By Reduction, Dehydration, Or Cleavage Patents (Class 568/903)
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Publication number: 20110319672Abstract: A process for converting a sugar, sugar alcohol, or glycerol to a valuable chemical is described. The process may use a support comprising zirconium oxide promoted by a polyacid or promoter material. A catalytically active metal may be impregnated on the polyacid-promoted zirconium oxide support and the catalyst may then be introduced the sugar, sugar alcohol, or glycerol a source of hydrogen under reaction conditions. At least 40 wt % of the sugar, sugar alcohol or glycerol may be converted to a polyol and/or a shorter carbon-chain alcohol that may include at least one of propylene glycol, ethylene glycol, glycerin, methanol, ethanol, propanol and butandiols. Specific processes for converting glycerin having a selectivity for propylene glycol and for converting sorbitol with a selectivity for propylene glycol, ethylene glycol, and/or glycerin are also described.Type: ApplicationFiled: March 3, 2010Publication date: December 29, 2011Applicant: SUD-CHEMIE INC.Inventors: Aiguo Liu, Wayne Turbeville, Christopher C. Luckett, Hui Hui (Faye) Li
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Patent number: 8067646Abstract: Systems and processes for dehydration of a process stream in the production of motor fuel grade ethanol (MFGE) can include temperature controlled adsorption of water in the process stream, and heat pumping of the associated heat of adsorption. The process can include providing a process stream (110) including ethanol and water to a first temperature controlled adsorber (102) where water is removed by adsorption to produce an MFGE product stream (114) and an associated heat of adsorption. A cooling fluid can be provided to the first temperature controlled adsorber (102) to remove heat of adsorption and produce a heated cooling fluid (120). Heat from the heated cooling fluid can be provided to a heat sink.Type: GrantFiled: December 17, 2008Date of Patent: November 29, 2011Assignee: UOP LLCInventors: David A. Wegerer, Stephen R. Dunne
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Publication number: 20110218364Abstract: An intermetallic magnetic compound of iron oxide and palladium with a nanometer particle size is disclosed, together with a method of making magnetic nanoparticles that include an intermetallic bond between palladium and iron-oxide. Additionally, a method is disclosed of catalyzing an organic reaction by contacting the organic reagents with an intermetallic magnetic compound of iron oxide and palladium that has nanometer particle size in an amount sufficient to catalyze the organic reaction.Type: ApplicationFiled: March 5, 2010Publication date: September 8, 2011Applicant: CEM CORPORATIONInventors: Keith A. Porter, E. Keller Barnhardt
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Patent number: 8003838Abstract: The present invention relates to the use of Ruthenium complexes having cyclopentadienyl derivatives and a diene as ligands, together with some acidic additives for improving the selectivity in the 1,4-hydrogenation of conjugated dienes into the corresponding “cis”-alkene as major product, i.e. wherein the two substituents in position 2,3 of the diene are in a cis configuration in the corresponding alkene.Type: GrantFiled: April 2, 2008Date of Patent: August 23, 2011Assignee: Firmenich SAInventors: Philippe Dupau, Lucia Bonomo
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Publication number: 20110015451Abstract: The invention is directed to a process for the preparation of an aqueous colloidal precious metal suspension, which process comprises reducing a precious metal salt in aqueous solution using a functionalised, water soluble quaternary ammonium salt in the absence of organic solvents, to form elementary nanoparticles.Type: ApplicationFiled: January 27, 2009Publication date: January 20, 2011Inventor: Peter Theodorus Witte
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Publication number: 20100317901Abstract: A catalyst composition can include: a support; a ruthenium catalyst (Ru) nanoparticle; and a linker linking the Ru nanoparticle to the support, wherein the linker is stable under hydrogenolysis conditions. In one aspect, the linker can include 3-aminopropyl trimethoxysilane (APTS) or derivatives thereof, such as those with amine functionality. In another aspect, the linker can include phosphotungstic acid (PTA) or other similar solid acid agents. In another aspect, the support can be selected from alumina, carbon, silica, a zeolite, TiO2, ZrO2, or another suitable material. A specific example of a support includes zeolite, such as a NaY zeolite. The Ru nanoparticle can have a size range from about 1 nm to about 25 nm, and can be obtained by reduction of Ru salts.Type: ApplicationFiled: June 9, 2010Publication date: December 16, 2010Inventors: Raghunath V. Chaudhari, Debdut S. Roy, Bala Subramaniam
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Publication number: 20100234649Abstract: This catalyst for methanol synthesis, where methanol is synthesized via a formic ester, is a catalyst for methanol synthesis which carries out a reaction under the presence of a starting material gas containing hydrogen and at least either one of carbon monoxide and carbon dioxide, and an alcohol as a solvent, and includes a catalyst containing Cu, Mg, Na, Pd, and an alkali metal formate salt.Type: ApplicationFiled: February 16, 2007Publication date: September 16, 2010Inventors: Kaoru Fujimoto, Kenichiro Fujimoto, Noriyuki Yamane
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Patent number: 7795479Abstract: Systems and processes for dehydration of a process stream in the production of motor fuel grade ethanol (MFGE) can include temperature controlled adsorption of water in the process stream, and heat pumping of the associated heat of adsorption. The process includes providing a process stream including ethanol and water to a first temperature controlled adsorber where water is removed by adsorption to produce a MFGE product stream and an associated heat of adsorption. A cooling fluid is provided to the first temperature controlled adsorber to remove heat of adsorption and produce a heated cooling fluid. Heat from the heated cooling fluid is provided to a heat sink. A multiple step regeneration cycle is provided that allows for increased recovery of MFGE product.Type: GrantFiled: December 15, 2009Date of Patent: September 14, 2010Assignee: UOP LLCInventors: David A. Wegerer, Stephen R. Dunne
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Patent number: 7754929Abstract: The present invention relates to the use of Ru complexes, having a pentamethyl-cyclopentadienyl and a cyclooctadine as ligands, together with some acidic additives for improving the selectivity in the 1,4-hydrogenation of sorbol into the corresponding Z-alkene as major product.Type: GrantFiled: April 2, 2008Date of Patent: July 13, 2010Assignee: Innovaroma SAInventors: Philippe Dupau, Lucia Bonomo
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Patent number: 7754928Abstract: The present invention relates to a method for making 2-butanol from 2,3-butanediol by using a heterogeneous catalyst system that can function both as an acid catalyst and as a hydrogenation catalyst.Type: GrantFiled: November 30, 2007Date of Patent: July 13, 2010Assignee: E. I. duPont de Nemours and CompanyInventor: Leo Ernest Manzer
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Publication number: 20100137568Abstract: The present invention provides a bio-fuel, wood or other product, such as a paper, textile or yarn product. The product can contain material from a transgenic plant over-expressing a nucleic acid molecule encoding an enzyme that causes the plant cell wall to be more water soluble than the wild type.Type: ApplicationFiled: March 26, 2008Publication date: June 3, 2010Applicants: CBD TECHNOLOGIES LTD., Yissum Research Development CompanyInventors: Oded Shoseyov, Ziv Shani, Miron Abramson, Noga Barimboim, Mara Dekel, Shaul Lapidot
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Publication number: 20100113844Abstract: The present invention relates to the use of Ru complexes, having a pentamethyl-cyclopentadienyl and a cyclooctadine as ligands, together with some acidic additives for improving the selectivity in the 1,4-hydrogenation of sorbol into the corresponding Z-alkene as major product.Type: ApplicationFiled: April 2, 2008Publication date: May 6, 2010Inventors: Philippe Dupau, Lucia Bonomo
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Publication number: 20100099904Abstract: The present invention relates to the use of Ruthenium complexes having cyclopentadienyl derivatives and a diene as ligands, together with some acidic additives for improving the selectivity in the 1,4-hydrogenation of conjugated dienes into the corresponding “cis”-alkene as major product, i.e. wherein the two substituents in position 2,3 of the diene are in a cis configuration in the corresponding alkene.Type: ApplicationFiled: April 2, 2008Publication date: April 22, 2010Inventors: Philippe Dupau, Lucia Bonomo
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Patent number: 7696386Abstract: The invention is a process of using, as a reducing agent, a 12CaO.7Al2O3 electride containing electrons in a number of 1019 or more and 2.3×1021 cm?3 or less in its cages to subject a carbonyl compound to reductive coupling in a solvent, thereby synthesizing a diol or polydiol. The invention is also a process of reducing a ketone compound in a solvent, thereby synthesizing a secondary alcohol or diketone compound. According to the process of the invention, it is possible to synthesize a diol or polydiol, or a secondary alcohol or diketone compound through simple operations in a short period without using an expensive and harmful metal hydride or metal salt nor limiting the atmosphere for the synthesis to an inert gas atmosphere as in conventional processes.Type: GrantFiled: September 28, 2007Date of Patent: April 13, 2010Assignee: Japan Science and Technology AgencyInventors: Hideo Hosono, Haritha Buchammagari, Yoshitake Toda, Masahiro Hirano, Kohtaro Osakada, Daisuke Takeuchi
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Publication number: 20100056832Abstract: The present invention relates to a method for making 2-butanol from 2,3-butanediol by using a heterogeneous catalyst system that can function both as an acid catalyst and as a hydrogenation catalyst.Type: ApplicationFiled: November 30, 2007Publication date: March 4, 2010Inventor: Leo Ernest Manzer
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Patent number: 7663003Abstract: A process for hydrogenating an organic compound which has at least one carbonyl group, in which the organic compound is brought into contact in the presence of hydrogen with a shaped article which can be produced in a process in which (i) an oxidic material comprising copper oxide, aluminum oxide and at least one of the oxides of lanthanum, tungsten, molybdenum, titanium or zirconium is prepared, (ii) powdered metallic copper, copper flakes, powdered cement, graphite or a mixture thereof is added to the oxidic material, and (iii) the mixture resulting from (ii) is shaped to a shaped article.Type: GrantFiled: November 9, 2007Date of Patent: February 16, 2010Assignee: BASF AktiengesellschaftInventors: Sylvia Huber-Dirr, Michael Hesse, Andrea Haunert, Henrik Junicke
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Publication number: 20100022807Abstract: The invention relates generally to the production of oxygenated hydrocarbons such as lower alcohols and more preferably 1,2-propanediol. More particularly, this invention comprises a single-step catalytic process for the catalytic production of lower alcohols such as methanol, ethanol, ethylene glycol and 1,2-propanediol from glycerol in aqueous medium. The catalyst comprises a metal selected from the Group VIII transition metals, preferably platinum, alloys thereof and mixtures thereof and a microporous carrier, preferably a faujasite-type zeolite.Type: ApplicationFiled: December 27, 2006Publication date: January 28, 2010Inventors: Els D'Hondt, Pierre Jacobs, Bert Sels
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Publication number: 20090275787Abstract: The invention relates to methods for the production of alcohols by microbial fermentation, particularly microbial fermentation of substrates comprising glycerol and/or acetate, to butanol.Type: ApplicationFiled: April 23, 2009Publication date: November 5, 2009Applicant: Lanzatech New Zealand LimitedInventors: Richard Llewellyn Sydeny Forster, Sean Dennis Simpson, Christophe Collet
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Publication number: 20090240085Abstract: The invention is a process of using, as a reducing agent, a 12CaO.7Al2O3 electride containing electrons in a number of 1019 or more and 2.3×1021 cm?3 or less in its cages to subject a carbonyl compound to reductive coupling in a solvent, thereby synthesizing a diol or polydiol. The invention is also a process of reducing a ketone compound in a solvent, thereby synthesizing a secondary alcohol or diketone compound. According to the process of the invention, it is possible to synthesize a diol or polydiol, or a secondary alcohol or diketone compound through simple operations in a short period without using an expensive and harmful metal hydride or metal salt nor limiting the atmosphere for the synthesis to an inert gas atmosphere as in conventional processes.Type: ApplicationFiled: September 28, 2007Publication date: September 24, 2009Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCYInventors: Hideo Hosono, Haritha Buchammagari, Yoshitake Toda, Masahiro Hirano, Kohtaro Osakada, Daisuke Takeuchi
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Publication number: 20090012334Abstract: A method of producing short chain alcohols from glycerol generated as a byproduct of biodiesel production is provided utilizing separate dehydration and hydrogenation.Type: ApplicationFiled: May 15, 2008Publication date: January 8, 2009Applicant: PRIMAFUEL, INC.Inventors: Christian Hulteberg, Jan Brandin, Richard R. Woods, Brook Porter
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Publication number: 20090005614Abstract: A method of producing short chain alcohols from glycerol generated as a byproduct of biodiesel production is provided.Type: ApplicationFiled: May 15, 2008Publication date: January 1, 2009Applicant: PRIMAFUEL, INC.Inventors: Christian Hulteberg, Jan Brandin, Richard R. Woods, Brook Porter
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Patent number: 7456326Abstract: Byproduct solids produced in the processing of carbohydrate material to produce ethanol are dried in a recirculating stream of gaseous carbon dioxide into which carbon dioxide produced in that processing is fed. Organic contaminants and water vapor report to the recirculating carbon dioxide stream and are removed therefrom.Type: GrantFiled: March 1, 2007Date of Patent: November 25, 2008Assignee: Praxair Technology, Inc.Inventor: Henry Edward Howard
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Patent number: 7259280Abstract: A process for producing an alkenyl alcohol from a diol is disclosed. The process comprises dehydrating a diol in the presence of a catalyst comprising cerium oxide supported on a carrier. The carrier has a surface area in the range of 0.1 to 50 m2/g. The catalyst is more active than unsupported cerium oxide.Type: GrantFiled: March 22, 2006Date of Patent: August 21, 2007Assignee: Lyondell Chemical Technology, L.P.Inventors: Andrew P. Kahn, Stephen H. Harris
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Patent number: 7183443Abstract: Process for the preparation of enantiomerically enriched amino aldehydes and amino alcohols, wherein a corresponding enantiomerically enriched amino nitrile is subjected to hydrogenation in the presence of hydrogen, a hydrogenation catalyst, preferably a Pd-catalyst and a mineral acid. For the preparation of an amino aldehyde hydrogen preferably is present at a hydrogen-pressure between 0.1 and 2 MPa, in particular between 0.5 and 1 MPa. The amino aldehyde preferably is isolated in the form of a chemically and configurationally stable derivative. For the preparation of an amino alcohol, preferably at least during part of the hydrogenation hydrogen is present at a hydrogen-pressure between 2 and 10 MPa, in particular between 4 and 6 MPa. In a preferred embodiment the hydrogen-pressure initially is between 0.5 and 2 MPa and subsequently, after most of the nitrile starting material is converted, the hydrogen pressure is increased to a value between 2 and 10 MPa.Type: GrantFiled: April 7, 2003Date of Patent: February 27, 2007Assignee: DSM IP Assets B.V.Inventors: Bernardus Henricus Nicolaas Dassen, Bernardus Kaptein, Quirinus Bernardus Broxterman
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Patent number: 7098369Abstract: A process for producing primary alcohols from secondary alcohols and/or tertiary alcohols and/or ketones, wherein the process comprises reacting a compound selected from a secondary alcohol, a tertiary alcohol, a ketone, or mixtures thereof, with carbon monoxide and hydrogen in the presence of a catalyst based on: (i) a source of Group VIII metal, (ii) a bidentate ligand having the general formula (I): R1R2M1-R-M2R3R4??(I) wherein M1 and M2 are independently P, As or Sb; R1 and R2 together represent a bivalent substituted or unsubstituted cyclic aliphatic group whereby the two free valencies are linked to M1; R3 and R4 independently represent a substituted or unsubstituted hydrocarbyl group, or together represent a bivalent or non-substituted cyclic group whereby the two free valencies are linked to M2; and R represents a bivalent aliphatic bridging group; and (iii) an acid having a pKa of 3 or less which is in excess over the Group VIII metal.Type: GrantFiled: September 24, 2003Date of Patent: August 29, 2006Assignee: Shell Oil CompanyInventors: Eit Drent, Renata Helena Van Der Made
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Patent number: 7084312Abstract: A process for the hydrogenation of an organic compound containing at least one carbonyl group comprises bringing the organic compound in the presence of hydrogen into contact with a shaped body which can be produced by a process in which (i) an oxidic material comprising copper oxide, zinc oxide and aluminum oxide is made available, (ii) pulverulent metallic copper or pulverulent cement or a mixture thereof is added to the oxidic material, and (iii) the mixture resulting from (ii) is shaped to form a shaped body.Type: GrantFiled: August 22, 2000Date of Patent: August 1, 2006Assignee: BASF AktiengesellschaftInventors: Sylvia Huber, Michael Jolyon Sprague, Boris Breitscheidel, Joachim Wulff-Döring, Michael Hesse, Rolf Pinkos, Shelue Liang, Otto Kumberger, Marc Walter
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Patent number: 6916964Abstract: The present invention relates to a continuous process for the selective hydrogenation of olefinically unsaturated carbonyl compounds to give unsaturated alcohols in particular of citral to give a mixture of geraniol and nerol, in a reactor containing a liquid phase, in which at least one catalyst is suspended, and which can additionally contain a gas phase, wherein the liquid phase and, if present, the gas phase are passed through a device in the reactor having openings or channels.Type: GrantFiled: December 4, 2002Date of Patent: July 12, 2005Assignee: BASF AGInventors: Hans-Georg Göbbel, Till Gerlach, Frank Funke, Klaus Ebel, Signe Unverricht, Gerd Kaibel
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Publication number: 20040122265Abstract: Process for the catalytic hydrogenation of an aliphatically unsaturated group in an organic compound in the presence of a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide.Type: ApplicationFiled: December 10, 2003Publication date: June 24, 2004Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder
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Patent number: 6743956Abstract: The present invention relates to a process for selective liquid phase hydrogenation of carbonyl compounds of the general formula I, where R1 and R2 are identical or different and are each independently hydrogen or a saturated or a mono- or polyunsaturated straight-chain or branched, optionally substituted C1-C20-alkyl radical, an optionally substituted aryl radical or an optionally substituted heterocyclic group, to give the corresponding alcohols of the general formula II where R1 and R2 are each as defined above, in the presence of hydrogen and a Pt/ZnO catalyst.Type: GrantFiled: December 4, 2002Date of Patent: June 1, 2004Assignee: BASF AktiengesellschaftInventors: Mathias Haake, Till Gerlach, Frank Funke
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Patent number: 6555717Abstract: Secondary alcohols, specifically diols and polyols, are dehydroxylated to the corresponding primary alcohols using a homogeneous organometallic ruthenium complex catalyst.Type: GrantFiled: June 20, 2001Date of Patent: April 29, 2003Assignees: E. I. du Pont de Nemours and Company, Brookhaven Science AssociatesInventors: R. Morris Bullock, Marcel Schlaf, Paul Joseph Fagan, Elisabeth M. Hauptman
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Patent number: 6448457Abstract: A process for the catalytic hydrogenation of a carbonyl compound or of a mixture of two or more carbonyl compounds in the presence of a catalyst which comprises an inorganic support containing TiO2, and as active component copper or a mixture of copper and at least one of the metals selected from the group of zinc, aluminum, cerium, a noble metal and a group VIII metal, wherein the copper surface area does not exceed 10 m2/g.Type: GrantFiled: August 29, 2000Date of Patent: September 10, 2002Assignee: BASF AktiengesellschaftInventors: Michael Hesse, Detlef Kratz, Gerhard Schulz, Marc Walter, Manfred Sauerwald
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Patent number: 6440891Abstract: The catalyst comprises at least one bi- or more highly dentate phosphonite ligand of the general formula I or salts and mixtures thereof and is useful in a process for hydroformylating compounds containing at least one ethylenically unsaturated double bond by reaction with carbon monoxide and hydrogen.Type: GrantFiled: August 29, 2000Date of Patent: August 27, 2002Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Rocco Paciello, Michael Röper, Jakob Fischer, Wolfgang Siegel
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Publication number: 20020077511Abstract: Secondary alcohols, specifically diols and polyols, are dehydroxylated to the corresponding primary alcohols using a homogeneous organometallic ruthenium complex catalyst.Type: ApplicationFiled: June 20, 2001Publication date: June 20, 2002Inventors: R. Morris Bullock, Marcel Schlaf, Paul Joseph Fagan
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Patent number: 6333441Abstract: A cis-olefin of the formula: R1—CH═CH—R2 is prepared by reducing an alkyne of the formula: R1—C≡C—R2 with formic acid in the presence of a palladium catalyst. R1 and R2 are independently selected from the group consisting of a hydrogen atom, ester group, substituted silyl group, carboxyl group, cyano group, aliphatic C1-C20 hydrocarbon group, and phenyl group. The cis-olefin which is a useful intermediate for the synthesis of fine chemicals is selectively produced in high yields.Type: GrantFiled: March 4, 1993Date of Patent: December 25, 2001Assignees: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Katsuaki Miyaji, Takehiro Amano
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Publication number: 20010039368Abstract: Alkenes are prepared by partial hydrogenation of alkynes in the liquid phase at from 20 to 250° C. and hydrogen partial pressures of from 0.Type: ApplicationFiled: December 12, 2000Publication date: November 8, 2001Inventors: Klaus Reimer, Gerd Kaibel, Ulrich Kammel, Franz Josef Brocker, Andreas Ansmann, Heinz Etzrodt, Manfred Stroezel, Mathias Haake, Lothar Laupichler, Bernhard Bockstiegel
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Patent number: 6242620Abstract: Sulfur and soap contaminants are removed from carboxylic acid esters by a process comprising the steps of: (1) contacting a carboxylic acid ester with an aqueous base at a temperature of from about 225° F. to about 280° F. while removing water to form a dry, crude ester; (2) contacting the dry, crude ester with an absorbent selected from the group consisting of silica gel, hydro-silica gel and mixtures thereof; (3) separating the absorbent from the ester.Type: GrantFiled: March 5, 1998Date of Patent: June 5, 2001Assignee: Henkel CorporationInventors: A. Fred Elsasser, C. William Blewett, Charles M. White
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Patent number: 6130360Abstract: An alkinol or mixture of two or more thereof is hydrogenated by bringing the alkinol or the mixture of two or more thereof into contact with a hydrogen-containing gas in the presence of a catalyst comprising as active metal at least one metal of transition group VIII of the Periodic Table, either alone or together with at least one metal of transition group I or VII of the Periodic Table, applied to a support, wherein the support contains macropores.Type: GrantFiled: December 9, 1998Date of Patent: October 10, 2000Assignee: BASF AktiengesellschaftInventors: Arnd Bottcher, Melanie Brunner, Jochem Henkelmann, Heinz Rutter
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Patent number: 6002047Abstract: The present invention is concerned with a process for the catalytic hydrogenation of organic compounds on a catalyst of amorphous metal alloys and in a solvent, with the hydrogenation being carried out under near-critical or supercritical conditions of the solvent. The amorphous metal alloys can be produced by the shock cooling of alloy melts having eutectic solidification points. By hydrogenation at hydrogen partial pressures between 5 and 400 bar there is obtained outstanding space-time yields with high long-term stability of the catalytic activity.Type: GrantFiled: October 28, 1997Date of Patent: December 14, 1999Assignee: Roche Vitamins Inc.Inventors: Michael Jansen, Claus Rehren
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Patent number: 5981812Abstract: The invention relates to a process for preparing .alpha.,.omega.-C.sub.4 -C.sub.20 -alkenols by catalytic monodehydration of .alpha.,.omega.-alkanediols over a catalyst system comprising the combination of aluminum phosphate and barium phosphate. The gas-phase dehydration which occurs over this catalyst at temperatures of from 300 to 500.degree. C. advantageously combines selectivity with a high space-time yield while simultaneously enabling a high throughput over the catalyst.Type: GrantFiled: November 12, 1997Date of Patent: November 9, 1999Assignee: Th. Goldschmidt AGInventors: Jorg Eufinger, Wilfried Knott, Andreas Mehrwald, Angelo Provinzano
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Patent number: 5728376Abstract: The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.Type: GrantFiled: April 25, 1995Date of Patent: March 17, 1998Assignee: Cornell Research Foundation, Inc.Inventors: Athula B. Attygalle, Gulab N. Jham, Ales Svatos, Rosa T.S. Frighetto
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Patent number: 5672783Abstract: Simple methods for producing 3,7-dimethyl-5,7-octadiene-1-ol and rose oxide are disclosed. Each of the methods comprises only one step in which the raw material, 3,7-dimethyl-6-hydroxy-7-octene-1-ol is dehydrated or further cyclized by heating while stirring at 80.degree. to 160.degree. C. in the presence of a zero-valent or divalent phosphine-palladium complex, or a combination of zero-valent or divalent palladium and a phosphorous compound having coordinating capabilities such as the combination of palladium acetate and triphenylphosphine. The methods give high yields and have cost saving characteristics.Type: GrantFiled: August 29, 1996Date of Patent: September 30, 1997Assignee: Takasago International CorporationInventors: Hiroyuki Matsuda, Takeshi Yamamoto
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Patent number: 5599848Abstract: A process for preparing a mixture of 8E,10E-dodecadienol (Ia), 8E,10Z-dodecadienol (Ib), 8Z,10E-dodecadienol (Ic) and 8Z,10Z-dodecadienol (Id),H.sub.3 C--CH.dbd.CH--CH.dbd.CH--(CH.sub.2).sub.6 --CH.sub.2 --OH(8E,10E=Ia)(8E,10Z=Ib)(8Z,10E=Ic)(8Z,10Z=Id)starting from 1,8-octanediol (II) which is converted with a halogenating agent into (III)Hal-CH.sub.2 --(CH.sub.2).sub.6 --CH.sub.2 --OH (III)where (III) is subsequently reacted with (IV),H.sub.2 C.dbd.CH--O--R (IV)to give (V)Hal-CH.sub.2 --(CH.sub.2).sub.6 --CH.sub.2 --O--CH(CH.sub.3)--OR(V),(V) is converted in the presence of magnesium and crotonaldehyde into (VI)H.sub.3 C--CH.dbd.CH--CH(OH)--(CH.sub.2).sub.8 --O--CH(CH.sub.3)--OR(VI)and the protective group R and the hydroxyl group are simultaneously eliminated from (VI) in the presence of acid, novel intermediates for this process, and methods for controlling the codling moth Cydia pomonella by interfering with mating using this mixture are described.Type: GrantFiled: August 7, 1995Date of Patent: February 4, 1997Assignee: BASF AktiengesellschaftInventors: Ulrich Klein, Ulrich Neumann, Wolfgang Mackenroth, Guenter Renz, Wolfgang Krieg, Christiane Mackenroth, Ernst Buschmann, Jacobus J. DeKramer, Roland Milli
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Patent number: 5600032Abstract: A method for producing an unsaturated alcohol having a chain structure formed by oligomerization of a conjugated alkadiene, which comprises reacting a conjugated alkadiene and water in the presence of carbon dioxide by means of a palladium compound and a phosphorus compound having at least one trivalent phosphorus-oxygen single bond, as catalyst.Type: GrantFiled: June 7, 1995Date of Patent: February 4, 1997Assignee: Mitsubishi Chemical CorporationInventors: Keiichi Sato, Yoko Seto, Iwao Nakajima
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Patent number: 5600015Abstract: There is described a process for the manufacture of isoprene derivatives of the general formula ##STR1## wherein the asymmetric centres can each individually have the (R)- or (S)-configuration, R represents a residue of the formulae ##STR2## R.sup.1 signifies lower alkyl or both R.sup.1 's together signify ethylene or propylene and n stands for the number 0, 1 or 2,in which a compound, which is present in the (E)- or (Z)-form, of the general formula ##STR3## wherein R, n and an optionally present asymmetric centre have the above significance,is asymmetrically hydrogenated with a ruthenium complex of an optically active atropisomeric diphosphine.Type: GrantFiled: May 19, 1995Date of Patent: February 4, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Robert K. M uller
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Patent number: 5449838Abstract: Disclosed is a two-step process for the generation of isopropyl t-butyl ether from a crude by-product acetone stream which comprises:a) Hydrogenating said crude acetone over a bulk metal, nickel-rich catalyst to give an isopropanol-rich effluent;b) subjecting said isopropanol-rich intermediate to etherification conditions in the presence of a strong acid catalyst selected from:(1) a cationic resin;(2) a .beta.-zeolite;(3) dealuminized Y-zeolites; and(4) metal-modified .beta.-zeolites.Type: GrantFiled: December 30, 1993Date of Patent: September 12, 1995Assignee: Texaco Chemical Inc.Inventors: John F. Knifton, Ernest L. Yeakey, Pei-Shing E. Dai
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Patent number: 5444170Abstract: This invention pertains to an improved process for the hydrogenation of acetylenic compounds prepared by the condensation of ketones or aldehydes with acetylene wherein the acetylenic compounds are contacted with hydrogen in the presence of a hydrogenation catalyst under conditions for effecting hydrogenation. The improvement in the process resides in utilizing a novel cocatalyst system for hydrogenating the acetylenic compounds to paraffins. The cocatalyst converts the inhibiting impurity in the feed to a noninhibiting species and comprises palladium and platinum, typically in a ratio of from 1 to 40 weight parts palladium per weight part platinum.Type: GrantFiled: January 10, 1994Date of Patent: August 22, 1995Assignee: Air Products and Chemicals, Inc.Inventor: Gamini A. Vedage
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Patent number: 5286899Abstract: An efficient and commercially-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.Type: GrantFiled: August 27, 1992Date of Patent: February 15, 1994Assignee: Sepracor, Inc.Inventor: Yun Gao
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Patent number: 5236715Abstract: A composition of three compounds, (E,E)-10,12-tetradecadien-1-ol acetate (I), (Z)-11-tetradecen-1-ol acetate (II), and (Z)-9-tetradecen-1-ol acetate (III), in a weight ratio of about 100:18:4 (I:II:III) is a highly effective sex attractant (pheromone) for the male mint root borer. The composition demonstrates biological activity toward mint root borer males comparable to or greater than that of the mint root borer moth females. By attracting adult males to field traps, the composition provides a means for detecting, monitoring, and controlling this agricultural pest.Type: GrantFiled: January 28, 1992Date of Patent: August 17, 1993Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Leslie M. McDonough, Harry G. Davis
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Patent number: 5210335Abstract: Lower polyhydric alcohols are prepared by catalytic hydrogenolysis of sucrose in an aqueous solution by using a catalyst whose active material essentially consists offrom 0 to 100% by weight of cobalt,from 0 to 85% by weight of copper andfrom 0 to 80% by weight of manganese,the percentages being based on the content of the metals.Type: GrantFiled: July 9, 1992Date of Patent: May 11, 1993Assignee: BASF AktiengesellschaftInventors: Ludwig Schuster, Walter Himmele
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Patent number: 5183923Abstract: The invention concerns a method for the preparation of polyurethane, polyester, polyamide, and polyurea diols which contain essentially all primary hydroxyl groups without capping by ethylene oxide. The method comprises coupling an alkylene oxide adduct of propylene glycol t-butyl ether or butylene glycol t-butyl ether or its aminated derivative with organic diisocyanates or dibasic acids followed by cleavage of the t-butyl group with an acid catalyst.The resulting diol is useful in many types of urethane applications including foams, elastomers and coatings.Type: GrantFiled: March 28, 1990Date of Patent: February 2, 1993Assignee: Texaco Chemical CompanyInventors: Michael Cuscurida, George P. Speranza