Patents by Inventor Markus Dugal

Markus Dugal 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: 10807084
    Abstract: The present invention relates to silica-based heterogeneous zinc compounds which are suitable as catalysts in the reaction of amines with dialkyl carbonates to produce carbamates. The catalysts have the formula [SiO2]—CH2—CHR—X—COOZn[Y], wherein [SiO2] represents a silica carrier selected from the group consisting of ordered mesoporous silica and irregular amorphous narrow pore silica, R represents a moiety selected from the group consisting of hydrogen, —CH3, and —CH2CH3, preferably hydrogen, X is an aliphatic chain of 2 to 11 carbon atoms that optionally comprises ether moieties and [Y] represents a mono anion. The invention is also directed towards a method for the preparation of the aforementioned compounds and towards method for the alkoxycarbonylation of amines.
    Type: Grant
    Filed: May 14, 2018
    Date of Patent: October 20, 2020
    Assignee: Covestro Deutschland AG
    Inventors: Stefan Wershofen, Markus Dugal, Gernot Jaeger, Anton Vidal Ferran, Jose Luis Nuñez Rico
  • Patent number: 10703713
    Abstract: The industrial scale preparation of isocyanates gives rise to distillation bottom streams that are in need of further workup. These distillation bottom streams still also contain, as well as a distillation residue consisting of compounds that can be evaporated without decomposition only with great difficulty if at all (also referred to as residue for short), proportions of the desired target product (i.e. isocyanate to be prepared). The present invention relates to a process that enables recovery, in an efficient manner, of this proportion of isocyanate to be prepared in a distillation bottom stream which is obtained in the workup of the crude liquid process product which contains the isocyanate to be prepared and is formed in an isocyanate preparation process. More particularly, the present invention relates to a drying step in which the isocyanate to be prepared is recovered to form a solid material that has been largely to completely freed of this isocyanate.
    Type: Grant
    Filed: December 18, 2017
    Date of Patent: July 7, 2020
    Assignee: Covestro Deutschland AG
    Inventors: Tim Loddenkemper, Jurgen Arras, Markus Dugal
  • Publication number: 20200147594
    Abstract: The present invention relates to silica-based heterogeneous zinc compounds which are suitable as catalysts in the reaction of amines with dialkyl carbonates to produce carbamates. The catalysts have the formula [SiO2]—CH2—CHR—X—COOZn[Y], wherein [SiO2] represents a silica carrier selected from the group consisting of ordered mesoporous silica and irregular amorphous narrow pore silica, R represents a moiety selected from the group consisting of hydrogen, —CH3, and —CH2CH3, preferably hydrogen, X is an aliphatic chain of 2 to 11 carbon atoms that optionally comprises ether moieties and [Y] represents a mono anion. The invention is also directed towards a method for the preparation of the aforementioned compounds and towards method for the alkoxycarbonylation of amines.
    Type: Application
    Filed: May 14, 2018
    Publication date: May 14, 2020
    Inventors: Stefan Wershofen, Markus Dugal, Gernot Jaeger, Anton Vidal Ferran, Jose Luis Nuñez Rico
  • Publication number: 20200095194
    Abstract: The industrial scale preparation of isocyanates gives rise to distillation bottom streams that are in need of further workup. These distillation bottom streams still also contain, as well as a distillation residue consisting of compounds that can be evaporated without decomposition only with great difficulty if at all (also referred to as residue for short), proportions of the desired target product (i.e. isocyanate to be prepared). The present invention relates to a process that enables recovery, in an efficient manner, of this proportion of isocyanate to be prepared in a distillation bottom stream which is obtained in the workup of the crude liquid process product which contains the isocyanate to be prepared and is formed in an isocyanate preparation process. More particularly, the present invention relates to a drying step in which the isocyanate to be prepared is recovered to form a solid material that has been largely to completely freed of this isocyanate.
    Type: Application
    Filed: December 18, 2017
    Publication date: March 26, 2020
    Inventors: Tim LODDENKEMPER, Jurgen ARRAS, Markus DUGAL
  • Publication number: 20100266481
    Abstract: Processes for the production of chlorine from a gas containing hydrogen chloride and carbon monoxide, which comprise the catalysed oxidation of the carbon monoxide as well as optionally further oxidizable constituents, with oxygen to form carbon dioxide in an upstream reactor under adiabatic conditions.
    Type: Application
    Filed: May 23, 2007
    Publication date: October 21, 2010
    Applicant: Bayer Material Science AG
    Inventors: Michel Haas, Markus Dugal, Knud Werner
  • Patent number: 7692042
    Abstract: Crude aniline is produced by hydrogenating nitrobenzene in the presence of a catalyst. This crude aniline is then purified by means of a single-step or multi-step distillation process in which aqueous alkali metal hydroxide solution is added to the crude aniline prior to distillation and/or during distillation of the crude aniline.
    Type: Grant
    Filed: February 15, 2007
    Date of Patent: April 6, 2010
    Assignee: Bayer MaterialScience AG
    Inventors: Markus Dugal, Franz-Ulrich Von Gehlen, Stefan Wershofen, Andre Lago, Peter Lehner, Benie Marotz
  • Patent number: 7488850
    Abstract: Compounds containing phenolic hydroxy groups are removed from a gas stream which contains at least one aromatic amine generated during the gas-phase hydrogenation reaction of the corresponding nitroaromatic compounds with hydrogen, by adsorption on a basic solid.
    Type: Grant
    Filed: November 6, 2007
    Date of Patent: February 10, 2009
    Assignee: Bayer MaterialScience LLC
    Inventors: Knut Sommer, Markus Dugal, Ido Schwarz, Stefan Wershofen, Peter Lehner, Stephan Schubert, Alexandra Groβe Böwing
  • Patent number: 7456303
    Abstract: The present invention provides a catalyst containing titanium in bonded form, non-crystalline silicon dioxide and at least one crystalline silicate phase which has a zeolite structure, wherein the non-crystalline silicon dioxide is applied to at least one of the crystalline silicate phases which have a zeolite structure and wherein at least one of the crystalline silicate phases which have a zeolite structure contains silicon-carbon bonds with which non-hydrolytically separable organic groups R are bonded to silicon. Furthermore, the present invention provides a process for preparing this catalyst and a process for producing an epoxide from a compound which contains a carbon-carbon double bond (preferably from propene) comprising reacting the compound which contains a carbon-carbon double bond with hydrogen peroxide in the presence of the catalyst according to the invention.
    Type: Grant
    Filed: August 13, 2007
    Date of Patent: November 25, 2008
    Assignee: Bayer MaterialScience AG
    Inventors: Markus Weisbeck, Marie-Therese Heinen, Jorg Schmitt, Gerhard Wegener, Markus Dugal
  • Patent number: 7435853
    Abstract: Di- and polyamines of the diphenylmethane series are produced by a) converting nitrobenzene and methanol in the presence of a catalyst to aniline, formaldehyde and carbon monoxide, and then b) converting the aniline and formaldehyde produced in step a) in the presence of an acid catalyst to di- and polyamines of the diphenylmethane series, and c) converting the carbon monoxide produced in step a) with chlorine to phosgene.
    Type: Grant
    Filed: February 9, 2006
    Date of Patent: October 14, 2008
    Assignee: Bayer MaterialScience AG
    Inventors: Stefan Grabowski, Markus Dugal, Aurel Wolf
  • Publication number: 20080139850
    Abstract: Compounds containing phenolic hydroxy groups are removed from a gas stream which contains at least one aromatic amine generated during the gas-phase hydrogenation reaction of the corresponding nitroaromatic compounds with hydrogen, by adsorption on a basic solid.
    Type: Application
    Filed: November 6, 2007
    Publication date: June 12, 2008
    Inventors: Knut Sommer, Markus Dugal, Ido Schwarz, Stefan Wershofen, Peter Lehner, Stephan Schubert, Alexandra Grosse-Bowing
  • Publication number: 20080015371
    Abstract: The present invention provides a catalyst containing titanium in bonded form, non-crystalline silicon dioxide and at least one crystalline silicate phase which has a zeolite structure, wherein the non-crystalline silicon dioxide is applied to at least one of the crystalline silicate phases which have a zeolite structure and wherein at least one of the crystalline silicate phases which have a zeolite structure contains silicon-carbon bonds with which non-hydrolytically separable organic groups R are bonded to silicon. Furthermore, the present invention provides a process for preparing this catalyst and a process for producing an epoxide from a compound which contains a carbon-carbon double bond (preferably from propene) comprising reacting the compound which contains a carbon-carbon double bond with hydrogen peroxide in the presence of the catalyst according to the invention.
    Type: Application
    Filed: August 13, 2007
    Publication date: January 17, 2008
    Inventors: Markus Weisbeck, Marie-Therese Heinen, Jorg Schmitt, Gerhard Wegener, Markus Dugal
  • Publication number: 20070265466
    Abstract: A process for the coupled production of chlorine and isocyanates in which the sulfuric acid used for both processes is combined after use, concentrated together and returned to one or both processes.
    Type: Application
    Filed: May 10, 2007
    Publication date: November 15, 2007
    Inventors: Markus Dugal, Bernd Pennemann, Friedhelm Kamper
  • Publication number: 20070238901
    Abstract: Crude aniline is produced by hydrogenating nitrobenzene in the presence of a catalyst. The crude aniline is then extracted with aqueous alkali metal hydroxide solution under conditions such that the aqueous phase is the lower phase during separation of the aqueous and organic phases.
    Type: Application
    Filed: February 15, 2007
    Publication date: October 11, 2007
    Inventors: Markus Dugal, Franz-Ulrich Von Gehlen, Stefan Wershofen, Andre Lago, Peter Lehner, Werner Backer, Benie Marotz, Horst Brinkschulte
  • Patent number: 7271116
    Abstract: The present invention provides a catalyst containing titanium in bonded form, non-crystalline silicon dioxide and at least one crystalline silicate phase which has a zeolite structure, wherein the non-crystalline silicon dioxide is applied to at least one of the crystalline silicate phases which have a zeolite structure and wherein at least one of the crystalline silicate phases which have a zeolite structure contains silicon-carbon bonds with which non-hydrolytically separable organic groups R are bonded to silicon. Furthermore, the present invention provides a process for preparing this catalyst and a process for producing an epoxide from a compound which contains a carbon-carbon double bond (preferably from propene) comprising reacting the compound which contains a carbon-carbon double bond with hydrogen peroxide in the presence of the catalyst according to the invention.
    Type: Grant
    Filed: May 11, 2004
    Date of Patent: September 18, 2007
    Assignee: Bayer MaterialScience AG
    Inventors: Markus Weisbeck, Marie-Therese Heinen, Jörg Schmitt, Gerhard Wegener, Markus Dugal
  • Publication number: 20070203364
    Abstract: Crude aniline is produced by hydrogenating nitrobenzene in the presence of a catalyst. This crude aniline is then purified by means of a single-step or multi-step distillation process in which aqueous alkali metal hydroxide solution is added to the crude aniline prior to distillation and/or during distillation of the crude aniline.
    Type: Application
    Filed: February 15, 2007
    Publication date: August 30, 2007
    Inventors: Markus Dugal, Franz-Ulrich Von Gehlen, Stefan Wershofen, Andre Lago, Peter Lehner, Benie Marotz
  • Publication number: 20060183938
    Abstract: Di- and polyamines of the diphenylmethane series are produced by a) converting nitrobenzene and methanol in the presence of a catalyst to aniline, formaldehyde and carbon monoxide, and then b) converting the aniline and formaldehyde produced in step a) in the presence of an acid catalyst to di- and polyamines of the diphenylmethane series, and c) converting the carbon monoxide produced in step a) with chlorine to phosgene.
    Type: Application
    Filed: February 9, 2006
    Publication date: August 17, 2006
    Inventors: Stefan Grabowski, Markus Dugal, Aurel Wolf
  • Publication number: 20050113557
    Abstract: Diamines and polyamines of the diphenylmethane series are produced by a) converting nitrobenzene and methanol simultaneously to aniline and formaldehyde in the presence of a catalyst, and b) converting the aniline and formaldehyde prepared in step a) to diamines and polyamines of the diphenylmethane series in the presence of an acidic catalyst. The diamines and polyamines produced by this process are particularly useful for the production of diisocyanates and polyisocyanates of the diphenylmethane series.
    Type: Application
    Filed: October 7, 2004
    Publication date: May 26, 2005
    Inventor: Markus Dugal
  • Publication number: 20040229747
    Abstract: The present invention provides a catalyst containing titanium in bonded form, non-crystalline silicon dioxide and at least one crystalline silicate phase which has a zeolite structure, wherein the non-crystalline silicon dioxide is applied to at least one of the crystalline silicate phases which have a zeolite structure and wherein at least one of the crystalline silicate phases which have a zeolite structure contains silicon-carbon bonds with which non-hydrolytically separable organic groups R are bonded to silicon. Furthermore, the present invention provides a process for preparing this catalyst and a process for producing an epoxide from a compound which contains a carbon-carbon double bond (preferably from propene) comprising reacting the compound which contains a carbon-carbon double bond with hydrogen peroxide in the presence of the catalyst according to the invention.
    Type: Application
    Filed: May 11, 2004
    Publication date: November 18, 2004
    Inventors: Markus Weisbeck, Marie-Therese Heinen, Jorg Schmitt, Gerhard Wegener, Markus Dugal
  • Publication number: 20040230083
    Abstract: The present invention provides hydro-oxidation catalysts for the oxidation of hydrocarbons, containing an organic-inorganic hybrid material as well as gold particles and/or silver particles, a process for the production thereof, and the use thereof as a catalyst.
    Type: Application
    Filed: January 6, 2004
    Publication date: November 18, 2004
    Inventors: Markus Weisbeck, Marie-Therese Heinen, Jorg Schmitt, Gerhard Wegener, Markus Dugal
  • Patent number: 6770765
    Abstract: The present invention provides hydro-oxidation catalysts for the oxidation of hydrocarbons, containing an organic-inorganic hybrid material as well as gold particles and/or silver particles, a process for the production thereof, and the use thereof as a catalyst.
    Type: Grant
    Filed: January 10, 2003
    Date of Patent: August 3, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Markus Weisbeck, Marie-Therese Heinen, Jörg Schmitt, Gerhard Wegener, Markus Dugal