Halogen In Acid Moiety Patents (Class 560/226)
  • Patent number: 11905177
    Abstract: The invention relates to a storage medium and to a method for using a storage medium based on ionic compounds, which can reversibly absorb and store chlorine and chlorine from process gases, and which can release the same again by changing the ambient conditions, wherein the storage medium can be reused for this task after discharge.
    Type: Grant
    Filed: May 3, 2019
    Date of Patent: February 20, 2024
    Assignee: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
    Inventors: Maxime Paven, Yuliya Schiesser, Rainer Weber, Gerhard Langstein, Vinh Trieu, Sebastian Hasenstab-Riedel, Nico Schwarze, Simon Steinhauer
  • Patent number: 10538474
    Abstract: A method has been disclosed of obtaining high purity, colourless monochloroacetic acid encompassing the chlorination of acetic acid with chlorine in the presence of a catalyst, followed by the recovery of the catalyst through vacuum distillation and purification of the obtained liquid raw product by its hydrodehalogenation by hydrogen in the presence of a palladium catalyst and then vacuum distillation.
    Type: Grant
    Filed: February 4, 2017
    Date of Patent: January 21, 2020
    Assignee: PCC MCAA SP. Z O. O.
    Inventor: Bartosz Bankowski
  • Patent number: 10196488
    Abstract: The invention relates to a crosslinkable composition X, comprising: at least one organopolysiloxane compound A comprising, per molecule, at least two C2-C6 alkenyl radicals bonded to silicon atoms; at least one organohydrogenopolysiloxane compound B comprising, per molecule, at least two hydrogen atoms bonded to an identical or different silicon atom; at least one catalyst C which is a complex corresponding to the following formula: [Co (L1)2] in which: the symbol Co represents cobalt at degree of oxidation II; the symbols L1, which may be identical or different, represent a ligand which is a ?-dicarbonylato anion or the enolate anion of a ?-dicarbonylated compound; optionally at least one adhesion promoter D; and optionally at least one filler E.
    Type: Grant
    Filed: November 6, 2015
    Date of Patent: February 5, 2019
    Assignees: ELKEM SILICONES FRANCE SAS, UNIVERSITE CLAUDE BERNARD LYON 1, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
    Inventors: Vincent Monteil, Jean Raynaud, Delphine Crozet, Magali Bousquié, Sébastien Marrot
  • Patent number: 8809451
    Abstract: According to the present invention, a polymer is obtained by polycondensation of a fluorinated dicarboxylic acid derivative of the general formula (M-1) or an acid anhydride of the fluorinated dicarboxylic acid with a polyfunctional compound having two to four reactive groups corresponding in reactivity to carbonyl moieties of the fluorinated dicarboxylic acid derivative or acid anhydride. [Chem. 134] AOCF2C-Q-CF2COA???(M-1) In the above formula, Q represents a divalent organic group having a substituted or unsubstituted aromatic ring; and A and A? each independently represent an organic group. This polymer exhibits a sufficiently low dielectric constant for use as a semiconductor protection film and has the capability of forming a film at a relatively low temperature of 250° C. or lower.
    Type: Grant
    Filed: February 18, 2010
    Date of Patent: August 19, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Yoshimi Isono, Satoru Narizuka, Hidehisa Nanai, Kazuhiro Yamanaka
  • Publication number: 20140212980
    Abstract: The present invention provides a probe that further promotes ionization in proteomic analysis using mass spectrometry, and a high-sensitive mass spectrometry method for a protein using such a probe. Further, the present invention provides an ionization-enhancing probe that can be used even for a protein that has a high degree of hydrophobicity and quickly turns over, and a high-sensitive mass spectrometry method for a protein using such a probe. A thiol probe for a protein, which is represented by the following formula (I): [Chemical Formula 1] wherein R1 represents a linker group, and R2 represents a substituted ammonium group or a substituted amino group. A mass spectrometry method for a protein, comprising the steps of: obtaining a modified protein by reacting the thiol probe with a protein to be subjected to mass spectrometry; and subjecting the modified protein to mass spectrometry.
    Type: Application
    Filed: August 17, 2012
    Publication date: July 31, 2014
    Inventors: Takashi Shimada, Taka-Aki Sato, Koichi Tanaka
  • Patent number: 8653131
    Abstract: The present invention relates to polymeric derivatives, which can be conjugated to an amino-containing drug to improve its in vivo properties. The polymeric derivative can subsequently be released to yield the drug in its native form. Methods of preparing and using these polymeric derivatives and drug conjugates are described.
    Type: Grant
    Filed: August 21, 2009
    Date of Patent: February 18, 2014
    Assignees: Baxter Healthcare S.A., Baxter International Inc.
    Inventors: Guohan Yang, Ton That Hai, Bennett P. Melnick, Paul Sanders, Cong Jiang, Catherine Quinn, Jie Li, Arounaguiry Ambroise, Larry R. Brown
  • Publication number: 20130131375
    Abstract: A process for preparing difluoroacetic acid, salts thereof or esters thereof is described. The process can further include preparation of difluoroacetic acid, salts thereof or esters thereof, wherein the reaction occurs in the presence of water of a salt providing a fluoride anion and of monohalogenated or dihalogenated acetic acid, in acid, salified or esterified form, at least one halogen atom being other than the fluorine atom.
    Type: Application
    Filed: July 26, 2011
    Publication date: May 23, 2013
    Applicant: RHODIA OPERATIONS
    Inventor: Olivier Buisine
  • Patent number: 8318964
    Abstract: Problem To provide an environmentally-friendly method for producing industrially an ester compound. Solution The present invention is a method for producing an ester compound which comprises subjecting a carboxylic acid and an alcohol to dehydration-condensation reaction using an involatile acid catalyst and then removing the residual acid catalyst by bringing a weak basic substance into contact with the residual acid catalyst.
    Type: Grant
    Filed: October 20, 2007
    Date of Patent: November 27, 2012
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Shigeaki Imazeki, Ryohiko Kinoshita
  • Patent number: 8293948
    Abstract: A reagent for organic synthesis with which a chemical reaction can be conducted in a liquid phase and unnecessary compound(s) can be easily separated at low cost from the liquid phase after completion of the reaction. The reagent for organic synthesis reversibly changes from a liquid-phase state to a solid-phase state with changes in solution composition and/or solution temperature, and is for use in organic synthesis reactions. This reagent for organic syntheses facilitates process development. With the reagent, research on and development of, e.g., medicines through, e.g., compound library synthesis, etc. can be accelerated. It can hence contribute to technical innovations in the biochemical industry and chemical industry.
    Type: Grant
    Filed: January 9, 2012
    Date of Patent: October 23, 2012
    Assignee: Jitsubo Co., Ltd.
    Inventors: Kazuhiro Chiba, Shokaku Kim, Yusuke Kono
  • Patent number: 8273914
    Abstract: Disclosed is a process for making vinyl chloroformate which includes reacting (a) a carbonyl compound of formula I: wherein R is a halogen or an alkyl group of 1 to about 25 carbon atoms; with (b) a silyl-containing enol ether and in the presence of an effective amount of a Group VIII-containing catalyst.
    Type: Grant
    Filed: June 27, 2011
    Date of Patent: September 25, 2012
    Assignee: Bausch & Lomb Incorporated
    Inventors: Ivan M. Nunez, David E. Seelye
  • Patent number: 8273837
    Abstract: A radiation-sensitive resin composition which has high transparency to radiation, excelling in basic properties as a resist such as sensitivity, resolution, and pattern shape, and, in particular, exhibiting high resolution performance, excellent DOF and LER, and high resistance to a liquid medium used in liquid immersion lithography is provided. Also provided are a polymer which can be used in the composition, a novel compound useful for synthesizing the polymer, and a method of producing the composition.
    Type: Grant
    Filed: December 13, 2006
    Date of Patent: September 25, 2012
    Assignee: JSR Corporation
    Inventors: Tomoki Nagai, Takuma Ebata, Nobuji Matsumura
  • Publication number: 20100324314
    Abstract: PROBLEM To provide an environmentally-friendly method for producing industrially an ester compound. SOLUTION The present invention is a method for producing an ester compound which comprises subjecting a carboxylic acid and an alcohol to dehydration-condensation reaction using an involatile acid catalyst and then removing the residual acid catalyst by bringing a weak basic substance into contact with the residual acid catalyst.
    Type: Application
    Filed: October 20, 2007
    Publication date: December 23, 2010
    Applicant: WAKO PURE CHEMICAL INDUSTRIES, LTD.
    Inventors: Shigeaki Imazeki, Ryohiko Kinoshita
  • Publication number: 20100324139
    Abstract: The present invention relates to a novel method for the preparation of racemic pregabalin (1) or a single enantiomer thereof, (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid (2).
    Type: Application
    Filed: December 19, 2008
    Publication date: December 23, 2010
    Applicants: Generics [UK] Limited, Mylan India Private Limted
    Inventors: Abhay Gaitonde, Debashish Datta, Bindu Manojkumar, Sunanda Phadtare
  • Publication number: 20100144671
    Abstract: Bromoacetoxycalcidiol (B3CD), which is structurally related to calcidiol, exhibits cytotoxic and apoptotic activity toward cancer cells, including highly aggressive neuroblastoma cells. A series of small molecules designed around the structure of B3CD is expected to have growth inhibitory and apoptogenic activities toward a wide range of malignancies. B3CD shows no apparent toxicity in vivo, indicating potential value as a chemotherapeutic agent which will be particularly useful in treating highly aggressive tumors.
    Type: Application
    Filed: March 3, 2006
    Publication date: June 10, 2010
    Applicant: Women and Infants Hospital of RI, Inc.
    Inventors: Narasimha Swamy, Hema Malini K. Sundaresha
  • Publication number: 20100048483
    Abstract: The present invention relates to polymeric derivatives, which can be conjugated to an amino-containing drug to improve its in vivo properties. The polymeric derivative can subsequently be released to yield the drug in its native form. Methods of preparing and using these polymeric derivatives and drug conjugates are described.
    Type: Application
    Filed: August 21, 2009
    Publication date: February 25, 2010
    Applicants: BAXTER HEALTHCARE S.A., BAXTER INTERNATIONAL INC.
    Inventors: Guohan Yang, Ton T. Hai, Bennett Melnick, Paul Sanders, Cong Jiang, Catherine Quinn, Jie Li, Arounaguiry Ambroise, Larry R. Brown
  • Patent number: 7579498
    Abstract: A process for preparing fluorinated alkyl carboxylate esters comprises reaction of a silver carboxylate or silver carboxylate precursor, such as silver (I) iodide with a fluorinated alkyl iodide and a carboxylic acid. Preferably the fluorinated alkyl iodide has the general formula CF3(CF2)nCH2CH2I, wherein n is an integer in the range of from 1 to 29 and the carboxylic acid is acetic acid, acrylic acid or methacrylic acid.
    Type: Grant
    Filed: November 29, 2005
    Date of Patent: August 25, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Allen Andrews, Alexander Borisovich Shtarov, Joseph Norman Hockman
  • Publication number: 20090143604
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol.
    Type: Application
    Filed: November 20, 2008
    Publication date: June 4, 2009
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Publication number: 20090028791
    Abstract: A compound having structure I: wherein xC is selected from the group consisting of 11C, 12C, and 13C; R is selected from the group consisting of —OH, —O?R4+ wherein R4 is selected from the group consisting of Na and K, —OR3 wherein R3 is selected from the group consisting of C1-8 alkyl and C1-8 alkenyl, —NH2, and NHR3; R? is selected from the group consisting of —H, —Cl, —F, —Br, and —I; R? is selected from the group consisting of —H, —Cl, —F, —Br, and —I; and R?? is selected from the group consisting of —H, —Cl, —F, —Br, —I, 18F, 19F, 75Br, 76Br, 77Br, 123I, 124I, and 131I; provided, when xC is 12C, R?? is selected from the group consisting of 18F, 19F, 75Br, 76Br, 77Br, 123I, 124I, and 131I.
    Type: Application
    Filed: July 24, 2008
    Publication date: January 29, 2009
    Inventors: Julius A. Balatoni, Louis R. DePalatis, William Tong, Juri Gelovani
  • Patent number: 7425646
    Abstract: A compound represented by the formula AF(—COF)n, provided that AF and n have the following meanings. AF: a fluorinated adamantane residue which is an n-valent group having an n number of hydrogen atoms removed from adamantane (provided that when n is at least 2, the removed hydrogen atoms are hydrogen atoms bonded to different carbon atoms), wherein at least one of the remaining hydrogen atoms is substituted by a fluorine atom, and the remaining hydrogen atoms may be substituted by a C1-6 alkyl group or fluoroalkyl group, and n: an integer of from 1 to 4, provided the when n is 1, AF has at least one hydrogen atom.
    Type: Grant
    Filed: December 15, 2006
    Date of Patent: September 16, 2008
    Assignee: Asahi Glass Company, Limited
    Inventors: Kazuya Oharu, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Masahiro Ito
  • Patent number: 7423170
    Abstract: Oncoproteins such as Ras and RhoB are known to induce cell division in an unrestrained manner when such proteins are localized at the inner surface of a cancer cell membrane. The localization is effected by the prenylation reaction, whereby a hydrophobic group (e.g. a farnesyl group) is attached to the protein in the presence of an enzyme (e.g. farnesyl protein transferase). Deactivation of the prenylation enzyme through covalent modification can therefore ultimately result in the mitigation and/or cessation of cancer cell growth. Various prenylation inhibitors having the necessary structural groups to bond covalently, or essentially irreversibly, to the prenylation enzyme include carbonyl or thiocarbonyl compounds (or masked versions of these compounds) and alpha oxo-epoxides bonded to a hydrophobic, substrate-mimicking group. The carbonyl or thiocarbonyl compounds also contain a nucleofugal atom or group to enhance the tendency to form covalent bonds.
    Type: Grant
    Filed: January 23, 2006
    Date of Patent: September 9, 2008
    Assignee: Arizona Biomedical Research Commission
    Inventors: Seth D. Rose, Scott R. Lefler, Steven R. Ottersberg, Ann Y. Kim, Karl J. Okolotowicz, Rosemarie F. Hartman
  • Patent number: 7345192
    Abstract: Compositions including a conjugate of ?-difluoromethylornithine can be applied topically to reduce hair growth.
    Type: Grant
    Filed: November 10, 2005
    Date of Patent: March 18, 2008
    Assignee: The Gillette Company
    Inventors: Anwar Jardien, Roman Rariy, Gurpreet S. Ahluwalia, Douglas Shander
  • Patent number: 7307185
    Abstract: The present invention provides a process for producing an optically active fluoro compound represented by formula (3) through reaction between a specific fluoroamine and an optically active diol; and a process for producing an optically active fluoroalcohol through hydrolysis of the optically active fluoro compound. According to the process of the present invention, such optically active fluoro compounds and optically active fluoroalcohols can be produced at high optical purity and high yield in a simple manner.
    Type: Grant
    Filed: March 2, 2005
    Date of Patent: December 11, 2007
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shoji Hara, Tsuyoshi Fukuhara
  • Patent number: 7053238
    Abstract: A fluorinated polyvalent carbonyl compound is produced by an economically advantageous method from inexpensive materials without requiring a complicated synthetic process step. Namely, the present invention comprises reacting a polyvalent alcohol having at least two kinds of alcohol skeletons selected among a primary alcohol, a secondary alcohol and a tertiary alcohol, with an acid halide to obtain a polyvalent ester compound, fluorinating it in a liquid phase to obtain a perfluorinated polyvalent ester compound, and cleaving the ester bonds derived from primary and secondary alcohols in the perfluoropolyvalent ester compound to obtain a fluorinated polyvalent carbonyl compound.
    Type: Grant
    Filed: July 15, 2004
    Date of Patent: May 30, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Daisuke Shirakawa, Masahiro Ito, Shin Tatematsu
  • Patent number: 7034179
    Abstract: The present invention provides a method for producing industrially useful fluorine-containing compounds such as a fluorinated ester compound and an acid fluoride compound. Namely, the present invention resides in a method for producing a fluorinated ester compound, which comprises fluorinating an ester compound which is an ester of a compound having hydroxyl group(s) with a compound having acyl fluoride group(s) and which has a structure which can be fluorinated, in a liquid phase to produce a fluorinated ester compound, wherein the fluorination is carried out in the form of a liquid mixture of the ester compound and the compound having acyl fluoride group(s).
    Type: Grant
    Filed: March 27, 2003
    Date of Patent: April 25, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Koichi Yanase, Yasuhiro Suzuki, Daisuke Shirakawa
  • Patent number: 7019163
    Abstract: The present invention relates to a method for producing a perfluorovinylcarboxylic acid ester by reacting a perfluorovinylcarboxylic acid salt with an alkylating agent. The present invention provides a method to produce perfluorovinylcarboxylic acid ester, which is used as a raw material of an ion-exchange membrane for the chloro alkali process, in high yield from starting material, a compound which can be easily produced, in a simple manner.
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: March 28, 2006
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Nobuyuki Uematsu, Masanori Ikeda
  • Patent number: 7015349
    Abstract: Compositions including a conjugate of ?-difluoromethylornithine can be applied topically to reduce hair growth.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: March 21, 2006
    Assignee: The Gillette Company
    Inventors: Anwar Jardien, Roman Rariy, Gurpreet S. Ahluwalia, Douglas Shander
  • Patent number: 6903233
    Abstract: A process for producing an optically active 3-azide-carboxylic acid ester by reacting an optically active 3-hydroxycarboxylic acid ester and a thionyl halide in the presence of a basic substance in an organic solvent to produce an optically active 3-halogenocarboxylic acid ester which is then reacted with an azide salt represented by the formula: MN3 (wherein M is an alkaline metal) in water or a mixture of water and a water soluble organic solvent.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: June 7, 2005
    Assignee: Takasago International Corporation
    Inventors: Akira Amano, Daisuke Igarashi, Takashi Miura
  • Patent number: 6858748
    Abstract: The novel compound of the disclosure is 4-chloro-4-(4-ethoxy-phenyl)-2-(fluoren-9-ylidene-hydrazono)-but-3-enoic acid methyl ester (3F-19), and it alone or in combination with 4-(4-Ethoxy-phenyl)-2-(N?-fluoren-9-ylidene-hydrazino)-2-hydroxy-4-oxo-butyric acid methyl ester (OF-13), appears useful in humans as therapeutic means for the eradication of tumors from the human's colon.
    Type: Grant
    Filed: January 13, 2004
    Date of Patent: February 22, 2005
    Assignee: Research Foundation of the University of Central Florida
    Inventors: D. Howard Miles, Solodnikov Sergey Yurjevich, Krasnykh Olga Petrovna, Lisovskaja Natalja Anatoljevna, Elena A. Goun
  • Patent number: 6858752
    Abstract: A fluorinated polyvalent carbonyl compound is produced by an economically advantageous method from inexpensive materials without requiring a complicated synthetic process step. Namely, the present invention comprises reacting a polyvalent alcohol having at least two kinds of alcohol skeletons selected among a primary alcohol, a secondary alcohol and a tertiary alcohol, with an acid halide to obtain a polyvalent ester compound, fluorinating it in a liquid phase to obtain a perfluorinated polyvalent ester compound, and cleaving the ester bonds derived from primary and secondary alcohols in the perfluoropolyvalent ester compound to obtain a fluorinated polyvalent carbonyl compound.
    Type: Grant
    Filed: March 27, 2003
    Date of Patent: February 22, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Daisuke Shirakawa, Masahiro Ito, Shin Tatematsu
  • Patent number: 6833468
    Abstract: A first process for producing an optically active perfluoroalklylcarbinol 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-hydroxybotanoic aryl ester derivatives.
    Type: Grant
    Filed: July 26, 2002
    Date of Patent: December 21, 2004
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
  • Patent number: 6720447
    Abstract: The present invention relates to a novel process for the preparation of esters of the general formula I from compounds of the general formula II contained in aqueous solutions which comprises a) extracting the compounds of the general formula II directly or after liberation from their salts in the presence of a C1-C8-alcohol and a water-immiscible solvent and b) then esterifying with the C1-C8-alcohol in the presence of a catalyst and of an entraining agent under the conditions of an azeotropic distillation, where the process steps (a) and (b) can be carried out separately in terms of time and space or else in a successive continuous or batchwise sequence and where the variables and substituents in the formulae I and II have the following meanings: R1=F, Cl, —OH, —OC1-C10-alkyl, R2=H, C1-C10-alkyl; R3=C1-C8-alkyl, Q=—OH, —O−K+, where K+ is an alkali metal cation or alkaline earth metal cation, n&equ
    Type: Grant
    Filed: July 17, 2001
    Date of Patent: April 13, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ditrich, Ulrich Block
  • Patent number: 6703520
    Abstract: The present invention provides a process for preparing a desired halogenated ester, which process comprises the steps of: (a) contacting (A) a substantially organic solvent free liquid mixture of (i) an alkanolate of the formula M—O—Z, wherein M is an alkali or alkaline earth metal, and Z is a linear, branched or cyclic alkyl group of 1 to 10 carbon atoms and (ii) a diester with (B) a halogenated ethylenically unsaturated olefin at a temperature of not more than 40° C. and with a mol ratio of halogenated ethylenically unsaturated olefin to alkanolate of not more than 1.1; (b) contacting an acid with a thus obtained reaction mixture thereby obtaining a mixture comprising the desired halogenated ester; and (c) recovering the halogenated ester from said reaction mixture.
    Type: Grant
    Filed: April 5, 2002
    Date of Patent: March 9, 2004
    Assignee: 3M Innovative Properties Company
    Inventors: Klaus Hintzer, Egon Obermaier, Werner Schwertfeger
  • Patent number: 6642409
    Abstract: A first process for producing an optically active perfluoroalklylcarbinol derivative includes (a) reacting an optically active imine with a compound that is a hemiacetal of a perfluoroalkylaldehyde or a hydrate of a perfinoroalkylaldehyde 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-hydroxybotanoic aryl ester derivatives.
    Type: Grant
    Filed: January 29, 2001
    Date of Patent: November 4, 2003
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
  • Patent number: 6639100
    Abstract: A process for producing an optically active perfluoroalkylcarbinol by reacting an optically active imine with a hemiacetal or hydrate of a perfluoroalkylaldehyde to obtain a condensate, and hydrolyzing the condensate under acidic conditions. Optical purity of optically active 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone compounds may be increased by precipitating and removing a racemic crystal, and also recrystallizing the compound. Novel compounds include optically active and inactive 4,4,4-trifluoro-3-hydroxybutanoic aryl esters. A process for producing optically active or incactive 4,4,4-trifluoro-3-hydroxybutyric acid aryl esters includes oxidizing an optically active or inactive 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone. Optical purity of optically active aryl esters may be increased by recrystallization. Optically active 4,4,4-trifluoro-1,3-butanediol may be produced by reducing the optically active aryl ester with a hydride.
    Type: Grant
    Filed: August 7, 2002
    Date of Patent: October 28, 2003
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
  • Patent number: 6583313
    Abstract: The methyl and ethyl esters of trifluoroacetic acid or chlorodifluoroacetic acid can be prepared in a technically simple manner from the corresponding acid chlorides and methanol or ethanol, respectively, in the presence of an “onium” salt of the acid as a catalyst. The alcohol is used in a stoichiometric excess, namely the molar ratio of alcohol to acid chloride is selected such that operation is in the region of a two-phase reaction. One of the phases is formed by the desired ester product, which is obtained in a high purity without any distillation.
    Type: Grant
    Filed: July 10, 1998
    Date of Patent: June 24, 2003
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Kerstin Eichholz, Werner Rudolph
  • Patent number: 6552217
    Abstract: Disclosed is a 4-step process for the preparation of alkyl esters of 1-methylcyclopropanecarboxylic acid which comprises the steps of (1) converting &ggr;-butyrolactone to &agr;-methyl-&ggr;-butyrolactone; (2) converting the &agr;-methyl-&ggr;-butyrolactone from step (1) to an alkyl 4-halo-2-methylbutyrate; (3) producing a xylene solution of the alkyl 4-halo-2-methylbutyrate; and (4) contacting the xylene solution of an alkyl 4-halo-2-methylbutyrate from step (3) with an alkali metal alkoxide under conditions of temperature and pressure which causes vaporization of (i) an alkanol as it is formed and (ii) an alkyl 1-methylcyclopropanecarboxylate as it is formed from the alkyl 4-halo-2-methylbutyrate. Also disclosed are processes whereby the alkyl 1-methylcyclopropanecarboxylate, prepared as described above, is converted to 1-methylcyclopropylamine.
    Type: Grant
    Filed: July 2, 2001
    Date of Patent: April 22, 2003
    Assignee: Eastman Chemical Company
    Inventors: John Clark Hubbs, David Carl Attride, Neil Warren Boaz, James Charles Ciula, John Thorton Maddox, Thomas Nabih, William Dell Nottingham, David Chris Spencer
  • Publication number: 20030050501
    Abstract: A method of synthesizing highly optically enriched &agr;-halo-esters comprises reacting acid halides with a cinchona alkaloid catalyst and a base to form intermediate ketenes. The ketenes are reacted with electrophilic halogenating reagents to produce &agr;-halo-esters with high enantiomeric excess. The base can be an inorganic salt. The thus-formed &agr;-halo-esters have utility in synthesizing other optically-pure materials.
    Type: Application
    Filed: May 18, 2001
    Publication date: March 13, 2003
    Inventor: Harald Wack
  • Publication number: 20030032836
    Abstract: The invention relates to a method for preparing bromodifluoroacetic compounds which comprises converting a 1,1-diflouro-1,2-dibromodihaloethane with oleum having 50-70% SO3 to a bromodifluoroacetyl halide (bromide or chloride) and then in reacting the latter directly with either an alcohol, or with water.
    Type: Application
    Filed: June 18, 2002
    Publication date: February 13, 2003
    Applicant: ATOFINA
    Inventors: Gilles Drivon, Jean-Philippe Gillet, Christophe Ruppin
  • Patent number: 6492550
    Abstract: Inhibitors of the cytosolic phospholypase A2 enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula where X, Z, X1, R1, R2, Ra and Rb are as defined in the specification.
    Type: Grant
    Filed: February 8, 2001
    Date of Patent: December 10, 2002
    Assignee: Bristol-Myers Squibb Company
    Inventors: Jacques Banville, Serge Plamondon, Yonghua Gai, Neelakantan Balasubramanian
  • Patent number: 6452056
    Abstract: A fluorine-containing benzonitrile derivative (formula 1) is subjected to a reduction reaction to obtain a fluorine-containing benzylamine derivative (formula 2), and the amino group in said fluorine-containing benzylamine derivative is replaced with a hydroxyl group to obtain a fluorine-containing benzyl alcohol derivative (formula 3): wherein X is a halogen atom, when m is an integer of 2 or more, each X may be the same or different, and m is an integer of from 0 to 4.
    Type: Grant
    Filed: February 20, 2001
    Date of Patent: September 17, 2002
    Assignee: Asahi Glass Company, Limited
    Inventors: Tsuneo Kawanobe, Osamu Takazawa, Keisuke Yoshikawa, Hiroyuki Watanabe
  • Patent number: 6444842
    Abstract: The present invention provides an improved method for the preparation of carboxylic acid esters of alkylene glycol monoalkyl ethers by the acid catalyzed esterification of the monoalkyl ether with a carboxylic acid. In a preferred embodiment of the invention, the carboxylic acid and alcohol are reacted in a reactor/column and the resulting ester product is distilled into an overhead decanter/extractor as a single phase. A small amount of solvent, preferably a hydrocarbon is added to the mixture causing the resulting distillate to separate into two phases, one phase containing the desired product, the other containing primarily water. The process described is applicable to both batch and continuous operation and is not constrained by the difficulty of separating closely boiling azeotropes and results in substantially higher production rates than achieved by current processes.
    Type: Grant
    Filed: April 19, 2000
    Date of Patent: September 3, 2002
    Assignee: Celanese International Corporation
    Inventors: H. Robert Gerberich, R. Jay Warner
  • Publication number: 20020082444
    Abstract: The invention relates to a process for the synthesis of substituted or unsubstituted aliphatic, cycloaliphatic or araliphatic chloroformates by reaction of the corresponding alcohol with phosgene, diphosgene and/or triphosgene. The reaction is carried out under a pressure of less than or equal to 95×103 Pa, i.e. 950 mbar, and at a temperature of between −30° C. and +50° C.
    Type: Application
    Filed: December 18, 2001
    Publication date: June 27, 2002
    Inventors: Hubert Bonnard, Laurence Ferruccio, Patricia Gauthier, Jean-Pierre Senet
  • Patent number: 6403346
    Abstract: Enzymatic processes can produce intermediates for manufacturing retiferol derivatives that are useful for treating or preventing hyperproliferative skin diseases and for reversing conditions associated with photodamage. These processes can use as a starting material trihydroxycyclohexane, which can be chemically modified by a process that includes an enzymatic step, typically involving lipases of EC-class 3.1.1.3 or 3.1.1.34.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: June 11, 2002
    Assignee: Basilea Pharmaceutica AG
    Inventors: Hans Hilpert, Beat Wirz
  • Patent number: 6383454
    Abstract: A process for fluorinating a hydrocarbon substrate is by mixing it with an inert diluent and mixing the diluted substrate with a gaseous fluorinating reagent to form a foam reaction mixture. The fluorinating reagent reacts with the substrate in the form to foam product. The foam is separated into a liquid component which contains product and a gas component. Product is withdrawn from the liquid component which is then returned to the diluting step. Fluorinating reagent is fed into the gas component which is then recirculated to the mixing step. An installation for fluorinating a hydrocarbon substrate includes, in sequence as a circuit, a dilution stage, a mixing stage, a reaction stage and a separation stage. Liquid returning means feeds liquid from the separation stage to the dilution stage, and gas recirculation means feeds gas from the separation stage to the mixing stage.
    Type: Grant
    Filed: July 13, 2001
    Date of Patent: May 7, 2002
    Assignee: South Africa Nuclear Energy Corporation Ltd.
    Inventors: Driekus Van Der Westhuizen, Petrus Johannes Venter
  • Patent number: 6379552
    Abstract: A method for efficiently resolving optical isomers, in which a discriminating liquid consisting of a discriminating agent capable of discriminating optical isomers and a diluent are brought into contact with a mixture containing said optical isomers in countercurrent flow, to resolve the optical isomers by adsorption separation, distillation separation, absorption separation or membrane separation, and recovered at an optical isomer content of 5 wt % or less for recycled use, under one or more of the following conditions: (a) the dielectric constant of the diluent is 30 or less and the viscosity of the discriminating liquid is 0.
    Type: Grant
    Filed: July 2, 1999
    Date of Patent: April 30, 2002
    Assignee: Toray Industries, Inc.
    Inventors: Tetsuji Kitagawa, Atsushi Okamoto, Takashi Kanai, Katsuhiro Shibayama, Tomoyuki Aoki, Shinobu Yamakawa
  • Patent number: 6369269
    Abstract: A sulfur-containing O-(meth)acrylate compound of the following formula (1) is useful as a starting material for a resin composition used in optical applications such as a lens; wherein R represents hydrogen atom or methyl group; 1 represents an integer from 1 to 3; B is when B is  n is 2; m is 1 or 2; A is selected from the following groups: wherein m represents 1 or 2; each ring may be substituted by one or more alkyl, alkylthio or alkoxy groups having 1 or 2 carbon atoms; p and q are 0 or 1, while m is 1 when p is 1; when B is  n is 1; m is 2 or 3; A is selected from the following groups: —(CH2)r—S—(CH2)r—, —(CH2)r—S—S—(CH2)r—.
    Type: Grant
    Filed: May 23, 2001
    Date of Patent: April 9, 2002
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Seiichi Kobayashi, Nobuya Kawauchi, Toshiyuki Suzuki, Masao Imai, Kenichi Fujii
  • Patent number: 6348622
    Abstract: There is provided a compound of the formula[I]: wherein R represents a hydrogen atom or a protective group for a hydroxyl group; and A represents a hydrogen atom, a halogen atom or a group of the formula A1: Q represents Q3: when A represents a halogen atom or a protective group for a hydroyl group, A represents Q4:  wherein R1 and R2 represent a hydrogen atom or a protective group for a hydroxyl group; and when A represents a hydrogen atom, Q is Q2:
    Type: Grant
    Filed: February 9, 2000
    Date of Patent: February 19, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiya Takahashi, Shinzo Seko, Takashi Miki
  • Patent number: 6310237
    Abstract: A process for the preparation of derivatives of halo-but-2-enoic acids and esters high in 2-ene content, several of which are novel. The esters and their derivatives are useful as promoters for the polymerization of ethylene or the copolymerization of ethylene with &agr;-olefins and, optionally, nonconjugated polyenes. The promoters can also be combined with transition metal compounds, e.g., vanadium, to form combination promoter-catalyst compounds.
    Type: Grant
    Filed: July 18, 2000
    Date of Patent: October 30, 2001
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Xu Wu Feng, Walter Nudenberg
  • Patent number: 6300532
    Abstract: A process for catalytic addition of haloalkanes to alkenes involving the step of reacting the haloalkane with the alkene in the presence of a catalyst. The catalyst is an organophosphite compound represented by the following formula: P(ORa)(ORb)(ORc), where Ra, Rb, and Rc are each an alkyl group or an aralkyl group.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: October 9, 2001
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Timothy Rech Demmin
  • Patent number: 6294680
    Abstract: A process has been provided to produce semi synthetic statins, as for instance simvastatin with a high yield, for another statin, preferably a naturally occurring statin, as for instance lovastatin. Also a number of novel intermediate compounds, prepared during said process, has been provided.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: September 25, 2001
    Assignee: Plus Chemicals, B.V.
    Inventors: Ton Rene Vries, Hans Wijnberg, Wijnand Sjourd Faber, Venetka Ivanova Kalkman-Agayn, Mieke Ivanova Sibeyn