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).

  • Patent number: 9353139
    Abstract: 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: Grant
    Filed: February 20, 2012
    Date of Patent: May 31, 2016
    Assignee: Umicore AG & Co. KG
    Inventors: Joerg Sundermeyer, Wolf Schorn, Ralf Karch
  • Patent number: 9339804
    Abstract: 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: Grant
    Filed: June 25, 2013
    Date of Patent: May 17, 2016
    Assignee: Umicore AG & Co. KG
    Inventors: Angelino Doppiu, Beate Heil, Andreas Rivas-Nass, Eileen Woerner, Ralf Karch
  • Publication number: 20150315224
    Abstract: 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: Application
    Filed: December 11, 2013
    Publication date: November 5, 2015
    Applicant: Umicore AG & Co. KG
    Inventors: Eileen WOERNER, Ralf KARCH, Andreas RIVAS-NASS, Angelino DOPPIU
  • Patent number: 9163045
    Abstract: 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: Grant
    Filed: April 25, 2013
    Date of Patent: October 20, 2015
    Assignee: UMICORE AG & CO. KG
    Inventors: Eileen Woerner, Timo Ebert, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Juergen Widmer
  • Patent number: 9108985
    Abstract: 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: Grant
    Filed: November 28, 2012
    Date of Patent: August 18, 2015
    Assignee: UMICORE AG & CO, KG
    Inventors: Ralf Karch, Andreas Rivas-Nass, Annika Frey, Tobias Burkert, Eileen Woerner, Angelino Doppiu
  • Publication number: 20150190795
    Abstract: 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: Application
    Filed: June 25, 2013
    Publication date: July 9, 2015
    Inventors: Angelino Doppiu, Beate Heil, Andreas Rivas-Nass, Eileen Woerner, Ralf Karch
  • Publication number: 20150141685
    Abstract: 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: Application
    Filed: April 25, 2013
    Publication date: May 21, 2015
    Inventors: Eileen Woerner, Timo Ebert, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Juergen Widmer
  • Publication number: 20140371462
    Abstract: 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: Application
    Filed: August 28, 2014
    Publication date: December 18, 2014
    Inventors: Roland WINDE, Angelino DOPPIU, Eileen WOERNER, Andreas RIVAS-NASS, Ralf KARCH, Christian SLUGOVC, Christina (NEE, LEXER) SCHINAGL
  • Patent number: 8884044
    Abstract: 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: Grant
    Filed: March 26, 2009
    Date of Patent: November 11, 2014
    Assignee: Umicore AG & Co. KG
    Inventors: Andreas Rivas-Nass, Ralf Karch, Roland Winde, Angelino Doppiu, Tina Schneider
  • Patent number: 8846938
    Abstract: 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: Grant
    Filed: May 4, 2010
    Date of Patent: September 30, 2014
    Assignees: Umicore AG & Co. KG, Graz University of Technology
    Inventors: Roland Winde, Angelino Doppiu, Eileen Woerner, Andreas Rivas-Nass, Ralf Karch, Christian Slugovc, Christina Schinagl
  • Publication number: 20140287141
    Abstract: 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: Application
    Filed: November 28, 2012
    Publication date: September 25, 2014
    Applicant: Umicore AG. & Co. KG
    Inventors: Ralf Karch, Andreas Rivas-Nass, Annika Frey, Tobias Burkert, Eileen Woerner, Angelino Doppiu
  • Publication number: 20140256974
    Abstract: 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: Application
    Filed: November 28, 2012
    Publication date: September 11, 2014
    Inventors: Ralf Karch, Andreas Rivas-Nass, Annika Frey, Tobias Burkert, Eileen Woerner, Angelino Doppiu
  • Patent number: 8829220
    Abstract: 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: Grant
    Filed: May 30, 2009
    Date of Patent: September 9, 2014
    Assignee: Umicore AG & Co., KG
    Inventors: Angelino Doppiu, Andreas Rivas-Nass, Ralf Karch, Roland Winde
  • Patent number: 8716509
    Abstract: 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: Grant
    Filed: November 11, 2010
    Date of Patent: May 6, 2014
    Assignee: Umicore AG & Co. KG
    Inventors: Angelino Doppiu, Andreas Rivas-Nass, Ralf Karch, Roland Winde, Eileen Woerner
  • Patent number: 8703985
    Abstract: 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: Grant
    Filed: October 2, 2009
    Date of Patent: April 22, 2014
    Assignee: Umicore AG & Co. KG
    Inventors: Roland Winde, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Gerhard Peter, Eileen Woerner
  • Publication number: 20140051878
    Abstract: 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: Application
    Filed: February 20, 2012
    Publication date: February 20, 2014
    Inventors: Joerg Sundermeyer, Wolf Schorn, Ralf Karch
  • Patent number: 8536344
    Abstract: 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: Grant
    Filed: September 10, 2012
    Date of Patent: September 17, 2013
    Assignee: Umicore AG & Co. KG
    Inventors: Dieter Arlt, Michal Bieniek, Ralf Karch
  • Publication number: 20130211096
    Abstract: 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: Application
    Filed: September 10, 2012
    Publication date: August 15, 2013
    Inventors: Dieter Arlt, Michal Bieniek, Ralf Karch
  • Patent number: 8455671
    Abstract: 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: Grant
    Filed: May 8, 2008
    Date of Patent: June 4, 2013
    Assignee: Umicore AG & Co. KG
    Inventors: Albrecht Salzer, Angelino Doppiu, Nadine Langenscheidt, Andreas Rivas-Nass, Ralf Karch, Roland Winde, Stefanie Mayrhofer
  • Publication number: 20120277456
    Abstract: 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: Application
    Filed: November 11, 2010
    Publication date: November 1, 2012
    Applicant: UMICORE AG & CO. KG
    Inventors: Angelino Doppiu, Andreas Rivas-Nass, Ralf Karch, Roland Winde, Eileen Woerner