Patents Assigned to Evonik Operations GmbH
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Patent number: 11845849Abstract: A process prepares dialkyl 1,4-cyclohexanedicarboxylates by ring hydrogenation of the corresponding dialkyl terephthalate having a CO value of less than 0.3 mg KOH/g. The dialkyl 1,4-cyclohexanedicarboxylates thus produced can be used as plasticizers or as a component of a plasticizer composition for plastics, in particular PVC.Type: GrantFiled: July 26, 2021Date of Patent: December 19, 2023Assignee: Evonik Operations GmbHInventors: Johannes Kraft, Lena Altmann, Johan Anton, Michael Grass, Thomas Schneider
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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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Patent number: 11840506Abstract: A process for preparing C5 aldehydes involves hydroformylation of butenes with synthesis gas in the presence of a homogeneous catalyst system and a solvent. It is a feature of the process that the aldehyde concentration in the reaction mixture is limited.Type: GrantFiled: May 2, 2023Date of Patent: December 12, 2023Assignee: Evonik Operations GmbHInventors: Dirk Fridag, Johannes Knossalla, Alexander Brächer, Peter Kucmierczyk, Anna Chiara Sale, Robert Franke, Ana Markovic
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Publication number: 20230391720Abstract: D,L-methionine may include, based on the total weight of the D,L-methionine, from 15 to less than 50 wt.-% of the D,L-methionine with a particle size from more than 0 to less 150 micrometers, from 50 to less than 90 wt.-% of the D,L-methionine with a particle size from more than 0 to less 300 micrometers, and from 30 to less than 80 wt.-% of the D,L-methionine with a particle size in the range between 63 and 300 micrometers. The D,L-methionine may have a bulk density of at least 710 kg/m3.Type: ApplicationFiled: October 11, 2021Publication date: December 7, 2023Applicant: Evonik Operations GmbHInventors: Martin KOERFER (Deceased), Hans-Joachim HASSELBACH, Stefan REICHERT, Mauricio ANTEZANA, Antje HANSMEIER
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Publication number: 20230391630Abstract: Precipitated silicas having, a N-cetyl-N,N,N-trimethylammonium bromide (CTAB) surface area ?115 m2/g, a dioctyl adipate (DOA) absorption ?130 ml/(100 g), a RoTap for >300 ?m of ?86%, and a pore volume distribution of V (d5?d50)/V (d5?d100)<0.66. A method of producing the precipitated silicas.Type: ApplicationFiled: October 18, 2021Publication date: December 7, 2023Applicant: Evonik Operations GmbHInventors: André WEHMEIER, Dominik MASCHKE, Agnieszka OCHENDUSZKO
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Publication number: 20230391690Abstract: A process for removing butenes from C4-hydrocarbon streams containing butanes and butenes involves extractive distillation with a suitable solvent. The process also involves heat integration, which allows utilization of the heat of the solvent for heating and/or at least partly evaporating various streams.Type: ApplicationFiled: January 21, 2022Publication date: December 7, 2023Applicant: Evonik Operations GmbHInventors: Philip Lutze, Stephan Peitz, Armin Matthias Rix, Tanita Valèrie Six, Moritz Schröder, Niklas Paul
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Publication number: 20230391689Abstract: A method for separating butenes from C4 hydrocarbon streams containing butanes and butenes involves extractive distillation with a suitable solvent, and a subsequent adiabatic oligomerisation. The method also involves heat integration, which makes it possible to use the heat of the solvent in order to heat and/or at least partly evaporate various streams.Type: ApplicationFiled: January 21, 2022Publication date: December 7, 2023Applicant: Evonik Operations GmbHInventors: Philip Lutze, Stephan Peitz, Armin Matthias Rix, Tanita Valèrie Six, Moritz Schröder, Niklas Paul
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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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Patent number: 11833703Abstract: A process can be used for producing foam panels, for the production of foam films, composed of a polymer having a glass transition temperature Tg of at least 100° C. An average cell diameter of the foam panels measured according to the standard ASTM D 3576 is between 20 ?m and 250 ?m, and less than 20 cells having a diameter >260 ?m are present per m2. The elongation at break of the foam is 4%-13% measured according to ASTM D 638.Type: GrantFiled: October 12, 2021Date of Patent: December 5, 2023Assignee: Evonik Operations GmbHInventors: Felix Goldmann, Thomas Richter, Matthias Alexander Roth, Florian Becker, Jorge Manuel Pinto
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Patent number: 11834399Abstract: A process can be used for preparing aldehydes from C2 to C20 olefins with a subsequent thermal separation for removal of the aldehyde formed. The process involves a membrane separation, which is preceded by performance of a gas exchange by which the proportion of the partial pressure represented by carbon monoxide or hydrogen is increased in order to reduce catalyst losses.Type: GrantFiled: February 6, 2023Date of Patent: December 5, 2023Assignee: Evonik Operations GmbHInventors: Alexander Brächer, Ana Markovic, Anna Chiara Sale, Dirk Fridag, Johannes Knossalla, Peter Kucmierczyk, Robert Franke
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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: 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: 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: 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: 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: 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: 20230383212Abstract: Acrylate-olefin copolymers and a method for the preparation of these copolymers are provided. Lubricant compositions can contain the aforementioned copolymers. The copolymers are useful as a lubricant additive or a synthetic base fluid in a lubricating oil composition, preferably in a gear oil composition, a transmission oil composition, a hydraulic oil composition, an engine oil composition, a marine oil composition, an industrial lubricating oil composition or in grease.Type: ApplicationFiled: May 22, 2023Publication date: November 30, 2023Applicant: Evonik Operations GmbHInventors: Emily Clare SCHWEIßINGER, Stefan Karl Maier, Katja Nothdurft, Yvonne Groß-Onnebrink, Dieter Janßen, Holger Pletsch, Stefan Hilf, Denise Kleinschmidt, Sebastian Babik
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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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Patent number: 11827522Abstract: A method is useful for preparing partially hydrogenated chlorosilanes by selective hydrogenation with a compound of the formula R2AlH, wherein R is a branched or cyclic hydrocarbon. Partially hydrogenated chlorosilanes can be prepared with said method, in particular partially hydrogenated chlorosilanes represented by the formula Cl3SiSi(SiH3)3, (Cl3Si)2Si(SiH3)2 or HSi(SiH3)2SiCl3.Type: GrantFiled: June 7, 2019Date of Patent: November 28, 2023Assignee: Evonik Operations GmbHInventors: Michael Haas, Harald Stüger, Thomas Lainer, Odo Wunnicke, Michael Holthausen