Hydrogen Peroxide Utilized Patents (Class 549/531)
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Patent number: 11873285Abstract: A process for making propene oxide involves reacting propene with hydrogen peroxide in the presence of methanol, a titanium zeolite epoxidation catalyst, and nitrogen containing compounds present in an amount of from 100 to 3000 mg/kg of hydrogen peroxide. Non-reacted propene is separated from the reaction mixture; the propene depleted reaction mixture is continuously distilled in a distillation column providing an overhead product stream containing propene oxide and methanol and a bottoms product stream; and propene oxide is separated from the overhead product stream. An acid is added to the propane depleted reaction mixture and/or to the distillation column at the same level or above the feed point for the propene depleted reaction mixture and/or contacted to the feed to the distillation column to provide an apparent pH in the bottoms product stream of from 3 to 4.5, which reduces the nitrogen content of the separated propene oxide.Type: GrantFiled: October 12, 2022Date of Patent: January 16, 2024Assignees: Evonik Operations GmbH, thyssenkrupp Uhde GmbHInventors: Maik Bernhard, Juliette Halli, Marc Brendel, Sören Götz, Hans-Christian Dietz
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Patent number: 11654426Abstract: The method for manufacturing a modified aluminosilicate includes a first step of treating an aluminosilicate with an acid, a second step of primarily calcining the treated material obtained in the first step at 550° C. to 850° C., and a third step of contacting the calcined material obtained in the second step with a liquid containing one or more Group 4 elements and/or Group 5 elements, and then drying and secondarily calcining the resultant. The modified aluminosilicate includes one or more Group 4 elements and/or Group 5 elements, and exhibits an absorbance at 300 nm in an ultraviolet visible spectrum of 1.0 or higher. The method for manufacturing aromatic dihydroxy compounds includes reacting a phenol with hydrogen peroxide in the presence of a specific modified aluminosilicate.Type: GrantFiled: May 20, 2019Date of Patent: May 23, 2023Assignee: MITSUI CHEMICALS, INC.Inventors: Yoshiya Matsukawa, Nobuhiko Horiuchi, Akihiro Okabe, Yoshihiro Kubota, Satoshi Inagaki
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Patent number: 11485717Abstract: The invention provides a method for producing an epoxy compound by hydrogen peroxide using an organic compound having a carbon-carbon double bond as a raw material, wherein a by-product is suppressed from being generated and the epoxy compound is produced in a high yield. In particular, the invention provides a method for producing an epoxy compound involving oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide in the presence of a catalyst, wherein the catalyst comprises a tungsten compound; a phosphoric acid, a phosphonic acid or salts thereof; and an onium salt having an alkyl sulfate ion represented by formula (I) as an anion: wherein R1 is a linear or branched aliphatic hydrocarbon group having 1 to 18 carbons, which may be substituted with 1 to 3 phenyl groups.Type: GrantFiled: August 19, 2019Date of Patent: November 1, 2022Assignee: ENEOS CORPORATIONInventors: Shohei Takata, Kenta Ue, Takeshi Koike, Atsushi Kameyama
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Patent number: 10994270Abstract: The present invention relates to a method for the reactivation of homogeneous catalyst systems from organic reaction mixtures. The catalyst systems are suitable for the oxidation of organic compounds such as, for example, cyclododecene. The reactivation is carried out using an aqueous base.Type: GrantFiled: June 28, 2017Date of Patent: May 4, 2021Assignee: Evonik Operations GmbHInventors: Ralf Meier, Stephanie Bajus, Jens Döring
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Patent number: 10870631Abstract: In a process for the epoxidation of propene, comprising continuously reacting a propene feed with hydrogen peroxide in the presence of an epoxidation catalyst in a reaction step, using propene in excess to hydrogen peroxide, to provide a liquid reaction mixture comprising non-reacted propene, extra safety measures caused by the presence of oxygen during work-up of the liquid reaction mixture of the epoxidation reaction can be avoided by stripping liquid reaction mixture from step a) with an inert gas to provide an oxygen depleted stripped liquid reaction mixture and a strip gas stream, selecting the amount of inert gas to provide an oxygen concentration in the strip gas stream in the range of from 0.1 to 10% by weight, separating non-reacted propene from the strip gas stream and recycling it to the reaction step, and separating propene oxide from the stripped liquid reaction mixture.Type: GrantFiled: May 16, 2018Date of Patent: December 22, 2020Assignees: EVONIK OPERATIONS GMBH, THYSSENKRUPP INDUSTRIAL SOLUTIONS AGInventors: Willi Hofen, Thomas Haas, Wolfgang Wöll, Jürgen Schemel, Hans-Christian Dietz, Marc Brendel
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Patent number: 10807868Abstract: Catalysts, catalytic systems and related synthetic methods for in situ production of H2O2 and use thereof in reaction with oxidizable substrates.Type: GrantFiled: November 12, 2019Date of Patent: October 20, 2020Assignee: Northwestern UniversityInventors: Kimberly A. Gray, Justin M. Notestein, Todd R. Eaton
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Patent number: 10774057Abstract: A process for preparing ethene oxide comprising providing a liquid feed stream comprising ethene, hydrogen peroxide, and a solvent; passing the liquid feed stream into an epoxidation zone comprising a catalyst comprising a titanium zeolite comprising zinc and having framework type MWW, and subjecting the liquid feed stream to epoxidation reaction conditions in the epoxidation zone, obtaining a reaction mixture comprising ethene oxide, water, and the solvent; removing an effluent stream from the epoxidation zone, the effluent stream comprising ethene oxide, water and the solvent.Type: GrantFiled: July 12, 2017Date of Patent: September 15, 2020Assignee: BASF SEInventors: Andrei-Nicolae Parvulescu, Ulrich Mueller, Joaquim Henrique Teles, Dominic Riedel, Markus Weber, Yan Li
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Patent number: 10766871Abstract: A continuous process for the preparation of propylene oxide, comprising providing a liquid feed stream comprising propene, hydrogen peroxide, methanol, water, at least one dissolved potassium salt of hydroxyethylidenediphosphonic acid, and optionally propane; passing the liquid feed stream provided in (i) into an epoxidation reactor comprising a catalyst comprising a titanium zeolite of structure type MFI, and subjecting the liquid feed stream to epoxidation reaction conditions in the epoxidation reactor, obtaining a reaction mixture comprising propylene oxide, methanol, water, and the at least one dissolved potassium salt of hydroxyethylidenediphosphonic acid, and optionally propane; removing an effluent stream from the epoxidation reactor, the effluent stream comprising propylene oxide, methanol, water, at least a portion of the at least one potassium salt of hydroxyethylidenediphosphonic acid, and optionally propane.Type: GrantFiled: December 16, 2016Date of Patent: September 8, 2020Assignees: BASF SE, Dow Global Technologies LLCInventors: Edward O. Madenjian, Kenric A. Marshall
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Patent number: 10676450Abstract: In a process for the epoxidation of an olefin with hydrogen peroxide in the presence of a solvent, where a mixture comprising olefin, an aqueous hydrogen peroxide solution and a solvent is continuously passed through a fixed bed of an epoxidation catalyst comprising a titanium zeolite, addition of a chelating agent to the aqueous hydrogen peroxide solution before mixing it with solvent reduces or prevents formation of deposits on the catalyst and blocking of orifices of a liquid distributor.Type: GrantFiled: January 6, 2017Date of Patent: June 9, 2020Assignees: EVONIK OPERATIONS GMBH, THYSSENKRUPP INDUSTRIAL SOLUTIONS AGInventors: Franz Schmidt, Nico Dauth, Matthias Pascaly
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Patent number: 10661503Abstract: In a three-dimensional (3D) printing method example, build material granules are applied. Each of the build material granules includes a plurality of primary ceramic particles agglomerated together by a binder that is at least partially soluble in a primary solvent of a fusing agent. Pressure is applied to crush the build material granules. The fusing agent is selectively applied on at least a portion of the build material granules or the crushed build material granules to pattern the portion, and to introduce a latent binder to the portion. The application of the build material granules, the application of the pressure, and the selectively application of the fusing agent are repeated to create a green body. The latent binder is activated by heating the green body in order to produce a cured green body.Type: GrantFiled: April 13, 2016Date of Patent: May 26, 2020Assignee: Hewlett-Packard Development Company, L.P.Inventors: Michael G. Monroe, Vladek Kasperchik, David Michael Ingle
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Patent number: 10544116Abstract: Disclosed herein is a process for purifying propylene oxide, including the steps of: (i) providing a stream S0 containing propylene oxide, acetonitrile, water, and an organic compound containing a carbonyl group —C(?O)—; and (ii) separating propylene oxide from the stream S0 by subjecting the stream S0 to distillation conditions in a distillation column to obtain a gaseous top stream S1c which is enriched in propylene oxide compared to the stream S0, a liquid bottoms stream S1a which is enriched in acetonitrile and water compared to the stream S0, and a side stream S1b containing propylene oxide which is enriched in the carbonyl compound compared to the stream S0.Type: GrantFiled: July 19, 2017Date of Patent: January 28, 2020Assignee: BASF SEInventors: Joaquim Henrique Teles, Marvin Kramp, Christian Mueller, Nicolai Tonio Woerz, Bernd Metzen, Tobias Keller, Dominic Riedel, Markus Weber, Daniel Urbanczyk, Andrei-Nicolae Parvulescu, Ulrike Wegerle, Ulrich Mueller
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Patent number: 10544115Abstract: A continuous process for the preparation of propylene oxide, comprising a start-up stage and normal run stage, wherein the normal run stage comprises (i) continuously providing a liquid feed stream comprising propene, hydrogen peroxide, acetonitrile, a formate salt, water and optionally propane, wherein in the liquid feed stream, the molar amount of the formate salt relative to the molar amount of hydrogen peroxide at a given point of time during the normal run stage is aN(Fo/H2O2); (ii) continuously passing the liquid feed stream provided in (i) into an epoxidation zone comprising a catalyst comprising a titanium zeolite having framework type MWW, and subjecting the liquid feed stream to epoxidation reaction conditions in the epoxidation zone, obtaining a reaction mixture comprising propylene oxide, acetonitrile, water, the formate salt, optionally propene, and optionally propane; (iii) continuously removing an effluent stream from the epoxidation zone, the effluent stream comprising propylene oxide, acetoniType: GrantFiled: February 16, 2017Date of Patent: January 28, 2020Assignee: BASF SEInventors: Dominic Riedel, Joaquim Henrique Teles, Heiner Schelling, Ulrike Wegerle, Ulrich Mueller, Andrei-Nicolae Parvulescu, Jochen Mannweiler, Timo Henn, Thomas Luederitz, Nicolai Tonio Woerz, Christian Mueller, Markus Weber, Daniel Urbanczyk
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Patent number: 10399952Abstract: During start-up of a continuous epoxidation of propene with hydrogen peroxide in a methanol solvent with a shaped titanium silicalite catalyst in a tube bundle reactor with a cooling jacket, cooling medium is fed at the rate for full load of the reactor with a constant entry temperature of from 20° C. to 50° C., methanol solvent is fed at a rate of from 50 to 100% for full load of the reactor, hydrogen peroxide is fed at a rate that starts with no more than 10% of the rate for full load and is increased continuously or stepwise to maintain a maximum temperature in the fixed bed of no more than 60° C. and a difference between the maximum temperature in the fixed bed and the cooling medium entry temperature of no more than 20° C., and propene is fed at a rate of from 20 to 100% of the rate for full load, increasing the feeding rate when the molar ratio of propene to hydrogen peroxide reaches the molar ratio for full load.Type: GrantFiled: March 10, 2017Date of Patent: September 3, 2019Assignees: Evonik Degussa GmbH, thyssenkrupp Industrial Solutions AGInventors: Wolfgang Wöll, Marc Brendel, Bernd Jaeger, Niels Bredemeyer, Bärbel Kolbe, Norbert Ullrich, Maik Bernhard
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Patent number: 10316007Abstract: A continuous process for preparing propylene oxide proceeds by (a) reacting propene with hydrogen peroxide in a reaction apparatus in the presence acetonitrile as solvent, obtaining a stream S0 containing propylene oxide, acetonitrile, water, at least one further component B; (b) separating propylene oxide from S0, obtaining stream S1 containing acetonitrile, water and B; (c) dividing S1 into streams S2 and S3; (d) subjects S3 to vapor-liquid fractionation in a first fractionation unit, obtaining vapor fraction stream S4a being depleted, relative to S3, of at least one of B and obtaining liquid bottoms stream S4b, and subjecting at least part of vapor fraction stream S4a to vapor-liquid fractionation in a second fractionation unit, obtaining vapor fraction stream S4c and liquid bottoms stream S4 being depleted, relative to S4a, of at least one of B; (e) recycling at least a portion of S4 to (a).Type: GrantFiled: October 27, 2015Date of Patent: June 11, 2019Assignees: BASF SE, DOW GLOBAL TECHNOLOGIES LLCInventors: Joaquim Henrique Teles, Dominic Riedel, Bianca Seelig, Philip Kampe, Markus Weber, Alexander Schroeder, Andrei-Nicolae Parvulescu, Ulrich Mueller, Daniel Urbanczyk, Meinolf Weidenbach, Werner J. Witzl, Holger Baer
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Patent number: 10160737Abstract: A polyvalent glycidyl compound is produced from a compound having one or more 2-alkenyl ether groups and two or more 2-alkenyl groups using a hydrogen peroxide aqueous solution as an oxidizing agent to oxidize the 2-alkenyl ether groups and the 2-alkenyl groups. A 2-alkenyl ether compound having two or more (un)substituted 2-alkenyl groups and one or more (un)substituted 2-alkenyl ether groups is oxidized using a hydrogen peroxide aqueous solution as an oxidizing agent in the presence of a tungsten compound and a quaternary ammonium salt as catalysts and of phosphoric acid as a co-catalyst, while controlling the pH of the reaction solution to 1.0-4.0 using an acid other than phosphoric acid. During the oxidation, the step of adding the hydrogen peroxide aqueous solution to the reaction solution and the step of adding the acid other than phosphoric acid thereto are alternately repeated at intervals two or more times.Type: GrantFiled: October 28, 2015Date of Patent: December 25, 2018Assignee: SHOWA DENKO K.K.Inventors: Chika Yamashita, Yoshitaka Ishibashi
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Patent number: 10125108Abstract: In a process for the epoxidation of propene, comprising the steps: reacting propene with hydrogen peroxide in the presence of a titanium silicalite catalyst and a methanol solvent; separating non-reacted propene and propene oxide from the resulting reaction mixture to provide a solvent mixture comprising methanol and water in a combined amount of at least 90% by weight; and feeding this solvent mixture as a feed stream to a continuously operated methanol distillation column at a feed point in the middle section of said column to provide an overhead product comprising at least 90% by weight methanol and a bottoms product comprising at least 90% by weight water; the addition of a liquid defoamer, having a solubility in the feed stream of less than 10 mg/kg at 25° C. and a surface tension at the liquid air interface of less than 22 mN/m at 20° C.Type: GrantFiled: April 19, 2016Date of Patent: November 13, 2018Assignees: EVONIK DEGUSSA GMBH, THYSSENKRUPP INDUSTRIAL SOLUTIONSInventors: Robert Jahn, Wolfgang Wöll, Bernd Jaeger, Matthias Pascaly
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Patent number: 10093636Abstract: Synthesizing bio-plasticizers with acidic ionic liquids as catalysts. The acidic ionic liquids are Bronsted acidic ionic liquids, which are composed of alkyl sulfone pyridinium and strong Bronsted acid. Epoxidized fatty acid alkyl esters could be obtained via epoxidation of fatty acid alkyl esters using the acidic ionic liquids as catalysts. The epoxidized fatty acid alkyl esters perform well as bio-plasticizers, which could be substituted for phthalate ester plasticizers. The acidic ionic liquids catalysts provide good catalytic performance, are easy to separate, reusable, and may reduce corrosion of pipelines.Type: GrantFiled: August 5, 2016Date of Patent: October 9, 2018Assignee: CPC CORPORATION, TAIWANInventors: You-Liang Tu, Ya-Shiuan Lin, Ming-Tsang Tsai, Chiu-Ping Li, Jung-Chung Wu
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Patent number: 10053439Abstract: A catalytic system containing a titanium zeolite of structure type MWW optionally containing zinc and containing at least one of an inorganic potassium salt and an organic potassium salt is provided. The catalyst system is useful in the preparation of propylene oxide.Type: GrantFiled: June 29, 2017Date of Patent: August 21, 2018Assignees: BASF SE, DOW Global Technologies LLCInventors: Dominic Riedel, Joaquim Henrique Teles, Ulrike Wegerle, Andrei-Nicolae Parvulescu, Alexander Schroeder, Luise Spiske, Daniel Urbanczyk, Ulrich Mueller, Werner Witzl, Meinolf Weidenbach
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Patent number: 9943838Abstract: The present invention relates to a process for the regeneration of a catalyst comprising a titanium-containing zeolite, said catalyst having been used in a process for the preparation of an olefin oxide and having phosphate deposited thereon, said process for the regeneration comprising the steps: (a) separating the reaction mixture from the catalyst, (b) washing the catalyst obtained from (a) with liquid aqueous system; (c) optionally drying the catalyst obtained from (b) in a gas stream comprising an inert gas at a temperature of less than 300° C.; (d) calcining the catalyst obtained from (c) in a gas stream comprising oxygen at a temperature of at least 300° C.Type: GrantFiled: July 16, 2014Date of Patent: April 17, 2018Assignees: BASF SE, Dow Global Technologies LLCInventors: Andrei-Nicolae Parvulescu, Ulrich Mueller, Joaquim Henrique Teles, Bianca Seelig, Philip Kampe, Markus Weber, Peter Resch, Christian Bartosch, Dominic Riedel, Daniel Urbanczyk, Alexander Schroeder, Ulrike Wegerle
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Patent number: 9914993Abstract: Provided is a compact thermal spray powder suitable for forming a ceramic thermal spray coating which is compact and excels in durability. The thermal spray powder disclosed herein includes ceramic particles formed of a ceramic material with a melting point equal to or lower than 2000° C. The thermal spray powder is configured such that the peak top of a main peak is in a range of 10 ?m or less in a log differential pore volume distribution obtained by a mercury porosimetry, and when the peak top of a second peak is at a fine pore size less than that of the peak top of the main peak, the ratio (H2/H1) of the height H2 of the second peak to the height H1 of the main peak is 0.05 or less.Type: GrantFiled: February 23, 2016Date of Patent: March 13, 2018Assignee: FUJIMI INCORPORATEDInventors: Hiroyuki Ibe, Kazuyuki Tsuzuki
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Patent number: 9873653Abstract: Disclosed herein are a heterogeneous catalyst for the preparation of 3-hydroxypropionic acid (3-HPA) from allyl alcohol, and a method for the preparation of 3-HPA from allyl alcohol using the catalyst. In the presence of the heterogeneous catalyst containing gold on a carrier, a liquid-phase reaction is conducted to produce 3-HPA from allyl alcohol at high yield.Type: GrantFiled: December 22, 2014Date of Patent: January 23, 2018Assignee: LG CHEM, LTD.Inventors: Dae Sung Kim, Won Jae Lee, Yong-Jin Choe, Hyunjoo Lee, Sungpil Yang
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Patent number: 9732054Abstract: A continuous process for the preparation of propylene oxide, comprising (a) reacting propene, optionally admixed with propane, with hydrogen peroxide in a reaction apparatus in the presence of acetonitrile as solvent, obtaining a stream S0 containing propylene oxide, acetonitrile, water, at least one further component B, optionally propene and optionally propane, wherein the normal boiling point of the at least one component B is higher than the normal boiling point of acetonitrile and wherein the decadic logarithm of the octanol-water partition coefficient (log Kow) of the at least one component B is greater than zero; (b) separating propylene oxide from S0, obtaining a stream S1 containing acetonitrile, water and the at least one further component B; (c) dividing S1 into two streams S2 and S3; (d) subjecting S3 to a vapor-liquid fractionation in a fractionation unit, obtaining a vapor fraction stream S4 being depleted of the at least one component B; (e) recycling at least a portion of S4, optionally afterType: GrantFiled: August 24, 2016Date of Patent: August 15, 2017Assignees: BASF SE, Dow Global Technologies LLCInventors: Joaquim Henrique Teles, Dominic Riedel, Bianca Seelig, Philip Kampe, Daniel Urbanczyk, Markus Weber, Alexander Schroeder, Andrei-Nicolae Parvulescu, Ulrich Mueller, Meinolf Weidenbach, Werner J. Witzl, Holger Baer
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Patent number: 9687838Abstract: A process for the regeneration of a supported noble metal catalyst comprising contacting the catalyst with a liquid aqueous system at a temperature in the range of from 90 to 160° C., wherein the pH of the aqueous system is outside the range of from 6 to 8, separating the aqueous system from catalyst; and subjecting the catalyst to calcination.Type: GrantFiled: June 17, 2014Date of Patent: June 27, 2017Assignees: BASF SE, Dow Global Technologies LLCInventors: Thomas Heidemann, Barbara Becker
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Patent number: 9688648Abstract: A continuous process for the preparation of propylene oxide, comprising (i) providing a liquid feed stream comprising propene, hydrogen peroxide, acetonitrile, water, dissolved potassium dihydrogen phosphate, and optionally propane; (ii) passing the liquid feed stream provided in (i) into an epoxidation reactor comprising a catalyst comprising a titanium zeolite of structure type MWW, and subjecting the liquid feed stream to epoxidation reaction conditions; (iii) removing an effluent stream from the epoxidation reactor; wherein the concentration of the dissolved potassium dihydrogen phosphate in the liquid feed stream is at least 10% of the solubility limit of the potassium dihydrogen phosphate in the liquid feed stream.Type: GrantFiled: July 16, 2014Date of Patent: June 27, 2017Assignees: BASF SE, Dow Global Technologies LLCInventors: Joaquim Henrique Teles, Bianca Seelig, Dominic Riedel, Philip Kampe, Daniel Urbanczyk, Markus Weber, Ulrich Mueller, Andrei-Nicolae Parvulescu, Alexander Schroeder, Meinolf Weidenbach, Werner Witzl
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Patent number: 9682909Abstract: The present invention relates to a process for hydroxylation of a compound of formula (I) by reacting the compound of formula (I) with an oxidizing agent, in the presence of a titanium silicalite zeolite prepared by crystallization preceded by a maturing step. The present invention also relates to a titanium silicalite zeolite and to the process for preparing same.Type: GrantFiled: February 15, 2013Date of Patent: June 20, 2017Assignees: Rhodia Operations, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE—CNRSInventors: Thibaut Corre, Belen Albela, Laurent Bonneviot, Laurent Garel
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Patent number: 9580397Abstract: A process for preparing a divinylarene dioxide including the steps of: (a) feeding one or more feed streams of the following reactants into a reactor system: (i) at least one divinylarene, (ii) at least one oxidizing agent, and (iii) at least one solvent to form a reaction mixture in the reactor system; (b) continuously reacting together the one or more feed streams of the reactants of step (a) in the reaction mixture; and (c) controlling heat removal of the reaction mixture as the reactants of step (b) react together; wherein the heat removal is sufficient to provide a residence time of the reactants in the reaction mixture of less than about 180 minutes residence time of the reactants in the reaction step (b); and an apparatus for preparing a divinylarene dioxide.Type: GrantFiled: June 3, 2014Date of Patent: February 28, 2017Assignee: BLUE CUBE IP LLCInventors: Kishori Deshpande, David Jean, Jianping Zeng, Ravindra S. Dixit, David H. West
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Patent number: 9284326Abstract: The present invention provides a method for producing an epoxy compound by expoxidation of an olefin compound with good productivity wherein a compound having a carbon-carbon double bond is reacted with hydrogen peroxide in the coexistence of (a) a compound having a carbon-carbon double bond, (b) a hydrogen peroxide solution, (c) a powdered solid catalyst support and (d) a powdered catalyst and optionally (e) an organic solvent, the total mass of (c) and (d) being 100 percent by mass or less on the basis of the total mass of (a), (b) and (e).Type: GrantFiled: April 26, 2013Date of Patent: March 15, 2016Assignees: JX Nippon Oil & Energy Corporation, OSAKA UNIVERSITYInventors: Junko Ichihara, Shunro Yamaguchi, Atsushi Kameyama, Takashi Suzuki, Takashi Morikita
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Patent number: 9266899Abstract: In order to produce an epoxy compound with a less chlorine content at a higher reaction rate and yield, the present invention provides a method for producing an epoxy compound by reacting a compound having a carbon-carbon double bond with hydrogen peroxide in the coexistence of the compound having a carbon-carbon double bond, the hydrogen peroxide solution, a powdered solid catalyst support and a powdered solid catalyst all together, the solid catalyst comprising isopolyacids produced from (a) tungstic acid or a salt thereof and (b) a quaternary ammonium salt compound and/or a pyridinium salt, selected from halogen-free compounds.Type: GrantFiled: April 26, 2013Date of Patent: February 23, 2016Assignees: JX Nippon Oil & Energy Corporation, OSAKA UNIVERSITYInventors: Junko Ichihara, Shunro Yamaguchi, Atsushi Kameyama, Takashi Suzuki, Takashi Morikita
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Patent number: 9227947Abstract: The invention relates to a process for the manufacture of epichlorohydrin (“ECH”) by catalytic oxidation of allyl chloride (“AC”) with an oxidant wherein the catalytic oxidation is performed in an aqueous reaction medium, wherein a water-soluble manganese complex is used as oxidation catalyst, followed by the isolation of epichlorohydrin.Type: GrantFiled: May 22, 2014Date of Patent: January 5, 2016Assignee: HEXION INC.Inventors: Ron Postma, Prasad Muppa
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Patent number: 9212188Abstract: The present invention provides a method for producing an alicyclic diepoxy compound at a higher yield by carrying out epoxidation of an alicyclic olefin compound at a higher reaction rate. The method is a method for producing an alicyclic diepoxy compound represented by formula (1) below by reacting an alicyclic olefin compound represented by formula (2) below with hydrogen peroxide in the coexistence of the alicyclic olefin compound represented by formula (2) below, a hydrogen peroxide solution, a powdered solid catalyst support and a powdered solid catalyst all together: wherein R1 to R12 are each hydrogen, halogen, an alkyl group optionally having halogen or an alkoxy group optionally having a substituent.Type: GrantFiled: April 26, 2013Date of Patent: December 15, 2015Assignees: JX Nippon Oil & Enery Corporation, OSAKA UNIVERSITYInventors: Junko Ichihara, Shunro Yamaguchi, Atsushi Kameyama, Takashi Suzuki, Takashi Morikita
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Patent number: 9187443Abstract: A method is provided for carrying out epoxidation of an olefin compound with good productivity. The method produces an epoxy compound by reacting a compound having a carbon-carbon double bond with hydrogen peroxide by carrying out repeatedly or continuously the following steps: (1) reacting a compound having a carbon-carbon double bond with hydrogen peroxide in the coexistence of (a) the compound having a carbon-carbon double bond, (b) a hydrogen peroxide solution, (c) a powdered solid catalyst support, and (d) a powdered solid catalyst, and optionally further (e) an organic solvent to produce an epoxy compound; (2) separating the epoxy compound reaction product from the reaction mixture produced in (1); and (3) adding (d) and also adding (a), (b), (c), and optionally further (e) to the mixture of the powdered solid catalyst support and powdered solid catalyst after separating the reaction product in (2).Type: GrantFiled: April 26, 2013Date of Patent: November 17, 2015Assignees: JX Nippon Oil & Energy Corporation, OSAKA UNIVERSITYInventors: Junko Ichihara, Shunro Yamaguchi, Atsushi Kameyama, Takashi Suzuki, Takashi Morikita
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Patent number: 9174955Abstract: The invention relates to a process for the manufacture of an epoxyethyl carboxylate or glycidyl carboxylate, including reacting a vinyl carboxylate or an allyl carboxylate using an oxidant and a water-soluble manganese complex in an aqueous reaction medium, and the water-soluble manganese complex comprises an oxidation catalyst, characterized in that the water-soluble manganese complex is a mononuclear species of the general formula (I) [LMnX3]Y (I), or a binuclear species of the general formula (II): [LMn(?-X)3MnL]Yn (II), wherein Mn is a manganese; L is a ligand and each L is independently a polydentate ligand, each X is independently a coordinating species and each ?-X is independently a bridging coordinating species, Y is a non-coordinating counter ion, and wherein the epoxidation is carried out at a pH in the range of from 1.0 to 7.0.Type: GrantFiled: January 26, 2011Date of Patent: November 3, 2015Assignee: HEXION INC.Inventors: Prasad Muppa, Ron Postma, Caspar Schoolderman, Sandra Rens, Kostas Stoitsas
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Patent number: 9115463Abstract: The present invention concerns the treatment of substrates with a preformed transition metal catalyst in an aqueous solution. The transitional metal catalyst is a dinuclear Mn transitional metal catalyst and its ligand has the following formula (I): and p is 3.Type: GrantFiled: April 15, 2011Date of Patent: August 25, 2015Assignee: Catexel LimitedInventors: Ronald Hage, Fabien Pierre Guy Gaulard, Kimberly Soraya Yang
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Patent number: 9108188Abstract: A composition comprising an extruded inorganic support comprising an oxide of a metal or metalloid, and at least one catalytically active metal, wherein the extruded inorganic support has pores, a total pore volume, and a pore size distribution, wherein the pore size distribution displays at least two peaks of pore diameters, each peak having a maximum, wherein a first peak has a first maximum of pore diameters of equal to or greater than about 120 nm and a second peak has a second maximum of pore diameters of less than about 120 nm, and wherein greater than or equal to about 5% of a total pore volume of the extruded inorganic support is contained within the first peak of pore diameters.Type: GrantFiled: March 7, 2012Date of Patent: August 18, 2015Assignee: Chevoron Phillip Chemical Company, LPInventors: Tin-Tack Peter Cheung, Joseph Bergmeister, III, Stephen L. Kelly
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Patent number: 9102640Abstract: Apparatus and processes are provided for forming epoxide compounds. In one embodiment, a process for the manufacture of an epoxide is provided including adding an oxidant, a water-soluble manganese complex and a terminal olefin to form a multiphasic reaction mixture, reacting the terminal olefin with the oxidant in the multiphasic reaction mixture having at least one organic phase in the presence of the water-soluble manganese complex, separating the reaction mixture into the at least one organic phase and an aqueous phase, and reusing at least part of the aqueous phase. The invention is also related to a device for performing the above process.Type: GrantFiled: February 19, 2014Date of Patent: August 11, 2015Assignee: Evonik Degussa GmbHInventors: Prasad Muppa, Ron Postma, Bart Van Den Berg, Jürgen Stock, Holger Wiederhold, Hans Rausch, Jörg Schallenberg, Stefan Bernhardt
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Patent number: 9051287Abstract: A method for producing an epoxide is provided. The method includes a step of performing a reaction of an olefine compound and an oxidant to form the epoxide by using a titanium-silicon molecular sieve as a catalyst, thereby increasing the conversion rate of the oxidant and the yield of the epoxide.Type: GrantFiled: October 29, 2013Date of Patent: June 9, 2015Assignee: China Petrochemical Development CorporationInventors: Yu-Chuan Hsu, Cheng-Fa Hsieh
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Patent number: 9045446Abstract: To provide a method for producing an epoxy compound having fewer residual quaternary salt compound by removing the quaternary salt compound from an organic solution containing an epoxy compound and the quaternary salt compound.Type: GrantFiled: July 2, 2013Date of Patent: June 2, 2015Assignee: ARAKAWA CHEMICAL INDUSTRIES, LTD.Inventors: Naoki Sasagawa, Kiyoshi Takumi, Yoichiro Ezaki
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Patent number: 9024048Abstract: Apparatus and methods are provided for forming and processing multiphasic systems. In one embodiment, the invention provides a process for the manufacture of an epoxide, including reacting an olefinically unsaturated compound with an oxidant in the presence of a buffer component and a water-soluble manganese complex disposed in an aqueous phase having a first pH level in a first multiphasic system, adjusting the pH of the aqueous phase to a second pH level less than the first pH level, isolating at least a portion of the aqueous phase from the first multiphasic system, adjusting the pH of the at least a portion of the aqueous phase to a third pH level greater than the second pH level, and introducing the at least a portion of the aqueous phase into a second multiphasic system.Type: GrantFiled: June 13, 2012Date of Patent: May 5, 2015Assignee: Evonik Degussa GmbHInventors: Mark Kapellen, Bart Van Den Berg, Prasad Muppa, Paul Haesakkers
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Patent number: 8975423Abstract: Processes and compositions are provided for epoxidizing an olefinically unsaturated compound. In one embodiment, a process is provided for reacting an olefinically unsaturated compound with an oxidant in the presence of a catalyst at acidic conditions, wherein the catalyst is activated prior to the reaction at a pH that is higher than the pH during the reaction.Type: GrantFiled: January 26, 2011Date of Patent: March 10, 2015Assignee: Hexion Inc.Inventors: Prasad Muppa, Mark Kapellen, Caspar Schoolderman
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Patent number: 8927745Abstract: A process for producing propylene oxide comprising reacting propene with hydrogen peroxide in the presence of a catalyst to give a mixture (G1) comprising propylene oxide, unreacted propene, and oxygen; separating propylene oxide from mixture (G1) to give a mixture (GII) comprising propene and oxygen; and adding hydrogen to mixture (GII) and reducing the oxygen comprised in mixture (GII) at least partially by reaction with hydrogen in the presence of a catalyst comprising copper in elemental and/or oxidic form on a support, wherein copper is present on the support in an amount of 30 to 80 wt.-% based on the whole catalyst and calculated as CuO.Type: GrantFiled: May 5, 2010Date of Patent: January 6, 2015Assignees: BASF SE, The Dow Chemical CompanyInventors: Philip Kampe, Peter Resch, Soo Yin Chin, Peter Bassler, Ulrich Mueller, Goetz-Peter Schindler, Hans-Georg Goebbel, Joaquim Henrique Teles, Kai Gumlich, Thomas Grassler, Christian Bartosch, Richard Jacubinas, Meinolf Weidenbach
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Patent number: 8907112Abstract: A method for producing an epoxide is disclosed. The method includes performing a reaction of an olefin compound and an oxidant by using a titanium-silicon molecular sieve as a catalyst, in the presence of a silicon oxide containing an alkaline earth metal as a coagent. The selectivity and yield of epoxide are increased by using a silicon oxide containing an alkaline metal as a coagent.Type: GrantFiled: December 11, 2013Date of Patent: December 9, 2014Assignee: China Petrochemical Development CorporationInventors: Yu-Chuan Hsu, Cheng-Fa Hsieh
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Patent number: 8895763Abstract: An integrated process for preparing alkylene oxides and alkylene glycols is described. For this purpose, an alkylene oxide plant and an alkylene glycol plant are combined with one another and the water originating from the alkylene oxide plant and also other constituents of the reaction mixture are introduced into the alkylene glycol plant. In this way, alkylene glycols which have been produced in the alkylene oxide plant can be recovered as materials of value and the water circulation into the alkylene glycol plant can be eliminated or drastically reduced. In addition, the energy-intensive treatment of the process water from the alkylene oxide plant can be dispensed with. The integration of the two processes leads overall to better energy efficiency and conservation of resources in the work-up of residues from the process.Type: GrantFiled: August 12, 2010Date of Patent: November 25, 2014Assignee: Thyssenkrupp UHDE GmbHInventor: Ferdinand Rudolf Reif
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Patent number: 8889893Abstract: Process for the manufacture of 1,2-epoxy-3-chloropropane by reaction between allyl chloride and hydrogen peroxide in the presence of a catalyst and in the possible presence of at least one solvent, in which the allyl chloride employed comprises less than 2000 ppm by weight of 1,5-hexadiene.Type: GrantFiled: September 13, 2010Date of Patent: November 18, 2014Assignee: Solvay (SociétéAnonyme)Inventors: Michel Strebelle, Jean-Pierre Catinat
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Patent number: 8859791Abstract: A process for producing an alkylene oxide by olefin epoxidation, wherein said process comprises the steps of: (1) in a first olefin epoxidation condition, in the presence of a first solid catalyst, a first mixed stream containing a solvent, an olefin and H2O2 is subjected to an epoxidation in one or more fixed bed reactors and/or one or more moving bed reactors until the conversion of H2O2 reaches 50%-95%, then, optionally, the resulting reaction mixture obtained in the step (1) is subjected to a separation to obtain a first stream free of H2O2 and a second stream containing the unreacted H2O2, and the olefin is introduced to the second stream to produce a second mixed stream, or optionally, the olefin is introduced to the reaction mixture obtained in the step (1) to produce a second mixed stream; (2) in a second olefin epoxidation condition, the reaction mixture obtained in the step (1) or the second mixed stream obtained in the step (1) and a second solid catalyst are introduced to one or more slurry bed reType: GrantFiled: October 11, 2011Date of Patent: October 14, 2014Assignees: China Petroleum & Chemical Corporation, Hunan Changling Petrochemical Science and Technology Development Co. Ltd., Research Institute of Petroleum Processing, SinopecInventors: Hua Li, Min Lin, Xiaoju Wu, Wei Wang, Chijian He, Jizao Gao, Xingtian Shu, Shuanghua Wan, Bin Zhu
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Patent number: 8859790Abstract: Apparatus and processes are provided for forming epoxide compounds. In one embodiment, a process for the manufacture of an epoxide is provided including adding an oxidant, a water-soluble manganese complex and a terminal olefin to form a multiphasic reaction mixture, reacting the terminal olefin with the oxidant in the multiphasic reaction mixture having at least one organic phase in the presence of the water-soluble manganese complex, separating the reaction mixture into the at least one organic phase and an aqueous phase, and reusing at least part of the aqueous phase. The invention is also related to a device for performing the above process.Type: GrantFiled: January 26, 2011Date of Patent: October 14, 2014Assignee: Momentive Specialty Chemicals Inc.Inventors: Prasad Muppa, Ron Postma, Bart Van Den Berg, Juergen Stock, Holger Wiederhold, Hans Rausch, Jorg Schallenberg, Stefan Bernhardt
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Publication number: 20140296545Abstract: The invention relates to a process for the manufacture of a 1,2-epoxide by catalytic oxidation of a terminal olefin with hydrogen peroxide wherein the catalytic oxidation is performed in a biphasic system comprising an organic phase and an aqueous reaction medium, wherein a water-soluble manganese complex is used as oxidation catalyst, wherein a terminal olefin is used with a solubility at 20° C. of at least 0.01 to 100 g in 1 liter water, and wherein the molar ratio of terminal olefin to hydrogen peroxide is in the range of from 1:0.1 to 1:2.Type: ApplicationFiled: March 24, 2014Publication date: October 2, 2014Applicant: Momentive Specialty Chemicals Inc.Inventors: Ron Postma, Prasad Muppa
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Publication number: 20140256968Abstract: The invention relates to a process for the manufacture of epichlorohydrin (“ECH”) by catalytic oxidation of allyl chloride (“AC”) with an oxidant wherein the catalytic oxidation is performed in an aqueous reaction medium, wherein a water-soluble manganese complex is used as oxidation catalyst, followed by the isolation of epichlorohydrin.Type: ApplicationFiled: May 22, 2014Publication date: September 11, 2014Applicant: Momentive Specialty Chemicals Inc.Inventors: Ron POSTMA, Prasad MUPPA
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Publication number: 20140256969Abstract: A process for preparing a divinylarene dioxide including reacting (a) at least one divinylarene, (b) hydrogen peroxide, (c) at least one iron-containing catalyst, and (d) an excess of amine hydrogen halide, under conditions to form a divinylarene dioxide.Type: ApplicationFiled: October 16, 2012Publication date: September 11, 2014Inventors: Robert J. Wright, Kevin A. Frazier, Gyongyi Gulyas
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Patent number: 8802873Abstract: The invention relates to a process for the manufacture of epichlorohydrin (“ECH”) by catalytic oxidation of allyl chloride (“AC”) with an oxidant wherein the catalytic oxidation is performed in an aqueous reaction medium, wherein a water-soluble manganese complex is used as oxidation catalyst, followed by the isolation of epichlorohydrin.Type: GrantFiled: July 9, 2009Date of Patent: August 12, 2014Assignee: Momentive Specialty Chemicals Inc.Inventors: Ron Postma, Prasad Muppa
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Patent number: 8796478Abstract: Process for the manufacture of 1,2-epoxy-3-chloropropane by reaction between allyl chloride and hydrogen peroxide in the presence of a solid catalyst and in the possible presence of at least one solvent in an epoxidation medium comprising at least two liquid phases under the conditions of reaction, comprising feeding continuously a reaction zone comprising the catalyst with at least allyl chloride, hydrogen peroxide and possibly at least one solvent at a total liquid linear velocity higher than or equal to 0.01 m/s and lower than or equal to 1 m/s, wherein the pressure drop across the reaction zone is lower than or equal to 25 kPa/m.Type: GrantFiled: January 25, 2012Date of Patent: August 5, 2014Assignee: Solvay SAInventors: Patrick Gilbeau, Frederic Gillin