Title:
OXIDATION OF PRIMARY ALIPHATIC ALCOHOLS WITH A NOBLE METAL PLOYOXOMETALATE COMPLEX
Document Type and Number:
WIPO Patent Application WO/2011/039744
Kind Code:
A3
Abstract:
A process of oxidizing primary alcohols to their corresponding aldehydes is disclosed. The process is effected in the presence of noble metal polyoxometalate complexes. A novel process for preparing noble metal polyoxometalate complexes, and novel noble metal polyoxometalate complexes are also disclosed.
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Inventors:
NEUMANN RONNY (IL)
BARATS DELINA (IL)
BARATS DELINA (IL)
Application Number:
PCT/IL2010/000770
Publication Date:
December 29, 2011
Filing Date:
September 19, 2010
Export Citation:
Assignee:
YEDA RES & DEV (IL)
NEUMANN RONNY (IL)
BARATS DELINA (IL)
NEUMANN RONNY (IL)
BARATS DELINA (IL)
International Classes:
C07C45/29; B01J23/652; C07C45/38; C07C47/02; C07C47/21; C07F11/00; C07F15/00
Domestic Patent References:
| WO2003053556A2 | 2003-07-03 | |||
| WO2008128638A1 | 2008-10-30 | |||
| WO1998054165A1 | 1998-12-03 | |||
| WO2007139616A1 | 2007-12-06 |
Foreign References:
| EP1112777A1 | 2001-07-04 | |||
| US20040192972A1 | 2004-09-30 |
Other References:
PILLAI, U.R. ET AL.: "Selective oxidation of alcohols by molecular oxygen over a Pd/MgO catalyst in the absence of any additives", GREEN CHEMISTRY, vol. 6, no. 3, 2004, pages 161 - 165, XP009151300, ISSN: 1463-9262, [retrieved on 20040121], DOI: 10.1039/B316414B
NISHIMURA, T. ET AL.: "Pd(OAc)2-catalyzed oxidation of alcohols to aldehydes and ketones by molecular oxygen", TETRAHEDRON LETTERS, vol. 39, no. 33, 13 August 1998 (1998-08-13), pages 6011 - 6014, XP004126786, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(98)01235-0
HEIKO WEINER ET AL: "An All-Inorganic, Polyoxometalate-Based Catechol Dioxygenase That Exhibits >100 000 Catalytic Turnovers", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 42, 1 October 1999 (1999-10-01), pages 9831 - 9842, XP055004919, ISSN: 0002-7863, DOI: 10.1021/ja991503b
NEUMANN, R. ET AL.: "A ruthenium-substituted polyoxometalate as an inorganic dioxygenase for activation of molecular oxygen", NATURE, vol. 388, no. 6640, 1997, pages 353 - 355, XP009113239, ISSN: 0028-0836, [retrieved on 19970724], DOI: 10.1038/41039
NEUMANN R ET AL: "Molecular oxygen activation by a ruthenium-substituted 'sandwich' type polyoxometalate", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC; US, vol. 120, no. 46, 25 November 1998 (1998-11-25), pages 11969 - 11976, XP009113238, ISSN: 0002-7863, [retrieved on 19981110], DOI: 10.1021/JA974243B
CHAOYING RONG ET AL: "Lacunary polyoxometalate anions are .pi.-acceptor ligands. Characterization of some tungstoruthenate(II,III,IV,V) heteropolyanions and their atom-transfer reactivity", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC; US, vol. 114, no. 8, 1 January 1992 (1992-01-01), pages 2932 - 2938, XP007907529, ISSN: 0002-7863, [retrieved on 20020501], DOI: 10.1021/JA00034A027
NOMIYA, K. ET AL.: "Synthesis and characterization of a monoruthenium(III)-substituted Dawson polyoxotungstate derived by Br2 oxidation of the 1 : 2 complex of ruthenium(II) and [[alpha]2-P2W17O61]<10->. The reactivity of cis-[RuCl12(DMSO)4] as a ruthenium source", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS, no. 9, 7 May 2001 (2001-05-07), pages 1506 - 1512, XP009113232, ISSN: 1472-7773, [retrieved on 20010417], DOI: 10.1039/B009483H
NEUMANN, R. ET AL.: "Noble Metal (RuIII, PdII, PtII) Substituted "Sandwich" Type Polyoxometalates: Preparation, Characterization, and Catalytic Activity in Oxidations of Alkanes and Alkenes by Peroxides", INORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON, US, vol. 34, 1 November 1995 (1995-11-01), pages 5753 - 5760, XP007907528, ISSN: 0020-1669, [retrieved on 20020501], DOI: 10.1021/IC00127A012
TOURNÉ, C.M. ET AL.: "Chiral polytungstometalates [WM3(H2O)2(XW9O34)2]12 (X = M = Zn or CoII) and their M-substituted derivatives. Syntheses, chemical, structural and spectroscopic study of some D,L sodium and potassium salts", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS, 1991, pages 143 - 155, XP009151302, ISSN: 1472-7773, DOI: 10.1039/DT9910000143
NISHIMURA, T. ET AL.: "Pd(OAc)2-catalyzed oxidation of alcohols to aldehydes and ketones by molecular oxygen", TETRAHEDRON LETTERS, vol. 39, no. 33, 13 August 1998 (1998-08-13), pages 6011 - 6014, XP004126786, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(98)01235-0
HEIKO WEINER ET AL: "An All-Inorganic, Polyoxometalate-Based Catechol Dioxygenase That Exhibits >100 000 Catalytic Turnovers", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 42, 1 October 1999 (1999-10-01), pages 9831 - 9842, XP055004919, ISSN: 0002-7863, DOI: 10.1021/ja991503b
NEUMANN, R. ET AL.: "A ruthenium-substituted polyoxometalate as an inorganic dioxygenase for activation of molecular oxygen", NATURE, vol. 388, no. 6640, 1997, pages 353 - 355, XP009113239, ISSN: 0028-0836, [retrieved on 19970724], DOI: 10.1038/41039
NEUMANN R ET AL: "Molecular oxygen activation by a ruthenium-substituted 'sandwich' type polyoxometalate", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC; US, vol. 120, no. 46, 25 November 1998 (1998-11-25), pages 11969 - 11976, XP009113238, ISSN: 0002-7863, [retrieved on 19981110], DOI: 10.1021/JA974243B
CHAOYING RONG ET AL: "Lacunary polyoxometalate anions are .pi.-acceptor ligands. Characterization of some tungstoruthenate(II,III,IV,V) heteropolyanions and their atom-transfer reactivity", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC; US, vol. 114, no. 8, 1 January 1992 (1992-01-01), pages 2932 - 2938, XP007907529, ISSN: 0002-7863, [retrieved on 20020501], DOI: 10.1021/JA00034A027
NOMIYA, K. ET AL.: "Synthesis and characterization of a monoruthenium(III)-substituted Dawson polyoxotungstate derived by Br2 oxidation of the 1 : 2 complex of ruthenium(II) and [[alpha]2-P2W17O61]<10->. The reactivity of cis-[RuCl12(DMSO)4] as a ruthenium source", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS, no. 9, 7 May 2001 (2001-05-07), pages 1506 - 1512, XP009113232, ISSN: 1472-7773, [retrieved on 20010417], DOI: 10.1039/B009483H
NEUMANN, R. ET AL.: "Noble Metal (RuIII, PdII, PtII) Substituted "Sandwich" Type Polyoxometalates: Preparation, Characterization, and Catalytic Activity in Oxidations of Alkanes and Alkenes by Peroxides", INORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON, US, vol. 34, 1 November 1995 (1995-11-01), pages 5753 - 5760, XP007907528, ISSN: 0020-1669, [retrieved on 20020501], DOI: 10.1021/IC00127A012
TOURNÉ, C.M. ET AL.: "Chiral polytungstometalates [WM3(H2O)2(XW9O34)2]12 (X = M = Zn or CoII) and their M-substituted derivatives. Syntheses, chemical, structural and spectroscopic study of some D,L sodium and potassium salts", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS, 1991, pages 143 - 155, XP009151302, ISSN: 1472-7773, DOI: 10.1039/DT9910000143
Attorney, Agent or Firm:
G.E EHRLICH (1995) LTD. et al. (Ramat Gan, IL)
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