Hydroformylation By Reacting Ethylenically Unsaturated Compound, Carbon Monoxide, And Gaseous Hydrogen Patents (Class 568/451)
  • Patent number: 11027266
    Abstract: The compound of the formula (1) and its complexes with metal cations are used for catalysis in hydroformylation processes.
    Type: Grant
    Filed: November 7, 2017
    Date of Patent: June 8, 2021
    Assignee: EVONIK OPERATIONS GMBH
    Inventor: Robert Franke
  • Patent number: 11008275
    Abstract: The invention relates to a process for preparing carboxylic acids or salts thereof by hydrolysis or saponification of an ester, which is obtained by alkoxycarbonylation of a C2 to C20 hydrocarbon having at least one multiple bond, preferably having at least one olefinic double bond, in which the homogeneous catalyst system used is separated from the product mixture by means of membrane separation. In a development of the present invention, the ester thus formed is converted into another ester by transesterification and then hydrolyzed or saponified.
    Type: Grant
    Filed: June 5, 2020
    Date of Patent: May 18, 2021
    Assignee: Evonik Operations GmbH
    Inventors: Peter Kucmierczyk, Robert Franke, Dirk Fridag, Johannes Knossalla, Marc Schäpertöns, Frederik Gluth
  • Patent number: 10843992
    Abstract: In one aspect, a hydroformylation reaction process comprises contacting an olefin, hydrogen, and CO in the presence of a homogeneous catalyst in a cylindrical reactor to provide a reaction fluid, wherein the reactor has a fixed height, and wherein a total mixing energy of at least 0.5 kW/m3 is delivered to the fluid in the reactor; removing a portion of the reaction fluid from the reactor; and returning at least a portion of the removed reaction fluid to the reactor, wherein the returning reaction fluid is introduced in at least two return locations positioned at a height that is less than 80% of the fixed height, wherein the at least two return locations are positioned above a location in the reactor where hydrogen and carbon monoxide are introduced to the reactor, and wherein at least 15% of the mixing energy is provided by the returning reaction fluid.
    Type: Grant
    Filed: June 19, 2018
    Date of Patent: November 24, 2020
    Assignee: Dow Technology Investments LLC
    Inventors: Michael C. Becker, Donald L. Campbell, Irvin B. Cox, Shankhadeep Das, Seshadri Kumar, Glenn A. Miller, Nilesh Parmar, George R. Phillips
  • Patent number: 10562833
    Abstract: The present invention relates to a method for preparing saturated Cn- and C2n-alcohols, wherein the ratio of Cn- to C2n-alcohols is controlled by a distillative separation of the aldehydes used.
    Type: Grant
    Filed: November 29, 2018
    Date of Patent: February 18, 2020
    Assignee: Evonik Degussa GmbH
    Inventors: Dirk Fridag, Robert Franke, Michael Grass, Florian Boeck, Corinna Hecht, Benedikt Dercks, Udo Lenz, Christoph Hiller, Christoph Ehlers, Stefan Münzner
  • Patent number: 10501392
    Abstract: The present invention relates to a method for preparing saturated Cn- and C2n-alcohols, wherein the ratio of Cn- to C2n-alcohols is controlled by the diversion of substreams in individual method steps.
    Type: Grant
    Filed: November 29, 2018
    Date of Patent: December 10, 2019
    Assignee: Evonik Degussa GmbH
    Inventors: Dirk Fridag, Robert Franke, Michael Grass, Florian Boeck, Corinna Hecht, Benedikt Dercks, Udo Lenz, Christoph Hiller, Christoph Ehlers, Stefan Münzner
  • Patent number: 10479750
    Abstract: A method of producing 1,5-pentanedial having an alkyl group at the 3-position, including a step of hydroformylating an aldehyde compound represented by the following general formula (1): wherein R1 represents an alkyl group having from 1 to 6 carbon atoms.
    Type: Grant
    Filed: February 23, 2017
    Date of Patent: November 19, 2019
    Assignee: KURARAY CO., LTD.
    Inventors: Takuo Tsuruta, Naoya Minamoto, Toshihiro Omatsu
  • Patent number: 10300472
    Abstract: The present invention relates to a catalyst composition including a phosphorous-based ligand, and a hydroformylation method using the catalyst composition. More particularly, the present invention relates to a catalyst composition, which includes two different kinds of monocoordinated phosphine ligands and a transition metal catalyst, and a hydroformylation method using the catalyst composition. In accordance with the present invention, a catalyst composition lowering a selection ratio of normal aldehyde to iso aldehyde (n/i ratio), which are generated during hydroformylation of an olefinic compound, and exhibiting superior catalytic activity and stability, and a method of hydroformylating an olefinic compound using the catalyst composition are provided.
    Type: Grant
    Filed: October 4, 2016
    Date of Patent: May 28, 2019
    Assignee: LG CHEM, LTD.
    Inventors: Min Ji Choi, Mi Young Kim, Sung Shik Eom, Dong Hyun Ko, Da Won Jung, Tae Yun Kim
  • Patent number: 10155710
    Abstract: The present invention relates to integrated processes for using hydroformylation reaction strategies to efficiently convert ethylene in ethylene feed mixtures into C3 products (i.e., products comprising 3 carbon atoms) such as propionaldehyde, 1-propanol, propylene, propanoic acid, and the like. An aspect of the present invention is to partially purify a feed comprising an ethane/ethylene mixture rather than to attempt more complete purification. In contrast to substantially complete purification of ethylene, partial purification is technically and economically feasible at lower cost and allows hydroformylation to be practiced at high productivity and with a lower hydrogen and CO requirement. The lower volumes of such syngas used in the hydroformylation reaction, as well as a more favorable profile of leftover reactants in following hydroformylation makes recycle strategies much easier to practice.
    Type: Grant
    Filed: November 22, 2017
    Date of Patent: December 18, 2018
    Assignee: DP&PL LLC SERIES B
    Inventors: Brian T. Keen, Peter M. Loggenberg, Donald C. Power
  • Patent number: 10155200
    Abstract: The invention deals with the separation of homogeneous catalysts from reaction mixtures with the help of organophilic nanofiltration. It is based on the object of indicating an option as to how organophilic nanofiltration can be used economically for separating off homogeneous catalysts from reaction mixtures if the separation-active material of the membrane satisfying the separation aim is not available in sufficiently large amounts or only at high cost. This object is achieved by taking into consideration a particular membrane performance indicator during the design and/or the execution of the corresponding membrane separation process.
    Type: Grant
    Filed: February 10, 2016
    Date of Patent: December 18, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Frank Geilen, Robert Franke, Bart Hamers
  • Patent number: 10131608
    Abstract: A hydroformylation process wherein a water-soluble amine is contacted with the reaction fluid, liquid from the reactor is sent to an extraction zone, and a neutralized phosphorus acidic compound is at least partially removed from the extraction zone.
    Type: Grant
    Filed: March 10, 2015
    Date of Patent: November 20, 2018
    Assignee: Dow Technology Investments LLC
    Inventors: Glenn A. Miller, Thomas C. Eisenschmid, Michael A. Brammer, Michael C. Becker, Rick B. Watson
  • Patent number: 10017443
    Abstract: The invention relates to a method for producing alcohols by homogeneously catalyzed hydroformylation of olefins to aldehydes and subsequent hydration of the aldehydes. The invention further relates to a system for carrying out the method. The main focus is on the separation technique for work-up of the hydroformylation mixture. The problem addressed by the invention is that specifying a work-up method for hydroformylation mixtures that utilizes the specific advantages of known separation technologies but at the same time largely avoids the specific disadvantages of said separation technologies. The most important objective is to create a catalyst separation system that is as complete and at the same time conservative as possible and that operates in a technically reliable manner and entails low investment and operating costs. The method should be unrestrictedly suitable for processing the reaction output from oxo systems in “world scale” format.
    Type: Grant
    Filed: February 13, 2014
    Date of Patent: July 10, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Hans-Gerd Lueken, Bart Hamers, Dirk Fridag, Robert Franke, Markus Priske, Dieter Hess, Marc Becker, Markus Rudek
  • Patent number: 9914681
    Abstract: The preparation of high-quality oxo process alcohols from inconstant raw material sources is the technically demanding problem which is addressed by a process for continuously preparing an alcohol mixture, in which an input mixture which contains an olefin and has a composition that changes over time is subjected to an oligomerization to obtain an oligomerizate and at least a portion of the olefin oligomers present in the oligomerizate are hydroformylated with carbon monoxide and hydrogen in a hydroformylation in the presence of a homogeneous catalyst system to give aldehydes, at least some of which are converted to the alcohol mixture by subsequent hydrogenation. The process provides a constant plasticizer quality to be produced over a long production period and, optionally, a higher throughput with the same product quality.
    Type: Grant
    Filed: May 20, 2015
    Date of Patent: March 13, 2018
    Assignee: Evonik Degussa GmbH
    Inventors: Frank Geilen, Katrin Marie Dyballa, Dieter Hess, Stephan Peitz, Robert Franke, Dirk Fridag, Dietrich Maschmeyer, Helene Reeker, Guido Stochniol
  • Patent number: 9896406
    Abstract: A process for preparing 2-methylbutyric acid having a reduced content of 3-methylbutyric acid from the secondary streams obtained in the preparation of pentanoic acids, includes generating a stream enriched with 2-methylbutanal and 3-methyl-butanal. The stream enriched with 2-methylbutanal and 3-methylbutanal of step is reacted with formaldehyde. The reaction with formaldehyde is followed by removal of the organic phase and selective hydrogenation in the presence of a hydrogenation catalyst with hydrogen at elevated temperature and elevated pressure and, after removal of the hydrogenation catalyst, treatment of the hydrogenation output obtained with an oxidizing agent.
    Type: Grant
    Filed: November 14, 2014
    Date of Patent: February 20, 2018
    Assignee: OXEA GMBH
    Inventors: Jens Theuerkauf, Heinz Strutz
  • Patent number: 9856198
    Abstract: The present invention relates to integrated processes for using hydroformylation reaction strategies to efficiently convert ethylene in ethylene feed mixtures into C3 products (i.e., products comprising 3 carbon atoms) such as propionaldehyde, 1-propanol, propylene, propanoic acid, and the like. An aspect of the present invention is to partially purify a feed comprising an ethane/ethylene mixture rather than to attempt more complete purification. In contrast to substantially complete purification of ethylene, partial purification is technically and economically feasible at lower cost and allows hydroformylation to be practiced at high productivity and with a lower hydrogen and CO requirement. The lower volumes of such syngas used in the hydroformylation reaction, as well as a more favorable profile of leftover reactants in following hydroformylation makes recycle strategies much easier to practice.
    Type: Grant
    Filed: December 8, 2015
    Date of Patent: January 2, 2018
    Inventors: Brian T. Keen, Peter M. Loggenberg, Donald C. Power
  • Patent number: 9834505
    Abstract: A process of stabilizing a bidentate or tridentate phosphorus-based phosphite ester ligand or mixture thereof in a hydrocyanation reaction milieu comprising water, wherein the ligand or ligand mixture comprises one or more of (i) a bidentate biphosphite ligand of formula (III), (R12—X12) (R13—X13) P—X14—Y—X24—P(X22—R22) (X23—R23) or (ii) a tridentate triphosphite ligand of formula (IIIA) (R12—X12) (R13—X13) P—X14—Y—X32—P(X34—R34)—(X33—Y2—R24—P(X23—R23)—(X22—R22) where each X is oxygen or a bond and each Y is an optionally substituted C6-C20 arylene group, comprising admixing the bidentate and/or tridentate with a stabilizing amount of one or more monodentate phosphite ligand of formula P(X1—R1)(X2—R2)(X3—R3) where each X is oxygen or a bond, wherein the monodentate ligand has a rate of hydrolysis greater than the rate of hydrolysis of the bidentate or tridentate ligand in the presence of water in a hydrocyanation reaction milieu, and thereby preserve concentrations and proportions of the bidentate and/or trid
    Type: Grant
    Filed: May 24, 2013
    Date of Patent: December 5, 2017
    Assignee: INVISTA NORTH AMERICA S.A.R.L.
    Inventors: Sudhir Aki, William J. Tenn, III, Thomas E. Vos
  • Patent number: 9676685
    Abstract: A process for reducing the diene content of an olefin by feeding hydrogen to the process in stages.
    Type: Grant
    Filed: June 19, 2014
    Date of Patent: June 13, 2017
    Assignee: Dow Technology Investments LLC
    Inventors: Rick B. Watson, Glenn A. Miller
  • Patent number: 9573870
    Abstract: A heterocyclic nitrogen stabilizing agent is employed to reduce the rate of catalyst deactivation in a hydroformylation process.
    Type: Grant
    Filed: March 7, 2014
    Date of Patent: February 21, 2017
    Assignee: Dow Technology Investments LLC
    Inventor: Thomas C. Eisenschmid
  • Patent number: 9517995
    Abstract: A process for preparing isomeric hexanoic acids comprising 2-methylpentanoic acid from the secondary streams obtained in the preparation of pentanals, characterized in that a) a mixture comprising linear butenes is reacted to give a pentanal mixture; b) the mixture obtained in step a) is separated into a stream enriched with 2-methylbutanal and 3-methyl-butanal, and a stream enriched with n-pentanal; c) the stream enriched with 2-methylbutanal and 3-methylbutanal of step b) is reacted with formaldehyde; d) the reaction mixture obtained after step c) is selectively reacted to give a mixture comprising 2-methylbutanal and isomeric hexanals; e) the reaction mixture is separated into a stream enriched with 2-methylbutanal and a stream enriched with a mixture of isomeric hexanals; and f) the mixture of isomeric hexanals obtained in step e) is oxidized to a mixture of isomeric hexanoic acids comprising 2-methylpentanoic acid.
    Type: Grant
    Filed: November 14, 2014
    Date of Patent: December 13, 2016
    Assignee: OXEA GMBH
    Inventors: Jens Theuerkauf, Heinz Strutz
  • Patent number: 9517991
    Abstract: A process for preparing 2-methylbutanal from the secondary streams obtained in the preparation of mixtures of isomeric ?,?-unsaturated decenals, characterized in that a) a mixture comprising linear butenes is reacted in the presence of transition metal compounds of group VIII of the Periodic Table of the Elements with carbon monoxide and hydrogen at elevated temperature and elevated pressure to give a pentanal mixture; b) the pentanal mixture obtained in step a) is converted in the presence of basic compounds to a mixture of isomeric ?,?-unsaturated decenals; and c) the mixture obtained in step b) is separated into a stream enriched with unconverted 2-methylbutanal and a stream enriched with a mixture of isomeric ?,?-unsaturated decenals; with the proviso that the stream which has been separated off in step c) and is enriched with unconverted 2-methylbutanal is reacted with formaldehyde.
    Type: Grant
    Filed: November 14, 2014
    Date of Patent: December 13, 2016
    Assignee: OXEA GMBH
    Inventors: Jens Theuerkauf, Heinz Strutz
  • Patent number: 9499505
    Abstract: The subject invention is related to a process for the epoxidation of olefin with peroxide, comprising reacting peroxide with olefin in the presence a solvent, wherein the solvent has Hansen Solubility Parameters (HSPs) of ?T,solvent and ?H,solvent and the epoxide product has Hansen Solubility Parameters (HSPs) of ?T,product and ?H,product, and wherein: ?T,product?6??T,solvent??T,product+6, and ?H,product?6??H,solvent.
    Type: Grant
    Filed: September 17, 2015
    Date of Patent: November 22, 2016
    Assignee: Chang Chun Plastics Co., Ltd.
    Inventors: Sung-Kuang Chung, Ping-Chieh Wang, An-Pang Tu, Kuen-Yuan Hwang
  • Patent number: 9393537
    Abstract: The invention relates to a device for the continuous, homogeneous-catalysis reaction of a liquid with a gas and optionally an additional fluid, wherein the device comprises at least one reactor having an external liquid circulation driven by a pump, and wherein the device has at least one membrane separation stage that preferably holds back the homogeneous catalyst. The aim of the invention is to specify a device that allows homogeneous-catalysis gas/liquid phase reactions, in particular hydroformylations, which operate with membrane separation of the catalyst to be performed economically at an industrially relevant scale. Said aim is achieved in that a jet loop reactor is provided as the reactor, and that the pump and the membrane separation stage are arranged in the same external liquid circuit.
    Type: Grant
    Filed: July 28, 2015
    Date of Patent: July 19, 2016
    Assignee: EVONIK DEGUSSA GmbH
    Inventors: Bart Hamers, Dirk Fridag, Robert Franke, Marc Becker, Markus Priske
  • Patent number: 9149780
    Abstract: The invention relates to a device for the continuous, homogeneous-catalysis reaction of a liquid with a gas and optionally an additional fluid, wherein the device comprises at least one reactor having an external liquid circulation driven by a pump, and wherein the device has at least one membrane separation stage that preferably holds back the homogeneous catalyst. The aim of the invention is to specify a device that allows homogeneous-catalysis gas/liquid phase reactions, in particular hydroformylations, which operate with membrane separation of the catalyst to be performed economically at an industrially relevant scale. Said aim is achieved in that a jet loop reactor is provided as the reactor, and that the pump and the membrane separation stage are arranged in the same external liquid circuit.
    Type: Grant
    Filed: September 7, 2012
    Date of Patent: October 6, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Bart Hamers, Dirk Fridag, Robert Franke, Marc Becker, Markus Priske
  • Patent number: 9115069
    Abstract: In the hydroformylation of olefins having 6 to 20 carbon atoms in the presence of a cobalt catalyst in the presence of an aqueous phase with thorough mixing in a reactor, a hydroformylation products-containing first stream is withdrawn at the top of the reactor and an aqueous phase-containing second stream is withdrawn from the bottom of the reactor. The flow rate of the second stream is controlled in accordance with a temperature which is measured at a point in the bottom of the reactor or in a line leading out of the bottom of the reactor. The yield of crude hydroformylation product is increased as a result of stable sustained operation.
    Type: Grant
    Filed: November 17, 2014
    Date of Patent: August 25, 2015
    Assignee: BASF SE
    Inventors: Rainer Papp, Jens Rudolph, Hans-Günter Thelen, Klaus Diehl
  • Patent number: 9102606
    Abstract: A method for producing a branched chain aldehyde, comprising: reacting an aliphatic olefin having a double bond at an end with carbon monoxide and hydrogen using an iodide of a Group 9 metal as a catalyst and at least one or more selected from the group consisting of hydrogen iodide and alkyl iodides as a promoter.
    Type: Grant
    Filed: May 8, 2013
    Date of Patent: August 11, 2015
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventor: Masaki Sugita
  • Publication number: 20150141702
    Abstract: In the hydroformylation of olefins having 6 to 20 carbon atoms in the presence of a cobalt catalyst in the presence of an aqueous phase with thorough mixing in a reactor, a hydroformylation products-containing first stream is withdrawn at the top of the reactor and an aqueous phase-containing second stream is withdrawn from the bottom of the reactor. The flow rate of the second stream is controlled in accordance with a temperature which is measured at a point in the bottom of the reactor or in a line leading out of the bottom of the reactor. The yield of crude hydroformylation product is increased as a result of stable sustained operation.
    Type: Application
    Filed: November 17, 2014
    Publication date: May 21, 2015
    Inventors: Rainer Papp, Jens Rudolph, Hans-Günter Thelen, Klaus Diehl
  • Patent number: 9029608
    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: Grant
    Filed: May 12, 2014
    Date of Patent: May 12, 2015
    Assignee: 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: 9012694
    Abstract: The present invention provides a process for the production of aldehydes and/or alcohols, which process comprises the steps of: (a) reacting an oxygenate and/or olefinic feed in a reactor in the presence of a molecular sieve catalyst to form an effluent comprising olefins, comprising propylene; (b) separating the effluent comprising olefins as obtained in step (a) into at least a first olefinic product fraction comprising propylene and a second olefinic product fraction; (c) subjecting at least part of the first olefinic product fraction as obtained in step (b) to a hydroformylation process to form aldehydes; (d) separating at least part of the aldehydes as obtained in step (c) into at least a first product fraction of aldehydes and a second product fraction of aldehydes; and (e) hydrogenating at least part of the aldehydes in the first and/or second product fraction of aldehydes as obtained in step (d) to form a first product fraction of alcohols and/or a second product fraction of alcohols; (f) recycling at
    Type: Grant
    Filed: December 21, 2012
    Date of Patent: April 21, 2015
    Assignee: Shell Oil Company
    Inventors: Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
  • Publication number: 20150087864
    Abstract: A method for producing a branched chain aldehyde, comprising: reacting an aliphatic olefin having a double bond at an end with carbon monoxide and hydrogen using an iodide of a Group 9 metal as a catalyst and at least one or more selected from the group consisting of hydrogen iodide and alkyl iodides as a promoter.
    Type: Application
    Filed: May 8, 2013
    Publication date: March 26, 2015
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventor: Masaki Sugita
  • 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
  • Publication number: 20150045586
    Abstract: The present invention provides a process for the production of aldehydes and/or alcohols, which process comprises the steps of: (a) reacting an oxygenate and/or olefinic feed in a reactor in the presence of a molecular sieve catalyst to form an effluent comprising olefins, comprising propylene; (b) separating the effluent comprising olefins as obtained in step (a) into at least a first olefinic product fraction comprising propylene and a second olefinic product fraction; (c) subjecting at least part of the first olefinic product fraction as obtained in step (b) to a hydroformylation process to form aldehydes; (d) separating at least part of the aldehydes as obtained in step (c) into at least a first product fraction of aldehydes and a second product fraction of aldehydes; and (e) hydrogenating at least part of the aldehydes in the first and/or second product fraction of aldehydes as obtained in step (d) to form a first product fraction of alcohols and/or a second product fraction of alcohols; (f) recycling at
    Type: Application
    Filed: December 21, 2012
    Publication date: February 12, 2015
    Inventors: Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
  • Patent number: 8933275
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes processing acetylene as an intermediate stream to form a stream having oxygenates. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to oxygenates through subsequent reactors.
    Type: Grant
    Filed: June 11, 2013
    Date of Patent: January 13, 2015
    Assignee: UOP LLC
    Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
  • 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
  • Publication number: 20140343327
    Abstract: The invention relates to a device for the continuous, homogeneous-catalysis reaction of a liquid with a gas and optionally an additional fluid, wherein the device comprises at least one reactor having an external liquid circulation driven by a pump, and wherein the device has at least one membrane separation stage that preferably holds back the homogeneous catalyst. The aim of the invention is to specify a device that allows homogeneous-catalysis gas/liquid phase reactions, in particular hydroformylations, which operate with membrane separation of the catalyst to be performed economically at an industrially relevant scale. Said aim is achieved in that a jet loop reactor is provided as the reactor, and that the pump and the membrane separation stage are arranged in the same external liquid circuit.
    Type: Application
    Filed: September 7, 2012
    Publication date: November 20, 2014
    Applicant: Evonik Degussa GmbH
    Inventors: Bart Hamers, Dirk Fridag, Robert Franke, Marc Becker, Markus Priske
  • 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: 8871985
    Abstract: The disclosure generally relates to a process for the production of a C6-C15 alcohol mixture including the steps of hydroformylating an olefin mixture including at least one branched C5-C14 olefin to form a hydroformylation product including aldehydes and formates; feeding the hydroformylation product into a hydrogenation step including contacting, in at least one first hydrogenation reactor, at least one catalyst, water, hydrogen, and the hydroformylation product to convert the hydroformylation product to a C6-C15 alcohol mixture; wherein the hydrogen is supplied from the decomposition of the formates and at least one source external to the at least one first hydrogenation reactor.
    Type: Grant
    Filed: January 19, 2011
    Date of Patent: October 28, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Arie Van Vliet, Eddy T. Van Driessche
  • Publication number: 20140309423
    Abstract: The subject matter of the present invention is a plurality of products and the use thereof as a catalytically active composition in a method for producing aldehydes.
    Type: Application
    Filed: October 24, 2012
    Publication date: October 16, 2014
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Andrea Christiansen, Robert Franke, Dirk Fridag, Dieter Hess, Burkard Kreidler, Detlef Selent, Armin Boerner
  • Patent number: 8859823
    Abstract: An improved OXO process with converted waste oil recycle includes: (a) hydroformylating an olefin with synthesis gas in a reactor to produce an OXO product as well as by-product waste oil, the by-product waste oil having a lower or higher boiling temperature than said OXO product; (b) separating OXO product from the by-product waste oil; (c) converting separated waste oil to synthesis gas; and (d) recycling the synthesis gas produced in step (c) to the reactor of step (a).
    Type: Grant
    Filed: June 8, 2012
    Date of Patent: October 14, 2014
    Assignee: Oxea Corporation
    Inventors: Christopher John Bischoff, Chessley Alan Hungerford, Mark Henry Sprow
  • Publication number: 20140296570
    Abstract: The invention relates to a process for converting hydrocarbons into products containing aldehydes and/or alcohols. The invention also relates to producing olefins from the aldehyde and alcohol, to polymerizing the olefins, and to equipment useful for these processes.
    Type: Application
    Filed: December 20, 2011
    Publication date: October 2, 2014
    Applicant: Exxonmobile Chemical Patents Inc.
    Inventors: Paul F. Keusenkothen, Frank Hershkowitz
  • 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
  • Patent number: 8816130
    Abstract: A heterogeneous catalyst that is a combination of rhodium, zinc, iron, a fourth metal and at least one metal selected from alkali metals and alkaline earth metals on a catalyst support (e.g. at least one of silica, alumina, titania, magnesia, zinc aluminate (ZnAl2O4), magnesium aluminate (MgAl2O4), magnesia-modified alumina, zinc oxide-modified alumina, zirconium oxide-modified alumina, and zinc oxide) and use of the catalyst in converting an alkylene to an oxygenate that has one more carbon atom than the alkylene.
    Type: Grant
    Filed: January 12, 2012
    Date of Patent: August 26, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Palanichamy Manikandan, Sreenivasa Rao, Phani Kiran Bollapragada, David G. Barton, Richard M. Wehmeyer, William Tenn, Gerolamo Budroni
  • Patent number: 8791304
    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: Grant
    Filed: July 11, 2011
    Date of Patent: July 29, 2014
    Assignee: 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: 8766014
    Abstract: Convert a mixture of synthesis gas and ethylene to a product stream that contains at least one C3 oxygenate using a supported, heterogeneous catalyst represented by formula RhaAgbSncXdYeOx. In the formula, X is at least one transition element other than rhodium or silver, and Y is at least one element selected from alkali metals and alkaline earth metals.
    Type: Grant
    Filed: September 26, 2011
    Date of Patent: July 1, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Palanichamy Manikandan, Sreenivasa Rao, Phani Kiran Bollapragada
  • Publication number: 20140135534
    Abstract: An improved OXO process with converted waste oil recycle includes: (a) hydroformylating an olefin with synthesis gas in a reactor to produce an OXO product as well as by-product waste oil, the by-product waste oil having a lower or higher boiling temperature than said OXO product; (b) separating OXO product from the by-product waste oil; (c) converting separated waste oil to synthesis gas; and (d) recycling the synthesis gas produced in step (c) to the reactor of step (a).
    Type: Application
    Filed: June 8, 2012
    Publication date: May 15, 2014
    Applicant: Oxea Corporation
    Inventors: Christopher John Bischoff, Chessley Alan Hungerford, Mark Henry Sprow
  • Publication number: 20140135533
    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: Application
    Filed: June 4, 2012
    Publication date: May 15, 2014
    Applicant: LG CHEM, LTD.
    Inventors: Dong-Hyun Ko, Sung-Shik Eom, Moo-Ho Hong, O-Hak Kwon, Jae-Hui Choi, Dae-Chul Kim
  • Patent number: 8673244
    Abstract: The present invention relates to an apparatus for producing alcohols from olefins, comprising: a hydroformylation reactor wherein aldehydes are produced from olefins; a catalyst/aldehydes separator; a hydrogenation reactor wherein the aldehydes are hydrogenated to produce alcohols; and a distillation column. The hydroformylation reactor is equipped with a distributor plate, which has a broad contact surface for providing sufficient reaction area for reactants such as olefins and synthesis gas, and allows the reaction mixture to circulate and mix sufficiently, which contribute to excellent efficiency in terms of production of aldehydes. In addition, the hydrogenation reactor suppresses sub-reactions to improve the production yield of alcohols.
    Type: Grant
    Filed: March 30, 2011
    Date of Patent: March 18, 2014
    Assignee: LG Chem, Ltd.
    Inventors: Dong-Hyun Ko, Sung-Shik Eom, Yong-Jin Choe, Chan-Hong Lee, Moo-Ho Hong, O-Hak Kwon, Dae-Chul Kim, Jae-Hui Choi
  • Publication number: 20140058135
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes processing acetylene as an intermediate stream to form a stream having oxygenates. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to oxygenates through subsequent reactors.
    Type: Application
    Filed: June 11, 2013
    Publication date: February 27, 2014
    Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
  • Publication number: 20140024860
    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: Application
    Filed: October 24, 2011
    Publication date: January 23, 2014
    Applicant: Evonik Oxeno GmbH
    Inventors: Robert Franke, Matthias Beller, Ralf Jackstell, Reiko Jennerjahn, Irene Piras
  • Publication number: 20130331612
    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: July 11, 2011
    Publication date: December 12, 2013
    Inventors: Dong-Hyun Ko, Moo-Ho Hong, Sung-Shik Eom, Yong-Jin Choe, O-Hak Kwon, Dae-Chul Kim, Jae-Hui Choi
  • Patent number: 8586800
    Abstract: A gas phase catalytic hydroformylation process for producing at least one aldehyde product in the presence of a transition metal-ligand complex hydroformylation catalyst and water vapor. Surprisingly, catalyst activity can be sustained by having traces of water vapor in the feed stream. Additionally, additional ligand can be added to replace lost ligand to maintain activity. In addition, it has been found that treatment of the catalyst with a buffer can rejuvenate catalyst activity.
    Type: Grant
    Filed: October 6, 2010
    Date of Patent: November 19, 2013
    Inventor: Richard W. Wegman