Halogen Containing Reactant Patents (Class 568/364)
  • Patent number: 9928973
    Abstract: A dielectric insulation medium. The insulation medium is characterized in that it comprises a fluoroketone having from 4 to 12 carbon atoms.
    Type: Grant
    Filed: February 27, 2014
    Date of Patent: March 27, 2018
    Assignee: ABB Technology AG
    Inventors: Max-Steffen Claessens, Per Skarby
  • Publication number: 20140081038
    Abstract: The present invention relates to an apparatus comprising a) an unbaffled reactor or microreactor having a channel defined by a pathway, and b) an oscillating flow device, wherein the channel pathway comprises a plurality of directional changes. The reactor channel has a hydrolic diameter from 0.1 mm to 10 mm A method of making said apparatus and the use of said apparatus to carry out a process on a suspension is also disclosed.
    Type: Application
    Filed: January 13, 2011
    Publication date: March 20, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Rafael Wilhelmus Elisabeth Ghislain Reintjens, Mehul Thathagar
  • Patent number: 8067631
    Abstract: To provide a method of rapid methylation of alkenes, which is applicable to the preparation of a PET tracer and which enables alkenes to be methylated through cross coupling between SP2 (alkenyl) and SP3 (alkyl) carbon atoms rapidly and in a high yield. Methyl iodide and an alkenyltrialkylstannane are subjected to cross coupling in an aprotic polar solvent in the presence of a palladium complex having a valence of 0, a phosphine ligand, a cuprous halide, and a carbonate and/or alkali metal fluoride.
    Type: Grant
    Filed: October 6, 2006
    Date of Patent: November 29, 2011
    Assignee: Gifu University
    Inventors: Masaaki Suzuki, Takamitsu Hosoya
  • Patent number: 7078570
    Abstract: The present invention relates to substituted cyclohexenes, to their use as well as to their preparation method. These compounds have powerful long lasting natural fruity grapefruit notes with minty and fresh green tonalities.
    Type: Grant
    Filed: December 3, 2001
    Date of Patent: July 18, 2006
    Assignee: Givaudan SA
    Inventor: Andreas Goeke
  • Patent number: 6995291
    Abstract: The present invention relates to the field of organic synthesis and more precisely to a process for the synthesis of an unsaturated aldehyde or ketone by oxidation of the corresponding alcohol. The oxidation is performed by a hypochlorite salt and a catalytic amount of a N-(2,2,6,6-tetraalkyl-4-piperidinyl-N-oxyl)-2-amino-1,3,5-triazine compound, preferably a N-oxyl derivative of one of the polymers known under the trademark Chimassorb® 944 or 2020.
    Type: Grant
    Filed: September 22, 2003
    Date of Patent: February 7, 2006
    Assignee: Firmenich SA
    Inventor: Eric Walther
  • Patent number: 6969776
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: November 29, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6838582
    Abstract: A highly pure 2,4,4,6-tetrabromo-2,5-cyclohexadienone has been prepared in a single pot, eco-friendly procedure in yields of 91-94% from phenol. In this method, a mixture of alkali/alkaline earth metal bromide and alkali/alkaline earth metal bromate was employed as brominating agent in place of corrosive liquid bromine. The reaction between phenol and the brominating reagent was initiated by the action of a mineral acid or moderately strong organic acid. The crude product was further characterized by standard analytical and spectroscopic methods.
    Type: Grant
    Filed: December 31, 2002
    Date of Patent: January 4, 2005
    Assignee: Council of Scientific and Industrial Research
    Inventors: Ashutosh Vasant Bedekar, Ramachandraiah Gadde, Pushhpito Ghosh
  • Patent number: 6833481
    Abstract: Industrially advantageous processes for producing a 2-alkyl-2-cyclopentenone in high yields starting from a 2-(1-hydroxyalkyl)cyclopentanone or a 2-alkylidenecyclopentanone, which are obtainable from a cyclopentanone and a carbonyl compound. A 2-(1-hydroxyalkyl)cyclopentanone represented by the following general formula (1): (wherein R1, R2, R3, R4, R5, R6 and R7 each independently represents hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have one or more substituents or an aromatic group which may have one or more substituents, and each of (1) R6 or R7 with R3 and (2) R6 or R7 with R4 or R5 may be together combined to form a ring which may have a double bond) is subjected to dehydrative isomerization in the presence of a bromine compound and/or an iodine compound.
    Type: Grant
    Filed: November 29, 2002
    Date of Patent: December 21, 2004
    Assignee: Takasago International Corporation
    Inventors: Takeshi Yamamoto, Kenichiro Adachi, Shinya Watanabe, Hideo Ujihara, Toshimitsu Hagiwara
  • Patent number: 6803488
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: October 12, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6689917
    Abstract: The present invention provides a process for producing a linear perfluoroalkanone or a perfluorocycloalkanone, which comprises using as a starting material a combination of the same or different kinds of compounds that are selected from perfluoroalkanoyl halides represented by the formula: F(CF2)nCOX wherein X is F, Cl, Br or I and n is an integer of 1 to 8, or a perfluoroalkanedioyl dihalide represented by the formula: XOC(CF2)nCOX wherein X is F, Cl, Br or I and n is an integer of 3 to 8, and reacting the starting material with a metal carbonate or metal carbonates. According to the present invention, perfluoroalkanones can be produced with a good yield from relatively easily available starting materials by a simple synthesis method.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: February 10, 2004
    Assignee: Daikin Industries, Ltd.
    Inventors: Kouzou Noda, Hirokazu Aoyama
  • Patent number: 6476274
    Abstract: The invention relates to a process for preparing cyclobutanone by oxidizing cyclobutanol with an alkali metal hypochlorite or alkaline earth metal hypochlorite in the presence of an acid.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: November 5, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Knops, Bernd Gallenkamp, Lubbertus Mulder, Stefan Antons
  • Publication number: 20020055453
    Abstract: Lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones are grand fragrances with muscone note with which perfumes with new odor notes can be prepared.
    Type: Application
    Filed: August 2, 2001
    Publication date: May 9, 2002
    Inventors: Marcus Eh, Ingo Wohrle
  • Publication number: 20020016511
    Abstract: A first process for producing an optically active perfluoroalkylcarbinol derivative includes (a) reacting an optically active imine with a compound that is a hemiacetal of a perfluoroalkylaldehyde or a hydrate of a perfluoroalkylaldehyde to obtain a condensate; and (b) hydrolyzing the condensate under an acid condition. A second process for increasing optical purity of an optically active 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone derivative includes (a) precipitating a racemic crystal of the derivative, from the derivative; and (b) removing the racemic crystal from the derivative. A third process for increasing optical purity of the butanone derivative includes recrystallizing the derivative. Novel compounds are optically active and inactive 4,4,4-trifluoro-3-hydroxybutanoic aryl ester derivatives.
    Type: Application
    Filed: January 29, 2001
    Publication date: February 7, 2002
    Inventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
  • Patent number: 6313352
    Abstract: The present invention provides a process for producing canthaxanthin by mixing &bgr;-carotene with an alkali metal chlorate or an alkali metal bromate in water and an organic solvent immiscible with water; adding an iodine halide or iodide; and adding a metal iodide whereby the &bgr;-carotene is oxidized to yield canthaxanthin.
    Type: Grant
    Filed: June 9, 2000
    Date of Patent: November 6, 2001
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshiki Mori, Naoyuki Katayama, Tsuyoshi Kajiyashiki, Masahiko Kitayama
  • Patent number: 6215028
    Abstract: The invention relates to a process for the preparation of cyclohexanones from the corresponding phenols by partial hydrogenation, characterized in that the reaction mixture obtained by means of the hydrogenation is treated with sulfonating agents before the isolation of the cyclohexanone.
    Type: Grant
    Filed: November 2, 1998
    Date of Patent: April 10, 2001
    Assignee: Merck Patent Gesellschaft mit
    Inventors: Bernd Oster, Peter Mackert, Detlef Pauluth, Markus Wydra
  • Patent number: 6207864
    Abstract: The invention relates to a process for the halogenation of cyclopropylmethyl ketone with at least one dihalo-triorganophosphorane of the general formula I R3PHal2   (I), in which the radicals R can be the same or different and denote a saturated or unsaturated aliphatic C1-C20 hydrocarbon radical, a phenyl or (C1-C4 alkyl)phenyl radical, which may be optionally substituted by one or two fluorine, chlorine and/or nitro groups, P stands for phosphorus and Hal denotes chlorine, bromine, or iodine, at a temperature of from 800° to 130° C.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: March 27, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Henningsen, Armin Stamm, Martin Fischer, Wolfgang Siegel
  • Patent number: 5420356
    Abstract: A process for producing cyclobutanones with industrial advantage is provided which comprises contacting an .alpha.-haloacetyl halide with an ethylenic unsaturated compound in the presence of a dehydrohalogenating agent and a Lewis acid.
    Type: Grant
    Filed: March 24, 1994
    Date of Patent: May 30, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Yoshinori Nakayama
  • Patent number: 5332847
    Abstract: A process is disclosed for the preparation of 21-bromo-4-pregnene-3,20-dione derivatives of general Formula I ##STR1## wherein R.sub.1 is a hydrogen atom, a hydroxy group or an alkanoyl group of up to 6 carbon atoms,R.sub.2 symbolizes a hydrogen atom or a methyl group, or whereinR.sub.1 and R.sub.2 jointly mean an isopropylidenedioxy group,whereinR.sub.3 is a hydrogen atom, a fluorine atom or a methyl group,V is a methylene group or ethylene group,X is a hydrogen atom, a fluorine atom or a chlorine atom, andY is a methylene group, a hydroxymethylene group or a carbonyl group.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: July 26, 1994
    Assignee: Schering Aktiengesellschaft
    Inventor: Gerhard Hempel, deceased
  • Patent number: 5288915
    Abstract: Ketones are prepared by admixing at least one gem-dichloro compound with at least one acid such that the ketone wherein the keto-oxygen replaces the gem-dichloro group is formed. The reaction is exemplified by the reaction of 9,9-dichlorofluorene with an acid such that fluorenone is formed. This process has the advantage that no oxidizing agent is used.
    Type: Grant
    Filed: December 17, 1992
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventor: Marlin E. Walters
  • Patent number: 5258547
    Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: Gary N. Sheldrake
  • Patent number: 5086178
    Abstract: Fluorinated diazabicycloalkane derivative of the following Formula I: ##STR1## wherein n represents 0, 1 or 2; R represents a quaternizing organic group; each R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, C.sub.1 -C.sub.6 alkyl-substituted aryl or aryl-substituted C.sub.1 -C.sub.6 alkyl and each X.sup.- independently represents a conterion or 2X.sup.- represents a single divalent counterion, are electrophilic fluorinating agents.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: February 4, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Ronald E. Banks
  • Patent number: 4983776
    Abstract: The invention relates to the synthesis of functional fluoro derivatives and more particularly that of perfluorinated aldehydes of the type R.sub.F -CHO where R.sub.F denotes a linear or branched perfluoroalkyl radical.A perfluoroalkyl iodide R.sub.F I is reacted over the zinc-copper metal couple, in the presence of a radical initiator, with an amide RCONR.sub.1 R.sub.2, R denoting a hydrogen atom or a methyl or ethyl radical, and each of R.sub.1 and R.sub.2 denoting a C.sub.1 -C.sub.4 alkyl radical.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: January 8, 1991
    Assignee: Societe Atochem
    Inventors: Sylvie Benefice-Malouet, Hubert Blancou, Auguste Commeyras
  • Patent number: 4983774
    Abstract: The preparation of ketones by reacting an acylating agent with an organo-manganous compound is catalyzed by a copper compound.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 8, 1991
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Gerard Cahiez, Blandine Laboue, Pierre Tozzolino
  • Patent number: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4846945
    Abstract: Oxidation of alcohols to ketones using bromine suffers from a side reaction of comparable speed in which a bromide substituted product is formed. Additionally, the use of bromine as reagent is relatively unpleasant and it creates a major waste disposal problem.The latter problem can be solved by generating bromine in situ by reaction between hydrogen peroxide and bromide ions or hydrogen bromide, but this inevitably increases the exposure of the alcohol to HBr/Br.sup.-. The selectivity of the process towards non-substituted oxidation depending upon the inherent deactivation or reactivity of the alcohol can be improved by irradiating the reactants with light of suitable frequency to generate bromine radicals in the mixture, and/or by controlling the rate of introduction of the hydrogen peroxide and controlling the extent to which mole ratio of HBr:alcohol is substoichiometric.
    Type: Grant
    Filed: September 2, 1987
    Date of Patent: July 11, 1989
    Assignee: Interox Chemicals Limited
    Inventors: Philip J. Turner, Vincent I. Routledge, Martin Jeff
  • Patent number: 4827044
    Abstract: Process of preparation of ketones by the reaction of an organo-metallic compound with a compound carrying a carbonyl, within a solvent, in the presence of a manganous salt as catalyst. The manganous salt is in the form of a double salt of Mn and an alkali metal cation.
    Type: Grant
    Filed: March 8, 1988
    Date of Patent: May 2, 1989
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Pierre Tozzolino, Gerard Cahiez
  • Patent number: 4691052
    Abstract: Pyrethroid acids are prepared by conducting a cycloaddition reaction of a conjugated diene and a dihaloketene to form a dihalo-vinylcyclobutanone product; reducing the dihalo-vinylcyclobutanone product to a monohalo-vinylcyclobutanone product and then conducting a ring contraction with a base to form the desired acid product.
    Type: Grant
    Filed: May 30, 1986
    Date of Patent: September 1, 1987
    Assignee: S.C. Johnson & Son, Inc.
    Inventors: William T. Brady, Scott J. Norton, Jinrea Ko
  • Patent number: 4582941
    Abstract: A process for producing squaric acid comprises reacting hexachlorocyclobutene, or its mixtures with hexachlorobutadiene, with 96-100% sulfuric acid, at 80.degree.-150.degree. C., and adding at least the stoichiometric amount of water required for the hydrolysis, while maintaining the acid concentration between 96% and 100% throughout the reaction.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: April 15, 1986
    Assignee: Huels Aktiengesellschaft
    Inventors: Konrad Rombusch, Gunther Maahs
  • Patent number: 4529813
    Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.
    Type: Grant
    Filed: March 14, 1980
    Date of Patent: July 16, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Heine, Willy Hartmann
  • Patent number: 4524221
    Abstract: Process for the production of an acyloin comprising the steps of:A. reacting a Grignard reagent with silylated cyanohydrin,B. treating the reaction product of step A with aqueous acid, andC. recovering the resulting acyloin.Acyloins thus formed are useful as photoinitiators for initiation of free radical polymerization reactions.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: June 18, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
  • Patent number: 4359586
    Abstract: 2-Hydroxy-3-methylcyclopent-2-en-1-one was synthesized in a five-step synthesis starting from 2-methyl-1,3-butadiene. Novel intermediate steps include the hot tube isomerization of 1,1-dihalo-2-methyl-2-vinylcyclopropane to give 1-methyl-4,4-dihalocyclopent-1-ene, hydrolysis to 3-methyl-2-cyclopenten-1-one, epoxidation of the latter using a phase transfer catalyst, followed by catalyzed isomerization to produce 2-hydroxy-3-methylcyclopent-2-en-1-one in high overall yield.
    Type: Grant
    Filed: February 12, 1981
    Date of Patent: November 16, 1982
    Assignee: SCM Corporation
    Inventors: Tse-Lok Ho, Shing-Hou Liu
  • Patent number: 4296258
    Abstract: New process for the preparation of acetylenic macrocyclic ketones, which compounds represent useful intermediates for the synthesis of valuable perfuming ingredients, viz. muscone and EXALTONE.RTM. (cyclopentadecanone).
    Type: Grant
    Filed: December 28, 1979
    Date of Patent: October 20, 1981
    Assignee: Firmenich SA
    Inventors: Charles Fehr, Gunther Ohloff, Georges H. Buchi
  • Patent number: 4284821
    Abstract: Dichlorovinylcyclobutanones of the formula ##STR1## wherein one of R.sub.1 and R.sub.2 is methyl and the other is hydrogen or methyl, or R.sub.1 and R.sub.2 together are alkylene having 2-4 C atoms, X is chlorine and Y is hydrogen, or X is hydrogen and Y is chlorine; processes for preparing them, and their use as intermediates for producing pesticidal compositions.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: August 18, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Daniel Bellus
  • Patent number: 4272633
    Abstract: A process for preparing tetrachlorocyclobutenone from hexachlorocyclobutene comprises reacting (a) hexachlorocyclobutene withI. (b) anhydrous sulphuric acid and (c) sulphur trioxide; orII. (b) anhydrous sulphuric acid and (d) phosphorus pentoxideat a temperature of 30.degree.-140.degree. C.;the starting materials being present in the following molar ratios at the start of the reaction:for I,(a):(c)=0.67-10, and(b):(c)=0.1-10;and for II,(a):(d)=0.67-10 and(b):(d)=0.5-20.
    Type: Grant
    Filed: March 9, 1979
    Date of Patent: June 9, 1981
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventors: Gunther Maahs, Konrad Rombusch
  • Patent number: 4242278
    Abstract: A process for the preparation of 2-(2',2',2',-trihalogenoethyl)-4-halogenocyclobutan-1-ones of the formula ##STR1## in which one of the radicals R.sub.1 and R.sub.2 is methyl and the other is hydrogen or methyl, or R.sub.1 and R.sub.2 together are an alkylene group having 2 to 4 carbon atoms, and X and Y are each chlorine or bromine, comprising reacting a 2,4,4,4-tetrahalogenobutyric acid chloride in the presence of an organic base with an ethylene compound which is disubstituted in 1-position by the radicals R.sub.1 and R.sub.
    Type: Grant
    Filed: October 3, 1978
    Date of Patent: December 30, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Hans Greuter, Eginhard Steiner, Daniel Bellus
  • Patent number: 4216172
    Abstract: A process for the preparation of a cyclobutanone of the formula ##STR1## in which R.sup.1 to R.sup.6 each independently is a hydrogen, halogen, cyano, alkoxy, alkoxycarbonyl, carboxamido, dialkylphosphono, alkyl, cycloalkyl, aryl, aralkyl or alkenyl radical, or two of them together with the carbon atom to which each is linked form a ring,comprising reacting an N,N-disubstituted carboxylic acid amide of the formula ##STR2## in which R.sup.7 and R.sup.8 each independently is an alkyl, cycloalkyl, alkenyl, aryl or aralkyl radical or together form a ring, with an inorganic acid halide, and then reacting the product with a tertiary amine, an olefin of the formula ##STR3## and a Lewis acid, and subsequently hydrolyzing the mass. Preferably isobutyric acid dimethylamide is employed as the carboxylic acid amide, phosgene is employed as the inorganic acid halide, triethylamine is employed as the tertiary amine and zinc chloride or titanium tetrachloride is employed as the Lewis acid.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: August 5, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Heine, Willy Hartmann
  • Patent number: 4212827
    Abstract: Process for the manufacture of canthaxanthin by oxidizing .beta.-carotene, retro-dehydro-carotene or echinenone with a salt of chloric or bromic acid in the presence of a catalyst and of an inert diluent or solvent.
    Type: Grant
    Filed: October 13, 1977
    Date of Patent: July 15, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Paust, Joachim Schneider, Hagen Jaedicke