Halogen In Acid Moiety Patents (Class 560/226)
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Patent number: 11905177Abstract: 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: GrantFiled: May 3, 2019Date of Patent: February 20, 2024Assignee: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KGInventors: Maxime Paven, Yuliya Schiesser, Rainer Weber, Gerhard Langstein, Vinh Trieu, Sebastian Hasenstab-Riedel, Nico Schwarze, Simon Steinhauer
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Patent number: 10538474Abstract: 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: GrantFiled: February 4, 2017Date of Patent: January 21, 2020Assignee: PCC MCAA SP. Z O. O.Inventor: Bartosz Bankowski
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Patent number: 10196488Abstract: 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: GrantFiled: November 6, 2015Date of Patent: February 5, 2019Assignees: ELKEM SILICONES FRANCE SAS, UNIVERSITE CLAUDE BERNARD LYON 1, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Vincent Monteil, Jean Raynaud, Delphine Crozet, Magali Bousquié, Sébastien Marrot
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Patent number: 8809451Abstract: 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: GrantFiled: February 18, 2010Date of Patent: August 19, 2014Assignee: Central Glass Company, LimitedInventors: Yoshimi Isono, Satoru Narizuka, Hidehisa Nanai, Kazuhiro Yamanaka
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Publication number: 20140212980Abstract: 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: ApplicationFiled: August 17, 2012Publication date: July 31, 2014Inventors: Takashi Shimada, Taka-Aki Sato, Koichi Tanaka
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Patent number: 8653131Abstract: 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: GrantFiled: August 21, 2009Date of Patent: February 18, 2014Assignees: 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
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Publication number: 20130131375Abstract: 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: ApplicationFiled: July 26, 2011Publication date: May 23, 2013Applicant: RHODIA OPERATIONSInventor: Olivier Buisine
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Patent number: 8318964Abstract: 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: GrantFiled: October 20, 2007Date of Patent: November 27, 2012Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Shigeaki Imazeki, Ryohiko Kinoshita
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Patent number: 8293948Abstract: 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: GrantFiled: January 9, 2012Date of Patent: October 23, 2012Assignee: Jitsubo Co., Ltd.Inventors: Kazuhiro Chiba, Shokaku Kim, Yusuke Kono
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Patent number: 8273914Abstract: 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: GrantFiled: June 27, 2011Date of Patent: September 25, 2012Assignee: Bausch & Lomb IncorporatedInventors: Ivan M. Nunez, David E. Seelye
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Patent number: 8273837Abstract: 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: GrantFiled: December 13, 2006Date of Patent: September 25, 2012Assignee: JSR CorporationInventors: Tomoki Nagai, Takuma Ebata, Nobuji Matsumura
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Publication number: 20100324139Abstract: 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: ApplicationFiled: December 19, 2008Publication date: December 23, 2010Applicants: Generics [UK] Limited, Mylan India Private LimtedInventors: Abhay Gaitonde, Debashish Datta, Bindu Manojkumar, Sunanda Phadtare
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Publication number: 20100324314Abstract: 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: ApplicationFiled: October 20, 2007Publication date: December 23, 2010Applicant: WAKO PURE CHEMICAL INDUSTRIES, LTD.Inventors: Shigeaki Imazeki, Ryohiko Kinoshita
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Publication number: 20100144671Abstract: 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: ApplicationFiled: March 3, 2006Publication date: June 10, 2010Applicant: Women and Infants Hospital of RI, Inc.Inventors: Narasimha Swamy, Hema Malini K. Sundaresha
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Publication number: 20100048483Abstract: 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: ApplicationFiled: August 21, 2009Publication date: February 25, 2010Applicants: 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
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Patent number: 7579498Abstract: 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: GrantFiled: November 29, 2005Date of Patent: August 25, 2009Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Allen Andrews, Alexander Borisovich Shtarov, Joseph Norman Hockman
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Publication number: 20090143604Abstract: 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: ApplicationFiled: November 20, 2008Publication date: June 4, 2009Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
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Publication number: 20090028791Abstract: 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: ApplicationFiled: July 24, 2008Publication date: January 29, 2009Inventors: Julius A. Balatoni, Louis R. DePalatis, William Tong, Juri Gelovani
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Patent number: 7425646Abstract: 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: GrantFiled: December 15, 2006Date of Patent: September 16, 2008Assignee: Asahi Glass Company, LimitedInventors: Kazuya Oharu, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Masahiro Ito
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Patent number: 7423170Abstract: 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: GrantFiled: January 23, 2006Date of Patent: September 9, 2008Assignee: Arizona Biomedical Research CommissionInventors: Seth D. Rose, Scott R. Lefler, Steven R. Ottersberg, Ann Y. Kim, Karl J. Okolotowicz, Rosemarie F. Hartman
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Patent number: 7345192Abstract: Compositions including a conjugate of ?-difluoromethylornithine can be applied topically to reduce hair growth.Type: GrantFiled: November 10, 2005Date of Patent: March 18, 2008Assignee: The Gillette CompanyInventors: Anwar Jardien, Roman Rariy, Gurpreet S. Ahluwalia, Douglas Shander
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Patent number: 7307185Abstract: 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: GrantFiled: March 2, 2005Date of Patent: December 11, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shoji Hara, Tsuyoshi Fukuhara
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Patent number: 7053238Abstract: 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: GrantFiled: July 15, 2004Date of Patent: May 30, 2006Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Daisuke Shirakawa, Masahiro Ito, Shin Tatematsu
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Patent number: 7034179Abstract: 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: GrantFiled: March 27, 2003Date of Patent: April 25, 2006Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Koichi Yanase, Yasuhiro Suzuki, Daisuke Shirakawa
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Patent number: 7019163Abstract: 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: GrantFiled: June 28, 2002Date of Patent: March 28, 2006Assignee: Asahi Kasei Kabushiki KaishaInventors: Nobuyuki Uematsu, Masanori Ikeda
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Patent number: 7015349Abstract: Compositions including a conjugate of ?-difluoromethylornithine can be applied topically to reduce hair growth.Type: GrantFiled: March 26, 2003Date of Patent: March 21, 2006Assignee: The Gillette CompanyInventors: Anwar Jardien, Roman Rariy, Gurpreet S. Ahluwalia, Douglas Shander
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Patent number: 6903233Abstract: 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: GrantFiled: March 10, 2003Date of Patent: June 7, 2005Assignee: Takasago International CorporationInventors: Akira Amano, Daisuke Igarashi, Takashi Miura
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Patent number: 6858752Abstract: 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: GrantFiled: March 27, 2003Date of Patent: February 22, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Daisuke Shirakawa, Masahiro Ito, Shin Tatematsu
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Patent number: 6858748Abstract: 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: GrantFiled: January 13, 2004Date of Patent: February 22, 2005Assignee: Research Foundation of the University of Central FloridaInventors: D. Howard Miles, Solodnikov Sergey Yurjevich, Krasnykh Olga Petrovna, Lisovskaja Natalja Anatoljevna, Elena A. Goun
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Patent number: 6833468Abstract: 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: GrantFiled: July 26, 2002Date of Patent: December 21, 2004Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
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Patent number: 6720447Abstract: 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&equType: GrantFiled: July 17, 2001Date of Patent: April 13, 2004Assignee: BASF AktiengesellschaftInventors: Klaus Ditrich, Ulrich Block
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Patent number: 6703520Abstract: 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: GrantFiled: April 5, 2002Date of Patent: March 9, 2004Assignee: 3M Innovative Properties CompanyInventors: Klaus Hintzer, Egon Obermaier, Werner Schwertfeger
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Patent number: 6642409Abstract: 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: GrantFiled: January 29, 2001Date of Patent: November 4, 2003Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
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Patent number: 6639100Abstract: 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: GrantFiled: August 7, 2002Date of Patent: October 28, 2003Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
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Patent number: 6583313Abstract: 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: GrantFiled: July 10, 1998Date of Patent: June 24, 2003Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Kerstin Eichholz, Werner Rudolph
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Patent number: 6552217Abstract: 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: GrantFiled: July 2, 2001Date of Patent: April 22, 2003Assignee: Eastman Chemical CompanyInventors: John Clark Hubbs, David Carl Attride, Neil Warren Boaz, James Charles Ciula, John Thorton Maddox, Thomas Nabih, William Dell Nottingham, David Chris Spencer
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Publication number: 20030050501Abstract: 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: ApplicationFiled: May 18, 2001Publication date: March 13, 2003Inventor: Harald Wack
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Publication number: 20030032836Abstract: 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: ApplicationFiled: June 18, 2002Publication date: February 13, 2003Applicant: ATOFINAInventors: Gilles Drivon, Jean-Philippe Gillet, Christophe Ruppin
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Patent number: 6492550Abstract: 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: GrantFiled: February 8, 2001Date of Patent: December 10, 2002Assignee: Bristol-Myers Squibb CompanyInventors: Jacques Banville, Serge Plamondon, Yonghua Gai, Neelakantan Balasubramanian
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Patent number: 6452056Abstract: 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: GrantFiled: February 20, 2001Date of Patent: September 17, 2002Assignee: Asahi Glass Company, LimitedInventors: Tsuneo Kawanobe, Osamu Takazawa, Keisuke Yoshikawa, Hiroyuki Watanabe
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Patent number: 6444842Abstract: 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: GrantFiled: April 19, 2000Date of Patent: September 3, 2002Assignee: Celanese International CorporationInventors: H. Robert Gerberich, R. Jay Warner
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Publication number: 20020082444Abstract: 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: ApplicationFiled: December 18, 2001Publication date: June 27, 2002Inventors: Hubert Bonnard, Laurence Ferruccio, Patricia Gauthier, Jean-Pierre Senet
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Patent number: 6403346Abstract: 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: GrantFiled: September 6, 2001Date of Patent: June 11, 2002Assignee: Basilea Pharmaceutica AGInventors: Hans Hilpert, Beat Wirz
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Patent number: 6383454Abstract: 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: GrantFiled: July 13, 2001Date of Patent: May 7, 2002Assignee: South Africa Nuclear Energy Corporation Ltd.Inventors: Driekus Van Der Westhuizen, Petrus Johannes Venter
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Patent number: 6379552Abstract: 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: GrantFiled: July 2, 1999Date of Patent: April 30, 2002Assignee: Toray Industries, Inc.Inventors: Tetsuji Kitagawa, Atsushi Okamoto, Takashi Kanai, Katsuhiro Shibayama, Tomoyuki Aoki, Shinobu Yamakawa
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Patent number: 6369269Abstract: 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: GrantFiled: May 23, 2001Date of Patent: April 9, 2002Assignee: Mitsui Chemicals, Inc.Inventors: Seiichi Kobayashi, Nobuya Kawauchi, Toshiyuki Suzuki, Masao Imai, Kenichi Fujii
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Patent number: 6348622Abstract: 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: GrantFiled: February 9, 2000Date of Patent: February 19, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiya Takahashi, Shinzo Seko, Takashi Miki
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Process for the preparation and uses of derivatives of esters of &agr;-methylene-&bgr;-hydroxy acids
Patent number: 6310237Abstract: 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: GrantFiled: July 18, 2000Date of Patent: October 30, 2001Assignee: Uniroyal Chemical Company, Inc.Inventors: Xu Wu Feng, Walter Nudenberg -
Patent number: 6300532Abstract: 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: GrantFiled: December 15, 1998Date of Patent: October 9, 2001Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, Timothy Rech Demmin
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Patent number: 6294680Abstract: 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: GrantFiled: January 5, 2000Date of Patent: September 25, 2001Assignee: Plus Chemicals, B.V.Inventors: Ton Rene Vries, Hans Wijnberg, Wijnand Sjourd Faber, Venetka Ivanova Kalkman-Agayn, Mieke Ivanova Sibeyn