Carbocyclic Ring Containing Patents (Class 205/456)
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Publication number: 20140251821Abstract: Methods, equipment, and reagents for preparing organic compounds using custom electrolytes based on different ionic liquids in electrolytic decarboxylation reactions are disclosed.Type: ApplicationFiled: March 12, 2014Publication date: September 11, 2014Applicant: Ceramatec, Inc.Inventors: Sai Bhavaraju, James Mosby, Patrick McGuire, Mukund Karanjikar, Daniel Taggart, Jacob Staley
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Publication number: 20120016162Abstract: The present invention relates to 3-tert-butylbenzaldehyde dimethyl acetal and to 3-tert-butylbenzyl methyl ether and to an electrochemical method for producing 3-tert-butyl-benzaldehyde dimethyl acetal and intermediates passed through in said method.Type: ApplicationFiled: March 27, 2009Publication date: January 19, 2012Applicant: BASF SEInventors: Florian Stecker, Andreas Fischer, Jörg Botzem, Ulrich Griesbach, Ralf Pelzer
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Publication number: 20090101516Abstract: The present invention relates to methods and apparatus for activation of a low reactivity, non-polar chemical compound. In one example embodiment, the method comprises introducing the low reactivity chemical compound to a catalyst. At least one of (a) an oxidizing agent or a reducing agent and (b) a polar compound is provided to the catalyst and the chemical compound. An alternating current is applied to the catalyst to produce an activation reaction in the chemical compound. This activation reaction produces a useful product. The present invention also relates to a method for oxidizing aromatic compounds by electrocatalysis to oxidized products.Type: ApplicationFiled: September 18, 2008Publication date: April 23, 2009Applicants: The University of Connecticut, Catelectric Corp.Inventors: Steven Lawrence Suib, Boxun Hu, Victor Stancovski
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Patent number: 7192512Abstract: A process is provided for the preparation of trialkyl orthocarboxylates by the electrochemical oxidation of alpha, beta-diketones or alpha, beta-hydroxyketones, the keto group being present in the form of a ketal group derived from C1- to C4-alkylalcohols and the hydroxyl group optionally being present in the form of an ether group derived from C1- to C4-alkylalcohols (ketals K), in the presence of C1- to C4-alcohols (alcohols A), the molar ratio of the ketals K to the alcohols A in the electrolyte being 0.2:1 to 10:1.Type: GrantFiled: September 5, 2001Date of Patent: March 20, 2007Assignee: BASF AktiengesellschaftInventors: Andreas Fischer, Hermann Pütter
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Patent number: 7052593Abstract: The present invention provides an electrochemical method for producing diaryl iodonium compounds wherein application of an electric current to an electrochemical cell containing a reaction mixture composed of a solvent, an iodoaryl compound and an electrolyte forms an oxidizing agent in situ. In this first step, the oxidizing agent is subsequently converted into a stable oxidized iodoaryl intermediate, typically an iodosyl compound. The electric potential is removed and in a second step a target aryl compound is introduced to the reaction mixture to react with the oxidized iodoaryl intermediate to form a diaryl iodonium compound.Type: GrantFiled: January 7, 2004Date of Patent: May 30, 2006Assignee: Cornell Development Corporation LLCInventors: Leonard H. Wojcik, Jr., David D. Cornell
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Patent number: 6916953Abstract: Process for preparing organic isocyanates, which comprises the steps (a) making available a first partial amount of chlorine, with the chlorine of this first partial amount having a content of free and bound bromine and iodine of <400 ppm; (b) making available a second partial amount of chlorine; (c) reacting the first and second partial amounts of chlorine with carbon monoxide to form phosgene; (d) reacting the phosgene from step (c) with one or more primary amines to form the corresponding isocyanates and hydrogen chloride; (e) separating off and, if necessary, purifying the isocyanates formed in step (d); (f) separating off and, if necessary, purifying the hydrogen chloride formed in step (d); (g) catalytically oxidizing at least part of the hydrogen chloride separated off in step (e) by means of oxygen to form chlorine; (h) separating off the chlorine formed in step (g) and using at least a partial amount of the chlorine which has been separated off as second partial amount of chlorine in step (b).Type: GrantFiled: August 27, 2002Date of Patent: July 12, 2005Assignee: BASF AktiengesellschaftInventors: Christian Walsdorff, Martin Fiene, Eckhard Ströfer, Klaus Harth, Jan D. Jacobs, Filip Deberdt
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Patent number: 6419814Abstract: Organoiodonium salts, including certain novel symmetrical and unsymmetrical diaryliodonium;. polyiodonium and cyclic iodonium salts are synthesized by a significantly improved electrochemical coupling reaction which provides greater control and selectivity over the end product produced. Reaction mixtures comprising aryliodides and/or aromatic substrates are electrolyzed in novel reaction mediums comprising strong acid electrolyte, lower carboxylic acid, and preferably in the presence of acid anhydride in amounts >10 percent by-weight, and up to 50 percent by-weight or more, to provide a high degree of product selectivity, and at yields which can even be quantitative. The methods are conducted by introducing the electrolysis reaction mixture into an undivided electrochemical cell equipped with a cathode and preferably a conductive carbon anode.Type: GrantFiled: November 2, 2000Date of Patent: July 16, 2002Assignee: Cornell Development LLCInventors: Derek Pletcher, Norman L. Weinberg
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Patent number: 6267866Abstract: An electrode for electrochemical uses is made of a conductive metal mesh coated with boron-doped diamond. The electrode may be used in electrochemical reactions either as a cathode or as an anode, or can be used with an alternating current.Type: GrantFiled: October 14, 1999Date of Patent: July 31, 2001Assignee: The United States of America as represented by the Secretary of the NavyInventors: John W. Glesener, Paul M. Natishan, William E. O'Grady, Arthur A. Morrish, Brian R. Stoner, Patrick L. Hagans
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Patent number: 6214196Abstract: A method of producing a bisphosphine oxide by performing a koble electrolysis coupling reaction to a phosphine oxide carboxylic acid represented by the general formula (1): wherein the bisphosphine oxide is represented by the following general formula (2):Type: GrantFiled: August 9, 1999Date of Patent: April 10, 2001Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Masashi Sugiya, Hiroyuki Nohira
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Patent number: 6010612Abstract: A process and a system produces isocyanate and converts anhydrous hydrogen chloride, which is a by-product of isocyanate production, to chlorine gas in an electrochemical cell. The chlorine is recycled to the isocyanate process. Any unreacted anhydrous hydrogen chloride may be recycled to the electrochemical cell. By recycling the anhydrous hydrogen chloride and the chlorine, the process and system are able to reduce the cost of producing isocyanate. In addition, this process and system process eliminate or at least substantially minimize the problems associated with disposal of anhydrous hydrogen chloride by turning it into a useful starting material in the isocyanate process.Type: GrantFiled: October 1, 1997Date of Patent: January 4, 2000Assignee: E.I. du Pont de Nemours and CompanyInventors: Francisco Jose Freire, Bruce Arthur Kaiser, Vinci Martinez Felix, Dennie Turin Mah, James Arthur Trainham, Clarence Garlan Law, Jr., John Scott Newman
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Patent number: 5997715Abstract: Describes a method of electrochemically converting .alpha.-halohydrins, e.g., 1-chloro-2-hydroxypropane and 1,3-dichloro-2-hydroxypropane, to epoxides, e.g., propylene oxide and epichlorohydrin. A three compartment electrolytic cell is provided having (1) a catholyte compartment containing a cathode assembly comprising a cathode and anion exchange membrane, (2) an anolyte compartment containing an anode assembly comprising an anode and a cation exchange membrane, and (3) an intermediate compartment partitioned from the catholyte and anolyte compartments by the anion and cation exchange membranes respectively. An aqueous solution of .alpha.-halohydrin is charged to the catholyte compartment, while hydrogen halide solutions are charged to the intermediate and anolyte compartments. Direct current is passed through the electrolytic cell and an aqueous solution comprising epoxide is removed from the catholyte compartment.Type: GrantFiled: July 9, 1998Date of Patent: December 7, 1999Assignee: PPG Industries Ohio, Inc.Inventors: David G. Roberts, Peter C. Foller, Robert H. Tang, Yingchao Zhang, James R. Franks
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Patent number: 5997716Abstract: Described is a method of electrochemically converting .alpha.-halohydrins, e.g., 1-chloro-2-hydroxypropane and 1,3-dichloro-2-hydroxypropane, to epoxides, e.g., propylene oxide and epichlorohydrin. A three compartment electrolytic cell is provided having (1) a catholyte compartment containing a cathode assembly comprising a cathode and an anion exchange membrane, (2) an anode compartment containing an anode assembly comprising either (a) a hydrogen consuming gas diffusion anode and a current collecting electrode or (b) a hydrogen consuming gas diffusion anode which is fixedly held between a hydraulic barrier and a current collecting electrode, and (3) an intermediate compartment separated from the catholyte and anode compartments by the anion exchange membrane and either (i) the hydrogen consuming gas diffusion anode or (ii) the hydraulic barrier respectively. An aqueous solution of .alpha.Type: GrantFiled: July 9, 1998Date of Patent: December 7, 1999Assignee: PPG Industries Ohio, Inc.Inventors: David G. Roberts, Peter C. Foller, Robert H. Tang, Yingchao Zhang
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Patent number: 5972195Abstract: Describes a method of electrochemically converting .alpha.-halohydrin, e.g., 1-chloro-2-hydroxypropane and 1,3-dichloro-2-hydroxypropane, to epoxide, e.g., propylene oxide and epichlorohydrin. An aqueous solution of .alpha.-halohydrin is charged to the catholyte compartment of an electrolytic cell, which contains a cathode, hydrogen gas is charged to the anode compartment of the cell, which contains an anode assembly comprising a hydrogen consuming gas diffusion anode fixedly held between a current collecting electrode and an anion exchange membrane. The catholyte and anode compartments of the cell are separated by the anion exchange membrane. An aqueous solution containing epoxide is removed from the catholyte compartment.Type: GrantFiled: July 9, 1998Date of Patent: October 26, 1999Assignee: PPG Industries Ohio, Inc.Inventors: David G. Roberts, Peter C. Foller, Robert H. Tang, Yingchao Zhang
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Patent number: 5874212Abstract: Simple methods of detecting single base pair mutations and other mutations in nucleic acid sequences are provided comprising generating a sample which may comprise heteroduplexes and homoduplexes and performing gel electrophoresis on the sample. The sample may be analyzed for one or more isolated high-melting domains prior to performance of gel electrophoresis. Kits are also provided.Type: GrantFiled: June 6, 1995Date of Patent: February 23, 1999Assignee: Thomas Jefferson UniversityInventors: Darwin J. Prockop, Matthew J. Rock, Arupa Ganguly
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Patent number: 5705049Abstract: An integrated process for oxidizing aromatic and alkyl aromatic compounds to form carbonyl containing reaction products comprising the reaction of quadravalent cerium with a reactant stream containing an aromatic or alkyl aromatic compound and using a high degree of mixing, followed by the electrolytic regeneration of the reduced cerium ion in a cell under near turbulent or turbulent flow conditions at high solution velocities relative to the anode. The preferred cell structure for accomplishing the electrolysis utilizes an turbulence promoting anode arrangement which allows for the anolyte to flow past the anode under the conditions mentioned, and a reduced area cathode whereby the anode and cathode compartments need not be separated by an ion exchange membrane.Type: GrantFiled: April 30, 1996Date of Patent: January 6, 1998Assignee: Hydro-QuebecInventor: Stephen Harrison
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Patent number: 5700364Abstract: A process for synthesizing the compounds ##STR1## wherein X is halo, consists of, at a minimum, electrochemical oxidation of the allyl acetonide reactant with halide salt in an aqueous system, the desired compounds being useful as intermediates for the synthesis of inhibitors of renin or HIV protease or other proteases.Type: GrantFiled: October 30, 1996Date of Patent: December 23, 1997Assignee: Merck & Co., Inc.Inventor: Kai Rossen
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Patent number: 5660711Abstract: A process is described for preparing 3-exomethylene cephalosporanic acid derivatives for use in the synthesis of cephalosporin antibiotics such as ceftibuten. The process comprises electrochemical reduction of a compound of the formula (IV) ##STR1## wherein: R.sup.3 is CH.sub.3 C(O)--; ##STR2## is an optional sulfoxide group; n is 2 or 3; R.sup.1 is H and R is H or NHR.sup.2, where R.sup.2 is H or a protecting group selected from C.sub.6 H.sub.5 CH.sub.2 OC(O)--, C.sub.6 H.sub.5 C(O)-- or C.sub.1 -C.sub.6 alkoxy-C(O)--; or wherein R and R.sup.1 together with the carbon atom to which they are attached comprise --C(O)--, and produces the desired 3-exomethylene compounds with low levels of the corresponding 3-methyl tautomers.Type: GrantFiled: December 8, 1995Date of Patent: August 26, 1997Assignee: Schering CorporationInventors: Derek Walker, Junning Lee, Charles R. Martin, Haiyan Zhang, Loris Sogli, Ermanno Bernasconi, Vinod Parakkal Menon
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Patent number: 5571400Abstract: The invention relates to a process for the electrosynthesis of an aldehyde of the formula (I)R.sup.1 --CHO (I)in which R.sup.1 is an aryl or alkyl radical, by electrolysis of an organic halide of the formula (II)R.sup.1 --Hal (II)in which Hal is chlorine or bromineand of an N,N-disubstituted formamide of the formula (III) ##STR1## in which R.sup.2 and R.sup.3 are alkyl or aryl in a cell which is equipped with electrodes and has a chamber, the anode being self-consuming and being composed of a reducing metal, wherein the cathode is composed of lead.Type: GrantFiled: August 16, 1995Date of Patent: November 5, 1996Assignee: Hoechst AktiengesellschaftInventor: Thomas Karcher
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Patent number: 5558754Abstract: A method for preparing 3-alkyl-2,6-dichloroacylanilides by electrolytic debromination of 3-alkyl-4-bromo-2,6-dichloroacylanilides.A method for preparing a 3-alkyl-2,6-dichloroacylanilide of the formula I ##STR1## in which R.sup.1, R.sup.2 are, independently of one another, (C.sub.1 -C.sub.4)-alkyl, by bromoalkylacylanilides of the formula II ##STR2## in which R.sup.1, R.sup.2 have the above-specified meaning, being electrolytically debrominated.Type: GrantFiled: November 29, 1994Date of Patent: September 24, 1996Assignee: Hoechst AktiengesllschaftInventor: Thomas Karcher
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Patent number: 5516407Abstract: An integrated process for oxidizing aromatic and alkyl aromatic compounds to form carbonyl containing reaction products comprising the reaction of quadravalent cerium with a reactant stream containing an aromatic or alkyl aromatic compound and using a high degree of mixing, followed by the electrolytic regeneration of the reduced cerium ion in a cell under near turbulent or turbulent flow conditions at high solution velocities relative to the anode. The preferred cell structure for accomplishing the electrolysis utilizes an turbulence promoting anode arrangement which allows for the anolyte to flow past the anode under the conditions mentioned, and a reduced area cathode whereby the anode and cathode compartments need not be separated by an ion exchange membrane.Type: GrantFiled: February 17, 1995Date of Patent: May 14, 1996Inventor: Stephen Harrison
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Patent number: 5507922Abstract: Benzaldehyde dialkyl acetals of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, R.sup.2 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, cyano or carboxyalkyl where the alkyl group is of 1 to 6 carbon atoms, n is an integer of from 1 to 3 and the radicals R.sup.2 may be identical or different when n is >1, are prepared by electrochemical oxidation of a substituted toluene compound of the general formula II ##STR2## by a process in which a substituted toluene compound II is oxidized in the presence of an alkanol R.sup.Type: GrantFiled: August 11, 1994Date of Patent: April 16, 1996Assignee: BASF AktiengesellschaftInventors: Dieter Hermeling, Heinz Hannebaum, Hartwig Voss, Andreas Weiper-Idelmann