Title:
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
Document Type and Number:
WIPO Patent Application WO/2019/138000
Kind Code:
A1
Abstract:
The present invention relates to the use of a transition metal catalyst TMC1, which comprises a transition metal M selected from metals of groups 7, 8, 9 and 10 of the periodic table of elements according to IUPAC and a tetradentate ligand of formula I wherein R1 are identical or different and are each an organic radical having from 1 to 40 carbon atoms, and R2 are identical or different and are each an organic radical having from 1 to 40 carbon atoms, as catalyst in processes for formation of compounds comprising at least one carboxylic acid ester functional group -O-C(=O)- starting from at least one primary alcohol and/or hydrogenation of compounds comprising at least one carboxylic acid ester functional group -O-C(=O)-. The present invention further relates to a process for hydrogenation of a compound comprising at least one carboxylic acid ester functional group -O-C(=O)-, to a process for the formation of a compound comprising at least one carboxylic acid ester functional group -O-C(=O)- by dehydrogenase coupling of at least one primary alcohol with a second alcoholic OH-group, to a transition metal complex comprising the tetradentate ligand of formula I and to a process for preparing said transition metal complex.
More Like This:
| WO/2000/027778 | RESOLUTION METHOD FOR A RACEMIC MIXTURE OF ALDEHYDES |
| WO/2012/170300 | IMPROVEMENT IN METAL-LIGAND CATALYST FORMATION |
Inventors:
SCHAUB THOMAS (DE)
ANABY AVIEL (DE)
SCHELWIES MATHIAS (DE)
PACIELLO ROCCO (DE)
SCHWABEN JONAS (DE)
HASHMI A STEPHEN K (DE)
ANABY AVIEL (DE)
SCHELWIES MATHIAS (DE)
PACIELLO ROCCO (DE)
SCHWABEN JONAS (DE)
HASHMI A STEPHEN K (DE)
Application Number:
PCT/EP2019/050552
Publication Date:
July 18, 2019
Filing Date:
January 10, 2019
Export Citation:
Assignee:
BASF SE (DE)
International Classes:
B01J31/18; B01J31/20; C07C29/149; C07C67/40; B01J31/12
Domestic Patent References:
| WO2006106484A1 | 2006-10-12 | |||
| WO2013023307A1 | 2013-02-21 | |||
| WO2016035080A1 | 2016-03-10 | |||
| WO2012052996A2 | 2012-04-26 |
Foreign References:
| US20160288111A1 | 2016-10-06 | |||
| US20110237814A1 | 2011-09-29 | |||
| US20150202609A1 | 2015-07-23 | |||
| US8471048B2 | 2013-06-25 | |||
| US20160326199A1 | 2016-11-10 | |||
| US20170073298A1 | 2017-03-16 | |||
| EP1868964A1 | 2007-12-26 | |||
| EP1868965A1 | 2007-12-26 | |||
| US8524953B2 | 2013-09-03 |
Other References:
MARTIN J HANTON ET AL: "Ruthenium-catalysed hydrogenation of esters using tripodal phosphine ligands", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, ELSEVIER, AMSTERDAM, NL, vol. 346, no. 1, 22 June 2011 (2011-06-22), pages 70 - 78, XP028258403, ISSN: 1381-1169, [retrieved on 20110629], DOI: 10.1016/J.MOLCATA.2011.06.010
HENRY FONG ET AL: "Hydricity of an Fe-H Species and Catalytic CO 2 Hydrogenation", INORGANIC CHEMISTRY, vol. 54, no. 11, 31 December 2014 (2014-12-31), EASTON, US, pages 5124 - 5135, XP055492598, ISSN: 0020-1669, DOI: 10.1021/ic502508p
MACBETH C E ET AL: "Synthesis and characterization of cationic iron complexes supported by the neutral ligands NPi-Pr3, NArPi-Pr3, and NSt-Bu3", CANADIAN JOURNAL OF CHEMISTRY, vol. 83, no. 4, 23 March 2005 (2005-03-23), pages 332 - 340, XP009506845, DOI: 10.1139/v05-017
DAHLENBURG L ET AL: "Oligophosphan-Liganden", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 411, no. 3, 9 July 1991 (1991-07-09), pages 457 - 469, XP026639028, ISSN: 0022-328X, [retrieved on 19910709]
C BIANCHINI ET AL: "Cobalt(II) and Nickel(II) Complexes with Tris(2-diethylphosphinoethyl)amine. Crystal and Molecular Structure of the Trinuclear Complex [Ni3(Etnp3)2Cl4]-(BPh4)2", INORGANICA CHIMICA ACTA LAUSANNE, 1 January 1980 (1980-01-01), pages 223 - 228, XP055492581, Retrieved from the Internet [retrieved on 20180713], DOI: 10.1016/S0020-1693(00)90533-4
BIANCHINI C ET AL: "Radial trinuclear complexes of cobalt(II) and nickel(ll) with tris(2-dimethylphosphinoethyl)- amine", INORGANICA CHIMICA ACTA, ELSEVIER BV, NL, vol. 31, 1 January 1978 (1978-01-01), pages L433 - L434, XP026623205, ISSN: 0020-1693, [retrieved on 19780101], DOI: 10.1016/S0020-1693(00)94951-X
BERNARDO FONTAL: "COMPLEJOS DE RUTENIO CON FOSFINAS POLIDENTADAS", ACTA CIENTIFICA VENEZOLANA, ASOCIACION VENEZOLANA PARA EL AVANCE DE LA CIENCIA, CARACAS, VE, vol. 33, no. 3, 1 January 1982 (1982-01-01), pages 202 - 213, XP009506569, ISSN: 0001-5504
ANGEW. CHEM. INT. ED., vol. 52, 2013, pages 2538 - 2542
ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 1113 - 1115
ANGEW. CHEM. INT. ED., vol. 46, 2007, pages 7473 - 7476
CHEM. COMMUN., 1997, pages 667
J. MOL. CATAL., vol. 346, 2011, pages 70
ORGANOMETALLICS, vol. 35, 2016, pages 982 - 989
ACTA CIENT. VENEZOLANA, vol. 33, 1982, pages 202 - 213
K. HENKEL: "Ullmann's Encyclopedia of Industrial Chemistry", 2005, WILEY-VCH VERLAG GMBH & CO. KGAA, article "Reactor Types and Their Industrial Applications"
HENRY FONG ET AL: "Hydricity of an Fe-H Species and Catalytic CO 2 Hydrogenation", INORGANIC CHEMISTRY, vol. 54, no. 11, 31 December 2014 (2014-12-31), EASTON, US, pages 5124 - 5135, XP055492598, ISSN: 0020-1669, DOI: 10.1021/ic502508p
MACBETH C E ET AL: "Synthesis and characterization of cationic iron complexes supported by the neutral ligands NPi-Pr3, NArPi-Pr3, and NSt-Bu3", CANADIAN JOURNAL OF CHEMISTRY, vol. 83, no. 4, 23 March 2005 (2005-03-23), pages 332 - 340, XP009506845, DOI: 10.1139/v05-017
DAHLENBURG L ET AL: "Oligophosphan-Liganden", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 411, no. 3, 9 July 1991 (1991-07-09), pages 457 - 469, XP026639028, ISSN: 0022-328X, [retrieved on 19910709]
C BIANCHINI ET AL: "Cobalt(II) and Nickel(II) Complexes with Tris(2-diethylphosphinoethyl)amine. Crystal and Molecular Structure of the Trinuclear Complex [Ni3(Etnp3)2Cl4]-(BPh4)2", INORGANICA CHIMICA ACTA LAUSANNE, 1 January 1980 (1980-01-01), pages 223 - 228, XP055492581, Retrieved from the Internet
BIANCHINI C ET AL: "Radial trinuclear complexes of cobalt(II) and nickel(ll) with tris(2-dimethylphosphinoethyl)- amine", INORGANICA CHIMICA ACTA, ELSEVIER BV, NL, vol. 31, 1 January 1978 (1978-01-01), pages L433 - L434, XP026623205, ISSN: 0020-1693, [retrieved on 19780101], DOI: 10.1016/S0020-1693(00)94951-X
BERNARDO FONTAL: "COMPLEJOS DE RUTENIO CON FOSFINAS POLIDENTADAS", ACTA CIENTIFICA VENEZOLANA, ASOCIACION VENEZOLANA PARA EL AVANCE DE LA CIENCIA, CARACAS, VE, vol. 33, no. 3, 1 January 1982 (1982-01-01), pages 202 - 213, XP009506569, ISSN: 0001-5504
ANGEW. CHEM. INT. ED., vol. 52, 2013, pages 2538 - 2542
ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 1113 - 1115
ANGEW. CHEM. INT. ED., vol. 46, 2007, pages 7473 - 7476
CHEM. COMMUN., 1997, pages 667
J. MOL. CATAL., vol. 346, 2011, pages 70
ORGANOMETALLICS, vol. 35, 2016, pages 982 - 989
ACTA CIENT. VENEZOLANA, vol. 33, 1982, pages 202 - 213
K. HENKEL: "Ullmann's Encyclopedia of Industrial Chemistry", 2005, WILEY-VCH VERLAG GMBH & CO. KGAA, article "Reactor Types and Their Industrial Applications"
Attorney, Agent or Firm:
BASF IP ASSOCIATION (DE)
Download PDF: