Patents by Inventor Ralf Karch
Ralf Karch has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 9353139Abstract: The invention relates to new metal complexes having N-aminoamidinate ligands, more particularly metal complexes having N,N?-bis(dimethylamino)acetamidinate, N,N?-bis(dimethylamino)formamidinate, N-dimethylaminoacetamidinate or N-dimethylamino-N?-isopropyl-acetamidinate ligands as well as to their preparation and use. The metal complexes are characterized by a five-membered chelate ring. The metal complexes are formed with the metals from the main groups of the PTE, but also with transition-group elements such as tantalum (Ta), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu) or zinc (Zn), and also with precious metals such as palladium (Pd). The complexes of the invention find use as precursors for the preparation of functional layers by means of gas-phase thin-film processes such as CVD, MO-CVD and ALD. Additionally they may be used as catalysts for olefin hydroamination and for olefin polymerization.Type: GrantFiled: February 20, 2012Date of Patent: May 31, 2016Assignee: Umicore AG & Co. KGInventors: Joerg Sundermeyer, Wolf Schorn, Ralf Karch
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Patent number: 9339804Abstract: The present invention is directed to a method for the preparation of ruthenium catalyst (PCy3)2CI2Ru(phenylindenylidene) (Umicore catalyst “M1”). The method comprises a one-step reaction reacting the precursor compound (PPh3)2CI2Ru(3-phenylindenylidene) with PCy3 in a cyclic ether solvent (preferably THF) in concentrations in the range of 0.2 to 0.6 mol catalyst/I while simultaneously precipitating the product from the reaction mixture. A cyclic ether solvate product with high crystallinity and high purity is obtained.Type: GrantFiled: June 25, 2013Date of Patent: May 17, 2016Assignee: Umicore AG & Co. KGInventors: Angelino Doppiu, Beate Heil, Andreas Rivas-Nass, Eileen Woerner, Ralf Karch
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Publication number: 20150315224Abstract: The invention relates to a method for producing aqueous preparations of complexes of platinum group metals (PGM) Pt, Pd, Rh and Ir having the general formula [MA/MB/MC(L)a(H2O)b(O2—)c(OH?)d](OH—)e(H+)f, wherein MA=PtII or PdII, MB=PtIV, MC=Rh or Ir, L is a neutral monodentate or bidentate donor ligand, and a is an integer between 1 and 4 (or 2) and/or between 1 and 6 (or 3), b is an integer between 0 and 3 (or 5), c is an integer between 0 and 3 (or 4), d is an integer between 0 and 3 (or 5), e is an integer between 0 and 2 (or 3 or 4) and f is an integer between 0 and 4 (or 5). In the method according to the invention, the hydroxo complexes H2Pd(OH)4 (in the case of MA=PdII), H2Pt(OH)6 (in the case of MA=PtII and MB=PtIV) or H3MC(OH)6 (for MC=RhIIIIrIII) are converted in the presence of the donor ligands, wherein at least one hydroxo group of the hydro complex is exchanged. Preferably, the reaction occurs at temperatures in the range of 40 to 110° C.Type: ApplicationFiled: December 11, 2013Publication date: November 5, 2015Applicant: Umicore AG & Co. KGInventors: Eileen WOERNER, Ralf KARCH, Andreas RIVAS-NASS, Angelino DOPPIU
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Patent number: 9163045Abstract: The invention relates to a process for preparing diketonato-rhodium(I)-carbonyl complexes, especially diketonato-rhodium(I)-triorganophosphine-carbonyl complexes, for example Rh(CO)(PPh3)acac. The process according to the invention is a “one-pot synthesis” and features a process procedure without intermediate isolation stages. After introduction of an Rh(III) halide precursor into a solvent and sparging with carbon monoxide (CO), a diketo compound of the R?—C(?O)—CH2—C(?O)—R? type and a base are added, forming the intermediate compound diketonato-Rh(CO)2. After addition of a triorganophosphine of the PR3 type, the reaction mixture is heated and the diketonatocarbonyltriorganophosphine-rhodium(I) complex is removed. The process enables a rapid operation and a high yield. The complex Rh(CO)(PPh3)acac prepared in accordance with the invention, because of its purity, is particularly suitable as a catalyst or precatalyst for homogeneous catalysis, for example for hydroformylation reactions.Type: GrantFiled: April 25, 2013Date of Patent: October 20, 2015Assignee: UMICORE AG & CO. KGInventors: Eileen Woerner, Timo Ebert, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Juergen Widmer
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Patent number: 9108985Abstract: The invention relates to a process for preparing trialkylgallium compounds of the general formula R3Ga. The process is based on the reaction of gallium trichloride (GaCh), optionally in a mixture with partially alkylated products, with an alkylaluminium compound of the type RaAICIb (where R?C1-C5-alkyl, a=1, 2 or 3, b=0, 1 or 2 and a+b=3) in the presence of at least two alkali metal halides (e.g. NaCI and KCI) as auxiliary base. Preference is given to using alkylaluminium sesquichloride (R3AI2CI3) or trialkylaluminium (R3AI). The reaction mixture is heated to a temperature in the range from 120° C. to 250° C. and the trialkylgallium compound formed is separated off via a separator which is operated at a temperature which is more than 30° C. below the boiling point of the most volatile partially alkylated product. Complete alkylation is achieved here and partially alkylated products are recirculated to the reaction mixture. In a further step, the reaction mixture can be heated to a maximum of 350° C.Type: GrantFiled: November 28, 2012Date of Patent: August 18, 2015Assignee: UMICORE AG & CO, KGInventors: Ralf Karch, Andreas Rivas-Nass, Annika Frey, Tobias Burkert, Eileen Woerner, Angelino Doppiu
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Publication number: 20150190795Abstract: The present invention is directed to a method for the preparation of ruthenium catalyst (PCy3)2CI2Ru(phenylindenylidene) (Umicore catalyst “M1”). The method comprises a one-step reaction reacting the precursor compound (PPh3)2CI2Ru(3-phenylindenylidene) with PCy3 in a cyclic ether solvent (preferably THF) in concentrations in the range of 0.2 to 0.6 mol catalyst/l while simultaneously precipitating the product from the reaction mixture. A cyclic ether solvate product with high crystallinity and high purity is obtained.Type: ApplicationFiled: June 25, 2013Publication date: July 9, 2015Inventors: Angelino Doppiu, Beate Heil, Andreas Rivas-Nass, Eileen Woerner, Ralf Karch
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Publication number: 20150141685Abstract: The invention relates to a process for preparing diketonato-rhodium(I)-carbonyl complexes, especially diketonato-rhodium(I)-triorganophosphine-carbonyl complexes, for example Rh(CO)(PPh3)acac. The process according to the invention is a “one-pot synthesis” and features a process procedure without intermediate isolation stages. After introduction of an Rh(III) halide precursor into a solvent and sparging with carbon monoxide (CO), a diketo compound of the R?—C(?O)—CH2—C(?O)—R? type and a base are added, forming the intermediate compound diketonato-Rh(CO)2. After addition of a triorganophosphine of the PR3 type, the reaction mixture is heated and the diketonatocarbonyltriorganophosphine-rhodium(I) complex is removed. The process enables a rapid operation and a high yield. The complex Rh(CO)(PPh3)acac prepared in accordance with the invention, because of its purity, is particularly suitable as a catalyst or precatalyst for homogeneous catalysis, for example for hydroformylation reactions.Type: ApplicationFiled: April 25, 2013Publication date: May 21, 2015Inventors: Eileen Woerner, Timo Ebert, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Juergen Widmer
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Publication number: 20140371462Abstract: The invention relates to a method for preparation of ruthenium-based carbene catalysts with a chelating alkylidene ligand (“Hoveyda-type catalysts”) by reacting a penta coordinated ruthenium (II)-alkylidene complex of the type (1) (Py)X1X2Ru(alkylidene) with a suitable olefin derivative in a cross metathesis reaction. The method delivers high yields and is conducted preferably in aromatic hydrocarbon solvents. The use of phosphine-containing Ru carbene complexes as starting materials can be avoided. Catalyst products with high purity, particularly with low Cu content, can be obtained.Type: ApplicationFiled: August 28, 2014Publication date: December 18, 2014Inventors: Roland WINDE, Angelino DOPPIU, Eileen WOERNER, Andreas RIVAS-NASS, Ralf KARCH, Christian SLUGOVC, Christina (NEE, LEXER) SCHINAGL
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Patent number: 8884044Abstract: The invention relates to ruthenium complexes which have a chiral diphosphorus donor ligand and in which the ruthenium has the oxidation state (+11) and the chiral diphosphorus donor ligand has bidentate P—P coordination to the ruthenium. The ruthenium complexes are present in two forms (cationic type A and uncharged type B), are cyclic and have a four- to six-membered ring incorporating the diphosphorus donor ligand. The chiral diphosphorus donor ligands are selected from the group consisting of diphosphines, diphospholanes, diphosphites, diphosphonites and diazaphospholanes. Furthermore, processes for preparing the ruthenium complexes of types A and B, which are based on ligand exchange reactions, are described. The Ru complexes are used as catalysts for homogeneous asymmetric catalysis for preparing organic compounds.Type: GrantFiled: March 26, 2009Date of Patent: November 11, 2014Assignee: Umicore AG & Co. KGInventors: Andreas Rivas-Nass, Ralf Karch, Roland Winde, Angelino Doppiu, Tina Schneider
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Patent number: 8846938Abstract: The invention relates to a method for preparation of ruthenium-based carbene catalysts with a chelating alkylidene ligand (“Hoveyda-type catalysts”) by reacting a penta-coordinated ruthenium (II)-alkylidene complex of the type (L) (Py)X1X2Ru(alkylidene) with a suitable olefin derivative in a cross metathesis reaction. The method delivers high yields and is conducted preferably in aromatic hydrocarbon solvents. The use of phosphine-containing Ru carbene complexes as starting materials can be avoided. Catalyst products with high purity, particularly with low Cu content, can be obtained.Type: GrantFiled: May 4, 2010Date of Patent: September 30, 2014Assignees: Umicore AG & Co. KG, Graz University of TechnologyInventors: Roland Winde, Angelino Doppiu, Eileen Woerner, Andreas Rivas-Nass, Ralf Karch, Christian Slugovc, Christina Schinagl
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Publication number: 20140287141Abstract: The invention relates to a process for preparing trialkylmetal compounds of the general formula R3M (where M=metal of group IIIA of the Periodic Table of the Elements (PTE), preferably gallium or indium, and R?C1-C5-alkyl, preferably methyl or ethyl). The process is based on the reaction of metal trichloride (MeCl3) with alkylaluminium sesquichloride (R3Al2Cl3) in the presence of at least one alkali metal halide as auxiliary base. The reaction mixture is heated to a temperature above 120° C. and the trialkylmetal compound is separated off from the reaction mixture via a separator, with partially alkylated products being at the same time recirculated to the reaction mixture. In a further step, the reaction mixture is heated to a maximum of 350° C. and the remaining alkylated and partially alkylated products are separated off. The products obtained in this way can optionally be recycled in the process.Type: ApplicationFiled: November 28, 2012Publication date: September 25, 2014Applicant: Umicore AG. & Co. KGInventors: Ralf Karch, Andreas Rivas-Nass, Annika Frey, Tobias Burkert, Eileen Woerner, Angelino Doppiu
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Publication number: 20140256974Abstract: The invention relates to a process for preparing trialkylgallium compounds of the general formula R3Ga. The process is based on the reaction of gallium trichloride (GaCh), optionally in a mixture with partially alkylated products, with an alkylaluminium compound of the type RaAlClb (where R?C1-C5-alkyl, a=1, 2 or 3, b=0, 1 or 2 and a+b=3) in the presence of at least two alkali metal halides (e.g. NaCl and KCl) as auxiliary base. Preference is given to using alkylaluminium sesquichloride (R3Al2Cl3) or trialkylaluminium (R3Al). The reaction mixture is heated to a temperature in the range from 120° C. to 250° C. and the trialkylgallium compound formed is separated off via a separator which is operated at a temperature which is more than 30° C. below the boiling point of the most volatile partially alkylated product. Complete alkylation is achieved here and partially alkylated products are recirculated to the reaction mixture. In a further step, the reaction mixture can be heated to a maximum of 350° C.Type: ApplicationFiled: November 28, 2012Publication date: September 11, 2014Inventors: Ralf Karch, Andreas Rivas-Nass, Annika Frey, Tobias Burkert, Eileen Woerner, Angelino Doppiu
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Patent number: 8829220Abstract: The present invention relates to a single-stage process for preparing dienyl-ruthenium complexes of the formula Ru(+II)(dienyl)2, wherein an Ru(II) starting compound of the formula Ru(X)p(Y)q is reacted with a diene ligand in the presence of an inorganic and/or organic base in a single-stage process. Here, polar organic solvents, preferably mixtures of polar organic solvents with water, are used. The dienyl-ruthenium complexes prepared according to the invention are used as precursors for homogeneous catalysts, for producing functional coatings and for therapeutic applications.Type: GrantFiled: May 30, 2009Date of Patent: September 9, 2014Assignee: Umicore AG & Co., KGInventors: Angelino Doppiu, Andreas Rivas-Nass, Ralf Karch, Roland Winde
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Patent number: 8716509Abstract: The present invention relates to a process for preparing ruthenium(0)-olefin complexes of the (arene)(diene)Ru(0) type by reacting a ruthenium starting compound of the formula Ru(+II)(X)p(Y)q (in which X=an anionic group, Y=an uncharged two-electron donor ligand, p=1 or 2, q=an integer from 1 to 6), with a cyclohexadiene derivative or a diene mixture comprising a cyclohexadiene derivative, in the presence of a base. In this process, the arene bound in the (arene)(diene)Ru(0) complex is formed from this cyclohexadiene derivative by oxidation. Suitable ruthenium(II) starting compounds are, for example, RuCl2(acetonitrile)4, RuCl2(pyridine)4 or RuCl2(DMSO)4. The bases used are inorganic or organic bases. The ruthenium(0)-olefin complexes prepared by the process according to the invention have a high purity and can be used as precursors for homogeneous catalysts, for preparation of functional ruthenium- or ruthenium oxide-containing layers and for therapeutic applications.Type: GrantFiled: November 11, 2010Date of Patent: May 6, 2014Assignee: Umicore AG & Co. KGInventors: Angelino Doppiu, Andreas Rivas-Nass, Ralf Karch, Roland Winde, Eileen Woerner
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Patent number: 8703985Abstract: The present invention is directed to a method for the preparation of ruthenium indenylidene carbene catalysts of the type (L)(L?)X2Ru(II)(aryl-indenylidene). The method comprises the steps of reacting the precursor compound Ru(PPh3)nX2 (n=3-4) with a propargyl alcohol derivative in an cyclic diether solvent such as 1,4-dioxane at temperatures in the range of 80 to 130° C. and reaction times of 1 to 60 minutes. Optionally, additional neutral electron donor ligands such as PCy3, phobane ligands or NHC ligands are added to the reaction mixture for ligand exchange. The method includes a precipitation step for purification, after which the product is isolated. The ruthenium-indenylidene carbene catalysts are obtained in high purity and are used as catalysts for metathesis reactions (RCM, ROMP and CM) and as precursors for the synthesis of modified ruthenium carbene catalysts.Type: GrantFiled: October 2, 2009Date of Patent: April 22, 2014Assignee: Umicore AG & Co. KGInventors: Roland Winde, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Gerhard Peter, Eileen Woerner
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Publication number: 20140051878Abstract: The invention relates to new metal complexes having N-aminoamidinate ligands, more particularly metal complexes having N,N?-bis(dimethylamino)acetamidinate, N,N?-bis(dimethylamino)formamidinate, N-dimethylaminoacetamidinate or N-dimethylamino-N?-isopropyl-acetamidinate ligands as well as to their preparation and use. The metal complexes are characterized by a five-membered chelate ring. The metal complexes are formed with the metals from the main groups of the PTE, but also with transition-group elements such as tantalum (Ta), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu) or zinc (Zn), and also with precious metals such as palladium (Pd). The complexes of the invention find use as precursors for the preparation of functional layers by means of gas-phase thin-film processes such as CVD, MO-CVD and ALD. Additionally they may be used as catalysts for olefin hydroamination and for olefin polymerization.Type: ApplicationFiled: February 20, 2012Publication date: February 20, 2014Inventors: Joerg Sundermeyer, Wolf Schorn, Ralf Karch
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Patent number: 8536344Abstract: There is disclosed compounds of formula 1, their preparation, intermediates for the preparation and the use of the compounds of the formula 1 as catalysts in various metathesis reactions. The novel metathesis catalysts, which are obtained from readily available precursors, have a high activity and can be used for any type of metathesis reaction.Type: GrantFiled: September 10, 2012Date of Patent: September 17, 2013Assignee: Umicore AG & Co. KGInventors: Dieter Arlt, Michal Bieniek, Ralf Karch
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Publication number: 20130211096Abstract: There is disclosed compounds of formula 1, their preparation, intermediates for the preparation and the use of the compounds of the formula 1 as catalysts in various metathesis reactions. The novel metathesis catalysts, which are obtained from readily available precursors, have a high activity and can be used for any type of metathesis reaction.Type: ApplicationFiled: September 10, 2012Publication date: August 15, 2013Inventors: Dieter Arlt, Michal Bieniek, Ralf Karch
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Patent number: 8455671Abstract: The invention relates to ruthenium complexes with a chiral ferrocenyldiphosphine ligand, wherein the ruthenium has the oxidation state (+II) and the chiral ferrocenyldiphosphine ligand has bidentate P—P coordination to the ruthenium. The ruthenium complexes are cyclic and with the ferrocenyldiphosphine ligand have an at least eight-membered ring. The ferrocenyldiphosphine ligands are selected from the group consisting of Taniaphos, Taniaphos-OH and Walphos ligands. A process for preparing the Ru complexes is described. The Rn complexes are used as catalysts for homogeneous asymmetric catalysis for preparing organic compounds.Type: GrantFiled: May 8, 2008Date of Patent: June 4, 2013Assignee: Umicore AG & Co. KGInventors: Albrecht Salzer, Angelino Doppiu, Nadine Langenscheidt, Andreas Rivas-Nass, Ralf Karch, Roland Winde, Stefanie Mayrhofer
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Publication number: 20120277456Abstract: The present invention relates to a process for preparing ruthenium(0)-olefin complexes of the (arene)(diene)Ru(0) type by reacting a ruthenium starting compound of the formula Ru(+II)(X)p(Y)q (in which X=an anionic group, Y=an uncharged two-electron donor ligand, p=1 or 2, q=an integer from 1 to 6), with a cyclohexadiene derivative or a diene mixture comprising a cyclohexadiene derivative, in the presence of a base. In this process, the arene bound in the (arene)(diene)Ru(0) complex is formed from this cyclohexadiene derivative by oxidation. Suitable ruthenium(II) starting compounds are, for example, RuCl2(acetonitrile)4, RuCl2(pyridine)4 or RuCl2(DMSO)4. The bases used are inorganic or organic bases. The ruthenium(0)-olefin complexes prepared by the process according to the invention have a high purity and can be used as precursors for homogeneous catalysts, for preparation of functional ruthenium- or ruthenium oxide-containing layers and for therapeutic applications.Type: ApplicationFiled: November 11, 2010Publication date: November 1, 2012Applicant: UMICORE AG & CO. KGInventors: Angelino Doppiu, Andreas Rivas-Nass, Ralf Karch, Roland Winde, Eileen Woerner