Haloalkyl Containing Compound Patents (Class 570/144)
  • Patent number: 9056809
    Abstract: The present invention disclosed a preparation method of parylene AF4, which provides a reactant and a reducing agent with the use of catalyst or exposure to UV light with photo-initiator, to shorten the reaction time as a result of minimized the byproduct(s) formation, and obtain high purity (>99.0%) of parylene AF4 product under high concentrated reaction mixture.
    Type: Grant
    Filed: September 21, 2012
    Date of Patent: June 16, 2015
    Assignee: YUAN-SHIN MATERIALS TECHNOLOGY CORP.
    Inventors: Chun-Hsu Lin, Chien-Yi Sun, Yung-Yu Yin, Chun-Shih Li, Yo-Chun Chou
  • Patent number: 8987520
    Abstract: This invention relates to fluoroalkyl and chlorofluoroalkyl benzenes with relatively high boiling points, having zero ozone depletion potential and low global warming potential. This invention also relates to the preparation of such fluoroalkyl and chlorofluoroalkyl benzenes. These materials can be used as reaction and heat transfer media, cleaning agents and as intermediates for biologically active materials.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: March 24, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventor: Viacheslav A Petrov
  • Publication number: 20150045580
    Abstract: Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of a difluoromethyl group with readily available reagents to form difluoromethylarenes. The reaction of electron-neutral, electronrich, and sterically hindered aryl and vinyl iodides with the combination of Cul, CsF and TMSCF2H leads to the formation of difluoromethylarenes in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF2H.
    Type: Application
    Filed: March 5, 2013
    Publication date: February 12, 2015
    Inventors: John Hartwig, Patrick Fier
  • Publication number: 20140357906
    Abstract: A method of manufacturing a fluorine-containing aromatic compound represented by the following formula (2-1) or formula (2-2): [R is a hydrogen atom, an alkyl group having a carbon number of 1 to 12 which may have a substituent other than a fluorine atom, or a monovalent aromatic group which may have a substituent; Rf1 and Rf2 are a fluorine-containing alkyl group having a carbon number of 1 to 12 and Rf1 and Rf2 may be the same or different; and m is an integer of 1 or more, n is an integer of 0 or more and m+n is an integer of 1 or more and 5 or less].
    Type: Application
    Filed: August 13, 2014
    Publication date: December 4, 2014
    Inventors: Tomoko YAJIMA, Kyoko YAMAMOTO
  • Publication number: 20140249329
    Abstract: Methods of halogenating a carbon containing compound having an sp3 C—H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond are provided. The halogenated products of the methods are provided.
    Type: Application
    Filed: August 20, 2012
    Publication date: September 4, 2014
    Applicant: The Trustees of Princeton University
    Inventors: John T. Groves, Wei Liu
  • Patent number: 8816139
    Abstract: The present invention relates to a facile method of preparing 1,4-bis(chlorodifluoromethyl)benzene, comprising the steps of: (A) providing a reactant liquid of 1,4-bis(difluoromethyl)benzene; optionally (B) providing a light source for UV radiation; and (C) introducing chlorine gas into the reactant liquid at a temperature of 50-90° C. under a pressure above 1 atm to obtain 1,4-Bis(chlorodifluoromethyl)benzene. The invented facile method can be utilized in a batch process or a continuous process for effective production of 1,4-bis(chlorodifluoromethyl)benzene.
    Type: Grant
    Filed: May 22, 2012
    Date of Patent: August 26, 2014
    Assignees: Yuan-Shin Materials Technology Corp., Chung-Shan Institute of Science and Technology, Armaments Bureau, M.N.D.
    Inventors: Chun Hsu Lin, Hung Cheng Yin, Chien Yi Sun, Yung Yu Yin, Chuan Yu Chou
  • Publication number: 20140221632
    Abstract: The present invention disclosed a preparation method of parylene AF4, which provides a reactant and a reducing agent with the use of catalyst or exposure to UV light with photo-initiator, to shorten the reaction time as a result of minimized the byproduct(s) formation, and obtain high purity (>99.0%) of parylene AF4 product under high concentrated reaction mixture.
    Type: Application
    Filed: April 7, 2014
    Publication date: August 7, 2014
    Inventors: Chun-Hsu LIN, Chian-Yi SUN, Yung-Yu YIN, Chun-Shih LI, Yo-Chun CHOU
  • Publication number: 20140221655
    Abstract: The invention provides methods for substituting polyaromatic hydrocarbons or polyheterocyclic compounds with perfluoroalkyl groups. The methods can include heating a polyaromatic hydrocarbon substrate or a polyheterocyclic compound substrate in the presence of a perfluoroalkyl iodide, typically in a closed system, wherein the heating is sufficient to bring both the polyaromatic hydrocarbons or polyheterocyclic compound, and the perfluoroalkyl iodide, into the gas phase, thereby allowing the substrate to react with the perfluoroalkyl iodide in the gas phase to form polyaromatic hydrocarbons or polyheterocyclic compounds having one or more perfluoroalkyl substituents. The methods allow for the creation of versatile libraries of novel perfluoroalkyl-containing derivatives that can serve as important building blocks and active components in biomedical, electronic, and materials applications.
    Type: Application
    Filed: February 6, 2014
    Publication date: August 7, 2014
    Applicant: Colorado State University Research Foundation
    Inventors: Steven S. Strauss, Olga V. Boltalina, Igor V. Kuvychko
  • Publication number: 20140200372
    Abstract: This invention relates to fluoroalkyl and chlorofluoroalkyl benzenes with relatively high boiling points, having zero ozone depletion potential and low global warming potential. This invention also relates to the preparation of such fluoroalkyl and chlorofluoroalkyl benzenes. These materials can be used as reaction and heat transfer media, cleaning agents and as intermediates for biologically active materials.
    Type: Application
    Filed: December 18, 2013
    Publication date: July 17, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: Viacheslav A. Petrov
  • Publication number: 20140058101
    Abstract: The invention is directed to a phosphine compound represented by general formula (1) wherein R? and R? independently are selected from alkyl, cycloalkyl and 2-furyl radicals, or R? and R? are joined together to form with the phosphorous atom a carbon-phosphorous monocycle comprising at least 3 carbon atoms or a carbon-phosphorous bicycle; the alkyl radicals, cycloalkyl radicals, and carbon-phosphorous monocycle being unsubstituted or substituted by at least one radical selected from the group of alkyl, cycloalkyl, aryl, alkoxy, and aryloxy radicals; Cps is a partially substituted or completely substituted cyclopentadien-1-yl group, including substitutions resulting in a fused ring system, and wherein a substitution at the 1-position of the cyclopentadien-1-yl group is mandatory when the cyclopentadien-1-yl group is not part of a fused ring system or is part of an indenyl group. Also claimed is the use of these phosphines as ligands in catalytic reactions and the preparation of these phosphines.
    Type: Application
    Filed: October 29, 2013
    Publication date: February 27, 2014
    Applicant: Evonik Degussa GmbH
    Inventors: Herbert Plenio, Christoph Fleckenstein, Renat Kadyrov, Juan Almena, Axel Monsees, Thomas Riermeier
  • Publication number: 20140011986
    Abstract: The present invention disclosed a preparation method of parylene AF4, which provides a reactant and a reducing agent with the use of catalyst or exposure to UV light with photo-initiator, to shorten the reaction time as a result of minimized the byproduct(s) formation, and obtain high purity (>99.0%) of parylene AF4 product under high concentrated reaction mixture.
    Type: Application
    Filed: September 21, 2012
    Publication date: January 9, 2014
    Inventors: Chun-Hsu LIN, Chien-Yi SUN, Yung-Yu YIN, Chun-Shih LI, Yo-Chun CHOU
  • Patent number: 8530666
    Abstract: The present invention relates to a process for the production of trifluoromethylated unsubstituted or substituted aryl or heteroaryl compounds which comprises reacting an unsubstituted or substituted aryl or heteroaryl halide with a trifluoroacetate of formula (I) or (II), wherein R1 is hydrogen or a C1-C5 alkyl group and M an alkali metal or an ammonium ion, in the presence of and an anorganic halogenide salt or a trifluoroacetacid salt as activator compound and a catalytic combination of a copper salt with a monodentate, bidentate or tridentate aromatic or aliphatic amine or pyridine ligand.
    Type: Grant
    Filed: October 26, 2011
    Date of Patent: September 10, 2013
    Assignee: SALTIGO GmbH
    Inventors: Alain Cotté, Matthias Gotta, Matthias Beller, Thomas Schareina, Alexander Zapf, Xiao-Feng Wu
  • Publication number: 20130190540
    Abstract: A method for preparing optically active 1-bromo-1-[3,5-bis(trifluoromethyl)-phenyl]ethane having a high optical purity, which comprises the step of brominating optically active 1-[3,5-bis(trifluoromethyl)phenyl]ethanol by using, as a brominating agent, (a) a combination of a phosphorus halide and hydrogen bromide, (b) a combination of 1,2-dibromo-1,1,2,2-tetrachloroethane and an organic phosphorous compound represented by the general formula (I): P(R1)(R2)(R3) (in the formula, R1, R2, and R3 independently represent a C6-10 aryl group, a C6-10 aryloxy group, a C1-10 alkyl group, a C1-10 alkoxyl group, a C3-6 cycloalkyl group, or a C3-6 cycloalkoxy group), or (c) a combination of N-bromosuccinimide and a dialkyl sulfide.
    Type: Application
    Filed: July 21, 2011
    Publication date: July 25, 2013
    Applicant: Kowa Company, Ltd.
    Inventors: Taichi Kusakabe, Kennosuke Matsuda, Koichi Yamazaki, Tadaaki Ohgiya, Kimiyuki Shibuya
  • Patent number: 8455592
    Abstract: Disclosed is a polycondensation process for preparing block copolyesters comprising blocks of fluoroether functionalized aromatic polyester and blocks of unmodified polyester. According to the process, a non-fluorinated poly(alkylene arylate) first homopolymer and a fluoroether functionalized poly(alkylene arylate) second homopolymer are combined to form a reaction mixture; the reaction mixture is heated to a temperature above the melting temperatures of each said homopolymer to prepare a molten reaction mixture; and the reaction is continued until the desired molecular weight is achieved. The block copolymers incorporated into blends with unmodified aromatic polyester impart oil and soil resistance to shaped articles prepared from the blends.
    Type: Grant
    Filed: November 8, 2011
    Date of Patent: June 4, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Elizabeth Forrester Mccord, Fredrik Nederberg
  • Publication number: 20130131401
    Abstract: The present invention is a process for the preparation of chymase modulators, useful in the treatment of inflammatory and serine protease mediated disorders.
    Type: Application
    Filed: January 15, 2013
    Publication date: May 23, 2013
    Applicant: Janssen Pharmaceutica, NV
    Inventor: Janssen Pharmaceutica, NV
  • Publication number: 20130116482
    Abstract: The present invention relates to a facile method of preparing 1,4-bis(chlorodifluoromethyl)benzene, comprising the steps of: (A) providing a reactant liquid of 1,4-bis(difluoromethyl)benzene; optionally (B) providing a light source for UV radiation; and (C) introducing chlorine gas into the reactant liquid at a temperature of 50-90° C. under a pressure above 1 atm to obtain 1,4-Bis(chlorodifluoromethyl)benzene. The invented facile method can be utilized in a batch process or a continuous process for effective production of 1,4-bis(chlorodifluoromethyl)benzene.
    Type: Application
    Filed: May 22, 2012
    Publication date: May 9, 2013
    Applicants: Chung-shan Institute of Science and Technology. Armaments Bureau. M.N.D., Yuan-Shin Materials Technology Corp.
    Inventors: Chun-Hsu LIN, Hung-Cheng Yin, Chien-Yi Sun, Yung-Yu Yin, Chuan-Yu Chou
  • Patent number: 8383867
    Abstract: Disclosed is a method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CFnCHmXa-m??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where each X is independently Cl, F, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a-m?0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a Cl addition agent under conditions effective to produce a compound of formula (I).
    Type: Grant
    Filed: November 3, 2006
    Date of Patent: February 26, 2013
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Rajesh K. Dubey, Rajiv R. Singh, George A. Shia
  • Publication number: 20120330072
    Abstract: This invention relates to a method of reacting fluoroolefin with an organic magnesium compound in the presence of a catalyst comprising nickel or palladium so as to efficiently produce fluoroolefin, such as TFE, in which a fluorine (F) atom or atoms bonded to the sp2 hybridized carbon atom are substituted with an organic group.
    Type: Application
    Filed: March 3, 2011
    Publication date: December 27, 2012
    Inventors: Takabumi Nagai, Takashi Shibanuma, Sensuke Ogoshi, Masato Ohashi
  • Publication number: 20120245360
    Abstract: The present invention relates to a process for the production of trifluoromethylated unsubstituted or substituted aryl or heteroaryl compounds which comprises reacting an unsubstituted or substituted aryl or heteroaryl halide with a trifluoroacetate of formula (I) or (II), wherein R1 is hydrogen or a C1-C5 alkyl group and M an alkali metal or an ammonium ion, in the presence of and an anorganic halogenide salt or a trifluoroacetacid salt as activator compound and a catalytic combination of a copper salt with a monodentate, bidentate or tridentate aromatic or aliphatic amine or pyridine ligand.
    Type: Application
    Filed: October 26, 2011
    Publication date: September 27, 2012
    Applicant: SALTIGO GMBH
    Inventors: Alain Cotté, Matthias Gotta, Matthias Beller, Thomas Schareina, Alexander Zapf, Xiao-feng Wu
  • Publication number: 20120208989
    Abstract: Fluorinated aromatic materials, their synthesis and their use in optoelectronics. In some cases, the fluorinated aromatic materials are perfluoroalkylated aromatic materials that may include perfluoropolyether substituents.
    Type: Application
    Filed: August 20, 2010
    Publication date: August 16, 2012
    Applicant: THE UNIVERSITY OF SOUTH DAKOTA
    Inventor: Haoran Sun
  • Publication number: 20120142915
    Abstract: This disclosure concerns a protected cyclopropylboronic acid comprising a substituted cyclopropyl group and a boronic ester group having a protecting group. The protecting group is an N-methyliminodiacetic acid (MIDA) group or MIDA-based group.
    Type: Application
    Filed: December 1, 2011
    Publication date: June 7, 2012
    Inventors: Matthew Duncton, Rajinder Singh
  • Publication number: 20120029211
    Abstract: A catalytic Wittig method utilizing a phosphine including the steps of providing a phosphine oxide precatalyst and reducing the phosphine oxide precatalyst to produce the phosphine; forming a phosphonium ylide precursor from the phosphine and a reactant; generating a phosphonium ylide from the phosphonium ylide precursor; reacting the phosphonium ylide precursor with the aldehyde, ketone, or ester to form the olefin and the phosphine oxide which then reenters the cycle. The invention is also directed to a Mitsunobu reaction catalytic in phosphine.
    Type: Application
    Filed: April 6, 2010
    Publication date: February 2, 2012
    Inventor: Christopher J. O'Brien
  • Patent number: 7994372
    Abstract: Fluorinated paracyclophane compounds represented by the formula: where least one of R1 and R2 comprises a fluorinated moiety is disclosed. These compounds can be utilized as precursor dimer compounds to produce polymeric coatings comprising copolymers of trifluorinated paraxylylene, including flexible fluorinated paraxylylene coatings.
    Type: Grant
    Filed: December 9, 2008
    Date of Patent: August 9, 2011
    Assignee: Specialty Coating Systems, Inc.
    Inventors: Rakesh Kumar, Phillip Hanefeld, Sven Horst, Markus Meise, Andreas Greiner, Michael Bognitzki
  • Publication number: 20110112293
    Abstract: The present invention provides novel and advantageous processes for preparing and purifying chemical compounds such as pharmaceuticals. The processes comprise a nucleophilic substitution reaction with a moiety X wherein the leaving group L of a substrate S in the reaction is covalently attached to a purification moiety M. This concept offers a convenient and lime-saving way to purity the desired product S-X from non-reacted precursors S-L-M and by-products L-M.
    Type: Application
    Filed: April 9, 2009
    Publication date: May 12, 2011
    Applicant: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
    Inventors: John Cyr, Ananth Srinivasan, Mathias Berndt, Keith Graham, Dae Yoon Chi, Byoung Se Lee, So Young Chu, Song-Yi Lim, Sang Ju Lee, Jin-Sook Ryu, Seung Jun Oh
  • Publication number: 20110068290
    Abstract: Compounds, compositions, systems and methods for the chemical and electrochemical modification of the electronic structure of graphene and especially epitaxial graphene (EG) are presented. Beneficially, such systems and methods allow the large-scale fabrication of electronic EG devices. Vigorous oxidative conditions may allow substantially complete removal of the EG carbon atoms and the generation of insulating regions; such processing is equivalent to that which is currently used in the semiconductor industry to lithographically etch or oxidize silicon and thereby define the physical features and electronic structure of the devices. However graphene offers an excellent opportunity for controlled modification of the hybridization of the carbon atoms from sp2 to sp3 states by chemical addition of organic functional groups.
    Type: Application
    Filed: May 29, 2009
    Publication date: March 24, 2011
    Applicant: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
    Inventors: Robert C. Haddon, Mikhail E. Itkis, Palanisamy Ramesh, Elena Bekyarova, Sakhrat Khizroev, Jeongmin Hong
  • Patent number: 7807236
    Abstract: The invention relates to a liquid-crystalline medium, characterised in that it comprises one or more compounds of the formula I in which R0, L1, n, A and B have the meanings indicated in Claim 1, furthermore to novel compounds of the formula I, to processes for the preparation thereof, to the use thereof in electronic and electro-optical devices, in particular in LC displays, and to LC displays containing same.
    Type: Grant
    Filed: February 1, 2008
    Date of Patent: October 5, 2010
    Assignee: Merck Patent Gesellschaft
    Inventors: Harald Hirschmann, Michael Wittek, Markus Czanta, Volker Reiffenrath
  • Publication number: 20100145075
    Abstract: The present invention is a process for the preparation of chymase modulators, useful in the treatment of inflammatory and serine protease mediated disorders.
    Type: Application
    Filed: October 29, 2009
    Publication date: June 10, 2010
    Inventors: Luigi Anzalone, Penina Feibush, Ilias Konstantinos Dorziotis, Xun Li, Frank J. Villani
  • Patent number: 7732022
    Abstract: Disclosed are fluorostilbene compounds of formula I, liquid-crystal media which comprise these compounds, the use of the media in electro-optical displays, in particular in VAN LCDs, and a process for the preparation of these compounds.
    Type: Grant
    Filed: December 10, 2007
    Date of Patent: June 8, 2010
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Melanie Klasen-Memmer, Matthias Bremer, Atsutaka Manabe
  • Patent number: 7652178
    Abstract: A composition comprising perfluoro-[2,2]-paracyclophane dimer compound is disclosed. The synthesis reaction of the paracyclophane dimer from 1,4-bis(chlorodifluoromethane)-2,3,5,6-tetrafluorobenzene involves heating in the presence of a metal catalyst and a solvent. A perfluorinated paraxylylene coating formed from the perfluorinated paracyclophane dimer is also disclosed.
    Type: Grant
    Filed: February 26, 2007
    Date of Patent: January 26, 2010
    Assignee: Specialty Coating Systems, Inc.
    Inventors: William R. Dolbier, Jr., Puhui Xie, Rakesh Kumar
  • Patent number: 7648743
    Abstract: The disclosed is a liquid crystal compound and method for manufacturing the same. The liquid crystal compound can be used alone or mixed with commercially available liquid crystal compounds. Because low rotational viscosity of the liquid crystal compound of the invention, it can be used as positive or negative dielectric anisotropic liquid crystal composition.
    Type: Grant
    Filed: April 3, 2008
    Date of Patent: January 19, 2010
    Assignee: Industrial Technology Research Institute
    Inventors: An-Cheng Chen, Pei-Chen Huang, Kung-Lung Cheng, Shih-Hsien Liu
  • Patent number: 7524992
    Abstract: The invention relates to a carbon-carbon bond creation method comprising the coupling of a transferable group and an acceptor group. The inventive method comprises the following steps: a) activation of a siliceous compound bearing a transferable group by an activation agent; b) addition of an acceptor group-bearing derivative; and, simultaneously or in any consecutive order, c) addition of a palladacycle-type compound acting as a catalyst of the coupling reaction between the transferable group and the acceptor group with the creation of the carbon-carbon bond.
    Type: Grant
    Filed: August 24, 2004
    Date of Patent: April 28, 2009
    Assignee: Rhodia Chimie
    Inventor: Johann Vastra
  • Patent number: 7462750
    Abstract: Fluorinated paracyclophane compounds represented by the formula where least one of R1 and R2 comprises a fluorinated moiety is disclosed. These compounds can be utilized as precursor dimer compounds to produce polymeric coatings comprising copolymers of trifluorinated paraxylylene.
    Type: Grant
    Filed: October 31, 2005
    Date of Patent: December 9, 2008
    Assignee: Specialty Coating Systems, Inc.
    Inventors: Phillip Hanefeld, Sven Horst, Markus Meise, Michael Bognitzki, Andreas Greiner, Rakesh Kumar
  • Publication number: 20080149891
    Abstract: Disclosed are fluorostilbene compounds of formula I, liquid-crystal media which comprise these compounds, the use of the media in electro-optical displays, in particular in VAN LCDs, and a process for the preparation of these compounds.
    Type: Application
    Filed: December 10, 2007
    Publication date: June 26, 2008
    Inventors: MELANIE KLASEN-MEMMER, MATTHIAS BREMER, ATSUTAKA MANABE
  • Patent number: 7238832
    Abstract: There is provided a method for producing a coupling compound of formula (1): (Y—)(n?1)R1—R2—(R1)(n??1)??(1) wherein R1, R2 n and n? are as defined below, Y is R2 or X as defined below, which method comprises reacting an organic halogen compound of formula (2): n?(R1X1n)??(2) wherein X1 represents a bromine or iodine, R1 represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which ? and ? carbon atoms in relation to X1 are sp3 carbon atoms, n and n? each independently represent an integer of 1 or 2, and provided that n and n? do not simultaneously represent 2, with an organic boron compound of formula (3): m{R2(BX22)n?}??(3) wherein R2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkenyl group and the boron atom is bonded with a sp2 carbon atom thereof, X2 represents a hydroxyl or alkoxy group, n? is as defined above, m represents an integer of 1 or 2, and m is not more than n, in the presence of a catalyst comprising a) a nick
    Type: Grant
    Filed: February 18, 2004
    Date of Patent: July 3, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamon Itahashi, Takashi Kamikawa
  • Patent number: 7214838
    Abstract: A method for transferring TCPX (?, ?, ??, ??-tetrachloro-p-xylene) into TFPX (?, ?, ??, ??-tetrafluoro-p-xylene) is disclosed, which comprises the following steps: (a) providing a first reactant comprising TFPX; (b) mixing the first reactant with alkali metal fluorides, TCPX and phase transfer catalyst(s) to form a mixture, wherein the alkali metal fluorides is KF, CsF, NaF, LiF or the combination thereof, the phase transfer catalyst(s) is quaternary ammonium salt, quaternary phosphonium salt or the combination thereof; and (c) heating the mixture.
    Type: Grant
    Filed: July 27, 2005
    Date of Patent: May 8, 2007
    Assignee: Yuan-Shin Materials Technology Corp.
    Inventors: Chun-Hsu Lin, Jao-Jou Tu, Te-Po Liou, Shieh-Jun Wang
  • Patent number: 7173159
    Abstract: A method for the synthesis of TFPX (?, ?, ??, ??-tetrafluoro-p-xylene) is disclosed, which comprises the following steps: (a) providing a sulpholane solution comprising TCPX (?, ?, ??, ??-tetrachloro-p-xylene); (b) mixing the sulpholane solution with alkali metal fluoride, and phase transfer catalyst to form a mixture, wherein the phase transfer catalyst is quaternary phosphonium salt; and (c) heating the mixture.
    Type: Grant
    Filed: July 27, 2005
    Date of Patent: February 6, 2007
    Assignee: Yuan-Shin Materials Technology Corp.
    Inventors: Chan-Yuan Ho, Tsair-Feng Lin, Chun-Hsu Lin, Shieh-Jun Wang
  • Patent number: 7145046
    Abstract: Inorganic and organic compounds containing fluorine can be produced, for example, from corresponding chlorine-containing compounds by chlorine/fluorine exchange using fluorinating agents. Monocyclic or bicyclic compounds containing at least two nitrogen atoms, at least one of which is incorporated into the ring system, can be used as catalysts or fluorinating agents for chlorine/fluorine exchange reactions to produce sulfurylchlorofluoride, sulfurylfluoride or a carboxylic acid fluoride. It is likewise possible to carry out HF addition to unsaturated carbon-carbon bonds or chlorine/fluorine exchange at carbon atoms. For example, monochloro or dichloro malonic acid esters can be converted to difluoro malonic acid esters. Work-up of the reaction mixture can be simplified by using suitable solvents which force the reaction mixture to exist in two phases.
    Type: Grant
    Filed: August 1, 2003
    Date of Patent: December 5, 2006
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Carsten Brosch
  • Patent number: 7041859
    Abstract: A method for obtaining a halogenated organic compound, whereby an organotrifluoroborate compound is reacted with a halide ion in the presence of an oxidizing agent to produce the corresponding halogenated organic compound. The method may be used for producing radiohalogenated organic compounds.
    Type: Grant
    Filed: July 5, 2005
    Date of Patent: May 9, 2006
    Assignee: University of Tennessee Research Foundation
    Inventor: George W. Kabalka
  • Patent number: 7022865
    Abstract: A tetrahydropyran derivative comprising at least three cyclic rings and one aromatic endgroup of the formula A a process for preparing said tetrahydropyran derivatives, and the use of said tetrahydropyran derivatives as a component in a liquid crystal composition.
    Type: Grant
    Filed: May 27, 2004
    Date of Patent: April 4, 2006
    Assignee: Merck Patent GmbH
    Inventors: Mark John Goulding, Warren Duffy, Kevin Adlem, Peer Kirsch, Alexander Hahn, Eike Poetsch, Werner Binder, Volker Meyer, Melanie Klasen-Memmer, Michael Heckmeier, Georg Lüssem
  • Patent number: 6955837
    Abstract: Novel phenylcyclohexanes of the formula I in which n is 0 to 7, Q1 and Q2 are H, or one of these radicals is alternatively CH3, r is 0, 1, 2, 3, 4 or 5, A is trans-1,4-cyclohexylene, 1,4-phenylene, 3-fluoro-1,4-phenylene or a single bond, X is F, Cl, —CF3, —CN, —OCF3 or —OCHF2, and Y and Z are each, independently of one another, H or F, with the proviso that, in the case where A is a single bond, Q1=Q2=H and simultaneously X=CN, Y and/or Z are F.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: October 18, 2005
    Assignee: Merck Patent GmbH
    Inventors: Andreas Wachtler, Reinhard Hittich, Eike Poetsch, Herbert Plach, David Coates, Bernhard Rieger, Joachim Krause
  • Patent number: 6908645
    Abstract: The invention relates to liquid-crystalline compounds of the formula I and to a liquid-crystalline medium based on a mixture of polar compounds, characterized in that it comprises one or more compounds of the general formula I in which R1, L1, L2, L3, L4, L5, L6, Z1, Z2, X, v and u are as defined in claim 1.
    Type: Grant
    Filed: September 30, 2003
    Date of Patent: June 21, 2005
    Assignee: Merck Patent GmbH
    Inventors: Peer Kirsch, Marc Lenges, Michael Heckmeier
  • Patent number: 6875894
    Abstract: The invention relates to bis(alkylthio)carbenium salts of the formula I with the stated definitions for R1, R2, R3 and Y?, and to a process for the preparation thereof. The compounds according to the invention are advantageously suitable as electrophilic reagents for the transfer of fluorinated alkyl and acyl radicals onto nucleophilic compounds.
    Type: Grant
    Filed: February 11, 2002
    Date of Patent: April 5, 2005
    Assignee: Merck Patent GmbH
    Inventors: Peer Kirsch, Andreas Ruhl, Gerd-Volker Röschenthaler, Dmitrii Sevenard
  • Patent number: 6872861
    Abstract: The invention relates to a process for preparing polyfluoroalkyl-lithium compounds by deprotonation of polyfluoroalkyl compounds by means of lithium bases.
    Type: Grant
    Filed: June 7, 2002
    Date of Patent: March 29, 2005
    Assignee: Bayer Aktiengesellschaft
    Inventors: Marielouise Schneider, Albrecht Marhold, Alexander Kolomeitsev, Alexander Kadyrov, Gerd-Volker Röschenthaler, Jan Barten
  • Publication number: 20040169159
    Abstract: Novel phenylcyclohexanes of the formula I 1
    Type: Application
    Filed: September 28, 2001
    Publication date: September 2, 2004
    Applicant: MERCK KGAA
    Inventors: Andreas Wachtler, Reinhard Hittich, Eike Poetsch, Herbert Plach, David Coates, Bernhard Rieger, Joachim Krause
  • Patent number: 6784327
    Abstract: A process for the production of a fluorinated organic compound, characterized by fluorinating an organic compound having a hydrogen atoms using IF5; and a novel fluorination process for fluorinating an organic compound having a hydrogen atoms by using a fluorinating agent containing IF5 and at least one member selected from the group consisting of acids, bases, salts and additives.
    Type: Grant
    Filed: December 10, 2002
    Date of Patent: August 31, 2004
    Assignee: Daikin Industries, Ltd.
    Inventors: Norihiko Yoneda, Tsuyoshi Fukuhara, Kazuhiro Shimokawa, Kenji Adachi, Satoshi Oishi
  • Patent number: 6781021
    Abstract: A catalyst composition with a high halogenated aromatics isomerization activity, a halogenated aromatic isomerization method using said catalyst composition, and a halogenated aromatics isomerization method capable of prolonging the life or regeneration period of the catalyst. The invention also includes a catalyst composition characterized in that the maximum diameter of secondary particles of the zeolite in the formed catalyst is 5 microns or less is used to improve the halogenated aromatics isomerization activity. Furthermore, if dissolved oxygen is decreased, the life or regeneration period of the catalyst can be prolonged.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: August 24, 2004
    Assignee: Toray Industries, Inc.
    Inventors: Hajime Kato, Kazuyoshi Iwayama, Masashi Kato, Shinobu Yamakawa, Hirohito Okino
  • Patent number: 6753444
    Abstract: The invention relates to a process for preparing 2,3,5,6-tetrahaloxylylidene compounds of formula (I) where each Hal is independently fluorine or chlorine, and X is fluorine, chlorine, bromine, —O—R, or —O—C(═O)R, where R is hydrogen, a straight-chain or branched C1-C12-alkyl- or a C6-C14-aryl radical, by reacting 2,3,5,6-tetrahaloxylylidenediamines of formula (II) with an alkyl nitrite and/or nitrous acid in HX as a solvent.
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: June 22, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Langer, Lars Rodefeld
  • Patent number: 6706934
    Abstract: Disclosed herein is a method for producing 2,3,4,5-tetrachlorobenzotrifluoride comprising chlorinating 4-chlorobenzotrifluoride with elemental chlorine, in the presence of from 0.1 to 2% by weight of iron(III) chloride and 0.05 to 0.75% by weight of aluminum(III) chloride, in each case based on 4-chlorobenzotrifluoride, where the weight ratio of iron(III) chloride to aluminum(III) chloride is 10:1 to 1:1.
    Type: Grant
    Filed: September 26, 2002
    Date of Patent: March 16, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Lahr
  • Publication number: 20040019243
    Abstract: A method of manufacture of 3,5-bis(trifluoromethyl)bromobenzene, comprising the addition of a brominating reagent to a mixture of 3,5-bis(trifluoromethyl)benzene together with at least one of sulphuric acid or oleum in the absence of acetic acid. A method of production of 3,5-bis(trifluoromethyl)acetophenone comprising the reaction of 3,5-bis(trifluoromethyl)phenyl magnesium bromide with acetyl chloride in the presence of cuprous chloride. A method of production of 3,5-bis(trifluoromethyl)acetophenone comprising the steps of reacting 3,5-bis(trifluoromethyl)phenyl magnesium bromide with acetic anhydride, adding water, and recovering the product by azeotropic distillation. A method of removal of impurities including 3,5-bis(trifluoromethyl)acetate, 4-bromobutyl acetate and 4-chlorobutyl acetate from a preparation of 3,5-bis(trifluoromethyl)acetophenone, the method comprising heating the 3,5-bis(trifluoromethyl)acetophenone with a dilute solution of alkali.
    Type: Application
    Filed: July 21, 2003
    Publication date: January 29, 2004
    Inventors: Peter David Nightingale, Reginald Barry O'Neill, Robert Rhodes
  • Patent number: 6653515
    Abstract: &agr;,&bgr;,&bgr;-Trifluorostyrene and derivatives thereof synthesized in two steps from 1,1,1,2-tetrafluoroethylene. In the first step, 1,1,1,2-tetrafluoroethylene is reacted with a base, a metal salt such as zinc chloride and an optionally amine to form a trifluorovinyl metal complex. In the second step, the trifluorostyrene or derivative is obtained by reacting the trifluorovinyl metal complex with an aryl transfer agent such as, for example, an aryl triflate or an aryl halide, in the presence of a metal catalyst and optionally a coordinating ligand. Both steps may be carried out in one reactor.
    Type: Grant
    Filed: December 14, 2001
    Date of Patent: November 25, 2003
    Assignee: Ballard Power Systems Inc.
    Inventors: Charles Stone, Timothy J. Peckham, Donald J. Burton, Anilkumar Raghavanpillai