Patents by Inventor Frank Geilen

Frank Geilen 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: 10202329
    Abstract: The invention relates to a compound of formula (I) where R1 and R3 are each a heteroaryl radical having five ring atoms, R2 and R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl; R1 and R3 may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen; and R2 and R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl or —(C6-C20)-aryl, may e
    Type: Grant
    Filed: July 19, 2016
    Date of Patent: February 12, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Helfried Neumann, Ralf Jackstell, Matthias Beller, Robert Franke, Dieter Hess, Katrin Marie Dyballa, Dirk Fridag, Frank Geilen
  • Patent number: 10155200
    Abstract: The invention deals with the separation of homogeneous catalysts from reaction mixtures with the help of organophilic nanofiltration. It is based on the object of indicating an option as to how organophilic nanofiltration can be used economically for separating off homogeneous catalysts from reaction mixtures if the separation-active material of the membrane satisfying the separation aim is not available in sufficiently large amounts or only at high cost. This object is achieved by taking into consideration a particular membrane performance indicator during the design and/or the execution of the corresponding membrane separation process.
    Type: Grant
    Filed: February 10, 2016
    Date of Patent: December 18, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Frank Geilen, Robert Franke, Bart Hamers
  • Publication number: 20180319727
    Abstract: The production of 2-propylheptanol described here is effected via Rh-catalyzed hydroformylation of C4-olefin to afford C5-aldehyde, aldol condensation to afford the C10-aldehyde and hydrogenation to afford the C10-alcohol. The emphasis is on the hydroformylation and the ligand employed therein. The problem addressed by the invention is that of reducing the costs of 2PH production. This problem is solved when a cheaper catalyst system which simultaneously achieves a better regioselectivity is employed in the hydroformylation.
    Type: Application
    Filed: August 2, 2016
    Publication date: November 8, 2018
    Applicant: Evonik Degussa GmbH
    Inventors: Katrin Marie DYBALLA, Robert FRANKE, Dirk FRIDAG, Markus SCHWARZ, Hermann-Josef SCHULTE-ALTHOFF, Frank GEILEN
  • Patent number: 10087134
    Abstract: The invention relates to a process comprising the process steps of: a) initially charging an ether having from 3 to 30 carbon atoms; b) adding a phosphine ligand and a compound comprising Pd, or adding a comprising Pd and a phosphine ligand; c) feeding in CO; d) heating the reaction mixture, with conversion of the ether; wherein the phosphine ligand is a compound of formula (I) where m and n are each independently 0 or 1; R1, R2, R3, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl; at least one of the R1, R2, R3, R4 radicals is a —(C3-C20)-heteroaryl radical; and R1, R2, R3, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl or —(C3-C20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-c
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: October 2, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Ralf Jackstell, Helfried Neumann, Matthias Beller, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Frank Geilen, Robert Franke
  • Patent number: 10077228
    Abstract: The invention relates to a compound of formula (I) where R1, R2, R3, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl; at least one of the R1, R2, R3, R4 radicals is a —(C6-C20)-heteroaryl radical having at least six ring atoms; and R1, R2, R3, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl or —(C6-C20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(
    Type: Grant
    Filed: July 19, 2016
    Date of Patent: September 18, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Helfried Neumann, Ralf Jackstell, Matthias Beller, Robert Franke, Dieter Hess, Katrin Marie Dyballa, Dirk Fridag, Frank Geilen
  • Publication number: 20180208538
    Abstract: The invention relates to a process for preparing an ester mixture, in which an n-butene-containing feed mixture having a composition which changes over time is first oligomerized and then converted by hydroformylation, hydrogenation and esterification to an ester mixture. In this process, an approximation of the actual viscosity of the ester mixture is determined. The problem that it addresses is that of specifying a comparatively simple process which enables conversion of an n-butene with a variable composition over time to an ester mixture having a viscosity which can be kept very substantially constant over a long period even when an inconstant C4 source which delivers fluctuating qualities over this period is utilized. This is achieved through controlled use of a second raw material, namely ethene. It has been found that the viscosity of n-butene-based ester mixtures can be influenced by controlled use of ethene in the preparation of the ester precursors.
    Type: Application
    Filed: March 19, 2018
    Publication date: July 26, 2018
    Inventors: Helene Reeker, Guido Stochniol, Dietrich Maschmeyer, Horst-Werner Zanthoff, Jörg Schallenberg, Frank Geilen, Katrin Marie Dyballa, Dirk Fridag, Stephan Peitz, Lena Altmann, Robert Franke
  • Patent number: 10000440
    Abstract: The invention relates to a process for preparing an ester mixture, in which an n-butene-containing feed mixture having a composition which changes over time is first oligomerized and then converted by hydroformylation, hydrogenation and esterification to an ester mixture. In this process, an approximation of the actual viscosity of the ester mixture is determined. The problem that it addresses is that of specifying a comparatively simple process which enables conversion of an n-butene with a variable composition over time to an ester mixture having a viscosity which can be kept very substantially constant over a long period even when an inconstant C4 source which delivers fluctuating qualities over this period is utilized. This is achieved through controlled use of a second raw material, namely ethene. It has been found that the viscosity of n-butene-based ester mixtures can be influenced by controlled use of ethene in the preparation of the ester precursors.
    Type: Grant
    Filed: November 18, 2016
    Date of Patent: June 19, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Helene Reeker, Guido Stochniol, Dietrich Maschmeyer, Horst-Werner Zanthoff, Jörg Schallenberg, Frank Geilen, Katrin Marie Dyballa, Dirk Fridag, Stephan Peitz, Lena Altmann, Robert Franke
  • Patent number: 9981903
    Abstract: The invention relates to a method for preparing di- or tricarboxylic esters by alkoxycarbonylation of dienes having conjugated double bonds. The method includes the steps of initially charging a diene having two conjugated double bonds, adding a phosphine ligand according to formula (I) and a catalyst precursor, adding an alcohol, feeding in CO, and heating the reaction mixture with conversion of the diene to a di- or tricarboxylic ester.
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: May 29, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Ralf Jackstell, Matthias Beller, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Frank Geilen, Robert Franke
  • Publication number: 20180126361
    Abstract: The invention is concerned with catalysts for heterogeneous hydrogenation of oxo process aldehydes. The problem addressed by the invention is that of developing a catalyst containing neither chromium nor nickel. In addition, it is to enable the economically viable hydrogenation of aldehyde mixtures originating from industrial oxo processes on the industrial scale. For this purpose, the catalyst should not be reliant on costly precious metals such as Ru, Pd or Pt. This problem was solved by omitting the chromium and nickel in the preparation of a conventional Cu/Ni/Cr system, such that a catalyst wherein only copper occurs as hydrogenation-active component on the support material thereof, and not chromium or nickel, is obtained. What is surprising here is that a functioning catalyst for the purpose intended still arises at all even though two of three hydrogenation-active metals are omitted.
    Type: Application
    Filed: October 23, 2017
    Publication date: May 10, 2018
    Inventors: Florian Klasovsky, Robert Franke, Frank Geilen, Andreas Jess, Wolfgang Korth, Thomas Quandt, Arne Reinsdorf
  • Patent number: 9963644
    Abstract: The invention relates to a method for cleaning hydrocarbon mixtures, in which a contaminated hydrocarbon mixture comprising hydrocarbons having three to eight carbon atoms is at least partly freed of impurities by contacting with a solid sorbent, wherein the hydrocarbon mixture is exclusively in the liquid state during contact with the sorbent. The object of the invention is to specify a process for cleaning liquid C3 to C8 hydrocarbon mixtures, which is based on a readily available but non-carcinogenic sorbent and which achieves better purities compared to traditional molecular sieves. This object is achieved by using, as sorbents, solid materials of the following composition: copper oxide: 10% to 60% by weight (calculated as CuO); zinc oxide: 10% to 60% by weight (calculated as ZnO); aluminum oxide: 10% to 30% by weight (calculated as Al2O3); other substances: 0% to 5% by weight. Materials of this kind are otherwise used as catalysts in methanol synthesis.
    Type: Grant
    Filed: November 5, 2014
    Date of Patent: May 8, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Frank Geilen, Stephan Peitz, Guido Stochniol, Markus Winterberg, Dietrich Maschmeyer, Armin Rix, Mathias Vogt
  • Patent number: 9938310
    Abstract: Diastereomer mixture comprising diastereomers of the formulae (I.1) and (I.2) where R2, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl; the R1, R3 radicals are each a —(C3-C20)-heteroaryl radical. The invention further relates to Pd complex mixtures comprising the diastereomers according to the invention, and to the use thereof in an alkoxycarbonylation process.
    Type: Grant
    Filed: July 14, 2017
    Date of Patent: April 10, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Helfried Neumann, Ralf Jackstell, Matthias Beller, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Frank Geilen, Robert Franke
  • Patent number: 9914681
    Abstract: The preparation of high-quality oxo process alcohols from inconstant raw material sources is the technically demanding problem which is addressed by a process for continuously preparing an alcohol mixture, in which an input mixture which contains an olefin and has a composition that changes over time is subjected to an oligomerization to obtain an oligomerizate and at least a portion of the olefin oligomers present in the oligomerizate are hydroformylated with carbon monoxide and hydrogen in a hydroformylation in the presence of a homogeneous catalyst system to give aldehydes, at least some of which are converted to the alcohol mixture by subsequent hydrogenation. The process provides a constant plasticizer quality to be produced over a long production period and, optionally, a higher throughput with the same product quality.
    Type: Grant
    Filed: May 20, 2015
    Date of Patent: March 13, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Frank Geilen, Katrin Marie Dyballa, Dieter Hess, Stephan Peitz, Robert Franke, Dirk Fridag, Dietrich Maschmeyer, Helene Reeker, Guido Stochniol
  • Patent number: 9908910
    Abstract: The invention relates to Rh, Ru, Co and Ir complexes comprising bidentate diphosphoramidites as ligands and to the use thereof as catalysts for the hydroformylation of olefins. The invention also relates to a process for preparing an aldehyde from an olefin using the complexes or ligands mentioned.
    Type: Grant
    Filed: December 16, 2016
    Date of Patent: March 6, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Frank Geilen, Galina Morales Torres, Detlef Selent, Armin Börner
  • Patent number: 9896404
    Abstract: The invention relates to Rh, Ru, Co and Ir complexes comprising bidentate diphosphoramidites as ligands and to the use thereof as catalysts for the hydroformylation of olefins. The invention also relates to a process for preparing an aldehyde from an olefin using the complexes or ligands mentioned.
    Type: Grant
    Filed: December 16, 2016
    Date of Patent: February 20, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Frank Geilen, Galina Morales Torres, Detlef Selent, Armin Börner
  • Publication number: 20180022772
    Abstract: Diastereomer mixture comprising diastereomers of the formulae (I.1) and (I.
    Type: Application
    Filed: July 14, 2017
    Publication date: January 25, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu DONG, Helfried NEUMANN, Ralf JACKSTELL, Matthias BELLER, Dirk FRIDAG, Dieter HESS, Katrin Marie DYBALLA, Frank GEILEN, Robert FRANKE
  • Publication number: 20180022773
    Abstract: Compound of formula (I) where R2, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl; the R1, R3 radicals are each a —(C3-C20)-heteroaryl radical; R1, R3 may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen; R2, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl or —(C6-C20)-aryl, may each independently be substituted by one or
    Type: Application
    Filed: July 14, 2017
    Publication date: January 25, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu DONG, Ralf JACKSTELL, Helfried NEUMANN, Matthias BELLER, Dirk FRIDAG, Dieter HESS, Katrin Marie DYBALLA, Frank GEILEN, Robert FRANKE
  • Publication number: 20180022764
    Abstract: The invention relates to a process comprising the following process steps: a) introducing an ethylenically unsaturated compound; b) adding a monophosphine ligand and a compound which comprises Pd, or adding a complex comprising Pd and a monophosphine ligand; c) adding an aliphatic alcohol; d) supplying CO; e) heating the reaction mixture, the ethylenically unsaturated compound being reacted to form an ester; where the monophosphine ligand is a compound of formula (I) where R1 is selected from —(C1-C12)-alkyl, —O—(C1-C12)-alkyl, —O—(C6-C20)-aryl, —(C6-C20)-aryl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C3-C20)-heteroaryl; R2 is selected from —(C6-C20)-aryl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C3-C20)-heteroaryl; R3 is —(C3-C20)-heteroaryl; and R1, R2 and R3 may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalky
    Type: Application
    Filed: July 14, 2017
    Publication date: January 25, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu DONG, Ralph JACKSTELL, Matthias BELLER, Dirk FRIDAG, Dieter HESS, Katrin Marie DYBALLA, Frank GEILEN, Robert FRANKE
  • Publication number: 20180022765
    Abstract: The invention relates to a process comprising the following process steps: a) introducing a first alcohol, the first alcohol having 2 to 30 carbon atoms; b) adding a phosphine ligand and a compound which comprises Pd, or adding a complex comprising Pd and a phosphine ligand; c) adding a second alcohol; d) supplying CO; e) heating the reaction mixture, the first alcohol reacting with CO and the second alcohol to form an ester; where the phosphine ligand is a compound of formula (I) where m and n are each independently 0 or 1; R1, R2, R3, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl; at least one of the R1, R2, R3, R4 radicals is a —(C3-C20)-heteroaryl radical; and R1, R2, R3, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl or —(C3-C20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-c
    Type: Application
    Filed: July 14, 2017
    Publication date: January 25, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu DONG, Ralf JACKSTELL, Helfried NEUMANN, Matthias BELLER, Dirk FRIDAG, Dieter HESS, Katrin Marie DYBALLA, Frank GEILEN, Robert FRANKE
  • Publication number: 20180022684
    Abstract: The invention relates to a process comprising the process steps of: a) initially charging an ether having from 3 to 30 carbon atoms; b) adding a phosphine ligand and a compound comprising Pd, or adding a comprising Pd and a phosphine ligand; c) feeding in CO; d) heating the reaction mixture, with conversion of the ether; wherein the phosphine ligand is a compound of formula (I) where m and n are each independently 0 or 1; R1, R2, R3, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl; at least one of the R1, R2, R3, R4 radicals is a —(C3-C20)-heteroaryl radical; and R1, R2, R3, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl or —(C3-C20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)
    Type: Application
    Filed: July 17, 2017
    Publication date: January 25, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu DONG, Ralf JACKSTELL, Helfried NEUMANN, Matthias BELLER, Dirk FRIDAG, Dieter HESS, Katrin Marie DYBALLA, Frank GEILEN, Robert FRANKE
  • Publication number: 20180022685
    Abstract: The invention relates to a process comprising the following process steps: a) introducing an ether having 3 to 30 carbon atoms; b) adding a phosphine ligand and a compound which comprises Pd, or adding a complex comprising Pd and a phosphine ligand; c) adding an alcohol; d) supplying CO; e) heating the reaction mixture, the ether being reacted for form an ester; where the phosphine ligand is a compound of formula (I) where m and n are each independently 0 or 1; R1, R2, R3, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl; at least one of the R1, R2, R3, R4 radicals is a —(C3-C20)-heteroaryl radical; and R1, R2, R3, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl or —(C3-C20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl,
    Type: Application
    Filed: July 17, 2017
    Publication date: January 25, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu DONG, Ralf JACKSTELL, Helfried NEUMANN, Matthias BELLER, Dirk FRIDAG, Dieter HESS, Katrin Marie DYBALLA, Frank GEILEN, Robert FRANKE