Patents Assigned to Oxea GmbH
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Patent number: 10501396Abstract: 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: GrantFiled: September 5, 2017Date of Patent: December 10, 2019Assignee: OXEA GMBHInventors: Kurt Schalapski, Jan-Henry Rahe, Christoph Balzarek, Gregor Meier, Heinz Strutz
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Patent number: 10450254Abstract: 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: GrantFiled: September 5, 2017Date of Patent: October 22, 2019Assignee: OXEA GMBHInventors: Guido D. Frey, Melanie Bothe, Heinz Strutz, William E. Slinkard
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Patent number: 9896406Abstract: 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: GrantFiled: November 14, 2014Date of Patent: February 20, 2018Assignee: OXEA GMBHInventors: Jens Theuerkauf, Heinz Strutz
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Patent number: 9840454Abstract: 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 produType: GrantFiled: October 9, 2014Date of Patent: December 12, 2017Assignee: OXEA GMBHInventors: Jens Kubitschke, Thorsten Kreickmann, Jörg Arnold, Heinz Strutz
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Patent number: 9745236Abstract: 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 fractiType: GrantFiled: October 24, 2012Date of Patent: August 29, 2017Assignee: OXEA GMBHInventors: Guido D. Frey, Norman Nowotny, Kurt Schalapski, Heinz Strutz
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Patent number: 9714201Abstract: 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: GrantFiled: June 19, 2013Date of Patent: July 25, 2017Assignee: OXEA GMBHInventors: Jens Theuerkauf, Guido D. Frey, Matthias Eisenacher, Kristina Kockrick, Heinz Strutz
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Patent number: 9695100Abstract: 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: GrantFiled: June 26, 2015Date of Patent: July 4, 2017Assignee: OXEA GMBHInventors: Kristina Kockrick, Leif Johnen, Heinz Strutz
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Patent number: 9580573Abstract: 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: GrantFiled: September 28, 2015Date of Patent: February 28, 2017Assignee: OXEA GMBHInventors: Guido D. Frey, Horst Lange, Heinz Strutz, Jacco de Haas
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Patent number: 9580378Abstract: 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: GrantFiled: August 29, 2014Date of Patent: February 28, 2017Assignee: OXEA GMBHInventors: Jens Kubitschke, Thorsten Kreickmann, Jörg Arnold, Matthias Kramer, Heinz Strutz
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Patent number: 9517995Abstract: 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: GrantFiled: November 14, 2014Date of Patent: December 13, 2016Assignee: OXEA GMBHInventors: Jens Theuerkauf, Heinz Strutz
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Patent number: 9517991Abstract: 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: GrantFiled: November 14, 2014Date of Patent: December 13, 2016Assignee: OXEA GMBHInventors: Jens Theuerkauf, Heinz Strutz
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Patent number: 9434672Abstract: 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: GrantFiled: June 18, 2013Date of Patent: September 6, 2016Assignee: OXEA GMBHInventors: Guido D. Frey, Matthias Eisenacher, Kristina Kockrick, Heinz Strutz
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Patent number: 9388115Abstract: 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: GrantFiled: January 28, 2016Date of Patent: July 12, 2016Assignee: OXEA GMBHInventors: Guido D. Frey, Tonia Weber, Jörg Arnold, Thorsten Kreickmann, Heinz Strutz
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Patent number: 9353032Abstract: 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: GrantFiled: September 28, 2013Date of Patent: May 31, 2016Assignee: OXEA GMBHInventors: Matthias Eisenacher, Kurt Schalapski, Heinz Strutz
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Patent number: 9334225Abstract: 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: GrantFiled: June 19, 2013Date of Patent: May 10, 2016Assignee: OXEA GMBHInventors: Leif Johnen, Guido D. Frey, Matthias Eisenacher, Kristina Kockrick, Heinz Strutz
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Patent number: 9315694Abstract: 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: GrantFiled: September 12, 2011Date of Patent: April 19, 2016Assignee: OXEA GMBHInventors: Antonietta Schiro, Tito Zanetta, Christoph Balzarek, Olivier Borgmeier, Guido Frey, Leif Johnen, Donald Raff, Heinz Strutz
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Patent number: 9284253Abstract: 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: GrantFiled: August 10, 2013Date of Patent: March 15, 2016Assignee: OXEA GMBHInventors: Guido D. Frey, Tonia Weber, Jörg Arnold, Thorsten Kreickmann, Heinz Strutz
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Publication number: 20150344400Abstract: 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: ApplicationFiled: August 10, 2013Publication date: December 3, 2015Applicant: OXEA GmbHInventors: Guido D. FREY, Tonia WEBER, Jörg ARNOLD, Thorsten KREICKMANN, Heinz STRUTZ
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Patent number: 9193844Abstract: 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: GrantFiled: June 5, 2013Date of Patent: November 24, 2015Assignee: OXEA GMBHInventors: Guido D. Frey, Horst Lange, Heinz Strutz, Jacco de Haas
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Patent number: 9174922Abstract: The present invention relates to a continuous, catalytic process for preparing a vinyl ester of the formula R—C(O)O—CH?CH2 by reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O—CH?CH2, wherein the reaction is effected at a temperature of 90 to 160° C. and at a pressure of 0.5 to 15 MPa without withdrawal of a reactant in the presence of a transition metal catalyst containing at least one transition metal from the group of ruthenium, osmium, rhodium, iridium, palladium and platinum, and then the resulting reaction mixture is separated into its constituents.Type: GrantFiled: January 18, 2013Date of Patent: November 3, 2015Assignee: OXEA GMBHInventors: Leif Johnen, Heinz Strutz, Kurt Schalapski, Norman Nowotny, Wolfgang Höfs, Sebastian Geisel