Patents by Inventor Robert Franke

Robert Franke 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: 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
  • Patent number: 10196747
    Abstract: Novel 2,2?-diaminobiaryls having two secondary amines and an electrochemical process for preparation thereof.
    Type: Grant
    Filed: July 23, 2015
    Date of Patent: February 5, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Siegfried R. Waldvogel, Bernd Elsler, Mathias Enders
  • Publication number: 20190001316
    Abstract: Markovnikov-selective palladium catalyst for carbonylation of alkynes with heteroarenes.
    Type: Application
    Filed: June 21, 2018
    Publication date: January 3, 2019
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Haoquan LI, Jie LIU, Ralf JACKSTELL, Matthias BELLER, Robert FRANKE
  • Patent number: 10167244
    Abstract: A catalytic method for hydroformylating a cyclooctadiene substrate involving forming a reaction mixture that includes the cyclooctadiene and a precursor of or a transitional metal ligand complex where the ligand has structure (1): H2 and CO are fed into the reaction mixture and the mixture is heated to convert the cyclooctadiene into an aldehyde. A preferred ligand is 2-(anthracen-9-yloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane.
    Type: Grant
    Filed: March 29, 2018
    Date of Patent: January 1, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Detlef Selent, Armin Börner
  • Patent number: 10167245
    Abstract: A catalytic method for hydroformylating cyclooctadiene substrate involving forming a reaction mixture that includes the cyclooctadiene and a precursor of or a transitional metal ligand complex where the ligand has structure (1): (1) H2 and CO are fed into the reaction mixture and the mixture is heated to convert the cyclooctadiene into an aldehyde. A preferred ligand is 4-([1,1?:3?,1?-terphenyl]-2?-yloxy)-S-dinaphtho[2,1-d:1?,2?-f][1,3,2]dioxaphosphepine.
    Type: Grant
    Filed: March 29, 2018
    Date of Patent: January 1, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Detlef Selent, Armin Börner
  • 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
  • Patent number: 10131628
    Abstract: An electrochemical treatment of differently protected aniline or napthylamine results in the preparation of unsymmetrical 2, 2?-diaminebiaryls provided with different protecting groups. The treatment involves the protecting groups prior to the C, C coupling step. The co-reactants generally have different oxidation potentials which results from the selection of the protecting groups. The treatment also enables controlled access to the individual amino functions of the 2, 2?-diaminobiaryls by subsequent selective deprotection.
    Type: Grant
    Filed: July 23, 2015
    Date of Patent: November 20, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Siegfried R. Waldvogel, Bernd Elsler, Mathias Enders
  • Patent number: 10131607
    Abstract: The present invention relates to a process for preparing unsymmetric compounds from the group of the m-terphenyls which can be used as unsymmetric OCO pincer ligands, comprising the process steps of a) reacting a first substituted or unsubstituted phenol with a 1,3-disubstituted arene which may likewise be substituted in the 2 and 5 positions to obtain a phenol-arene coupling product and b) optionally protecting the OH group of the phenol-arene coupling product with a protecting group to obtain a protected phenol-arene coupling product, and c) reacting the phenol-arene coupling product from a) or b) with a second substituted or unsubstituted phenol to obtain an unsymmetric m-terphenyl, with the proviso that the first phenol and the second phenol have different substitution, characterized in that at least one of process steps a) and c) is conducted as an electrochemical process step.
    Type: Grant
    Filed: August 18, 2016
    Date of Patent: November 20, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Siegfried R. Waldvogel, Bernd Elsler, Anton Wiebe, Sebastian Lips
  • Patent number: 10131623
    Abstract: The present invention relates to a process for preparing compounds of the formula ABA by reacting a compound of the formula (A) with a compound of the formula (B) with X=—OR? or —NHR? and R?=H or a protecting group function and R1, R2, R3, R4, R5, R6, R7 and R8 are each independently selected from the group comprising hydrogen, (C1-C12)-alkyl, O—(C1-C12)-alkyl, (C6-C20)-aryl, O—(C6-C20)-aryl, where two of the R1 to R4 radicals may also be joined via a covalent bond, and halogen, which is characterized in that the reaction is conducted electrochemically.
    Type: Grant
    Filed: August 18, 2016
    Date of Patent: November 20, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Siegfried R. Waldvogel, Bernd Elsler, Anton Wiebe
  • Patent number: 10125093
    Abstract: Novel 2,2?-diaminobiaryls having one primary and one secondary amine and an electrochemical process for preparation thereof.
    Type: Grant
    Filed: July 23, 2015
    Date of Patent: November 13, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Siegfried R. Waldvogel, Bernd Elsler, Mathias Enders
  • 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: 10106497
    Abstract: The present invention relates to a method for coupling two arenes with selenium dioxide to give a selenobiaryl ether. The method of the present invention includes: adding a first arene to the reaction mixture, adding a second arene to the reaction mixture, adding selenium dioxide to the reaction mixture, adding an acid having a pKa in the range from 0 to 5 to the reaction mixture, and adjusting the reaction temperature of the reaction mixture such that the first arene and the second arene are converted to a selenobiaryl ether. The present invention also relates to novel selenobiaryl ethers.
    Type: Grant
    Filed: May 18, 2016
    Date of Patent: October 23, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Siegfried R Waldvogel, Thomas Quell, Michael Mirion
  • Patent number: 10100071
    Abstract: Novel heterocyclic selenamonophosphites protected on the hydroxyl group, processes for preparation thereof and the use thereof as ligand.
    Type: Grant
    Filed: December 6, 2016
    Date of Patent: October 16, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Claudia Weilbeer, Detlef Selent, Armin Börner
  • Publication number: 20180290958
    Abstract: Method for hydroformylating cyclooctadiene using 4-([1,1?:3?,1?-terphenyl]-2?-yloxy)-S-dinaphtho[2,1-d:1?,2?-f][1,3,2]dioxaphosphepine.
    Type: Application
    Filed: March 29, 2018
    Publication date: October 11, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie DYBALLA, Robert FRANKE, Dirk FRIDAG, Dieter HESS, Detlef SELENT, Armin BÖRNER
  • Publication number: 20180290957
    Abstract: Process comprising the process steps of: a) initially charging a pentenoic ester, b) adding a ligand of structure 1 or 2: and a compound comprising a metal atom selected from: Rh, Ru, Co, Ir, c) supplying H2 and CO, d) heating the reaction mixture to convert the pentenoic ester to 5-formylpentanoic esters.
    Type: Application
    Filed: March 29, 2018
    Publication date: October 11, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Stephan BEHRENS, Galina Morales TORRES, Armin BÖRNER, Robert FRANKE, Detlef SELENT
  • Publication number: 20180290956
    Abstract: Method for hydroformylating cyclooctadiene using 2-(anthracen-9-yloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane.
    Type: Application
    Filed: March 29, 2018
    Publication date: October 11, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie DYBALLA, Robert FRANKE, Dirk FRIDAG, Dieter HESS, Detlef SELENT, Armin BÖRNER
  • Patent number: 10093604
    Abstract: Novel heterocyclic selenabisphosphites, process for preparation thereof and use thereof as ligand unit for preparing ligands for use in complexes.
    Type: Grant
    Filed: December 6, 2016
    Date of Patent: October 9, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Claudia Weilbeer, Detlef Selent, Armin Börner
  • Patent number: 10093690
    Abstract: Novel heterocyclic selenaphosphites, process for preparation thereof and use thereof as ligand for employment in complexes.
    Type: Grant
    Filed: December 6, 2016
    Date of Patent: October 9, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Claudia Weilbeer, Detlef Selent, Armin Börner
  • 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