Patents by Inventor Dirk Fridag

Dirk Fridag 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: 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: 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
  • 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
  • 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
  • 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: 10017443
    Abstract: The invention relates to a method for producing alcohols by homogeneously catalyzed hydroformylation of olefins to aldehydes and subsequent hydration of the aldehydes. The invention further relates to a system for carrying out the method. The main focus is on the separation technique for work-up of the hydroformylation mixture. The problem addressed by the invention is that specifying a work-up method for hydroformylation mixtures that utilizes the specific advantages of known separation technologies but at the same time largely avoids the specific disadvantages of said separation technologies. The most important objective is to create a catalyst separation system that is as complete and at the same time conservative as possible and that operates in a technically reliable manner and entails low investment and operating costs. The method should be unrestrictedly suitable for processing the reaction output from oxo systems in “world scale” format.
    Type: Grant
    Filed: February 13, 2014
    Date of Patent: July 10, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Hans-Gerd Lueken, Bart Hamers, Dirk Fridag, Robert Franke, Markus Priske, Dieter Hess, Marc Becker, Markus Rudek
  • 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
  • Patent number: 9982001
    Abstract: Bisphosphites having an unsymmetric central biaryl unit.
    Type: Grant
    Filed: December 3, 2015
    Date of Patent: May 29, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Armin Börner, Detlef Selent
  • Publication number: 20180127444
    Abstract: The invention relates to bisphosphites having 2,4-tert-butylphenyl units and a method for the preparation thereof. Furthermore, the invention relates to the use of the compounds as ligands in a ligand-metal complex. The compound, and also the complex, may be used as a catalytically active composition in hydroformylation reactions.
    Type: Application
    Filed: November 7, 2017
    Publication date: May 10, 2018
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie DYBALLA, Robert FRANKE, Dirk FRIDAG, Dieter HESS
  • Patent number: 9950979
    Abstract: A process for preparing unsymmetric biphenols, comprising: a) adding a first substituted phenol to the reaction mixture; b) adding a second substituted phenol having different substitution than the first phenol to the reaction mixture; c) adding selenium dioxide to the reaction mixture; d) adding a solvent; and e) heating the reaction mixture such that the first substituted phenol and the second phenol having different substitution are converted to an unsymmetric biphenol.
    Type: Grant
    Filed: May 20, 2015
    Date of Patent: April 24, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Michael Mirion, Thomas Quell, Siegfried R. Waldvogel
  • 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
  • Patent number: 9879353
    Abstract: Electrochemical process for coupling two phenols of different oxidation potential, and novel biphenols which can be prepared by this electrochemical coupling.
    Type: Grant
    Filed: December 10, 2013
    Date of Patent: January 30, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Siegfried R. Waldvogel, Bernd Elsler