Including Hydroformylation Patents (Class 568/882)
  • Patent number: 11136284
    Abstract: Provided is a hydrogenation method of a phthalate compound. According to the present invention, stereoselectivity of the hydrogenation reaction may be increased, and thus the content of a cis isomer in a product may be increased. As a result, quality of the hydrogenation product as a plasticizer may be improved.
    Type: Grant
    Filed: November 1, 2018
    Date of Patent: October 5, 2021
    Assignee: HANWHA SOLUTIONS CORPORATION
    Inventors: Hyo Suk Kim, Ki Taeg Jung, Seong Min Park, Kyoung Il Lee, Hye Won Lee, Jae Heum Jung
  • Patent number: 9988269
    Abstract: The invention provides a method for producing a peroxymonosulfuric acid solution with high stability, including the steps of mixing 35 mass % or more of hydrogen peroxide and 70 mass % or more of sulfuric acid to react them, cooling the reaction solution to 80° C. or lower within five minutes after initiation of the mixing step, and diluting the reaction solution with water four times or more as much as the reaction solution by mass.
    Type: Grant
    Filed: October 1, 2015
    Date of Patent: June 5, 2018
    Assignee: MITSUBISHI GAS CHEMICAL CO., INC.
    Inventors: Kiyoshi Yoshida, Tetsuo Koshitsuka, Kaoru Tsuyuki, Wakana Uesugi
  • Patent number: 9200210
    Abstract: The method for stopping operation of a reactor is provided with a stop step of stopping supply of a synthesis gas containing a carbon monoxide gas and a hydrogen gas into the reactor; a slurry discharge step of discharging slurry from the reactor; a steam supply step of supplying steam higher in temperature than the decomposition temperatures of metal carbonyls into the reactor, thereby discharging gaseous matters inside the reactor; and a carbon monoxide gas detecting step of detecting an amount of carbon monoxide gas contained in the gaseous matters discharged from the reactor. In the steam supply step, supply of the steam is stopped when an amount of the detected carbon monoxide gas continuously declines to be lower than a predetermined reference value.
    Type: Grant
    Filed: March 15, 2012
    Date of Patent: December 1, 2015
    Assignees: Japan Oil, Gas and Metals National Corporation, INPEX CORPORATION, JX Nippon Oil & Energy Corporation, Japan Petroleum Exploration Co., Ltd., COSMO OIL CO., LTD., NIPPON STEEL & SUMIKIN ENGINEERING CO., LTD.
    Inventor: Shinya Arai
  • 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: 9018427
    Abstract: A reactive distillation method comprises introducing a feed stream to a reactive distillation column, contacting the feed stream with one or more catalysts in the reactive distillation column during a distillation, and removing one or more higher alcohols during the distillation from the reactive distillation column as a bottoms stream. The feed stream comprises one or more alpha hydrogen alcohols, and the feed stream reacts in the presence of the one or more catalysts to produce a reaction product comprising the one or more higher alcohols.
    Type: Grant
    Filed: February 18, 2014
    Date of Patent: April 28, 2015
    Assignee: Greenyug, LLC
    Inventors: Sagar B. Gadewar, Brian Christopher Vicente, Peter K. Stoimenov, Vivek Julka
  • 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: 20140350307
    Abstract: Disclosed are an apparatus and method for preparing alcohol from olefin. A reactor for hydroformylating olefin comprises a loop reactor for reducing high-boiling point components, a post-treatment device for separating aldehyde comprises a catalyst/aldehyde separator and a divided wall column (DWC) for removing remaining high-boiling point components, and a post-treatment device for separating alcohol comprises a divided wall column (DWC) for removing remaining high-boiling point components. The apparatus and method for preparing alcohol reduce production of high-boiling point components in the preparation of alcohols and efficiently remove remaining high-boiling point components, thus obtaining alcohol containing no high-boiling point components.
    Type: Application
    Filed: September 26, 2013
    Publication date: November 27, 2014
    Inventors: Sung Shik Eom, Dong Hyun Ko, 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
  • 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: 8680302
    Abstract: Disclosed is a practical method for efficiently producing an alcohol compound by hydrogenating an aldehyde by using a homogeneous copper catalyst which is an easily-available low-cost metal species. Specifically disclosed is a method for producing an alcohol compound, which is characterized in that a hydrogenation reaction of an aldehyde compound is performed in the presence of a homogeneous copper catalyst and a diphosphine compound.
    Type: Grant
    Filed: December 11, 2008
    Date of Patent: March 25, 2014
    Assignee: Takasago International Corporation
    Inventor: Hideo Shimizu
  • 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: 20140051893
    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: Application
    Filed: October 23, 2013
    Publication date: February 20, 2014
    Applicant: 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
  • Patent number: 8604254
    Abstract: Convert an alkylene to a product stream that comprises an alkanol by subjecting a gaseous combination of a) an alkylene selected from ethylene, propylene or a combination thereof, b) carbon monoxide, c) hydrogen and, optionally, d) at least one hydrocarbon or gas diluent other than ethylene or propylene to reductive hydroformylation conditions in combination with a solid phase, sulfided, heterogeneous catalyst.
    Type: Grant
    Filed: November 2, 2010
    Date of Patent: December 10, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: Nancy Kinkade, Richard M. Wehmeyer
  • Patent number: 8569550
    Abstract: A process for the co-production of a stream of a fatty alcohol having first carbon chain lengths and a stream of a fatty alcohol having a second carbon chain lengths, said second carbon chain lengths being longer than said first carbon chain lengths, said process comprising the steps of: (a) supplying a stream comprising lower alkyl esters of fatty acids having chain lengths comprising the first and second chain lengths to a first vaporization zone and contacting said stream with an amount of hydrogen recycled from step (i) which is sufficient to vaporize the lower alkyl esters of the fatty acids having the first carbon chain lengths into the hydrogen; (b) supplying the hydrogen and the vaporized lower alkyl esters of fatty acids having the first carbon chain lengths to a first reaction zone comprising catalyst and operating under reaction conditions to allow hydrogenation to the desired alcohol having first carbon chain lengths; (c) recovering from the first reaction zone an alcohol product stream having fir
    Type: Grant
    Filed: March 30, 2010
    Date of Patent: October 29, 2013
    Assignee: Davy Process Technology Limited
    Inventors: Donald Hugh McKinley, Andrew George Hiles, Rikard Umberto Andersson, John Richard Hensman
  • Patent number: 8541627
    Abstract: An improved hydroformylation catalyst cycle is disclosed wherein the cobalt catalyst is recycled to the hydroformylation reaction mainly as a water soluble carbonyl salt, obtained from extraction of the acidic form of the homogeneous cobalt carbonyl catalyst from the hydroformylation product with an aqueous solution of a salt of a weaker acid. The organic product after extraction is submitted to a further demetalling step in the presence of a dilute acid and an oxidant. The water from this further demetalling step is suitable for use in the upstream extraction step. A free water phase present in the hydroformylation reaction product may be separated upstream from the extraction step and is suitable for use in the further demetalling step, such that the catalyst cycle has no waste water stream.
    Type: Grant
    Filed: August 19, 2009
    Date of Patent: September 24, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Eddy T. A. Van Driessche, Ronald D. Garton, Corey W. Reed
  • Publication number: 20130109890
    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: Application
    Filed: January 19, 2011
    Publication date: May 2, 2013
    Inventors: Arie Van Vliet, Eddy T. Van Driessche
  • Patent number: 8426652
    Abstract: In one embodiment, the invention is to a process for forming an ethanol mixture by hydrogenating an acetaldehyde feed stream in the presence of a catalyst. The acetaldehyde feed stream comprises acetaldehyde and at least one of acetic acid and ethanol. Preferably the acetaldehyde feed stream is a by-product stream from a vinyl acetate synthesis process.
    Type: Grant
    Filed: August 27, 2012
    Date of Patent: April 23, 2013
    Assignee: Celanese International Corporation
    Inventors: Radmila Jevtic, Victor J. Johnston, Lincoln Sarager, R. Jay Warner, Heiko Weiner, Trinity Horton Hale
  • Patent number: 8344186
    Abstract: In one embodiment, the invention is to a process for forming an ethanol mixture by hydrogenating an acetaldehyde feed stream in the presence of a catalyst. The acetaldehyde feed stream comprises acetaldehyde and at least one of acetic acid and ethanol. Preferably the acetaldehyde feed stream is a by-product stream from a vinyl acetate synthesis process.
    Type: Grant
    Filed: October 29, 2010
    Date of Patent: January 1, 2013
    Assignee: Celanese International Corporation
    Inventors: Radmila Jevtic, Victor J. Johnston, Lincoln Sarager, R. Jay Warner, Heiko Weiner, Trinity Horton
  • Patent number: 8124812
    Abstract: An aldehyde composition derived by hydroformylation of a transesterified seed oil and containing a mixture of formyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoformyl, greater than about 1 to less than about 65 percent diformyl, and greater than about 0.1 to less than about 10 percent triformyl-substituted fatty acids or fatty acid esters, and having a diformyl to triformyl weight ratio of greater than about 5/1; preferably, greater than about 3 to less than about 20 percent saturates; and preferably, greater than about 1 to less than about 20 percent unsaturates.
    Type: Grant
    Filed: September 23, 2009
    Date of Patent: February 28, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: Zenon Lysenko, Donald L. Morrison, David A. Babb, Donald L. Bunning, Christopher W. Derstine, James H. Gilchrist, H. Ray Jouett, Jeffrey S. Kanel, Kurt D. Olson, Wei-Jun Peng, Joe D. Phillips, Brian M. Roesch, Aaron W. Sanders, Alan K. Schrock, Pulikkottil J. Thomas
  • Publication number: 20110282108
    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: Application
    Filed: March 30, 2011
    Publication date: November 17, 2011
    Applicant: 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
  • Patent number: 8013192
    Abstract: The invention provides a process for preparing 1,3-alkanediols, such as 1,3-propanediol (PDO), from 3-hydroxyaldehydes, such as 3-hydroxypropanal (HPA), comprising providing a mixture of 3-hydroxyaldehydes in an organic solvent; extracting into an aqueous liquid a major portion of the 3-hydroxyaldehydes to provide an aqueous phase comprising 3-hydroxyaldehydes in greater concentration than the concentration of 3-hydroxyaldehydes in the 3-hydroxyaldehyde mixture, and an organic phase; separating the aqueous phase from the organic phase; contacting the aqueous phase with hydrogen in the presence of a hydrogenation catalyst to provide a hydrogenation product mixture comprising 1,3-alkanediols and water; separating water from the 1,3-alkanediols using a multi-effect evaporation scheme; recycling water containing about 50 wt % or less 1,3-propanediol based upon the total amount of 1,3-propanediol and water to the extraction stage; and recovering 1,3-alkanediols.
    Type: Grant
    Filed: December 4, 2007
    Date of Patent: September 6, 2011
    Assignee: Shell Oil Company
    Inventors: Douglas Lee Husen, Glenn Charles Komplin, Joseph Broun Powell, Paul Richard Weider
  • Patent number: 7910782
    Abstract: In a hydroformylation reaction, the circulation and recovery of cobalt carbonyl in a cobalt catalyst cycle using carbonylate as an intermediate and acidification thereof, is improved by supplying an aqueous sulfuric acid solution containing less than 16% wt of sulfuric acid to the carbonylate to control sulfuric acid concentration in the carbonylate/acid mixture, before accounting for any acid consuming reaction, to a value of from 2% to 10% by weight. Single step and multistage liquid/liquid extraction techniques as well as vapor/liquid extraction techniques followed by the absorption of cobalt from the vapor in an organic liquid both benefit from this improvement.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: March 22, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Eddy T. A. Van Driessche, Arie Van Vliet, Raphael Frans Caers, Hubertus Joseph Beckers, Ronald Dean Garton, Bertrand Raymond Da Cruz, Michel J. P. Lepagnol, Edwin Kooke
  • Publication number: 20100292514
    Abstract: A process for the production of 4-hydroxybutyraldehyde 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 comprising a rhodium complex and a diphosphine. The diphoshine is a trans-1,2 -bis(bis(3,4-di-n-alkylphenyl)phosphinomethyl)cyclobutane and/or a 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,4-di-n-alkylphenyl)phosphino]butane. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.
    Type: Application
    Filed: May 13, 2009
    Publication date: November 18, 2010
    Inventor: Daniel F. White
  • Patent number: 7781620
    Abstract: A hydroformylation process comprising reacting, in a reactor system comprising one or more feed streams, a reaction environment and an output stream, a feedstock composition comprising a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of an organophosphine modified cobalt hydroformylation catalyst, wherein the hydroformylation process is carried out in the reaction environment, which comprises at least two reaction zones, wherein the at least two reaction zones comprise an earlier reaction zone and a later reaction zone, wherein the temperature of the later reaction zone is at a temperature which is at least 2° C. greater than the temperature in the earlier reaction zone, and the temperature of the later reaction zone is in the range of from 140° C. to 220° C., and the temperature of the earlier reaction zone is at least 130° C., and wherein water is added into the reactor system.
    Type: Grant
    Filed: December 19, 2007
    Date of Patent: August 24, 2010
    Assignee: Shell Oil Company
    Inventor: Wilhelmus Petrus Mul
  • Publication number: 20100137630
    Abstract: Acetals are formed from an aldehyde hydrogenation product mixture comprising alcohols and at most 2% of alde-hydes and the product is distilled to yield purified alcohols and a second stream containing acetals and/or unsaturated ethers.
    Type: Application
    Filed: February 27, 2008
    Publication date: June 3, 2010
    Inventors: Ronald Dean Garton, Corey W. Reed, Rao Krishna Kulai, Bruce D. Lilly, Ramzi Yanni Saleh, Raphael Frans Caers
  • Patent number: 7586017
    Abstract: The use of a controlled amount of water in a hydrogenation stage of the oxo process for the production of alcohols which uses at least two reactors in series improves the efficiency of the hydrogenation reaction and catalyst life as does a reduction in the amount of sulphur, chlorine and hydroformylation catalyst residues in the feed to hydrogenation.
    Type: Grant
    Filed: December 16, 2004
    Date of Patent: September 8, 2009
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Eddy Theophyle Andrea Van Driessche, Philippe Louis Buess, Raphael Frans Caers, Arie Van Vliet, Ramzi Yanni Saleh, Jose Manuel Vargas, Kenneth Lloyd Riley, Magdiel Agosto
  • Patent number: 7524997
    Abstract: A hydrogenation catalyst is used for the catalytic hydrogenation of an ester-containing aldehyde mixture and the catalyst contains a ?-alumina having a BET surface area of from 70 to 350 m2/g as support material, and at least one component having hydrogenation activity and being selected from the group consisting of nickel, cobalt and mixtures thereof.
    Type: Grant
    Filed: July 28, 2006
    Date of Patent: April 28, 2009
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Alfred Kaizik, Hans-Gerd Lüken, Michael Grass, Dietrich Maschmeyer, Wilfried Büschken
  • Patent number: 7381852
    Abstract: The present invention relates to a process for hydrogenating an aldehyde. An aldehyde is contacted with a catalyst comprising a support containing at least 95% ?-alumina and non-support metals dispersed on the surface of the support. The non-support metals comprise nickel and/or one or more compounds thereof and molybdenum and/or one or more compounds thereof. The nickel and/or one or more compounds thereof comprise from 3 wt. % to 9 wt. % of the catalyst, by metallic weight, and the molybdenum and/or one or more compounds thereof comprise from 1 wt. % to 4 wt. % of the catalyst, by metallic weight.
    Type: Grant
    Filed: April 11, 2007
    Date of Patent: June 3, 2008
    Assignee: Shell Oil Company
    Inventors: Glenn Charles Komplin, John Anthony Smegal
  • Patent number: 7335800
    Abstract: The present invention provides a hydrogenation catalyst effective for hydrogenating 3-hydroxypropionaldehyde to 1,3-propanediol. The hydrogenation catalyst comprises an ?-alumina support, nickel, ruthenium, and a promoter. The nickel is deposited on the ?-alumina support, and the ruthenium and the promoter are deposited on the nickel and the ?-alumina support. The ?-alumina support comprises at least 92 wt. % of the catalyst, and the nickel comprises from 1 wt. % to 6 wt. % of the catalyst. The present invention also provides a process of hydrogenating 3-hydroxypropionaldehyde to 1,3-propanediol with the catalyst.
    Type: Grant
    Filed: April 21, 2006
    Date of Patent: February 26, 2008
    Assignee: Shell Oil Company
    Inventors: Glenn Charles Komplin, John Anthony Smegal
  • Patent number: 7329783
    Abstract: A hydroformylation process comprising reacting a feedstock composition comprising a compound having at least one olefinic carbon-to-carbon bond with hydrogen and carbon monoxide in the presence of an organophosphine modified cobalt hydroformylation catalyst, wherein the hydroformylation process is carried out in at least two reaction zones, wherein the at least two reaction zones comprise an earlier reaction zone and a later reaction zone, wherein the temperature of the later reaction zone is at least about 2° C. greater than the temperature in the earlier reaction zone, and the temperature of the later reaction zone is in the range of from about 140° C. to about 220° C., and the temperature of the earlier reaction zone is at least about 130° C.
    Type: Grant
    Filed: June 28, 2006
    Date of Patent: February 12, 2008
    Assignee: Shell Oil Company
    Inventor: Wilhelmus Petrus Mul
  • Patent number: 7232934
    Abstract: A reduced or partially reduced nickel-molybdenum catalyst prepared by a process having the steps of 1) reacting nickel carbonate and molybdenum oxide precursors to form nickel molybdate and 2) treating the nickel molybdate under reducing conditions to form the reduced or partially reduced nickel-molybdenum catalyst. There is also a process for making the catalyst. There is also a process for using the catalyst in the hydrogenation of an oxo aldehyde, thereby forming an oxo alcohol of high selectivity. There is also a process for forming an oxo alcohol from the hydroformylation/hydrogenation of an olefinic feedstream. There is also a process for forming an oxo alcohol by contacting formates, dimers, trimers, and organic acids with hydrogen in the presence of a reduced or partially reduced nickel-molybdenum catalyst. The foregoing processes are also useful with a catalyst having the general formula YxZ wherein Y is nickel and/or cobalt and Z is molybdenum and/or tungsten; and wherein x ranges between about 0.
    Type: Grant
    Filed: September 10, 2004
    Date of Patent: June 19, 2007
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Ramzi Yanni Saleh, Stuart L. Soled, Sabato Miseo, Hyung S. Woo
  • Patent number: 7202205
    Abstract: Processes for making particularly branched, especially monomethyl-branched or nongeminal dimethyl-branched surfactants used in cleaning products; preferred processes comprising particular combinations of two or more adsorptive separation steps and, more preferably, particular OXO and/or alkylation steps; products of such processes, including certain modified primary OXO alcohols and/or alkylbenzenes, modified primary OXO alcohol-derived alkoxylated alcohols, alkylsulfates and/or alkoxysulfates; alkylbenzensulfonate surfactants, and consumer cleaning products, especially laundry detergents, containing them. Preferred processes herein more specifically use specific, unconventional sequences of sorptive separation steps to secure certain branched hydrocarbon fractions which are used in further process steps to make olefins useful in OXO processes or as alkylating agents for arenes or for other useful surfactant-making purposes.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: April 10, 2007
    Inventors: Daniel Stedman Connor, Jeffrey John Scheibel, James Charles Theophile Roger Burckett-St. Laurent, Thomas Anthony Cripe, Kevin Lee Kott, Phillip Kyle Vinson
  • Patent number: 7186868
    Abstract: The invention pertains to a hydroformylation process for the conversion of an ethylenically unsaturated compound to an alcohol comprising a first step of reacting at an elevated temperature in a reactor the ethylenically unsaturated compound, carbon monoxide, hydrogen, and a phosphine-containing cobalt hydroformylation catalyst, which are dissolved in a solvent, followed by a second step of separating a mixture comprising the alcohol and heavy ends from a solution comprising the catalyst and the solvent, followed by a third step of recycling the solution to the reactor.
    Type: Grant
    Filed: December 16, 2003
    Date of Patent: March 6, 2007
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Jacoba Catherina Lucia Johanna Suykerbuyk
  • Patent number: 7154012
    Abstract: A process for preparing aliphatic alcohols that includes cobalt-catalyzed hydroformylation of olefins, treatment of a hydroformylation mixture with oxygen-containing gases in the presence of acidic, aqueous cobalt(II) salt solutions, separation of a mixture into an aqueous phase comprising cobalt salts and an organic phase comprising the aliphatic aldehydes, and hydrogenation of an aldehyde-containing organic phase wherein the organic phase and treatment with an adsorbent to separate off cobalt compounds prior to hydrogenation.
    Type: Grant
    Filed: December 8, 2005
    Date of Patent: December 26, 2006
    Assignee: Degussa AG
    Inventors: Hans-Gerd Lueken, Alfred Kaizik, Wilfried Bueschken, Andreas Stenert
  • Patent number: 7138552
    Abstract: The present invention relates to a process for preparing a C13-alcohol mixture which is suitable, in particular, as precursor for the preparation of compounds having surfactant properties and of plasticizers.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: November 21, 2006
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Alfred Kaizik, Walter Tötsch, Wilhelm Droste, Wilfried Büschken, Dirk Röttger, Klaus-Diether Wiese
  • Patent number: 6960699
    Abstract: The invention relates to a process for preparing alcohols by hydroformylation of olefins or olefin mixtures, separation from the catalyst and subsequent hydrogenation, with an extraction being carried out after removal of the catalyst and before the hydrogenation of the aldehydes.
    Type: Grant
    Filed: March 8, 2003
    Date of Patent: November 1, 2005
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Walter Tötsch, Detlef Arnoldi, Alfred Kaizik, Martin Trocha
  • Patent number: 6930213
    Abstract: Acetone is hydrogenated by a process comprising, conducting the liquid-phase hydrogenation of acetone in at least two hydrogenation process stages, thereby preparing isopropanol product with a high selectivity and in high purity.
    Type: Grant
    Filed: July 17, 2000
    Date of Patent: August 16, 2005
    Assignee: Phenolchemie GmbH & Co. KG
    Inventors: Werner Pompetzki, Joachim Schuler, Dietrich Maschmeyer
  • Patent number: 6765119
    Abstract: The invention relates to a process for the preparation of saturated C3-C20-alcohols in which a liquid hydrogenation feed comprising at least one C3-C20-aldehyde is passed over a bed of a hydrogenation catalyst in the presence of a hydrogen-containing gas, which comprises adding to the hydrogenation feed an amount, homogeneously soluble therein, of a salt-like base. The addition of base suppresses side reactions, such as acetalization, aldolization, Tischtschenko reaction or ether formation.
    Type: Grant
    Filed: November 14, 2002
    Date of Patent: July 20, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Herwig Hoffmann, Michael Röper, Heinrich-Josef Blankertz, Max Strohmeyer, Helmut Walz, Helmut Zinke-Allmang
  • Patent number: 6720457
    Abstract: Olefins having from 5 to 24, in particular from 5 to 12, carbon atoms are hydroformylated by reacting an olefin or a mixture of olefins in the presence of an unmodified cobalt catalyst in a single-stage process in a reactor at a temperature of from 100° C. to 220° C. and a pressure of from 100 bar to 400 bar, to obtain an aldehyde, an alcohol or a mixture thereof. An aqueous bottom phase and an organic phase are present in the reactor, the aqueous bottom phase is mixed with the organic phase, and a concentration of the cobalt catalyst, calculated as metallic cobalt, in the aqueous bottom phase is in the range from 0.4 to 1.7% by mass based on the total weight of the aqueous bottom phase. A level of the aqueous bottom phase in the reactor is kept constant during steady-state operation.
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: April 13, 2004
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Stefan Drees, Bernhard Scholz, Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Martin Trocha
  • Publication number: 20030225303
    Abstract: A process for hydroformylating olefinically unsaturated compounds by means of a cobalt-based catalyst is carried out in a non-aqueous ionic liquid which is a liquid at a temperature below 90° C. and comprises at least one ammonium and/or phosphonium and/or sulfonium cation Q+ and at least one anion A−; catalyst recycling is improved by using a ligand selected from the group consisting of Lewis bases and employing a depressurization step between the pressurized reaction step and the step for separating the phases by decanting. At the end of said depressurization step, the organic phase is separated in the decanting step and the non-aqueous ionic liquid containing the catalyst can be re-used.
    Type: Application
    Filed: April 11, 2003
    Publication date: December 4, 2003
    Applicant: Institut Francais du Petrole
    Inventors: Lionel Magna, Helene Olivier-Bourbigou, Lucien Saussine, Virginie Kruger-Tissot
  • Patent number: 6555716
    Abstract: Aldehydes are prepared in a hydroformylation apparatus by the multiphase hydroformylation reaction of one or more olefins with hydrogen and carbon monoxide, where the continuous phase contains a solvent mixture and the hydroformylation catalyst is present in the continuous phase, at least one olefin is present in the dispersed phase, and the loading factor of the tube reactor is greater than or equal to 0.8.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: April 29, 2003
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Büschken, Dirk Röttger
  • Patent number: 6482972
    Abstract: Mixtures of isomeric nonanols and decanols are obtained by joint aldol condensation of n-butanal and pentanals, and up to 1% by weight of 3-methylbutanal, hydrogenation of the aldol condensation product to the corresponding saturated alcohols, and separation from the reaction mixture of the components boiling at temperatures lower than those of the nonanols and decanols. The pentanals are mixtures of 60 to 90% by weight of n-pentanal and 10 to 40% by weight of 2-methylbutanal. The alcohol mixture is especially suitable for preparing ester plasticizers.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: November 19, 2002
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wilfried Fenske, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Müller, Jürgen Szameitat, Ernst Wiebus
  • Patent number: 6455743
    Abstract: A process for producing alcohols, which comprises subjecting a mixture comprising an aldehyde having from 2 to 5 carbon atoms and a polycondensate of the aldehyde at a weight ratio of from 95:5 to 5:95 to a mixing hydrogenation reaction in the presence of a catalyst to produce alcohols corresponding to the aldehydes at the same time wherein substantially no by-product is produced.
    Type: Grant
    Filed: November 26, 1999
    Date of Patent: September 24, 2002
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Akio Ueda, Yuichi Fujita, Atsuhiro Adachi, Hiroki Emoto
  • Patent number: 6444863
    Abstract: A process for producing alcohols, to obtain a straight-chain alcohol having a carbon number of n (where n=3 to 6), a branched chain alcohol having a carbon number of n (where n=3 to 6) and a branched chain alcohol having a carbon number of 2n (where n=3 to 6) from a mixed aldehyde comprising a straight-chain aldehyde having a carbon number of n (where n=3 to 6) and a branched chain aldehyde having a carbon number of n (where n=3 to 6) in an optional proportion, which comprises supplying the mixed aldehyde to a distillation column, withdrawing from the bottom of the column an aldehyde rich in the straight-chain aldehyde, dimerizing the straight-chain aldehyde, followed by hydrogenation to obtain the branched chain alcohol having a carbon number of 2n, while obtaining, as a fraction from the top of the column, an aldehyde rich in the branched chain aldehyde and having a straight-chain aldehyde concentration in the fraction of at least 30 wt %, subjecting the fraction to hydrog
    Type: Grant
    Filed: May 20, 1999
    Date of Patent: September 3, 2002
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Akio Ueda, Atsuhiro Adachi
  • Publication number: 20020019574
    Abstract: A process for producing alcohols, to obtain a straight-chain alcohol having a carbon number of n (where n=3 to 6), a branched chain alcohol having a carbon number of n (where n=3 to 6) and a branched chain alcohol having a carbon number of 2n (where n=3 to 6) from a mixed aldehyde comprising a straight-chain aldehyde having a carbon number of n (where n=3 to 6) and a branched chain aldehyde having a carbon number of n (where n=3 to 6) in an optional proportion, which comprises supplying the mixed aldehyde to a distillation column, withdrawing from the bottom of the column an aldehyde rich in the straight-chain aldehyde, dimerizing the straight-chain aldehyde, followed by hydrogenation to obtain the branched chain alcohol having a carbon number of 2n, while obtaining, as a fraction from the top of the column, an aldehyde rich in the branched chain aldehyde and having a straight-chain aldehyde concentration in the fraction of at least 30 wt %, subjecting the fraction to hydrog
    Type: Application
    Filed: May 20, 1999
    Publication date: February 14, 2002
    Inventors: AKIO UEDA, ATSUHIRO ADACHI
  • Patent number: 6331657
    Abstract: A process for preparing higher oxo alcohols from mixtures of isomeric olefins having from 5 to 24 carbon atoms by two-stage hydroformylation in the presence of a cobalt catalyst or rhodium catalyst at elevated temperature and at elevated pressure, which comprises selectively hydrogenating the first hydroformylation stage reaction mixture, separating the hydrogenation mixture in a distillation into crude alcohol and low-boilers predominantly consisting of olefins, passing these low-boilers to the second hydroformylation stage, again selectively hydrogenating the second hydroformylation stage reaction mixture, separating the hydrogenation mixture in one distillation into crude alcohol and low-boilers, working up the crude alcohol by distillation to pure alcohol and taking off at least some of the low-boilers to discharge saturated hydrocarbons.
    Type: Grant
    Filed: September 15, 1999
    Date of Patent: December 18, 2001
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Alfred Kaizik, Bernhard Scholz, Walter Toetsch, Wilfried Bueschken, Franz Nierlich
  • Patent number: 6278030
    Abstract: An improved process for preparing alcohols by the Oxo process. More particularly this invention relates to an improvement in the hydrogenation step of the Oxo process characterized in the use of certain bulk multimetallic hydrogenation catalysts comprised of at least one Group VIII non-noble metal and at least two Group VIB metals.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: August 21, 2001
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Jose Manuel Vargas, Kenneth Lloyd Riley
  • Patent number: 6239318
    Abstract: The invention relates to a process for the selective hydrogenation of reaction mixtures from the hydroformylation of C5 to C24 olefins using hydrogen and a supported catalyst which, as active components, comprises copper, nickel and chromium.
    Type: Grant
    Filed: September 15, 1999
    Date of Patent: May 29, 2001
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Joachim Schuler, Alfred Kaizik, Bernhard Scholz, Wilfried Bueschken, Wilhelm Droste
  • Patent number: 6232282
    Abstract: A detergent composition containing a mixture of linear alkybenzene sulfonate surfactant and mid-chain branched surfactant and an electrolyte is disclosed. The detergent composition includes a mid-chain branched primary alkyl sulfate surfactant and an electrolyte capable of increasing the ionic strength of the compositions resulting in improved performance, especially under low water temperature wash conditions. Typical electrolytes include sodium chloride, magnesium sulfate, calcium carbonate and the like.
    Type: Grant
    Filed: April 10, 2000
    Date of Patent: May 15, 2001
    Assignee: The Procter & Gamble Company
    Inventors: Frank Andrej Kvietok, Gabor Heltovics, Rinko Katsuda, Phillip Kyle Vinson, Robert Allen Godfroid
  • Patent number: 6232512
    Abstract: Reduction in the content of acetals or ketone acetals in a reaction mixture containing at least 10 moles alcohol per mole acetal or ketone acetal can be achieved hydrogenolytically when the reaction mixture is hydrogenated at 80° to 250° C. at a hydrogen partial pressure of 0.5 to 30 MPa in the presence of activated carbon charged with noble metal as catalyst.
    Type: Grant
    Filed: August 31, 1999
    Date of Patent: May 15, 2001
    Assignee: Degussa-Huls AG
    Inventors: Thomas Haas, Bernd Jäger, Jörg Sauer, Rudolf Vanheertum