By Reduction, Dehydration, Or Cleavage Patents (Class 568/903)
  • Patent number: 8003838
    Abstract: 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: Grant
    Filed: April 2, 2008
    Date of Patent: August 23, 2011
    Assignee: Firmenich SA
    Inventors: Philippe Dupau, Lucia Bonomo
  • Publication number: 20110015451
    Abstract: 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: Application
    Filed: January 27, 2009
    Publication date: January 20, 2011
    Inventor: Peter Theodorus Witte
  • Publication number: 20100317901
    Abstract: 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: Application
    Filed: June 9, 2010
    Publication date: December 16, 2010
    Inventors: Raghunath V. Chaudhari, Debdut S. Roy, Bala Subramaniam
  • Publication number: 20100234649
    Abstract: 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: Application
    Filed: February 16, 2007
    Publication date: September 16, 2010
    Inventors: Kaoru Fujimoto, Kenichiro Fujimoto, Noriyuki Yamane
  • Patent number: 7795479
    Abstract: 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: Grant
    Filed: December 15, 2009
    Date of Patent: September 14, 2010
    Assignee: UOP LLC
    Inventors: David A. Wegerer, Stephen R. Dunne
  • Patent number: 7754929
    Abstract: 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: Grant
    Filed: April 2, 2008
    Date of Patent: July 13, 2010
    Assignee: Innovaroma SA
    Inventors: Philippe Dupau, Lucia Bonomo
  • Patent number: 7754928
    Abstract: 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: Grant
    Filed: November 30, 2007
    Date of Patent: July 13, 2010
    Assignee: E. I. duPont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Publication number: 20100137568
    Abstract: 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: Application
    Filed: March 26, 2008
    Publication date: June 3, 2010
    Applicants: CBD TECHNOLOGIES LTD., Yissum Research Development Company
    Inventors: Oded Shoseyov, Ziv Shani, Miron Abramson, Noga Barimboim, Mara Dekel, Shaul Lapidot
  • Publication number: 20100113844
    Abstract: 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: Application
    Filed: April 2, 2008
    Publication date: May 6, 2010
    Inventors: Philippe Dupau, Lucia Bonomo
  • Publication number: 20100099904
    Abstract: 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: Application
    Filed: April 2, 2008
    Publication date: April 22, 2010
    Inventors: Philippe Dupau, Lucia Bonomo
  • Patent number: 7696386
    Abstract: 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: Grant
    Filed: September 28, 2007
    Date of Patent: April 13, 2010
    Assignee: Japan Science and Technology Agency
    Inventors: Hideo Hosono, Haritha Buchammagari, Yoshitake Toda, Masahiro Hirano, Kohtaro Osakada, Daisuke Takeuchi
  • Publication number: 20100056832
    Abstract: 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: Application
    Filed: November 30, 2007
    Publication date: March 4, 2010
    Inventor: Leo Ernest Manzer
  • Patent number: 7663003
    Abstract: 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: Grant
    Filed: November 9, 2007
    Date of Patent: February 16, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Sylvia Huber-Dirr, Michael Hesse, Andrea Haunert, Henrik Junicke
  • Publication number: 20100022807
    Abstract: 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: Application
    Filed: December 27, 2006
    Publication date: January 28, 2010
    Inventors: Els D'Hondt, Pierre Jacobs, Bert Sels
  • Publication number: 20090275787
    Abstract: 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: Application
    Filed: April 23, 2009
    Publication date: November 5, 2009
    Applicant: Lanzatech New Zealand Limited
    Inventors: Richard Llewellyn Sydeny Forster, Sean Dennis Simpson, Christophe Collet
  • Publication number: 20090240085
    Abstract: 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: Application
    Filed: September 28, 2007
    Publication date: September 24, 2009
    Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCY
    Inventors: Hideo Hosono, Haritha Buchammagari, Yoshitake Toda, Masahiro Hirano, Kohtaro Osakada, Daisuke Takeuchi
  • Publication number: 20090012334
    Abstract: A method of producing short chain alcohols from glycerol generated as a byproduct of biodiesel production is provided utilizing separate dehydration and hydrogenation.
    Type: Application
    Filed: May 15, 2008
    Publication date: January 8, 2009
    Applicant: PRIMAFUEL, INC.
    Inventors: Christian Hulteberg, Jan Brandin, Richard R. Woods, Brook Porter
  • Publication number: 20090005614
    Abstract: A method of producing short chain alcohols from glycerol generated as a byproduct of biodiesel production is provided.
    Type: Application
    Filed: May 15, 2008
    Publication date: January 1, 2009
    Applicant: PRIMAFUEL, INC.
    Inventors: Christian Hulteberg, Jan Brandin, Richard R. Woods, Brook Porter
  • Patent number: 7456326
    Abstract: 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: Grant
    Filed: March 1, 2007
    Date of Patent: November 25, 2008
    Assignee: Praxair Technology, Inc.
    Inventor: Henry Edward Howard
  • Patent number: 7259280
    Abstract: 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: Grant
    Filed: March 22, 2006
    Date of Patent: August 21, 2007
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Andrew P. Kahn, Stephen H. Harris
  • Patent number: 7183443
    Abstract: 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: Grant
    Filed: April 7, 2003
    Date of Patent: February 27, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Bernardus Henricus Nicolaas Dassen, Bernardus Kaptein, Quirinus Bernardus Broxterman
  • Patent number: 7098369
    Abstract: 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: Grant
    Filed: September 24, 2003
    Date of Patent: August 29, 2006
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Renata Helena Van Der Made
  • Patent number: 7084312
    Abstract: 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: Grant
    Filed: August 22, 2000
    Date of Patent: August 1, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Sylvia Huber, Michael Jolyon Sprague, Boris Breitscheidel, Joachim Wulff-Döring, Michael Hesse, Rolf Pinkos, Shelue Liang, Otto Kumberger, Marc Walter
  • Patent number: 6916964
    Abstract: 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: Grant
    Filed: December 4, 2002
    Date of Patent: July 12, 2005
    Assignee: BASF AG
    Inventors: Hans-Georg Göbbel, Till Gerlach, Frank Funke, Klaus Ebel, Signe Unverricht, Gerd Kaibel
  • Publication number: 20040122265
    Abstract: 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: Application
    Filed: December 10, 2003
    Publication date: June 24, 2004
    Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder
  • Patent number: 6743956
    Abstract: 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: Grant
    Filed: December 4, 2002
    Date of Patent: June 1, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Mathias Haake, Till Gerlach, Frank Funke
  • Patent number: 6555717
    Abstract: Secondary alcohols, specifically diols and polyols, are dehydroxylated to the corresponding primary alcohols using a homogeneous organometallic ruthenium complex catalyst.
    Type: Grant
    Filed: June 20, 2001
    Date of Patent: April 29, 2003
    Assignees: E. I. du Pont de Nemours and Company, Brookhaven Science Associates
    Inventors: R. Morris Bullock, Marcel Schlaf, Paul Joseph Fagan, Elisabeth M. Hauptman
  • Patent number: 6448457
    Abstract: 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: Grant
    Filed: August 29, 2000
    Date of Patent: September 10, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Hesse, Detlef Kratz, Gerhard Schulz, Marc Walter, Manfred Sauerwald
  • Patent number: 6440891
    Abstract: 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: Grant
    Filed: August 29, 2000
    Date of Patent: August 27, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Heiko Maas, Rocco Paciello, Michael Röper, Jakob Fischer, Wolfgang Siegel
  • Publication number: 20020077511
    Abstract: Secondary alcohols, specifically diols and polyols, are dehydroxylated to the corresponding primary alcohols using a homogeneous organometallic ruthenium complex catalyst.
    Type: Application
    Filed: June 20, 2001
    Publication date: June 20, 2002
    Inventors: R. Morris Bullock, Marcel Schlaf, Paul Joseph Fagan
  • Patent number: 6333441
    Abstract: 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: Grant
    Filed: March 4, 1993
    Date of Patent: December 25, 2001
    Assignees: Nissan Chemical Industries, Ltd.
    Inventors: Fumie Sato, Katsuaki Miyaji, Takehiro Amano
  • Publication number: 20010039368
    Abstract: 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: Application
    Filed: December 12, 2000
    Publication date: November 8, 2001
    Inventors: Klaus Reimer, Gerd Kaibel, Ulrich Kammel, Franz Josef Brocker, Andreas Ansmann, Heinz Etzrodt, Manfred Stroezel, Mathias Haake, Lothar Laupichler, Bernhard Bockstiegel
  • Patent number: 6242620
    Abstract: 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: Grant
    Filed: March 5, 1998
    Date of Patent: June 5, 2001
    Assignee: Henkel Corporation
    Inventors: A. Fred Elsasser, C. William Blewett, Charles M. White
  • Patent number: 6130360
    Abstract: 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: Grant
    Filed: December 9, 1998
    Date of Patent: October 10, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Arnd Bottcher, Melanie Brunner, Jochem Henkelmann, Heinz Rutter
  • Patent number: 6002047
    Abstract: 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: Grant
    Filed: October 28, 1997
    Date of Patent: December 14, 1999
    Assignee: Roche Vitamins Inc.
    Inventors: Michael Jansen, Claus Rehren
  • Patent number: 5981812
    Abstract: 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: Grant
    Filed: November 12, 1997
    Date of Patent: November 9, 1999
    Assignee: Th. Goldschmidt AG
    Inventors: Jorg Eufinger, Wilfried Knott, Andreas Mehrwald, Angelo Provinzano
  • Patent number: 5728376
    Abstract: 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: Grant
    Filed: April 25, 1995
    Date of Patent: March 17, 1998
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Athula B. Attygalle, Gulab N. Jham, Ales Svatos, Rosa T.S. Frighetto
  • Patent number: 5672783
    Abstract: 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: Grant
    Filed: August 29, 1996
    Date of Patent: September 30, 1997
    Assignee: Takasago International Corporation
    Inventors: Hiroyuki Matsuda, Takeshi Yamamoto
  • Patent number: 5599848
    Abstract: 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: Grant
    Filed: August 7, 1995
    Date of Patent: February 4, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Klein, Ulrich Neumann, Wolfgang Mackenroth, Guenter Renz, Wolfgang Krieg, Christiane Mackenroth, Ernst Buschmann, Jacobus J. DeKramer, Roland Milli
  • Patent number: 5600015
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: February 4, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Robert K. M uller
  • Patent number: 5600032
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: February 4, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Keiichi Sato, Yoko Seto, Iwao Nakajima
  • Patent number: 5449838
    Abstract: 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: Grant
    Filed: December 30, 1993
    Date of Patent: September 12, 1995
    Assignee: Texaco Chemical Inc.
    Inventors: John F. Knifton, Ernest L. Yeakey, Pei-Shing E. Dai
  • Patent number: 5444170
    Abstract: 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: Grant
    Filed: January 10, 1994
    Date of Patent: August 22, 1995
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Gamini A. Vedage
  • Patent number: 5286899
    Abstract: 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: Grant
    Filed: August 27, 1992
    Date of Patent: February 15, 1994
    Assignee: Sepracor, Inc.
    Inventor: Yun Gao
  • Patent number: 5236715
    Abstract: 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: Grant
    Filed: January 28, 1992
    Date of Patent: August 17, 1993
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Leslie M. McDonough, Harry G. Davis
  • Patent number: 5210335
    Abstract: 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: Grant
    Filed: July 9, 1992
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Walter Himmele
  • Patent number: 5183923
    Abstract: 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: Grant
    Filed: March 28, 1990
    Date of Patent: February 2, 1993
    Assignee: Texaco Chemical Company
    Inventors: Michael Cuscurida, George P. Speranza
  • Patent number: 5118837
    Abstract: A modified ruthenium catalyst can be used to selectively hydrogenate an olefinic double bond in the presence of another olefinic double bond in the same or in a different molecule. Modifiers are selected from compounds containing trivalent nitrogen, trivalent phosphorus and divalent sulfur.
    Type: Grant
    Filed: February 12, 1987
    Date of Patent: June 2, 1992
    Assignee: Givaudan Corporation
    Inventors: Alan J. Chalk, Laszlo V. Wertheimer
  • Patent number: 5057631
    Abstract: Butadiene and water are reacted continuously in the presence of a solvent capable of dissolving both reactants and a palladium catalyst with the mole ratio of butadiene to the reaction product octa-2,7-dien-1-ol in the reaction mixture being maintained at 0.6 or more. By this process, octa-2,7-dien-1-ol can be produced continuously without reductions in reaction rate and selectivity and with decreased insoluble polymer formation.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: October 15, 1991
    Assignee: Kuraray Co., Ltd.
    Inventors: Yasuo Tokitoh, Noriaki Yoshimura
  • Patent number: 5015788
    Abstract: A process for the preparation of saturated alcohols by catalytic hydrogenation of acetylenic alcohols at a temperature of from 50.degree. to 200.degree. C. and under a pressure of from 30 to 320 bar, wherein the catalyst used has a content of from 20 to 75% of nickel oxide, from 10 to 75% of zirconium dioxide and from 5 to 50% of copper oxide, by weight of the oxidic, unreduced catalyst.
    Type: Grant
    Filed: April 2, 1990
    Date of Patent: May 14, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Toussaint, Juergen Schossig, Heinz Graefje, Wolfgang Reiss, Roland Spahl, Matthias Irgang, Walter Himmel, Gerhard Koppenhoefer