Group Va Element (n, P, As, Sb, Or Bi) Containing Material Utilized (e.g., Arsenic Containing Ligand Utilized, Etc.) Patents (Class 568/454)
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Patent number: 12037313Abstract: A process for producing ethylene and at least one of butanol and an alkyl tert-butyl ether from field butane includes separating the field butane into an n-butane stream and an isobutane stream; cracking the n-butane stream to obtain a cracked product stream comprising n-butane, 1-butene, 2-butene, butadienes, or a combination comprising at least one of the foregoing; and at least one of the following: (1) separating the cracked product stream to obtain a butane stream and a butene stream, and reacting the butene stream with water to obtain a fuel additive comprising butanol, and (2) dehydrogenating the isobutane stream in a dehydrogenation unit to form an isobutene stream and reacting the isobutene stream with an aliphatic alcohol to produce an alkyl tert-butyl ether.Type: GrantFiled: November 20, 2019Date of Patent: July 16, 2024Assignee: SABIC GLOBAL TECHNOLOGIES B.V.Inventors: Vijay Dinkar Bodas, Guillermo Leal, Mohammed Bismillah Ansari
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Patent number: 12017982Abstract: A process for the hydroformylation of olefins to aldehydes is disclosed. The process comprises: hydroformylating one or more olefins with hydrogen and carbon monoxide in the presence of a ligand-rhodium catalyst in a reaction zone; recovering a reactor effluent from the reaction zone, the reactor effluent comprising product aldehyde and the ligand-rhodium catalyst; passing the reactor effluent and a strip gas to a vaporiser, wherein the strip gas comprises carbon monoxide and is formed from a recycle strip gas stream and a make-up strip gas stream, wherein the product aldehyde is vaporised into the strip gas in the vaporiser resulting in a vapour mixture, comprising the strip gas and the product aldehyde, and a liquid mixture, comprising the ligand-rhodium catalyst; recovering the liquid mixture and recycling the ligand-rhodium catalyst to the reaction zone; recovering the vapour mixture and separating the product aldehyde from the vapour mixture.Type: GrantFiled: May 29, 2020Date of Patent: June 25, 2024Assignee: Johnson Matthey Davy Technologies LimitedInventors: Fraser Robert Archibald, Robert Arthur Jolly, Maria del Amo Lopez, David Keith Welch
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Patent number: 11993567Abstract: A method for preparing an aldehyde including forming a reaction product including an aldehyde by reacting an olefin-based compound with a synthetic gas in a hydroformylation reactor in the presence of a hydroformylation catalyst; introducing the reaction product including the aldehyde to a vaporizer; separating low-boiling point components of the reaction product from an upper part of a vaporizer catch pot included in the vaporizer; separating high-boiling point components of the reaction product from a lower part of the vaporizer catch pot; and recirculating at least a portion of the low-boiling point components separated from an upper part of the vaporizer catch pot back to the vaporizer.Type: GrantFiled: August 26, 2021Date of Patent: May 28, 2024Assignee: LG Chem, Ltd.Inventors: Jusang Yang, Sangjun Shin, Sungshik Eom, Tae Yun Kim, Dong Hyun Ko, Sungpil Yang
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Patent number: 11981628Abstract: Use of a method for reduction of heavy end formation and catalyst loss in a hydroformylation process, wherein the method comprises the steps; a) Reacting an olefin and syngas in a reactor assembly (1) utilizing at least one catalyst and at least one ligand, b) Separating an obtained aldehyde from a mixture of aldehyde, catalyst, ligand and early heavy ends in a distillation unit (2), c) Entering the mixture of catalyst, ligand, early heavy ends and rest aldehyde into a short residence time evaporator unit (3) having at least a first rest aldehyde stripper stage (3a) and at least one last early heavy ends stripper stage (3b). Said evaporator units (3) being of a falling film and/or wiped film type, d) That the catalyst/ligand mixture from a lower end (3b1) of the at least one last early heavy ends stripping stage (3b) is entered into a cooling unit (4) immediately after stripping of early heavy ends.Type: GrantFiled: June 12, 2020Date of Patent: May 14, 2024Assignee: PERSTORP ABInventors: Matias Kangas, Stefan Nilsson
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Patent number: 11981629Abstract: The present invention refers to a method for reducing heavy end formation and catalyst loss in a continuous hydroformylation process, where an olefin or an olefin mixture is reacted with carbon monoxide and hydrogen in a reactor assembly (1) in the presence of a rhodium complex catalyst, comprising at least one organobisphosphite ligand, in order to produce an aldehyde. Said method comprising the addition of an epoxide to the reaction mixture and the continuous or discontinuous removal of early heavy ends.Type: GrantFiled: June 23, 2020Date of Patent: May 14, 2024Assignee: PERSTORP ABInventors: Matias Kangas, Stefan Nilsson
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Patent number: 11680032Abstract: A process for producing branched alcohols through isomerization, hydroformylation and hydrogenation.Type: GrantFiled: April 30, 2021Date of Patent: June 20, 2023Assignee: SCION Holdings LLCInventors: Kyle Killebrew, Samuel Livingston Lane
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Patent number: 11370737Abstract: A process of co-feeding gaseous ethylene with liquid allyl alcohol in the presence of a catalyst to produce 1,4-butanediol and n-propanol may include: introducing a gaseous mixture of ethylene, carbon monoxide and hydrogen into a reactor in the presence of a hydroformylation catalyst in a solvent; introducing liquid allyl alcohol (AA) into the reactor; and carrying out hydroformylation reaction at a temperature between 50 and 100° C. to obtain hydroformylation products.Type: GrantFiled: September 21, 2021Date of Patent: June 28, 2022Assignee: Lyondell Chemical Technology, L.P.Inventors: Daniel F. White, Beaven S. Mandimutsira, Roberto Alvarez
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Patent number: 11130725Abstract: The present invention relates to methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in a hydroformylation process. In one aspect, a method comprises (a) contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a tetraphosphine having the structure described herein, and, optionally, (C) a monophosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions; and (b) adding additional monophosphine having the structure described herein to a reaction zone.Type: GrantFiled: May 3, 2019Date of Patent: September 28, 2021Assignee: Dow Technology Investments LLCInventors: Michael A. Brammer, Michael C. Becker, William N. Felsted, II
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Patent number: 10913055Abstract: A hydroformylation catalyst having excellent catalytic activity and stability, a composition including the hydroformylation catalyst, and a method of preparing an aldehyde using the hydroformylation catalyst, wherein, when hydroformylation of an olefin compound is performed in the presence of the hydroformylation catalyst to prepare an aldehyde, the normal/iso (n/i) ratio of the prepared aldehyde is lowered, and synthesis gas yield is increased.Type: GrantFiled: July 4, 2017Date of Patent: February 9, 2021Assignee: LG CHEM, LTD.Inventors: Mi Young Kim, Sung Shik Eom, Dong Hyun Ko, Da Won Jung, Tae Yun Kim, Min Ji Choi
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Patent number: 10807934Abstract: A process for selectively producing 4-hydroxybutyraldehyde from allyl alcohol is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a trans-1,2-bis(bis(3,4,5-tri-n-alkylphenyl)phosphinomethyl)-cyclobutane. The process gives high yield of 4-hydroxybutyraldehyde compared to temperature.Type: GrantFiled: May 22, 2020Date of Patent: October 20, 2020Assignee: Lyondell Chemical Technology, L.P.Inventors: Daniel F. White, Beaven S. Mandimutsira
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Patent number: 10766839Abstract: The present invention relate to processes for converting olefins to alcohols, ethers, or combinations thereof that are suitable for use as a gasoline additive. In one embodiment, the process comprises (a) receiving a feed stream, wherein the feed stream comprises one or more olefins having 2 to 5 carbon atoms in an amount of up to 80% by weight based on the weight of the feed stream; (b) hydroformylating the feed stream in the presence of a catalyst to convert at least 80% of the olefins from the feed stream to oxygenates; (c) separating a product stream from step (b) into an oxygenate stream and a stream comprising unreacted olefins, inerts, the catalyst, and the remaining oxygenates; and (d) treating the oxygenate stream to convert a plurality of the oxygenates into at least one of an alcohol, an ether, or combinations thereof is suitable for use as a gasoline additive.Type: GrantFiled: February 10, 2017Date of Patent: September 8, 2020Assignee: Dow Technology Investments LLCInventors: Michael C. Becker, Michael A. Brammer, Jason F. Giles, Glenn A. Miller, George R. Phillips, Rick B. Watson, Stephane Wambergue, Martin Lucas Smidt
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Patent number: 10747292Abstract: The application provides a Dynamic Voltage Frequency Scaling device including an information acquisition unit configured to acquire working state information or application scenario information of a chip connected with the Dynamic Voltage Frequency Scaling device in real time and a voltage frequency scaling unit configured to send voltage frequency scaling information to the chip according to the working state information or the application scenario information of the chip. The embodiment of the application dynamically scales the voltage frequency on chip-level and reduces the power consumption of chips.Type: GrantFiled: August 1, 2019Date of Patent: August 18, 2020Assignee: SHANGHAI CAMBRICON INFORMATION TECHNOLOGY CO., LTDInventors: Shaoli Liu, Lei Zhang, Tianshi Chen
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Patent number: 10684239Abstract: A system and a method for applying 13C or 1H NMR spectroscopy to a sample of oil in order to calculate and assign an indicative property such as cetane number, pour point, cloud point, aniline point and/or octane number of a gas oil or naphtha fraction of the crude oil.Type: GrantFiled: June 30, 2017Date of Patent: June 16, 2020Assignee: SAUDI ARABIAN OIL COMPANYInventors: Omer Refa Koseoglu, Adnan Al-Hajji, Mohammed Abdullah Al-Ghamdi, Alexander Rebrov
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Patent number: 10478812Abstract: The catalyst solution used in a hydroformylation process is prepared for storage by first reducing its acid concentration and/or water content, and then storing the solution under a blanket of syngas and/or an inert gas. Alternatively, or in addition to, the catalyst solution can be stored with an aqueous buffer comprising materials that will neutralize and/or absorb the acid species within the catalyst solution.Type: GrantFiled: April 13, 2012Date of Patent: November 19, 2019Assignees: Dow Technology Investments LLC, BASF SEInventors: Thomas C. Eisenschmid, Michael C. Becker, Donald L. Campbell, Jr., Michael A. Brammer, Glenn A. Miller, Edward Adrian Lord, Jens Rudolph, Hans-Rüdiger Reeh
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Patent number: 10407372Abstract: Embodiments of the present invention relate to processes for the hydroformylation of olefins to produce aldehydes. In some embodiments, processes of the present invention are capable of maintaining high C2-C4 olefin conversion and/or provide more compact hydroformlyation processes.Type: GrantFiled: March 15, 2017Date of Patent: September 10, 2019Assignee: Dow Technology Investments LLCInventors: Kathleen Simpson, Gerald L. Smith
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Patent number: 10294428Abstract: Provided is a composition capable of safely and efficiently removing a sulfur-containing compound, especially hydrogen sulfide, an —SH group-containing compound or a mixture thereof contained in a hydrocarbon, and not causing metal corrosion in devices. The composition is for removing a sulfur-containing compound in a hydrocarbon, wherein the sulfur-containing compound is hydrogen sulfide, an —SH group-containing compound or a mixture thereof, and the composition contains a dialdehyde having 6 to 16 carbon atoms and a polyalkylene glycol.Type: GrantFiled: January 26, 2016Date of Patent: May 21, 2019Assignee: KURARAY CO., LTD.Inventors: Takahiro Suzuki, Yuusuke Saitou
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Patent number: 10119079Abstract: Disclosed is a composition capable of removing safely and efficiently a sulfur-containing compound contained in a hydrocarbon, particularly hydrogen sulfide, an —SH group-containing compound, or a mixture thereof. Provided is a composition for removal of a sulfur-containing compound in a hydrocarbon, the sulfur-containing compound being hydrogen sulfide, an —SH group-containing compound or a mixture thereof: the composition containing a dialdehyde having 6 to 16 carbon atoms as an active ingredient.Type: GrantFiled: March 11, 2015Date of Patent: November 6, 2018Assignee: KURARAY CO., LTD.Inventors: Junichi Fuji, Ryoko Miyazaki, Takahiro Suzuki
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Patent number: 9908910Abstract: The invention relates to Rh, Ru, Co and Ir complexes comprising bidentate diphosphoramidites as ligands and to the use thereof as catalysts for the hydroformylation of olefins. The invention also relates to a process for preparing an aldehyde from an olefin using the complexes or ligands mentioned.Type: GrantFiled: December 16, 2016Date of Patent: March 6, 2018Assignee: Evonik Degussa GmbHInventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Frank Geilen, Galina Morales Torres, Detlef Selent, Armin Börner
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Patent number: 9896404Abstract: The invention relates to Rh, Ru, Co and Ir complexes comprising bidentate diphosphoramidites as ligands and to the use thereof as catalysts for the hydroformylation of olefins. The invention also relates to a process for preparing an aldehyde from an olefin using the complexes or ligands mentioned.Type: GrantFiled: December 16, 2016Date of Patent: February 20, 2018Assignee: Evonik Degussa GmbHInventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Frank Geilen, Galina Morales Torres, Detlef Selent, Armin Börner
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Patent number: 9765023Abstract: Novel complexes of diphenyl selenoxides and also use thereof and methods in which the complexes are used.Type: GrantFiled: December 7, 2016Date of Patent: September 19, 2017Assignee: EVONIK DEGUSSA GMBHInventors: Katrin Marie Dyballa, Robert Franke, Detlef Selent, Armin Börner, Claudia Weilbeer
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Patent number: 9737884Abstract: The catalytic preparation of an aldehyde from an olefin proceeds in the presence of a monophosphite mixture.Type: GrantFiled: May 19, 2015Date of Patent: August 22, 2017Assignee: Evonik Degussa GmbHInventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Bart Hamers, Frank Geilen
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Patent number: 9713791Abstract: The invention relates to a process for separating a composition of matter with the aid of a membrane cascade having at least two stages, in which a separation is effected in each stage at at least one membrane at a separation temperature set for the particular stage. The invention further relates to a corresponding membrane cascade, to the use of said membrane cascade for catalyst separation from homogeneously catalyzed mixtures, and to a process for hydroformylation, in which the catalyst is separated by means of a membrane cascade. The problem addressed thereby is that of specifying a membrane-based process for separating compositions of matter, which has a minimum membrane area requirement and nevertheless fulfills the separation task and separation performance required. This problem is solved by the use of a membrane cascade with falling separation temperature.Type: GrantFiled: July 25, 2014Date of Patent: July 25, 2017Assignee: EVONIK DEGUSSA GMBHInventors: Markus Priske, Robert Franke, Bart Hamers, Patrick Schmidt, Andrzej Górak
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Patent number: 9707552Abstract: Disclosed are a catalyst composition containing a phosphorous-based ligand and a hydroformylation process using the same. More specifically, disclosed are a catalyst composition containing a monodentate phosphite ligand, a monodentate phosphine ligand and a transition metal catalyst, wherein the total content of the entire ligand including the monodentate phosphite ligand and the monodentate phosphine ligand is 1 to 33 moles, based on 1 mole of the transition metal catalyst, and a hydroformylation method using the same. The present invention has an effect of providing a catalyst composition which reduces an N/I (ratio of normal to iso) selectivity of aldehydes produced by hydroformylation of an olefin-based compound and exhibits superior catalytic activity and stability, and a hydroformylation method of an olefin-based compound using the catalyst composition.Type: GrantFiled: October 19, 2015Date of Patent: July 18, 2017Assignee: LG CHEM. LTD.Inventors: Mi Young Kim, Min Ji Choi, Sung Shik Eom, Dong Hyun Ko, Da Won Jung, Tae Yun Kim
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Patent number: 9695098Abstract: A multi-reactor hydroformylation process wherein a common product-catalyst separation zone is employed.Type: GrantFiled: December 9, 2014Date of Patent: July 4, 2017Assignee: DOW TECHNOLOGY INVESTMENTS LLCInventors: Glenn A. Miller, Jason F. Giles, Irvin B. Cox
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Patent number: 9688598Abstract: A multi-reaction train hydroformylation process wherein a common product-catalyst separation zone is employed.Type: GrantFiled: December 9, 2014Date of Patent: June 27, 2017Assignee: DOW TECHNOLOGY INVESTMENTS LLCInventors: Thomas C. Eisenschmid, Morteza Mokhtarzadeh, Cloid R. Smith, III, Michael C. Becker, George R. Phillips, Michael A. Brammer, Glenn A. Miller, Rick B. Watson, Irvin B. Cox, Edward A. Lord, Martin Smidt
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Patent number: 9687837Abstract: A new stable, catalytically active, tetradentate organophosphorus modified rhodium hydroformylation catalyst has been discovered that is capable of producing aldehyde products with a high linear/branched product ratio from linear olefins. The tetradentate organophosphorus modifier is a tetrasubstituted 2,2?,2?,5?-tetramethyl-1,1?:4?-1?-terphenyl, whereby, each methyl group has one hydrogen substituted by an R, R?-diorganophosphine moiety. The R, R? may comprise aromatic, alkyl, arylalkyl and alkylaryl groups. The precursor 2,2?,2?,5?-tetramethyl-1,1?:4?,1?-terphenyl hydrocarbon may be prepared from para-xylene and toluene derivatives.Type: GrantFiled: August 31, 2016Date of Patent: June 27, 2017Assignee: Eastman Chemical CompanyInventor: Thomas James Devon
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Patent number: 9670122Abstract: A process of controlling hydroformylation reaction fluid temperature involves controlling the flow rate of reaction fluid through an external heat exchanger.Type: GrantFiled: September 9, 2014Date of Patent: June 6, 2017Assignee: Dow Technology Investments LLCInventors: Cloid R. Smith, III, Morteza Mokhtarzadeh, Irvin B. Cox
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Patent number: 9663434Abstract: A functionalized nanomaterial having an average particles size of less than 10 nm comprising an iron oxide nanoparticle core and a bis(diarylphosphinomethyl) dopamine based ligand layer anchored to the iron oxide nanoparticle core is disclosed. In addition, a catalyst composition for use in a variety of chemical transformations wherein the bisphosphine groups of the functionalized nanomaterial chelate a catalytic metal is disclosed. In addition, a method for producing the functionalized nanomaterial and a method for the hydroformylation of olefins to aldehydes employing the functionalized nanomaterial with high conversion percentage and high selectivity are disclosed.Type: GrantFiled: September 30, 2016Date of Patent: May 30, 2017Assignee: King Fahd University of Petroleum and MineralsInventors: Mohammed Nasiruzzaman Shaikh, Zain Hassan Yamani
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Patent number: 9624153Abstract: The invention relates to processes for preparing aldehydes by hydroformylation of alkenes, in which an alkene-containing feed mixture is subjected to a primary hydroformylation with synthesis gas in the presence of a homogeneous catalyst system, the primary hydroformylation being effected in a primary reaction zone from which a cycle gas containing at least some of the products and unconverted reactants of the primary hydroformylation are drawn off continuously and partly condensed, with recycling of uncondensed components of the cycle gas into the primary reaction zone, and with distillative separation of condensed components of the cycle gas in an aldehyde removal stage to give an aldehyde-rich mixture and a low-aldehyde mixture. The problem that it addresses is that of developing the process such that it achieves high conversions and affords aldehyde in good product quality even in the case of a deteriorating raw material position.Type: GrantFiled: December 10, 2014Date of Patent: April 18, 2017Assignee: Evonik Degussa GmbHInventors: Marc Becker, Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Hanna Hahn, Marina Lazar, Markus Priske, Guido Stochniol
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Patent number: 9616422Abstract: Disclosed are a catalyst composition and a method of hydroformylating olefin using the same, which may maintain catalyst activity through improvement of catalyst stability and reduce a use amount of a ligand while improving selectivity to iso-aldehyde, by using a specific ligand to a transition metal catalyst and a ligand stabilizer together in hydroformylation of olefin.Type: GrantFiled: September 25, 2014Date of Patent: April 11, 2017Assignee: LG CHEM, LTD.Inventors: Sung Shik Eom, Dong Hyun Ko, Da Won Jung, Min Soo Kim, Tae Yun Kim
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Patent number: 9611203Abstract: A method for an olefin hydroformylation reaction comprising subjecting olefins and CO/H2 mixed gas to the olefin hydroformylation reaction in a reactor in the presence of a solid heterogeneous catalyst, which consisting of a metal component and an organic ligand polymer with hierarchical porosity, in which the metal component is one or more of Rh, Ir or Co, the organic ligand polymer is a polymer formed by polymerization of an organic ligand monomer containing P and alkenyl group and optional N, and in the solid heterogeneous catalyst, the metal component forms coordinated bonds with the P atom or N in the backbone of the organic ligand polymer and exists in a monoatomic dispersion state; the reaction technique and device are simple, and the catalyst has a stable hydroformylation property with a high activity and yield.Type: GrantFiled: December 11, 2013Date of Patent: April 4, 2017Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: Yunjie Ding, Li Yan, Miao Jiang, Ronghe Lin
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Patent number: 9610574Abstract: The present invention relates to a composition comprising: a) at least one support material; b) at least one metal selected from transition group VIII of the Periodic Table of the Elements and c) at least one compound of the formula (I) R?-A-R? (I), where A, R? and R? are each an organic radical, where R? and R? have the structural element —O—P(—O—)2 with trivalent P and are bonded covalently to the A radical via the latter, with the proviso that R??R?, to a process for producing such a composition, to the use of the composition and to a process and an apparatus for hydroformylation in which the composition is used.Type: GrantFiled: August 8, 2014Date of Patent: April 4, 2017Assignee: EVONIK DEGUSSA GMBHInventors: Katrin Marie Dyballa, Hanna Hahn, Robert Franke, Dirk Fridag, Marc Becker
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Patent number: 9586197Abstract: A solid heterogeneous catalyst consisting of a metal component and an organic ligand polymer, wherein the metal component is one or more of Rh, Ir or Co, the organic ligand polymer is a polymer having a large specific surface area and hierarchical porosity formed by polymerizing an organic ligand monomer containing P and alkenyl group and optional N via a solvothermal polymerization process, the metal component forms coordinated bond with the P atom or N in backbone of the organic ligand polymer and exists in a monoatomic dispersion state; when the catalyst is used in an olefin hydroformylation reaction, the metal component and the P and/or N atom form in situ an intermediate active species similar to homogeneous catalyst due to the coordination effect, and the catalyst has an excellent catalytic property, can be easily separated, and has a relatively high stability.Type: GrantFiled: December 11, 2013Date of Patent: March 7, 2017Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: Yunjie Ding, Miao Jiang, Li Yan, Ronghe Lin
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Patent number: 9499463Abstract: The invention relates to mixtures of constitutional isomer bisphosphites of formulae (1a) and (2a), to a method for the production thereof, to the reaction thereof with metals to form mixtures containing complex compounds of the constitutional isomer bisphosphites of formulae (1a) and (2a) and the metal, and to the use thereof as a catalytically active composition in hydroformylation reactions. Said hydroformylactically active compositions comprises, in addition to the complex compounds of metal and the constitutional isomer bisphosphites of formulae (1a) and (2a), non-bound bisphosphites of the constitutional isomer bisphosphites of formulae (1a) and (2a) and at least one additional component.Type: GrantFiled: September 27, 2013Date of Patent: November 22, 2016Assignee: Evonik Degussa GmbHInventors: Andrea Christiansen, Robert Franke, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Bernd Hannebauer
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Patent number: 9464018Abstract: Provided is an industrially advantageous method for producing a dialdehyde having a production ratio of linear dialdehydes to branched dialdehydes of 80/20 to 90/10, with an amount of rhodium to be used that is lower than that in the related art.Type: GrantFiled: March 17, 2014Date of Patent: October 11, 2016Assignee: KURARAY CO., LTD.Inventors: Tatsuya Yoshikawa, Tomoaki Tsuji
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Patent number: 9464019Abstract: A method of managing the heat of a chemical reaction process.Type: GrantFiled: June 18, 2014Date of Patent: October 11, 2016Assignee: Dow Technology Investments LLCInventors: Glenn A. Miller, Irvin B. Cox, Morteza Mokhtarzadeh
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Patent number: 9382180Abstract: A hydroformylation process that tolerates a high level of methanol in the feed.Type: GrantFiled: November 21, 2013Date of Patent: July 5, 2016Assignee: Dow Technology Investments LLCInventors: Glenn A. Miller, Thomas C. Eisenschmid, Rick B. Watson, Michael A. Brammer, Michael C. Becker
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Patent number: 9272973Abstract: The invention relates to a process for preparing aldehydes having five carbon atoms, in which an input mixture containing 10% by weight to 50% by weight of linear butenes and less than 5% by weight of 1-butene is hydroformylated with synthesis gas in the presence of a catalyst system comprising rhodium and at least one bisphosphite ligand, wherein the hydroformylation is effected in a reactor from which, over an operating period, a cycle gas containing at least a portion of the products and unconverted reactants from the hydroformylation is continuously drawn off and partly condensed, and uncondensed components of the cycle gas are recycled into the reactor, and wherein, after the operating period has expired, the hydroformylation is stopped, the reactor is freed of reaction residues and the hydroformylation is restarted. It is based on the problem of making such a process more economically viable.Type: GrantFiled: September 27, 2013Date of Patent: March 1, 2016Assignee: Evonik Industries AGInventors: Dirk Fridag, Robert Franke, Dieter Hess, Markus Schwarz, Katrin Marie Dyballa, Hans-Gerd Lueken, Bart Hamers, Uwe Ernst
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Patent number: 9126138Abstract: The present application is directed to a method and system for preparing gaseous utility streams from gaseous process streams, particularly, removing oil contamination from such streams prior to use in a dry gas seal. The methods and systems may include at least one kinetic swing adsorption process including pressure swing adsorption, temperature swing adsorption, calcination, and inert purge processes to treat gaseous streams for use in dry gas seals of rotating equipment such as compressors, turbines and pumps and other utilities. The adsorbent materials used include a high surface area solid structured microporous and mesoporous materials.Type: GrantFiled: March 18, 2009Date of Patent: September 8, 2015Assignee: ExxonMobil Upstream Research CompanyInventors: Harry W. Deckman, Preeti Kamakoti, Peter I. Ravikovitch, Bruce T. Kelley, Paul Scott Northrop, Peter C. Rasmussen, Paul Lawrence Tanaka, Martin N. Webster, Wieslaw Jerzy Roth, Edward W. Corcoran
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Patent number: 9108912Abstract: The present invention relates to a process for producing 4-hydroxybutyraldehyde, characterized in that allyl alcohol dissolved in polar solvents is reacted with CO and H2 in the presence of a catalytic system which is formed from a rhodium complex and a cyclobutane ligand which contains at least two trans-coordinated 3 5-dialkylphenylphosphinomethyl groups, with the exclusion of catalysts which contain an aliphatic, araliphatic or cycloaliphatic phosphine as ligand.Type: GrantFiled: May 25, 2012Date of Patent: August 18, 2015Assignee: UMICORE AG & CO. KGInventor: Dieter Arlt
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Publication number: 20150141685Abstract: The invention relates to a process for preparing diketonato-rhodium(I)-carbonyl complexes, especially diketonato-rhodium(I)-triorganophosphine-carbonyl complexes, for example Rh(CO)(PPh3)acac. The process according to the invention is a “one-pot synthesis” and features a process procedure without intermediate isolation stages. After introduction of an Rh(III) halide precursor into a solvent and sparging with carbon monoxide (CO), a diketo compound of the R?—C(?O)—CH2—C(?O)—R? type and a base are added, forming the intermediate compound diketonato-Rh(CO)2. After addition of a triorganophosphine of the PR3 type, the reaction mixture is heated and the diketonatocarbonyltriorganophosphine-rhodium(I) complex is removed. The process enables a rapid operation and a high yield. The complex Rh(CO)(PPh3)acac prepared in accordance with the invention, because of its purity, is particularly suitable as a catalyst or precatalyst for homogeneous catalysis, for example for hydroformylation reactions.Type: ApplicationFiled: April 25, 2013Publication date: May 21, 2015Inventors: Eileen Woerner, Timo Ebert, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Juergen Widmer
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Patent number: 9012661Abstract: Organophosphorus compounds, catalytic systems comprising a metallic element forming a complex with the organophosphorus compounds and methods of hydrocyanation and of hydroformylation employed in the presence of the catalytic systems are described.Type: GrantFiled: March 5, 2010Date of Patent: April 21, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Sergio Mastroianni, Igor Mikhel, Paul Pringle
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Patent number: 8998593Abstract: A fluid end assembly including a pump housing with a number of interior passages for the flow of fluids. The housing has a plunger bore with a closed inner end and an open outer end. A suction passage intersects the plunger bore. A discharge passage intersects both the plunger bore and the suction passage such that the discharge passage, the suction passage, and the plunger bore radiate outwardly from their point of intersection to define a shape resembling a “Y”. A connector passage branches from the discharge passage. An outlet passage intersects the connector passage and passes through the pump housing at right angles to the plunger bore. A reciprocating plunger is located in the plunger bore. A suction valve is located in the suction passage. A discharge valve is located in the discharge passage. A fluid supply manifold is pivotally secured to the housing and is in fluid communication with the suction passage.Type: GrantFiled: February 24, 2010Date of Patent: April 7, 2015Assignee: J-Mac Tool, Inc.Inventor: Berton L. Vicars
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Patent number: 8969628Abstract: The invention relates to a method for enriching a homogenous catalyst from a process flow comprising said homogenous catalyst as a component, wherein the process flow is conducted over at least one membrane and wherein the membrane wholly or partially comprises a polymer that has planar polymer units connected to one another via a rigid link and wherein the linker is contorted, such that at least one planar polymer unit is connected to at least one second planar polymer unit via the link, in a non-co-planar arrangement. The invention furthermore relates to a method for producing tridecanal.Type: GrantFiled: February 23, 2010Date of Patent: March 3, 2015Assignee: Evonik Degussa GmbHInventors: Markus Priske, Goetz Baumgarten, Hans-Gerd Lueken, Alfred Kaizik, Klaus-Diether Wiese, Uwe Ernst, Patrick Muhlack
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Patent number: 8927776Abstract: The invention relates to a method for hydroformylation of unsaturated compounds such as olefins and alkynes using mixtures of synthesis gas (CO/H2), in which either the unsaturated compounds and a catalyst are heated to a reaction temperature of 60 to 200° C. and the synthesis gas is then added, or the unsaturated compounds and the catalyst are brought into contact with pure CO at normal temperature in a preformation step, then are heated to reaction temperature and on reaching the reaction temperature the CO is replaced by the synthesis gas. The pressure is 1 to 200 bar and the CO:H2 ratio in the synthesis gas is in the range from 1:1 to 50:1. The iridium catalyst used comprises a phosphorus-containing ligand in the iridium:ligand ratio in the range from 1:1 to 1:100. With high catalyst activities and low catalyst use, very high turnover frequencies are achieved.Type: GrantFiled: October 24, 2011Date of Patent: January 6, 2015Assignee: Evonik Degussa GmbHInventors: Robert Franke, Matthias Beller, Ralf Jackstell, Reiko Jennerjahn, Irene Piras
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Patent number: 8921607Abstract: Mixed butene streams containing butene-1 and isobutylene and optionally butene-2 are hydroformylated under conditions that hydroformylates all the monomers to yield a mixture of valeraldehydes. Higher temperatures and/or longer residence times and/or higher partial pressure of carbon monoxide than in conventional processes are used to ensure hydroformylation of all the monomers.Type: GrantFiled: April 4, 2012Date of Patent: December 30, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael F. Caers, Eddy Theophile Van Driessche, Hubertus J. Beckers, Luc Roger Marc Martens, Georges Marie Mathys, John Richard Shutt
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Patent number: 8921608Abstract: Industrially relevant product selectivities and reaction rates are obtained from rhodium catalyzed hydroformylation of propylene via the use of a novel induction period in which the supramolecular ligand assembly, the rhodium precatalyst and an initial substrate are allowed to form a hydroformylation catalyst that is more selective toward branched aldehydes. Upon heating this incubated mixture and addition of propylene, iso-butyraldehyde is obtained in higher concentrations and rates that are otherwise unattainable.Type: GrantFiled: March 15, 2013Date of Patent: December 30, 2014Assignee: Eastman Chemical CompanyInventors: David William Norman, Elaine Beatrice Mackenzie
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Publication number: 20140350305Abstract: Disclosed is an improved exothermic hydroformylation process having at least two reaction stages. Cooling is provided by externally cooling a stream of reaction mixture from one of the stages, dividing the cooled stream into at least two cooled reaction mixture streams; transferring one cooled reaction mixture stream back into the same reaction stage from which it was removed to cool the reaction mixture in that reaction stage; and transferring at least one cooled reaction mixture stream(s) into and through heat exchange means that cool a different reaction stage, and returning it to the same reaction stage from which it was removed.Type: ApplicationFiled: October 24, 2012Publication date: November 27, 2014Inventors: Michael C. Becker, James D. Duston, Victoria L. Biedenstein, Steven H. Fisher, Glenn A. Miller
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Patent number: 8889916Abstract: The present invention relates to a catalyst composition for hydroformylation reaction and a hydroformylation process using the same. In the hydroformylation process using the catalyst composition according to the present invention, increased catalytic stability and high catalytic activity can be obtained, and the selectivity of iso-aldehyde produced can be desirably controlled.Type: GrantFiled: July 28, 2011Date of Patent: November 18, 2014Assignee: LG Chem, Ltd.Inventors: Jae-Hui Choi, Dong-Hyun Ko, O-Hak Kwon, Sung-Shik Eom, Moo-Ho Hong, Hye-Won Yang
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Patent number: 8889917Abstract: The present invention relates to a method of supplementing the catalyst in continuous hydroformylation during ongoing operation.Type: GrantFiled: April 11, 2013Date of Patent: November 18, 2014Assignee: BASF SEInventors: Edgar Zeller, Armin Ulonska, Arthur Höhn, Volker Uhrig, Rene Magnie, Reimund Fattler