Patents by Inventor Holger Wiederhold
Holger Wiederhold 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).
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Publication number: 20230406794Abstract: 1,2-propanediol is prepared by a method involving reacting propene with hydrogen peroxide at 50 to 110° C. in the presence of a catalyst mixture, containing a phase transfer catalyst and a polytungstophosphate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase. The method then involves separating the reaction mixture into an aqueous phase containing 1,2-propanediol and an organic phase; recycling at least part of the separated organic phase to the reaction; and recovering 1,2 propanediol from the aqueous phase. The method further involves reacting a tungstate with hydrogen peroxide and phosphoric acid at 5 to 40° C., in the presence of the phase transfer catalyst, in a liquid mixture containing an aqueous and an organic phase, followed by passing at least a part of the resulting organic phase containing the polytungstophosphate and phase transfer catalyst to the initial reaction.Type: ApplicationFiled: October 7, 2021Publication date: December 21, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz, Patrik Glatz
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Publication number: 20230399279Abstract: A method for preparing 1,2-propanediol involves reacting propene with hydrogen peroxide in the presence of a catalyst mixture, containing a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase. The method then involves separating the reaction mixture into an aqueous phase (Pa) containing 1,2-propanediol and formic acid and an organic phase (Po); recycling at least part of the separated organic phase (Po) to the reaction; contacting at least a part of the separated aqueous phase (Pa) with a palladium catalyst; and recovering 1,2 propanediol from the aqueous phase provided by the contacting. The contacting of at least a part of the separated aqueous phase (Pa) with the palladium catalyst reduces the content of formic acid.Type: ApplicationFiled: October 7, 2021Publication date: December 14, 2023Applicant: Evonik Operations GmbHInventors: Holger WIEDERHOLD, David Bolz, Jürgen Glenneberg
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Publication number: 20230399280Abstract: A method for preparing 1,2-propanediol involves reacting propene with hydrogen peroxide, in the presence of a phase transfer catalyst and a heteropolytungstate, in a liquid two phase reaction mixture with an organic phase containing an alkylaromatic hydrocarbon solvent. The method then involves separating the reaction mixture into an aqueous phase containing 1,2-propanediol and an organic phase, recycling the oxygen depleted organic phase to the reaction, and recovering 1,2 propanediol from the aqueous phase. The reaction and separation are carried out in liquid flooded vessels at a pressure high enough to suppress desorption of gas from the liquid reaction mixture. The separated organic phase is contacted with a stream of a non-flammable gas to desorb from 10 to 75% of the oxygen dissolved in the organic phase into the stream of non-flammable gas, before recycling the organic phase which purges oxygen safely with little loss of propene.Type: ApplicationFiled: October 7, 2021Publication date: December 14, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz, Jürgen Berje
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Publication number: 20230391699Abstract: A method for preparing 1,2-propanediol involves reacting propene with hydrogen peroxide in the presence of a catalyst mixture containing a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase. The process then involves separating the reaction mixture into an aqueous phase (Pa) containing 1,2-propanediol and an organic phase (Po); recycling at least part of the separated organic phase (Po) to the reaction; and recovering 1,2 propanediol from the separated aqueous phase (Pa). In the recovery, 1,2-propanediol is separated from the aqueous phase (Pa) by distillation and the apparent pH of the separated aqueous phase (Pa) is adjusted to at least 9 prior to the distillation to reduce the content of formic acid and acetic acid in the recovered 1,2-propanediol.Type: ApplicationFiled: October 7, 2021Publication date: December 7, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz
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Publication number: 20230382835Abstract: A process for preparing 1,2-propanediol involves dehydrogenating propane to provide a product stream containing propane, propene, and hydrogen; and separating the product stream into a stream containing essentially hydrogen, a stream enriched in propane, and a stream enriched in propene. The process then involves reacting the stream containing essentially hydrogen with oxygen to provide a stream containing hydrogen peroxide; and reacting the stream enriched in propene with the stream containing hydrogen peroxide in the presence of a catalyst mixture, containing a phase transfer catalyst and a heteropolytungstate, in a reaction mixture with two liquid phases. The process further involves separating the reaction mixture of the propene oxidation into an aqueous phase and an organic phase, recycling the organic phase to the propene oxidation, and separating 1,2-propanediol from the aqueous phase.Type: ApplicationFiled: October 7, 2021Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: David Bolz, Holger Wiederhold
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Publication number: 20230382832Abstract: A method for preparing 1,2-propanediol involves reacting propene with hydrogen peroxide in the presence of a catalyst mixture, containing a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase. The method then involves separating the reaction mixture into an aqueous phase (Pa), containing 1,2-propanediol and phosphoric acid esters of 1,2-propanediol, and an organic phase (Po). The method further involves recycling at least part of the separated organic phase (Po) to the reaction; heating at least a part of the separated aqueous phase (Pa) to a temperature of more than 140° C. at a pressure sufficient to maintain at least part of the aqueous phase as a liquid; and recovering 1,2-propanediol from the heated aqueous phase. The heating cleaves phosphoric acid esters of 1,2-propanediol into 1,2-propanediol and phosphoric acid.Type: ApplicationFiled: October 7, 2021Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz
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Publication number: 20230382839Abstract: A method can be used for preparing 1,2-propanediol, dipropylene glycol, and tripropylene glycol. The method involves reacting propene with hydrogen peroxide containing nitrate, in the presence of a catalyst mixture containing a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase. The method then involves separating the reaction mixture into an aqueous phase containing 1,2-propanediol, dipropylene glycol, tripropylene glycol, and nitrate and an organic phase. The method further involves recycling at least part of the separated organic phase to the reaction; hydrogenating the separated aqueous phase using a heterogeneous hydrogenation catalyst to provide a hydrogenated aqueous phase with a reduced nitrate content; and recovering 1,2-propanediol, dipropylene glycol, and tripropylene glycol from the hydrogenated aqueous phase by a sequential multiple-step distillation.Type: ApplicationFiled: October 7, 2021Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz, Jürgen Glenneberg
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Publication number: 20230382833Abstract: A method for preparing 1,2-propanediol and dipropylene glycol involves continuously reacting propene with hydrogen peroxide in the presence of a catalyst mixture, containing a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase, to obtain 1,2-propanediol and dipropylene glycol. The method then involves separating the reaction mixture into an aqueous phase (Pa) containing 1,2-propanediol and dipropylene glycol and an organic phase (Po); recycling at least part of the separated organic phase (Po) to the reaction; and recovering 1,2-propanediol and dipropylene glycol from the separated aqueous phase (Pa), The reaction heat generated is at least partially removed, and the ratio of 1,2 propanediol to dipropylene glycol is controlled by adjusting the weight ratio of hydrogen peroxide to water fed to the reaction.Type: ApplicationFiled: October 7, 2021Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: Holger WIEDERHOLD, David Bolz
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Publication number: 20230382834Abstract: A method for preparing 1,2-propanediol involves continuously reacting propene with hydrogen peroxide in the presence of a catalyst mixture, containing a quaternary ammonium salt and a polytungstophosphate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase containing an alkylaromatic hydrocarbon solvent. The method then involves withdrawing the liquid reaction mixture from the reaction and adding a water-soluble sulfate salt or sulfuric acid to provide a mixture containing from 500 to 10,000 mg/kg of sulfate ions in the aqueous phase. The method further involves separating the mixture obtained into an aqueous phase (Pa) containing 1,2-propanediol and an organic phase (Po), recycling at least a part of the organic phase (Po) to the reaction, and recovering 1,2-propanediol from the aqueous phase (Pa). The method allows for extended operation of the reaction with little loss of tungsten and phase transfer catalyst.Type: ApplicationFiled: October 7, 2021Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz, Patrik Glatz
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Publication number: 20230382878Abstract: An integrated process for making propylene oxide and propylene glycol involves reacting propene with an oxidant to provide propylene oxide, reacting a fraction of the propylene oxide with water to provide an aqueous glycol solution containing monopropylene glycol and dipropylene glycol, and separating monopropylene glycol and dipropylene glycol from the glycol solution by a multi-step distillation. The propylene oxide output can be increased without increasing capacity of the unit for reacting propene to propylene oxide, by reacting propene and hydrogen peroxide in the presence of a catalyst mixture, containing a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture which contains an aqueous phase with a maximum apparent pH of 6 and an organic phase. The reaction mixture is separated into an organic phase, which is recycled to the reaction, and an aqueous phase containing monopropylene glycol and dipropylene glycol, which is passed to replace the glycol solution.Type: ApplicationFiled: October 7, 2021Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz, Bernd Jaeger
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Publication number: 20230382829Abstract: A method for preparing 1,2-propanediol involves reacting propene with hydrogen peroxide, in the presence of a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture containing an aqueous phase with a maximum apparent pH of 6 and an organic phase containing a solvent having a solubility in water at 20° C. of less than 500 mg/kg. The method then involves separating the liquid reaction mixture into an aqueous phase containing 1,2-propanediol and an organic phase; recycling at least a part of the separated organic phase to the reaction; and extracting the separated aqueous phase with an extractant solution containing the same phase transfer catalyst and solvent as used in the reaction to provide an extracted aqueous phase and an extract phase. The method further involves recycling at least a part of the extract phase to the reaction and recovering 1,2-propanediol from the extracted aqueous phase.Type: ApplicationFiled: October 7, 2021Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: Holger Wiederhold, David Bolz, Georg Friedrich Thiele, Bernd Jaeger, Hans-Jürgen Köhle, Sebastian Imm, Marina Lazar
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Publication number: 20220298128Abstract: An integrated process for making styrene and propene oxide which comprises the steps: a) dehydrogenating ethylbenzene in the presence of a dehydrogenation catalyst; b) separating styrene and hydrogen from the reaction mixture of step a); c) producing hydrogen peroxide from hydrogen separated in step b) and oxygen; d) reacting propene with the hydrogen peroxide obtained in step c) in the presence of an epoxidation catalyst to provide a reaction mixture comprising propene oxide; and e) separating propene oxide from the reaction mixture obtained in step d).Type: ApplicationFiled: March 19, 2022Publication date: September 22, 2022Inventors: David BOLZ, Holger WIEDERHOLD
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Publication number: 20220126247Abstract: The present invention relates to a triphasic single reactor comprising a solid, a liquid and a gaseous component, wherein the (i) the solid component is (a) a catalytically active composite based on (b) at least one perforated and permeable support, wherein the catalytically active composite is on at least one side of the support and inside the support and (a) the catalytically active composite is obtained by applying a suspension comprising at least one inorganic component of a compound of at least one of the elements Ce, La Sc, Y, Ti, Zr, Hf, Rf, V, Nb, Ta, Db, Cr, Mo, W, Sg, Mn, Tc, Re, Bh, Fe, Co, B, Al, In, Tl, Si, Ge, Sn, Pb, Sb and Bi with at least one of the elements Te, Se, S, O, Sb, As, P, N, Ge, Si, C and Ga and/or a compound of one of the elements Ti, Zr, Al, Ce and Si with oxygen, and/or a metal selected from Pt, Rh, Ru, Ir, Cu, Ni, Co, Mg, Zn, Al and Pd, in suspension in a sol, and (b) the support comprises fibers of at least one material selected from the group consisting of carbon, metaType: ApplicationFiled: February 6, 2020Publication date: April 28, 2022Inventors: Thomas HAAS, Christian HYING, Matthias PASCALY, Sebastian IMM, Holger WIEDERHOLD
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Patent number: 10597374Abstract: The integrated process comprises a step a) of dehydrogenating propane providing a stream S1 comprising propane and propene; a step b) of separating stream S1 in at least one rectification column, providing an overhead product stream S2 comprising more than 99% by weight propene, a side stream S3 comprising from 90 to 98% by weight propene and a bottoms product stream S4 enriched in propane; a step c) of reacting propene with hydrogen peroxide in the presence of an epoxidation catalyst using propene in molar excess; and a step d) of separating non-reacted propene and propene oxide from the reaction mixture of step c) providing a propene oxide product and a stream S5 comprising propene and propane; wherein stream S3 is passed to step c), stream S5 is recycled to step b) and stream S4 is recycled to step a).Type: GrantFiled: May 11, 2017Date of Patent: March 24, 2020Assignees: Evonik Operations GmbH, thyssenkrupp Industrial Solutions AGInventors: Holger Wiederhold, David Bolz, Georg Friedrich Thiele
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Publication number: 20190276419Abstract: The integrated process comprises a step a) of dehydrogenating propane providing a stream S1 comprising propane and propene; a step b) of separating stream S1 in at least one rectification column, providing an overhead product stream S2 comprising more than 99% by weight propene, a side stream S3 comprising from 90 to 98% by weight propene and a bottoms product stream S4 enriched in propane; a step c) of reacting propene with hydrogen peroxide in the presence of an epoxidation catalyst using propene in molar excess; and a step d) of separating non-reacted propene and propene oxide from the reaction mixture of step c) providing a propene oxide product and a stream S5 comprising propene and propane; wherein stream S3 is passed to step c), stream S5 is recycled to step b) and stream S4 is recycled to step a).Type: ApplicationFiled: May 11, 2017Publication date: September 12, 2019Applicants: EVONIK DEGUSSA GMBH, thyssenkrupp Industrial Solutions AGInventors: Holger WIEDERHOLD, David BOLZ, Georg Friedrich THIELE
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Patent number: 10214471Abstract: The process for preparing 1,2-propanediol from propene and hydrogen peroxide comprises the steps of a) reacting propene with hydrogen peroxide in the presence of a catalyst mixture comprising a phase transfer catalyst and a heteropolytungstate, wherein the reaction is carried out in a liquid mixture comprising an aqueous phase having a pH of at most 6 and an organic phase, b) separating the biphasic mixture from step a) into an aqueous phase and an organic phase comprising propene oxide, c) recycling the propene oxide present in the separated organic phase into the reaction of step a) and d) separating 1,2-propanediol from the aqueous phase separated in step b).Type: GrantFiled: November 1, 2016Date of Patent: February 26, 2019Assignee: Evonik Degussa GmbHInventors: Holger Wiederhold, David Bolz, Bernd Jaeger, Hans-Jürgen Köhle, Sebastian Imm, Georg Friedrich Thiele
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Publication number: 20180354878Abstract: The process for preparing 1,2-propanediol from propene and hydrogen peroxide comprises the steps of a) reacting propene with hydrogen peroxide in the presence of a catalyst mixture comprising a phase transfer catalyst and a heteropolytungstate, wherein the reaction is carried out in a liquid mixture comprising an aqueous phase having a pH of at most 6 and an organic phase, b) separating the biphasic mixture from step a) into an aqueous phase and an organic phase comprising propene oxide, c) recycling the propene oxide present in the separated organic phase into the reaction of step a) and d) separating 1,2-propanediol from the aqueous phase separated in step b).Type: ApplicationFiled: November 1, 2016Publication date: December 13, 2018Applicant: EVONIK DEGUSSA GMBHInventors: Holger Wiederhold, David BOLZ, Bernd JAEGER, Hnas-Jürgen KÖHLE, Sebastian IMM, Georg Friedrich THIELE
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Patent number: 10053440Abstract: An integrated process for making propene oxide and an alkyl tert-butyl ether comprises dehydrogenating a feed stream comprising propane and iso-butane to provide a stream comprising propene, iso-butene and hydrogen; separating this stream into a stream consisting essentially of hydrogen and a stream comprising propene and iso-butene; separating the stream comprising propene and iso-butene into a stream comprising propene and a stream comprising iso-butene; reacting a part or all of the stream comprising iso-butene with an alkanol in the presence of a solid acid catalyst to provide an alkyl tert-butyl ether; and reacting a part or all of the stream comprising propene with hydrogen peroxide in the presence of an epoxidation catalyst to provide propene oxide.Type: GrantFiled: January 8, 2016Date of Patent: August 21, 2018Assignees: EVONIK DEGUSSA GMBH, THYSSENKRUPP INDUSTRIAL SOLUTIONS AGInventors: David Bolz, Holger Wiederhold
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Patent number: 10053438Abstract: An integrated process for making propene oxide and an alkyl tert-butyl ether comprises dehydrogenating a feed stream comprising iso-butane to provide a stream comprising iso-butene and hydrogen and separating this stream into a stream consisting essentially of hydrogen and a stream comprising iso-butene; reacting a part or all of the stream comprising iso-butene with an alkanol in the presence of a solid acid catalyst to provide an alkyl tert-butyl ether; reacting a part or all of the stream consisting essentially of hydrogen with oxygen, providing a stream comprising hydrogen peroxide; and reacting a part or all of the stream comprising hydrogen peroxide with propene in the presence of an epoxidation catalyst to provide propene oxide.Type: GrantFiled: January 8, 2016Date of Patent: August 21, 2018Assignees: EVONIK DEGUSSA GMBH, THYSSENKRUPP INDUSTRIAL SOLUTIONS AGInventors: David Bolz, Holger Wiederhold
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Publication number: 20180002300Abstract: An integrated process for making propene oxide and an alkyl tert-butyl ether comprises dehydrogenating a feed stream comprising propane and iso-butane to provide a stream comprising propene, iso-butene and hydrogen; separating this stream into a stream consisting essentially of hydrogen and a stream comprising propene and iso-butene; separating the stream comprising propene and iso-butene into a stream comprising propene and a stream comprising iso-butene; reacting a part or all of the stream comprising iso-butene with an alkanol in the presence of a solid acid catalyst to provide an alkyl tert-butyl ether; and reacting a part or all of the stream comprising propene with hydrogen peroxide in the presence of an epoxidation catalyst to provide propene oxide.Type: ApplicationFiled: January 8, 2016Publication date: January 4, 2018Applicants: Evonik Degussa GmbH, THYSSENKRUPP INDUSTRIAL SOLUTIONS AGInventors: David BOLZ, Holger WIEDERHOLD