Processes Patents (Class 568/426)
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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: 6323373Abstract: A process for preparing polymerizable biaryl derivatives comprises reacting an aromatic comprising a 6-membered ring which bears ester or benzylic OH groups in the 1,4 position with a second aromatic in a palladium-catalyzed cross-coupling reaction to give a biaryl and converting the ester or benzylic OH groups into polymerizable groups in one or more steps. The biaryls obtained are suitable for preparing polymers which are used as electroluminescence materials.Type: GrantFiled: June 9, 1999Date of Patent: November 27, 2001Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
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Patent number: 6313354Abstract: A process for the preparation of aromatic aldehydes comprising the steps of condensing a phenone ketal with a vinyl ether in the presence of a Lewis acid, subjecting the resulting acetal to acidic hydrolysis to form the corresponding &agr;,&bgr;-unsaturated aldehyde, and optionally hydrogenating the C═C double bond of said unsaturated aldehyde.Type: GrantFiled: September 30, 1999Date of Patent: November 6, 2001Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Thomas Markert, Ralph Nemitz
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Patent number: 6291721Abstract: An improved process for the preparation of 2-arylvinyl alkyl ether compounds of the structural formula I In addition, the present invention provides an improved process for the preparation of 1,4-diaryl-2-fluoro-2-butene compounds of the structural formula VType: GrantFiled: August 12, 1999Date of Patent: September 18, 2001Assignee: American Cyanamid Co.Inventors: Yulin Hu, David Allen Hunt, Weiguo Liu
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Patent number: 6274068Abstract: A method for the preparation of 2-hydroxyarylaldehydes from an aryloxy magnesium compound and formaldehyde, which comprises reacting at a temperature from 40-120° C., an aryloxy magnesium compound having an aryloxy anion and a non-aryloxy anion and in which (a) the non-aryloxy anion is more basic than the aryloxy anion such that when the aryloxy magnesium compound is brought into contact with an acidic species, the acid reacts more preferentially with the non-aryloxy anion to form an aryloxy magnesium salt and (b) the aryloxy anion has at least one free position ortho to the hydroxyl group in the aryloxy anion, with formaldehyde or a compound capable of giving rise to formaldehyde under the reaction conditions in the presence of a polar co-solvent capable of providing the non-aryloxy anion in the aryloxy magnesium compound characterized in that the non-aryloxy anion is selected from the group consisting of an oxide, a hydroxide, a carboxylate, a sulphate and a nitrate.Type: GrantFiled: December 10, 1998Date of Patent: August 14, 2001Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Jeffrey Howard Dimmit, Mark Alan Kearns, William H. Chambless
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Patent number: 6252121Abstract: This invention relates to a process for separating one or more cyclic products from a reaction product fluid comprising one or more cyclic reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a non-polar solvent and said one or more cyclic products, wherein said process comprises: (1) reacting said one or more cyclic reactants in the presence of said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent to form a multiphase reaction product fluid; and (2) separating said multiphase reaction product fluid to obtain a non-polar phase comprising said one or more cyclic reactants, metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and non-polar solvent and a polar phase comprising said one or more cyclic products.Type: GrantFiled: July 27, 1999Date of Patent: June 26, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Nicholas Argyropoulos, David Robert Bryant, Michael Leo Tulchinsky, Jeffrey Scott Kanel, Paul Foley, Barry Brent Fish
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Patent number: 6245945Abstract: A process for the selective hydrolysis of acetals in the presence of phthalides comprises reacting a mixture (M) comprising a) a phthalide of the formula (I) where: R1,R2,R3 and R4: are independently hydrogen, C1-C4-alkyl or halogen, and b) an acetal or ketal of the formula (II) where: R5 and R6: are independently C1-C6-alkyl, C6-C10-aryl or together ethylene, and R7 and R8: are independently C1-C6-alkyl, or one radical is a hydrogen and the other is a phenyl radical where from 1 to 3 hydrogen atoms of the phenyl radical may be replaced by C1-C6-alkyl radicals or C1-C4-alkoxy radicals, or R7 and R8 are together C3-C6-alkanediyl, and a hydrogen atom may be replaced by a hydroxyl group, at from 10 to 200° C. in the presence of from 1 to 10 mol of water, based on the amount of acetal or ketal of the formula (II), to hydrolyze the acetal or ketal of the formula (II) to the corresponding aldehyde or ketone.Type: GrantFiled: August 25, 2000Date of Patent: June 12, 2001Assignee: BASF AktiengesellschaftInventors: Andreas Weiper-Idelmann, Heinz Hannebaum, Hermann PĆ¼tter
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Publication number: 20010002425Abstract: A process is provided which allows a 1,4-bis(difluoroalkyl)benzene derivative to be produced inexpensively by a simple procedure without requiring any special facility.Type: ApplicationFiled: January 11, 2001Publication date: May 31, 2001Applicant: Nippon Shokubai Co., Ltd., a Japan CorporationInventors: Seiichi Teshima, Yoshinobu Asako
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Patent number: 6201156Abstract: An ether of the following formula (2): (wherein Ra is a hydrogen atom, a hydrocarbon group or a heterocyclic group, Rb is a hydrogen atom, a hydroxyl group or a substituted oxy group, and Rc is a hydrocarbon group or a heterocyclic group; Ra and Rc may be combined to form a ring with the adjacent carbon atom and oxygen atom) is reacted with nitrogen monoxide in the presence of a catalyst composed of an imide compound of the following formula (1): (wherein each of R1 and R2 is, identical to or different from each other, a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, or an acyl group; R1 and R2 may be combined to form a double bond, or an aromatic or nonaromatic ring; X is an oxygen atom or a hydroxyl group; and one or two N-substituted cyclic imido groups indicated in the formula (1) may further be formed on R1, R2, or on the double bond or aromatic or nonaromatType: GrantFiled: September 13, 1999Date of Patent: March 13, 2001Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano
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Patent number: 6169213Abstract: Process for the preparation of heteroaryl aldehydes or heteroaryl ketones by reaction with heteroarylmethanols with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, cycloaliphatic, heterocyclic or aromatic NO, and NOH containing compounds.Type: GrantFiled: January 5, 2000Date of Patent: January 2, 2001Assignee: Consortium f{umlaut over (u)}r elektrochemische Industrie GmbHInventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
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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: 5910613Abstract: A process for producing aromatic aldehydes by carbonylation of an arene in the presence of triflic acid catalyst is described by reacting an arene, such as toluene, with carbon monoxide in the presence of triflic acid (as a catalyst), for a reaction time less than 90 minutes, at a carbon monoxide partial pressure of about 700-2000 psig, at a temperature of from about 0-50.degree. C. to produce an aromatic aldehyde such as tolualdehyde and by-products, the by-products being less than 5% by weight based on the total reaction products.The mole ratio of triflic acid to arene is between about 0.8 to 20, with the reaction having an isomer selectivity greater than 95% by weight for the para isomer aldehyde, and showing substantially no meta isomer.Type: GrantFiled: May 6, 1998Date of Patent: June 8, 1999Assignee: HNA Holdings, Inc.Inventors: David Anthony Schiraldi, Jeffrey Charles Kenvin
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Patent number: 5888787Abstract: A method for oxidation of a pendant methyl moiety on an aromatic ring to the pendant aldehyde moiety is presented. The reaction employs laccase and the diammonium salt of 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid), and is carried out in the presence of oxygen.Type: GrantFiled: July 2, 1996Date of Patent: March 30, 1999Assignee: North Carolina State UniversityInventors: Chen-Loung Chen, Josef S. Gratzl, Adrianna G. Kirkman, Antje Potthast, Thomas Rosenau
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Patent number: 5872153Abstract: A process for preparing an aqueous o-phthalaldehyde-glutaraldehyde solution which comprises converting an acetal of the o-phthalaldehyde in a 10 to 60% strength aqueous glutaraldehyde solution into o-phthalaldehyde at room temperature up to 100.degree. C. by eliminating the corresponding alcohol, and removing the eliminated alcohol to give the aqueous o-phthalaldehyde-glutaraldehyde solution.Type: GrantFiled: November 26, 1997Date of Patent: February 16, 1999Assignee: DSM Chemie Linz GmbHInventors: Karl Heinz Giselbrecht, Eduard Perndorfer
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Patent number: 5861286Abstract: The present invention relates to a process for the preparation of aromatic substances having formula (I), characterized in that a substrate having formula (II) is subjected to an oxydation in the presence of at least one protein and at least one metal ion, formula wherein R.sub.1 may be a radical --H, --CH.sub.3, --CH.sub.2 OH, --CHO, --COOH, --OCH.sub.3, or --COO--CH(COOH)--CH.sub.2 --C.sub.6 H.sub.3 (OH).sub.2 ; R.sub.2 may be a radical --H, --OH, or --OCH.sub.3 ; R.sub.3 may be a radical --H, --OH, --OCH.sub.3, or O-glucosid; R.sub.4 may be a radical --H, --OH, or --OCH.sub.3.Type: GrantFiled: September 25, 1997Date of Patent: January 19, 1999Assignee: V. Mane FilsInventors: Jean Mane, Joseph Zucca
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Patent number: 5856583Abstract: A method for the preparation of 2-hydroxyarylaldehydes from an aryloxy magnesium compound and formaldehyde, which comprises reacting at a temperature from 40.degree.-120.degree. C., an aryloxy magnesium compound having an aryloxy anion and a non-aryloxy anion and in which (a) the non-aryloxy anion is more basic than the aryloxy anion such that when the aryloxy magnesium compound is brought into contact with an acidic species, the acid reacts more preferentially with the non-aryloxy anion to form an aryloxy magnesium salt and (b) the aryloxy anion has at least one free position ortho to the hydroxyl group in the aryloxy anion, with formaldehyde or a compound capable of giving rise to formaldehyde under the reaction conditions in the presence of a polar co-solvent capable of providing the non-aryloxy anion in the aryloxy magnesium compound characterized in that the non-aryloxy anion is selected from the group consisting of an oxide, a hydroxide, a carboxylate, a sulphate and a nitrate.Type: GrantFiled: May 21, 1997Date of Patent: January 5, 1999Assignee: Allco Chemical Corp.Inventors: Jeffrey Howard Dimmit, Mark Alan Kearns, William H. Chambless
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Patent number: 5786496Abstract: The present invention provides a new tetradentate bis-amido bis-alkoxo, 1,2-(bis-2,20diphenyl-2-hydroxyethanamido)benzene (H.sub.4 PHAB) and various derivatives thereof. This ligand is able to stabilize high valen metal oxo complexes by providing strong sigma donor ligands and through the use of steric bulk to prevent decomposition via formation of the .mu.-oxo dimers. Disclosed are novel metal oxo structural chemistry and oxidation reactions carried out with the novel metal oxo complexes.Type: GrantFiled: November 15, 1996Date of Patent: July 28, 1998Assignee: Northwestern UniversityInventors: Thomas V. O'Halloran, Frederick M. MacDonnell, Nathanael L. P. Fackler
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Patent number: 5744026Abstract: Dibenzyl ether can be readily cleaved to form primarily benzaldehyde and toluene as products, along with minor amounts of bibenzyl and benzyl benzoate, in the presence of a catalyst system comprising a Group 6 metal, preferably molybdenum, a salt, and an organic halide. Although useful synthetically for the cleavage of benzyl ethers, this cleavage also represents a key model reaction for the liquefaction of coal; thus this catalyst system and process should be useful in coal liquefaction with the advantage of operating at significantly lower temperatures and pressures.Type: GrantFiled: April 10, 1997Date of Patent: April 28, 1998Assignee: Eastman Chemical CompanyInventor: Joseph Robert Zoeller
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Patent number: 5710343Abstract: The invention provides a method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde by reacting 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde with a reagent comprising zinc chloride, water and hydrogen chloride.Type: GrantFiled: May 8, 1997Date of Patent: January 20, 1998Assignee: Orion-Yhtyma OyInventor: Reijo Johannes Backstrom
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Patent number: 5693869Abstract: This invention relates to an improved process for the single step oxidation of 3-phenoxytoluene to 3-phenoxybenzaldehyde using molecular oxygen as the oxidant by employing a Ti.sub.2 VMoP.sub.6 O.sub.24 catalyst having particular infrared spectral bands.Type: GrantFiled: December 9, 1994Date of Patent: December 2, 1997Assignee: Council of Scientific & Industrial ResearchInventors: Joseph Kuruvilla, Changaramponnath Gopinathan, Sarada Gopinathan, Paul Ratnasamy
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Patent number: 5672765Abstract: Aromatic, ring-fluorinated compounds are prepared by reaction of corresponding chlorine compounds or bromine compounds with alkali metal fluorides using a diamide as solvent. Most of the diamides which can be used are novel compounds.Type: GrantFiled: July 14, 1995Date of Patent: September 30, 1997Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Marianne Lohr, Heinrich Wamhoff
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Patent number: 5659084Abstract: Processes for preparing 2-substituted benzaldehydes of general formula (I), wherein: R.sub.1 is CH.sub.2 CH.sub.2 --(L.sub.1).sub.p --(CH.sub.2).sub.q --(L.sub.2).sub.r --CH.sub.2 --(T).sub.2 --Z; L.sub.1 and L.sub.2 are independently CH.sub.2 CH.sub.2, CH.dbd.CH or C.tbd.C; q is 0 to 8; p, r and s are independently 0 or 1; T is O, S, CH.sub.2, CH.dbd.CH, C.tbd.C; and Z is C.sub.1-4 alkyl, ethynyl, trifluoromethyl, isopropenyl, furanyl, thienyl, cyclohexyl or phenyl optionally mono substituted with CF.sub.3, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, methylthio, or trifluoromethylthio; and R.sub.2 and A are independently H, CF.sub.3, C.sub.1-4 alkyl, F, Cl, Br or I; are useful for preparing pharmaceutically active compounds.Type: GrantFiled: December 7, 1994Date of Patent: August 19, 1997Assignees: SmithKline Beecham Corporation, SmithKline Beecham plcInventors: Kerry Joseph Gombatz, Michael Anthony Forth, Jerome Francis Hayes, Michael Barry Mitchell, Stephen Alexander Smith
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Patent number: 5576463Abstract: The new process for the preparation of 2-nitrobenzaldehydes of the general formula ##STR1## in which X.sub.1 and X.sub.2 either independently of one another represent hydrogen or halogen or one of the substituents represents nitro and the other substituent then represents hydrogen,by oxidation of 2-nitrotoluenes of the general formula ##STR2## in which X.sub.1 and X.sub.2 have the meaning indicated above is characterized in that the oxidation with oxygen or an oxygen-containing gas is carried out in the presence of at least one alkoxyalkylamine as a solvent and in the presence of strong bases.Type: GrantFiled: March 3, 1995Date of Patent: November 19, 1996Assignee: Bayer AktiengesellschaftInventors: Albert Schnatterer, Helmut Fiege
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Patent number: 5574164Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.Type: GrantFiled: April 21, 1995Date of Patent: November 12, 1996Assignee: Hoescht Roussel Pharmaceuticals Inc.Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Hamer, Brian S. Freed, Gregory H. Merriman
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Patent number: 5510538Abstract: A process for the selective oxidation of a primary or secondary alcohol to an aldehyde or ketone and for the oxidation of a 1,2-diol to an .alpha.-ketol or .alpha.-diketone, which comprises contacting the alcohol or 1,2-diol with o-iodoxybenzoic acid. This process is suited for selective oxidation of alcohols containing easily oxidizable groups, such as amino or thioether groups and easily oxidizable heterocycles.Type: GrantFiled: December 16, 1994Date of Patent: April 23, 1996Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Marco Frigerio, Simona Sputore, Marco Santagostino
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Patent number: 5498800Abstract: A process is disclosed for obtaining a compound of the formulaAr-Z IIwhere Ar, R.sub.1 and R.sub.2 are defined in the specification and Z is --C(R.sub.3).dbd.CH.sub.2 or --CH(R.sub.3)CHO where R.sub.3 is defined in the specification. The process utilizes a heterogeneous mixture of the compound of formula I and an alkali or alkaline earth metal in dimethylformamide. The mixture is subjected to ultrasonic vibrations for a time and at a temperature sufficient to produce a compound of formula II: ##STR1## where Ar, R.sub.1, and R.sub.2 are defined above and X is the halo group.Type: GrantFiled: January 9, 1995Date of Patent: March 12, 1996Assignee: Albemarle CorporationInventor: Thanikavelu Manimaran
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Patent number: 5489715Abstract: 4,5-Difluorobenzaldehydes of a given formula are prepared by the reaction of corresponding benzaldehydes with a fluorinating agent.Type: GrantFiled: November 4, 1994Date of Patent: February 6, 1996Assignee: Bayer AktiengesellschaftInventor: Albrecht Marhold
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Patent number: 5488174Abstract: Process for the hydroformylation of ethylenically unsaturated compounds, by reaction with carbon monoxide and hydrogen in the presence of a catalyst based on a metal of the platinum group, a source of anions and a bidentate ligand of the formula R.sup.1 R.sup.2 M.sup.1 RM.sup.2 R.sup.3 R.sup.4 wherein M.sup.1 and M.sup.2 are phosphorus, arsenic or antimony, R is a bivalent organic bridging group with 1 to 4 atoms in the bridge, R.sup.1 and R.sup.2 together represent a bivalent cyclic group and R.sup.3 and R.sup.4 independently represent an optionally substituted hydrocarbyl group or together have the same meaning as R.sup.1 and R.sup.2.Type: GrantFiled: August 12, 1994Date of Patent: January 30, 1996Assignee: Shell Oil CompanyInventors: Eit Drent, Dennis H. L. Pello, Jacoba C. L. J. Suykerbuyk
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Patent number: 5475156Abstract: A method is provided for converting a 2,4,6-trialkylphenol, such as mesitol, to a dialkylphenol, for example 2,6-dimethylphenol, by effecting the selective oxidation of the 2,4,6-trialkylphenol, followed by the deformylation of the resulting 3, 5-dialkyl-4-hydroxybenzaldehyde.Type: GrantFiled: June 6, 1994Date of Patent: December 12, 1995Assignee: General Electric CompanyInventors: Andrew J. Caruso, Julia L. Lee
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Patent number: 5471003Abstract: Disclosed is a process for the removal of crotonaldehyde impurity from cyclopropanecarboxaldehyde by the selective, catalytic hydrogenation of crotonaldehyde to butyraldehyde followed by distillation of the butyraldehyde from the cyclopropanecarboxaldehyde.Type: GrantFiled: November 28, 1994Date of Patent: November 28, 1995Assignee: Eastman Chemical CompanyInventor: Shaowo Liang
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Patent number: 5457239Abstract: A process for the preparation of a formylated aromatic compound comprising contacting an aromatic compound with (i) a halogenated compound in the presence of a Lewis acid, and (ii) a base, is described. The subject process provides an efficient and effective means of preparing formylated compounds which may be useful in a wide variety of applications.Type: GrantFiled: May 25, 1994Date of Patent: October 10, 1995Assignee: Union Camp CorporationInventors: Walter C. Frank, Richard L. Veazey, John J. Mahurter, Mark J. Jenkins, Neil R. Fairfax
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Patent number: 5436374Abstract: A process for producing a 4-formyl-4'-methylbiphenyl from a biphenyl which comprises conducting the carbonylation of the biphenyl with carbon monoxide in the presence of a HF-BF.sub.3 catalyst in a carbonylation reactor to obtain the resulting reaction product solution containing a 4-formylbiphenyl, separating the 4-formylbiphenyl from the reaction product solution, hydrogenating the separated 4-formylbiphenyl to obtain a 4-methylbiphenyl, recycling the 4-methylbiphenyl to the carbonylation reactor, and then conducting both the carbonylation of the biphenyl with carbon monoxide to obtain a formylbiphenyl and the carbonylation of the 4-methylbiphenyl with carbon monoxide to obtain a 4-formyl-4'-methylbiphenyl simultaneously in the presence of the HF-BF.sub.3 catalyst in the carbonylation reactor.Type: GrantFiled: July 28, 1994Date of Patent: July 25, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Makoto Komatsu, Susumu Fujiyama, Koichi Kida, Mitsuharu Kitamura
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Patent number: 5430194Abstract: The present invention relates to a process for producing an optically active aldehyde (first aldehyde) containing a reduced amount of the corresponding enantiomeric aldehyde (second aldehyde) which process comprises: (1) providing an initial solution containing a non-eutectic mixture of the first aldehyde and the second aldehyde, which mixture has a composition in the compositional region where only the first aldehyde crystallizes when its solubility limit in the solution is exceeded, and (2) maintaining the solution at a temperature above the eutectic temperature of the mixture and under conditions such that the solubility limit of the first aldehyde is exceeded so as to form a crystalline first aldehyde containing relatively less of the second aldehyde than was present in the initial solution.Type: GrantFiled: June 24, 1994Date of Patent: July 4, 1995Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Bruce A. Barner, John R. Briggs, Jonathan J. Kurland, Charles G. Moyers, Jr.
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Patent number: 5387718Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.Type: GrantFiled: July 14, 1992Date of Patent: February 7, 1995Assignee: Huels AktiengesellschaftInventors: Gunther Kohler, Peter Bickert
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Patent number: 5382699Abstract: A method for the preparation of 3,4-dihydroxy-5-nitrobenzaldehyde by reacting 4-hydroxy-3-methoxy-5-nitrobenzaldehyde with a strong nucleophilic agent which may be created by reacting an aromatic mercapto compound with a strong organic or inorganic alkali metal base such as lithium hydroxide. The reaction is performed at elevated temperatures using an aprotic polar solvent. It is preferably carried out in an inert atmosphere.Type: GrantFiled: January 6, 1994Date of Patent: January 17, 1995Assignee: Orion-yhtyma OyInventors: Erkki Honkanen, Stig Lindholm
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Patent number: 5382694Abstract: A process for the continuous production of aromatic aldehydes of the formula (1) ##STR1## in which Ar is an aryl radical, R.sup.1, R.sup.2 and R.sup.3 independently of one another are hydrogen, fluorine, chlorine or bromine atoms, in which dichloromethyl-substituted aromatics of the formula (2) ##STR2## in which Ar, R.sup.1, R.sup.2, R.sup.3 have the above meanings, are continuously hydrolyzed with an aqueous solution of one or more catalysts of the formula (3)MX.sub.n (3)in which M is a transition metal selected from the group comprising iron, nickel, copper, chromium, thallium, zinc and mercury, X is F, Cl, Br, I, OH, SO.sub.4, PO.sub.4 or NO.sub.3, and n depending on the oxidation state of the transition metal M is the number 1, 2, 3 or 4, in a concentration of from about 1 to about 50%, based on the weight of water in the catalyst solution, at temperatures of from about 70.degree. to about 160.degree. C.Type: GrantFiled: November 23, 1993Date of Patent: January 17, 1995Assignee: Hoechst AktiengesellschaftInventors: Gilbert Billeb, Georg Folz
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Patent number: 5360938Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.Type: GrantFiled: July 16, 1992Date of Patent: November 1, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James E. Babin, Gregory T. Whiteker
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Patent number: 5354919Abstract: Aromatic compounds bearing oxidizable alkyl substituents, e.g., alkoxylated and/or hydroxylated such substrates, notably the phenolics/cresols, are selectively oxidized, e.g., into hydroxybenzaldehydes, by reacting same with appropriate oxidizing agents, in an aqueous reaction medium, in the presence of a catalytically effective amount of a solid, palladium-containing oxidation catalyst (optionally containing a cocatalytically effective amount of tin, germanium, tellurium and/or copper).Type: GrantFiled: June 29, 1993Date of Patent: October 11, 1994Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher, Eric Fache
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Patent number: 5354908Abstract: A method for absorbing cobalt within an olefinic feedstock which comprises the steps of introducing a volatile cobalt compound and an olefinic feedstock into an absorber to form a cobalt-containing olefin mixture, withdrawing the cobalt-containing olefin mixture from the absorber, introducing at least a portion of the cobalt-containing olefin mixture into a reactor, wherein a substantial portion of the volatile cobalt compound entrained within the cobalt-containing olefin mixture decomposes to its non-volatile cobalt compound species, and recycling this mixture back to the absorber so that it can be used to further absorb volatile cobalt such that a more concentrated cobalt-containing olefin solution is formed.Type: GrantFiled: July 16, 1993Date of Patent: October 11, 1994Assignee: Exxon Chemical Patents Inc.Inventor: Kirk C. Nadler
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Patent number: 5354920Abstract: A method for the preparation of a 2-hydroxyarylaldehyde which comprises reacting an aryloxymagnesium halide derived from a phenol having at least one free ortho position relative to the phenolic hydroxy group with formaldehyde or a formaldehyde-liberating compound under substantially anhydrous conditions in the presence of a polar organic solvent other than hexamethylphosphoramide or 1,3-dimethyl-3,4,5,6-2(1H)-pyrimidone.Type: GrantFiled: August 10, 1993Date of Patent: October 11, 1994Assignee: Zeneca LimitedInventors: Brian G. Cox, Daniel Levin
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Patent number: 5352840Abstract: Substituting aqueous hydrogen peroxide/hydrogen bromide for bromine in a known process for producing a ditertiaryalkyl substituted hydroxybenzaldehyde such as ditertiarybutyl hydroxybenzaldehyde from the corresponding ditertiaryalkyl substituted methylphenol results in a substantially impaired yield of product.Improved yields are obtained by employing a reaction temperature of at least 40.degree. C., preferably 50.degree. to 80.degree. C. in conjunction with a hydrophobic solvent such as chloroform. Preferably, the process employs very concentrated hydrogen peroxide solution, 65% to 75% w/w, introduced into the bromide-containing reaction mixture during a period of from 25 to 75 minutes.Type: GrantFiled: May 10, 1993Date of Patent: October 4, 1994Assignee: Solvay Interox LimitedInventors: Stephen G. Grundy, Kevan M. Reeve, Michael C. Rocca
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Patent number: 5347054Abstract: A process for preparing aromatic aldehydes of the formula (1) ##STR1## in which R.sup.1, R.sup.2, R.sup.3 independently of one another are H, F, Cl or Br, by hydrolyzing a dichloromethyl-substituted benzene of the formula (2) ##STR2## in which R.sup.1, R.sup.2, R.sup.3 have the abovementioned meanings with a from about 1 to about 50% strength aqueous solution of one or more zinc salts of the formula (3)ZnX.sub.n (3)in which X is F, Cl, Br, I, OH or SO.sub.4, and n is, depending on the anion X, the number 1 or 2, at temperatures of from about 70.degree. to about 160.degree. C.Type: GrantFiled: November 23, 1993Date of Patent: September 13, 1994Assignee: Hoechst AktiengesellschaftInventors: Gilbert Billeb, Peter Burg
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Patent number: 5336811Abstract: A process for the preparation of an aldehyde by reacting the corresponding aryl methanol with a stable free radical nitroxide in the presence of a NO.sub.x -generating compound at a temperature in the range of from about 0.degree. C. to about 100.degree. C. and thereafter separating out the aldehyde.Type: GrantFiled: August 18, 1993Date of Patent: August 9, 1994Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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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: 5321165Abstract: A method of producing an ethynyl aromatic aldehyde comprises reacting a protected copper(I) acetylide salt with a halogen substituted aromatic compound to produce a protected ethynyl aromatic aldehyde.The protected ethynyl aromatic aldehyde may be deprotected to yield an acetylene terminated aromatic aldehyde which is useful for making acetylenic Schiff's base monomers and conductive polymers thereof.Type: GrantFiled: June 14, 1993Date of Patent: June 14, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventors: Thomas DiBerardino, Patricia M. Lutz, Barbara F. Howell
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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: 5304685Abstract: A process for preparing 3-(hydroxyphenyl)propionaldehydes of the formula I ##STR1## and, where appropriate, for preparing 3-(hydroxyphenyl)propanols of the formula II ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl or C.sub.5 -C.sub.20 -alkylcycloalkylalkyl,R.sup.3 and R.sup.4 are each aryl, C.sub.7 -C.sub.20 -aralkyl, heterocycloalkyl or C.sub.3 -C.sub.20 -heterocycloalkylalkyl, entailsa) reacting phenols of the formula III ##STR3## where R.sup.1 and R.sup.2 have the abovementioned meanings, with 3-hydroxypropionaldehydes of the formula IV ##STR4## where R.sup.3 and R.sup.4 have the abovementioned meanings, in the presence of a basic catalyst at from 90.degree. to 230.degree. C. and under from 0.01 to 50 bar and, where appropriate,b) treating the resulting 3-(hydroxyphenyl)propionaldehydes of the formula I ##STR5## where R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: March 26, 1993Date of Patent: April 19, 1994Assignee: BASF AktiengesellschaftInventors: Franz Merger, Martin Schmidt-Radde
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Patent number: 5294744Abstract: A novel two-step reaction process for preparing 5-substituted-2-methoxybenzaldehyde compounds is disclosed wherein the substituent group is either isopropyl or trifluoromethoxy. The process involves (1) reacting a corresponding 4-substituted phenol compound with dimethyl carbonate in the presence of a tertiary-amine base to form the corresponding 4-substituted anisole compound, and (2) thereafter subjecting the latter intermediate product obtained in the first step to aromatic C-formylation on the ring with hexamethylenetetramine in the presence of trifluoroacetic acid, followed by hydrolysis, to ultimately yield the desired aldehyde compound. The two aromatic aldehyde compounds so obtained, viz., 2-methoxy-5-trifluoromethoxybenzaldehyde and 2-methoxy-5-isopropylbenzaldehyde, are known to be useful as intermediates that specifically lead to (2S,3S)-cis-3-(2-methoxy-5-trifluoromethoxybenzyl)amino-2-phenylpiperidine and (2S,3S)-cis-2-(diphenylmethyl)-N-[(2-methoxy-5-isopropylphenyl)methyl]-1-a zabicyclo[2.2.Type: GrantFiled: April 20, 1993Date of Patent: March 15, 1994Assignee: Pfizer Inc.Inventors: Dennis M. Godek, William M. Synder, Andrew M. Stewart
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace