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: 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: 10562833
    Abstract: The present invention relates to a method for preparing saturated Cn- and C2n-alcohols, wherein the ratio of Cn- to C2n-alcohols is controlled by a distillative separation of the aldehydes used.
    Type: Grant
    Filed: November 29, 2018
    Date of Patent: February 18, 2020
    Assignee: Evonik Degussa GmbH
    Inventors: Dirk Fridag, Robert Franke, Michael Grass, Florian Boeck, Corinna Hecht, Benedikt Dercks, Udo Lenz, Christoph Hiller, Christoph Ehlers, Stefan Münzner
  • 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: 10526356
    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: Grant
    Filed: November 7, 2017
    Date of Patent: January 7, 2020
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess
  • Patent number: 10501392
    Abstract: The present invention relates to a method for preparing saturated Cn- and C2n-alcohols, wherein the ratio of Cn- to C2n-alcohols is controlled by the diversion of substreams in individual method steps.
    Type: Grant
    Filed: November 29, 2018
    Date of Patent: December 10, 2019
    Assignee: Evonik Degussa GmbH
    Inventors: Dirk Fridag, Robert Franke, Michael Grass, Florian Boeck, Corinna Hecht, Benedikt Dercks, Udo Lenz, Christoph Hiller, Christoph Ehlers, Stefan Münzner
  • 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
  • Patent number: 10422047
    Abstract: An electrochemical method for C—C coupling a phenol and an aniline in a reaction vessel containing a suitable solvent or solvent mixture and a conductive salt to produce biaryls having both hydroxyl and amino functions, wherein the difference in the oxidation potentials ?E of the substrates ranges from 10 mV to 450 mV and the substrate with the highest oxidation potential is in excess, which method dispenses with multi-step syntheses using metallic reagents.
    Type: Grant
    Filed: February 19, 2014
    Date of Patent: September 24, 2019
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Siegfried R. Waldvogel, Bernd Elsler
  • Publication number: 20190169106
    Abstract: The present invention relates to a method for preparing saturated Cn- and C2n-alcohols, wherein the separation of the Cn-alcohols and the C2n-alcohols is effected by means of at least one two-column system or by means of at least one dividing wall column.
    Type: Application
    Filed: November 29, 2018
    Publication date: June 6, 2019
    Inventors: Dirk Fridag, Robert Franke, Michael Grass, Florian Boeck, Corinna Hecht, Benedikt Dercks, Udo Lenz, Christoph Hiller, Christoph Ehlers, Stefan Münzner
  • Publication number: 20190169105
    Abstract: The present invention relates to a method for preparing saturated Cn- and C2n-alcohols, wherein the ratio of Cn- to C2n-alcohols is controlled by a distillative separation of the aldehydes used.
    Type: Application
    Filed: November 29, 2018
    Publication date: June 6, 2019
    Inventors: Dirk Fridag, Robert Franke, Michael Grass, Florian Boeck, Corinna Hecht, Benedikt Dercks, Udo Lenz, Christoph Hiller, Christoph Ehlers, Stefan Münzner
  • Publication number: 20190169104
    Abstract: The present invention relates to a method for preparing saturated Cn- and C2n-alcohols, wherein the ratio of Cn- to C2n-alcohols is controlled by the diversion of substreams in individual method steps.
    Type: Application
    Filed: November 29, 2018
    Publication date: June 6, 2019
    Inventors: Dirk Fridag, Robert Franke, Michael Grass, Florian Boeck, Corinna Hecht, Benedikt Dercks, Udo Lenz, Christoph Hiller, Christoph Ehlers, Stefan Münzner
  • 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: 10266955
    Abstract: An electrochemical method for coupling anilines. When coupling two different anilines, the difference of the oxidation potential of the substrates is in the region of between 10 mV to 450 mV, and the aniline with the highest oxidation potential is added in excess. The method allows biaryldiamines to be electrochemically produced, and can avoid the need for multi-step syntheses using metallic reagents.
    Type: Grant
    Filed: February 26, 2014
    Date of Patent: April 23, 2019
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Siegfried R. Waldvogel, Bernd Elsler
  • 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: 10214550
    Abstract: Disclosed herein are compounds of formula (I): wherein: the groups R1, R2, R3, R4, R5, R6, R7, R8, R1?, R2?, R3?, R4?, R5?, R6?, R7?, R8?, R1?, R2?, R3?, R4?, R5?, R6?, R7?, R8? are defined herein; and at least one of the following conditions is satisfied: two radicals from at least one of the four following pairs of radicals are not the same radical: R1? and R8?, R2? and R7?, R3? and R6?, R4? and R5?, and two radicals from at least one of the four following pairs of radicals are not the same radical: R1? and R8?, R2? and R7?, R3? and R6?, R4? and R5?.
    Type: Grant
    Filed: June 12, 2017
    Date of Patent: February 26, 2019
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Armin Boerner, Detlef Selent
  • 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: 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
  • 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: 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: 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