Patents Assigned to Oxea GmbH
  • Patent number: 12637407
    Abstract: The present invention relates to a process for the preparation of mixed polyol-carboxylic acid esters having a molecular weight of greater than or equal to 200 g/mol and less than or equal to 1000 g/mol, wherein a polyol is reacted in an at least two-step reaction with different monocarboxylic acids in the form of monocarboxylic acids or of monocarboxylic acid anhydrides, wherein the different monocarboxylic acids are reacted with the polyol in the order of their reactivity in the esterification reaction, starting with the lowest reactivity, wherein the monocarboxylic acids with the lower reactivity are reacted at least partly as monocarboxylic acid anhydride and the monocarboxylic acid with the highest reactivity is reacted thereafter as monocarboxylic acid with the polyol. Furthermore, the present invention relates to the use of the process for the preparation of mixed polyol esters.
    Type: Grant
    Filed: January 27, 2022
    Date of Patent: May 26, 2026
    Assignee: OXEA GmbH
    Inventors: Christoph Balzarek, Eduard Rais, Jens Kubitschke, Roswitha Stein, Julia Zimmerer, Alessa Hinzmann
  • Patent number: 12606512
    Abstract: The present invention relates to a process for the preparation of aldehydes by hydroformylation of olefins by means of synthesis gas over a transition metal complex catalyst, wherein within a first process step the olefins are reacted by means of a water-soluble transition metal complex catalyst consisting of a metal and ligands bound thereto in the presence of a water-miscible solvent, the pressure, temperature and proportions of the solvent and aqueous catalyst solution being controlled so that the hydroformylation is carried out in a homogeneous single-phase reaction solution and within a second process step, by lowering the temperature and/or reducing the pressure, the homogeneous reaction solution obtained from the first reaction step is converted into a two-phase process solution and at least part of the organic phase is separated from the aqueous phase.
    Type: Grant
    Filed: November 30, 2021
    Date of Patent: April 21, 2026
    Assignee: OXEA GmbH
    Inventors: Dennis Vogelsang, Lars Hüttermann, Tim Wilmsen
  • Patent number: 12503418
    Abstract: The present invention relates to a process for the preparation of polycyclic aliphatic dialdehydes by hydroformylation of polycyclic aliphatic diolefins in the presence of synthesis gas over an organophosphorus ligand modified metal catalyst system having a transition metal of the 8th-10th subgroup, wherein the hydroformylation is carried out by means of a water-soluble diphosphine or triarylphosphine complex catalyst at a pressure of greater than or equal to 0.5 MPa and less than or equal to 10 MPa and at a temperature of greater than or equal to 70° C. and less than or equal to 150° ° C. in a homogeneous liquid reaction phase, the homogeneous liquid phase comprising at least one non-aqueous solvent, diolefin and/or mono- and/or dialdehydes thereof as reaction products and an aqueous catalyst solution, the proportions of these components in the solution being controlled so as to obtain a single-phase solution under the reaction conditions.
    Type: Grant
    Filed: November 30, 2021
    Date of Patent: December 23, 2025
    Assignee: OXEA GmbH
    Inventor: Dennis Vogelsang
  • Patent number: 10501396
    Abstract: The present invention relates to the continuous production of 2-methylene alkanals in a tube reactor, wherein in the 2-position non-branched alkanals are reacted with formaldehyde under acid-base catalysis in the presence of secondary amines and carboxylic acids under laminar flow conditions.
    Type: Grant
    Filed: September 5, 2017
    Date of Patent: December 10, 2019
    Assignee: OXEA GMBH
    Inventors: Kurt Schalapski, Jan-Henry Rahe, Christoph Balzarek, Gregor Meier, Heinz Strutz
  • Patent number: 10450254
    Abstract: The present invention relates to a process for simultaneously consecutive preparation of polyols by base-catalyzed reaction of at least two different mid-chain aldehydes with formaldehyde. The simultaneous consecutive mode of operation makes it possible to achieve high conversions and high selectivities for both aldehydes, with additional achievement of a distinct reduction in the amount of unreacted formaldehyde remaining. This leads to improved process economics, since the energy costs for workup of the formaldehyde stream are distinctly reduced.
    Type: Grant
    Filed: September 5, 2017
    Date of Patent: October 22, 2019
    Assignee: OXEA GMBH
    Inventors: Guido D. Frey, Melanie Bothe, Heinz Strutz, William E. Slinkard
  • Patent number: 9896406
    Abstract: A process for preparing 2-methylbutyric acid having a reduced content of 3-methylbutyric acid from the secondary streams obtained in the preparation of pentanoic acids, includes generating a stream enriched with 2-methylbutanal and 3-methyl-butanal. The stream enriched with 2-methylbutanal and 3-methylbutanal of step is reacted with formaldehyde. The reaction with formaldehyde is followed by removal of the organic phase and selective hydrogenation in the presence of a hydrogenation catalyst with hydrogen at elevated temperature and elevated pressure and, after removal of the hydrogenation catalyst, treatment of the hydrogenation output obtained with an oxidizing agent.
    Type: Grant
    Filed: November 14, 2014
    Date of Patent: February 20, 2018
    Assignee: OXEA GMBH
    Inventors: Jens Theuerkauf, Heinz Strutz
  • Patent number: 9840454
    Abstract: A process for obtaining product streams enriched with polyol esters from the secondary streams from polyol ester preparation, comprising a) the reaction of polyols of the general formula (II) H—(—O—[—CR1R2—]m—)o—OH??(II) in which R1 and R2 are each independently hydrogen, an alkyl radical having 1 to 5 carbon atoms or a hydroxyalkyl radical having 1 to 5 carbon atoms, m is an integer from 1 to 10, o is an integer from 2 to 15, with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atom, with removal of the water formed; b) the removal of unconverted starting compounds from the crude ester formed; c) the treatment of the crude ester obtained in step b) with steam to form a volatile secondary stream; and d) the removal of the volatile secondary stream obtained in step c), characterized in that the volatile secondary stream obtained in step d) is separated into an aqueous phase and an organic phase and the organic phase removed is subjected to a further treatment with steam and a produ
    Type: Grant
    Filed: October 9, 2014
    Date of Patent: December 12, 2017
    Assignee: OXEA GMBH
    Inventors: Jens Kubitschke, Thorsten Kreickmann, Jörg Arnold, Heinz Strutz
  • Patent number: 9745236
    Abstract: Distillative process for obtaining ditrimethylolpropane from solutions includes separating ditrimethylolpropane from the solution in a first distillation unit into a first tops fraction comprising low-boiling compounds having a lower boiling point than ditrimethylolpropane and a first bottoms fraction; introducing the first bottoms fraction into a second distillation unit having at least 5 theoretical plates, said unit being configured as a thin-film evaporator with a column attachment and drawing off a second tops fraction comprising intermediate-boiling compounds having a lower boiling point than ditrimethylolpropane as well as withdrawing a second bottoms fraction from the second distillation unit and introducing the second bottoms fraction into a third distillation unit having at least 4 theoretical plates, said unit being configured as a thin-film evaporator with a column attachment, such that ditrimethylolpropane is obtained as a third tops fraction and high boilers are removed as a third bottoms fracti
    Type: Grant
    Filed: October 24, 2012
    Date of Patent: August 29, 2017
    Assignee: OXEA GMBH
    Inventors: Guido D. Frey, Norman Nowotny, Kurt Schalapski, Heinz Strutz
  • Patent number: 9714201
    Abstract: Process for preparing isononylamines starting out from 2-ethylhexanol, characterized in that (a) 2-ethylhexanol is dehydrated in the presence of a catalyst to form octene; (b) the octene obtained in step a) is reacted with carbon monoxide and hydrogen in the presence of a transition metal compound of group VIII of the Periodic Table of the Elements to form isononanal; and (c) the isononanal obtained in step b) is converted into isononylamines.
    Type: Grant
    Filed: June 19, 2013
    Date of Patent: July 25, 2017
    Assignee: OXEA GMBH
    Inventors: Jens Theuerkauf, Guido D. Frey, Matthias Eisenacher, Kristina Kockrick, Heinz Strutz
  • Patent number: 9695100
    Abstract: A process for producing a mixture comprising tertiary isononanoic acids proceeding from 2-ethylhexanol is characterized in that 2-ethylhexanol is (a) reacted at a temperature of 0° C. to 40° C. with a mixture of concentrated formic acid and a concentrated Brønsted acid, wherein 2 to 10 mol of formic acid are used per mole of 2-ethylhexanol and the concentrated Brønsted acid is used in an amount that corresponds to 6 to 90 mol of protons per mole of 2-ethylhexanol. The resulting reaction mixture from step (a) is subsequently (b) brought into contact with water, and the mixture comprising tertiary isononanoic acids formed according to step b) is removed.
    Type: Grant
    Filed: June 26, 2015
    Date of Patent: July 4, 2017
    Assignee: OXEA GMBH
    Inventors: Kristina Kockrick, Leif Johnen, Heinz Strutz
  • Patent number: 9580573
    Abstract: A mixture useful as plasticizer comprises trimellitic esters and polyether polyol esters, characterized in that the mixture comprises from 1 to 99% by weight of trimellitic esters and 99 to 1% by weight of polyether polyol esters, wherein the polyether polyol esters can be derived from linear or branched, aliphatic monocarboxylic acids having 3 to 20 carbon atoms in the molecule.
    Type: Grant
    Filed: September 28, 2015
    Date of Patent: February 28, 2017
    Assignee: OXEA GMBH
    Inventors: Guido D. Frey, Horst Lange, Heinz Strutz, Jacco de Haas
  • Patent number: 9580378
    Abstract: A batchwise process for aftertreatment of polyol esters prepared by reacting polyols of the general formula (II) H—(—O—[—CR1R2—]m—)o—OH??(II) in which R1 and R2 are each independently hydrogen, an alkyl radical having 1 to 5 carbon atoms, preferably methyl, ethyl or propyl, or a hydroxyalkyl radical having 1 to 5 carbon atoms, preferably the hydroxymethyl radical, m is an integer from 1 to 10, preferably 1 to 8 and especially 1, 2, 3 or 4, o is an integer from 2 to 15, preferably 2 to 8 and especially 2, 3, 4 or 5, with excess linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms and having a lower boiling point than the polyols used.
    Type: Grant
    Filed: August 29, 2014
    Date of Patent: February 28, 2017
    Assignee: OXEA GMBH
    Inventors: Jens Kubitschke, Thorsten Kreickmann, Jörg Arnold, Matthias Kramer, Heinz Strutz
  • Patent number: 9517995
    Abstract: A process for preparing isomeric hexanoic acids comprising 2-methylpentanoic acid from the secondary streams obtained in the preparation of pentanals, characterized in that a) a mixture comprising linear butenes is reacted to give a pentanal mixture; b) the mixture obtained in step a) is separated into a stream enriched with 2-methylbutanal and 3-methyl-butanal, and a stream enriched with n-pentanal; c) the stream enriched with 2-methylbutanal and 3-methylbutanal of step b) is reacted with formaldehyde; d) the reaction mixture obtained after step c) is selectively reacted to give a mixture comprising 2-methylbutanal and isomeric hexanals; e) the reaction mixture is separated into a stream enriched with 2-methylbutanal and a stream enriched with a mixture of isomeric hexanals; and f) the mixture of isomeric hexanals obtained in step e) is oxidized to a mixture of isomeric hexanoic acids comprising 2-methylpentanoic acid.
    Type: Grant
    Filed: November 14, 2014
    Date of Patent: December 13, 2016
    Assignee: OXEA GMBH
    Inventors: Jens Theuerkauf, Heinz Strutz
  • Patent number: 9517991
    Abstract: A process for preparing 2-methylbutanal from the secondary streams obtained in the preparation of mixtures of isomeric ?,?-unsaturated decenals, characterized in that a) a mixture comprising linear butenes is reacted in the presence of transition metal compounds of group VIII of the Periodic Table of the Elements with carbon monoxide and hydrogen at elevated temperature and elevated pressure to give a pentanal mixture; b) the pentanal mixture obtained in step a) is converted in the presence of basic compounds to a mixture of isomeric ?,?-unsaturated decenals; and c) the mixture obtained in step b) is separated into a stream enriched with unconverted 2-methylbutanal and a stream enriched with a mixture of isomeric ?,?-unsaturated decenals; with the proviso that the stream which has been separated off in step c) and is enriched with unconverted 2-methylbutanal is reacted with formaldehyde.
    Type: Grant
    Filed: November 14, 2014
    Date of Patent: December 13, 2016
    Assignee: OXEA GMBH
    Inventors: Jens Theuerkauf, Heinz Strutz
  • Patent number: 9434672
    Abstract: Process for preparing isononanoic acid proceeding from 2-ethylhexanol, characterized in that (a) 2-ethylhexanol is dehydrated to octene in the presence of a catalyst; (b) the octene obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give isononanal; and (c) the isononanal obtained in step b) is oxidized to isononanoic acid.
    Type: Grant
    Filed: June 18, 2013
    Date of Patent: September 6, 2016
    Assignee: OXEA GMBH
    Inventors: Guido D. Frey, Matthias Eisenacher, Kristina Kockrick, Heinz Strutz
  • Patent number: 9388115
    Abstract: A process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms, is characterized in that a mixture of the starting compounds is allowed to react in the presence of a Lewis acid containing at least one element of groups 4 to 14 of the periodic table of the elements as a catalyst and in the presence of an adsorbent with removal of the water formed, and then the crude ester obtained is aftertreated by adding a further adsorbent which is an acidic activated carbon having a pH of 1 to 6.5.
    Type: Grant
    Filed: January 28, 2016
    Date of Patent: July 12, 2016
    Assignee: OXEA GMBH
    Inventors: Guido D. Frey, Tonia Weber, Jörg Arnold, Thorsten Kreickmann, Heinz Strutz
  • Patent number: 9353032
    Abstract: A method for preparing neopentyl glycol by addition of isobutyraldehyde and formaldehyde in the presence of a tertiary alkylamine as catalyst to give hydroxypivalaldehyde with subsequent hydrogenation at a temperature of 80 to 140° C. and at a pressure of 2 to 18 MPa in the liquid phase, is characterized in that the hydrogenation is carried out in the presence of a copper chromite catalyst comprising the activators barium and manganese.
    Type: Grant
    Filed: September 28, 2013
    Date of Patent: May 31, 2016
    Assignee: OXEA GMBH
    Inventors: Matthias Eisenacher, Kurt Schalapski, Heinz Strutz
  • Patent number: 9334225
    Abstract: Process for preparing the vinyl ester of isononanoic acid starting out from 2-ethylhexanol, characterized in that (a) 2-ethylhexanol is dehydrated in the presence of a catalyst to form octene; (b) the octene obtained in step a) is converted into an isononanoic acid having one more carbon atom; and (c) the isononanoic acid obtained in step b) is converted into the corresponding vinyl ester.
    Type: Grant
    Filed: June 19, 2013
    Date of Patent: May 10, 2016
    Assignee: OXEA GMBH
    Inventors: Leif Johnen, Guido D. Frey, Matthias Eisenacher, Kristina Kockrick, Heinz Strutz
  • Patent number: 9315694
    Abstract: The present invention relates to a copolymer composition comprising 5-95 pphwm of vinyl acetate and 95-5 pphwm of vinyl 3,5,5-trimethylhexanoate, wherein the corresponding 3,5,5-trimethylhexanoic acid has a content of the 3,5,5-trimethylhexanoic acid isomer of at least 88% by weight. Said copolymer is composed and synthesized so as to be useful in the formulation of binders for fibrous substrates such as woven or nonwoven products, paints, adhesives for porous or non-porous substrates, construction cementitious compositions, redispersible powders.
    Type: Grant
    Filed: September 12, 2011
    Date of Patent: April 19, 2016
    Assignee: OXEA GMBH
    Inventors: Antonietta Schiro, Tito Zanetta, Christoph Balzarek, Olivier Borgmeier, Guido Frey, Leif Johnen, Donald Raff, Heinz Strutz
  • Patent number: 9284253
    Abstract: A process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms, is characterized in that a mixture of the starting compounds is allowed to react in the presence of a Lewis acid containing at least one element of groups 4 to 14 of the periodic table of the elements as a catalyst and in the presence of an adsorbent with removal of the water formed, and then the crude ester obtained is aftertreated by adding a further adsorbent which is an acidic activated carbon having a pH of 1 to 6.5.
    Type: Grant
    Filed: August 10, 2013
    Date of Patent: March 15, 2016
    Assignee: OXEA GMBH
    Inventors: Guido D. Frey, Tonia Weber, Jörg Arnold, Thorsten Kreickmann, Heinz Strutz