Title:
VANADIUM CATALYSTS AND PROCESS FOR THE DIRECT CONVERSION OF METHANE INTO ACETIC ACID
Document Type and Number:
WIPO Patent Application WO2004037416
Kind Code:
A3
Abstract:
The invention consists on the utilization of complexes of vanadium (in the +4 and +5 oxidation states) with bi- or poly-dentate ligands coordinated by nitrogen and oxygen (N,O) or by oxygen and oxygen (O,O) atoms, namely derivaties of aminoalcohols, (hydroxyimino)dicarboxylic acids, hydroxypyranones, trifluoroacetic acid, triflic acid or inorganic acid, as catalysts for the direct single-pot conversion, under mild conditions, of methane in acetic acid, either in the absence or in the presence of carbon monoxide, and in the presence of a peroxodisulfate salt (K2S2O8), in trifluoroacetic acid (CF3COOH), according to the general reaction (I).
Inventors:
POMBEIRO ARMANDO (PT)
FRAUSTO DA SILVA JOAO (PT)
FUJIWARA YUZO (JP)
SILVA JOSE ARMANDO (PT)
REIS PATRICIA M (PT)
PALAVRA ANTONIO F (PT)
FRAUSTO DA SILVA JOAO (PT)
FUJIWARA YUZO (JP)
SILVA JOSE ARMANDO (PT)
REIS PATRICIA M (PT)
PALAVRA ANTONIO F (PT)
Application Number:
PCT/PT2003/000015
Publication Date:
August 12, 2004
Filing Date:
October 15, 2003
Export Citation:
Assignee:
INST SUPERIOR TECNICO (PT)
POMBEIRO ARMANDO (PT)
FRAUSTO DA SILVA JOAO (PT)
FUJIWARA YUZO (JP)
SILVA JOSE ARMANDO (PT)
REIS PATRICIA M (PT)
PALAVRA ANTONIO F (PT)
POMBEIRO ARMANDO (PT)
FRAUSTO DA SILVA JOAO (PT)
FUJIWARA YUZO (JP)
SILVA JOSE ARMANDO (PT)
REIS PATRICIA M (PT)
PALAVRA ANTONIO F (PT)
International Classes:
B01J31/04; B01J31/22; B01J31/36; C07C51/285; (IPC1-7): B01J31/04; B01J31/18; B01J31/22; B01J31/26; B01J31/36; C07C51/145
Foreign References:
| EP0560656A2 | 1993-09-15 |
Other References:
TANIGUCHI Y ET AL: "Highly Efficient Vanadium-Catalyzed Transformation of CH4 and CO to Acetic Acid", ORGANIC LETTERS, ACS, WASHINGTON, DC, US, vol. 1, no. 4, 8 July 1999 (1999-07-08), pages 557 - 559, XP002286128
NIZOVA G V ET AL: "Carboxylation of methane with CO or CO2 in aqueous solution catalysed by vanadium complexes", CHEMICAL COMMUNICATIONS - CHEMCOM, ROYAL SOCIETY OF CHEMISTRY, GB, no. 17, 1998, pages 1885 - 1886, XP002286129
REIS P M ET AL: "Amavadine as a catalyst for the peroxidative halogenation, hydroxylation and oxygenation of alkanes and benzene", CHEMICAL COMMUNICATIONS - CHEMCOM, ROYAL SOCIETY OF CHEMISTRY, GB, 2000, pages 1845 - 1846, XP002286130
ASADULLAH M ET AL: "One-step carboxylation reaction of saturated hydrocarbons with CO by Co(OAc)2 catalyst under mild conditions", APPLIED CATALYSIS A: GENERAL, ELSEVIER SCIENCE, AMSTERDAM, NL, vol. 194-195, 13 March 2000 (2000-03-13), pages 443 - 452, XP004272248, ISSN: 0926-860X
ASADULLAH M ET AL: "CaCl2-Catalyzed Functionalization of Saturated Hydrocarbons with CO to Carboxylic Acids and Esters", JOURNAL OF CATALYSIS, ACADEMIC PRESS, DULUTH, MN, US, vol. 195, no. 1, 1 October 2000 (2000-10-01), pages 180 - 186, XP004437974, ISSN: 0021-9517
CRANS D C ET AL: "Vanadium(V)-Protein Model Studies: Solid-State and Solution Structure", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 115, no. 15, 28 July 1993 (1993-07-28), pages 6769 - 6776, XP002286131
BERRY R E ET AL: "The Structural Characterization of Amavadin", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY-VCH VERLAG, WEINHEIM, DE, vol. 38, no. 6, 15 March 1999 (1999-03-15), pages 795 - 797, XP002286132
CARAVAN P ET AL: "Reaction Chemistry of BMOV, Bis(maltolato)oxovanadium(IV)-A Potent Insulin Mimetic Agent", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 117, no. 51, 27 December 1995 (1995-12-27), pages 12759 - 12770, XP002286133
CHEN C-T ET AL: "Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate", ORGANIC LETTERS, ACS, WASHINGTON, DC, US, vol. 3, no. 23, 20 October 2001 (2001-10-20), pages 3729 - 3732, XP002286134
HAMSTRA B J ET AL: "Structural and Solution Characterization of Mononuclear Vanadium(IV) Complexes That Help To Elucidate the Active Site Structure of the Reduced Vanadium Haloperoxidases", INORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 36, no. 21, 8 October 1997 (1997-10-08), pages 4866 - 4874, XP002286135
REIS P M ET AL: "Single-Pot Conversion of Methane into Acetic Acid in the Absence of CO and with Vanadium Catalysts Such as Amavadine", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY-VCH VERLAG, WEINHEIM, DE, vol. 42, no. 7, 17 February 2003 (2003-02-17), pages 821 - 823, XP002286136
CRANS D C ET AL: "The Chemistry and Biochemistry of Vanadium and the Biological Activities Exerted by Vanadium Compounds", CHEMICAL REVIEWS, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 104, no. 2, 29 January 2004 (2004-01-29), pages 849 - 902, XP002286137
NIZOVA G V ET AL: "Carboxylation of methane with CO or CO2 in aqueous solution catalysed by vanadium complexes", CHEMICAL COMMUNICATIONS - CHEMCOM, ROYAL SOCIETY OF CHEMISTRY, GB, no. 17, 1998, pages 1885 - 1886, XP002286129
REIS P M ET AL: "Amavadine as a catalyst for the peroxidative halogenation, hydroxylation and oxygenation of alkanes and benzene", CHEMICAL COMMUNICATIONS - CHEMCOM, ROYAL SOCIETY OF CHEMISTRY, GB, 2000, pages 1845 - 1846, XP002286130
ASADULLAH M ET AL: "One-step carboxylation reaction of saturated hydrocarbons with CO by Co(OAc)2 catalyst under mild conditions", APPLIED CATALYSIS A: GENERAL, ELSEVIER SCIENCE, AMSTERDAM, NL, vol. 194-195, 13 March 2000 (2000-03-13), pages 443 - 452, XP004272248, ISSN: 0926-860X
ASADULLAH M ET AL: "CaCl2-Catalyzed Functionalization of Saturated Hydrocarbons with CO to Carboxylic Acids and Esters", JOURNAL OF CATALYSIS, ACADEMIC PRESS, DULUTH, MN, US, vol. 195, no. 1, 1 October 2000 (2000-10-01), pages 180 - 186, XP004437974, ISSN: 0021-9517
CRANS D C ET AL: "Vanadium(V)-Protein Model Studies: Solid-State and Solution Structure", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 115, no. 15, 28 July 1993 (1993-07-28), pages 6769 - 6776, XP002286131
BERRY R E ET AL: "The Structural Characterization of Amavadin", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY-VCH VERLAG, WEINHEIM, DE, vol. 38, no. 6, 15 March 1999 (1999-03-15), pages 795 - 797, XP002286132
CARAVAN P ET AL: "Reaction Chemistry of BMOV, Bis(maltolato)oxovanadium(IV)-A Potent Insulin Mimetic Agent", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 117, no. 51, 27 December 1995 (1995-12-27), pages 12759 - 12770, XP002286133
CHEN C-T ET AL: "Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate", ORGANIC LETTERS, ACS, WASHINGTON, DC, US, vol. 3, no. 23, 20 October 2001 (2001-10-20), pages 3729 - 3732, XP002286134
HAMSTRA B J ET AL: "Structural and Solution Characterization of Mononuclear Vanadium(IV) Complexes That Help To Elucidate the Active Site Structure of the Reduced Vanadium Haloperoxidases", INORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 36, no. 21, 8 October 1997 (1997-10-08), pages 4866 - 4874, XP002286135
REIS P M ET AL: "Single-Pot Conversion of Methane into Acetic Acid in the Absence of CO and with Vanadium Catalysts Such as Amavadine", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY-VCH VERLAG, WEINHEIM, DE, vol. 42, no. 7, 17 February 2003 (2003-02-17), pages 821 - 823, XP002286136
CRANS D C ET AL: "The Chemistry and Biochemistry of Vanadium and the Biological Activities Exerted by Vanadium Compounds", CHEMICAL REVIEWS, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 104, no. 2, 29 January 2004 (2004-01-29), pages 849 - 902, XP002286137
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