Gaseous Hydrogen Reactant Patents (Class 568/434)
  • Patent number: 8871982
    Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to a process for the reduction by hydrogenation, using molecular H2, of a C6-C20 conjugated dienal into the corresponding deconjugated enal, characterized in that said process is carried out in the presence of a catalytic system comprising at least a base and at least one complex in the form of a rhodium complex comprising a C34-C60 bidentate diphosphine ligand (L2) coordinating the rhodium.
    Type: Grant
    Filed: February 17, 2012
    Date of Patent: October 28, 2014
    Assignee: Firmenich SA
    Inventors: Lionel Saudan, Michel Alfred Joseph Saudan, Sylvia Joyeuse Adélaïde Ada Saudan
  • Publication number: 20130331611
    Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to a process for the reduction by hydrogenation, using molecular H2, of a C6-C20 conjugated dienal into the corresponding deconjugated enal, characterized in that said process is carried out in the presence of a catalytic system comprising at least a base and at least one complex in the form of a rhodium complex comprising a C34-C60 bidentate diphosphine ligand (L2) coordinating the rhodium.
    Type: Application
    Filed: February 17, 2012
    Publication date: December 12, 2013
    Applicant: FIRMENICH SA
    Inventors: Michel Alfred Joseph SAUDAN, Sylvia Joyeuse Adélaïde Ada SAUDAN
  • Patent number: 8367875
    Abstract: The invention relates to a process for the preparation of m-substituted alkyltoluenes of the formula (I) in which R1 is C1-C5-alkyl, wherein a p-substituted alkyltoluene of the formula (II) in which R1 has the meaning given under formula (I), is isomerized in the presence of ionic liquids to give an m-substituted alkyltoluene of the formula (I). The m-substituted alkyltoluenes obtainable according to the invention are starting compounds for the preparation of fragrances and aroma substances.
    Type: Grant
    Filed: February 10, 2011
    Date of Patent: February 5, 2013
    Assignee: BASF SE
    Inventors: Andreas Lanver, Klaus Ebel, Karl Beck, Ralf Pelzer, Jörg Botzem, Ulrich Griesbach
  • Publication number: 20120232267
    Abstract: A process continuously hydrogenating unsaturated compounds, in which particles of a first hydrogenation catalyst are suspended in a liquid phase in which an unsaturated compound is dissolved, the liquid phase, in the presence of a hydrogenous gas at a first partial hydrogen pressure and at a first temperature, is conducted through a packed bubble column reactor in cocurrent counter to the direction of gravity, the effluent from the bubble column reactor is sent to a gas-liquid separation, the liquid phase is sent to a crossfiltration to obtain a retentate and a filtrate, the retentate is recycled into the bubble column reactor and the filtrate, in the presence of a hydrogenous gas at a second partial hydrogen pressure and at a second temperature, is passed over a bed of a second hydrogenation catalyst, the second partial hydrogen pressure is at least 10 bar higher than the first partial hydrogen pressure.
    Type: Application
    Filed: March 19, 2012
    Publication date: September 13, 2012
    Applicant: BASF SE
    Inventors: Bram Willem Hoffer, Hartwig Voss, Ekkehard Schwab, Udo Rheude, Gerd Kaibel, Mathias Haake, Jan Eberhardt, Michael Karcher
  • Patent number: 8163963
    Abstract: A process is described for continuously hydrogenating unsaturated compounds, in which particles of a first hydrogenation catalyst are suspended in a liquid phase in which an unsaturated compound is dissolved, the liquid phase, in the presence of a hydrogenous gas at a first partial hydrogen pressure and at a first temperature, is conducted through a packed bubble column reactor in cocurrent counter to the direction of gravity, the effluent from the bubble column reactor is sent to a gas-liquid separation, the liquid phase is sent to a crossfiltration to obtain a retentate and a filtrate, the retentate is recycled into the bubble column reactor and the filtrate, in the presence of a hydrogenous gas at a second partial hydrogen pressure and at a second temperature, is passed over a bed of a second hydrogenation catalyst, wherein the second partial hydrogen pressure is at least 10 bar higher than the first partial hydrogen pressure.
    Type: Grant
    Filed: October 16, 2006
    Date of Patent: April 24, 2012
    Assignee: BASF SE
    Inventors: Bram Willem Hoffer, Hartwig Voβ, Ekkehard Schwab, Udo Rheude, Gerd Kaibel, Mathias Haake, Jan Eberhardt, Michael Karcher
  • Publication number: 20110196176
    Abstract: The invention relates to a process for the preparation of m-substituted alkyltoluenes of the formula (I) in which R1 is C1-C5-alkyl, wherein a p-substituted alkyltoluene of the formula (II) in which R1 has the meaning given under formula (I), is isomerized in the presence of ionic liquids to give an m-substituted alkyltoluene of the formula (I). The m-substituted alkyltoluenes obtainable according to the invention are starting compounds for the preparation of fragrances and aroma substances.
    Type: Application
    Filed: February 10, 2011
    Publication date: August 11, 2011
    Applicant: BASF SE
    Inventors: Andreas Lanver, Klaus Ebel, Karl Beck, Ralf Pelzer, Jörg Botzem, Ulrich Griesbach
  • Publication number: 20100256421
    Abstract: A product of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde, wherein m-tert-butylphenyl propionaldehyde is in an amount from 6% to 60% of the combination of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde. Also a method including; adding dropwise an aldehyde solution to a basic solution; and, collecting a fraction of p-tert-butyl cinnamic aldehyde m-tert-butyl cinnamic aldehyde therefrom; and, adding a transition metal catalyst to a solution of the p-tert-butyl cinnamic aldehyde in ethanol, and, collecting therefrom by distillation a product of p-tert-butylphenyl propionaldehyde and the meta isomer m-tert-butylphenyl propionaldehyde; wherein the product comprises m-tert-butylphenyl propionaldehyde in an amount from 6% to 60% of the combination of p-tert-butylphenyl propionaldehyde and m-tert-butylphenyl propionaldehyde.
    Type: Application
    Filed: March 23, 2010
    Publication date: October 7, 2010
    Applicant: O'LAUGHLIN INDUSTRIES, CO. LTD.
    Inventors: Zhiguo Gao, Jun Li, Xin Qi
  • Publication number: 20100081804
    Abstract: A process is described for continuously hydrogenating unsaturated compounds, in which particles of a first hydrogenation catalyst are suspended in a liquid phase in which an unsaturated compound is dissolved, the liquid phase, in the presence of a hydrogenous gas at a first partial hydrogen pressure and at a first temperature, is conducted through a packed bubble column reactor in cocurrent counter to the direction of gravity, the effluent from the bubble column reactor is sent to a gas-liquid separation, the liquid phase is sent to a crossfiltration to obtain a retentate and a filtrate, the retentate is recycled into the bubble column reactor and the filtrate, in the presence of a hydrogenous gas at a second partial hydrogen pressure and at a second temperature, is passed over a bed of a second hydrogenation catalyst, wherein the second partial hydrogen pressure is at least 10 bar higher than the first partial hydrogen pressure.
    Type: Application
    Filed: October 16, 2006
    Publication date: April 1, 2010
    Inventors: Bram Willem Hoffer, Hartwig Voss, Ekkehard Schwab, Udo Rheude, Gerd Kaibel, Mathias Haake, Jan Eberhardt, Michael Karcher
  • Patent number: 7538253
    Abstract: The present invention relates to a novel method for preparing a catalyst of the formula (1), WOx wherein, W represents tungsten atom, O represents oxygen atom x represents a value determined by oxidative state of W, for partial oxidation of methylbenzenes, the method comprising: (a) a step of preparing tungsten oxide slurry by wet milling; (b) a step of supporting the slurry obtained in the step (a) on fire-resistance inorganic carrier by impregnation; (c) a step of drying the catalyst obtained in the step (b); and (d) a step of calcining the dried catalyst obtained in the step (c), and can reduce the reaction temperature on the basis of equivalent yield in the preparation of corresponding aromatic aldehyde from methylbenzenes since the catalyst has increased the surface areas compared to the conventional one, and thus has high conversion rate.
    Type: Grant
    Filed: November 21, 2006
    Date of Patent: May 26, 2009
    Assignee: LG Chem Ltd.
    Inventors: Won Ho Lee, Dong Il Lee, Jong Hyun Chae, Hyun Kyung Yoon
  • Patent number: 7417171
    Abstract: The present invention relates to a method for preparing an aromatic dialdehyde, comprising, a) a step of gas phase oxidation reaction for preparing aromatic dialdehyde from dimethyl benzene; b) a step of separation for selectively recovering crude aromatic dialdehyde of molten phase from the reaction product of the step (a); and c) a step of purification for obtaining highly pure aromatic dialdehyde by purifying said crude aromatic dialdehyde, and a manufacturing system used for the preparation method. The method for preparation of the aromatic dialdehyde according to the present invention is simple, effective, and advantageous in that highly pure aromatic dialdehyde can be continuously prepared.
    Type: Grant
    Filed: December 13, 2006
    Date of Patent: August 26, 2008
    Assignee: LG Chem, Ltd.
    Inventors: Jong Hyun Chae, Won Ho Lee, Dong Il Lee, In Kyu Park, Yong Jin Choe, Sung Kyu Lee, Yeong Dae Kim, Jong Suh Park, Seong Hoon Kang
  • Patent number: 7087548
    Abstract: A process for preparing an Rh-based catalytic system heterogenized on an organic or mineral support, characterized in that: a) a rhodium derivative with a valency state>0 is reduced in an ether or aromatic solvent and in the presence of a compound chosen from the group consisting of lipophilic tertiary amines, lipophilic tertiary amides and lipophilic quaternary ammonium salts, and b) the mixture thus obtained is adsorbed onto a suitable organic or mineral support. Use of the abovementioned catalytic system to hydrogenate a C?C double bond of an ?,?-unsaturated carbonyl compound.
    Type: Grant
    Filed: October 24, 2002
    Date of Patent: August 8, 2006
    Assignee: Chemi Spa
    Inventors: Oreste Piccolo, Alessandra Verrazzani
  • Patent number: 6965055
    Abstract: A process for conveniently and efficiently producing a highly pure cinnamaldehyde derivative, for example, (2E)-(3-hydroxy-4-methoxy)cinnamaldehyde, which comprises reacting a benzaldehyde derivative, such as isovanillin and the like, with acetaldehyde in the presence of an alkali, in particular preferably, dropping acetaldehyde little by little thereto in an aqueous solution at a low temperature for the reaction thereof. The cinnamaldehyde derivative thus obtained is selectively reduced to produce 3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propionaldehyde. Further, through a reductive alkylation reaction of the compound thus produced with an aspartame, N-[N-[3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propyl]-L-?-aspartyl]-L-phenylalanine 1-methyl ester, which is useful as a sweetener having a high sweetening potency, can be industrially and efficiently produced. The processes therefor are also provided.
    Type: Grant
    Filed: November 18, 2002
    Date of Patent: November 15, 2005
    Assignee: Ajinomoto Co., Ltd.
    Inventors: Kenichi Mori, Shinji Fujita, Nao Funakoshi, Tadashi Takemoto
  • Patent number: 6723883
    Abstract: The present invention relates to a continuous process for the preparation of cinnamaldehyde or cinnamaldehyde derivatives by continuous reaction of benzaldehyde derivatives with alkanals in the presence of bases and optionally subsequent continuous hydrogenation in a circulation reactor in the presence of a suspension catalyst and hydrogen to give dihydrocinnamaldehyde derivatives.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: April 20, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Jörg Therre, Andreas Kramer, Andreas Weiper-Idelmann, Michael Schulik, Regina Benfer, Jürgen Schossig, Mathias Haake, Hans-Georg Göbbel
  • Patent number: 6458737
    Abstract: The present invention has for its object to provide a novel catalyst by use of which methylbenzenes can be oxidized in gaseous phase in the presence of molecular oxygen to give the corresponding aromatic aldehydes in high yields, a process for producing an aromatic aldehyde from the corresponding methylbenzene in a high yield by use of said catalyst, and a process for producing cyclohexanedimethanol which comprises hydrogenating phthalaldehyde among the aromatic aldehydes which can be obtained as above.
    Type: Grant
    Filed: November 13, 2000
    Date of Patent: October 1, 2002
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Nobuji Kishimoto, Isao Nakamura, Yusei Nagamura, Akiyoshi Nakajima, Masashi Hashimoto, Kunika Takahashi
  • Patent number: 5811588
    Abstract: Process for the preparation of 3-phenylpropanal in which cinnamaldehyde is hydrogenated with the aid of a Pd-containing catalyst in the presence of a small amount of water. A high yield and a high selectivity are obtained in a commercially attractive process. The reaction mixture obtained can without intermediate further processing be subjected to an oxidation in which the cinnamaldehyde is oxidized to 3-phenylpropionic acid with a high degree of conversion and a high selectivity. The combination of the two process steps constitutes a simple, commercially attractive process for the preparation of 3-phenylpropionic acid using cinnamaldehyde as a starting material. The resulting 3-phenyl-propionic acid product may serve as an intermediate reagent in the synthesis of anti-viral pharmaceuticals, particularly HIV protease inhibitors.
    Type: Grant
    Filed: April 16, 1997
    Date of Patent: September 22, 1998
    Assignee: DSM N.V.
    Inventors: Anna M. C. F. Castelijns, Johanna M. Hogeweg, Simon P. J. M. van Nispen
  • Patent number: 5650546
    Abstract: A process for the hydrogenation of organic compounds using water soluble catalyst in a biphasic media by: (A) forming an organo-water dispersion of (i) an organic phase having (a) an organic compound and (b) an organic solvent, and (ii) an aqueous phase having a water soluble group VIII metal catalyst composition and a water soluble ligand; and (B) contacting said dispersion with hydrogen to provide an interfacial reaction between said organic compound and said hydrogen, giving significant enhancement in the rate of reaction to produce saturated organic compound as compared to a reaction carried out in the absence of said water immiscible ligand.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: July 22, 1997
    Assignee: Council of Scientific Industrial Resear.
    Inventors: Raghunath Vitthal Chaudhari, Bhalchandra Mahadeo Bhanage, Sunil Sadashiv Divekar, Raj Madhukar Deshpande
  • Patent number: 5026919
    Abstract: Basic intermediate or large pore zeolites having a Constraint Index less than 12 are useful as catalysts in the dehydrogenation-aromatization of cyclie dienes, in the isomerization of olefins and in the aldol condensation, and particularly in the cyclization of acetonylacetone to 3-methyl-2-cyclopenten-1-one.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: June 25, 1991
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 5003110
    Abstract: Saturated aldehydes are prepared by hydrogenation of .alpha.,.beta.-unsaturated aldehydes in a two-phase medium in the presence of a catalyst consisting of a rhodium derivative combined with a water-soluble ligand or of a rhodium complex with a water-soluble ligand.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: March 26, 1991
    Assignee: Rhone-Poulenc Sante
    Inventor: Jean-Michel Grosselin
  • Patent number: 4782187
    Abstract: The preparation of 4,4'-stilbenedialdehydes from the corresponding acid chlorides in the presence of a noble metal catalyst.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: November 1, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Reinehr, Heinz Steiner
  • Patent number: 4778928
    Abstract: The preparation of 4,4'-stilbenedialdehydes by reduction of 4,4'-stilbenedinitriles with an aluminium hydride.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: October 18, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Dieter Reinehr
  • Patent number: 4605797
    Abstract: Selective hydrogenation process is provided employing as catalyst a composition consisting essentially of elemental palladium on calcium carbonate support with lead acetate and an aromatic amine oxide. Very high selectivities to cis-olefinic compounds from acetylenic compounds is achieved employing the catalyst of the invention.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: August 12, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4420648
    Abstract: Supported coprecipitated cobalt-silica hydrogenation catalysts are disclosed. The catalysts are prepared by: preparing an aqueous reaction mixture containing cobalt cations, silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the cobalt and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the cobalt and silicate ions onto said solid porous carrier particles. The aqueous reaction mixture may additionally include copper cations.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: December 13, 1983
    Assignee: Exxon Research and Engineering Co.
    Inventors: James L. Carter, Allan E. Barnett
  • Patent number: 4273945
    Abstract: Saturated aliphatic, cycloaliphatic and araliphatic aldehydes are prepared by selective hydrogenation of the corresponding olefinically unsaturated aldehydes with hydrogen in the liquid phase over a palladium-containing catalyst, using a catalyst system in which the active constituents are from 2 to 90% by weight of palladium and from 10 to 98% by weight of an oxide or a salt of a rare earth metal or of a mixture of different oxides and/or salts of this type.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: June 16, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Heilen, Axel Nissen, Wolfgang Koernig, Michael Horner, Werner Fliege, Guenter Boettger
  • Patent number: 4273944
    Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 16, 1981
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
  • Patent number: 4263225
    Abstract: Supported coprecipitated nickel-cobalt-silica and nickel-cobalt-copper-silica hydrogenation catalysts are disclosed. The catalysts are prepared by preparing an aqueous reaction mixture containing nickel and cobalt cations (and optionally copper cations), silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the nickel, cobalt (and optionally copper) and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the nickel, cobalt (and optionally copper) and silicate anions onto said solid porous carrier particles.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: April 21, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: James L. Carter, Allan E. Barnett, John H. Sinfelt
  • Patent number: 4260829
    Abstract: Carbonyl compounds R.sup.1 --CHR.sup.2 --CHR.sup.3 --CR.sup.4 O (I, R.sup.1 =H or an organic radical; R.sup.2 -R.sup.4 =H or C.sub.1 -C.sub.4 -alkyl) are prepared by selective hydrogenation of the .alpha.,.beta.-unsaturated carbonyl compounds R.sup.1 --CR.sup.2 =CR.sup.3 --CR.sup.4 O (II) in the liquid phase by means of hydrogen in the presence of a palladium catalyst and of from 15 to 50% by weight, based on (II), of a tertiary amine.
    Type: Grant
    Filed: August 17, 1979
    Date of Patent: April 7, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Axel Nissen, Peter R. Laurer, Matthias Irgang, Heinrich Pasedach
  • Patent number: 4238358
    Abstract: Anthranilic acid has been anchored to polystyrene, and rhodium, palladium, platinum and ruthenium complexes of this modified polystyrene have been prepared. These catalysts will reduce a variety of olefinic and aromatic hydrocarbons, and also nitrile, nitro and carbonyl functional groups, said carbonyl groups being present in either ketones or aldehydes.
    Type: Grant
    Filed: March 29, 1979
    Date of Patent: December 9, 1980
    Assignee: Western Kentucky University
    Inventors: Norman L. Holy, William A. Logan, Karl D. Stein