Patents Examined by Michael L. Shippen
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Patent number: 6906226Abstract: Hydroxymethyl-substituted polyfunctional phenols, expressed by the following structure: General structure (I) (wherein X represents: bivalent group (a) expressed by the following structure: General structure (II) (wherein R1, R2, R3 and R4 each independently represent a hydrogen atom or an alkyl group with a carbon atom number of 1 through 4); quadrivalent group (b) expressed by the following structure: General structure (III) (wherein R5 and R6 each independently represent a hydrogen atom or an alkyl group with a carbon atom number of 1 through 4); or bivalent group (c) expressed by the following structure: General structure (IV) (wherein R7 and R8 each independently represent a hydrogen atom or a monofluoromethyl, difluoromethyl or trifluoromethyl group; however, R7 and R8 cannot be both hydrogen atoms); wherein n takes 2 when X is bivalent group (a), takes 4 when X is quadrivalent group (b), or takes 2 when X is bivalent group (c)).Type: GrantFiled: April 3, 2003Date of Patent: June 14, 2005Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Kazuya Matsuishi, Takayuki Ohno, Taiichi Shiomi
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Patent number: 6900363Abstract: A process for preparing 1,2-dichloroethane which comprises (A) feeding an ethane-containing feed gas stream into a dehydrogenation zone and dehydrogenating ethane to ethane to give a product gas stream comprising ethane, ethane and secondary constituents, (B) feeding the ethan- and ethene-containing dehydrogenation product gas stream as a single stream or a plurality of substreams, optionally after having separated off secondary constituents, into one or more chlorination zones, chlorinating ethene to 1,2-dichloroethane to give one or more product gas streams comprising 1,2-dichloroethane, ethane and possibly further secondary constituents, isolating 1,2-dichloroethane and one or more ethane-containing circulating gas streams and recirculating the ethane-containing circulating gas stream or streams to the ethane dehydrogenation.Type: GrantFiled: December 4, 2002Date of Patent: May 31, 2005Assignee: BASF AktiengesellschaftInventors: Klaus Harth, Götz-Peter Schindler, Christian Walsdorff, Christian Kuhrs, Falk Simon
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Patent number: 6900359Abstract: A method of making a 3-alkylcycloalkanol of formula 2: where R1 represents a methyl or ethyl group, R2 represents hydrogen, R3 represents an ethyl, propyl, butyl, isobutyl or isoamyl group, R4 represents hydrogen and R5 represents hydrogen, or a methyl, ethyl, propyl, isobutyl or isoamyl group comprises the following steps: (1) carrying out an electrophilic substitution reaction of an alkyl group or precursor thereof, on an ortho-substituted alkylbenzene compound of formula 3: where R6 represents hydrogen, or a methyl or ethyl group; (2) hydrogenating the reaction product of step (1); (3) performing an elimination reaction on one or more reaction products of step (2) to produce one or more alkene products; and (4) hydrating the one or more alkene products of step (3) to provide a 3-alkylcycloalkanol of formula 2. The electrophilic substitution reaction of step (1) may be a Friedel-Crafts acylation, e.g. using an isopropyl ketone precursor, or a Friedel-Crafts alkylation, e.g. using an isobutyl group.Type: GrantFiled: August 10, 2001Date of Patent: May 31, 2005Assignee: Quest International Services B.V.Inventors: Simon Ellwood, Jan Thomas Haines, Christopher Paul Newman
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Patent number: 6894195Abstract: A process for the preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol comprising hydrogenating 4-methyl-2,3,5,6-tetrafluorobenzonitrile to 4-methyl-2,3,5,6-tetrafluorobenzylamine and converting 4-methyl-2,3,5,6-tetrafluorobenzylamine to 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol. The process optionally also comprises the further step of reacting 4-Methyl-2,3,5,6-tetrafluobenzyl alcohol with cis-Z-3-(2-chloro-1,1,1-trifluoro-2-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride to the form tefluthrin. 4-Methyl-2,3,5,6-tetrafluorobenzylamine and salts thereof are also claimed.Type: GrantFiled: October 18, 2001Date of Patent: May 17, 2005Assignee: Syngenta LimitedInventors: Raymond Vincent Heavon Jones, Stephen Martin Brown
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Patent number: 6891073Abstract: A method for producing bisphenol includes introducing a phenol and a ketone into a fixed, supported catalytic bed reactor system in a downflow mode, reacting the phenol and the ketone to form a reaction mixture, and recovering the bisphenol isomer from the reaction mixture. The preferred bisphenol isomer is bisphenol A, or p,p?-bisphenol A, produced from the reaction of phenol and acetone. The reactor for producing the bisphenol A from the reaction of phenol and acetone includes an ion exchange resin catalyst disposed in a bed and packing randomly distributed throughout the ion exchange resin catalyst to improve heat transfer efficiency and reduce compression of the catalyst bed.Type: GrantFiled: December 23, 2003Date of Patent: May 10, 2005Assignee: General Electric CompanyInventors: Gaylord Michael Kissinger, Allen Wai-Yee Ko, Michael D. Szillat, Brian T. Carvill
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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: 6888035Abstract: A method for producing phenol is disclosed which includes oxidizing cumene to form cumene hydroperoxide and acid cleavage to form cumene, phenol, acetone, and various byproducts, including alpha methylstyrene, followed by a subsequent hydrogenation of at least a part of the acetone and substantially all of the alpha methylstyrene.Type: GrantFiled: September 25, 2001Date of Patent: May 3, 2005Assignee: ExxonMobil Chemical Patents Inc.Inventors: Kevin J. Fallon, Chung-Ming Chi, Henry Y. Hwang, Frank A. Demers
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Patent number: 6888024Abstract: In a process for heterogeneously catalyzed partial gas phase oxidation of propene to acrylic acid, the starting reaction gas mixture is oxidized at a propene loading of <160 l(STP)/l·h in a first reaction stage over a fixed catalyst bed 1 which is accommodated in two successive reaction zones A, B, and the acrolein-containing product gas mixture of the first reaction stage is subsequently oxidized in a second reaction stage over a fixed catalyst bed 2 which is a accommodated in two successive reaction zones C, D, the highest temperature of the reaction gas mixture within reaction zone A being above the highest temperature of the reaction gas mixture within reaction zone B and the highest temperature of the reaction gas mixture within reaction zone C being above the highest temperature of the reaction gas mixture within reaction zone D.Type: GrantFiled: March 15, 2004Date of Patent: May 3, 2005Assignee: BASF AktiengesellschaftInventors: Martin Dieterle, Jochen Petzoldt, Klaus Joachim Müller-Engel, Heiko Arnold
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Patent number: 6878851Abstract: A process for the hydrogenation of acetone to prepare isopropanol is provided, wherein the hydrogenation reaction is carried out in a multi-tubular reactor.Type: GrantFiled: November 14, 2002Date of Patent: April 12, 2005Assignee: Shell Oil CompanyInventors: Leslie Andrew Chewter, Wilhelmus Cornelis Nicolaas Dekker, Stephane Jean Pierre Lecrivain, Andrew Neave Rogers
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Patent number: 6875898Abstract: The present invention relates to a process for preparing phenols by adding an aqueous base to the reaction product from the acid-catalyzed cleavage of alkylaryl hydroperoxides while maintaining a homogeneous phase prior to the work-up of the product.Type: GrantFiled: April 4, 2003Date of Patent: April 5, 2005Assignee: Ineos Phenol GmbH & Co. KGInventors: Manfred Weber, Reinhard Sigg, Michael Lausmann, Siegmund Greschek
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Patent number: 6875897Abstract: Polyisobutenylphenols are prepared by alkylating an aromatic hydroxy compound with substantially monoethylenically unsaturated and substantially homopolymeric polyisobutenes in the presence of a Lewis acid alkylation catalyst by a process in which an ether is additionally used as a cocatalyst, the ether having a molecular weight of at least 102 g/mol in the case of BF3 as the Lewis acid.Type: GrantFiled: September 27, 2001Date of Patent: April 5, 2005Assignee: BASF AktiengesellschaftInventors: Arno Lange, Hans Peter Rath
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Patent number: 6875896Abstract: A method for producing a high purity 1,1-bis(4-hydroxyphenyl)cyclohexane represented by the general formula (II), wherein R is a hydrogen atom or alkyl group, comprising the steps of: reacting cyclohexanone and a phenol represented by the general formula (I) in the presence of an acid catalyst; wherein R is the same as defined above, neutralizing the resultant reaction mixture with an alkali; primarily crystallizing and filtering a 1,1-bis(4-hydroxyphenyl)cyclohexane produced to obtain a primary crystallization filtrate; dissolving 100 parts by weight of the primary crystallization filtrate in a mixed solvent, which comprises 5 to 10 parts by weight of water and 100 to 200 parts by weight of a lower aliphatic ketone solvent, or 200 to 400 parts by weight of a lower aliphatic alcohol solvent; filtering the resulting solution through a zeta potential filter; and secondarily crystallizing and filtering the 1,1-bis(4-hydroxyphenyl)cyclohexane from the resulting filtrate in the presence of water.Type: GrantFiled: June 29, 2004Date of Patent: April 5, 2005Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Kazuhiko Yao, Tooru Nakaguchi, Kenji Ekawa
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Patent number: 6872860Abstract: This disclosure relates to a method for producing and using catalysts in the production of bisphenols, and in particular to a method for producing catalysts which contain poly-sulfur mercaptan promoters, and using these catalysts in the production of bisphenol-A and its derivatives.Type: GrantFiled: July 25, 2003Date of Patent: March 29, 2005Assignee: General Electric CompanyInventors: Jimmy Lynn Webb, James Lawrence Spivack
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Patent number: 6872858Abstract: The invention provides a diphenol represented by the general formula (I) wherein X is a divalent cyclic hydrocarbon group selected from 1-cyclohexene-1,4-ylene group, 1,4-cyclohexylene group and p-phenylene group, R is an alkyl group of 1-4 carbon atoms, n is 0 or an integer of 1-3 when X is 1-cyclohexene-1,4-ylene group and an integer of 1-3 when X is 1,4-cyclohexylene group or p-phenylene group. The invention further provides a process for the production of the same.Type: GrantFiled: February 7, 2002Date of Patent: March 29, 2005Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Kouji Muragaki, Tadashi Hiramine, Hiroyasu Ohno
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Patent number: 6858759Abstract: A method for the manufacture of bisphenols comprises introducing a combined feed stream comprising a feed stream and a recycle stream into a reactor system comprising at least one reactor containing a catalytic proportion of an acid catalyst and wherein the combined feed stream comprises a carbonyl compound and a stoichiometric excess of phenol; removing from the reactor system a reactor effluent; splitting the reactor effluent into a crystallization feed stream and an effluent recycle stream; extracting from said crystallization feed stream a bisphenol adduct, remainder comprising a mother liquor stream; dehydrating said mother liquor stream and said effluent recycle stream in a dehydrator wherein excess water and carbonyl compound are removed; and recycling the dehydrated mother liquor and the dehydrated effluent recycle stream back to the combined feed stream to effect improved production of p,p-bisphenol, along with increased reactor selectivity and reduced promoter quantities.Type: GrantFiled: August 12, 2003Date of Patent: February 22, 2005Assignee: General Electric CompanyInventors: Martin Herke Oyevaar, Rudy Francois Alain Jos Peemans, Eduard Hendricus Schlarmann
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Patent number: 6858758Abstract: A method for producing a bisphenol is disclosed. The method entails reacting in at least one first reactant selected from a first group consisting of phenol and substituted phenols with at least one second reactant selected from a second group consisting of ketones and diols, in the presence of hydrogen chloride catalyst and volatile sulphur compound having an SH bond as co-catalyst. The reaction product is a mixture that contains bisphenol, first reactant and second reactant. The catalyst and co-catalyst and water of reaction are separated by distillation. The method is characterized by the high reaction rates and selectivities.Type: GrantFiled: July 16, 2002Date of Patent: February 22, 2005Assignee: Bayer AktiengesellschaftInventors: Tony Van Osselaer, Werner Verhoeven, Domien Sluyts
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Patent number: 6858760Abstract: A fluorine-containing cyclic compound is represented by the formula 1: wherein each of R1, R2 and R3 independently represents a hydrogen, alkyl group, fluorine, fluoroalkyl group or hexafluorocarbinol group, wherein at least one of the hexafluorocarbinol groups may partly or totally be protected with a protecting group, and wherein the protecting group is (a) a straight-chain, branched or cyclic hydrocarbon group having a carbon atom number of 1-25 or (b) an aromatic hydrocarbon group and optionally contains a fluorine atom, oxygen atom, nitrogen atom or carbonyl bond.Type: GrantFiled: February 20, 2004Date of Patent: February 22, 2005Assignee: Central Glass Company, LimitedInventors: Haruhiko Komoriya, Satoru Miyazawa, Katsunori Kawamura, Satoru Kobayashi, Kazuhiko Maeda
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Patent number: 6852874Abstract: A process for catalyzing asymmetric dihydroxylations of olefins employs an Os(VI) complex as a catalytic intermediate in the formation of chiral vicinal diol products. The process requires a chiral bidentate ligand that favors diol formation in the “second cycle” of asymmetric dihydroxylation.Type: GrantFiled: August 28, 2001Date of Patent: February 8, 2005Assignee: The Scripps Research InstituteInventors: K. Barry Sharpless, Malin Andersson, Robert Epple, Valery Fokin
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Patent number: 6849770Abstract: The present invention relates to a method for obtaining purified hydroxytyrosol from products and by-products derived from the olive tree by means of two-step chromatographic treatment. The invention uses a non-activated ion exchange resin chromatographic method, followed by a second treatment on an XAD-type absorbent non-ionic resin which concentrates and completely purifies the hydroxytyrosol by means of elution with a methanol or ethanol:water dissolution (from 30 to 33%). The method of the invention can also be applied to two-phase pomaces, three-phase pomaces and stones if they are subjected to a steam explosion process.Type: GrantFiled: August 13, 2003Date of Patent: February 1, 2005Assignee: Consejo Superior de Investigaciones CientificasInventors: Juan Fernandez-Bolaños Guzman, Antonia Heredia Moreno, Guillermo Rodriguez Gutierrez, Rocío Rodriguez Arcos, Ana Jimenez Araujo, Rafael Guillen Bejarano
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Patent number: 6849771Abstract: The invention relates to a process for converting 1-phenylethanol into styrene, which process involves: (1) contacting a feed containing 1-phenylethanol, organic acid and 2-phenylethanol with a catalyst to obtain a product containing styrene, and (2) removing ester compounds based on 2-phenylethanol and organic acid from the product of step (1), in which process the feed of step (1) has a molar ratio of organic acid to 2-phenylethanol of at least 1:10.Type: GrantFiled: August 6, 2003Date of Patent: February 1, 2005Assignee: Shell Oil CompanyInventors: Timothy Michael Nisbet, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram