Reactant Contains -coo- Group Patents (Class 568/435)
  • Publication number: 20150141699
    Abstract: A process for pyrolyzing a coal feed is described. A coal feed is pyrolyzed into a coal tar stream and a coke stream in a pyrolysis zone. The coal tar stream is separated into at least a pitch stream comprising aromatic hydrocarbons. The pitch stream is reacted in a reaction zone to add at least one functional group to an aromatic ring of the aromatic hydrocarbons in the pitch stream. The functionalized pitch stream is recycled to the pyrolysis zone.
    Type: Application
    Filed: August 26, 2014
    Publication date: May 21, 2015
    Inventors: Paul T. Barger, Maureen L. Bricker, Joseph A. Kocal, Matthew Lippmann, Kurt M. Vanden Bussche
  • Patent number: 8921606
    Abstract: 3-[3-(Trifluoromethyl)phenyl]propionaldehyde is a key intermediate for the preparation of cinacalcet hydrochloride. The present invention provides a novel process for the preparation of 3-[3-(trifluoromethyl)phenyl]propionaldehyde. The present invention also provides an improved process for preparation of cinacalcet hydrochloride in high yields. The present invention further provides a process for purification of cinacalcet hydrochloride.
    Type: Grant
    Filed: July 16, 2010
    Date of Patent: December 30, 2014
    Assignee: Hetero Research Foundation
    Inventors: Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Dasari Muralidhara Reddy, Rapolu Raji Reddy, Jambula Mukunda Reddy, Bandi Vamsi Krishna
  • Publication number: 20130178654
    Abstract: 3-[3-(Trifluoromethyl)phenyl]propionaldehyde is a key intermediate for the preparation of cinacalcet hydrochloride. The present invention provides a novel process for the preparation of 3-[3-(trifluoromethyl)phenyl]propionaldehyde. The present invention also provides an improved process for preparation of cinacalcet hydrochloride in high yields. The present invention further provides a process for purification of cinacalcet hydrochloride.
    Type: Application
    Filed: July 16, 2010
    Publication date: July 11, 2013
    Applicant: HETERO RESEARCH FOUNDATION
    Inventors: Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Dasari Muralidhara Reddy, Rapolu Raji Reddy, Jambula Mukunda Reddy, Bandi Vamsi Krishna
  • Publication number: 20130123546
    Abstract: A process for the preparation of an aromatic aldehyde by means of the oxidation of the corresponding starting compound in aqueous medium, and separation of said aldehyde from said medium by pervaporation is disclosed together a plant for its carrying out. Advantageously, the process of the present invention allows control of oxidation reaction and recovery of the product with high selectivity and purity. Among others, benzaldehyde, anisaldehyde and vanillin can advantageously be prepared by this process.
    Type: Application
    Filed: June 10, 2011
    Publication date: May 16, 2013
    Applicant: ALMA MATER STUDIORUM UNIVERSITA DI BOLOGNA
    Inventors: Giovanni Camer Roda, Vincenzo Augugliaro, Vittorio Loddo, Giovanni Palmisano, Leonardo Palmisano
  • Patent number: 8431750
    Abstract: Hydroxyaromatic aldehydes are prepared by oxidation of a corresponding mandelic derivative carried out in a basic medium and in the presence of a catalytic system containing at least two metal elements.
    Type: Grant
    Filed: June 3, 2008
    Date of Patent: April 30, 2013
    Assignee: Rhodia Operations
    Inventors: Christian Maliverney, Jean-Christophe Bigouraux, Laurent Garel
  • Patent number: 8338649
    Abstract: The invention relates to a method for the production of an aromatic carbonyl compound by the oxidation of a methyl group or methylene group bonded to the aromatic group in which the aromatic substance is reacted in the presence of an oxidizing agent and a sulphoxide, a sulphoxide being selected for the oxidation of a specific aromatic substance whose ionization potential, in terms of magnitude, differs from the ionization potential of the aromatic substance to be oxidized by a maximum of ±0.25 eV.
    Type: Grant
    Filed: September 2, 2008
    Date of Patent: December 25, 2012
    Assignee: Weylchem Frankfurt GmbH
    Inventors: Klaus Forstinger, Thomas Sommer, Daniel Decker, Andreas Martin, Angela Köckritz, Michael Kant, Alexander Hofmann
  • Patent number: 8124813
    Abstract: The invention relates to a novel process for preparing 2-phenoxyacetals and the corresponding 2-phenoxycarbaldehydes. These compounds are important intermediates for the preparation of active pharmaceutical ingredients.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: February 28, 2012
    Assignee: SALTIGO GmbH
    Inventors: Thomas-Norbert Müller, Michael Dockner
  • Publication number: 20110306802
    Abstract: Hydroxyaromatic aldehydes are prepared by oxidation of a corresponding mandelic derivative carried out in a basic medium and in the presence of a catalytic system containing at least two metal elements.
    Type: Application
    Filed: June 3, 2008
    Publication date: December 15, 2011
    Inventors: Christian Maliverney, Jean-Christophe Bigouraux, Laurent Garel
  • Publication number: 20110009664
    Abstract: The invention relates to a method for preparing optionally substituted P-hydroxymandelic compounds and derivatives thereof. The method for preparing the mandelic compounds of the invention comprises condensing in water, in the presence of an alkaline agent, an aromatic compound bearing at least one hydroxyl group and having a free para position, with glycoxylic acid, wherein said method is characterised in that said reaction is carried out in a piston-flow reactor.
    Type: Application
    Filed: December 9, 2008
    Publication date: January 13, 2011
    Applicant: Rhodia Pperations
    Inventors: Bruno Heinisch, Pascal Pitiot, Jean-Louis Grieneisen
  • Publication number: 20100317869
    Abstract: To provide a solid catalyst containing a cyclic imide skeleton which is easily available and easily separable from reaction products and which is easily recovered and regenerated, and free from reaction inhibitory factors; and a process for oxidation of organic compounds with the solid catalyst. An immobilized cyclic imide catalyst having a structure represented by following Formula (1), wherein X is oxygen or an —OR group (wherein R is hydrogen atom or a hydroxyl-protecting group); n is 0 or 1; Z1 is a five- or six-membered cyclic imide skeleton to which an aromatic or nonaromatic ring Z2 may be adjacent; elliptically shaped moiety S is an inorganic support; A1 is a group linking silicon atom with the cyclic imide skeleton Z1 or with the ring Z2 and is either a divalent hydrocarbon group or a group composed of a divalent hydrocarbon group and an amide bond (—NHCO—); and the cyclic imide skeleton Z1 and the ring Z2 may each be substituted.
    Type: Application
    Filed: February 28, 2008
    Publication date: December 16, 2010
    Inventors: Yasutaka Ishii, Minoru Takano, Naruhisa Hirai
  • Publication number: 20100286449
    Abstract: The invention relates to a novel process for preparing 2-phenoxyacetals and the corresponding 2-phenoxycarbaldehydes. These compounds are important intermediates for the preparation of active pharmaceutical ingredients.
    Type: Application
    Filed: June 11, 2008
    Publication date: November 11, 2010
    Applicant: SALTIGO GMBH
    Inventors: Thomas-Norbert Mueller, Michael Dockner
  • Publication number: 20100234589
    Abstract: In a process for oxidizing a hydrocarbon to a corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I): wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH and NO2, or from the atoms H, F, Cl, Br and I provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N and CR3; each of X and Z is independently selected from C, S, CH2, N, P and an element of Group 4 of the Periodic Table; Y is O or OH; k is 0, 1, or 2; 1 is 0, 1, or 2; m is 1 to 3, and R3 can be any of the entities listed for R1.
    Type: Application
    Filed: July 11, 2008
    Publication date: September 16, 2010
    Inventors: Jihad M. Dakka, James C. Vartuli, Stephen Zushma
  • Patent number: 7498454
    Abstract: A fatty acid alkyl ester of the general formula I: and acrolein are prepared by reacting a triglyceride of the general formula II: wherein a) the triglyceride is reacted using an alcohol R?—OH in the presence of a catalyst to give said fatty acid alkyl ester and glycerol; and b) the glycerol is dehydrated catalytically to acrolein, wherein R is R1, R2 and R3, and R1, R2 and R3 are all the same or some are the same or all are different and are each a straight-chain or branched, and optionally mono- or polyunsaturated C10-C30-alkyl radical, and R? is a C1-C10-alkyl radical or a C3-C6-cycloalkyl radical.
    Type: Grant
    Filed: November 20, 2007
    Date of Patent: March 3, 2009
    Assignee: Evonik Degussa GmbH
    Inventors: Hubert Redlingshoefer, Christoph Weckbecker, Klaus Huthmacher
  • Patent number: 7399889
    Abstract: The present invention provides a process for the preparation of Vanillin (4-hydroxy-3-methoxy benzaldehyde) by a single-step oxidation of ferulate moiety of rice straw, a renewable agricultural waste. This is a chemical method where vanillin is produced from a renewable resource in a single-step using a green oxidizing reagent and green solvent. Apart from that the water and the inorganic compounds can be recycled.
    Type: Grant
    Filed: February 12, 2007
    Date of Patent: July 15, 2008
    Assignee: Council of Scientific and Industrial Research
    Inventor: Naleen Borthakur
  • Patent number: 6933405
    Abstract: The present invention is a user- and eco-friendly hypervalent iodine reagent (mIBX) capable of selectively oxidizing allylic and benzylic alcohols in water and other eco-friendly solvents and having generally the following structure: Allylic and benzylic alcohols are cleanly oxidized to the corresponding carbonyl compounds in water or water-THF mixtures, or other mixtures, using a water-soluble o-iodoxybenzoic acid derivative of the present invention.
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: August 23, 2005
    Assignee: Board of Trustees of Western Illinois University
    Inventors: Thottumkara K. Vinod, Arun P. Thottumkara
  • Patent number: 6906207
    Abstract: Plastic additives which are useful as nucleating agents and which are especially useful for improving the optical properties of polymeric materials are provided. More particularly, this invention relates to certain alkyl (or alkoxy) substituted fluoro-benzylidene sorbitol acetals and polymer compositions thereof which may be utilized within, as merely examples, food or cosmetic containers and packaging. These inventive fluorinated and alkylated benzylidene sorbitol acetals are also useful as gelling agents for water and organic solvents, particularly those used in the preparation of antiperspirant gel sticks.
    Type: Grant
    Filed: January 7, 2003
    Date of Patent: June 14, 2005
    Assignee: Milliken & Company
    Inventors: John D. Anderson, Nathan A. Mehl
  • Patent number: 6790964
    Abstract: The present invention provides a method of producing 7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ester (VII) economically, industrially advantageously and efficiently in a large amount.
    Type: Grant
    Filed: August 13, 2002
    Date of Patent: September 14, 2004
    Assignees: Sagami Chemical Research Center, Kuraray Co., Ltd.
    Inventors: Shiro Terashima, Katsuji Ujita, Akihiro Ishiwata
  • Patent number: 6787671
    Abstract: An osmium-assisted process for the oxidative cleavage of oxidizable organic compounds such as unsaturated organic compounds, including alkenes and olefins into aldehydes, carboxylic acids, esters, or ketones. The process uses a metal catalyst comprising osmium and a peroxy compound selected from the group consisting of peroxymonosulfuric acid and salts thereof to oxidatively cleave the oxidizable organic compound. In particular, the process enables aldehydes, carboxylic acids, esters, or ketones to be selectively produced from the corresponding mono-, 1,1-di-, 1,2-di-, tri-, or tetra-substituted olefins in a reaction that produces the result of ozonolysis but with fewer problems. The present invention further provides a process for oxidizing an aldehyde alone or with the osmium in an interactive solvent to produce an ester or carboxylic acid.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: September 7, 2004
    Assignee: Board of Trustees of Michigan State University
    Inventors: Babak Borhan, Benjamin R. Travis, Jennifer M. Schomaker
  • Patent number: 6673856
    Abstract: The present invention relates to improved alditol acetal compositions, in particular 1,3-2,4-di(benzylidene) sorbitol (DBS) or one of its alkylated derivatives. The improvement in these compositions is expressed in particular in terms of flow behavior and/or thermal stability. It is obtained by combining the alditol acetal with an additive selected from tocopherols, polyols and certain of their respective derivatives. These additives may act as binding or densifying agents and/or stabilizing agents or odor maskers. The alditol acetal and additive are advantageously combined by cold mixing, followed by granulation or compaction, also cold. The compositions of the invention, for example based on DBS or the methylated derivatives of DBS, are in the form of densified or compacted powders, granules, pellets, pastilles or extrudates. They are used in particular for preparing plastic or jellified materials or additives for these types of materials.
    Type: Grant
    Filed: September 22, 1999
    Date of Patent: January 6, 2004
    Assignee: Roquette Freres
    Inventor: Léon Mentink
  • Patent number: 6624330
    Abstract: The present invention relates to a method for stabilizing phenylacetaldehyde by adding at least one additive, in which case the additive contains one or more polybasic carboxylic acids.
    Type: Grant
    Filed: December 4, 2001
    Date of Patent: September 23, 2003
    Assignee: Haarmann & Reimer GmbH
    Inventor: Walter Kuhn
  • Publication number: 20030144558
    Abstract: The invention relates to a method for producing optionally substituted aliphatic, aromatic or heteraromatic aldehydes of formula (I), whereby the R represents a C1-C20 Alkyl radical, an aromatic or heteraromatic radical Ar which can optionally be substituted once or on a number of occasions by OH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 carboxylic acids or ester containing 1-6 C atoms in the ester part, phenyl, halogen, SO3H, NO2, NR1R2 or SR1 whereby R1 and R2 can be independently H, phenyl or C1-C6 alkyl. The invention is characterised by a compound of formula (II) wherein R has the above meaning, a) is diazotized in an acidic medium, at a temperature of between −10 −+100 ° C. by a diazoation reagent and is transformed into the corresponding hydroxy carboxy acid whereby b) is transformed, by means of oxygen, into the appropriate aldehyde of formula (I) in the presence of a metal, the salt thereof, oxide or hydroxide as a catalyst.
    Type: Application
    Filed: December 13, 2002
    Publication date: July 31, 2003
    Inventors: Wolfram Hendel, Ferdinand Heu, Peter Poechlauer, Berthold WInkler
  • Patent number: 6596906
    Abstract: The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: July 22, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Käthe Baumann, Albrecht Marhold
  • Publication number: 20030032842
    Abstract: 3-(3-Methyl-4-hydroxyphenyl)-3-methylbutyl aldehyde may be produced from 3-(3-methyl-4-hydroxyphenyl)-3-methylbutyric acid by converting the carboxyl group into a formyl group. N-[N-[3-(3-methyl-4-hydroxyphenyl)-3-methylbutyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, which is useful as a sweetener having a high potency of sweetness, can be easily and efficiently prepared on an industrial production from such an aldehyde derivative, via a reductive alkylation reaction with aspartame. Therefore, 3-(3-Methyl-4-hydroxyphenyl)-3-methylbutyl aldehyde is extremely excellent as an intermediate for the production of N-[N-[3-(3-methyl-4-hydroxyphenyl)-3- methylbutyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester.
    Type: Application
    Filed: July 19, 2002
    Publication date: February 13, 2003
    Applicant: Ajinomoto Co., Inc.
    Inventors: Kenichi Mori, Shigeru Kawahara, Tadashi Takemoto
  • Patent number: 6441243
    Abstract: The invention relates to a process for the selective oxidation of alcohols to ketones or to aldehydes by means of an alkali hypohalite under alkaline conditions, which comprises carrying out the oxidation in the presence of a heterogeneous oxidation catalyst that is insoluble in the reaction medium and is selected from the group comprising the compounds of formula (I) (III), wherein n is a number from 3 to 3000; or a 4-oxy-2,2,6,6-tetramethylpiperidin-1-oxyl that is 4-oxy-bound to a Merrifield polymer. The invention relates also to the compounds of formulae (II) and (III) and to the use of the above-mentioned oxidation catalysts for the oxidation of alcohols.
    Type: Grant
    Filed: November 15, 2000
    Date of Patent: August 27, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Reinhard Sommerlade, Hansjörg Grützmacher, Souâd Boulmaâz
  • Patent number: 6331655
    Abstract: The present invention relates to a novel process for the preparation of aromatic carbonyl compounds by oxidative cleavage of styrenes using lipases and hydrogen peroxide or hydrogen peroxide donors in the presence of carboxylic acids or carboxylic esters.
    Type: Grant
    Filed: June 9, 2000
    Date of Patent: December 18, 2001
    Assignee: Haarmann & Reimer GmbH
    Inventors: Ian-Lucas Gatfield, Jens-Michael Hilmer
  • Patent number: 6300525
    Abstract: A process for the preparation of aromatic aldehydes containing fluorine, and more particularly, to a formylation process for fluorinated aromatic derivatives through the reaction of fluorinated benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, a low temperature, and in the presence of at most a catalytic amount of an acid (such as aqueous hydrochloric acid) is herein disclosed. The resultant fluorinated benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, herbicidal compounds, nucleating agents, polymer additives, and the like. The inventive method provides a very cost effective and safe procedure for producing such fluorinated benzaldehydes in very high yields.
    Type: Grant
    Filed: September 1, 2000
    Date of Patent: October 9, 2001
    Assignee: Milliken & Company
    Inventors: John David O. Anderson, Walter A. Scrivens
  • Patent number: 6297405
    Abstract: A process for the preparation of aromatic aldehydes containing fluorine, and more particularly, to a formylation process for fluorinated aromatic derivatives through the reaction of fluorinated benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, a low temperature, and in the presence of at most a catalytic amount of an acid (such as aqueous hydrochloric acid) is herein disclosed. The resultant fluorinated benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, herbicidal compounds, nucleating agents, polymer additives, and the like. The inventive method provides a very cost effective and safe procedure for producing such fluorinated benzaldehydes in very high yields. The particular novel multi-substituted benzaldehydes are also encompassed within this invention.
    Type: Grant
    Filed: September 1, 2000
    Date of Patent: October 2, 2001
    Assignee: Milliken & Company
    Inventors: John David O. Anderson, Walter Scrivens
  • Patent number: 6180830
    Abstract: The present invention relates to a new process for the preparation of a bimetallic ruthenium/tin catalyst. The process for the preparation of a bimetallic ruthenium/tin catalyst according to the invention is characterised by the fact that it consists in carrying out the reduction of a ruthenium complex having an electrovalency of −4 and a coordination number of 6, the ligands being either a halogen atom or an anion or a tin halide. The catalyst is further employed for the preparation of aldehydes by reduction, in the vapor phase, of carboxylic acids, esters and anhydrides.
    Type: Grant
    Filed: May 5, 1998
    Date of Patent: January 30, 2001
    Assignee: Rhodia Chimie
    Inventor: Roland Jacquot
  • Patent number: 5977414
    Abstract: 2,3-Dihalogeno-6-trifluoromethylbenzaldehydes of general formula (I) useful as intermediates for the preparation of fungicides for agricultural and horticultural use;a process for the preparation of the same; and process for preparing 2,3-dihalogeno-6-trifluoromethylbenzamidoximes of general formula (IV) from the above compounds, wherein X.sup.1 and X.sup.2 are each independently fluoro, chloro or bromo.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: November 2, 1999
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Takashi Okabe, Isamu Kasahara, Tatsumi Suzuki
  • Patent number: 5763676
    Abstract: Aromatic aldehydes are prepared by catalytically reacting aromatic carboxylic acids or their esters with hydrogen in the gas phase at from 200.degree. to 450.degree. C. and from 0.1 to 20 bar in the presence of a zirconium dioxide/lanthanide catalyst having a high BET surface area of from 20 to 150 m.sup.2 /g, preferably from 40 to 150 m.sup.2 /g. The proportions by weight of the catalytically active mass range from 80 to 99.9% by weight of zirconium dioxide and from 0.01 to 20 %by weight of one or more lanthanide elements. This catalyst provides very high conversion rates of 94 to 100% together with a correspondingly high selectivity for the aldehyde product.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: June 9, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Matthias Irgang, Werner Schnurr, Joachim Wulff-Doring
  • Patent number: 5679869
    Abstract: A process for preparing aldehydes of the general formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.12 -alkylphenyl, C.sub.7 -C.sub.12 -phenylalkyl and R.sup.1 and R.sup.2 are joined together to form a 3-, 4-, 5-, 6- or 7-membered cycloaliphatic ring,R.sup.1 and R.sup.3 are each C.sub.1 -C.sub.4 -alkoxy, phenoxy, methylamino, dimethylamino or halogen, andR.sup.1 is additionally hydroxyl or aminocomprises reacting a carboxylic acid or ester of the general formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each as defined above, andR.sup.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.12 -alkylphenyl or C.sub.7 -C.sub.12 -phenylalkyl,with hydrogen in the gas phase at temperatures from 200.degree. to 450.degree. C. and pressures from 0.1 to 20 bar in the presence of a catalyst whose catalytically active mass comprises from 60 to 99.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: October 21, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Schnurr, Rolf Fischer, Joachim Wulff-Doring, Michael Hesse
  • Patent number: 5585523
    Abstract: Process for the preparation of aldehydes by catalytic gas phase hydrogenation of carboxylic acid or their derivatives with the aid of a tin catalystThe invention relates to a process for the preparation of aldehydes by catalytic gas phase hydrogenation of carboxylic acids or carboxylic acid derivatives at elevated temperature, which comprises employing at tin catalyst supplied to an oxidic support material.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: December 17, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jens Weiguny, Holger Borchert, Thomas Gerdau
  • Patent number: 5527769
    Abstract: The compounds of formula ##STR1## wherein symbol X represents a --CHO group or an acetal group of formula ##STR2## symbols R', taken separately, represent each a C.sub.1 to C.sub.4, linear or branched, saturated or unsaturated, hydrocarbon radical or, taken together, represent a C.sub.1 to C.sub.4 alkylene radical, which may be substituted, and symbol R represents a hydrogen atom or a methyl radical, are useful as perfuming ingredients for the preparation of perfuming compositions and perfumed articles, to which they impart floral type notes.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: June 18, 1996
    Assignee: Firmenich SA
    Inventors: Beat Winter, George Skouroumounis
  • Patent number: 5336810
    Abstract: The invention relates to a catalyst that is very suitable for the conversion of a benzoic acid into the corresponding benzaldehyde. The catalyst can be obtained via coprecipitation of a manganese salt, a salt from which an acid support is formed, a zinc salt and optionally a copper salt at a pH between 4 and 10, calcination, after precipitation, of the coprecipitate at a temperature of between 300 and 700.degree. C. and then, optionally, reduction of the calcined coprecipitate with the aid of a hydrogen-containing gas mixture. Using such a catalyst the hydrogenation of a benzoic acid can be carried out at lower temperature resulting in energy-savings and, hence, cost-savings.
    Type: Grant
    Filed: May 7, 1993
    Date of Patent: August 9, 1994
    Assignee: DSM N.V.
    Inventors: Paul C. Van Geem, Xiaoding Xu, Joseph J. F. Scholten
  • Patent number: 5334769
    Abstract: The present invention relates to a process for the preparation of aldehydes by hydrogen reduction of carboxylic acids, esters or anhydrides, characterized in that the reduction is conducted in the vapour phase, in the presence of a bimetallic catalyst of the ruthenium/tin type.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: August 2, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Rose-Marie Ferrero, Roland Jacquot
  • Patent number: 5306845
    Abstract: A method for producing an aldehyde, which comprises hydrogenating a carboxylic acid or its alkyl ester with molecular hydrogen in the presence of a catalyst, wherein (1) chromium oxide of high purity having a specific surface area of at least 10 m.sup.2 /g and a total content of sodium, potassium, magnesium and calcium of not more than 0.4 wt %, is used as the catalyst, and (2) the hydrogenation reaction is conducted while maintaining the carboxylic acid or its alkyl ester at a concentration of not more than 10 vol %.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: April 26, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Toshiharu Yokohama, Naoko Fujita, Takao Maki
  • Patent number: 5260487
    Abstract: A method for the preparation of a 2-hydroxyarylaldehyde which comprises reacting a magnesium bis-hydrocarbyloxide derived at least in part from a hydroxyaromatic compound having at least one free position ortho to the hydroxyl group with formaldehyde or formaldehyde-liberating compound under substantially anhydrous conditions.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: November 9, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: Daniel Levin
  • Patent number: 5258544
    Abstract: Disclosed is a process for the preparation of 2-aryl-1-cyclohexene-1-carboxaldehydes from 1-arylcyclohexenes which are intermediates for trans-6-[(2-arylsubstituted cycloalkenyl and substituted cycloalkyl)alkenyl and alkyl]-3,4,5,6-tetrahydro-2H-pyran-2-ones.
    Type: Grant
    Filed: March 5, 1991
    Date of Patent: November 2, 1993
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Laurence W. Reilly, Jr., Ching T. Tsuei, Walter Rodriquez, Thomas Goetzen
  • Patent number: 5248816
    Abstract: A method for the preparation of a 2-hydroxymandelic acid of the formula ##STR1## wherein R represents an alkyl radical containing from 7 to 12 carbon atoms which comprises reacting glyoxylic acid with a phenol of the formula: ##STR2## under acid conditions. Oxidation of the 2-hydroxymandelic acid to the corresponding 2-hydroxybenzaldehyde is also described.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: September 28, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ralph Shuttleworth, Jan M. Fielden, Daniel Levin
  • Patent number: 5183931
    Abstract: Oxidation of alkylaromatics having a benzylic hydrogen atom is catalyzed by a catalyst comprising a palladium salt, a metal persulfate, a third metal salt, and a tin salt in a carboxylic acid for a period of time sufficient to convert the alkylaromatics to their corresponding oxidized derivatives. The catalyst is prepared by preheating the palladium salt and the metal persulfate at a temperature sufficient to provide the desired catalytic activity followed by additon of the third metal salt and the tin salt.
    Type: Grant
    Filed: February 10, 1992
    Date of Patent: February 2, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Chung C. Tso, Robert L. Wynn
  • Patent number: 5155278
    Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a non-basic polar solvent, in the presence of an oxidant, for about eight hours or less at a temperature in the range of from about -10.degree. C. to about 25.degree. C., and thereafter separating out the aldehyde.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: October 13, 1992
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 5138099
    Abstract: 4-fluorobenzaldehydes are formed from compounds of the formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different, and represent H, halogen, or an alkyl group of from 1 to about 10 carbon atoms, wherein, when at least one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is halogen, at least one of remaining R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is alkyl. the compound of formula of (I) is reacted with a formylating agent in the presence of FeCl.sub.3 in a reaction mixture, from which is separated a compound of the formula (II) ##STR2## wherein R.sub.1, R.sub.2 , R.sub.3 and R.sub.4 are as defined above.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: August 11, 1992
    Assignee: Mallinckrodt Specialty Chemicals Company
    Inventor: John F. Lang
  • Patent number: 5107032
    Abstract: A process for the preparation of o-phthalaldehydes is disclosed comprising the steps of (1) halogenating an o-xylene and (2) hydrolysis of the resulting tetrahalogeno-o-xylene.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: April 21, 1992
    Assignee: Noramco, Inc.
    Inventors: Dudley K. Erb, Janet E. Goldstein
  • Patent number: 5084259
    Abstract: The preparation, structure, and properties of solid inorganic materials containing aluminum, boron, oxygen and at least one Group VIII metallo element, selected from the group consisting of cobalt and nickel is described. Also described in the use of such materials in catalytic compositions for the conversion of organic compounds. In particular, the new materials having the general formula:(x) (M.sub.m :M'.sub.n)O.(y)Al.sub.2 O.sub.3.(z)B.sub.2 O.sub.
    Type: Grant
    Filed: March 15, 1991
    Date of Patent: January 28, 1992
    Assignee: Amoco Corporation
    Inventors: Larry C. Satek, Stephen T. McKenna, Vincent F. Smith, Jr.
  • Patent number: 5072008
    Abstract: The invention concerns a novel process for the stereospecific manufacture of novel hydroxymethyl lactols of the formula I by a one step reduction of a corresponding lactone carboxylic ester of the formula II (many of which esters are novel) using a reducing agent such as diisobutylaluminium hydride at about ambient temperature. The lactols of formula I are intermediates for the production of pharmacologically active 1,3-dioxane alkenoic acids useful in the treatment of certain cardiovascular and pulmonary medical conditions. Certain of the esters of formula II are novel and are also included in the invention.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: December 10, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Gregory D. Harris
  • Patent number: 5068450
    Abstract: A process for the preparation of aromatic aldehydes by formylation of aromatic compounds in liquid hydrofluoric acid in the presence of boron trifluoride.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: November 26, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Crochemore, Christophe Rochin
  • Patent number: 5059716
    Abstract: Aromatic and aliphatic aldehydes can be prepared from the corresponding aromatic or aliphatic carboxylic acids or the esters, anhydrides or halides thereof at elevated temperature by catalytic gas phase hydrogenation using hydrogen if use is made of a catalyst system composed of oxides of titanium and/or vanadium and of one or more co-metals, the co-metals being selected from the group consisting of chromium, molybdenum, cobalt, nickel, zinc, cadmium and copper.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: October 22, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Winfried Joentgen, Helmut Fiege
  • Patent number: 5057624
    Abstract: New process for the synthesis of the N-methyl-3,4-dimetoxyphenylethylamine of formula ##STR1## intermediate in the synthesis of the drug internationally known as verapamil. The process starts from the 3,4-dimethoxybenzaldehyde which, by means of a Darzens condensation, gives an epoxyester that, by alkaline hydrolysis and subsequent decarboxylation, gives the 3,4-dimethoxyphenylacetaldehyde. This aldehyde gives the amine of formula I by reaction with monomethylamine followed by reduction with sodium borohydride.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: October 15, 1991
    Assignee: ALFA Wassermann S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
  • Patent number: 5053552
    Abstract: The present invention provides a novel process for producing .alpha.,.beta.-unsaturated aldehydes including industrial important fragrances such as citral and sinensal, starting materials for preparing pharmaceutical drugs such as senecioaldehyde, farnesal, 8-acetoxy-2,6-dimethyl-2,6-octadienal and the like, directly and in high yield, from formic acid esters of allylic alcohols in the presence of a catalytic amount of aluminum alkoxide by the oxidation of the corresponding alehyde.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: October 1, 1991
    Assignee: Kuraray Company, Ltd.
    Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
  • Patent number: 4990684
    Abstract: Phenylacetaldehydes of the general formula I ##STR1## where each of R.sup.1 to R.sup.5 is independently of the others hydrogen, halogen, unsubstituted or halogen-substituted alkyl, alkenyl, alkoxyl, alkylthio or cycloalkyl, are prepared by converting glycidic esters of the general formula II ##STR2## where each of R.sup.1 to R.sup.5 is as defined above and R.sup.6 is tertbutyl or i-propyl, in the presence of zeolites and/or phosphates and/or phosphoric or boric acid on a carrier material and/or acidic metal oxides as catalysts.
    Type: Grant
    Filed: July 12, 1989
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer