Oxygen Containing Patents (Class 570/142)
  • Publication number: 20080125589
    Abstract: It was found that a fluoro derivative can be produced by reacting a hydroxy derivative with sulfuryl fluoride (SO2F2) in the presence of an organic base or in the presence of an organic base and “a salt or complex comprising an organic base and hydrogen fluoride”. According to the present production process, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in industrial use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, specifically 4-fluoroproline derivatives, 2?-deoxy-2?-fluorouridine derivatives, optically-active ?-fluorocarboxylate derivatives, and the like, even in a large scale.
    Type: Application
    Filed: March 17, 2006
    Publication date: May 29, 2008
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Akihiro Ishii, Takashi Ootsuka, Manabu Yasumoto, Hideyuki Tsuruta, Kenjin Inomiya, Koji Ueda, Kaori Mogi
  • Patent number: 7378194
    Abstract: The invention concerns novel ionic compounds with low melting point whereof the onium type cation having at least a heteroatom such as N, O, S or P bearing the positive charge and whereof the anion includes, wholly or partially, at least an ion imidide such as (FX1O)N?(OX2F) wherein X1 and X2 are identical or different and comprise SO or PF, and their use as solvent in electrochemical devices. Said composition comprises a salt wherein the anionic charge is delocalised, and can be used, inter alia, as electrolyte.
    Type: Grant
    Filed: October 1, 2004
    Date of Patent: May 27, 2008
    Assignees: ACEP, Inc., Centre de la Recherche Scientifique, Universite de Montreal
    Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Nathalie Ravet
  • Patent number: 7364908
    Abstract: A method of separating at least a first non-fluorous compound from a mixture of compounds including at least the first non-fluorous compound and a second fluorous compound includes: charging the of compounds to a non-fluorous solid (stationary) phase and eluting with a fluorous eluting fluid (mobile phase). In one embodiment, the non-fluorous solid phase is polar in nature. The method can further include a second phase elution with a suitable organic solvent. A method conducting a chemical reaction, includes: mixing at least a first fluorous compound and a second compound, the first fluorous compound differing in fluorous nature from the second compound; exposing the first mixture to conditions to convert at least one of the first fluorous compound and the second compound to give a second mixture containing at least a third compound, charging the second mixture to a non-fluorous solid phase; and eluting with a fluorous fluid.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: April 29, 2008
    Assignees: University of Pittsburgh - Of the Commonwealth System of Higher Education, Fluorous Technologies Inc.
    Inventors: Dennis P. Curran, Masato Matsugi, Marvin S. Yu
  • Patent number: 7312288
    Abstract: Polymerizable fluorinated ester compounds having formulae (1) and (2) are novel wherein R1 is H, methyl or trifluoromethyl, R2 and R3 are H or a monovalent hydrocarbon group, R2 and R3 may form a ring, R4 is H, OH or a monovalent hydrocarbon group, and R5 is an acid labile group.
    Type: Grant
    Filed: October 6, 2004
    Date of Patent: December 25, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Takeru Watanabe
  • Patent number: 7282246
    Abstract: Concerning the compound of the formula (I) R1, R3 are each independently, for example, H R2, R4 are each independently, for example, H X1, X2 are each independently H or F M1 is —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CF2—O—, —O—CF2—, —CH?CH—, —CF?CF—, —C?C—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2—, —CH2—CH2—, —CF2—CF2—, —(CH2)4—, —OC(?O)CF?CF— or a single bond A1 is, for example, 1,4-phenylene, and R5 has the same possible definitions as specified for R2 and R4, with the exception of —M1-A1-R5, but independently of the particular definitions of R2 and R4 with the following provisos: 1) at least one of X1, X2 has to be F 2) R1, R2, R3 and R4 must not at the same time be H 3) at most two of R1, R2, R3 and R4 may be c).
    Type: Grant
    Filed: April 4, 2005
    Date of Patent: October 16, 2007
    Assignee: Merck Patent GmbH
    Inventors: Wolfgang Schmidt, Barbara Hornung, Rainer Wingen
  • Patent number: 7230147
    Abstract: The invention concerns a method for functionalizing a double bond and, more particularly, a double bond bearing a metalloid atom. Said functionalization is produced by the action of perhalogenated sulphonyl chloride on the carbon bearing sulphur in the presence of a free radical initiator, preferably by homolytic cleavage. The invention is useful in organic synthesis.
    Type: Grant
    Filed: June 11, 2004
    Date of Patent: June 12, 2007
    Assignee: Shasun Pharma Solutions Limited
    Inventor: Nicolas Roques
  • 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: 7030283
    Abstract: This invention relates to a process for the preparation of 1,1-difluoroolefins, e.g., difluorovinyl cycloaliphatic compounds such as difluorovinylcyclohexane and derivatives by the dehydrofluorination of a trifluoromethyl-substituted cycloaliphatic compound and the resulting compositions. This method utilizes a “sterically hindered super-base” system represented by the formula M+?NRR?; where M is Na or K and R is a secondary, or tertiary alkyl or cycloalkyl group of amines for effecting dehydrofluorination of the trifluoromethyl group leading to the difluorovinyl based cycloaliphatic compounds. The sterically hindered super base can be formed by the, in situ, reaction of a sodium or potassium alkoxide, e.g., KtBuO with a lithium dialkylamide where the lithium is bonded to nitrogen atom of an amine bearing secondary or tertiary aliphatic groups.
    Type: Grant
    Filed: January 23, 2004
    Date of Patent: April 18, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Kathryn Sue Hayes, Guido Peter Pez
  • Patent number: 7026520
    Abstract: Methane is used as the selective dehydrating agent for the production of 2,3,3,3-tetrafluoro-1-propene (R1234yf) from 2,2,3,3,3-pentafluoro-1-propanol. Supported transition metal catalysts are prepared and used for this reaction with high activity. Almost 58% selectivity to R1234yf is obtained at an alcohol conversion level of 60% using unsupported Ni-mesh as the catalyst. Pd and Pt show almost similar level of conversion; however, the selectivity to the desired product is low. The activity of the metal catalyst was found to be a function of the type of support material, activated carbon showing better activity than alumina. Different important process parameters such as temperature, pressure, and contact time are studied to optimize the process. High pressure and temperature are deleterious to the rate of 1234yf formation; yet, the highest yield to 1234yf is obtained while performing a reaction at 494° C. with a contact time of 23 sec.
    Type: Grant
    Filed: December 8, 2004
    Date of Patent: April 11, 2006
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, HsuehSung Tung, Haridasan K. Nair
  • Patent number: 6992229
    Abstract: The present invention has an object to provide a method for purifying a fluorinated hydroxyl compound of the formula 1 safely in a high yield under industrially practical conditions. Namely, a mixture containing a fluorinated hydroxyl compound of Rf—CR1R2—OH (Formula 1, wherein Rf is a C1-20 polyfluoroalkyl group, and each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group) such as 2,2,3,3-tetrafluoropropanol, and a compound having an unshared electron pair, is distilled by heating in the presence of a solid acid catalyst such as a cation exchange resin catalyst, or by adding a proton source such as water.
    Type: Grant
    Filed: November 19, 2002
    Date of Patent: January 31, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Hidekazu Okamoto, Akihiro Wada, Toshihiko Toma, Nobuyuki Yamagishi
  • Patent number: 6919480
    Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.
    Type: Grant
    Filed: December 5, 2003
    Date of Patent: July 19, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • Patent number: 6897344
    Abstract: Divalent and trivalent metal salts are added to the solution containing the fluorine compound to precipitate the layered double hydroxide containing the fluorine compound between layers. By these processes, the fluorine compound can be fixed with high rate. Moreover, if necessary, the precipitated layered double hydroxide can be recovered to separate the fluorine compound or its salt between layers. Therefore, the burden to environment or the ecosystem by the fluorine compound can be reduced.
    Type: Grant
    Filed: July 26, 2001
    Date of Patent: May 24, 2005
    Assignee: Jemco Inc.
    Inventors: Kiyoshi Fuda, Toshiaki Matsunaga, Takeshi Kamiya, Kota Omori
  • Patent number: 6894197
    Abstract: A method for producing fluorinated alcohols from fluorinated alkyl halides can produce fluorinated alcohols at high product yield and at high selectivity in a single-step reaction. The method eliminates the need to use heavy metals and other toxic compounds that are difficult to handle or process. Specifically, the method produces a fluorinated alcohol represented by the following general formula (2): Rf(A)OH??(2) wherein Rf represents a perfluoroalkyl group having 1 to 10 carbon atoms; and A represents a straight-chained or branched saturated hydrocarbon group having 3 to 10 carbon atoms. The method is characterized in that it allows a fluorinated alkyl halide represented by the following general formula (1) to react with an alkali metal salt of 4-hydroxybutyrate in a gamma-butyrolactone solvent: Rf(A)X??(1) wherein Rf and A are as defined above; and X represents a halogen atom.
    Type: Grant
    Filed: July 1, 2002
    Date of Patent: May 17, 2005
    Assignee: Tosoh F-Tech, Inc.
    Inventors: Hideyuki Mimura, Kosuke Kawada, Shoji Arai
  • 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
  • Patent number: 6861565
    Abstract: A process for producing a fluoroalkanol which can easily be industrially practiced with high selectivity, is provided. CHR1R2OH, a radical initiator and CF2?CFRf are continuously supplied and reacted at from 105 to 135° C., and H—(RfCFCF2)n—CR1R2—OH formed, is continuously discharged. Here, each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group, Rf is a fluorine atom or a C1-4 polyfluoroalkyl group, and n is an integer of from 1 to 4.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: March 1, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Toshihiko Tohma, Akihiro Wada
  • Patent number: 6841304
    Abstract: The invention concerns novel ionic compounds with low melting point whereof the onium type cation having at least a heteroatom such as N, O, S or P bearing the positive charge and whereof the anion includes, wholly or partially, at least an ion imidide such as (FX1O)N?(OX2F) wherein X1 and X2 are identical or different and comprise SO or PF, and their use as solvent in electrochemical devices. Said composition comprises a salt wherein the anionic charge is delocalised, and can be used, inter alia, as electrolyte.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: January 11, 2005
    Assignees: ACEP, Inc., Centre National de la Recherche Scientifique, Universite de Montreal
    Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Nathalie Ravet
  • Patent number: 6825043
    Abstract: A method of increasing the fluorous nature of a compound includes the step of reacting the compound with at least one second compound having the formula: wherein Rf is a fluorous group, Rs is a spacer group, d is 1 or 0, m is 1, 2 or 3, Ra is an alkyl group and X is a suitable leaving group. A compound has the formula: wherein Rf is a fluorous group, n is an integer between 0 and 6, m is 1, 2 or 3, Ra is an alkyl group and X is a leaving group.
    Type: Grant
    Filed: May 5, 2000
    Date of Patent: November 30, 2004
    Assignee: University of Pittsburgh
    Inventors: Dennis P. Curran, Roger Read, Zhiyong Luo
  • 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: 6747174
    Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: June 8, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • Patent number: 6743957
    Abstract: Divalent and trivalent metal salts are added to the solution containing the fluorine compound and the polymer containing fluorine to precipitate the layered double hydroxide containing the fluorine compound between layers. At this time, the polymer containing fluorine suspended in the solution is also coagulated to precipitate. By these processes, the fluorine compound is fixed with high rate to separate from the solution with the polymer containing fluorine, and recovered if necessary. By this treatment process, the fluorine compound and the polymer containing fluorine, contained in the wastewater etc. can be separated easily, and the burden to environment or ecosystem can be reduced.
    Type: Grant
    Filed: June 26, 2002
    Date of Patent: June 1, 2004
    Assignee: JEMCO, Inc.
    Inventors: Kiyoshi Fuda, Toshiaki Matsunaga, Takeshi Na Kamiya, Kota Omori
  • Publication number: 20040024269
    Abstract: It is to provide a process for synthesizing an intended fluorine-containing compound having a geminal difluoro structure with a high yield, by subjecting a carbonyl compound which is readily available to a two-stage reaction.
    Type: Application
    Filed: July 30, 2003
    Publication date: February 5, 2004
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventors: Shuzhong Wang, Kazuhiko Hayashi, Shinsuke Kaga, Kazuya Oharu
  • Patent number: 6670511
    Abstract: A fluorine-containing diene represented by the formula 1: CF2═CF(CF2)nCXYOCF═CF2  Formula 1 wherein each of X and Y which are independent of each other, is an atom selected from a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, provided that X and Y are not simultaneously hydrogen atoms or fluorine atoms, and n is an integer of from 1 to 3.
    Type: Grant
    Filed: May 15, 2002
    Date of Patent: December 30, 2003
    Assignee: Asahi Glass Company Limited
    Inventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
  • Publication number: 20030135075
    Abstract: A two-step process for the preparation of fluoroolefin compounds of formula I 1
    Type: Application
    Filed: October 21, 2002
    Publication date: July 17, 2003
    Inventor: William Wakefield Wood
  • Patent number: 6590125
    Abstract: A light-emitting polymer and its preparation method, the polymer being excellent in electron injection and transport ability as well as hole injection and transport ability in an EL device, the EL device manufactured from the polymer being also emittable in the blue emission region, in which the EL device from an inorganic material is not mostly emittable. The light-emitting polymer of the invention is an alternated copolymer having repeated units (arylenevinylene units) excellent in hole injection and transport ability and repeated units (fluorinated tetraphenyl units) excellent in electron injection and transport ability with alternated order, as shown in formula (II). An EL device manufactured from the light-emitting polymer, a fluorinated tetraphenyl derivative of formula (I), which is used as a monomer to prepare the light-emitting polymer, and their preparation methods.
    Type: Grant
    Filed: April 3, 2001
    Date of Patent: July 8, 2003
    Assignee: Electronics and Telecommunications Research Institute
    Inventors: Do Hoon Hwang, Tae Hyoung Zyung, Lee Mi Do, Hye Yong Chu
  • Patent number: 6534671
    Abstract: This invention relates to a novel class of halofluorinated acrylates and more particularly to chlorofluorinated or bromofluorinated acrylates characterized by a chlorofluorinated or bromofluorinated alkylene moiety with acrylate functions at both terminals. These chlorofluorinated acrylates may be photocured in the presence of a photoinitiator into transparent polymers useful as optical waveguiding materials.
    Type: Grant
    Filed: June 13, 2001
    Date of Patent: March 18, 2003
    Assignee: Corning Incorporated
    Inventors: Chengjiu Wu, Baopei Xu, Jianhui Shan, James T. Yardley
  • Patent number: 6448452
    Abstract: A polymer which contains monomer units formed by polymerization of a fluorine-containing diene of formula 1: CF2═CF(CF2)nCXYOCF═CF2 Wherein X and Y are hydrogen and chlorine, hydrogen and-bromine, hydrogen and iodine, fluorine and chlorine, fluorine and bromine, fluorine and iodine, chlorine and bromine, chlorine and iodine, bromine and bromine, bromine and iodine, or iodine and iodine and n is an integer from 1 to 3.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: September 10, 2002
    Assignee: Asahi Glass Company Limited
    Inventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
  • Publication number: 20020055045
    Abstract: The invention concerns novel ionic compounds with low melting point whereof the onium type cation having at least a heteroatom such as N, O, S or P bearing the positive charge and whereof the anion includes, wholly or partially, at least an ion imidide such as (FX1O)N−(OX2F) wherein X1 and X2 are identical or different and comprise SO or PF, and their use as solvent in electrochemical devices. Said composition comprises a salt wherein the anionic charge is delocalised, and can be used, inter alia, as electrolyte.
    Type: Application
    Filed: November 9, 2001
    Publication date: May 9, 2002
    Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Nathalie Ravet
  • Patent number: 6365301
    Abstract: The invention concerns novel ionic compounds with low melting point whereof the onium type cation having at least a heteroatom such as N, O, S or P bearing the positive charge and whereof the anion includes, wholly or partially, at least an ion imidide such as (FX1O)N−(OX2F) wherein X1 and X2 are identical or different and comprise SO or PF, and their use as solvent in electrochemical devices. Said composition comprises a salt wherein the anionic charge is delocalized, and can be used, inter alia, as electrolyte.
    Type: Grant
    Filed: September 7, 1999
    Date of Patent: April 2, 2002
    Assignees: ACEP, Inc., Centre National de la Recherche Scientifique, Universite de Montreal
    Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Nathalie Ravet
  • Patent number: 6313359
    Abstract: A method of producing hydrofluorocarbons and methods of producing other commercially attractive compounds formed as by-products of hydrofluorocarbon production by using aldehydes as a principal reactant.
    Type: Grant
    Filed: July 17, 2000
    Date of Patent: November 6, 2001
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Robert Scott Wedinger
  • Publication number: 20010034459
    Abstract: The invention relates to a process for preparing a compound of the formula (I) 1
    Type: Application
    Filed: December 21, 2000
    Publication date: October 25, 2001
    Inventors: Andreas Meudt, Stefan Scherer, Antje Norenberg, Peter Koch, Steffen Haber
  • Patent number: 6248889
    Abstract: A process for preparing a fluoride from its corresponding alcohol comprises the steps of (a) forming a mixture comprising (i) at least one fluorinated, saturated aliphatic or alicyclic sulfonyl fluoride (for example, perfluorobutanesulfonyl fluoride) and (ii) at least one primary or secondary alcohol; and (b) adding a molar excess of at least one strong, aprotic, non-nucleophilic, hindered, double bond-containing, organic base (for example, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) to the mixture.
    Type: Grant
    Filed: November 20, 1998
    Date of Patent: June 19, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Patricia M. Savu, Daniel C. Snustad
  • Patent number: 6242645
    Abstract: Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating agents are disclosed.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: June 5, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Guido Peter Pez, Reno Joseph Pesaresi, Jr., Robert George Syvret
  • Patent number: 6235949
    Abstract: A process for the preparation of halide compounds, preferably aryl halides, by contacting a gaseous mixture of hydrohalic acid and a compound selected from an aryl halogen formate, an aryl carbonate and equivalents thereof with a Lewis acid catalyst.
    Type: Grant
    Filed: March 10, 1997
    Date of Patent: May 22, 2001
    Assignee: Rhodia Chimie
    Inventors: Herve Garcia, Laurent Gilbert, Serge Ratton, Christophe Rochin
  • Patent number: 6235950
    Abstract: A method of producing hydrofluorocarbons and methods of producing other commercially attractive compounds formed as by-products of hydrofluorocarbon production by using ketones as a principal reactant.
    Type: Grant
    Filed: December 22, 1999
    Date of Patent: May 22, 2001
    Assignee: Honeywell International
    Inventors: Hsueh S. Tung, Robert S. Wedinger
  • Patent number: 6222064
    Abstract: A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: April 24, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Guido Peter Pez
  • Patent number: 6207860
    Abstract: Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating agents are disclosed.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: March 27, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Guido Peter Pez, Reno Joseph Pesaresi, Jr.
  • Patent number: 6194606
    Abstract: The present invention provides compounds having the formula: in which R is hydrogen or C1-C4alkyl, preferably hydrogen and Y is hydrogen, C1-C4alkyl, C1-C4alkoxy, CF3, halogen (F, Cl, Br or I) or SO3M in which M is H, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C1-C4alkylammonium, mono-, di- or tri-hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C1-C4alkyl and C1-C4hydroxyalkyl groups; a process for their production; and their use as intermediates in the production of asymmetric or symmetric fluorescent whitening agents.
    Type: Grant
    Filed: September 22, 1998
    Date of Patent: February 27, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Bernd Siebenhaar, Bruno Casagrande, Victor Eliu
  • Patent number: 6191326
    Abstract: This invention provides a process for preparing 1,1,1,2,3,3,3-heptafluoropropane, which comprises reacting 2-trifluoromethyl-3,3,3-trifluoropropionic acid with fluorine gas. The process according to this invention produces 1,1,1,2,3,3,3-heptafluoropropane with high selectivity and is an industrially efficient and economical method.
    Type: Grant
    Filed: September 3, 1999
    Date of Patent: February 20, 2001
    Assignee: Daikin Industries, Inc.
    Inventors: Tatsuya Otsuka, Hirokazu Aoyama
  • Patent number: 6118032
    Abstract: Disclosed is a process for the production of cyclopropylmethyl halides (CPMX) such as cyclopropylmethyl chloride (CPMCI) and cyclopropylmethyl bromide (CPMBr) wherein cyclopropanemethanol (CPMO) is contacted with a complex comprising a dialkyl sulfide and an N-halosuccinimide in the presence of an organic solvent.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: September 12, 2000
    Assignee: Eastman Chemical Company
    Inventors: Daniel John Bayston, Ronald Michael Scott, James Matthew Lovell, Lindsay Anne White
  • Patent number: 6111151
    Abstract: Process for removing water from compositions containing water, organics and hydrogen fluoride (e.g. product stream from vapour phase hydrofluorination processes, e.g. manufacture of HFA 134a, HFA 125 or HFA 32) by phase separation and purge of the aqueous layer.
    Type: Grant
    Filed: February 8, 1999
    Date of Patent: August 29, 2000
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul Nicholas Ewing, Paul David Bernard Bujac, David William Bonniface
  • Patent number: 6077981
    Abstract: Disclosed is a process for the production of cyclopropylmethyl halides (CPMX) such as cyclopropylmethyl chloride (CPMCl) and cyclopropylmethyl bromide (CPMBr) wherein cyclopropanemethanol (CPMO) is contacted with an aqueous solution of a hydrogen halide (HX) at a temperature in the range of -30.degree. C. to 35.degree. C. Also disclosed is a three-step process wherein CPMO is converted to a CPMX, the CPMX is separated as a liquid organic phase from the aqueous hydrogen halide by decantation and then is subjected to fractional distillation to provide CPMX in high purity. Finally, a process for the co-production of a CPMX and a cyclobutyl halide (CBX) is disclosed.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: June 20, 2000
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Colin Henry Ridyard, Daniel Latham Terrill, Clyde Neil Clubb
  • Patent number: 6002055
    Abstract: Highly fluorinated epoxides are reacted with dihalogens in the presence of metal and metal containing reaction promoters to give dihalofluoromethanes and their homologues.
    Type: Grant
    Filed: August 19, 1998
    Date of Patent: December 14, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Zhen-Yu Yang
  • Patent number: 5994599
    Abstract: A process is disclosed for preparing an adduct of the formula R.sup.1 CF.sub.2 CH.sub.2 OCF.sub.3-a-m (C.sub.2 H.sub.n X.sub.4-n F).sub.m R.sup.2.sub.a wherein R.sup.1 is selected from the group consisting of --(CF.sub.2).sub.p H and --C.sub.p F.sub.2p+1 where p is 0 or an integer from 1 to 6; R.sup.2 is selected from the group consisting of --H, --CHF.sub.2, --CHFCF.sub.3, --CHFOCF.sub.3, --CHFO(CF.sub.2).sub.2 CF.sub.3, and --CHClF; each X is independently selected from the group consisting of Br, Cl and F; a is 0 or 1; m is 1 or 2, provided that when a is 1 and R.sup.2 is other than hydrogen, then m is 1; and n is 0, 1 or 2. The process involves reacting a fluorinated ether of the formula R.sup.1 CF.sub.2 CH.sub.2 OCF.sub.3-a R.sup.2.sub.a with an olefin of the formula C.sub.2 H.sub.n X.sub.4-n in the liquid phase in the presence of antimony pentafluoride catalyst. Also disclosed is a process for preparing unsaturated ethers of the formula R.sup.1 CF.sub.2 CH.sub.2 OCF.sub.3-a-m (C.sub.2 H.sub.n X.sub.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: November 30, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Viacheslav Alexandrovich Petrov
  • Patent number: 5910615
    Abstract: A process is disclosed for producing 1,1,1,3,3,3-hexafluoropropane and/or 1,1, 1,3,3-pentafluoropropene from (CF.sub.3).sub.2 CHCOOH and/or its water soluble salts. The process involves providing a mixture containing water and such carboxy compound(s) which has a pH of less than about 4, and reacting the mixture at a temperature of at least about 75.degree. C. Certain ether compounds may be included in the mixture along with (CF.sub.3).sub.2 CHCOOH and/or its water soluble salts. The reaction of the carboxy (and optionally ether) compound(s) with water may be employed in connection with a process for producing tetrafluoroethylene and/or hexafluoropropylene by pyrolysis, where by-product perfluoroisobutylene is reacted with water (and optionally an alkanol) to produce (CF.sub.3).sub.2 CHCOOH (and optionally one or more ether compounds).
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: June 8, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Scott C. Jackson, Paul Raphael Resnick, Steven H. Swearingen
  • Patent number: 5905176
    Abstract: Disclosed is a process for the production of cyclobutyl halides such as cyclobutyl chloride and cyclobutyl bromide wherein cyclopropanemethanol is contacted with an aqueous solution of a hydrogen halide at a temperature in the range of greater than 35.degree. C. up to 120.degree. C.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: May 18, 1999
    Assignee: Eastman Chemical Company
    Inventor: Shaowo Liang
  • Patent number: 5874655
    Abstract: Chlorinated aromatics are obtained in a simple manner and in particularly good yield if the corresponding chloroformic esters are heated in the liquid phase to 90.degree. to 240.degree. C. in the presence of an inert organic solvent and a catalytic amount of one or more Lewis acids selected from the group consisting of the aluminium halides, iron halides and antimony halides.
    Type: Grant
    Filed: March 6, 1997
    Date of Patent: February 23, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Albrecht Marhold
  • Patent number: 5874656
    Abstract: o-Alkylfluorobenzenes are advantageously prepared by heating the corresponding chloroformates to from 70.degree. to 200.degree. C. in the liquid phase in the presence of hydrogen fluoride and in the presence of an inert diluent other than a halogenated alkane.
    Type: Grant
    Filed: October 7, 1997
    Date of Patent: February 23, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Michael-Harold Rock
  • Patent number: 5763702
    Abstract: A benzene halide is produced with high purity at a high yield by heating a halogen-substituted benzene carboxylic acid in the presence of a basic catalyst in a solvent.
    Type: Grant
    Filed: September 25, 1996
    Date of Patent: June 9, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yasunori Okumura, Osamu Kaieda
  • Patent number: 5756868
    Abstract: A process for the production of hydrofluorocarbons, in particular hydrofluoroalkanes such as difluoromethane, which comprises contacting an .alpha.-fluoro-ether, in particular a fluorinated dialkyl ether such as bis(fluoromethyl)ether in the liquid phase with a Lewis acid such as a fluoride of Nb, Sb, B, Ta, Al or Ti.
    Type: Grant
    Filed: October 19, 1995
    Date of Patent: May 26, 1998
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie Burgess, Thomas Anthony Ryan, Richard Llewellyn Powell
  • Patent number: 5750807
    Abstract: A process for the production of a hydro(halo)fluorocarbon which comprises heating an .alpha.-fluoroether in the vapor phase at elevated temperature. .alpha.-fluoroethers are obtained by reacting a non-enolisable aldehyde with hydrogen fluoride to form an intermediate and reacting the intermediate with an alcohol or a halogenating agent. Novel .alpha.-fluoroethers are also provided.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: May 12, 1998
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie Burgess, Jane Lesley Butcher, Thomas Anthony Ryan, Peter Paul Clayton