Supported Hydrogenation Catalyst Utilized Patents (Class 568/883)
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Patent number: 9315436Abstract: The invention relates to nonyl alcohols with a low degree of branching and derivatives produced using them. In particular the present invention relates to mixture of primary nonyl alcohols in which at least 80% of the alkyl chains are linear and at least 15% of the alkyl chains are branched at the 2-carbon position and its derivatives. The low degree of branching produces derivatives that are more elongated and less bulky that similar derivatives produced with more highly branched alcohols.Type: GrantFiled: September 1, 2015Date of Patent: April 19, 2016Assignee: Shell Oil CompanyInventors: Julian Richard Barnes, James Grace Crump, Paul Theodore Sharko
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Patent number: 9029608Abstract: 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: GrantFiled: May 12, 2014Date of Patent: May 12, 2015Assignee: 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
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Patent number: 9018427Abstract: 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: GrantFiled: February 18, 2014Date of Patent: April 28, 2015Assignee: Greenyug, LLCInventors: Sagar B. Gadewar, Brian Christopher Vicente, Peter K. Stoimenov, Vivek Julka
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Patent number: 9012694Abstract: 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 atType: GrantFiled: December 21, 2012Date of Patent: April 21, 2015Assignee: Shell Oil CompanyInventors: Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
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Patent number: 8791304Abstract: 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: GrantFiled: July 11, 2011Date of Patent: July 29, 2014Assignee: 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
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Patent number: 8673244Abstract: 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: GrantFiled: March 30, 2011Date of Patent: March 18, 2014Assignee: 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
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Publication number: 20140051893Abstract: 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: ApplicationFiled: October 23, 2013Publication date: February 20, 2014Applicant: 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
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Patent number: 8604254Abstract: 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: GrantFiled: November 2, 2010Date of Patent: December 10, 2013Assignee: Dow Global Technologies LLCInventors: Nancy Kinkade, Richard M. Wehmeyer
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Patent number: 8471075Abstract: A process for selective formation of ethanol from acetic acid by hydrogenating acetic acid in the presence of first metal, a silicaceous support, and at least one support modifier. Preferably, the first metal is selected from the group consisting of copper, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, titanium, zinc, chromium, rhenium, molybdenum, and tungsten. In addition the catalyst may comprise a second metal preferably selected from the group consisting of copper, molybdenum, tin, chromium, iron, cobalt, vanadium, tungsten, palladium, platinum, lanthanum, cerium, manganese, ruthenium, rhenium, gold, and nickel.Type: GrantFiled: February 2, 2010Date of Patent: June 25, 2013Assignee: Celanese International CorporationInventors: Victor J. Johnston, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, James H. Zink, Heiko Weiner, John L. Potts, Radmila Jevtic
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Patent number: 8426652Abstract: 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: GrantFiled: August 27, 2012Date of Patent: April 23, 2013Assignee: Celanese International CorporationInventors: Radmila Jevtic, Victor J. Johnston, Lincoln Sarager, R. Jay Warner, Heiko Weiner, Trinity Horton Hale
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Patent number: 8344186Abstract: 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: GrantFiled: October 29, 2010Date of Patent: January 1, 2013Assignee: Celanese International CorporationInventors: Radmila Jevtic, Victor J. Johnston, Lincoln Sarager, R. Jay Warner, Heiko Weiner, Trinity Horton
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Publication number: 20110282108Abstract: 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: ApplicationFiled: March 30, 2011Publication date: November 17, 2011Applicant: 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
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Patent number: 7777083Abstract: A process for the reduction of compounds comprising one or more carbon-oxygen (C?0) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at a pressure greater than 3 atm and a catalyst comprising an iridium aminodiphosphine complex.Type: GrantFiled: May 30, 2008Date of Patent: August 17, 2010Assignee: Kanata Chemical Technologies Inc.Inventors: Kamaluddin Abdur-Rashid, Rongwei Guo, Xuanhua Chen, Wenli Jia
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Patent number: 7772445Abstract: The present disclosure relates to a process for the hydrogenation of compounds comprising one or more carbon-oxygen (C?O) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at and a catalyst comprising a ruthenium-aryl-aminophosphine complex.Type: GrantFiled: July 7, 2008Date of Patent: August 10, 2010Assignee: Kanata Chemical Technologies Inc.Inventors: Xuanhua Chen, Wenli Jia, Kamaluddin Abdur-Rashid, Rongwei Guo
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Patent number: 7663006Abstract: A process for producing a purified alcohol giving satisfactory results in a sulfuric acid coloring test is provided. A process for producing a purified alcohol which includes the following steps: a condensation step in which an aldehyde is subjected to aldol condensation and dehydration to obtain the corresponding condensate, a hydrogenation step in which the condensate is hydrogenated to obtain a crude alcohol, and a purification step in which the crude alcohol is distilled to obtain a purified alcohol, characterized in that the crude alcohol in which the concentration of one or more compounds having an oxygen-containing heterocycle having a carbon-carbon double bond in the ring is 200 weight ppm or lower is fed to the purification step. Specifically, the aldehyde is normal butyraldehyde, the condensate is 2-ethylhexenal, and the alcohol is 2-ethylhexanol.Type: GrantFiled: March 14, 2005Date of Patent: February 16, 2010Assignee: Mitsubishi Chemical CorporationInventors: Hirofumi Oota, Hiroki Kawasaki
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Patent number: 7586017Abstract: 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: GrantFiled: December 16, 2004Date of Patent: September 8, 2009Assignee: 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
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Patent number: 7524997Abstract: 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: GrantFiled: July 28, 2006Date of Patent: April 28, 2009Assignee: OXENO Olefinchemie GmbHInventors: Alfred Kaizik, Hans-Gerd Lüken, Michael Grass, Dietrich Maschmeyer, Wilfried Büschken
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Patent number: 7381852Abstract: 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: GrantFiled: April 11, 2007Date of Patent: June 3, 2008Assignee: Shell Oil CompanyInventors: Glenn Charles Komplin, John Anthony Smegal
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Patent number: 7335800Abstract: 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: GrantFiled: April 21, 2006Date of Patent: February 26, 2008Assignee: Shell Oil CompanyInventors: Glenn Charles Komplin, John Anthony Smegal
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Patent number: 7232934Abstract: 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: GrantFiled: September 10, 2004Date of Patent: June 19, 2007Assignee: ExxonMobil Chemical Patents Inc.Inventors: Ramzi Yanni Saleh, Stuart L. Soled, Sabato Miseo, Hyung S. Woo
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Patent number: 7154012Abstract: 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: GrantFiled: December 8, 2005Date of Patent: December 26, 2006Assignee: Degussa AGInventors: Hans-Gerd Lueken, Alfred Kaizik, Wilfried Bueschken, Andreas Stenert
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Patent number: 7138552Abstract: 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: GrantFiled: March 25, 2003Date of Patent: November 21, 2006Assignee: OXENO Olefinchemie GmbHInventors: Alfred Kaizik, Walter Tötsch, Wilhelm Droste, Wilfried Büschken, Dirk Röttger, Klaus-Diether Wiese
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Patent number: 7101824Abstract: The present invention relates to a process for the preparation of iron-doped ruthenium catalysts supported on carbon, and their use for the selective liquid phase hydrogenation of carbonyl compounds to give the corresponding alcohols, in particular for the hydrogenation of citral to give geraniol or nerol or of citronellal to give citronellol.Type: GrantFiled: December 4, 2002Date of Patent: September 5, 2006Assignee: BASF AktiengellsellschaftInventors: Till Gerlach, Hans-Georg Göbbel, Frank Funke, Klaus Ebel, Ekkehard Schwab, Signe Unverricht, Reinhard Körner, Lisa Lobree
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Patent number: 6960699Abstract: 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: GrantFiled: March 8, 2003Date of Patent: November 1, 2005Assignee: Oxeno Olefinchemie GmbHInventors: Walter Tötsch, Detlef Arnoldi, Alfred Kaizik, Martin Trocha
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Patent number: 6930213Abstract: 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: GrantFiled: July 17, 2000Date of Patent: August 16, 2005Assignee: Phenolchemie GmbH & Co. KGInventors: Werner Pompetzki, Joachim Schuler, Dietrich Maschmeyer
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Patent number: 6906228Abstract: In a process for preparing alcohols by catalytic hydrogenation of carbonyl compounds over a catalyst comprising rhenium on activated carbon, the catalyst used comprises rhenium (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5, platinum (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5 and, if appropriate, at least one further metal selected from among Zn, Cu, Ag, Au, Ni, Fe, Ru, Mn, Cr, Mo, W and V in a weight ratio to the activated carbon of from 0 to 0.25, and the activated carbon has been nonoxidatively pretreated It is also possible to prepare ethers and lactones if the hydrogen pressure is not more than 25 bar. In this case, the activated carbon in the catalyst may also have been nonoxidatively pretreated.Type: GrantFiled: March 1, 2001Date of Patent: June 14, 2005Assignee: BASF AGInventors: Rolf Hartmuth Fischer, Rolf Pinkos, Stephan Andreas Schunk, Joachim Wulff-Döring, Frank Stein, Thomas Nöbel, Sylvia Huber
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Patent number: 6841499Abstract: A supported catalyst comprises a cationic rhodium(I) complex of the formula wherein R1 and R2 are the same or different hydrocarbon groups of up to 30 C atoms, or R1 and R2 are linked to form a ring, and a heterogeneous support medium that provides anionic binding sites. Such a complex is particularly useful as a catalyst in a process of hydrogenating an aldehyde to produce the corresponding primary alcohol.Type: GrantFiled: October 6, 2000Date of Patent: January 11, 2005Assignee: Chirotech Technology LimitedInventors: Mark Joseph Burk, Arne Gerlach
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Patent number: 6765119Abstract: 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: GrantFiled: November 14, 2002Date of Patent: July 20, 2004Assignee: BASF AktiengesellschaftInventors: Herwig Hoffmann, Michael Röper, Heinrich-Josef Blankertz, Max Strohmeyer, Helmut Walz, Helmut Zinke-Allmang
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Patent number: 6762332Abstract: A process for the preparation of an alcohol from an olefin wherein the olefin is reacted with syngas in the presence of a catalyst system having a homogeneous hydroformylation catalyst and a heterogeneous catalyst having copper on a support.Type: GrantFiled: November 22, 2002Date of Patent: July 13, 2004Assignee: Shell Oil CompanyInventor: Jean-Paul Lange
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Patent number: 6555716Abstract: 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: GrantFiled: November 30, 2000Date of Patent: April 29, 2003Assignee: Oxeno Olefinchemie GmbHInventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Büschken, Dirk Röttger
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Patent number: 6482972Abstract: 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: GrantFiled: May 8, 1995Date of Patent: November 19, 2002Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wilfried Fenske, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Müller, Jürgen Szameitat, Ernst Wiebus
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Patent number: 6444863Abstract: 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 hydrogType: GrantFiled: May 20, 1999Date of Patent: September 3, 2002Assignee: Mitsubishi Chemical CorporationInventors: Akio Ueda, Atsuhiro Adachi
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Patent number: 6410809Abstract: A process of producing a 1,1-cyclohexanedimethanol compound having a substituent group at the 2-position in which the step of producing a 1-hydroxymethyl-3-cyclohexene-1-carbaldehyde compound by Diels-Alder reaction of a &bgr;-substituted-&agr;,&bgr;-unsaturated aldehyde and a chain conjugated diene compound using an anhydrous tin (IV) halide catalyst is essential and a process of producing productive intermediates therefor. 1,1-Cyclohexanedimethanol compounds having a substituent group at least at the 2-position thereof obtained by the present invention are useful as a raw material for polyesters, unsaturated polyesters, alkyds, polyurethanes, epoxy resins, acrylic resins, etc. and as raw materials for functional organic compounds.Type: GrantFiled: September 26, 2000Date of Patent: June 25, 2002Assignee: Showa Denko K.K.Inventors: Masato Kaneda, Yoshihiro Honda
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Patent number: 6407295Abstract: The invention relates to a process for preparing higher oxo alcohols from mixtures of isomeric olefins having from 5 to 24 carbon atoms by hydroformylation in the presence of a catalyst at elevated temperature and at elevated pressure, in which the hydroformylation is carried out in one stage, the olefin conversion rate for one pass is restricted to from 40 to 90% to produce a reaction mixture, and the reaction mixture is selectively hydrogenated.Type: GrantFiled: September 15, 1999Date of Patent: June 18, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Alfred Kaizik, Bernhard Scholz, Walter Toetsch, Martin Trocha, Wilfried Bueschken, Franz Nierlich
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Patent number: 6331657Abstract: 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: GrantFiled: September 15, 1999Date of Patent: December 18, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Alfred Kaizik, Bernhard Scholz, Walter Toetsch, Wilfried Bueschken, Franz Nierlich
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Patent number: 6278030Abstract: 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: GrantFiled: January 14, 2000Date of Patent: August 21, 2001Assignee: Exxon Chemical Patents, Inc.Inventors: Jose Manuel Vargas, Kenneth Lloyd Riley
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Patent number: 6239318Abstract: 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: GrantFiled: September 15, 1999Date of Patent: May 29, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Joachim Schuler, Alfred Kaizik, Bernhard Scholz, Wilfried Bueschken, Wilhelm Droste
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Patent number: 6184424Abstract: A process for the hydrogenation of reaction mixtures from the hydroformylation of C5 to C24 olefins using hydrogen on fixed catalysts at elevated temperature, in which the aldehydes, alcohols, formates and low-boilers are evaporated from the reaction mixture and passed in the vapor state over a support-free Cu/Cr catalyst.Type: GrantFiled: September 15, 1999Date of Patent: February 6, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Wilfried Bueschken, Dietmar Gubisch
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Patent number: 6049011Abstract: A dilute ethylene stream, e.g., one produced by steam cracking, is oxonated to yield propanal, without the need to separate other lower hydrocarbons.Type: GrantFiled: October 15, 1997Date of Patent: April 11, 2000Assignee: Exxon Chemical Patents Inc.Inventors: Gabor Kiss, Michael G Matturro, Harry William Deckman, Frank Hershkowitz, David R. Lumgair, Jr., Gary F Janda, Daniel N King
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Patent number: 5866548Abstract: Caged acyloxyalkyl esters of phosphate-containing inositol phosphates which are capable of permeating cell membranes. The second messengers are protected (caged) at the 6-hydroxyl, with a photolabile group. Once inside the cell, the ester derivatives undergo enzymatic conversion to remove the acyloxyalkyl ester groups. The resulting caged compound remains biologically inactive until exposed to ultraviolet (UV) light. Upon UV light exposure, the active form of the second messenger is released within the cell.Type: GrantFiled: December 19, 1996Date of Patent: February 2, 1999Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Wenhong Li
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Patent number: 5834436Abstract: Acyloxyalkyl esters of phosphate-containing second messengers which are capable of permeating cell membranes. Once inside the cell, the ester derivatives undergo enzymatic conversion to the biologically active form of the second messenger. The acyloxyalkyl esters have the formula: ##STR1## wherein A.sub.1 to A.sub.6 is H, OH, F or ##STR2## wherein R is an alkyl group having from 2 to 6 carbon atoms and R' is H or CH.sub.3 or R is CH.sub.3 and R' is CH.sub.3 and wherein at least one of A.sub.1 to A.sub.6 is a phosphoester having the formula set forth above.Type: GrantFiled: June 7, 1995Date of Patent: November 10, 1998Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Carsten Schultz, Wenhong Li
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Patent number: 5831135Abstract: The present invention relates to a process for the catalytic selective hydrogenation of a polyunsaturated organic compound, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding the polyunsaturated organic compound and hydrogen to an upper part of a reactor to catalytically hydrogenate said the polyunsaturated organic compound to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein the polyunsaturated organic compound is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating stepType: GrantFiled: October 6, 1997Date of Patent: November 3, 1998Assignee: Huels AktiengesellschaftInventors: Wilfried Bueschken, Juergen Hummel
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Patent number: 5684215Abstract: A process for the preparation of alcohols by reaction of organic carbonyl compounds or mixtures containing them with hydrogen over a supported catalyst containing nickel, aluminum oxide, and zirconium dioxide at elevated temperature and, if appropriate, under elevated pressure. Ketones, aldehydes and derivatives thereof are reacted as the carbonyl compounds at temperatures of 60.degree. to 150.degree. C.Type: GrantFiled: December 28, 1992Date of Patent: November 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Gerhardt Horn, Carl Dieter Frohning
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Patent number: 5675045Abstract: The present invention relates to a process for the catalytic selective hydrogenation of a polyunsaturated organic compound, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding the polyunsaturated organic compound and hydrogen to an upper part of a reactor to catalytically hydrogenate said the polyunsaturated organic compound to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein the polyunsaturated organic compound is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating stepType: GrantFiled: June 26, 1996Date of Patent: October 7, 1997Assignee: Huels AktiengesellschaftInventors: Wilfried Bueschken, Juergen Hummel
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Patent number: 5600031Abstract: A process for preparing oxo alcohols and aldehydes by the cobalt catalyzed hydroformylation of C.sub.2 to C.sub.17 linear or branched monoolefins with subsequent hydrogenation of the hydroformylation product, in which oxo process aqueous solutions of cobalt salts are converted to active hydrido cobalt carbonyl species in a preformer reactor under preforming reaction conditions, the improvement characterized by the preformer reactor containing a shell-type, metal on substrate, preformer catalyst.Type: GrantFiled: August 18, 1995Date of Patent: February 4, 1997Assignee: Exxon Chemical Patents, Inc.Inventor: Patricia B. Roussel
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Patent number: 5583250Abstract: Mixtures of isomeric decyl alcohols obtained by oligomerization of propylene in the presence of deactivated zeolites as catalysts, followed by separation of the nine carbon olefins from the oligomer mixture, then hydroformylation of the 9 carbon olefins to 10 carbon aldehydes, and hydrogenation of the aldehydes to the corresponding alcohols. The mixtures, when esterified with phthalic acid, or anhydride, provide a mixture of isomeric di-decyl phthalates that can be used as plasticizers.Type: GrantFiled: June 7, 1995Date of Patent: December 10, 1996Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas M uller, J urgen Szameitat, Ernst Wiebus
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Patent number: 5516948Abstract: Mixtures of isomeric decyl alcohols obtained by oligomerization of propylene in the presence of deactivated zeolites as catalysts, followed by separation of the nine carbon olefins from the oligomer mixture, then hydroformylation of the 9 carbon olefins to 10 carbon aldehydes, and hydrogenation of the aldehydes to the corresponding alcohols. The mixtures, when esterified with phthalic acid, or anhydride, provide a mixture of isomeric di-decyl phthalates that can be used as plasticizers.Type: GrantFiled: June 7, 1995Date of Patent: May 14, 1996Assignee: Hoechst AGInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5476972Abstract: Disclosed is a one-step method for synthesis of ethers from mixtures of acetone and t-butyl alcohol which comprises reacting an acetone-rich feed over a bifunctional catalyst comprising 5%-45% by weight hydrogenation catalyst on 55%-95% of the total catalyst weight of a support comprising a zeolite and a Group III or IV oxide.Type: GrantFiled: January 28, 1994Date of Patent: December 19, 1995Assignee: Texaco Chemical Inc.Inventors: Pei-Shing E. Dai, Robert J. Taylor, Jr., John F. Knifton, Bobby R. Martin
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Patent number: 5475161Abstract: A process for the preparation of alcohols by reaction of organic carbonyl compounds with hydrogen in two stages at elevated temperature and, optionally, elevated pressure. In the first stage, hydrogen and the carbonyl compounds are fed as a gas to a copper-containing catalyst and reacted to 80 to 99.5 percent of the theoretical conversion. In the second stage, the reaction product of the first stage is fed to a nickel/alumina/zirconium dioxide catalyst as a liquid, along with hydrogen. The carbonyl compounds used include aldehydes and their derivatives and, in particular, aliphatic unsaturated and saturated aldehydes.Type: GrantFiled: January 17, 1992Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Gerhardt Horn, Carl D. Frohning, Hans Liebern, Wolfgang Zgorzelski
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Patent number: 5462986Abstract: Mixtures of isomeric decyl alcohols prepared by hydroformylation of mixtures of butene-1 and butene-2 in two stages to give aldehyde mixtures, and condensation of the aldehyde mixtures to form an aldol mixture, followed by separation and hydrogenation. The first stage of the hydroformylation proceeds in the presence of rhodium catalysts dissolved in water, the second stage in the presence of cobalt catalysts homogeneously dissolved in the reaction medium. The mixture of isomeric decyl alcohols, when esterified with phthalic acid, yields a mixture of isomeric decyl phthalates which are useful as plasticizers.Type: GrantFiled: February 14, 1995Date of Patent: October 31, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgana Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus