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: 11820739
    Abstract: A process for preparing aldehydes by a homogeneously catalysed hydroformylation of C4 to C20 olefins involves withdrawing a biphasic stream (liquid/gaseous) and expanding in two stages. Before, between, or after the two stages, the liquid phase is cooled. Only after expansion and cooling is the homogeneously dissolved rhodium catalyst system separated from the residual stream.
    Type: Grant
    Filed: November 15, 2022
    Date of Patent: November 21, 2023
    Assignee: Evonik Operations GmbH
    Inventors: Ana Markovic, Frank Geilen, Alexander Brächer, Benedikt Dercks, Stefan Drees, Tonia Weber, Robert Franke, Dirk Fridag
  • Patent number: 11806669
    Abstract: The invention provides an improvement in terms of control and process technology for a method of continuous removal of a component from a liquid mixture using a membrane unit comprising at least one membrane stage. The improvement is that a portion of the overall permeate stream is recycled to the feed vessel and/or beyond the feed vessel but upstream of the conveying device, and the remainder of the overall permeate stream is removed, with the recycled permeate having a higher concentration of the component to be separated off than the removed permeate. The presently disclosed method can especially be used for separation of a homogeneously dissolved catalyst from a liquid reaction mixture.
    Type: Grant
    Filed: December 13, 2021
    Date of Patent: November 7, 2023
    Assignee: Evonik Operations GmbH
    Inventors: Frederik Gluth, Marc Schäpertöns, Thomas Quell, Frank Geilen, Stefan Drees, Fabian Höckelmann, Robert Franke
  • Publication number: 20230348356
    Abstract: The invention relates to compounds 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 —(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)-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)-heteroar
    Type: Application
    Filed: July 7, 2023
    Publication date: November 2, 2023
    Applicant: EVONIK OPERATIONS GMBH
    Inventors: Kaiwu DONG, Xiangjie FANG, Helfried NEUMANN, Ralf JACKSTELL, Matthias BELLER, Robert FRANKE, Dieter HESS, Katrin Marie DYBALLA, Dirk Fridag, Frank GEILEN
  • Patent number: 11773041
    Abstract: A process for preparing aldehydes by a homogeneously catalyzed hydroformylation of C4 to C20 olefins involves withdrawing a biphasic stream (liquid/gaseous) and expanding in two stages. Before, between, or after the two stages, the liquid phase is cooled. Only after expansion and cooling is the homogeneously dissolved rhodium catalyst system separated from the residual stream in a three-stage removal.
    Type: Grant
    Filed: November 16, 2022
    Date of Patent: October 3, 2023
    Assignee: Evonik Operations GmbH
    Inventors: Frank Geilen, Alexander Brächer, Stefan Drees, Benedikt Dereks, Robert Franke, Ana Markovic, Armin Matthias Rix, Martin Oldemeyer, Dirk Fridag
  • Publication number: 20230159425
    Abstract: A process for preparing aldehydes by a homogeneously catalyzed hydroformylation of C4 to C20 olefins involves withdrawing a biphasic stream (liquid/gaseous) and expanding in two stages. Before, between, or after the two stages, the liquid phase is cooled. Only after expansion and cooling is the homogeneously dissolved rhodium catalyst system separated from the residual stream in a three-stage removal.
    Type: Application
    Filed: November 16, 2022
    Publication date: May 25, 2023
    Applicant: Evonik Operations GmbH
    Inventors: Frank Geilen, Alexander Brächer, Stefan Drees, Benedikt Dercks, Robert Franke, Ana Markovic, Armin Matthias Rix, Martin Oldemeyer, Dirk Fridag
  • Publication number: 20230159423
    Abstract: A process for preparing aldehydes by a homogeneously catalysed hydroformylation of C4 to C20 olefins involves withdrawing a biphasic stream (liquid/gaseous) and expanding in two stages. Before, between, or after the two stages, the liquid phase is cooled. Only after expansion and cooling is the homogeneously dissolved rhodium catalyst system separated from the residual stream.
    Type: Application
    Filed: November 15, 2022
    Publication date: May 25, 2023
    Applicant: Evonik Operations GmbH
    Inventors: Ana MARKOVIC, Frank Geilen, Alexander Brächer, Benedikt Dercks, Stefan Drees, Tonia Weber, Robert Franke, Dirk Fridag
  • Publication number: 20220193611
    Abstract: The invention provides an improvement in terms of control and process technology for a method of continuous removal of a component from a liquid mixture using a membrane unit comprising at least one membrane stage. The improvement is that a portion of the overall permeate stream is recycled to the feed vessel and/or beyond the feed vessel but upstream of the conveying device, and the remainder of the overall permeate stream is removed, with the recycled permeate having a higher concentration of the component to be separated off than the removed permeate. The presently disclosed method can especially be used for separation of a homogeneously dissolved catalyst from a liquid reaction mixture.
    Type: Application
    Filed: December 13, 2021
    Publication date: June 23, 2022
    Applicant: Evonik Operations GmbH
    Inventors: Frederik Gluth, Marc Schäpertöns, Thomas Quell, Frank Geilen, Stefan Drees, Fabian Höckelmann, Robert Franke
  • Patent number: 11174207
    Abstract: A process is useful for the isomerization of C4 to C9 olefins having an internal double bond into the corresponding olefins having a terminal double bond using a heterogeneous catalyst system of a silicon-aluminium mixed oxide composition.
    Type: Grant
    Filed: November 11, 2020
    Date of Patent: November 16, 2021
    Assignee: Evonik Operations GmbH
    Inventors: Frank Geilen, Felix Gärtner, Horst-Werner Zanthoff, Guido Stochniol
  • Publication number: 20210276939
    Abstract: The invention relates to compounds 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 —(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)-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)-hetero
    Type: Application
    Filed: May 21, 2021
    Publication date: September 9, 2021
    Applicant: EVONIK OPERATIONS GMBH
    Inventors: Kaiwu DONG, Xiangjie FANG, Helfried NEUMANN, Ralf JACKSTELL, Matthias BELLER, Robert FRANKE, Dieter HESS, Katrin Marie DYBALLA, Dirk FRIDAG, Frank GEILEN
  • Patent number: 11028110
    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: Grant
    Filed: July 14, 2017
    Date of Patent: June 8, 2021
    Assignee: EVONIK OPERATIONS GMBH
    Inventors: Kaiwu Dong, Ralf Jackstell, Helfried Neumann, Matthias Beller, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Frank Geilen, Robert Franke
  • Publication number: 20210147320
    Abstract: A process is useful for the isomerization of C4 to C9 olefins having an internal double bond into the corresponding olefins having a terminal double bond using a heterogeneous catalyst system of a silicon-aluminium mixed oxide composition.
    Type: Application
    Filed: November 11, 2020
    Publication date: May 20, 2021
    Applicant: Evonik Operations GmbH
    Inventors: Frank Geilen, Felix Gärtner, Horst-Werner Zanthoff, Guido Stochniol
  • Patent number: 10589249
    Abstract: A heat exchanger system can be used for removal or introduction of heat from or into a chemical reactor in which a chemical reaction is proceeding. The system further provides an apparatus for controlling the temperature of a reactor and a process for performing a chemical reaction, in each case using a heat exchanger system with a thermally insulated inner tube.
    Type: Grant
    Filed: April 18, 2019
    Date of Patent: March 17, 2020
    Assignee: Evonik Operations GmbH
    Inventors: Jan Willaert, Martina Ludwig, Frank Geilen, Johannes Knossalla, Thomas Quell, Robert Franke
  • Patent number: 10562838
    Abstract: Process comprising the following process steps: a) introducing an ethylenically unsaturated compound; b) adding a ligand-metal complex comprising Pd and a bidentate phosphine ligand, or adding a bidentate phosphine ligand and a compound which comprises Pd; c) adding an alcohol; d) supplying CO; e) heating the reaction mixture, the ethylenically unsaturated compound being reacted to form an ester, where the reaction mixture is admixed with less than 0.1 mol %, based on the amount of substance of the ethylenically unsaturated compound, of Brønsted acids having an acid strength of pKa?3, characterized in that the phosphine ligand is substituted on at least one phosphorus atom by at least one heteroaryl radical.
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: February 18, 2020
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Xianjie Fang, Kaiwu Dong, Helfried Neumann, Ralf Jackstell, Matthias Beller, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Frank Geilen, Robert Franke
  • Patent number: 10544174
    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)-cyclo
    Type: Grant
    Filed: July 14, 2017
    Date of Patent: January 28, 2020
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Ralph Jackstell, Matthias Beller, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Frank Geilen, Robert Franke
  • Patent number: 10494326
    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, —O—(C
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: December 3, 2019
    Assignee: 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: 20190329212
    Abstract: A heat exchanger system can be used for removal or introduction of heat from or into a chemical reactor in which a chemical reaction is proceeding. The system further provides an apparatus for controlling the temperature of a reactor and a process for performing a chemical reaction, in each case using a heat exchanger system with a thermally insulated inner tube.
    Type: Application
    Filed: April 18, 2019
    Publication date: October 31, 2019
    Applicant: Evonik Degussa GmbH
    Inventors: Jan WILLAERT, Martina Ludwig, Frank Geilen, Johannes Knossalla, Thomas Quell, Robert Franke
  • Patent number: 10294191
    Abstract: The invention relates to compounds of formula (I) where R1 is selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl; R2 is selected from —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(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)-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, —COO—(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.
    Type: Grant
    Filed: July 19, 2016
    Date of Patent: May 21, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Ralf Jackstell, Matthias Beller, Robert Franke, Dieter Hess, Katrin Marie Dyballa, Dirk Fridag, Frank Geilen
  • Patent number: 10245578
    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: Grant
    Filed: October 23, 2017
    Date of Patent: April 2, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Florian Klasovsky, Robert Franke, Frank Geilen, Andreas Jess, Wolfgang Korth, Thomas Quandt, Arne Reinsdorf
  • Patent number: 10227278
    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: Grant
    Filed: August 2, 2016
    Date of Patent: March 12, 2019
    Assignee: EVONIK DEGUSSA GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Markus Schwarz, Hermann-Josef Schulte-Althoff, Frank Geilen
  • Patent number: 10202409
    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: Grant
    Filed: July 14, 2017
    Date of Patent: February 12, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Ralf Jackstell, Helfried Neumann, Matthias Beller, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Frank Geilen, Robert Franke