Additional Chalcogen Bonded Directly To The Benzene Ring Patents (Class 558/271)
  • Patent number: 6114563
    Abstract: 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: Grant
    Filed: April 29, 1999
    Date of Patent: September 5, 2000
    Assignee: General Electric Co.
    Inventors: James Lawrence Spivack, Donald Wayne Whisenhunt, Jr., James Norman Cawse, Bruce Fletcher Johnson, Kirill Shalyaev
  • Patent number: 6093842
    Abstract: 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: Grant
    Filed: September 25, 1998
    Date of Patent: July 25, 2000
    Assignee: General Electric Company
    Inventors: Martin H. Oyevaar, Bill W. To, Michael F. Doherty, Michael F. Malone
  • Patent number: 6034262
    Abstract: 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: Grant
    Filed: December 22, 1998
    Date of Patent: March 7, 2000
    Assignee: General Electric Company
    Inventor: Phillip Moreno
  • Patent number: 6001768
    Abstract: 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: Grant
    Filed: March 29, 1996
    Date of Patent: December 14, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Carsten Hesse, Jorg-Dietrich Jentsch, Johann Rechner, Eberhard Zirngiebl
  • Patent number: 5981788
    Abstract: 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: Grant
    Filed: November 3, 1997
    Date of Patent: November 9, 1999
    Assignee: General Electric Company
    Inventors: John Yaw Ofori, Sheldon Jay Shafer, Eric James Pressman, Ganesh Kailasam, Julia Lam Lee
  • Patent number: 5917078
    Abstract: 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: Grant
    Filed: September 25, 1998
    Date of Patent: June 29, 1999
    Assignee: General Electric Company
    Inventors: Richard A. Battista, Francis S. Lo, Robert L. Tatterson
  • Patent number: 5917077
    Abstract: 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: Grant
    Filed: June 1, 1998
    Date of Patent: June 29, 1999
    Assignee: General Electric Company
    Inventors: Raghunath Vitthal Chaudhari, Sunil Purushottam Gupte, Ashutosh Anant Kelkar, Subbareddiar Kanagasabapathy, Subramaniam Radhakrishnan
  • Patent number: 5908952
    Abstract: 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: Grant
    Filed: March 24, 1997
    Date of Patent: June 1, 1999
    Assignee: General Electric Company
    Inventors: Eric James Pressman, Sheldon Jay Shafer
  • Patent number: 5900501
    Abstract: 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: Grant
    Filed: February 13, 1997
    Date of Patent: May 4, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Hans-Josef Buysch, Steffen Kuhling, Gottfried Zaby
  • Patent number: 5898079
    Abstract: 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: Grant
    Filed: September 12, 1997
    Date of Patent: April 27, 1999
    Assignee: General Electric Company
    Inventors: Eric James Pressman, Sheldon Jay Shafer
  • Patent number: 5898080
    Abstract: 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: Grant
    Filed: August 27, 1997
    Date of Patent: April 27, 1999
    Assignee: General Electric Company
    Inventors: Eric James Pressman, Sheldon Jay Shafer
  • Patent number: 5877140
    Abstract: 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: Grant
    Filed: March 20, 1997
    Date of Patent: March 2, 1999
    Inventors: Frederick Edward Hardy, Barry Thomas Ingram, Christian Leo Marie Vermote
  • Patent number: 5834615
    Abstract: 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: Grant
    Filed: September 24, 1997
    Date of Patent: November 10, 1998
    Assignee: Ube Industries, Ltd.
    Inventors: Keigo Nishihira, Shuji Tanaka, Katsumasa Harada, Ryoji Sugise
  • Patent number: 5831111
    Abstract: 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: Grant
    Filed: May 5, 1997
    Date of Patent: November 3, 1998
    Assignee: Bayer AG
    Inventors: Pieter Ooms, Eric Bischof, Hans-Josef Buysch, Steffen Kuhling, Gottfried Zaby, Wolfgang Jakob, Jurgen Dahmer, Norbert Schon
  • Patent number: 5824816
    Abstract: 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: Grant
    Filed: April 1, 1997
    Date of Patent: October 20, 1998
    Assignee: Bayer AG
    Inventors: Hans-Josef Buysch, Carsten Hesse, Johann Rechner, Hans-Peter Wirges
  • Patent number: 5821377
    Abstract: 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: Grant
    Filed: April 1, 1997
    Date of Patent: October 13, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Carsten Hesse, Johann Rechner
  • Patent number: 5792883
    Abstract: 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: Grant
    Filed: October 6, 1997
    Date of Patent: August 11, 1998
    Assignee: Ube Industries, Ltd.
    Inventors: Katsumasa Harada, Ryoji Sugise, Koichi Kashiwagi, Takashi Doi, Sadao Niida, Toshio Kurafuji
  • Patent number: 5792762
    Abstract: The invention provides dihydronaphthofluorene compounds, formulations, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, and cardiovascular-related pathological conditions.
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: August 11, 1998
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Thomas Alan Crowell, Charles David Jones
  • Patent number: 5777162
    Abstract: 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: Grant
    Filed: November 12, 1996
    Date of Patent: July 7, 1998
    Assignee: Zeneca Limited
    Inventors: Ian Richard Matthews, Christopher Richard Ayles Godfrey, John Martin Clough
  • Patent number: 5760272
    Abstract: 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: Grant
    Filed: March 24, 1997
    Date of Patent: June 2, 1998
    Assignee: General Electric Company
    Inventors: Eric James Pressman, Sheldon Jay Shafer
  • Patent number: 5756801
    Abstract: 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: Grant
    Filed: February 10, 1997
    Date of Patent: May 26, 1998
    Assignee: General Electric Company
    Inventors: Sheldon Jay Shafer, Eric James Pressman
  • Patent number: 5731453
    Abstract: 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: Grant
    Filed: March 10, 1997
    Date of Patent: March 24, 1998
    Assignee: Ube Industries, Ltd.
    Inventors: Keigo Nishihira, Shuji Tanaka, Yuki Nishida, Hirofumi Ii, Satoru Fujitsu, Katsumasa Harada, Ryoji Sugise, Koichi Kashiwagi, Takashi Doi
  • Patent number: 5726340
    Abstract: 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: Grant
    Filed: March 4, 1997
    Date of Patent: March 10, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masatoshi Takagi, Katsufumi Kujira, Takahiro Yoneyama, Yuji Ohgomori
  • Patent number: 5714627
    Abstract: 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: Grant
    Filed: August 27, 1996
    Date of Patent: February 3, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masamichi Mizukami, Takuo Ohshida, Hiroaki Ohgi, Hidefumi Harada
  • Patent number: 5712406
    Abstract: 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: Grant
    Filed: February 5, 1997
    Date of Patent: January 27, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Carsten Hesse, Johann Rechner
  • Patent number: 5705091
    Abstract: 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: Grant
    Filed: September 11, 1995
    Date of Patent: January 6, 1998
    Assignee: The Clorox Company
    Inventors: Dale S. Steichen, Richard J. Wiersema
  • Patent number: 5684018
    Abstract: This invention relates to novel acyloxyisopropyl carbamates as bioreversible prodrug moieties for amino drugs and to methods of synthesizng these compounds.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: November 4, 1997
    Assignee: Merck & Co., Inc.
    Inventor: Jose Alexander
  • Patent number: 5663480
    Abstract: 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: Grant
    Filed: July 11, 1996
    Date of Patent: September 2, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hideaki Tsuneki, Masaru Kirishiki, Kenichi Watanabe, Yoshiyuki Onda
  • Patent number: 5643946
    Abstract: 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: Grant
    Filed: May 18, 1995
    Date of Patent: July 1, 1997
    Assignee: SmithKline Beecham Corporation
    Inventor: Siegfried Benjamin Christensen, IV
  • Patent number: 5606089
    Abstract: 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: Grant
    Filed: May 18, 1995
    Date of Patent: February 25, 1997
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Kunio Tamura, Yoshiaki Kato, Mitsutaka Yoshida, Osamu Cynshi, Yasuhiro Ohba
  • Patent number: 5565490
    Abstract: 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: Grant
    Filed: November 10, 1994
    Date of Patent: October 15, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Oliver Wagner, Karl Eicken, Norbert G otz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5534653
    Abstract: 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: Grant
    Filed: November 10, 1994
    Date of Patent: July 9, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Oliver Wagner, Karl Eicken, Norbert Gotz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5514710
    Abstract: 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: Grant
    Filed: January 11, 1994
    Date of Patent: May 7, 1996
    Assignee: Molecular Probes, Inc.
    Inventors: Richard P. Haugland, Kyle R. Gee
  • Patent number: 5506263
    Abstract: 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: Grant
    Filed: December 14, 1994
    Date of Patent: April 9, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5502232
    Abstract: 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: Grant
    Filed: November 15, 1994
    Date of Patent: March 26, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Joachim Dohm, Carsten Hesse, Johann Rechner, Dieter Kaufmann
  • Patent number: 5498789
    Abstract: 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: Grant
    Filed: November 28, 1994
    Date of Patent: March 12, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masatoshi Takagi, Hidekazu Miyagi, Yuji Ohgomori, Hiroshi Iwane
  • Patent number: 5498742
    Abstract: 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: Grant
    Filed: January 27, 1995
    Date of Patent: March 12, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Carsten Hesse, Johann Rechner, Reinhard Schomacker, Paul Wagner, Dieter Kaufmann
  • Patent number: 5481013
    Abstract: 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: Grant
    Filed: June 23, 1993
    Date of Patent: January 2, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Thomas Pitterna, Manfred Boger
  • Patent number: 5478961
    Abstract: 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: Grant
    Filed: July 11, 1994
    Date of Patent: December 26, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Norbert Schon, Hans-Josef Buysch
  • Patent number: 5473094
    Abstract: 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: Grant
    Filed: July 7, 1994
    Date of Patent: December 5, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Norbert Schon, Hans-Josef Buysch
  • Patent number: 5463102
    Abstract: 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: Grant
    Filed: January 18, 1994
    Date of Patent: October 31, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Schon, Johann Rechner, Paul Wagner, Hans-Josef Buysch, Hans-Erich Gasche, Ricarda Leiberich
  • Patent number: 5414153
    Abstract: 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: Grant
    Filed: April 5, 1993
    Date of Patent: May 9, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher
  • Patent number: 5405986
    Abstract: 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: Grant
    Filed: January 24, 1994
    Date of Patent: April 11, 1995
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Shingo Oda, Mitsuru Ohno
  • Patent number: 5399734
    Abstract: 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: Grant
    Filed: July 20, 1993
    Date of Patent: March 21, 1995
    Assignee: General Electric Company
    Inventors: Joseph A. King, Jr., Patricia D. Mackenzie, Eric J. Pressman
  • Patent number: 5362901
    Abstract: 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: Grant
    Filed: May 25, 1993
    Date of Patent: November 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Paul Wagner, Norbert Schon, Hans-Josef Buysch
  • Patent number: 5292915
    Abstract: 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: Grant
    Filed: February 4, 1992
    Date of Patent: March 8, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Boettcher, Manfred Schwartz
  • Patent number: 5284965
    Abstract: 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: Grant
    Filed: March 3, 1993
    Date of Patent: February 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Norbert Schon, Johann Rechner
  • Patent number: 5281742
    Abstract: 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: Grant
    Filed: January 21, 1992
    Date of Patent: January 25, 1994
    Assignees: Sagami Chemical Research Center, Kaken Pharmaceutical Co., Ltd.
    Inventors: Kenji Hirai, Tomoyuki Yano, Mitsuo Yamashita, Emiko Ejiri, Tomoko Tateno, Kiyomi Aizawa
  • Patent number: 5260473
    Abstract: 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: Grant
    Filed: November 16, 1992
    Date of Patent: November 9, 1993
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Dennis P. Riley
  • Patent number: 5258542
    Abstract: 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: Grant
    Filed: August 3, 1992
    Date of Patent: November 2, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki, Satoshi Urano, Ryuzo Mizuguchi