Preparing By Alkylation Of Benzene Ring Patents (Class 568/628)
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Patent number: 11326114Abstract: A method for marking a petroleum hydrocarbon or a liquid biologically derived fuel; said method comprising adding to said petroleum hydrocarbon or liquid biologically derived fuel at least one compound that is a R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10-substituted diaryl ether, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 independently are hydrogen, hydrocarbyl or hydrocarbyloxy; wherein each compound having formula (I) is present at a level from 0.01 ppm to 20 ppm.Type: GrantFiled: March 25, 2019Date of Patent: May 10, 2022Assignees: DOW GLOBAL TECHNOLOGIES LLC, ROHM AND HAAS COMPANYInventors: Robert J. Wright, Brian A. Jazdzewski, Warren E. Smith, Jeremy Chris Reyes, Zahid Asif, Clark H. Cummins, William L. Winniford
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Patent number: 11186734Abstract: An epoxy resin emulsion includes a continuous phase including an aqueous carrier and an acid. The emulsion also includes a dispersed phase including an epoxy resin. The epoxy resin is the reaction product of an amine compound and a first epoxy reactant. The first epoxy reactant itself includes the reaction product of (1) an aromatic diol monomer, (2) a di-glycidyl ether of Bisphenol A and/or a di-glycidyl ether of catechol, and (3) a C8-C18 alkyl phenolic end-capping agent. The (1) aromatic diol monomer has the structure: In this structure, each of R1-R4 is independently a hydrogen atom, a C1-C8 alkyl group, a C3-C8 cycloalkyl group, an aryl group, an aralkyl group, a halide group, a cyano group, a nitro group, a blocked isocyanate group, or a C1-C8 alkyloxy group or wherein any two or more of R1-R4 may be a fused ring.Type: GrantFiled: May 31, 2019Date of Patent: November 30, 2021Assignee: AXALTA COATING SYSTEMS IP CO., LLCInventors: Xin Jin, Chun Ren
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Publication number: 20140206908Abstract: PAH is subjected to C—H/C—B coupling using a specific boron compound, a palladium compound, and o-chloranil to produce a compound in which a C—H bond of the PAH is directly arylated regioselectively in a simple manner. When the substrate and the boron compound are appropriately selected, a larger PAH can also be obtained by further performing an annulation reaction after the coupling reaction. Similarly, when PAH is subjected to C—H/C—H cross-coupling using a specific aromatic compound, a palladium compound, and o-chloranil, a compound in which a C—H bond of the PAH is directly arylated regioselectively can be produced in a simple manner. When the substrate and the aromatic compound are appropriately selected in this case, a larger PAH can also be obtained by further performing an annulation reaction after the cross-coupling reaction.Type: ApplicationFiled: June 8, 2012Publication date: July 24, 2014Applicant: NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITYInventors: Kenichiro Itami, Kenji Mochida, Katsuaki Kawasumi, Yasutomo Segawa, Tomonori Kajino
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Publication number: 20130317223Abstract: A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1—B-T??(I); where R1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.Type: ApplicationFiled: November 6, 2012Publication date: November 28, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, David M. Knapp, Eric P. Gillis
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Publication number: 20130281700Abstract: The invention relates to palladium(0)-tris{tri-[3,5-bis(trifluoromethyl)-phenyl]-phosphine} complex of formula (I), as well as to its preparation and use. This compound is outstandingly stable, and can be used as catalyst with excellent results.Type: ApplicationFiled: June 14, 2013Publication date: October 24, 2013Applicants: CHINOIN GYOGYSZER-ES VEGYESZETI TER-MEKEK GYARA ZRT, H4SEP KFTInventors: Zoltán DALICZEK, Tibor SOÓS, Zoltán FINTA, Géza Timári, Gábor Vlád
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Publication number: 20130225815Abstract: A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.Type: ApplicationFiled: February 19, 2013Publication date: August 29, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
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Publication number: 20130184485Abstract: What is described is a process for preparing organic compounds of the general formula (I) R—R???(I) by converting a corresponding compound of the general formula (II) R—X ??(II) in which X is fluorine, chlorine, bromine or iodine to an organomagnesium compound of the general formula (III) [M+]n[RmMgXkY1]??(III) wherein compounds of the formula (III) are reacted with a compound of the general formula (IV) characterized in that the reaction of (III) with (IV) is performed in the presence of a) catalytic amounts of an iron compound, based on the compound of the general formula (II), and optionally in the presence of b) a nitrogen-, oxygen- and/or phosphorus-containing additive in a catalytic or stoichiometric amount, based on the compound of the general formula (II).Type: ApplicationFiled: February 1, 2011Publication date: July 18, 2013Applicant: SALTIGO GMBHInventors: Matthias Gotta, Bernd Wilhelm Lehnemann, Waldemar Maximilian Czaplik, Matthias Mayer, Axel Jacobi Von Wangelin
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Publication number: 20130150607Abstract: This invention is directed to a new process for making an alkylaromatic compound. In an embodiment of this invention, the process is directed to selective synthesizing an alkylaromatic compound comprising a high amount of dialkylate product. In general, this process involves contacting at least one alkylatable aromatic compound with an alkylating agent and a catalyst under suitable reaction conditions such that the resulting reactor effluent prior to any stripping step may be characterized by a dialkylate product content of at least 44 wt % and a trialkylate and higher polyalkylate product content of no more than 20 wt %. The alkylaromatic compounds produced have excellent thermal and oxidative stabilities, good additive solvency, and improved seal compatibility while maintaining good VI and low temperature properties. They are useful as lubricant basestocks and lubricant additives.Type: ApplicationFiled: December 7, 2011Publication date: June 13, 2013Inventor: Beth A. WINSETT
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Publication number: 20130150608Abstract: This invention is directed to an improvement in the process for the production of alkylaromatic compounds that results in lower levels of residual unreacted materials in the final product. This invention comprises: 1) alkylation of an aromatic compound with an alkylating agent and a catalyst to produce an effluent stream comprising an alkylaromatic compound and unreacted materials; 2) heating the effluent stream; 3) stripping the effluent stream in a stripping device in the presence of steam; 4) separating a stripping stream from the stripping device, the stripping stream rich in unreacted materials; and 5) separating a product stream from the stripping device, the product stream rich in alkylated aromatic compound.Type: ApplicationFiled: December 13, 2011Publication date: June 13, 2013Inventors: Beth A. Winsett, James I. Arnett, II, Kenwyn M. Leger, Brady A. Compton
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Publication number: 20130053566Abstract: Cationic palladium catalysts comprising diamino carbene ligands, wherein the catalysts are of the formula [Pd(X)q(LBX)t(DC)]r+[Ym-]p or [Pd(X)q(LB)n(LBX)t(DC)]2a+[V?]u[Z2?]y, wherein DC is a diamino carbene ligand, X is an anionic ligand, LBX is a combined anionic and neutral ligand, and Y, V, and Z are non-coordinating anions. The compounds are useful in catalytic reactions, including cross-coupling reactions and hydroamination reactions. In particular, the catalysts are used in the following reactions: Suzuki-Miyaura coupling, Kumada coupling, Negishi coupling, Sonogashira coupling, Hartwig-Buchwald amination, and Heck-Mizoroki coupling.Type: ApplicationFiled: April 14, 2011Publication date: February 28, 2013Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Chi-Wing Tsang, Wenli Jia
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Publication number: 20120316340Abstract: The use of metal-accumulating plants for implementing chemical reactions.Type: ApplicationFiled: November 18, 2010Publication date: December 13, 2012Applicants: UNIVERSITE MONTPELLIER 2 SCIENCES ET TECHNIQUES, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Claude Grison, Jose Escarre
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Patent number: 8293947Abstract: The present invention concerns a method for the preparation of therapeutically valuable triphenylbutene derivatives, especially ospemifene or fispemifene.Type: GrantFiled: September 16, 2010Date of Patent: October 23, 2012Assignee: Hormos Medical Ltd.Inventors: Marja Sodervall, Maire Eloranta, Arja Kalapudas
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Publication number: 20120095250Abstract: A solid catalyst, such as a molecular sieve catalyst or solid acid catalyst, is supported by a binder, such as amorphous silica or alumina, wherein the binder is charged with metal ions to form an ion-modified binder. The ion-modified binder is capable of attachment to polar contaminants and inhibit their contact with the catalyst. The catalyst can be a zeolite and can be the catalyst for an alkylation reaction, such as the alkylation of benzene with ethylene.Type: ApplicationFiled: December 22, 2011Publication date: April 19, 2012Applicant: FINA TECHNOLOGY, INC.Inventors: Joseph E. Pelati, Taylor Rives
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Patent number: 8153801Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.Type: GrantFiled: September 11, 2008Date of Patent: April 10, 2012Assignee: Gilead Sciences, Inc.Inventors: Eric Dowdy, Steven Pfeiffer
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Publication number: 20120046471Abstract: This invention relates to a process for preparing functionalized aryl, heteroaryl, cycloalkenyl, or alkenyl compounds, by a transition-metal-catalyzed cross-coupling reaction of a substituted or unsubstituted aryl-X, heteroaryl-X, cycloalkenyl-X or alkenyl-X compound with an alkyl, alkenyl, cycloalkyl or cycloalkenyl halide, where X is a halide, diazonium, tosylate (p-toluenesulphonate), mesylate (methanesulphonate) or triflate (trifluoromethanesulphonate) leaving group.Type: ApplicationFiled: September 14, 2011Publication date: February 23, 2012Applicant: SALTIGO GMBHInventors: Mark Sundermeier, Matthias Gotta, Axel Jacobi von Wangelin, Waldermar Maximilian Czaplik
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Publication number: 20100292480Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.Type: ApplicationFiled: September 11, 2008Publication date: November 18, 2010Applicant: Gilead Sciences, IncInventors: Eric Dowdy, Steven Pfeiffer
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Publication number: 20100160683Abstract: There is provided a novel process for production of a 2-(substituted phenyl)-3,3,3-trifluoropropene. Disclosed is a process for production of a 2-(substituted phenyl)-3,3,3-trifluoropropene compound represented by the formula (7) or a salt thereof The process comprises reacting a compound represented by the formula (1) (X is an alkyl group, etc.) with a compound represented by the formula (2) (Y is a halogen atom, etc.Type: ApplicationFiled: February 13, 2007Publication date: June 24, 2010Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.Inventors: Kazutaka Matoba, Takashi Mizukoshi, Yuji Moriyama
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Patent number: 7235699Abstract: The present invention relates to alkoxy-substituted indanes, their preparation and use and to the preparation and use of the corresponding alkoxy-substituted indanones.Type: GrantFiled: February 27, 2003Date of Patent: June 26, 2007Assignee: Symrise GmbH & Co. KGInventor: Oskar Koch
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Patent number: 6794547Abstract: The invention relates to a process for the synthesis of aryl alkyl monoethers by reaction of a phenol compound, comprising one or more hydroxyl groups attached to the aromatic system, and of a dialkyl carbonate. It is a solvent-free process carried out at a pressure of between 0.93×105 Pa and 1.07×105 Pa, at a temperature of between 100° C. and 200° C., and in the presence of a catalyst chosen from the group consisting of alkaline carbonates and alkaline hydroxides. The dialkyl carbonate is added gradually to the reaction mixture.Type: GrantFiled: February 20, 2002Date of Patent: September 21, 2004Assignee: SNPEInventors: Elisabeth Borredon, Antoine Gaset, Samedy Ouk, Sophie Thiebaud-Roux, Pierre Le Gars
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Patent number: 6706930Abstract: There is described a process for the preparation of halogenated hydroxydiphenyl compounds of formula (1) by acylation of a halogenated benzene compound (first stage), etherification of the acylated compound with a halogenated phenol compound, which is not further substituted in the ortho-position (second stage), oxidation of the etherified compound (third stage) and hydrolysis of the oxidized compound in a fourth stage, wherein the reaction of the second stage is carried out in the presence of K2CO3 and any desired copper catalyst, where K2CO3 is used in a concentration of from 0.5 to 30 mol, based on the phenol compound employed of formula (6), according to the reaction scheme (I) in which R1 and R2 independently of one another are F, Cl or Br; R3 and R4 independently of one another are hydrogen; or C1-C4alkyl; m is 1 to 3; and n is 1 or 2. The compounds of formula (1) are used for protecting organic materials and articles from microorganisms.Type: GrantFiled: October 31, 2002Date of Patent: March 16, 2004Assignee: Ciba Specialty Chemicals CorporationInventors: Armando Di Teodoro, Werner Hölzl, Dieter Reinehr, Rudolf Zink
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Patent number: 6586599Abstract: A process for conducting coupling reactions of aryl halides with unsaturated silanes is described. The processes use N-heterocyclic carbenes as ancillary ligands in these coupling reactions. A coupling of an aryl halide with an unsaturated silane can be carried out by mixing, in a liquid medium, at least one strong base; at least one aryl halide or aryl pseudohalide in which all substituents are other than silyl groups, wherein the aryl halide has, directly bonded to the aromatic ring(s), at least one chlorine atom, bromine atom, or iodine atom; at least one silane wherein the silicon atom is quaternary, wherein one group bound to the silicon atom is unsaturated at the alpha or beta position, and wherein each of the remaining groups bound to the silicon atom is a saturated hydrocarbyl or a saturated hydrocarbyloxy group; at least one nickel, palladium, or platinum compound, wherein the formal oxidation state of the metal is zero or two; and at least one N-heterocyclic carbene.Type: GrantFiled: April 20, 2000Date of Patent: July 1, 2003Assignee: University of New Orleans Research and Technology FoundationInventors: Steven P. Nolan, Hon Man Lee
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Patent number: 6566571Abstract: Process for preparing monofunctional, bifunctional and/or polyfunctional biaryls of the formula (I) Ar—Ar′ (I) by reacting haloaromatics of the formula (II) Ar—X (II) with boron compounds of the formula (IIIa), (IIIb) and/or (IIIc) in the presence of at least one palladium complex of the formula (IVa) or (IVb)Type: GrantFiled: February 4, 2002Date of Patent: May 20, 2003Assignee: Degussa AGInventors: Thomas Riermeier, Matthias Beller, Alexander Zapf
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Patent number: 6548722Abstract: A process for Friedel-Crafts type liquid-phase alkylation or acylation of an aromatic compound using a hydrotalcite-type basic anionic clay catalyst represented by a formula: [(M2−)1−x(M3+)x(OH)2]x+[Ay−]x/yqH2O where M2+ is a divalent cation selected from Mg2+, Zn2+, Ni2+, Co2+, Mn2+, Cu2+ or a mixture thereof; M3+ is a trivalent cation selected from Ga3+, In3+ Al3+, Fe3+ Cr3+ or a mixture thereof; x is a mole fraction of trivalent cations in the range of about 0.05 to about 0.5; 0 is oxygen; H is hydrogen; Ay− is an anion; y minus is an anionic negative charge having a value of 1 minus or 2 minus; and q is a number of water molecules, as the water of hydration; and involving following steps: i.Type: GrantFiled: October 10, 2000Date of Patent: April 15, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Vasant Ramchandra Choudhary, Suman Kumar Jana
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Patent number: 6512147Abstract: A mixed liquid of two or more components different in boiling temperature from each other and soluble in or compatible with each other is evaporated into a mixed vapor having a similar composition to that of the mixed liquid by using an apparatus having a thin film evaporator (1) having a feed inlet (1a) and a delivery outlet (1b), while forcedly circulating the non-evaporated portion of the mixed multi-component liquid by withdrawing the non-evaporated mixed liquid portion from the delivery side end portion of the evaporator and returning the mixed liquid portion into the feed side end portion of the evaporator through a circulating line (3), and the resultant mixed multi-component vapor can be used as a mixed material vapor for a gas phase catalytic reaction for producing, for example, a mono and/or a di-alkylether of an aromatic dihydroxy compound.Type: GrantFiled: March 28, 2002Date of Patent: January 28, 2003Assignee: UBE Industries, Ltd.Inventors: Yukio Inaba, Kazunori Fujita, Hiroshi Kofuji
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Patent number: 6479709Abstract: A process for the production of a styrene derivative is provided. The process comprises reacting a Grignard reagent prepared from an aromatic halogen compound with a vinyl halide in the presence of a catalyst, wherein the catalyst is at least one member selected from the group consisting of manganese catlyst, iron catalyst, cobalt catalyst and rhodium catalyst.Type: GrantFiled: January 28, 1999Date of Patent: November 12, 2002Assignee: Tosoh CorporationInventors: Shin-ichi Ishikawa, Hisao Eguchi
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Patent number: 6472567Abstract: A process for the production of a styrene compound is provided. The process comprises reacting a Grignard reagent prepared from a tertiary butoxyphenyl halide with a vinyl halide in the presence of a catalyst, wherein the catalyst is at least one member selected from the group consisting of manganese catalyst, iron catalyst, cobalt catalyst and rhodium catalyst. The process overcomes the problems involved in the prior art, and is economical and safe. The styrene compound by the process is free from biphenyl.Type: GrantFiled: August 8, 2001Date of Patent: October 29, 2002Assignee: Tosoh CorporationInventors: Shin-ichi Ishikawa, Hisao Eguchi
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Patent number: 6417410Abstract: A method for producing ortho-alkylated phenols comprising reacting phenols represented by the general formula (1) with monohydric or dihydric alcohol in the presence of germanium oxide under conditions in which said alcohol is in the supercritical condition, wherein each of R1, R2, R3, R4 and R5 independently represents a hydrogen atom, or a linear or branched alkyl group having 1 to 10 carbon atoms.Type: GrantFiled: April 18, 2001Date of Patent: July 9, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoyuki Suzuki, Fumisato Goto
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Patent number: 6407292Abstract: A continuous process for the manufacture of alkylated diphenyl compounds such as diphenyl ether and diphenyl sulfides by alkylating a diphenyl compound such as diphenyl ether with an olefinic alkylating agent by passing a continuous flow of the diphenyl compound and the olefin over a solid particulate catalyst which comprises a molecular sieve of the MCM-22 family. The process is flexible. By adjusting feed compositions, products of different compositions and wide range of properties are produced.Type: GrantFiled: December 29, 1999Date of Patent: June 18, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: Margaret M. Wu, Rene B. Lapierre, Gilbert R. Jersey, Andrew Gene Horodysky
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Patent number: 6392111Abstract: Olefins containing aromatic substituents are synthesized without the addition of phosphonium salts or phosphanes with the aid of a PdII compound as a catalyst in the presence of nitrogen-containing additives such as N,N-dimethylglycine and a base.Type: GrantFiled: March 21, 2001Date of Patent: May 21, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer, Elke Westermann
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Patent number: 6339176Abstract: It provides a production method of 4-methoxymethyl-2,3,5,6-tetrafluorobenzenemethanol to allow 2,3,5,6-tetrafluoro-1,4-benzenedimethanol to react with an inorganic base in water, and then add dimethyl sulfate and a water-immiscible organic solvent selected from the group consisting of hydrocarbons and ethers to the reaction mixture, or to allow 2,3,5,6-tetrafluoro-1,4-benzenedimethanol to react with an inorganic base in water and said water-immiscible organic solvent, and then to add dimethyl sulfate to the reaction mixture.Type: GrantFiled: November 30, 2000Date of Patent: January 15, 2002Assignee: Sumitomo Chemical Company, Ltd.Inventors: Taro Hirose, Tatsuya Mori
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Patent number: 6326520Abstract: The invention relates to a method for producing a novel optically active compound represented by the general formula [IV]. This method includes the step of reacting a vinyl ether with a halogenated acetaldehyde in the presence of an optically active binaphthol-titanium complex. With this, the novel optically active compound can be produced very easily. Furthermore, the novel optically active compound can easily be oxidized to a novel optically active &agr;,&bgr;-dihydrexyketone represented by the general formula [V]. These novel optically active compounds can each be used as useful intermediates.Type: GrantFiled: August 20, 1999Date of Patent: December 4, 2001Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Koichi Mikami
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Patent number: 6291723Abstract: A catalyst composition comprising trifluoromethanesulfonic acid (also referred to as triflic acid) and a sufficient quantity of a substance (also referred to as a retarder) to decrease but not eliminate the catalytic activity of the acid is disclosed. Also disclosed, is a method and composition for condensing a hydroxyaryl with a diene by use of the catalyst composition. The method is capable of producing condensates having: a mole ratio of 1 mole of the diene to one mole of the hydroxyaryl; one mole of diene to two moles of the hydroxyaryl as well as higher molecular weight products such as resins by changes in temperature, time of reaction, type and quantity of retarder and other variables.Type: GrantFiled: September 2, 1999Date of Patent: September 18, 2001Assignee: Borden Chemical, Inc.Inventor: Arthur H. Gerber
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Patent number: 6277944Abstract: Alkylated and/or aralkylated polyhydroxy aromatic compounds prepared by reaction of a polyhydroxy aromatic compound (A) with an alkylene compound (B) at elevated temperature with the addition of a mixture (C) of oxalic acid and boric acid in a molar ratio of from 1:5 to 1:0, are useful, for example, as starting materials for the preparation of condensation polymers.Type: GrantFiled: June 22, 1995Date of Patent: August 21, 2001Assignee: Solutia Germany GmbH & Co. KGInventor: Uwe Neumann
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Patent number: 6215029Abstract: A process for the preparation of halohydroxydiphenyl compounds useful for protecting organic materials and articles from microorganisms, of the formula by acylation of a halogenated benzene compound (first stage), etherification of the acylated compound with a halogenated phenol compound (second stage), oxidation of the etherified compound (third stage) and hydrolysis of the oxidized compound in a fourth stage, according to the following reaction scheme: in which R1 and R2 independently of one another are F, Cl or Br; R3 and R4 independently of one another are hydrogen; or C1-C4alkyl; m is 1 to 3; and n is 1 or 2.Type: GrantFiled: June 9, 1999Date of Patent: April 10, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Urs Burckhardt, Armando Di Teodoro, Werner Hölzl, Dieter Reinehr, Rudolf Zink, Hanspeter Sauter, Uwe Gronde
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Patent number: 6215035Abstract: The invention relates to a process for the preparation of aralkylated aromatic compound with both small and large size aralkylating agents; wherein the catalyst used is heterogeneous solid catalyst removable from the reaction products by simple filtration, thus allowing the separated catalyst to be reused in the process. The catalyst is selected from micro or mesoporous gallosilicates and galloaluminosilicates, having structure similar to that of zeolites known in the prior art.Type: GrantFiled: January 11, 1999Date of Patent: April 10, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Vasant Ramchandra Choudhary, Suman Kumar Jana, B-Phani Kiran
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Patent number: 6127511Abstract: A preparation process of phenol aralkyl resin from phenol compound and aralkyl compound by controlling the temperature of reaction mass in the range of 70 to 240.degree. C. and simultaneously controlling the temperature of vapor phase potion and vapor-liquid interface portion of manufacturing equipment so as to keep the wall surface of the vapor phase portion and vapor-liquid interface portion in a wet state. The invention can prevent scale adhesion to the interior of manufacturing equipment, remarkably reduce the number of washing and scale removing procedures on the manufacturing equipment, and enable efficient manufacture of phenol aralkyl resin. When the phenol aralkyl resin obtained is used for a molding material, molded articles having excellent heat resistance and high reliability can be provided.Type: GrantFiled: December 3, 1998Date of Patent: October 3, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Tomoyuki Kawabata, Yuzo Ono, Teruo Yuasa, Yukio Fukui
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Patent number: 6084132Abstract: Fluorescent dyes which fluoresce in a variety of colors are produced from substituted and un-substituted 6-ring and 8-ring aromatic diketones by reductive alkylation with alkyl halides in the presence of zinc.Type: GrantFiled: December 3, 1999Date of Patent: July 4, 2000Assignee: Rohm and Haas CompanyInventor: Peter J. Heffron
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Patent number: 6063940Abstract: A 1-bromoalkylbenzene derivative is prepared by reacting a phenylalkene derivative with hydrogen bromide in the presence of a non-polar solvent. The phenylalkene derivative is prepared by reacting an alkenyl halide with metal magnesium to form a Grignard reagent, and then reacting the Grignard reagent with a benzyl halide derivative. An allyl Grignard reagent is prepared by reacting continuously an allyl halide derivative with metal magnesium in an organic solvent, in which the allyl halide derivative and metal magnesium are continuously added to the reaction system and the allyl Grignard reagent formed is continuously removed from the reaction system. The processes provide the intended compounds in high yields, high selectivities and high purities.Type: GrantFiled: February 13, 1997Date of Patent: May 16, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroaki Fujishima, Yasunobu Miyamoto, Masayoshi Minai, Tsutomu Matsumoto, Hideki Ushio, Takayuk Higashii
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Patent number: 5831102Abstract: Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; andR.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sup.1 and R.sub.Type: GrantFiled: February 8, 1996Date of Patent: November 3, 1998
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Patent number: 5792886Abstract: In producing (.+-.)-2-(6-methoxy-2-naphthyl)propionic acid or precursor thereof from 2-bromo-6-methoxynaphthalene, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl chloride in a solvent comprising one or more compounds, RZ, where R is a hydrogen atom or an alkyl group, and Z is --OH or --CN provided that if Z is --CN, R is alkyl, and in the presence of a strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed.Type: GrantFiled: January 8, 1997Date of Patent: August 11, 1998Assignee: Albemarle CorporationInventors: Mahmood Sabahi, Kevin J. Theriot, Brian F. Becnel
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Patent number: 5616713Abstract: A process of preparing 2-hydroxymethyl-3,5-dimethyl-4-methoxypyridine including the steps of acylating 2-methyl-1-penten-1-alkoxy-3-one to obtain 2-alkoxycarbonyl-3,5-dimethyl-4-pyrone; ammonolyzing 2-alkoxycarbonyl-3,5-dimethyl-4-pyrone to obtain 2-alkoxycarbonyl-3,5-dimethyl-4(1H)-pyridone; halogenating 2-alkoxycarbonyl-3,5-dimethyl-4(1H)-pyridone to obtain 2-alkoxycarbonyl-4-halo-3,5-dimethylpyridine; methoxylating 2-alkoxycarbonyl-4-halo-3,5-dimethylpyridine to obtain 2-methoxycarbonyl-3,5-dimethyl-4-methoxypyridine; and reducing 2-methoxycarbonyl-3,5-dimethyl-4-methoxypyridine to obtain 2-hydroxymethyl-3,5-dimethyl-4-methoxypyridine.Type: GrantFiled: July 22, 1996Date of Patent: April 1, 1997Assignee: Development Center for BiotechnologyInventors: Shan-Yen Chou, Tsai-Mien Huang, Shyh-Fong Chen, Hao Ku
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Patent number: 5602283Abstract: A multistage process of preparing N-alkyl-3,4-dialkyl-2,6-dinitroanilines starts from 3,4-dialkyl phenol and goes through the stages of 3,4-dialkyl-2,6-dinitrophenol and 3,4-dialkyl-2,6-ditro alkoxybenzene, wherein the latter are new compounds.Type: GrantFiled: May 23, 1995Date of Patent: February 11, 1997Assignee: Agan Chemical Manufacturers Ltd.Inventor: Morris Sarel
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Patent number: 5552071Abstract: Monoalkylated diphenyl oxides are high-temperature stable lubricant fluids having excellent low temperature viscometrics, and excellent additive solubility. These monoalkylated products are obtained by the alkylation of diphenyl oxide using, for example, an olefin alkylating agent, usually in the C.sub.8 to C.sub.18 range, in the presence of an acidic zeolite alkylation catalyst such as USY, which provides the selectivity for the monoalkylated product.Type: GrantFiled: September 23, 1994Date of Patent: September 3, 1996Assignee: Mobil Oil CorporationInventors: Leslie R. Rudnick, Ross A. Kremer, Derek A. Law
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Patent number: 5396011Abstract: An aromatic compound (such as benzene) is alkylated with a alkene (such as propylene) by contacting the two compounds together in the presence of a tungsten on zirconia catalyst. The reaction preferably takes place at elevated temperature and elevated pressure. The process of the invention has very high selectivity and conversion, and produces no or only very low amounts of undesirable oligomers (as measured by bromine number).Type: GrantFiled: December 28, 1992Date of Patent: March 7, 1995Assignee: Mallinckrodt Chemical, Inc.Inventor: Deborah K. Kuhn
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Patent number: 5352845Abstract: A process for manufacturing an optically active saturated compound of the general formula (25): ##STR1## wherein R.sub.20 represents a group for protecting a hydroxy group, R.sub.21, R.sub.22, and R.sub.23 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, is disclosed.Type: GrantFiled: March 25, 1993Date of Patent: October 4, 1994Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5344997Abstract: A fluorided silica-alumina catalyst, particularly one with a silica:alumina ratio in the range of 1:1-9:1 containing from 1 to 6 weight percent fluoride, is particularly effective in the liquid phase alkylation of benzene by linear olefins to produce linear alkyl benzenes at temperatures no greater than 140.degree. C. These catalysts also are effective in the liquid phase alkylation of alkylatable aromatics generally with a variety of alkylating agents, including olefins, alcohols, and alkyl halides.Type: GrantFiled: December 14, 1992Date of Patent: September 6, 1994Assignee: UOPInventor: Joseph A. Kocal
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Patent number: 5340483Abstract: A method for the selective separation of a particular compound from a mixture of compounds, by enzymatically converting a weakly adsorbable compound to a strongly adsorbable compound, and binding the converted compound to a material of appropriate chemical properties is described. Also described are methods for removing contaminants from wastewater streams, and from intermediate chemical process streams.Type: GrantFiled: June 11, 1993Date of Patent: August 23, 1994Assignee: University of Maryland at College ParkInventors: Gregory F. Payne, Jennifer Chu, Kimberlee K. Wallace, Wei-Qiang Sun
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Patent number: 5276194Abstract: A process is provided for the catalytic perfluoroalkylation of aromatic compounds, wherein a perfluoroalkyl iodide or mixture of iodides is reacted with an aromatic compound in the presence of an aqueous base, such as an alkali metal hydroxide or carbonate. The use of an aqueous strong base increases the rate of reaction. Further improvements in rate and yield are secured by employing, as the catalyst, a noble metal supported on porous silica microspheres.Type: GrantFiled: May 7, 1993Date of Patent: January 4, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Donald D. May
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Patent number: 5262552Abstract: An optically active (S)- or (R)-pentane compound of the general formula (11): ##STR1## wherein R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R.sub.14 represents a hydroxy, protected hydroxy or oxo group, if R.sub.14 is an oxo group, the ring denoting benzene in the above formula (11) is benzoquinone, R.sub.15 represents a hydrogen atom, hydroxy or acyloxy group, R.sub.16 represents a hydroxy or acyloxy group, and the chiral central carbon marked with a symbol * in said formula (11) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (11) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (11) is easily synthesized from an easily available optically active starting material.Type: GrantFiled: February 20, 1991Date of Patent: November 16, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5235115Abstract: A method for the selective ethylation of 2-alkoxy-naphthalene compounds at the 6 position of the naphthalene nucleus is disclosed.Type: GrantFiled: August 15, 1991Date of Patent: August 10, 1993Assignee: Amoco CorporationInventors: Gary P. Hagen, Wen-Dong Chang, Andreas B. Ernst, David A. Palmer, Daniel B. Pourreau, Patrick E. McMahon, John G. Schaffhausen