 2018-11-14 2019-02-15 山西大学 A kind of binuclear magnesium metal catalyst and its preparation method and application

Also Published As

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

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