Halogen Containing Reactant (e.g., Dehydrohalogenation, Etc.) Patents (Class 568/323)
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Patent number: 10101653Abstract: A resist composition comprising a base polymer and a sulfonium or iodonium salt of iodinated phenoxy or iodinated phenylalkoxy-containing fluorinated sulfonic acid offers a high sensitivity and minimal LWR or improved CDU independent of whether it is of positive or negative tone.Type: GrantFiled: August 2, 2017Date of Patent: October 16, 2018Assignee: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Masaki Ohashi
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Patent number: 9809524Abstract: The invention relates to a process for the preparation of a compound of formula I comprising a) reacting a compound of formula II in the presence of magnesium or an organometallic reagent of formula III R1M2X (III), wherein R1 is CI-C4alkyl; M2 is Li or Mg and X is halogen or absent; with a compound of formula IV CF3—C(O)—R2 (IV), wherein R2 is halogen, hydroxyl, CI-C4alkoxy, (di-CI-C4alkyl)amino, OC(O)CF3, phenoxy or OM1; wherein M1 is Lithium, Magnesium, Sodium or Potassium; to a compound of formula V, and b) reacting the compound of formula V with alkali metal fluoride in the presence of catalytic amounts of a phase transfer catalyst in the presence of a polar solvent to the compound of formula I.Type: GrantFiled: October 8, 2015Date of Patent: November 7, 2017Assignee: Syngenta ParticipationsInventor: Helmars Smits
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Patent number: 9783476Abstract: A method produces a 2?-trifluoromethyl-substituted aromatic ketone and includes reacting a 2-halogen-substituted benzotrifluoride compound with magnesium metal to convert the compound to a Grignard reagent; and reacting the Grignard reagent with an acid anhydride; and then hydrolyzing the resultant to produce a 2?-trifluoromethyl-substituted aromatic ketone. The method of producing a 2?-trifluoromethyl-substituted aromatic ketone enables 2?-trifluoromethyl-substituted aromatic ketone to be produced without using expensive raw materials by generating a Grignard reagent as an intermediate and reacting this Grignard reagent with an acid anhydride in an efficient productivity.Type: GrantFiled: September 7, 2015Date of Patent: October 10, 2017Assignee: Toray Fine Chemicals Co., Ltd.Inventors: Jiro Nakatani, Tatsuhiro Nozoe
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Patent number: 9035101Abstract: Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein M1 is Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water.Type: GrantFiled: September 30, 2013Date of Patent: May 19, 2015Assignee: E.I. du Pont de Nemours and CompanyInventor: Gary David Annis
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Patent number: 9000212Abstract: Provided by the present invention is a method for efficient oxidation of alcohols by using, as a catalyst for dehydrogenation oxidation, a ruthenium complex which can be easily produced and easily handled and is obtainable at a relatively low cost. The invention relates to a method of producing a compound having a carbonyl group by dehydrogenation oxidation of alcohols by using as a catalyst the ruthenium carbonyl complex represented by the following general formula (1) RuXY(CO)(L) (1) (in the general formula (1), X and Y may be the same or different from each other and represent an anionic ligand, and L represents a tridentate aminodiphosphine ligand).Type: GrantFiled: April 18, 2012Date of Patent: April 7, 2015Assignee: Takasago International CorporationInventors: Taichiro Touge, Kunimori Aoki, Hideki Nara, Wataru Kuriyama
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Patent number: 8987520Abstract: This invention relates to fluoroalkyl and chlorofluoroalkyl benzenes with relatively high boiling points, having zero ozone depletion potential and low global warming potential. This invention also relates to the preparation of such fluoroalkyl and chlorofluoroalkyl benzenes. These materials can be used as reaction and heat transfer media, cleaning agents and as intermediates for biologically active materials.Type: GrantFiled: December 18, 2013Date of Patent: March 24, 2015Assignee: E I du Pont de Nemours and CompanyInventor: Viacheslav A Petrov
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Patent number: 8946483Abstract: The present invention relates to a method of obtaining radiopharmaceutical precursors, and in particular precursors to protected amino acid derivatives, which are used as precursors for production of radiolabelled amino acids for use in in vivo imaging procedures, such as positron emission tomography (PET).Type: GrantFiled: July 20, 2012Date of Patent: February 3, 2015Assignee: GE Healthcare LimitedInventors: Radha Achhanath, Srinath Balaji, Asfal Mohammed Kadavilpparampu Mohamed, Sondre Nilsen, Steven Michael Fairway
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Publication number: 20140371479Abstract: A non-carcinogenic process for the activation of zinc metal in a medium polarity solvent, wherein said zinc metal is activated by the reaction thereof with a halogen and a lithium compound selected from lithium halides and lithium pseudohalides, the use of said activated zinc metal for the preparation of an organozinc halide of formula R—ZnX, and a process for the preparation of compounds obtainable by the reaction of said organozinc halide of formula R—ZnX with compounds having functionality enabling them to react with said organozinc halide.Type: ApplicationFiled: January 30, 2013Publication date: December 18, 2014Applicants: CAMBRIDGE DISPLAY TECHNOLOGY LIMITED, SUMITOMO CHEMICAL COMPANY LIMITEDInventors: Jonathan Pillow, James Morey
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Publication number: 20140303374Abstract: Provided by the present invention is a method for efficient oxidation of alcohols by using, as a catalyst for dehydrogenation oxidation, a ruthenium complex which can be easily produced and easily handled and is obtainable at a relatively low cost. The invention relates to a method of producing a compound having a carbonyl group by dehydrogenation oxidation of alcohols by using as a catalyst the ruthenium carbonyl complex represented by the following general formula (1) RuXY(CO)(L) (1) (in the general formula (1), X and Y may be the same or different from each other and represent an anionic ligand, and L represents a tridentate aminodiphosphine ligand).Type: ApplicationFiled: April 18, 2012Publication date: October 9, 2014Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Taichiro Touge, Kunimori Aoki, Hideki Nara, Wataru Kuriyama
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Patent number: 8828908Abstract: Bicyclic dione compounds of formula (I), and derivatives thereof, which are suitable for use as herbicides.Type: GrantFiled: May 27, 2008Date of Patent: September 9, 2014Assignee: Syngenta LimitedInventors: Christopher John Mathews, Matthew Brian Hotson, Alan John Dowling, James Nicholas Scutt, Mangala Govenkar, Lee Challinor
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Publication number: 20140200372Abstract: This invention relates to fluoroalkyl and chlorofluoroalkyl benzenes with relatively high boiling points, having zero ozone depletion potential and low global warming potential. This invention also relates to the preparation of such fluoroalkyl and chlorofluoroalkyl benzenes. These materials can be used as reaction and heat transfer media, cleaning agents and as intermediates for biologically active materials.Type: ApplicationFiled: December 18, 2013Publication date: July 17, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: Viacheslav A. Petrov
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Publication number: 20140175292Abstract: Tritiated planar carbon forms and their production are provided. Methods are provided for the stoichiometrically controlled labeling of planar carbon forms capitalizing on normal flaws of carboxylic acids ubiquitously present in commercial preparations of these planar carbon forms. Alternative methods include generation of a metallated intermediate whereby a metal is substituted for hydrogen on the carbon backbone of a planar carbon form. The metalized intermediate is then reacted with a tritium donor to covalently label the planar carbon form. The tritiated planar carbon forms produced are useful, for example, for determination of a biological property or environmental fate of planar carbon forms.Type: ApplicationFiled: February 26, 2014Publication date: June 26, 2014Applicant: PerkinElmer Health Sciences, Inc.Inventor: Crist N. Filer
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Publication number: 20140155617Abstract: Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein M1 is Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water.Type: ApplicationFiled: September 30, 2013Publication date: June 5, 2014Applicant: E.I. du Pont de Nemours and CompanyInventor: Gary David Annis
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Patent number: 8686191Abstract: The present invention relates to the technical field of radiation curing photopolymerization initiator, and particularly to an environmentally-friendly new oxidation process for converting several specific aryl-1,2-diol compounds to corresponding arylhydroxyketones.Type: GrantFiled: December 29, 2011Date of Patent: April 1, 2014Assignee: Shenzhen Liv-Chemth Co., LtoInventors: Ting Chen, Yu Wang
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Patent number: 8604251Abstract: The invention pertains to novel oligofunctional photoinitiators of the formula (1) or (1A). R1 and R2 are methyl or together are —(CH2)5—; and n is 2 or 3, and the solvent in (1A) is water or an organic solvent; and their use in photopolymerizable compositions, in particular inks.Type: GrantFiled: March 19, 2010Date of Patent: December 10, 2013Assignee: BASF SEInventors: Ulrich Berens, Jean-Luc Birbaum, Katia Studer
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Publication number: 20130296611Abstract: The present invention relates to the technical field of radiation curing photopolymerization initiator, and particularly to an environmentally-friendly new oxidation process for converting several specific aryl-1,2-diol compounds to corresponding arylhydroxyketones.Type: ApplicationFiled: December 29, 2011Publication date: November 7, 2013Inventors: Ting Chen, Yu Wang
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Publication number: 20130267712Abstract: A method of preparing an aryl carbonyl or aryl thiocarbonyl compound, comprises reacting an N-(nitroaryl)-amide or N-(nitroaryl)-thioamide with an aromatic ring, with a superacid catalyst, to produce the aryl carbonyl or aryl thiocarbonyl compound. The superacid is present in an amount of at most 8 equivalents in proportion to the N-(nitroaryl)-amide or N-(nitroaryl)-thioamide. A method of preparing aryl amide or aryl thioamide, comprises reacting an N-(nitroaryl)-carbamide or N-(nitroaryl)-thiocarbamide with an aromatic ring, with a superacid catalyst, to produce the aryl amide or aryl thioamide.Type: ApplicationFiled: March 14, 2013Publication date: October 10, 2013Applicant: Board of Trustees of Northern Illinois UniversityInventors: Douglas A. Klumpp, Erum K. Raja
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Patent number: 8546618Abstract: Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein M1 is Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water.Type: GrantFiled: April 8, 2009Date of Patent: October 1, 2013Assignee: E.I. du Pont de Nemours and CompanyInventor: Gary David Annis
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Publication number: 20130123545Abstract: Diketopyracene is synthesized in high yield without using carbon disulfide as a solvent. A special solvent is used. In particular, a solvent having a benzene ring that has two or more chlorine atoms is used. The two chlorine atoms are not in meta positions but in ortho positions of the benzene ring.Type: ApplicationFiled: July 20, 2011Publication date: May 16, 2013Applicant: CANON KABUSHIKI KAISHAInventors: Kei Tagami, Masashi Hashimoto, Hiroki Ohrui
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Publication number: 20130123514Abstract: The disclosure relates to catalytically active carbocatalysts, e.g., a graphene oxide or graphite oxide catalyst suitable for use in a variety of chemical transformations. In one embodiment, it relates to a method of catalyzing a chemical reaction of an organic molecule by reacting the organic molecule in the presence of a sufficient amount of graphene oxide or graphite oxide for a time and at a temperature sufficient to allow catalysis of a chemical reaction. According to other embodiments, the reaction may be an oxidation reaction, a hydration reaction, a dehydrogenation reaction, a condensation reaction, or a polymerization reaction. Some reactions may include auto-tandem reactions. The disclosure further provides reaction mixtures containing an organic molecule and graphene oxide or graphite oxide in an amount sufficient to catalyze a reaction of the organic molecule.Type: ApplicationFiled: May 27, 2011Publication date: May 16, 2013Applicant: GRAPHEA, INC.Inventors: Christopher W. Bielawski, Daniel R. Dreyer, Hong-Peng Jia
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Patent number: 8394993Abstract: The invention relates to a process for the preparation of cyclopropyl benzyl ketone compounds of formula (II) wherein R1 represents fluorine or chlorine atom or C1-4 alkoxy group, by the reaction of a Grignard reagent, obtained from the reaction of compound of formula (V), wherein X represents chlorine or fluorine atom, with the compound of formula (IV), wherein R2 represents C1-4 alkyl group, having a straight or branched chain. The process can be applied preferably on industrial scale. Compound of formula (II), wherein R represents a fluorine atom in position 2 is an intermediate of the preparation process of prasugrel, which is a platelet inhibitor used in the therapy.Type: GrantFiled: November 27, 2008Date of Patent: March 12, 2013Assignee: Egis Gyogyszergyar Nyilvanosan Mukodo ReszvenytarsasagInventors: Tibor Mezei, Gyula Lukács, Enikó Molnár, József Barkóczy, Balázs Volk, Márta Porcs-Makkay, János Szulágyi, Mária Vajjon
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Publication number: 20130023661Abstract: The present invention relates to the use of compounds of the formula (I) as fluorinating reagents, to a process for the fluorination of organic compounds by reaction thereof with compounds of the formula (I), and to compounds of the formula (I).Type: ApplicationFiled: March 7, 2011Publication date: January 24, 2013Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNGInventors: Nikolai (Mykola) Ignatyev, Aleksandra Atatrah, Peter Barthen, Walter Frank
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Publication number: 20120107593Abstract: Disclosed are graphene oxide membrane materials of high surface area, which membranes suitably have a surface area of above about 200 ?m and exhibit electrical conductivity in excess of about 200 S/m. Also provided are methods of synthesizing such membranes, as well as devices and sensors that incorporate these novel grapheme materials.Type: ApplicationFiled: December 4, 2009Publication date: May 3, 2012Applicant: The Trustees of the University of PennsylvaniaInventors: Zhengtang Luo, Alan T. Johnson
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Publication number: 20110263720Abstract: The present invention is directed to a method of synthesizing a compound of Formula I: the method comprising oxidizing alpha-tocopherol with a metal salt oxidizing agent to form the compound of Formula I, wherein the stoichiometric ratio (mol/mol) of metal salt oxidizing agent/alpha-tocopherol is 1.6 to 4. The invention is also directed to a method of synthesizing a compound of Formula I, the method comprising (a) hydrolyzing alpha-tocopheryl acetate in the presence of a base; (b) neutralizing the hydrolyzing of (a), thereby forming alpha-tocopherol; and (c) oxidizing the alpha-tocopherol of (b) with a metal salt oxidizing agent to form the compound of Formula I, wherein the stoichiometric ratio (mol/mol) of metal salt oxidizing agent/alpha-tocopherol is 1.6 to 4.Type: ApplicationFiled: March 9, 2011Publication date: October 27, 2011Applicant: Penwest Pharmaceuticals Co.Inventors: Steven D. PAISLEY, Jason M. LePree, Amale Hawi, Michael Eckhoff
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Publication number: 20110082312Abstract: The present invention relates to a process for the preparation of compounds containing CF3O groups using compounds containing at least one group Y, in which Y=—Hal, —OSO2(CF2)zF, —OSO2CzH2z+1 (z=1-10), —OSO2F, —OSO2Cl, —OC(O)CF3— or —OSO2Ar, to a process for the preparation of compounds containing CF3O groups using KOCF3 and/or RbOCF3, and to novel compounds containing CF3O groups, and to the use thereof.Type: ApplicationFiled: May 4, 2009Publication date: April 7, 2011Applicant: MERCK PATENT GESELLSCHAFT MIT DESCHRANKTER HAFTUNGInventors: Nikolai (Mykola) Ignatyev, Wolfgang Hierse, Martin Seidel, Andreas Bathe, Jens Schroeter, Karsten Koppe, Thorsten Meier, Peter Barthen, Walter Frank
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Publication number: 20110065962Abstract: Process for the preparation of aromatic alpha-hydroxyketones (aromatic ?-hydroxyketones) that does not require the use of chlorine, sulfuryl chloride or bromine and comprises the halogenation of an intermediate aromatic ketone with a hydrogen halide in the presence of an oxidising compound.Type: ApplicationFiled: May 7, 2009Publication date: March 17, 2011Inventors: Enzo Meneguzzo, Gabriele Norcini, Giuseppe Li Bassi
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Publication number: 20110009638Abstract: Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein M1 is Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water.Type: ApplicationFiled: April 8, 2009Publication date: January 13, 2011Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventor: Gary David Annis
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Patent number: 7718757Abstract: An aromatic polymer, containing a repeating unit represented by Formula (I), and having properties (A1) and (B1): (A1) the number average degree of polymerization of an acetylated product obtained by acetylation of the hydroxyl groups of the polymer is 3 or more, and (B1) at a wavelength where an absolute value of molar ellipticity (degree·cm?2·dmol?1) per mole of the repeating unit of the acetylated product in a circular dichroism spectrum of the acetylated product reaches maximum in a wavelength range of from 200 to 350 nm, the absolute value is 50,000 or more: wherein R represents a hydrocarbon, hydrocarbon-oxy, hydrocarbon-mercapto or hydrocarbon-amino group that may be substituted; the two R's may bind to each other to form a ring; and the repeating unit represented by Formula (I) has no symmetrical plane that has two binding sites and that is perpendicular for the benzene ring.Type: GrantFiled: May 8, 2006Date of Patent: May 18, 2010Assignee: Sumitomo Chemical Company LimitedInventors: Shigeki Habaue, Soichiro Murakami, Hideyuki Higashimura
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Publication number: 20100121082Abstract: The invention relates to a process for preparing 2,4-dihydroxyphenyl 4-methoxybenzyl ketones of the formula (I) by Friedel-Crafts acylation in hydrogen fluoride (HF). 2,4-Dihydroxyphenyl 4-methoxybenzyl ketones of the formula (I) in which R1 and R2 are each hydrogen, chlorine, fluorine, bromine, iodine, CF3, methyl, optionally substituted alkoxy, —OCF3, —C(CH3)3, —CH2(CH3)2, —CH(CH3)2, R3 is hydrogen, Cl, F, Br, optionally substituted alkyl, optionally substituted alkoxy, —C(CH3)3, and X is hydroxyl, F, Cl, Br, optionally substituted alkoxy, are obtained in high yield and high purity by reacting phenylacetic acid derivatives of the formula (II) with phenols of the formula (III) in liquid hydrogen fluoride (HF).Type: ApplicationFiled: February 16, 2008Publication date: May 13, 2010Inventors: Sergii Pazenok, Norbert Lui
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Patent number: 7553988Abstract: A method is provided for producing a specific crosscoupling compound and a specific catalyst for producing the compound. The method includes reacting in the presence of a base and a nickel compound catalyst organic halide of the formula n?(R1X1n), wherein R1 is a hydrocarbon group and the ? and ? carbons to X? are sp3 carbon atoms; X1 is a chlorine, bromine, or iodine atoms, and n and n1 are 1 or 2 but not both 2, with a compound having the formula m{R2(BX22)n?} where an R2 is an aryl, heteroaryl, or alkenyl group, and n? is 1 or 2, X2 is independently a hydroxyl group, an alkoxy or arylalkoxy group or X22 together form an alkylenedioxy or arylenedioxy group, and m represents 1 or 2 but m?n, and the boron atom is bonded to a sp2 carbon atom of R2 group or a boronic acid trimer anhydride.Type: GrantFiled: August 17, 2006Date of Patent: June 30, 2009Assignee: Sumitomo Chemical Company, LimtedInventors: Tamon Itahashi, Takashi Kamikawa
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Patent number: 7501544Abstract: The present invention relates to a process for the preparation of compounds of formula (I), wherein the substituents are as defined in claim 1, by reacting a compound of formula (II), either with a chlorination or bromination agent or with a compound of formula (III) CI—SO2R9, R9 being C1-C4alkyl, C1-C4haloalkyl, phenyl or C1-C4alkyl-substituted phenyl, to form the compound of formula (IV), reacting the compound of formula (IV) with a compound of formula (V) M+-O?—C(O)—Y wherein Y is as defined above and M+ is the hydrogen cation or an alkali metal ion, alkaline earth metal ion or ammonium ion, to form the compound of formula (VI) and treating that compound with a cyanide source in the presence of a base.Type: GrantFiled: April 29, 2005Date of Patent: March 10, 2009Assignees: Syngenta Crop Protection, Inc., Syngenta LimitedInventors: David Anthony Jackson, Andrew Edmunds, Martin Charles Bowden, Ben Brockbank
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Patent number: 7462650Abstract: The Invention relates to novel ketones of formulae (I) and (II) wherein R1, R2, R3 and R4 are, for example, C1-C8alkyl, R5 is, for example, hydrogen, A is CI, Br, -0-R7, —NR8R9 or —S—R16, A? is —O—, —NH— or —NR8—, X and Y are each independently of the other —O—R10 or —N(R11)(R12), n is an integer from 1 to 10, R6 is, for example, an n-valent radical of linear or branched C2-C20alkyl the carbon chain of which may be interrupted by cyclohexanediyl, phenylene, —CH(OH)—, —C(C2H5)(CH2—CH2—OH)—, —C(CH3)(CH2—CH2—OH)—, —C(CH2—CH2—OH)2—, —N(CH3)—, —N(C2H5)—, —N(CH2—CH2—OH)—, —CO—O—, —O—CO—, —P(CH2—CH2—OH)—, —P(O)(CH2—CH2—OH)—, -0-P(O—CH2—CH2—OH)—O—, -0-P(O)(0-CH2—CH2—OH)—O—, —O-cyclohexanediyl-C(CH3)2-Cyclohexanediyl-O—, —O-phenylene-C(CH3)2-phenylene-O—, —O-phenylene-CH2-phenylene-O—, —Si(CH3)2—, -0-Si(CH3)2—O—, —O—Si(CH3)(0-CH3)—O—, —Si(CH3)(R17)—O—Si(CH3)(R18)—, 5-(2-hydroxyethyl)-[1,3,5]triazinane-2,4,6-trione-1,3-diyl and/or by from one to nine oxygen atoms.Type: GrantFiled: May 4, 2004Date of Patent: December 9, 2008Assignee: Ciba Specialty Chemicals CorporationInventors: Reinhard H. Sommerlade, Rinaldo Hüsler, Stephan Ilg, André Fuchs, Souâd Boulmaâz, Jean-Luc Birbaum
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Publication number: 20080221350Abstract: Process for preparing compounds by cross-coupling of enolizable carbonyl compounds, nitriles or their analogues with substituted aryl or heteroaryl compounds in the presence of a Brönsted base and of a catalyst or precatalyst containing a.) a transition metal, a complex, a salt or a compound of this transition metal from the group V, Mn, Fe, Co, Ni, Rh, Pd, Ir, Pt) and b.) at least one sulphonated phosphane ligand in a solvent or solvent mixture.Type: ApplicationFiled: September 12, 2006Publication date: September 11, 2008Inventors: Andreas Meudt, Sven Nerdinger, Bernd Wilhelm Lehnemann, Till Vogel, Victor Snieckus
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Patent number: 7279604Abstract: The compound boron carbide, B4C, is an effective catalyst for the alkylation and acylation of aromatics to produce polybenzyls, ketones, esters and alkyl benzenes. The catalyst boron carbide is also effective in conducting intramolecular Friedel-Crafts type reactions to produce cyclic ketones.Type: GrantFiled: May 30, 2006Date of Patent: October 9, 2007Assignee: The College of N.J.Inventor: Philip Edward Dumas
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Patent number: 7238832Abstract: There is provided a method for producing a coupling compound of formula (1): (Y—)(n?1)R1—R2—(R1)(n??1)??(1) wherein R1, R2 n and n? are as defined below, Y is R2 or X as defined below, which method comprises reacting an organic halogen compound of formula (2): n?(R1X1n)??(2) wherein X1 represents a bromine or iodine, R1 represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which ? and ? carbon atoms in relation to X1 are sp3 carbon atoms, n and n? each independently represent an integer of 1 or 2, and provided that n and n? do not simultaneously represent 2, with an organic boron compound of formula (3): m{R2(BX22)n?}??(3) wherein R2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkenyl group and the boron atom is bonded with a sp2 carbon atom thereof, X2 represents a hydroxyl or alkoxy group, n? is as defined above, m represents an integer of 1 or 2, and m is not more than n, in the presence of a catalyst comprising a) a nickType: GrantFiled: February 18, 2004Date of Patent: July 3, 2007Assignee: Sumitomo Chemical Company, LimitedInventors: Tamon Itahashi, Takashi Kamikawa
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Patent number: 7202384Abstract: The present invention relates to a process for producing 5-nitro-3,4-dihydro-1(2H)-naphthalinone, 1,5-naphthalenediamine and 1,5-naphthalene diisocyanate, in which 4-(2-nitrophenyl)-n-butyronitrile is converted to 4-(2-nitrophenyl)-n-butyric acid.Type: GrantFiled: April 7, 2006Date of Patent: April 10, 2007Assignee: Bayer MaterialScience AktiengesellschaftInventors: Joachim Zechlin, Kai Verkerk, Dietmar Wastian, Kartin Joschek, Tim Loddenkemper, Wilfried Pinke, Michael Schelhaas, Georg Ronge
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Patent number: 7148384Abstract: The invention relates to a process for preparing fluorinated acetophenones from fluorinated aryl compounds in the presence of N-hydroxyphthalimide and the use thereof.Type: GrantFiled: June 17, 2004Date of Patent: December 12, 2006Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Jens Peter Joschek
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Patent number: 7129367Abstract: Palladum-phosphine complexes obtained by reacting a 5 compound of formula (1) below with a palladium compound: F(I) (wherein R1 is a hydrogen atom, an alkyl group, a cycloalkyl group or a phenyl group which may be substituted; R2 and R3 are each, the same or different, an alkyl group, a cycloalkyl group or a phenyl group which may be substituted; R4 and R5 are each, the same or different, a hydrogen atom, an alkyl group, a cycloalkyl group or a phenyl group which may be substituted; R6, R7, R8 and R9 are each, the same or different, an alkyl group, a cycloalkyl group, a phenyl group which may be substituted, an alkoxyl group, a dialkylamino group, a halogen atom, a phenyl group, a benzyl group, a naphthyl group or a halogenated alkyl group; R6 and R7, R8 and R9 may be combined to form, each, a fused ring, a trimethylene group, a tetramethylene group or a 20 methylenedioxy group; p, q, r and s are each an integer of 0 to 5; and p+q, and r+s are each in the range of 0 to 5.Type: GrantFiled: February 12, 2004Date of Patent: October 31, 2006Assignee: Takasago International CorporationInventors: Ken Suzuki, Yoji Hori
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Patent number: 7119235Abstract: According to one aspect of the invention, there is provided the use of an organic ionic liquid in a zeolite-catalysed process, for example an acylation, alkylation, isomerisation or hydrocracking process in which zeolites act as catalysts or catalyst precursors, especially Friedel-Crafts alkylation and acylation procedures.Type: GrantFiled: October 2, 2002Date of Patent: October 10, 2006Assignee: The Queen's University of BelfastInventors: Christopher Hardacre, David W. Rooney, Jillian M. Thompson, Suhas P. Katdare
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Patent number: 7087789Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“?CF2?”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.Type: GrantFiled: January 12, 2004Date of Patent: August 8, 2006Assignee: University of Southern CaliforniaInventors: G. K. Surya Prakash, Jinbo Hu, George A. Olah
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Patent number: 6984760Abstract: This invention particularly relates to a process for the acylation of aromatic compounds by an acylating agent for preparing corresponding acylated aromatic compounds, using a solid catalyst.Type: GrantFiled: March 31, 2004Date of Patent: January 10, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Vasant Ramchandra Choudhary, Rani Jha
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Patent number: 6943257Abstract: The present invention provides a process for preparing an aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite anion and halodimethylsulfonium halide generated in situ from hydrobromic acid/DMSO or hydriodic acid/DMSO. The process for producing compounds of the formula (1) is disclosed (1) wherein X is bromine or iodine: Y is carbon or nitrogen; R1, R2, R3, R4 and R5 which may be the same or different and are selected independently from the group consisting of a hydrogen, a hologen, a C1-C8 alkyl, a C1-C10 alkoxy, a nitro, a formyl, an aryl, a benzyl, a C2-C10 alkylcarbonyl and an arylcarbonyl, provided that adjacent groups as selected from R1, R2, R3, R4 and R5 may combine to form a ring.Type: GrantFiled: September 21, 2001Date of Patent: September 13, 2005Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
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Patent number: 6933405Abstract: The present invention is a user- and eco-friendly hypervalent iodine reagent (mIBX) capable of selectively oxidizing allylic and benzylic alcohols in water and other eco-friendly solvents and having generally the following structure: Allylic and benzylic alcohols are cleanly oxidized to the corresponding carbonyl compounds in water or water-THF mixtures, or other mixtures, using a water-soluble o-iodoxybenzoic acid derivative of the present invention.Type: GrantFiled: July 31, 2003Date of Patent: August 23, 2005Assignee: Board of Trustees of Western Illinois UniversityInventors: Thottumkara K. Vinod, Arun P. Thottumkara
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Patent number: 6875894Abstract: The invention relates to bis(alkylthio)carbenium salts of the formula I with the stated definitions for R1, R2, R3 and Y?, and to a process for the preparation thereof. The compounds according to the invention are advantageously suitable as electrophilic reagents for the transfer of fluorinated alkyl and acyl radicals onto nucleophilic compounds.Type: GrantFiled: February 11, 2002Date of Patent: April 5, 2005Assignee: Merck Patent GmbHInventors: Peer Kirsch, Andreas Ruhl, Gerd-Volker Röschenthaler, Dmitrii Sevenard
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Patent number: 6872855Abstract: The present invention is directed to a convenient method of synthesizing radiolabeled ?-trifluoromethyl ketones by a fluorination reaction. The present invention also relates to imaging agents and markers for identifying cell proliferation, or viral infection. The markers and imaging agents including the radiolabeled ?-trifluoromethyl ketones that are prepared by the present method.Type: GrantFiled: November 26, 2003Date of Patent: March 29, 2005Assignee: University of Southern CaliforniaInventors: G. K. Surya Prakash, Mian M. Alauddin, Jinbo Hu, Peter S. Conti, George A. Olah
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Patent number: 6855850Abstract: To provide a practical method of manufacturing fluorine compounds in a small number of steps that can carry out fluorination reaction of substrates using easily available fluorinating agents that can be inexpensively produced industrially, and recover precursors of the fluorinating agents generated accompanying the reaction quantitatively in an easy operation, and a method of recovery and regeneration of the precursors of the fluorinating agents. N-Fluoro-quaternary-nitrogen-onium tetrafluoroborate salts represented by the general formula (1) as the fluorinating agents are used. N-Hydro-quaternary-nitrogen-onium tetrafluoroborate salts represented by the general formula (2) generated accompanying the reaction are separated and recovered from the reaction mixture by means of depositing as crystals by the addition of solvents with a low affinity to the salts to the reaction mixture after the reaction.Type: GrantFiled: May 1, 2003Date of Patent: February 15, 2005Assignee: Daikin Industries Ltd.Inventors: Kenji Adachi, Ginjiro Tomizawa, Satoshi Oishi
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Patent number: 6849768Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity.Type: GrantFiled: October 7, 2003Date of Patent: February 1, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 6825383Abstract: The present invention provides a process for regiospecific chlorination of an aromatic or aliphatic compound with a chlorine source comprising a metal chloride and other than Cl2 and SO2Cl2 in presence of hypervalent iodine catalyst and in acidic medium.Type: GrantFiled: September 22, 2003Date of Patent: November 30, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Gajanan Kundalik Dewkar, Vinay Vijayraj Thakur, Sanjeevani Amrit Pardhy, Arumugam Sudalai, Sukumar Devotta
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Publication number: 20040230079Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“−CF2−”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.Type: ApplicationFiled: January 12, 2004Publication date: November 18, 2004Inventors: G.K.Surya Prakash, Jinbo Hu, George A. Olah
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Patent number: 6730814Abstract: This invention relates to a process for the preparation of acylated aromatic ethers, in particular the acylation of anisole (methoxybenzene) and veratrole (1,2-dimethoxybenzene) for the preparation of corresponding acylated aromatic ether, namely, p-methoxyacetophenone and 3,4-dimethoxyacetophenone respectively, using clay based heterogeneous catalysts, and their lanthanide exchanged forms at moderate temperature and pressure with high selectivity.Type: GrantFiled: January 14, 2003Date of Patent: May 4, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Rakesh Vir Jasra, Muthusamy Sengodagounder, Yogiraj Mansukhlal Badheka