Two Phenols Bonded Directly To Each Other Patents (Class 568/730)
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Patent number: 10196334Abstract: The present invention relates to a process for the preparation of 2,6-di-tert-butyl phenol by reacting phenol with isobutylene in presence of an aluminum phenoxide catalyst, comprising i) preparing an aluminum phenoxide catalyst and phenol comprising mixture a) by mix-ing aluminum metal with phenol, and activating the catalyst by heating the mixture to a temperature of 100 to 180° C., and ii) carrying out a reaction b) by reacting mixture a) with an isobutylene comprising stream comprising 20 to 90% by weight of isobutylene and 10 to 80% by weight of 1-butene and/or 2-butene, which reaction is carried out under pressure and the maximum pressure is 5 to 20 bar.Type: GrantFiled: September 7, 2016Date of Patent: February 5, 2019Assignee: BASF SEInventors: Kai-Uwe Schoening, Walid A. Al-Akhdar, Tiziano Nocentini, Gerard Vilain
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Patent number: 10106497Abstract: The present invention relates to a method for coupling two arenes with selenium dioxide to give a selenobiaryl ether. The method of the present invention includes: adding a first arene to the reaction mixture, adding a second arene to the reaction mixture, adding selenium dioxide to the reaction mixture, adding an acid having a pKa in the range from 0 to 5 to the reaction mixture, and adjusting the reaction temperature of the reaction mixture such that the first arene and the second arene are converted to a selenobiaryl ether. The present invention also relates to novel selenobiaryl ethers.Type: GrantFiled: May 18, 2016Date of Patent: October 23, 2018Assignee: EVONIK DEGUSSA GMBHInventors: Katrin Marie Dyballa, Robert Franke, Siegfried R Waldvogel, Thomas Quell, Michael Mirion
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Patent number: 9045397Abstract: Described herein are high yield methods for making magnolol analogs which are 5,5?-dialkyl-bi-phenyl-2,2?-diols.Type: GrantFiled: December 20, 2011Date of Patent: June 2, 2015Assignee: Colgate-Palmolive CompanyInventors: Ramesh Naik, Sanju Walikar, Govindarajalu Jeyaraman, Koottungalmadhom Ramaswamy Ranganathan
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Patent number: 9000231Abstract: Described herein are high yield methods for making magnolol (5,5?-diallyl-biphenyl-2,2?-diol) and tetrahydro-magnolol (5,5?-dipropyl-biphenyl-2,2?-diol).Type: GrantFiled: June 20, 2011Date of Patent: April 7, 2015Assignee: Colgate-Palmolive CompanyInventors: Ramesh Naik, Sanju Walikar, Ramesh Jayaramaiah, Vangumalla Devaki Devi, Govindarajalu Jeyaraman, Koottungalmadhom Ramaswamy Ranganathan
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Publication number: 20150030683Abstract: In certain embodiments the methods of preventing or delaying the onset of a pre-Alzheimer's condition and/or cognitive dysfunction, and/or ameliorating one or more symptoms of a pre-Alzheimer's cognitive dysfunction, and/or preventing or delaying the progression of a pre-Alzheimer's condition or cognitive dysfunction to Alzheimer's disease, and/or of promoting the processing of amyloid precursor protein (APP) by the non-amyloidogenic pathway are provided. In certain embodiments the methods involve administering, or causing to be administered, to a subject in need thereof certain formulations comprising or more active agent(s) selected from the group consisting of tropisetron disulfiram, honokiol, nimetazepam, and/or derivatives or analogs thereof.Type: ApplicationFiled: February 15, 2013Publication date: January 29, 2015Inventors: Varghese John, Dale E. Bredesen, Stelios Tzannis
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Publication number: 20140357902Abstract: Described herein are high yield methods for making magnolol (5,5?-diallyl-biphenyl-2,2?-diol) and tetrahydro-magnolol (5,5?-dipropyl-biphenyl-2,2?-diol).Type: ApplicationFiled: June 20, 2011Publication date: December 4, 2014Applicant: COLGATE-PALMOLIVE COMPANYInventors: Ramesh Naik, Sanju Walikar, Ramesh Jayaramaiah, Vangumalla Devaki Devi, Govindarajalu Jeyaraman, Koottungalmadhom Ramaswamy Ranganathan
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Publication number: 20140343328Abstract: Described herein are high yield methods for making magnolol analogs which are 5,5?-dialkyl-bi-phenyl-2,2?-diols.Type: ApplicationFiled: December 20, 2011Publication date: November 20, 2014Applicant: Colgate-Palmolive CompanyInventors: Ramesh Naik, Sanju Walikar, Govindarajalu Jeyaraman, Koottungalmadhom Ramaswamy Ranganathan
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Publication number: 20140316098Abstract: In a process for producing phenol, a composition comprising an alkylaromatic compound is contacted with an oxygen-containing stream in the presence of an oxidation catalyst comprising a cyclic imide under oxidation conditions effective to oxidize 15 wt % or less of the alkylaromatic compound based upon the total weight of the composition and produce an oxidation product comprising unreacted alkylaromatic compound and alkylaromatic hydroperoxide in a molar ratio of 6:1 to 100:1. Thereafter, at least a portion of the oxidation product is contacted with an acidic molecular sieve catalyst under cleavage conditions effective to convert at least a portion of the alkylaromatic hydroperoxide into phenol and cyclohexanone.Type: ApplicationFiled: December 15, 2011Publication date: October 23, 2014Applicant: ExxonMobil chemical Patents Inc.Inventors: Kun Wang, Roberto Garcia, Jihad M. Dakka, Gabor Kiss
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Publication number: 20140100342Abstract: Disclosed in the present invention are a fluorine-containing polymerizable compound of the general formula (1) and a polymer compound obtained therefrom: where A represents a single bond, an oxygen atom, a sulfur atom, SO2, CH2, CO, C(CH3)2, C(CH3)(CH2CH3), C(CF3)2, C(CH3)(C6H5), CH2—C6H4—CH2 or a divalent organic group obtained by elimination of two hydrogen atoms from benzene, biphenyl, naphthalene, cyclohexene or fluorene; and a and b each independently represent an integer of 0 to 2 and satisfy a relationship of 1?a+b?4. The thus-obtained polymer compound combines adequate hydrophilicity and high transparency with low water adsorption of fluorine-containing compound.Type: ApplicationFiled: May 29, 2012Publication date: April 10, 2014Applicant: Central Glass Company, LimitedInventors: Junya Nakatsuji, Makoto Matsuura, Kazuhiro Yamanaka
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Publication number: 20130303788Abstract: A method of producing honokiol and analogues thereof, and novel intermediates prepared by virtue thereof are disclosed herein. A pharmaceutical composition for treating Parkinson's disease, which contains honokiol and/or the analogues thereof, is also disclosed herein.Type: ApplicationFiled: September 14, 2012Publication date: November 14, 2013Applicant: Tzu Chi UniversityInventors: Ming-Huan Chan, Chinpiao Chen, Hwei-Hsien Chen
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Publication number: 20130280185Abstract: Described herein are compounds of Formula (I): or a salt thereof; wherein: R1 and R5 are independently selected from H, OH and alkoxy; R2-R4 and R6-R8 are independently selected from H, OH, F, Cl, Br, and I; R9 and R10 are independently selected from H, alkyl, alkenyl, alkynyl, and aryl; with the proviso that: at least one of R land R5 is OH or alkoxy; and at least one of CR2-R4 and R6-R8 is F, Cl, Br or I; compositions comprising said compounds; and methods of making and using the same.Type: ApplicationFiled: December 21, 2010Publication date: October 24, 2013Applicant: COLGATE-PALMOLIVE COMPANYInventors: Ravi Subramanyam, Guofeng Xu, Jennifer Gronlund, Shamim Ansari
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Patent number: 8519197Abstract: A method is described for producing magnolol, or a derivative or analogue thereof. The method includes obtaining MOM ether of 5,5?-diallylbiphenyl-2,2?-diol or a derivative or analogue thereof and subsequently converting the MOM ether of 5,5?-diallylbiphenyl-2,2?-diol into magnolol or a derivative or analogue thereof.Type: GrantFiled: February 25, 2010Date of Patent: August 27, 2013Assignees: Colgate-Palmolive Company, Indian Institute of Chemical TechnologyInventors: Basi V. Subba Reddy, Jhillu S. Yadav, Ravi Subramanyam
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Publication number: 20120269745Abstract: A hydroxytyrosol polymer formed by either C—C coupling or C—O—C coupling is provided. Preferred polymers are formed by C—C coupling and the dimer has the following structure: (Formula I) (I) Compounds of the invention have been found to have antioxidant properties and their use in antioxidant compositions forms a further aspect of the invention.Type: ApplicationFiled: September 22, 2010Publication date: October 25, 2012Applicant: University of Cape TownInventors: Stephanie Gail Burton, Lester Merlin Davids
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Patent number: 8283501Abstract: Disclosed herein are optically active biphenol derivatives represented by the following formulas (1) and (2), a method for optically resolving a biphenol derivative represented by formula (2?), a production method of an optically active biphenol derivative (1) comprising a step for reacting a Brønsted acid with a biphenol derivative (2), and a production method of an optically active biphenol derivative (3) comprising a step for reacting a Lewis acid with an optically active biphenol derivative (1) or an optically active biphenol derivative (2).Type: GrantFiled: January 6, 2009Date of Patent: October 9, 2012Assignee: Nippon Soda Co., Ltd.Inventors: Yoshikazu Ito, Yasushi Kubota, Tsutomu Inoue
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Publication number: 20120215003Abstract: The present invention relates to process for the resolution of omeprazole. The present invention further provides a novel compound of enantiomers of omeprazole cyclic amine salt and a process for preparing it. The present invention also provides a solid of (R)- or (S)-omeprazole cyclic amine salt and a process for preparing it. The present invention also provides a process for the preparation of esomeprazole magnesium dihydrate substantially free of its trihydrate form. The present invention also provides a process for the preparation of recovery of chiral BINOL.Type: ApplicationFiled: November 12, 2009Publication date: August 23, 2012Applicant: HETERO RESEARCH FOUNDATIONInventors: Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Rapolu Raji Reddy, Dasari Muralidhara Reddy, Bandi Vamsi Krishna, Voggu Ramesh Reddy
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Patent number: 8168833Abstract: Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.Type: GrantFiled: December 3, 2009Date of Patent: May 1, 2012Assignee: Queen's University at KingstonInventors: Yigang Zhao, Victor A. Snieckus
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Publication number: 20120052026Abstract: Antiplaque oral compositions are provided that contain an orally acceptable carrier and an antibacterial effective amount of the compound of formula (I). In various embodiments, the compositions contain from about 0.001% to about 10% by weight of the compound of formula (I).Type: ApplicationFiled: November 9, 2011Publication date: March 1, 2012Applicant: COLGATE-PALMOLIVE COMPANYInventors: Ravi Subramanyam, Prem Sreenivasan
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Patent number: 7838618Abstract: A process for producing a phenylene ether oligomer comprising oxidative polymerization of a specific bivalent phenol compound and a specific monovalent phenol compound in an aromatic hydrocarbon solvent, wherein the aromatic hydrocarbon solvent of a phenylene ether oligomer solution obtained after the termination of the polymerization is replaced with a water-soluble organic solvent having a boiling point higher than that of the aromatic hydrocarbon solvent and the resultant phenylene ether oligomer solution is brought into contact with water, thereby precipitating the phenylene ether oligomer as particles.Type: GrantFiled: May 24, 2007Date of Patent: November 23, 2010Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kiyonari Hiramatsu, Yoshio Mukai, Hidemi Hirashima, Yuji Takeda
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Publication number: 20100280284Abstract: An optically active 2,2?-biphenol derivative and a production method that enables simple and efficient production of this compound. More specifically, an optically active biphenol derivative represented by the following formulas (1) and (2), a method for optically resolving a biphenol derivative represented by formula (2?), a production method of an optically active biphenol derivative (1) comprising a step for reacting a Brønsted acid with a biphenol derivative (2), and a production method of an optically active biphenol derivative (3) comprising a step for reacting a Lewis acid with an optically active biphenol derivative (1) or an optically active biphenol derivative (2). In the following formulas, R represents, for example, a primary or secondary alkyl group having 1 to 10 carbon atoms, * represents an axially asymmetric center, X represents a halogen atom, and R2 represents a tertiary alkyl group having 4 to 6 carbon atoms.Type: ApplicationFiled: January 6, 2009Publication date: November 4, 2010Applicant: Nippon Soda Co., Ltd.Inventors: Yoshikazu Ito, Yasushi Kubota, Tsutomu Inoue
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Publication number: 20100267781Abstract: Methods of using apogossypol and its derivatives for treating inflammation is disclosed. Also, there is described a group of compounds having structure A, or a pharmaceutically acceptable salt, hydrate, N-oxide, or solvate thereof are provided: wherein each R is independently H, C(O)X, C(O)NHX, NH(CO)X, SO2NHX, or NHSO2X, wherein X is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocycle, or substituted heterocycle. Compounds of group A may be used for treating various diseases or disorders, such as cancer.Type: ApplicationFiled: April 14, 2010Publication date: October 21, 2010Applicant: Burnham Institute for Medical ResearchInventor: Maurizio Pellechia
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Publication number: 20100256396Abstract: An aromatic compound of the following formula (1), (2), (5) or (6), wherein, Ar1 and Ar3 represent a tetra-valent aromatic hydrocarbon group or a tetra-valent heterocyclic group, and Ar2, Ar4, Ar5, Ar6 and Ar7 represent a tri-valent aromatic hydrocarbon group or a tri-valent heterocyclic group, A1 represents —Z1—, —Z2—Z3— or —Z4?Z5—, wherein Z1, Z2 and Z3 represent O, S or the like and Z4 and Z5 represent N, B, P or the like, X1, X2, X3, X4, X9, X10, X11, and X12 represent a halogen atom or the like.Type: ApplicationFiled: June 15, 2010Publication date: October 7, 2010Applicant: Sumitomo Chemical Company, LimitedInventors: Satoshi KOBAYASHI, Satoshi MIKAMI
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Publication number: 20100184978Abstract: A bipyridine compound represented by the formula (1): wherein R1, R2 and R3 each independently represent a C1-C10 alkyl group which may be substituted etc., and R4, R5, R6, R7 and R8 each independently represent a hydrogen atom etc., a transition metal complex obtained by contacting a bipyridine compound represented by the formula (1) with a compound of a transition metal belonging to Group 9, 10 or 11, and a method for production of a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of the transition metal complex.Type: ApplicationFiled: June 18, 2008Publication date: July 22, 2010Inventors: Taku Asaumi, Takashi Kamikawa
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Patent number: 7737310Abstract: A process for preparing biphenols of the general formula I by reaction of monophenols of the general formula II where the radicals R1, R2 and R3 are each, independently of one another, hydrogen, alkyl, aryl or arylalkyl having from 1 to 10 carbon atoms, in the presence of an oxidant in a reactor, wherein a) the reactor comprises no stationary internals which act as baffles, b) a total of not more than 0.6 mol of oxidant is used per one mol of monophenol, and c) the oxidant is introduced either continuously or discontinuously in a plurality of portions over a period of from 10 minutes to 24 hours, with the amount of oxidant introduced per unit time not being constant over the total period of time but instead being varied.Type: GrantFiled: April 5, 2006Date of Patent: June 15, 2010Assignee: BASF SEInventors: Michael Bartsch, Gerd Haderlein, Tobias Aechtner, Jens Scheidel, Christian Dienes, Alexander Tempel, Thorsten Hofrichter, Werner Weinle
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Publication number: 20100099922Abstract: The invention relates to the preparation of alkylated phenols. More specifically, the invention relates to an improved process for the manufacture of 2-secondary-alkyl-4,5-di-normal-alkylphenols.Type: ApplicationFiled: October 12, 2009Publication date: April 22, 2010Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventors: JOACHIM C. RITTER, James Michael Garner
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Patent number: 7608741Abstract: The present invention related to method for the mass separation of magnolol from Magnoliae cortex or Magnoliae radix. The method comprises the steps of: 1) crushing Magnoliae cortex or Magnoliae radix, extracting the crushed material with organic solvent, adding n-hexane to the extract so as to obtain a n-hexane layer; 2) concentrating the n-hexane layer in a water bath at a temperature of 30-40° C. and a revolution speed of 40-200 RPM under reduced pressure so as to form a crude crystal; and 3) removing the n-hexane from the crude crystal, completely dissolving the crude crystal in chloroform, adding n-hexane to the n-hexane-containing solution, and leaving the solution to stand at room temperature so as to recrystallize the solution. In the method, a column chromatography step which is necessarily carried out in the general separation process is omitted so that separation process steps are reduced, leading to a saving in separation time.Type: GrantFiled: June 21, 2005Date of Patent: October 27, 2009Assignee: Korea Institute of Oriental MedicineInventors: Jin Sook Kim, Yun Mi Lee, Dae Sik Jang
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Publication number: 20080280994Abstract: The invention provides extracts of brown seaweed of the genus Ascophyllum that have valuable pharmacological properties. In particular, compositions of the invention are useful for e.g.: inhibiting alpha-glucosidase activity; preventing or treating conditions mediated by alpha-glucosidase activity; reducing blood glucose levels; preventing or treating diabetes; modulating glucose uptake in adipocytes; preventing or treating obesity; scavenging free radicals; stimulating the immune system; activating macrophages; preventing or treating condition mediated by macrophage activation; and modulating nitric oxide production by macrophages. Methods for using the Ascophyllum extracts of the invention are provided, as are kits comprising Ascophyllum extracts of the invention and instructions for using the extracts.Type: ApplicationFiled: August 15, 2005Publication date: November 13, 2008Inventors: Junzeng Zhang, Harry Stephen Ewart, Jing Kai Shen, Colin James Barrow
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Publication number: 20080262011Abstract: The present invention relates to a compound of formula I, or a pharmaceutically acceptable salt thereof. Formula (I), wherein R1 and R2 are each independently H or alkyl; Y is an alkyl group. CONR3R4, COOR5SO2NR16R17, NHSO2R18 or CN; X is an aryl or heteroaryl group, each of which may be optionally substituted with one or more substituents selected from (CH2)mZ where Z is halogen, OH, CN, alkyl, alkoxy, NO2, CF3, CONR6R7, CN, NR8R9, COOR10 or NHCOR11 and m is 0 to 3; R3 to R11 are each independently H, alkyl or aryl, wherein said alkyl and aryl groups are optionally substituted by one or more substituents selected from halogen, OH, CN, alkyl, alkoxy, NO2, CF3, CONR12R13, CN, NH2, COOR14, NHCOR15, and CN; R12 to R18 are each independently H or alkyl, more preferably H or Me; n is 1 to 6; wherein the compound is other than 3?,5?-dimethyl-4-(1,1-dimethylheptyl)-1,1?-biphenyl-2-ol.Type: ApplicationFiled: December 21, 2005Publication date: October 23, 2008Inventors: David Selwood, Cristina Visintin, David Baker, Gareth Pryce, Masahiro Okuyama
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Publication number: 20080188693Abstract: The present invention related to method for the mass separation of magnolol from Magnoliae cortex or Magnoliae radix. The method comprises the steps of: 1) crushing Magnoliae cortex or Magnoliae radix, extracting the crushed material with organic solvent, adding n-hexane to the extract so as to obtain a n-hexane layer; 2) concentrating the n-hexane layer in a water bath at a temperature of 30-40 ° C. and a revolution speed of 40-200 RPM under reduced pressure so as to form a crude crystal; and 3) removing the n-hexane from the crude crystal, completely dissolving the crude crystal in chloroform, adding n-hexane to the n-hexane-containing solution, and leaving the solution to stand at room temperature so as to recrystallize the solution. In the method, a column chromatography step which is necessarily carried out in the general separation process is omitted so that separation process steps are reduced, leading to a saving in separation time.Type: ApplicationFiled: June 21, 2005Publication date: August 7, 2008Applicant: Korea Institute of Oriental MedicineInventors: Jin Sook Kim, Yun Mi Lee, Dae Sik Jang
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Patent number: 7002046Abstract: A method for preparing and isolating dihydroxybiaryl compounds, such as 4,4?-dihydroxybiphenyl, is disclosed. The alkali metal salt of the dihydroxybiaryl compound is protonated with the monohydroxyaryl halide compound initially used in the reductive coupling reaction which produced the alkali metal salt. In addition, the alkali metal salt of the monohydroxyaryl halide compound is produced by the process, which can then be recycled as the base and monohydroxyaryl halide in a further reductive coupling reaction to form the alkali metal salt of the dihydroxybiaryl compound.Type: GrantFiled: October 7, 2003Date of Patent: February 21, 2006Assignee: General Electric CompanyInventors: John Yaw Ofori, Ben Purushotam Patel, Eric James Pressman
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Patent number: 6891072Abstract: The present invention provides a method for preparing dimer of a monohydroxy aromatic compound. In the method of the present invention, oxidative coupling reaction of a monohydroxy aromatic compound represented by formula [I]: Ar—OH??[I] wherein Ar represents an optionally substituted aromatic group is carried out in a nitrogen containing polar solvent in the presence of a copper salt. By the method of the instant invention, dimer of the monohydroxy aromatic compound can be obtained in high yield.Type: GrantFiled: April 18, 2002Date of Patent: May 10, 2005Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Masaya Kitayama, Kenji Minami, Hiroyuki Wakamori, Hikari Hirai
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Patent number: 6844462Abstract: The invention relates to the biphenyldiols of the formula (V) The corresponding racemic and enantiomerically pure triflate compounds thereof, where R1 and R2 are H, R3 is chlorine, and R4 is methoxy. In an alternate embodiment, R1 and R2 are hydrogen and R3 and R4 are C1-C4-alkoxy, fluorine, or chlorine.Type: GrantFiled: April 7, 2003Date of Patent: January 18, 2005Assignee: Bayer AktiengesellschaftInventors: Birgit Drieben-Hölscher, Joachim Kralik, Inga Ritzkopf, Christian Steffens, Guido Giffels, Claus Dreisbach, Thomas Prinz
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Patent number: 6835859Abstract: A method for continuously producing 3,3′,5,5′-tetra-t-butyl-4,4′-biphenol by oxidizing/dimerizing 2,6-di-t-butylphenol, comprising the steps of: supplying 2,6-di-t-butylphenol to a first reaction section of a reaction apparatus in which at least the first reaction section and a second reaction section are connected in series; supplying alkali catalyst to at least said first reaction section; and distributing oxygen containing gas to each reaction section respectively; whereby a reaction mixture containing 3,3′,5,5′-tetra-t-butyl-4,4′-biphenol is obtained from a last reaction section.Type: GrantFiled: October 14, 2003Date of Patent: December 28, 2004Assignee: Honshu Chemical Industry Co., Ltd.Inventor: Mikio Kawahara
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Patent number: 6833482Abstract: Disclosed is a method for preparing a bis(hydroxy-aromatic) compound which comprises the steps of: contacting at least one halo-substituted hydroxy-aromatic compound in a solvent mixture comprising water and at least one organic solvent in the presence of at least one base, at least one catalyst comprising palladium and hydrogen gas at a pressure in a range of between atmospheric pressure and 350 Kilopascals.Type: GrantFiled: October 7, 2003Date of Patent: December 21, 2004Assignee: General Electric CompanyInventors: Ben Purushotam Patel, Eric James Pressman, Ryan Christopher Mills
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Patent number: 6794548Abstract: A method for producing 4,4′-biphenol, comprising the steps of: preparing serially arranged reaction bathes for two or more steps; and carrying out a debutylation reaction of 3,3′,5,5′-tetra-t-butyl-4,4′-biphenol sequentially in the presence of an acid catalyst in a reaction solvent by supplying at least one kind of phenols selected from the group consisting of phenol, monoalkylphenols, dialkylphenols, and trialkylphenols, in a proportion of at least 0.5 mole part relative to one mole part of 3,3′,5,5′-tetra-t-butyl-4,4′-biphenol, to each reaction bath as a solvent for addition, wherein the number of carbon atoms of alkyl groups in alkylphenols consisting of the monoalkylphenols, dialkylphenols, and trialkylphenols, is each independently in the range of 1 to 4, and wherein a solvent for addition to a reaction bath for the latter step has a smaller average number of alkyl groups than a solvent for addition to a reaction bath for the former step.Type: GrantFiled: October 14, 2003Date of Patent: September 21, 2004Assignee: Honschu Chemical Industry Co., Ltd.Inventors: Mikio Kawahara, Toyokazu Kitaura
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Publication number: 20040122263Abstract: A method for continuously producing 3,3′,5,5′-tetra-t-butyl-4,4′-biphenol by oxidizing/dimerizing 2,6-di-t-butylphenol, comprising the steps of: supplying 2,6-di-t-butylphenol to a first reaction section of a reaction apparatus in which at least the first reaction section and a second reaction section are connected in series; supplying alkali catalyst to at least said first reaction section; and distributing oxygen containing gas to each reaction section respectively; whereby a reaction mixture containing 3,3′,5,5′-tetra-t-butyl-4,4′-biphenol is obtained from a last reaction section.Type: ApplicationFiled: October 14, 2003Publication date: June 24, 2004Inventor: Mikio Kawahara
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Publication number: 20040049087Abstract: A process for making a compound of the formula I 1Type: ApplicationFiled: February 14, 2003Publication date: March 11, 2004Inventor: Rafael Shapiro
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Patent number: 6689921Abstract: A method for producing biphenols by oxidative coupling of dialkylphenols which proceeds in two stages using a copper amine complex which is catalytically effective in each stage is disclosed. A novel copper amine complex is also disclosed wherein the complex exhibits high catalytic activity for the oxidative coupling of substituted phenols under mild conditions, has dual (two stage) activity and can be readily recycled and reused.Type: GrantFiled: August 26, 2002Date of Patent: February 10, 2004Assignee: Wiley Organics, Inc.Inventor: Gregory Kaplan
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Patent number: 6689920Abstract: A process for producing 2,2′,3,3′,5,5′-hexamethyl-[1,1′-biphenyl]-4,4′-diol, which process comprises, while setting a pH of a reaction liquid containing an alkaline aqueous solution, a surfactant, a copper catalyst and 2,3,6-trimethylphenol during a reaction in the range of from 8 to 14 and controlling the variation range of the pH of the reaction liquid within ±1, oxidatively coupling the 2,3,6-trimethylphenol with an oxygen-containing gas, and a process for producing a bifunctional phenylene ether oligomer compound having a controlled average molecular weight, comprising carrying out oxidation polymerization under a proper oxygen concentration.Type: GrantFiled: October 16, 2002Date of Patent: February 10, 2004Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kenji Ishii, Kiyonari Hiramatsu, Makoto Miyamoto, Yasumasa Norisue, Katsuhiko Yanagida
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Publication number: 20030229256Abstract: A process for producing 2,2′,3,3′,5,5′-hexamethyl-[1,1′-biphenyl]-4,4′-diol, which process comprises,Type: ApplicationFiled: October 16, 2002Publication date: December 11, 2003Inventors: Kenji Ishii, Kiyonari Hiramatsu, Makoto Miyamoto, Yasumasa Norisue, Katsuhiko Yanagida
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Patent number: 6555718Abstract: A process for making a compound of the formula IType: GrantFiled: September 5, 2002Date of Patent: April 29, 2003Assignee: E. I. du Pont de Nemours and CompanyInventor: Rafael Shapiro
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Patent number: 6512149Abstract: By bringing a p-butylphenol compound or m-butylphenol compound in the gas phase into contact with a solid acid catalyst, i.e., a silica-alumina catalyst or alumina catalyst while heating, butyl groups are removed from the butylphenol compound and at the same time, highly purified isobutylene is recovered.Type: GrantFiled: April 13, 2001Date of Patent: January 28, 2003Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Kazuhiko Yao, Mitsuhiro Higashi, Kenji Ekawa
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Patent number: 6489517Abstract: A process for making a compound of the formula IType: GrantFiled: November 26, 2001Date of Patent: December 3, 2002Assignee: E. I. du Pont de Nemours and CompanyInventor: Rafael Shapiro
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Patent number: 6476277Abstract: The present invention relates to a process for preparing hydroxyaromatics by oxidizing aromatics with dinitrogen monoxide in the gas phase in the presence of nanocrystalline zeolites.Type: GrantFiled: July 24, 2001Date of Patent: November 5, 2002Assignee: Bayer AktiengesellschafterInventors: Bernd Vogel, Elias Klemm, Mathias Seitz, Jochen Heller, Jörg Reiser
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Patent number: 6441248Abstract: This invention relates to a method for producing biphenols by oxidative coupling of dialkylphenols which proceeds in two stages using a copper amine complex which is catalytically effective in each stage.Type: GrantFiled: February 23, 2000Date of Patent: August 27, 2002Assignee: Wiley Organics, Inc.Inventor: Gregory Kaplan
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Patent number: 6433236Abstract: A substituted diaryl compound or a mixture of substituted diaryl compounds, such as dimethylbiaryl compounds are isomerized by treatment with a strong acid or mixtures of strong acids in the absence of any additional catalyst. The strong acid or mixture of acids has a Hammett acidity of less than about −12.6. The isomerization reaction conditions such as reaction temperature, amount of acid, and amount of solvent can be adjusted to selectively produce desired isomers in high yields. One or more desired isomers may be produced in high yields by isomerization of substituted diaryl compounds and selectively removing one or more desired isomers from the resulting equilibrium mixture of isomers. The isomer mixture may be re-isomerized subsequent to selective removal of the desired isomer to produce additional amounts of desired isomer.Type: GrantFiled: March 21, 2000Date of Patent: August 13, 2002Assignee: Arteva North America S.A.R.L.Inventors: David Anthony Schiraldi, Alexei Viktorovich Iretski, Sheldon Christopher Sherman, Laren Malcolm Tolbert, Mark Gilmore White
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Patent number: 6365775Abstract: Compounds of formula (I), wherein [X] represents aromatic carbocyclic rings (A) and (B), where R1, R2, R3, R4, R5, R6 and R7 are as defined in the description, salts thereof, a method and intermediates for preparing same, the use thereof as drugs, and pharmaceutical compositions containing same, are disclosed.Type: GrantFiled: July 27, 2000Date of Patent: April 2, 2002Assignee: Aventis Pharma S.A.Inventor: Dominique Lesuisse
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Patent number: 6147119Abstract: Compounds of formula (I), wherein [X] represents aromatic carbocyclic rings (A) and (B), where R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are as defined in the description, salts thereof, a method and intermediates for preparing same, the use thereof as drugs, and pharmaceutical compositions containing same, are disclosed.Type: GrantFiled: September 28, 1998Date of Patent: November 14, 2000Assignee: Hoechst Marion RousselInventor: Dominique Lesuisse
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Patent number: 6118029Abstract: A batch or continuous process produces highly pure 3,3',5,5'-tetra-t-butylbiphenol suitable as a starting material for the synthesis of 4,4'-biphenol. The process for producing 3,3',5,5'-tetra-t-butylbiphenol comprises conducting an oxidation coupling of purified 2,6-di-t-butylphenol(i) or crude 2,6-di-t-butylbiphenol(ii), said crude 2,6-di-t-butylphenol being obtained by reacting isobutylene with phenol in the presence of an aluminum catalyst, and removing the aluminum catalyst. The 2,6-di-t-butylphenol is oxidatively coupled in an alkali metal catalyst mixture comprising (1) an alkali metal catalyst and alkylphenols, or (2) alkali metal catalyst, alkylphenols and phenol to produce 3,3',5,5'-tetra-t-butylbiphenol. The oxidative coupling is conducted together with 10-30% by weight of phenol and/or t-butylphenol per 100% by weight of 2,6-di-t-butylphenol in the presence of an alkali metal catalyst.Type: GrantFiled: January 30, 1998Date of Patent: September 12, 2000Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Yoichiro Isota, Kazuhiko Yao, Mikio Kawahara
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Patent number: 6077979Abstract: Coupling in aqueous medium of 2,4-dimethylphenol by persulfate anion or hydrogen peroxide in the presence of iron or iron compounds gives good yields of relatively pure 3,3',5,5'-tetramethyl-2,2'-biphenol.Type: GrantFiled: February 18, 1999Date of Patent: June 20, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: Weiming Qiu
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Patent number: 5767327Abstract: A method for oxidizing certain aromatic compounds such as biphenols using an oxidizing agent such as peroxide in a solvent such as a concentrated alkanoic acid or and alkane diol.Type: GrantFiled: October 7, 1996Date of Patent: June 16, 1998Assignee: Wiley Organics, Inc.Inventors: Gregory Kaplan, Alexander R. Pokora