Reactant Contains -coo- Group Patents (Class 568/435)
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Publication number: 20150141699Abstract: 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: ApplicationFiled: August 26, 2014Publication date: May 21, 2015Inventors: Paul T. Barger, Maureen L. Bricker, Joseph A. Kocal, Matthew Lippmann, Kurt M. Vanden Bussche
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Patent number: 8921606Abstract: 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: GrantFiled: July 16, 2010Date of Patent: December 30, 2014Assignee: Hetero Research FoundationInventors: Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Dasari Muralidhara Reddy, Rapolu Raji Reddy, Jambula Mukunda Reddy, Bandi Vamsi Krishna
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Publication number: 20130178654Abstract: 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: ApplicationFiled: July 16, 2010Publication date: July 11, 2013Applicant: HETERO RESEARCH FOUNDATIONInventors: Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Dasari Muralidhara Reddy, Rapolu Raji Reddy, Jambula Mukunda Reddy, Bandi Vamsi Krishna
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Publication number: 20130123546Abstract: 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: ApplicationFiled: June 10, 2011Publication date: May 16, 2013Applicant: ALMA MATER STUDIORUM UNIVERSITA DI BOLOGNAInventors: Giovanni Camer Roda, Vincenzo Augugliaro, Vittorio Loddo, Giovanni Palmisano, Leonardo Palmisano
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Patent number: 8431750Abstract: 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: GrantFiled: June 3, 2008Date of Patent: April 30, 2013Assignee: Rhodia OperationsInventors: Christian Maliverney, Jean-Christophe Bigouraux, Laurent Garel
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Patent number: 8338649Abstract: 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: GrantFiled: September 2, 2008Date of Patent: December 25, 2012Assignee: Weylchem Frankfurt GmbHInventors: Klaus Forstinger, Thomas Sommer, Daniel Decker, Andreas Martin, Angela Köckritz, Michael Kant, Alexander Hofmann
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Patent number: 8124813Abstract: 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: GrantFiled: June 11, 2008Date of Patent: February 28, 2012Assignee: SALTIGO GmbHInventors: Thomas-Norbert Müller, Michael Dockner
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Publication number: 20110306802Abstract: 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: ApplicationFiled: June 3, 2008Publication date: December 15, 2011Inventors: Christian Maliverney, Jean-Christophe Bigouraux, Laurent Garel
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Publication number: 20110009664Abstract: 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: ApplicationFiled: December 9, 2008Publication date: January 13, 2011Applicant: Rhodia PperationsInventors: Bruno Heinisch, Pascal Pitiot, Jean-Louis Grieneisen
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Publication number: 20100317869Abstract: 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: ApplicationFiled: February 28, 2008Publication date: December 16, 2010Inventors: Yasutaka Ishii, Minoru Takano, Naruhisa Hirai
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Publication number: 20100286449Abstract: 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: ApplicationFiled: June 11, 2008Publication date: November 11, 2010Applicant: SALTIGO GMBHInventors: Thomas-Norbert Mueller, Michael Dockner
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Publication number: 20100234589Abstract: 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: ApplicationFiled: July 11, 2008Publication date: September 16, 2010Inventors: Jihad M. Dakka, James C. Vartuli, Stephen Zushma
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Patent number: 7498454Abstract: 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: GrantFiled: November 20, 2007Date of Patent: March 3, 2009Assignee: Evonik Degussa GmbHInventors: Hubert Redlingshoefer, Christoph Weckbecker, Klaus Huthmacher
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Patent number: 7399889Abstract: 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: GrantFiled: February 12, 2007Date of Patent: July 15, 2008Assignee: Council of Scientific and Industrial ResearchInventor: Naleen Borthakur
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Patent number: 6933405Abstract: 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: GrantFiled: July 31, 2003Date of Patent: August 23, 2005Assignee: Board of Trustees of Western Illinois UniversityInventors: Thottumkara K. Vinod, Arun P. Thottumkara
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Patent number: 6906207Abstract: 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: GrantFiled: January 7, 2003Date of Patent: June 14, 2005Assignee: Milliken & CompanyInventors: John D. Anderson, Nathan A. Mehl
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Patent number: 6790964Abstract: 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: GrantFiled: August 13, 2002Date of Patent: September 14, 2004Assignees: Sagami Chemical Research Center, Kuraray Co., Ltd.Inventors: Shiro Terashima, Katsuji Ujita, Akihiro Ishiwata
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Patent number: 6787671Abstract: 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: GrantFiled: January 13, 2003Date of Patent: September 7, 2004Assignee: Board of Trustees of Michigan State UniversityInventors: Babak Borhan, Benjamin R. Travis, Jennifer M. Schomaker
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Patent number: 6673856Abstract: 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: GrantFiled: September 22, 1999Date of Patent: January 6, 2004Assignee: Roquette FreresInventor: Léon Mentink
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Patent number: 6624330Abstract: 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: GrantFiled: December 4, 2001Date of Patent: September 23, 2003Assignee: Haarmann & Reimer GmbHInventor: Walter Kuhn
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Publication number: 20030144558Abstract: 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: ApplicationFiled: December 13, 2002Publication date: July 31, 2003Inventors: Wolfram Hendel, Ferdinand Heu, Peter Poechlauer, Berthold WInkler
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Patent number: 6596906Abstract: 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: GrantFiled: September 21, 2001Date of Patent: July 22, 2003Assignee: Bayer AktiengesellschaftInventors: Käthe Baumann, Albrecht Marhold
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Publication number: 20030032842Abstract: 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: ApplicationFiled: July 19, 2002Publication date: February 13, 2003Applicant: Ajinomoto Co., Inc.Inventors: Kenichi Mori, Shigeru Kawahara, Tadashi Takemoto
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Patent number: 6441243Abstract: 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: GrantFiled: November 15, 2000Date of Patent: August 27, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Reinhard Sommerlade, Hansjörg Grützmacher, Souâd Boulmaâz
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Patent number: 6331655Abstract: 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: GrantFiled: June 9, 2000Date of Patent: December 18, 2001Assignee: Haarmann & Reimer GmbHInventors: Ian-Lucas Gatfield, Jens-Michael Hilmer
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Patent number: 6300525Abstract: 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: GrantFiled: September 1, 2000Date of Patent: October 9, 2001Assignee: Milliken & CompanyInventors: John David O. Anderson, Walter A. Scrivens
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Patent number: 6297405Abstract: 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: GrantFiled: September 1, 2000Date of Patent: October 2, 2001Assignee: Milliken & CompanyInventors: John David O. Anderson, Walter Scrivens
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Patent number: 6180830Abstract: 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: GrantFiled: May 5, 1998Date of Patent: January 30, 2001Assignee: Rhodia ChimieInventor: Roland Jacquot
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Patent number: 5977414Abstract: 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: GrantFiled: March 30, 1998Date of Patent: November 2, 1999Assignee: Nippon Soda Co., Ltd.Inventors: Takashi Okabe, Isamu Kasahara, Tatsumi Suzuki
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Patent number: 5763676Abstract: 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: GrantFiled: February 14, 1997Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Matthias Irgang, Werner Schnurr, Joachim Wulff-Doring
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Patent number: 5679869Abstract: 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: GrantFiled: December 5, 1995Date of Patent: October 21, 1997Assignee: BASF AktiengesellschaftInventors: Werner Schnurr, Rolf Fischer, Joachim Wulff-Doring, Michael Hesse
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Patent number: 5585523Abstract: 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: GrantFiled: September 6, 1995Date of Patent: December 17, 1996Assignee: Hoechst AktiengesellschaftInventors: Jens Weiguny, Holger Borchert, Thomas Gerdau
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Patent number: 5527769Abstract: 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: GrantFiled: January 13, 1995Date of Patent: June 18, 1996Assignee: Firmenich SAInventors: Beat Winter, George Skouroumounis
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Patent number: 5336810Abstract: 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: GrantFiled: May 7, 1993Date of Patent: August 9, 1994Assignee: DSM N.V.Inventors: Paul C. Van Geem, Xiaoding Xu, Joseph J. F. Scholten
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Patent number: 5334769Abstract: 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: GrantFiled: October 26, 1992Date of Patent: August 2, 1994Assignee: Rhone-Poulenc ChimieInventors: Rose-Marie Ferrero, Roland Jacquot
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Patent number: 5306845Abstract: 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: GrantFiled: June 28, 1993Date of Patent: April 26, 1994Assignee: Mitsubishi Kasei CorporationInventors: Toshiharu Yokohama, Naoko Fujita, Takao Maki
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Patent number: 5260487Abstract: 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: GrantFiled: August 19, 1992Date of Patent: November 9, 1993Assignee: Imperial Chemical Industries PLCInventor: Daniel Levin
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Patent number: 5258544Abstract: 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: GrantFiled: March 5, 1991Date of Patent: November 2, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Laurence W. Reilly, Jr., Ching T. Tsuei, Walter Rodriquez, Thomas Goetzen
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Patent number: 5248816Abstract: 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: GrantFiled: October 8, 1992Date of Patent: September 28, 1993Assignee: Imperial Chemical Industries PLCInventors: Ralph Shuttleworth, Jan M. Fielden, Daniel Levin
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Patent number: 5183931Abstract: 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: GrantFiled: February 10, 1992Date of Patent: February 2, 1993Assignee: Phillips Petroleum CompanyInventors: Chung C. Tso, Robert L. Wynn
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Patent number: 5155278Abstract: 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: GrantFiled: September 30, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5138099Abstract: 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: GrantFiled: July 31, 1991Date of Patent: August 11, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: John F. Lang
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Patent number: 5107032Abstract: 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: GrantFiled: November 20, 1990Date of Patent: April 21, 1992Assignee: Noramco, Inc.Inventors: Dudley K. Erb, Janet E. Goldstein
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Patent number: 5084259Abstract: 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: GrantFiled: March 15, 1991Date of Patent: January 28, 1992Assignee: Amoco CorporationInventors: Larry C. Satek, Stephen T. McKenna, Vincent F. Smith, Jr.
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Patent number: 5072008Abstract: 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: GrantFiled: June 14, 1989Date of Patent: December 10, 1991Assignee: Imperial Chemical Industries PLCInventor: Gregory D. Harris
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Patent number: 5068450Abstract: A process for the preparation of aromatic aldehydes by formylation of aromatic compounds in liquid hydrofluoric acid in the presence of boron trifluoride.Type: GrantFiled: February 28, 1990Date of Patent: November 26, 1991Assignee: Rhone-Poulenc ChimieInventors: Michel Crochemore, Christophe Rochin
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Patent number: 5059716Abstract: 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: GrantFiled: August 8, 1990Date of Patent: October 22, 1991Assignee: Bayer AktiengesellschaftInventors: Winfried Joentgen, Helmut Fiege
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Patent number: 5057624Abstract: 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: GrantFiled: March 30, 1990Date of Patent: October 15, 1991Assignee: ALFA Wassermann S.p.A.Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
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Patent number: 5053552Abstract: 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: GrantFiled: June 14, 1990Date of Patent: October 1, 1991Assignee: Kuraray Company, Ltd.Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
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Patent number: 4990684Abstract: 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: GrantFiled: July 12, 1989Date of Patent: February 5, 1991Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer