Additional Chalcogen Bonded Directly To The Benzene Ring Patents (Class 558/271)
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Patent number: 6114563Abstract: A method and catalyst system for economically producing aromatic carbonates from aromatic hydroxy compounds. In one embodiment, the present invention provides a method of carbonylating aromatic hydroxy compounds by contacting at least one aromatic hydroxy compound with oxygen and carbon monoxide in the presence of a carbonylation catalyst system that includes a catalytic amount of an inorganic co-catalyst containing bismuth. In various alternative embodiments, the carbonylation catalyst system can include an effective amount of a palladium source and an effective amount of a halide composition. Further alternative embodiments can include catalytic amounts of various inorganic co-catalyst combinations.Type: GrantFiled: April 29, 1999Date of Patent: September 5, 2000Assignee: General Electric Co.Inventors: James Lawrence Spivack, Donald Wayne Whisenhunt, Jr., James Norman Cawse, Bruce Fletcher Johnson, Kirill Shalyaev
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Patent number: 6093842Abstract: Production of diaryl carbonate esters by reaction of a dialkyl carbonate and an aromatic alcohol to form a diaryl carbonate and an alkyl alcohol is accomplished by introducing three reactant streams into an extractive/reactive distillation column in the presence of a transesterification catalyst. The three reactant streams are a first reactant stream containing a dialkyl carbonate, a second reactant stream containing an aromatic alcohol, and a third reactant stream containing an entraining agent. The entraining agent is selected from among compounds that do not form azeotropes with the dialkyl carbonate or the alkyl alcohol and that boil at a higher temperature than either the dialkyl carbonate or the alkyl alcohol. The first reactant stream is introduced into the column below the second reactant stream, and the second reactant stream is introduced into the column below the third reactant stream. A product stream containing diaryl carbonate esters is recovered from the bottom of the column.Type: GrantFiled: September 25, 1998Date of Patent: July 25, 2000Assignee: General Electric CompanyInventors: Martin H. Oyevaar, Bill W. To, Michael F. Doherty, Michael F. Malone
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Patent number: 6034262Abstract: A continuous flow process for converting hydroxyaromatic compounds to diaryl carbonates by reaction with oxygen and carbon monoxide in the presence of a catalyst system typically comprising a group VIIIB metal or compound thereof, an inorganic co-catalyst, an organic co-catalyst and a hexaalkylguanidinium bromide or chloride, preferably bromide, wherein at least two components of the catalyst system, preferably lead oxide and hexaalkylguanidinium bromide, are introduced separately into the reactor.Type: GrantFiled: December 22, 1998Date of Patent: March 7, 2000Assignee: General Electric CompanyInventor: Phillip Moreno
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Patent number: 6001768Abstract: In the process for preparing an aromatic carbonate from an aromatic hydroxy compound, CO and O.sub.2 in the presence of a quaternary salt and a base, use is advantageously made of supported catalysts which, in the reaction-ready state, contain a platinum metal, a platinum metal compound or a complex containing a platinum metal compound on a support comprising a metal oxide whose metal can occur in a plurality of oxidation states.Type: GrantFiled: March 29, 1996Date of Patent: December 14, 1999Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Carsten Hesse, Jorg-Dietrich Jentsch, Johann Rechner, Eberhard Zirngiebl
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Patent number: 5981788Abstract: Catalytic materials including divalent palladium compounds, divalent cobalt compounds and bromide sources such as tetraalkylammonium and hexaalkylguanidinium bromides are removed from organic carbonylation reaction mixtures comprising said materials in combination with diaryl carbonate and hydroxyaromatic compound. The removal steps include extraction with an aqueous complexing solution for palladium, extraction with an aqueous non-basic and preferably ionic extractant for cobalt, and extraction with water to remove bromide source. These steps may be combined into an integrated process. Further steps of recycle of the palladium by reduction to elemental palladium and conversion to a catalytically active species, and conversion of cobalt to a catalytically active species, may be included in the integrated process.Type: GrantFiled: November 3, 1997Date of Patent: November 9, 1999Assignee: General Electric CompanyInventors: John Yaw Ofori, Sheldon Jay Shafer, Eric James Pressman, Ganesh Kailasam, Julia Lam Lee
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Patent number: 5917078Abstract: An improved continuous process for removal of water from a process for producing organic carbonates, particularly diphenyl carbonate, by treating the water containing products of the reaction with a condensable stripping agent in a gaseous state and recycling a major portion of the water poor reaction products back to the reaction for producing the organic carbonate. The stripping agent, preferably n-pentane, is condensed upon removal from the water stripping step and recycled back to the water stripping step.Type: GrantFiled: September 25, 1998Date of Patent: June 29, 1999Assignee: General Electric CompanyInventors: Richard A. Battista, Francis S. Lo, Robert L. Tatterson
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Patent number: 5917077Abstract: Diaryl carbonates such as diphenyl carbonate are prepared by reaction of hydroxyaromatic compounds such as phenol with oxygen and carbon monoxide in the presence of a catalyst composition comprising a Group VIIIB metal such as palladium or a compound thereof, a bromide source such as a quaternary ammonium or hexaalkylguanidinium bromide and a polyaniline in partially oxidized and partially reduced form. The polyaniline is preferably halide-doped and in the form of a blend with a binder polymer containing ether or ester groups and a complex-forming salt.Type: GrantFiled: June 1, 1998Date of Patent: June 29, 1999Assignee: General Electric CompanyInventors: Raghunath Vitthal Chaudhari, Sunil Purushottam Gupte, Ashutosh Anant Kelkar, Subbareddiar Kanagasabapathy, Subramaniam Radhakrishnan
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Patent number: 5908952Abstract: Hydroxyaromatic compounds such as phenol are converted to diaryl carbonates by reaction with oxygen and carbon monoxide in the presence of a catalyst package which comprises a Group VIIIB metal, preferably palladium, salt of at least one aliphatic .beta.-diketone such as 2,4-pentanedione. The catalyst package also preferably comprises an inorganic cocatalyst, an organic cocatalyst and a bromide or chloride, preferably bromide, source such as a hexaalkylguanidinium bromide. The use of the .beta.-diketone salt confers such advantages as long shelf life under normal storage conditions, high activity upon recycle and capability of carbonylation at relatively low temperatures.Type: GrantFiled: March 24, 1997Date of Patent: June 1, 1999Assignee: General Electric CompanyInventors: Eric James Pressman, Sheldon Jay Shafer
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Patent number: 5900501Abstract: The present invention relates to a process for the continuous production of carbonates having aromatic ester groups by the reaction of aromatic hydroxy compounds with phosgene in the presence of heterogeneous catalysts, phosgene still present being removed from the stream of waste gas by returning the waste gas to an additional reactor.Type: GrantFiled: February 13, 1997Date of Patent: May 4, 1999Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Hans-Josef Buysch, Steffen Kuhling, Gottfried Zaby
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Patent number: 5898079Abstract: Hydroxyaromatic compounds such as phenol are converted to diaryl carbonates by reaction with oxygen and carbon monoxide in the presence of a catalyst package which typically comprises a group VIIIB metal or compound thereof, an inorganic cocatalyst, an organic cocatalyst and a hexaalkylguanidinium bromide or chloride, preferably bromide. The use of the hexaalkylguanidinium salt causes an increase in the yield of diaryl carbonate without a decrease in selectivity.Type: GrantFiled: September 12, 1997Date of Patent: April 27, 1999Assignee: General Electric CompanyInventors: Eric James Pressman, Sheldon Jay Shafer
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Patent number: 5898080Abstract: Hydroxyaromatic compounds such as phenol are converted to diaryl carbonates by reaction with oxygen and carbon monoxide in the presence of a catalyst package which typically comprises a group VIIIB metal or compound thereof, an inorganic cocatalyst, an organic cocatalyst and a hexaalkylguanidinium bromide or chloride, preferably bromide. The use of the hexaalkylguanidinium salt causes an increase in the yield of diaryl carbonate without a decrease in selectivity.Type: GrantFiled: August 27, 1997Date of Patent: April 27, 1999Assignee: General Electric CompanyInventors: Eric James Pressman, Sheldon Jay Shafer
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Patent number: 5877140Abstract: The present invention relates to anionic compounds and their application in detergent compositions. The compounds have the dual benefits of surfactancy and suds suppression.Type: GrantFiled: March 20, 1997Date of Patent: March 2, 1999Inventors: Frederick Edward Hardy, Barry Thomas Ingram, Christian Leo Marie Vermote
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Patent number: 5834615Abstract: A high purity diaryl carbonate is produced with a high efficiency by reacting carbon monoxide with an alkyl nitrite and/or an alkyl alcohol; reacting the resultant dialkyl oxalate with a hydroxyaryl compound, for example, phenol; decarbonylating the resultant diaryl oxalate to produce a diaryl carbonate and carbon monoxide; and collecting the diaryl carbonate from the decarbonylation reaction product mixture, the carbon monoxide produced in the decabonylation step being optionally reused for the production of the dialkyl oxalate.Type: GrantFiled: September 24, 1997Date of Patent: November 10, 1998Assignee: Ube Industries, Ltd.Inventors: Keigo Nishihira, Shuji Tanaka, Katsumasa Harada, Ryoji Sugise
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Patent number: 5831111Abstract: The present invention relates to a process for the continuous production of carbonates having aromatic ester groups by reacting aromatic hydroxy compounds with phosgene in the gas phase in the presence of heterogeneous catalysts.Type: GrantFiled: May 5, 1997Date of Patent: November 3, 1998Assignee: Bayer AGInventors: Pieter Ooms, Eric Bischof, Hans-Josef Buysch, Steffen Kuhling, Gottfried Zaby, Wolfgang Jakob, Jurgen Dahmer, Norbert Schon
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Patent number: 5824816Abstract: Catalyst systems with a content of a platinum-group-metal catalyst, a co-catalyst, a quaternary salt and a base for the oxidative carbonylation of aromatic hydroxy compounds to the corresponding diaryl carbonates are obtained according to the invention as a residual melt by melt crystallization and can be returned into the carbonylation reaction or worked up to valuable materials. The melt crystallizate, which consists predominantly of diaryl carbonate and the parent aromatic hydroxy compound, is worked up to pure diaryl carbonate and pure hydroxy compound.Type: GrantFiled: April 1, 1997Date of Patent: October 20, 1998Assignee: Bayer AGInventors: Hans-Josef Buysch, Carsten Hesse, Johann Rechner, Hans-Peter Wirges
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Patent number: 5821377Abstract: In the process for the production of diaryl carbonates by oxidative carbonylation of the underlying aromatic hydroxy compounds in the presence of a catalyst containing a platinum group metal, a co-catalyst, a quaternary salt and a base, the catalyst is used as a supported catalyst in a stationary arrangement or in the fluid phase and the reaction is performed in the condensed phase. The co-catalyst is preferably also attached to the support.Type: GrantFiled: April 1, 1997Date of Patent: October 13, 1998Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Carsten Hesse, Johann Rechner
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Patent number: 5792883Abstract: An improved process for preparing a diaryl carbonate from a diaryl oxalate in a liquid phase by decarbonylation utilizes a reaction vessel composed of two or more reaction chambers which are connected in series. The process is composed of the steps of continuously introducing the diaryl oxalate and an organic phosphorus compound having a trivalent or pentavalent phosphorus atom and at least one carbon-phosphorus bonding into the first chamber and continuously recovering a reaction mixture mainly containing the diaryl carbonate from the last chamber under the condition that a mixture of the diaryl oxalate and the organic phosphorus compound is heated in the reaction chambers, while discharging carbon monoxide released from the mixture.Type: GrantFiled: October 6, 1997Date of Patent: August 11, 1998Assignee: Ube Industries, Ltd.Inventors: Katsumasa Harada, Ryoji Sugise, Koichi Kashiwagi, Takashi Doi, Sadao Niida, Toshio Kurafuji
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Patent number: 5792762Abstract: The invention provides dihydronaphthofluorene compounds, formulations, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, and cardiovascular-related pathological conditions.Type: GrantFiled: September 19, 1997Date of Patent: August 11, 1998Assignee: Eli Lilly and CompanyInventors: Henry Uhlman Bryant, Thomas Alan Crowell, Charles David Jones
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Patent number: 5777162Abstract: Described herein are compounds of Formula (XX) and Formula (XXIV), shown below, and processes of making same. ##STR1## wherein p is 0 ##STR2## wherein p is 1, and Y is chlorine or bromine.Type: GrantFiled: November 12, 1996Date of Patent: July 7, 1998Assignee: Zeneca LimitedInventors: Ian Richard Matthews, Christopher Richard Ayles Godfrey, John Martin Clough
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Patent number: 5760272Abstract: Hydroxyaromatic compounds such as phenol are converted to diaryl carbonates by reaction with oxygen and carbon monoxide in the presence of a catalyst package and an added diluent free from active hydrogen. The preferred catalyst packages comprise a Group VIIIB metal or salt thereof, an inorganic cocatalyst, and organic cocatalysts and a bromide or chloride source. The amount of added diluent is an effective amount to improve selectivity to diaryl carbonate. Preferred diluents are diphenyl carbonate and N-methylpyrrolidone.Type: GrantFiled: March 24, 1997Date of Patent: June 2, 1998Assignee: General Electric CompanyInventors: Eric James Pressman, Sheldon Jay Shafer
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Patent number: 5756801Abstract: Adducts of hydroxyaromatic compounds such as phenol and diaryl carbonates such as diphenyl carbonate are washed with a washing composition comprising a major proportion, typically about 90%, of the hydroxyaromatic compound and a minor proportion, typically about 10%, of the diaryl carbonate.Type: GrantFiled: February 10, 1997Date of Patent: May 26, 1998Assignee: General Electric CompanyInventors: Sheldon Jay Shafer, Eric James Pressman
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Patent number: 5731453Abstract: A diaryl carbonate with a high degree of purity is produced at a high yield by (A) subjecting (a) a diaryl oxalate and a phenol compound or (b) an alkylaryl oxalate to transesterification reaction in one or two stages in the presence of a catalyst to prepare a diaryl oxalate, while removing a by-product from the reaction system; (B) collecting the diaryl oxalate from the resultant reaction product mixture of the step (A); (C) subjecting the diaryl oxalate to a decarbonylation reaction, preferably in the presence of a phosphorous compound-containing catalyst, to convert the diaryl oxalate to a corresponding diaryl carbonate, while removing a reaction by-product comprising carbon monoxide from the reaction system; and (D) collecting the diaryl carbonate from the reaction product mixture of the step (C).Type: GrantFiled: March 10, 1997Date of Patent: March 24, 1998Assignee: Ube Industries, Ltd.Inventors: Keigo Nishihira, Shuji Tanaka, Yuki Nishida, Hirofumi Ii, Satoru Fujitsu, Katsumasa Harada, Ryoji Sugise, Koichi Kashiwagi, Takashi Doi
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Patent number: 5726340Abstract: The present invention relates to a method of producing an aromatic carbonate by reacting an aromatic hydroxy compound, carbon monoxide, and oxygen, wherein the reaction is carried out in the presence of a catalyst comprising:(A) at least one selected from palladium and palladium compounds;(B) at least one lead compound;(C) at least one cobalt compound; and,(D) at least one halide.According to this method an aromatic carbonate which produces only a small amount of impurities and has excellent selectivity can be produced.Type: GrantFiled: March 4, 1997Date of Patent: March 10, 1998Assignee: Mitsubishi Chemical CorporationInventors: Masatoshi Takagi, Katsufumi Kujira, Takahiro Yoneyama, Yuji Ohgomori
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Patent number: 5714627Abstract: A process for producing an aromatic carbonate which comprises: reacting a dialkyl carbonate represented by general formula (1) with an aromatic carboxylic acid aryl ester represented by general formula (2) in the presence of a catalyst to produce an aromatic carbonate represented by one or both of general formulae (3) and (4):R--OCOO--R (1)Ar'--COO--Ar (2)Ar--OCOO--R (3)Ar--OCOO--Ar (4)wherein R represents an alkyl group having from 1 to 4 carbon atoms, and Ar and Ar' each represents an unsubstituted phenyl group or a phenyl group substituted by a substituent selected from the group consisting of alkyl, alkoxy, aryl, aryloxy and a halogen atom.Type: GrantFiled: August 27, 1996Date of Patent: February 3, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masamichi Mizukami, Takuo Ohshida, Hiroaki Ohgi, Hidefumi Harada
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Patent number: 5712406Abstract: Diaryl carbonate and an aromatic hydroxy compound are simultaneously separated from a crude reaction mixture for producing diaryl carbonates by oxidative carbonylation of the aromatic hydroxy compound and containing the diaryl carbonate and excess hydroxy compound together with the catalyst system, consisting of a noble-metal catalyst, co-catalyst, quaternary salt and a base. The crude reaction mixture is mixed with a covalent aprotic extraction agent, a phase separation is carried out into a donor phase containing the catalyst system and a recipient phase containing the diaryl carbonate and the hydroxy compound in concentrated form, and the diaryl carbonate and the hydroxy compound are isolated from the recipient phase.Type: GrantFiled: February 5, 1997Date of Patent: January 27, 1998Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Carsten Hesse, Johann Rechner
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Patent number: 5705091Abstract: Bleaching compositions are provided that comprise peracid activators. The peracid activators are ester derivatives of a carboxylic acid where the oxygen is covalently bound through a polyhydroxy linking group to a leaving group that is displaceable in a peroxygen bleaching solution by perhydroxide anion. When the peracid activator is combined with a source of peroxygen in aqueous solution, then a stain removing peracid is formed. One embodiment of the peracid activator has the structure ##STR1## where R' is a branched or linear C.sub.4-12 alkyl, n is 1 to about 7, and L is a leaving group.Type: GrantFiled: September 11, 1995Date of Patent: January 6, 1998Assignee: The Clorox CompanyInventors: Dale S. Steichen, Richard J. Wiersema
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Patent number: 5684018Abstract: This invention relates to novel acyloxyisopropyl carbamates as bioreversible prodrug moieties for amino drugs and to methods of synthesizng these compounds.Type: GrantFiled: December 13, 1994Date of Patent: November 4, 1997Assignee: Merck & Co., Inc.Inventor: Jose Alexander
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Patent number: 5663480Abstract: A catalyst for producing an aryl ester of a carbonic or carboxylic acid is disclosed, which includes a microporous material containing a metal element belonging to group IV. This catalyst can be used as a heterogeneous catalyst to produce the aryl ester in high yield with industrial advantages. In order to produce the aryl ester using the catalyst, a carbonate or an aliphatic carboxylate is transesterified with an aromatic hydroxy compound, or an aryl carboxylate is transesterified with a carbonate, or an alkyl aryl carbonate is disproportionated by transesterification.Type: GrantFiled: July 11, 1996Date of Patent: September 2, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Hideaki Tsuneki, Masaru Kirishiki, Kenichi Watanabe, Yoshiyuki Onda
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Patent number: 5643946Abstract: Compounds of the formula ##STR1## wherein the substituents are as defined herein, are disclosed. Pharmaceutical compositions and methods of treating allergic and inflammatory diseases are also taught.Type: GrantFiled: May 18, 1995Date of Patent: July 1, 1997Assignee: SmithKline Beecham CorporationInventor: Siegfried Benjamin Christensen, IV
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Patent number: 5606089Abstract: Compounds represented by the general formula (I), as well as intermediates for the synthesis of thereof: ##STR1## where R.sup.1 is a hydrogen atom or an acyl group; R.sup.2 is a lower alkyl group; R.sup.3 is a hydrogen atom or a lower alkyl group; R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl or aryl group; R.sup.2 and R.sup.4, when taken together, may form a 5-membered ring; R.sup.5 and R.sup.6, when taken together, may form a cycloalkyl group or a heterocyclic group in which at least one methylene on the ring of a cycloalkyl group is substituted by an oxygen atom, a sulfur atom or an alkyl-substituted nitrogen atom, provided that R.sup.6 is not present if the ring formed by R.sup.2 and R.sup.4 taken together is a benzofuran ring.Type: GrantFiled: May 18, 1995Date of Patent: February 25, 1997Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Kunio Tamura, Yoshiaki Kato, Mitsutaka Yoshida, Osamu Cynshi, Yasuhiro Ohba
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Patent number: 5565490Abstract: p-Hydroxyaniline derivatives of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is hydrogen, or unsubstituted or substituted alkyl;R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl,OR.sup.5 or NR.sup.6 R.sup.7, whereR.sup.5, R.sup.6 are unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, andR.sup.7 is hydrogen or alkyl,and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests, and also compounds of the formula VI ##STR2## and their salts, processes for their preparation, compositions containing them and their use as intermediates and for controlling pests are described.Type: GrantFiled: November 10, 1994Date of Patent: October 15, 1996Assignee: BASF AktiengesellschaftInventors: Oliver Wagner, Karl Eicken, Norbert G otz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5534653Abstract: p-Hydroxyaniline derivatives of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is unsubstituted or substituted bicycloalkyl or bicycloalkenyl;R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl,OR.sup.5 or NR.sup.5 R.sup.6, whereR.sup.5 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, andR.sup.6 is hydrogen or alkyl,and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests are described.Type: GrantFiled: November 10, 1994Date of Patent: July 9, 1996Assignee: BASF AktiengesellschaftInventors: Oliver Wagner, Karl Eicken, Norbert Gotz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5514710Abstract: The invention describes the synthesis and use of photoactivated (or caged) fluorescent dyes. Upon illumination at less than about 400 nm the caged dyes release highly fluorescent, water soluble hydroxypyrenesulfonic acid dyes according to the following equation: ##STR1## X, Y, and Z are independently sulfonic acid, a sulfonic acid salt, a hydroxyl group, or hydrogen, with at least one of X, Y, and Z being a sulfonic acid or sulfonic acid salt. LINK is either an ether linkage or a carbonate linkage. BLOCK is a caging group whose photolysis results in liberation of a free hydroxypyrenesulfonic acid dye.The caged fluorescent dyes are useful for application in aqueous solutions, including fluids of biological origin. The caged dyes of the present invention are especially useful for flow tagging velocimetry.Type: GrantFiled: January 11, 1994Date of Patent: May 7, 1996Assignee: Molecular Probes, Inc.Inventors: Richard P. Haugland, Kyle R. Gee
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Patent number: 5506263Abstract: Benzyl derivatives of the formula I ##STR1## where A is CH.sub.2, CHCl, CH-alkyl, CH-alkoxy, CH-alkylthio or N-alkoxy,B is OH, alkylthio, alkoxy or alkylamino,U, V, W are hydrogen, halogen, alkyl or alkoxy,D is ##STR2## where R' is hydrogen or alkyl andR is hydrogen, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, aryl, arylalkyl, hetaryl, hetaryl-alkyl, hetaryloxyalkyl or heterocyclyl, and fungicides containing these compounds.Type: GrantFiled: December 14, 1994Date of Patent: April 9, 1996Assignee: BASF AktiengesellschaftInventors: Horst Wingert, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5502232Abstract: Diaryl carbonates can be prepared by reacting aromatic hydroxy compounds with CO and O.sub.2 at elevated temperature over a noble metal catalyst in the presence of a base, a quaternary salt, a cocatalyst and a dessicant. According to the invention, the noble metal catalyst is activated with CO in the presence of the quaternary salt and optionally in the presence of the cocatalyst. In a particular process variant, the base used is a preformed alkali metal phenoxide.Type: GrantFiled: November 15, 1994Date of Patent: March 26, 1996Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Joachim Dohm, Carsten Hesse, Johann Rechner, Dieter Kaufmann
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Patent number: 5498789Abstract: The present invention relates to a method of producing an aromatic carbonate by reacting an aromatic hydroxy compound, carbon monoxide and oxygen using a catalyst system for suppressing the production of aryl aromatic o-hydroxycarboxylate as a by-product. The catalyst system consists of the following compounds:(A) at least one selected from palladium and palladium compounds;(B) at least one selected from lead compounds; and(C) at least one halide selected from quaternary ammonium halides and quaternary phosphonium halides; and if required,(D) at least one selected from copper and copper compounds.The method of the present invention can increase the yield of an aromatic carbonate per palladium (the turnover number of palladium).Type: GrantFiled: November 28, 1994Date of Patent: March 12, 1996Assignee: Mitsubishi Chemical CorporationInventors: Masatoshi Takagi, Hidekazu Miyagi, Yuji Ohgomori, Hiroshi Iwane
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Patent number: 5498742Abstract: The invention relates to a process for the continuous preparation of diaryl carbonates by reaction of an aromatic hydroxyl compound with carbon monoxide and oxygen in the presence of a catalyst containing a noble metal of group VIIIb of the Periodic Table of the Elements, a quaternary salt, a cocatalyst and a base. The catalyst is activated by treatment with carbon monoxide in the liquid phase. The reaction water is removed by excess reaction gas.Type: GrantFiled: January 27, 1995Date of Patent: March 12, 1996Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Carsten Hesse, Johann Rechner, Reinhard Schomacker, Paul Wagner, Dieter Kaufmann
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Patent number: 5481013Abstract: Compounds of the formula ##STR1## in which A is oxygen, sulfur or --NR.sub.1 --;B is C.sub.2 -C.sub.6 alkylene,D-E is --O--E, --S--E, --O--CH.sub.2 --E, --O--C(.dbd.O)--E, --O--C(.dbd.O)--O--E, --O--C(.dbd.O)--N(H)--E or --O--C(.dbd.S)--N(H)--E;E is phenyl; phenyl which is substituted by one to three substituents; a five-membered aromatic heterocycle having one to three hetero atoms; a five-membered aromatic heterocycle which has one to three hetero atoms and which is substituted by one or two substituents; a six-membered aromatic heterocycle which has one to three nitrogen atoms; or a six-membered aromatic heterocycle which has one to three nitrogen atoms and which is substituted by one or two substituents;L is halogen or methyl;X is fluorine;Y is chlorine or fluorine;Z is hydrogen, fluorine or methyl;m is the number zero, one, two, three, four or five;n is the number zero, one or two andR.sub.1 is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: June 23, 1993Date of Patent: January 2, 1996Assignee: Ciba-Geigy CorporationInventors: Peter Maienfisch, Thomas Pitterna, Manfred Boger
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Patent number: 5478961Abstract: Carbonates with aromatic ester groups may be prepared by reacting aromatic monohydroxy compounds with phosgene or with chloroformates of aromatic monohydroxy compounds, wherein the process is performed at a temperature in the range 50.degree.-350.degree. C. in the presence of aluminosilicates as heterogeneous catalysts.Type: GrantFiled: July 11, 1994Date of Patent: December 26, 1995Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Norbert Schon, Hans-Josef Buysch
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Patent number: 5473094Abstract: Carbonates with aromatic ester groups may be prepared by reacting aromatic monohydroxy compounds with phosgene or with chloroformates of aromatic monohydroxy compounds, wherein reaction takes place at a temperature in the range 50.degree. to 350.degree. C. in the presence of aluminum oxides as heterogeneous catalysts.Type: GrantFiled: July 7, 1994Date of Patent: December 5, 1995Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Norbert Schon, Hans-Josef Buysch
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Patent number: 5463102Abstract: Organic carbonates containing at least one aromatic ester group can be obtained in a continuous manner from carbonates containing at least one aliphatic ester group and a phenolic compound in the presence of a transesterification catalyst known per se by carrying out the reaction in at least two stirred containers connected one behind the other in such a way that, in each case, the phenolic compound is metered in liquid form into the first stirred container and the carbonate containing at least one aliphatic ester group is metered in liquid form into one or more of the stirred containers. The carbonate containing at least one aromatic ester group is removed in liquid form from the last stirred container. Volatile reaction products, for example alcohol which has been cleaved out or a dialkyl carbonate are removed in gaseous form from one or more stirred containers.Type: GrantFiled: January 18, 1994Date of Patent: October 31, 1995Assignee: Bayer AktiengesellschaftInventors: Norbert Schon, Johann Rechner, Paul Wagner, Hans-Josef Buysch, Hans-Erich Gasche, Ricarda Leiberich
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Patent number: 5414153Abstract: Phenolic compounds, e.g., the phenols and phenol ethers, are selectively hydroxylated whereby the amounts of the final product para isomer are enhanced, for example in favor of hydroquinone versus pyrocatechol in the event of the hydroxylation of phenol, by reacting such phenolic compounds with hydrogen peroxide, advantageously in a polar, aprotic, organic solvent reaction medium, in the presence of a catalytically effective amount of a sulfonated polymer and a cocatalytically effective amount of an aromatic ketone compound.Type: GrantFiled: April 5, 1993Date of Patent: May 9, 1995Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5405986Abstract: A catalyst for synthesizing a carbonic diester includes at least one copper compound selected from among copper oxides, copper hydroxides, a salt of copper with a weak acid consisting of the elements other than halogen such as copper borates, and complexes or complex salts consisting of the elements other than halogen and formed with copper or a copper compound a and ligand. The catalyst has a high activity, a high reaction selectivity and excellent stability with a minimal risk of corroding equipment. The catalyst can include, as a co-catalyst component, a platinum-group metal such as palladium or a halogen-free platinum-group metal compound such as palladium acetate. The catalyst component may be supported on a carrier, for example, an activated carbon. A carbonic diester is advantageously produced by allowing an alcohol to react with carbon monoxide and oxygen in the presence of the catalyst.Type: GrantFiled: January 24, 1994Date of Patent: April 11, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Shingo Oda, Mitsuru Ohno
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Patent number: 5399734Abstract: Improved yields of aromatic organic carbonates made by the palladium catalyzed direct carbonylation of aromatic organic hydroxy compounds can be achieved if the total gas pressure and partial pressure of carbon monoxide and oxygen are substantially maintained during the reaction.Type: GrantFiled: July 20, 1993Date of Patent: March 21, 1995Assignee: General Electric CompanyInventors: Joseph A. King, Jr., Patricia D. Mackenzie, Eric J. Pressman
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Patent number: 5362901Abstract: The title compounds are prepared from organic carbonates having at least one aliphatic ester group and phenolic compounds by transesterification in the presence of a transesterification catalyst known per se at 60.degree.-320.degree. C. in a column-type reactor with multiple recycling of the reaction products into this reactor with intermediate storage of the product streams.Type: GrantFiled: May 25, 1993Date of Patent: November 8, 1994Assignee: Bayer AktiengesellschaftInventors: Paul Wagner, Norbert Schon, Hans-Josef Buysch
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Patent number: 5292915Abstract: The invention relates to compounds containing carbonate groups and carbonyl groups and having the general formula ##STR1## in which R stands for a C.sub.1 -C.sub.4 -alkyl radical, an aryl radical, or a radical R.sup.1, whereR.sup.1 has the following formula ##STR2## in which R.sup.2 to R.sup.6 stand for H, alkyl, OH, O-alkyl, SH, S-alkyl, halogen, N(alkyl).sub.2, or N(alkyl)(aryl) and at least one but not more than three of the radicals R.sup.2 to R.sup.6 stand for a radical of the formula ##STR3## in which A, B and C stand for alkylene, cycloalkylene, oxaalkylene, polyoxaalkylene or arylene, k and l both stand for an integer from 1 to 80, and the end group Z stands for alkyl, aryl, alkoxycarbonyl, alkoxycarbonyloxy, or aryl.These compounds are suitable for use as emulsifiers for dispersions.Type: GrantFiled: February 4, 1992Date of Patent: March 8, 1994Assignee: BASF AktiengesellschaftInventors: Andreas Boettcher, Manfred Schwartz
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Patent number: 5284965Abstract: A process is described for preparing aromatic carbonates by transesterification of aliphatic carbonates with phenolic compounds in the presence of titanium compounds known per se, in which, before work-up, the transesterification mixture is cooled to a temperature below 120.degree. C., during which the mixture must remain liquid, the titanium-containing precipitate which is deposited is separated off, and the aromatic carbonate is then obtained by methods which are conventional per se.Type: GrantFiled: March 3, 1993Date of Patent: February 8, 1994Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Norbert Schon, Johann Rechner
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Patent number: 5281742Abstract: Disclosed are fluorobenzene derivatives, which are important intermediates for producing herbicidal oxazolidinedione derivatives, and methods of producing them. The fluorobenzene derivatives include compounds of a formula (11): ##STR1## where X is a halogen atom, R.sup.3 is a nitro, amino or isocyanato group or R.sup.1 OCONH, and R.sup.1 is an alkyl or phenyl group. Via the intermediates of the invention, oxazolidinedione derivatives can be produced with high yield.Type: GrantFiled: January 21, 1992Date of Patent: January 25, 1994Assignees: Sagami Chemical Research Center, Kaken Pharmaceutical Co., Ltd.Inventors: Kenji Hirai, Tomoyuki Yano, Mitsuo Yamashita, Emiko Ejiri, Tomoko Tateno, Kiyomi Aizawa
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Patent number: 5260473Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of an amidine or guanidine base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.Type: GrantFiled: November 16, 1992Date of Patent: November 9, 1993Assignee: Monsanto CompanyInventors: William D. McGhee, Dennis P. Riley
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Patent number: 5258542Abstract: Polymerizable carbonate compounds of the formula: ##STR1## wherein A is an aromatic polycycle, R.sup.1 and R.sup.2 are independently hydrogen atom or alkyl, and n is 1, 2 or 3, are disclosed. They are useful as a component of nonemanating, self-curing and heat resistant resin compositions.Type: GrantFiled: August 3, 1992Date of Patent: November 2, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki, Satoshi Urano, Ryuzo Mizuguchi