Group Va Element (n, P, As, Sb, Or Bi) Containing Material Utilized (e.g., Arsenic Containing Ligand Utilized, Etc.) Patents (Class 568/454)
  • Patent number: 11130725
    Abstract: 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: Grant
    Filed: May 3, 2019
    Date of Patent: September 28, 2021
    Assignee: Dow Technology Investments LLC
    Inventors: Michael A. Brammer, Michael C. Becker, William N. Felsted, II
  • Patent number: 10913055
    Abstract: 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: Grant
    Filed: July 4, 2017
    Date of Patent: February 9, 2021
    Assignee: LG CHEM, LTD.
    Inventors: Mi Young Kim, Sung Shik Eom, Dong Hyun Ko, Da Won Jung, Tae Yun Kim, Min Ji Choi
  • Patent number: 10807934
    Abstract: 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: Grant
    Filed: May 22, 2020
    Date of Patent: October 20, 2020
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Beaven S. Mandimutsira
  • Patent number: 10766839
    Abstract: 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: Grant
    Filed: February 10, 2017
    Date of Patent: September 8, 2020
    Assignee: Dow Technology Investments LLC
    Inventors: Michael C. Becker, Michael A. Brammer, Jason F. Giles, Glenn A. Miller, George R. Phillips, Rick B. Watson, Stephane Wambergue, Martin Lucas Smidt
  • Patent number: 10747292
    Abstract: 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: Grant
    Filed: August 1, 2019
    Date of Patent: August 18, 2020
    Assignee: SHANGHAI CAMBRICON INFORMATION TECHNOLOGY CO., LTD
    Inventors: Shaoli Liu, Lei Zhang, Tianshi Chen
  • Patent number: 10684239
    Abstract: 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: Grant
    Filed: June 30, 2017
    Date of Patent: June 16, 2020
    Assignee: SAUDI ARABIAN OIL COMPANY
    Inventors: Omer Refa Koseoglu, Adnan Al-Hajji, Mohammed Abdullah Al-Ghamdi, Alexander Rebrov
  • Patent number: 10478812
    Abstract: 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: Grant
    Filed: April 13, 2012
    Date of Patent: November 19, 2019
    Assignees: Dow Technology Investments LLC, BASF SE
    Inventors: Thomas C. Eisenschmid, Michael C. Becker, Donald L. Campbell, Jr., Michael A. Brammer, Glenn A. Miller, Edward Adrian Lord, Jens Rudolph, Hans-Rüdiger Reeh
  • Patent number: 10407372
    Abstract: 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: Grant
    Filed: March 15, 2017
    Date of Patent: September 10, 2019
    Assignee: Dow Technology Investments LLC
    Inventors: Kathleen Simpson, Gerald L. Smith
  • Patent number: 10294428
    Abstract: 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: Grant
    Filed: January 26, 2016
    Date of Patent: May 21, 2019
    Assignee: KURARAY CO., LTD.
    Inventors: Takahiro Suzuki, Yuusuke Saitou
  • Patent number: 10119079
    Abstract: 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: Grant
    Filed: March 11, 2015
    Date of Patent: November 6, 2018
    Assignee: KURARAY CO., LTD.
    Inventors: Junichi Fuji, Ryoko Miyazaki, Takahiro Suzuki
  • Patent number: 9908910
    Abstract: 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: Grant
    Filed: December 16, 2016
    Date of Patent: March 6, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Frank Geilen, Galina Morales Torres, Detlef Selent, Armin Börner
  • Patent number: 9896404
    Abstract: 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: Grant
    Filed: December 16, 2016
    Date of Patent: February 20, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Frank Geilen, Galina Morales Torres, Detlef Selent, Armin Börner
  • Patent number: 9765023
    Abstract: Novel complexes of diphenyl selenoxides and also use thereof and methods in which the complexes are used.
    Type: Grant
    Filed: December 7, 2016
    Date of Patent: September 19, 2017
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Robert Franke, Detlef Selent, Armin Börner, Claudia Weilbeer
  • Patent number: 9737884
    Abstract: The catalytic preparation of an aldehyde from an olefin proceeds in the presence of a monophosphite mixture.
    Type: Grant
    Filed: May 19, 2015
    Date of Patent: August 22, 2017
    Assignee: Evonik Degussa GmbH
    Inventors: Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Dieter Hess, Bart Hamers, Frank Geilen
  • Patent number: 9713791
    Abstract: 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: Grant
    Filed: July 25, 2014
    Date of Patent: July 25, 2017
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Markus Priske, Robert Franke, Bart Hamers, Patrick Schmidt, Andrzej Górak
  • Patent number: 9707552
    Abstract: 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: Grant
    Filed: October 19, 2015
    Date of Patent: July 18, 2017
    Assignee: LG CHEM. LTD.
    Inventors: Mi Young Kim, Min Ji Choi, Sung Shik Eom, Dong Hyun Ko, Da Won Jung, Tae Yun Kim
  • Patent number: 9695098
    Abstract: A multi-reactor hydroformylation process wherein a common product-catalyst separation zone is employed.
    Type: Grant
    Filed: December 9, 2014
    Date of Patent: July 4, 2017
    Assignee: DOW TECHNOLOGY INVESTMENTS LLC
    Inventors: Glenn A. Miller, Jason F. Giles, Irvin B. Cox
  • Patent number: 9687837
    Abstract: 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: Grant
    Filed: August 31, 2016
    Date of Patent: June 27, 2017
    Assignee: Eastman Chemical Company
    Inventor: Thomas James Devon
  • Patent number: 9688598
    Abstract: A multi-reaction train hydroformylation process wherein a common product-catalyst separation zone is employed.
    Type: Grant
    Filed: December 9, 2014
    Date of Patent: June 27, 2017
    Assignee: DOW TECHNOLOGY INVESTMENTS LLC
    Inventors: 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
  • Patent number: 9670122
    Abstract: A process of controlling hydroformylation reaction fluid temperature involves controlling the flow rate of reaction fluid through an external heat exchanger.
    Type: Grant
    Filed: September 9, 2014
    Date of Patent: June 6, 2017
    Assignee: Dow Technology Investments LLC
    Inventors: Cloid R. Smith, III, Morteza Mokhtarzadeh, Irvin B. Cox
  • Patent number: 9663434
    Abstract: 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: Grant
    Filed: September 30, 2016
    Date of Patent: May 30, 2017
    Assignee: King Fahd University of Petroleum and Minerals
    Inventors: Mohammed Nasiruzzaman Shaikh, Zain Hassan Yamani
  • Patent number: 9624153
    Abstract: 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: Grant
    Filed: December 10, 2014
    Date of Patent: April 18, 2017
    Assignee: Evonik Degussa GmbH
    Inventors: Marc Becker, Katrin Marie Dyballa, Robert Franke, Dirk Fridag, Hanna Hahn, Marina Lazar, Markus Priske, Guido Stochniol
  • Patent number: 9616422
    Abstract: 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: Grant
    Filed: September 25, 2014
    Date of Patent: April 11, 2017
    Assignee: LG CHEM, LTD.
    Inventors: Sung Shik Eom, Dong Hyun Ko, Da Won Jung, Min Soo Kim, Tae Yun Kim
  • Patent number: 9610574
    Abstract: 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: Grant
    Filed: August 8, 2014
    Date of Patent: April 4, 2017
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Katrin Marie Dyballa, Hanna Hahn, Robert Franke, Dirk Fridag, Marc Becker
  • Patent number: 9611203
    Abstract: 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: Grant
    Filed: December 11, 2013
    Date of Patent: April 4, 2017
    Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES
    Inventors: Yunjie Ding, Li Yan, Miao Jiang, Ronghe Lin
  • Patent number: 9586197
    Abstract: 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: Grant
    Filed: December 11, 2013
    Date of Patent: March 7, 2017
    Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES
    Inventors: Yunjie Ding, Miao Jiang, Li Yan, Ronghe Lin
  • Patent number: 9499463
    Abstract: 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: Grant
    Filed: September 27, 2013
    Date of Patent: November 22, 2016
    Assignee: Evonik Degussa GmbH
    Inventors: Andrea Christiansen, Robert Franke, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Bernd Hannebauer
  • Patent number: 9464019
    Abstract: A method of managing the heat of a chemical reaction process.
    Type: Grant
    Filed: June 18, 2014
    Date of Patent: October 11, 2016
    Assignee: Dow Technology Investments LLC
    Inventors: Glenn A. Miller, Irvin B. Cox, Morteza Mokhtarzadeh
  • Patent number: 9464018
    Abstract: 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: Grant
    Filed: March 17, 2014
    Date of Patent: October 11, 2016
    Assignee: KURARAY CO., LTD.
    Inventors: Tatsuya Yoshikawa, Tomoaki Tsuji
  • Patent number: 9382180
    Abstract: A hydroformylation process that tolerates a high level of methanol in the feed.
    Type: Grant
    Filed: November 21, 2013
    Date of Patent: July 5, 2016
    Assignee: Dow Technology Investments LLC
    Inventors: Glenn A. Miller, Thomas C. Eisenschmid, Rick B. Watson, Michael A. Brammer, Michael C. Becker
  • Patent number: 9272973
    Abstract: 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: Grant
    Filed: September 27, 2013
    Date of Patent: March 1, 2016
    Assignee: Evonik Industries AG
    Inventors: Dirk Fridag, Robert Franke, Dieter Hess, Markus Schwarz, Katrin Marie Dyballa, Hans-Gerd Lueken, Bart Hamers, Uwe Ernst
  • Patent number: 9126138
    Abstract: 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: Grant
    Filed: March 18, 2009
    Date of Patent: September 8, 2015
    Assignee: ExxonMobil Upstream Research Company
    Inventors: 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
  • Patent number: 9108912
    Abstract: 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: Grant
    Filed: May 25, 2012
    Date of Patent: August 18, 2015
    Assignee: UMICORE AG & CO. KG
    Inventor: Dieter Arlt
  • Publication number: 20150141685
    Abstract: 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: Application
    Filed: April 25, 2013
    Publication date: May 21, 2015
    Inventors: Eileen Woerner, Timo Ebert, Ralf Karch, Andreas Rivas-Nass, Angelino Doppiu, Juergen Widmer
  • Patent number: 9012661
    Abstract: 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: Grant
    Filed: March 5, 2010
    Date of Patent: April 21, 2015
    Assignee: INVISTA North America S.a.r.l.
    Inventors: Sergio Mastroianni, Igor Mikhel, Paul Pringle
  • Patent number: 8998593
    Abstract: 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: Grant
    Filed: February 24, 2010
    Date of Patent: April 7, 2015
    Assignee: J-Mac Tool, Inc.
    Inventor: Berton L. Vicars
  • Patent number: 8969628
    Abstract: 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: Grant
    Filed: February 23, 2010
    Date of Patent: March 3, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Markus Priske, Goetz Baumgarten, Hans-Gerd Lueken, Alfred Kaizik, Klaus-Diether Wiese, Uwe Ernst, Patrick Muhlack
  • Patent number: 8927776
    Abstract: 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: Grant
    Filed: October 24, 2011
    Date of Patent: January 6, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Robert Franke, Matthias Beller, Ralf Jackstell, Reiko Jennerjahn, Irene Piras
  • Patent number: 8921608
    Abstract: 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: Grant
    Filed: March 15, 2013
    Date of Patent: December 30, 2014
    Assignee: Eastman Chemical Company
    Inventors: David William Norman, Elaine Beatrice Mackenzie
  • Patent number: 8921607
    Abstract: 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: Grant
    Filed: April 4, 2012
    Date of Patent: December 30, 2014
    Assignee: 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
  • Publication number: 20140350305
    Abstract: 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: Application
    Filed: October 24, 2012
    Publication date: November 27, 2014
    Inventors: Michael C. Becker, James D. Duston, Victoria L. Biedenstein, Steven H. Fisher, Glenn A. Miller
  • Patent number: 8889917
    Abstract: The present invention relates to a method of supplementing the catalyst in continuous hydroformylation during ongoing operation.
    Type: Grant
    Filed: April 11, 2013
    Date of Patent: November 18, 2014
    Assignee: BASF SE
    Inventors: Edgar Zeller, Armin Ulonska, Arthur Höhn, Volker Uhrig, Rene Magnie, Reimund Fattler
  • Patent number: 8889916
    Abstract: 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: Grant
    Filed: July 28, 2011
    Date of Patent: November 18, 2014
    Assignee: LG Chem, Ltd.
    Inventors: Jae-Hui Choi, Dong-Hyun Ko, O-Hak Kwon, Sung-Shik Eom, Moo-Ho Hong, Hye-Won Yang
  • Patent number: 8884071
    Abstract: Disclosed is a hydroformylation method having improved catalyst stability in a reaction. Advantageously, provided is a hydroformylation method in which a specific ?,?-unsaturated carbonyl compound is incorporated during a hydroformylation reaction to prevent alkyl phosphite decomposed from a phosphite ligand from acting as a catalyst poison, thereby improving a yield of reaction and inhibiting decomposition of ligand and catalyst.
    Type: Grant
    Filed: June 4, 2012
    Date of Patent: November 11, 2014
    Assignee: LG Chem, Ltd.
    Inventors: Dong-Hyun Ko, Sung-Shik Eom, Moo-Ho Hong, O-Hak Kwon, Jae-Hui Choi, Dae-Chul Kim
  • Patent number: 8884072
    Abstract: The extraction process for removing metal salts from an organic hydroformylation reaction fluid (“HRF”) prior to returning the HRF to a reaction zone of a hydroformylation process, the extraction process comprising the step of contacting the HRF with an aqueous buffer solution, is improved by contacting the HRF with water in addition to that present in the aqueous buffer solution, i.e., with added water.
    Type: Grant
    Filed: November 3, 2011
    Date of Patent: November 11, 2014
    Assignees: Dow Technology Investments LLC, BASF SE
    Inventors: Glenn A. Miller, Michael A. Brammer, Donald L. Campbell, Jr., Thomas C. Eisenschmid, Adrian Lord, Jens Rudolph, Hans-Rüdiger Reeh, Hans-Günter Thelen, Maximilian Walter
  • Patent number: 8846994
    Abstract: The invention relates to a method for producing low-odor n-butane by catalytic hydrogenation of a feed mixture. The aim of the invention is to provide such a method, wherein the feed material, in addition to n-butane, n-butene and up to 1 mass % formic acid and/or up to 1 mass % pentanals and/or up to 0.5 mass % pentanols, also comprises carbon monoxide. The aim is achieved by treating the feed mixture in the temperature range of 15 to 120° C. with an aqueous solution of an alkali metal or alkaline earth metal hydroxide in the concentration range of 0.5 to 30 mass % and subsequently subjecting the feed mixture to the catalytic hydrogenation.
    Type: Grant
    Filed: May 21, 2010
    Date of Patent: September 30, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Hans-Gerd Lueken, Alfred Kaizik, Markus Winterberg, Wilfried Bueschken, Dirk Fridag
  • Publication number: 20140249333
    Abstract: The present invention relates to an apparatus for coproducting iso-type reaction product and alcohol from olefin, and a method for coproducting using the apparatus, in which the hydroformylation reactor provides a sufficient reaction area due to the broad contact surface area between the olefin and the synthesis gases that are the raw materials by a distributor plate installed in the reactor, and the raw materials can be sufficiently mixed with the reaction mixture due to the circulation of the reaction mixture so that the efficiency of the production of the aldehyde is excellent; and also the hydrogenation reactor suppresses the side reaction so that the efficiency for producing aldehyde and alcohol are all increased, and also iso-type reaction product and alcohol can be efficiently co-produced.
    Type: Application
    Filed: May 12, 2014
    Publication date: September 4, 2014
    Applicant: LG CHEM, LTD.
    Inventors: Dong-Hyun KO, Moo-Ho HONG, Sung-Shik EOM, Yong-Jin CHOE, O-Hak KWON, Dae-Chul KIM, Jae-Hui CHOI
  • Patent number: 8822734
    Abstract: Allyl alcohol, particularly from biobased sources such as glycerol, is hydroformylated to products including 4-hydroxybutyraldehyde and 4-hydroxy-2-methylpropionaldehyde by forming a homogeneous reaction mixture including allyl alcohol, a rhodium-based hydroformylation catalyst and a near critical liquefiable petroleum gas or mixture of such gases, reacting the near critical liquefiable petroleum gas (or gas mixture)-expanded allyl alcohol substrate with carbon monoxide and with hydrogen in the presence of the catalyst, and recovering substantially all of the petroleum gas or gases overhead by reducing the pressure and degassing the product mixture. Dense propane is especially useful as a single inert solvent/diluent, and substantially no other solvent/diluent is needed.
    Type: Grant
    Filed: February 14, 2012
    Date of Patent: September 2, 2014
    Assignee: The University of Kansas
    Inventors: Bala Subramaniam, Raghunath V. Chaudhari, Bibhas Sarkar
  • Patent number: 8791305
    Abstract: The present invention relates to ligands and catalyst systems for the hydroformylation of short and long chain olefins, preferably for the hydroformylation of ally alcohol producing 4-hydroxybutyraldehyde. The ligands disclosed herein are all-trans phosphinomethyl-cyclobutane ligands, such as, for example, all-trans-1,2,3,4-tetra[bis-(3,5-xylyl)phosphinomethyl]-cyclobutane. The catalyst systems comprise these all-trans phosphinomethyl-cyclobutane ligands in combination with an organometallic rhodium complex such as, e.g., (acctylacetonato)-dicarbonyl-rhodium (I). The ligands and catalyst systems of the present invention may be employed in the hydroformylation of olefins, in particular in the hydroformylation of allylalcohol, and provide improved selectivity and high reaction yields.
    Type: Grant
    Filed: May 25, 2012
    Date of Patent: July 29, 2014
    Assignee: Umicore AG & Co. KG
    Inventor: Dieter Arlt
  • Patent number: 8779211
    Abstract: A process for producing 4-hydroxybutyraldehyde comprises reacting allyl alcohol with CO/H2 in a reactor in the presence of a catalyst system comprising rhodium complex and trans-1,2-bis[bis(3,5-di-n-alkylphenyl)phosphino]-cyclobutane at a pressure of about 50 psi or lower.
    Type: Grant
    Filed: May 29, 2013
    Date of Patent: July 15, 2014
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Beaven S. Mandimutsira, Daniel F. White