Fluorine Containing Patents (Class 568/842)
  • Patent number: 10717693
    Abstract: The present invention provides a method for producing a diol having a specific structure in high yields while keeping high selectivity. Provided is a method for producing a diol having a specific structure by oxidizing an olefin having a specific structure in the presence of a ruthenium compound.
    Type: Grant
    Filed: November 22, 2016
    Date of Patent: July 21, 2020
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Tomohito Hamada, Michiaki Okada, Akinori Yamamoto, Yosuke Kishikawa
  • Patent number: 8975448
    Abstract: Process for preparing 2,2-difluoroethanol, comprising the following steps: reacting 1-chloro-2,2-difluoroethane with an alkali metal salt of formic acid or acetic acid in a suitable solvent to give the corresponding 2,2-difluoroethyl formate or 2,2-difluoroethyl acetate, and transesterifying the 2,2-difluoroethyl formate or 2,2-difluoroethyl acetate from step (i) in the presence of an alcohol and optionally of a base.
    Type: Grant
    Filed: July 16, 2012
    Date of Patent: March 10, 2015
    Assignee: Bayer Intellectual Property GmbH
    Inventors: Thomas Norbert Müller, Norbert Lui, Stefan Moczarski
  • Patent number: 8889888
    Abstract: A fluorine-containing sulfonic acid salt or a compound having a fluorine-containing sulfonic acid group, either of which having a structure represented by the following general formula (1), is provided. Such a salt or compound can act as a suitable photo-acid generator, and can form a resist pattern having excellent sensitivity, resolution and mask-dependence. [In general formula (1), R represents a substituted or unsubstituted linear or branched monovalent hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted monovalent hydrocarbon group having 3 to 30 carbon atoms and a cyclic or a partially cyclic structure, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic organic group having 4 to 30 carbon atoms.
    Type: Grant
    Filed: July 6, 2009
    Date of Patent: November 18, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Masashi Nagamori, Masaki Fujiwara, Kazunori Mori, Satoru Narizuka
  • Patent number: 8865947
    Abstract: The present invention is directed to a process for preparation of fluorinated alcohols of Formula (I) RfCH2CH2OH??(I) by contacting a fluorinated iodide with an alkyl vinyl ether in the presence of an initiator and a base to generate an intermediate hemi-acetal or aldehyde or a mixture thereof, followed by hydrogenation of the hemi-acetal of Formula (II) RfCH2CH(OCxH2x+1)m(OH)p??(II) or aldehyde of Formula (III) RfCH2CHO??(III) or a mixture thereof, to yield a compound of Formula (I).
    Type: Grant
    Filed: December 6, 2012
    Date of Patent: October 21, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Kenneth Gene Moloy, Sheng Peng
  • Publication number: 20140243561
    Abstract: Process for preparing 2,2-difluoroethanol, comprising the following steps: reacting 1-chloro-2,2-difluoroethane with an alkali metal salt of formic acid or acetic acid in a suitable solvent to give the corresponding 2,2-difluoroethyl formate or 2,2-difluoroethyl acetate, and transesterifying the 2,2-difluoroethyl formate or 2,2-difluoroethyl acetate from step (i) in the presence of an alcohol and optionally of a base.
    Type: Application
    Filed: July 16, 2012
    Publication date: August 28, 2014
    Applicant: BAYER INTELLECTUAL PROPERTY GMBH
    Inventors: Thomas Norbert Mueller, Norbert Lui, Stefan Moczarski
  • Publication number: 20140163262
    Abstract: The present invention is directed to a process for preparation of fluorinated alcohols of Formula (I) RfCH2CH2OH??(I) by contacting a fluorinated iodide with an alkyl vinyl ether in the presence of an initiator and a base to generate an intermediate hemi-acetal or aldehyde or a mixture thereof, followed by hydrogenation of the hemi-acetal of Formula (II) RfCH2CH(OCxH2x+1)m(OH)p??(II) or aldehyde of Formula (III) RfCH2CHO??(III) or a mixture thereof, to yield a compound of Formula (I).
    Type: Application
    Filed: December 6, 2012
    Publication date: June 12, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: KENNETH GENE MOLOY, Sheng Peng
  • Patent number: 8748672
    Abstract: By using an organic base when a carboxylic acid bromodifluoroethyl ester is sulfinated by using a sulfinating agent, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt. By oxidizing the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt. By using the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt as a raw material and exchanging it into an onium salt directly or through saponification/esterification, there can be obtained a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid onium salt.
    Type: Grant
    Filed: July 5, 2013
    Date of Patent: June 10, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
  • Patent number: 8729316
    Abstract: A process for preparing a fluorinated diol compound by reacting the corresponding ketone-alcohol or aldehyde-alcohol with hydrogen over a palladium catalyst in the vapor phase.
    Type: Grant
    Filed: February 16, 2012
    Date of Patent: May 20, 2014
    Assignee: Halocarbon Products Corporation
    Inventors: Paul Mazzell, Jr., Neville Pavri, Joel Swinson
  • Patent number: 8658840
    Abstract: A production method of a ?-fluoroalcohol includes performing a reaction of an ?-fluoroester with hydrogen gas (H2) in the presence of a specific ruthenium complex (i.e. a ruthenium complex of the general formula [2], preferably a ruthenium complex of the general formula [4]). This production method can employ a suitable hydrogen pressure of 1 MPa or less by the use of such a specific ruthenium complex and does not require a high-pressure gas production facility when put in industrial practice. In addition, this production method can remarkably reduce the amount of catalyst used therein (to e.g. a substrate/catalyst ratio of 20,000) in comparison to the substrate/catalyst ratio conventional reduction of ?-fluoroalcohol. It is possible by these reduction in hydrogen pressure and catalyst amount to largely reduce the production cost of the ?-fluoroalcohol.
    Type: Grant
    Filed: January 27, 2012
    Date of Patent: February 25, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Takashi Ootsuka, Takehisa Ishimaru, Mari Imamura
  • Publication number: 20130338404
    Abstract: A process for preparing a fluorinated diol compound by reacting the corresponding ketone-alcohol or aldehyde-alcohol with hydrogen over a palladium catalyst in the vapor phase.
    Type: Application
    Filed: February 16, 2012
    Publication date: December 19, 2013
    Applicant: HALOCARBON PRODUCTS CORPORATION
    Inventors: Paul Mazzell, JR., Neville Pavri, Joel Swinson
  • Publication number: 20130303774
    Abstract: A production method of a ?-fluoroalcohol includes performing a reaction of an ?-fluoroester with hydrogen gas (H2) in the presence of a specific ruthenium complex (i.e. a ruthenium complex of the general formula [2], preferably a ruthenium complex of the general formula [4]). This production method can employ a suitable hydrogen pressure of 1 MPa or less by the use of such a specific ruthenium complex and does not require a high-pressure gas production facility when put in industrial practice. In addition, this production method can remarkably reduce the amount of catalyst used therein (to e.g. a substrate/catalyst ratio of 20,000) in comparison to the substrate/catalyst ratio conventional reduction of ?-fluoroalcohol. It is possible by these reduction in hydrogen pressure and catalyst amount to largely reduce the production cost of the ?-fluoroalcohol.
    Type: Application
    Filed: January 27, 2012
    Publication date: November 14, 2013
    Applicant: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Takashi Ootsuka, Takehisa Ishimaru, Mari Imamura
  • Patent number: 8581009
    Abstract: By using an organic base when a carboxylic acid bromodifluoroethyl ester is sulfinated by using a sulfinating agent, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt. By oxidizing the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt. By using the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt as a raw material and exchanging it into an onium salt directly or through saponification/esterification, there can be obtained a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid onium salt.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: November 12, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
  • Patent number: 8558033
    Abstract: The problem to be resolved by the present invention is to provide a method for efficiently synthesizing optically active lower aliphatic alcohols that have difficulty in separation from organic solvents, without using a special reactor. The present invention relates to a method for producing an optically active aliphatic alcohol having a fluorine atom at ? position, wherein an optically active alcohol is produced by reacting an aliphatic ketone having a fluorine atom at ? position in water using a formate, under the presence of an asymmetric catalyst represented by general formula (1) and an acid.
    Type: Grant
    Filed: June 28, 2011
    Date of Patent: October 15, 2013
    Assignee: Kanto Kagaku Kabushiki Kaisha
    Inventors: Takeaki Katayama, Toshihide Takemoto, Kunihiko Murata
  • Patent number: 8487141
    Abstract: To provide a method for producing a perfluoro compound having hydroxyl groups, whereby agglomeration of a reduction reaction intermediate tends not to occur during a reduction reaction, and a perfluoro compound having —C(?O)OH can be used as a starting material. Reducing (A-C(?O)=Q=)nRfn in the presence of a metal hydride and an inorganic salt of lithium in an alcohol solvent to obtain (B—CH(OH)-Q-)n-m(A-C(?O)-Q-)mRfn, wherein A is a hydroxyl group, a C1-5 alkoxy group, a hydrogen atom, a C1-5 alkyl group or the like, Q is a perfluoroalkylene group or the like, n is an integer of at least 1, m is an integer at least 0 and less than n, Rfn is an n valent perfluoro saturated hydrocarbon group or the like, and B is a group depending on A wherein when A is a hydroxyl group, a C1-5 alkoxy group or the like, B is a hydrogen atom, and when A is a hydrogen atom, a C1-5 alkyl group or the like, B is the same group as A.
    Type: Grant
    Filed: March 2, 2011
    Date of Patent: July 16, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Daisuke Shirakawa, Yoshiyuki Gozu, Yoshitomi Morisawa
  • Patent number: 8481774
    Abstract: Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH2R9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.
    Type: Grant
    Filed: October 2, 2009
    Date of Patent: July 9, 2013
    Assignee: Nippon Soda Co., Ltd.
    Inventor: Yasuhiro Miyashita
  • Publication number: 20130012740
    Abstract: A production method of difluoroacetyl chloride according to the present invention includes a chlorination step of bringing a raw material containing at least either a 1-alkoxy-1,1,2,2-tetrafluoroethane or difluoroacetyl chloride into contact with calcium chloride at a reaction enabling temperature. A production method of 2,2-difluoroethyl alcohol according to the present invention includes a catalytic reduction step of causing catalytic reduction of the difluoroacetyl chloride obtained by the above production method. By these methods, the difluoroacetyl fluoride can be efficiently converted to the difluoroacetyl chloride and to the 2,2-difluoroethyl alcohol.
    Type: Application
    Filed: March 16, 2011
    Publication date: January 10, 2013
    Applicant: Central Glass Company ,Limited
    Inventors: Masamune Okamoto, Hideaki Imura, Naoto Takada
  • Patent number: 8304576
    Abstract: Halogenated ?-fluoroethers (or bis-derivatives thereof) can be produced by reacting a halogenated hemiacetal (or bis-derivative thereof) with sulfuryl fluoride (SO2F2) in the presence of an organic base. The reaction is conducted preferably in the presence of “a salt or complex of an organic base with hydrogen fluoride”, whereby the objective dehydroxyfluorination can proceed extremely favorably. It is still preferable to use as the starting substrate a halogenated hemiacetal prepared from fluoral or 3,3,3-trifluoropyruvic acid ester. Thus, industrially important halogenated ?-fluoroethers can be industrially produced with high selectivity and in high yield.
    Type: Grant
    Filed: May 14, 2009
    Date of Patent: November 6, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Manabu Yasumoto
  • Publication number: 20120219596
    Abstract: Compounds according to formula (I) are particularly suitable for the treatment and/or prevention of a medical condition involving hypoxic, anoxic and/or inflamed mammalian tissue. Furthermore, the invention relates to the use of said compounds for preparing a medicament and to pharmaceutical preparations comprising such compounds.
    Type: Application
    Filed: July 27, 2010
    Publication date: August 30, 2012
    Applicants: ETH Zurich, University of Zurich
    Inventors: Ludwig K. Limbach, Inge K. Herrmann, Beatrice Beck-Schimmer, Wendelin J. Stark, Martin Urner
  • Patent number: 8212064
    Abstract: An oligomer of the formula (I): CnF2n+1(CH2)x[(CF2CF2)y(CH2CH2)z]mG??(I) wherein G is an I; OH; OC(O)CH?CH2; OC(O)CCH3?CH2; OC(O)CCl?CH2; NR1H; N3; NCO; SQ wherein Q is H, alkyl, (CH2)nOH, (CH2)nNH2, (CH2)nOC(O)C(Me)=CH2, or (CH2)nNHC(O)C(Me)=CH2; SCN; COOH; SO3H; NHCOCH?CH2; NHCOC(CH3)?CH2); OC(O)NHCH2CH2OC(O)C(CH3)?CH2; or OC(O)NHCH2CH2OC(O)C(CH3)?CH2; subscript n is an integer from 1 to about 6, subscript x is an integer from 1 to about 6, subscripts y, z and m are each independently 1, 2 or 3, or a mixture thereof, the total number of carbons in said formula (I) excluding G ranges from about 8 to about 22, and a process for preparation thereof.
    Type: Grant
    Filed: May 14, 2008
    Date of Patent: July 3, 2012
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Weiming Qiu, Anilkumar Raghavanpillai, Michael Francis Vincent
  • Publication number: 20120136177
    Abstract: Disclosed is a method for producing hexafluoroacetone monohydrate by (1) allowing, in an organic solvent, hexafluoroacetone to be absorbed into water or a hexafluoroacetone hydrate (water addition method) or by (2) an easy method in which a hexafluoroacetone hydrate is mixed with an organic solvent and then distillation is conducted, thereby removing a mixture of water and the organic solvent as a low-boiling-point composition and obtaining a mixture of hexafluoroacetone monohydrate and the organic solvent as a high-boiling-point composition (dehydration method).
    Type: Application
    Filed: July 30, 2010
    Publication date: May 31, 2012
    Applicant: Central Glass Company, Limited
    Inventors: Yutaka Katsuhara, Tatsuya Hayasaka, Mineo Watanabe, Takashi Kume
  • Publication number: 20120107749
    Abstract: There are provided a method of forming a resist pattern, comprising the steps of forming a resist film containing a specific calixarene derivative on a substrate; forming a pattern latent image by selectively exposing the resist film to a high-energy beam; and developing the latent image by removing parts not exposed to the high-energy beam of the resist film with a developer containing at least one fluorine-containing solvent selected form the group consisting of a fluorine-containing alkyl ether and a fluorine-containing alcohol, and the fluorine-containing solvent as a resist developer.
    Type: Application
    Filed: May 20, 2010
    Publication date: May 3, 2012
    Applicant: TOKUYAMA CORPORATION
    Inventors: Seiji Tono, Yuki Chikashige
  • Publication number: 20120083619
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF?CHR from halofluorocarbons of the structure RfCFX2. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(?O)R?.
    Type: Application
    Filed: October 11, 2011
    Publication date: April 5, 2012
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Patent number: 8143440
    Abstract: There is provided a method for separating and collecting at least alcohol with a high purity from an azeotropic mixture of olefin and alcohol.
    Type: Grant
    Filed: January 9, 2009
    Date of Patent: March 27, 2012
    Assignee: Daikin Industries, Ltd.
    Inventors: Yuuki Matsuda, Kazuyoshi Ichihara, Takeomi Hirasaka, Takuya Ichida
  • Patent number: 8110711
    Abstract: Disclosed is a process for producing 2-bromo-2,2-difluoroethanol, which comprises reducing a bromodifluoroacetic acid derivative represented by the formula [1] by using an ate hydride complex as a reducing agent. 2-Bromo-2,2-difluoroethanol thus produced can be used as the starting material to carry out the esterification step, the sulfination step and the oxidation step in this order, thereby producing a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid salt, wherein A represents a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 15 carbon atoms, a heteroaryloxy group having 4 to 15 carbon atoms, or a halogen atom.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: February 7, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Jonathan Joachim Jodry, Masashi Nagamori, Yuji Hagiwara, Masaki Fujiwara, Satoru Narizuka
  • Publication number: 20110319671
    Abstract: The problem to be resolved by the present invention is to provide a method for efficiently synthesizing optically active lower aliphatic alcohols that have difficulty in separation from organic solvents, without using a special reactor. The present invention relates to a method for producing an optically active aliphatic alcohol having a fluorine atom at ? position, wherein an optically active alcohol is produced by reacting an aliphatic ketone having a fluorine atom at ? position in water using a formate, under the presence of an asymmetric catalyst represented by general formula (1) and an acid.
    Type: Application
    Filed: June 28, 2011
    Publication date: December 29, 2011
    Applicant: Kanto Kagaku Kabushiki Kaisha
    Inventors: Takeaki Katayama, Toshihide Takemoto, Kunihiko Murata
  • Publication number: 20110178284
    Abstract: A protective group represented by the following general formula (I) (the oxygen atom attached with * represents oxygen atom of 2?-hydroxyl group of a ribonucleoside, a ribonucleotide or a derivative thereof; R1 and R2 both represent hydrogen atom, or represent a halogen atom, a C1-6 alkyl group, or a C1-6 halo-substituted alkyl group; R3 and R4 represent hydrogen atom, a halogen atom, a C1-6 alkyl group, or a C1-6 halo-substituted alkyl group; and R5 and R6 represent a halogen atom, a C1-6 halo-substituted alkyl group, cyano group, nitro group, or the like), which is stable under the reaction conditions of the nucleic acid synthetic cycles and has little steric hindrance, and can be removed under mild conditions using fluoride ions as a base.
    Type: Application
    Filed: September 15, 2010
    Publication date: July 21, 2011
    Applicant: CHIRALGEN, LTD.
    Inventors: Takeshi WADA, Mamoru SHIMIZU
  • Publication number: 20110178323
    Abstract: Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH2R9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.
    Type: Application
    Filed: October 2, 2009
    Publication date: July 21, 2011
    Applicant: NIPPON SODA CO., LTD.
    Inventor: Yasuhiro Miyashita
  • Patent number: 7902409
    Abstract: Difluoroethanol is produced by hydrogenation, in the presence of an effective amount of a catalyst containing at least one element of Group VIII of the Periodic Table deposited onto a solid, acidic mineral support, of an acetyl halide having the following formula (I), in which formula X is a halogen atom other than a fluorine atom:
    Type: Grant
    Filed: December 19, 2006
    Date of Patent: March 8, 2011
    Assignee: Rhodia Operations
    Inventors: Olivier Buisine, Roland Jacquot
  • Patent number: 7897821
    Abstract: A compound is shown by the following formula (5) in which at least one of Rf groups represents a fluorine atom or a linear or branched perfluoroalkyl group having 1 to 10 carbon atoms, A? represents a substituted or unsubstituted, linear or branched alkylene group having 1 to 20 carbon atoms, an alkylene group having at least one hetero atom, or a single bond, G represents a divalent organic group having a fluorine atom or a single bond, Mm+ represents an onium cation, m represents a natural number of 1 to 3, and p represents a natural number of 1 to 8.
    Type: Grant
    Filed: August 31, 2010
    Date of Patent: March 1, 2011
    Assignee: JSR Corporation
    Inventors: Tomoki Nagai, Eiji Yoneda, Takuma Ebata, Takanori Kawakami, Makoto Sugiura, Tsutomu Shimokawa, Makoto Shimizu
  • Publication number: 20110015431
    Abstract: Disclosed is a process for producing 2-bromo-2,2-difluoroethanol, which comprises reducing a bromodifluoroacetic acid derivative represented by the formula [1] by using an ate hydride complex as a reducing agent. 2-Bromo-2,2-difluoroethanol thus produced can be used as the starting material to carry out the esterification step, the sulfination step and the oxidation step in this order, thereby producing a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid salt, wherein A represents a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 15 carbon atoms, a heteroaryloxy group having 4 to 15 carbon atoms, or a halogen atom.
    Type: Application
    Filed: September 5, 2008
    Publication date: January 20, 2011
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Jonathan Joachim Jodry, Masashi Nagamori, Yuji Hagiwara, Masaki Fujiwara, Satoru Narizuka
  • Patent number: 7795376
    Abstract: A method of isolating a PHA, includes combining the PHA, a first solvent and a second solvent to form a combination, the first solvent being capable of forming an azeotrope with the second solvent; and heating the combination to form the azeotrope of the first and second solvents.
    Type: Grant
    Filed: July 2, 2009
    Date of Patent: September 14, 2010
    Assignee: Metabolix Inc.
    Inventors: Johan Van Walsem, Erik Anderson, John Licata
  • Patent number: 7767866
    Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.
    Type: Grant
    Filed: March 12, 2009
    Date of Patent: August 3, 2010
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Publication number: 20100168480
    Abstract: The present invention provides a method for producing a fluoroalkyl alcohol represented by general formula (6) wherein Rf1 and Rf2 are the same or different, each represents a CF3(CF2)n group (wherein n is an integer of 0 to 10) or a CH3(CH2)m group (wherein m is an integer of 0 to 10), and at least one of Rf1 and Rf2 represents a CF3(CF2)n group, the method comprising: decarboxylating a compound represented by general formula (1) wherein Rf1 and Rf2 are the same as above; and R1 represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, an alkali metal, or M1/2 (wherein M represents an alkaline earth metal), in the presence of at least one member selected from the group consisting of pyridines, amines, quaternary ammonium salts, and quaternary phosphonium salts.
    Type: Application
    Filed: May 23, 2008
    Publication date: July 1, 2010
    Inventors: Akinari Sugiyama, Atsushi Suzuki, Masahiro Tomita
  • Patent number: 7635744
    Abstract: Reactive monomers containing the trifluorovinyloxy group may be copolymerized to form polymers useful as membranes, especially polymer electrolyte membranes for fuel cells. The monomers have the formula ((CF2CFO(R1)p)nArX2 wherein Ar is a trivalent, tetravalent or pentavalent, substituted or unsubstituted, aromatic or heteroaromatic, monocyclic or polycyclic group having from 5 to 50 carbon atoms; X is OH, SH, NR2aR2b, F or Br; p is 0 or 1; n is 1, 2 or 3; R1 is substituted or unsubstituted phenyl and R2a and R2b are independently H, C1-C8 alkyl or C1-C8 perfluoroalkyl.
    Type: Grant
    Filed: April 5, 2006
    Date of Patent: December 22, 2009
    Assignee: General Electric Company
    Inventors: David Roger Moore, Hongyi Zhou, Christoph Georg Erben, Marianne Elisabeth Harmon, Joyce Hung, Hongwei Liu, Daniel Steiger, Daniel Joseph Brunelle
  • Publication number: 20090287010
    Abstract: An oligomer of the formula (I): CnF2n+1(CH2)x[(CF2CF2)y(CH2CH2)z]mG??(I) wherein G is an I; OH; OC(O)CH?CH2; OC(O)CCH3?CH2; OC(O)CCl?CH2; NR1H; N3; NCO; SQ wherein Q is H, alkyl, (CH2)nOH, (CH2)nNH2, (CH2)nOC(O)C(Me)?CH2, or (CH2)nNHC(O)C(Me)?CH2; SCN; COOH; SO3H; NHCOCH?CH2; NHCOC(CH3)?CH2); OC(O)NHCH2CH2OC(O)C(CH3)?CH2; or OC(O)NHCH2CH2OC(O)C(CH3)?CH2; subscript n is an integer from 1 to about 6, subscript x is an integer from 1 to about 6, subscripts y, z and m are each independently 1, 2 or 3, or a mixture thereof, the total number of carbons in said formula (I) excluding G ranges from about 8 to about 22, and a process for preparation thereof.
    Type: Application
    Filed: May 14, 2008
    Publication date: November 19, 2009
    Applicant: E.I. du Pont de Nemours and Company
    Inventors: Weiming Qiu, Anilkumar Raghavanpillai, Michael Francis Vincent
  • Patent number: 7615669
    Abstract: The present invention provides a process for producing highly pure fluoro-compounds by making use of N-(2-chloro-1,1,2-trifluoroethyl)diethylamine. The process produces little or no chlorinated by-products.
    Type: Grant
    Filed: March 22, 2006
    Date of Patent: November 10, 2009
    Assignee: Tosoh F-Tech, Inc.
    Inventors: Norihisa Kondo, Akio Watanabe, Hiroki Kanezaki, Kosuke Kawada
  • Patent number: 7598425
    Abstract: The present invention relates to a method for producing a compound represented by formula (2): [CF3(CF2)n][CF3(CF2)m]C(OH)2??(2) wherein n and m independently represent 0 to 10, the method comprising reacting with a halogen or a halogen-containing oxidizing agent a salt of a compound represented by formula (1): [CF3(CF2)n][CF3(CF2)m]C(OH)COOH??(1) wherein n and m independently represent 0 to 10.
    Type: Grant
    Filed: April 8, 2005
    Date of Patent: October 6, 2009
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshihiro Yamamoto, Yoshichika Kuroki, Daisuke Karube, Tatsuya Ohtsuka
  • Publication number: 20090221859
    Abstract: Difluoroethanol is produced by hydrogenation, in the presence of an effective amount of a catalyst containing at least one element of Group VIII of the Periodic Table deposited onto a solid, acidic mineral support, of an acetyl halide having the following formula (I), in which formula X is a halogen atom other than a fluorine atom:
    Type: Application
    Filed: December 19, 2006
    Publication date: September 3, 2009
    Applicant: RHODIA SERVICES
    Inventors: Olivier Buisine, Roland Jacquot
  • Publication number: 20090221791
    Abstract: The present invention provides a composition and a method for cleaving a peptide from a solid support resin. Hydrochloric acid in an organic water miscible solvent is used to cleave the peptide-resin attachment. Optionally, trifluoroethanol or hexafluoroisopropanol may be added to the cleavage composition to improve results. When using the present cleavage composition, an evaporation or other step to remove carboxylic byproducts is not necessary following the cleavage reaction. After the resin is filtered out of the cleavage mixture, the peptide may be immediately precipitated with water.
    Type: Application
    Filed: April 18, 2007
    Publication date: September 3, 2009
    Applicant: Mallinckrodt Inc.
    Inventor: Kripa Shanker Srivastava
  • Patent number: 7572940
    Abstract: In a first sulfation step, 2-perfluoroalkylethyl iodide is brought into contact with fuming sulfuric acid to obtain a reaction mixture comprising 2-perfluoroalkylethyl sulfate and bis(2-perfluoroalkylethyl)sulfate. Then, in a first hydrolysis step, 2-perfluoroalkylethyl sulfate produced in the first sulfation step is hydrolyzed to obtain a reaction mixture comprising 2-perfluoroalkylethyl alcohol. In a second sulfation step, bis(2-perfluoroalkylethyl)sulfate produced in the first sulfation step is brought into contact with fuming sulfuric acid to obtain a reaction mixture comprising 2-perfluoroalkylethyl sulfate. Then, in a second hydrolysis step, 2-perfluoroalkylethyl sulfate produced in the second sulfation step is hydrolyzed to obtain a reaction mixture comprising 2-perfluoroalkylethyl alcohol. According to such procedures, 2-perfluoroalkylethyl alcohol can be obtained in a high yield.
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: August 11, 2009
    Assignee: Daikin Industries, Ltd.
    Inventors: Yuuki Matsuda, Takeomi Hirasaka, Takuya Ichida
  • Publication number: 20090198086
    Abstract: Provided are a fluorous-tag-introduced fluoroamine of a general formula (I), its production method, a method of fluorination of a substrate having functional group containing oxygen with the fluoroamine serving as a fluorinating agent, and a method of recovering a fluorous-tag-introduced amide after the fluorination. The fluoroamine and its production method, as well as the fluorination method with the fluoroamine and the method of recovery of a fluorous-tag-introduced amide are ecological and advantageous in industrial use, as the load for separating and collecting the product after the fluorination with the fluoroamine serving as a fluorinating agent is small. (In the formula, R0 is an alkyl group or an aryl group having substituent(s) of Rf—(CH2)m—; Rf is a perfluoroalkyl group; m is from 0 to 2; R1 and R2 each are an alkyl group or an aryl group.
    Type: Application
    Filed: May 31, 2007
    Publication date: August 6, 2009
    Inventors: Toshio Hidaka, Takafumi Yoshimura, Shoji Hara, Tsuyoshi Fukuhara
  • Patent number: 7566801
    Abstract: A polyfluoroalkyl alcohol, or a (meth)acrylic acid derivative thereof, represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOR (R:H or (meth)acrylic acid group; n: 1-6; a: 1-4; b: 1-3; and c: 1-3). Polyfluoroalkyl alcohol (R: hydrogen atom) can be produced by reaction of fluoroalkyl iodide represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cI with N-methyl formamide, followed by hydrolysis in the presence of an acid catalyst, whereas polyfluoroalkyl alcohol (meth)acrylic acid derivative (R: (meth)acrylic acid group) can be produced by reaction of the polyfluoroalkyl alcohol with (meth)acrylic acid.
    Type: Grant
    Filed: March 9, 2007
    Date of Patent: July 28, 2009
    Assignee: Unimatec Co., Ltd
    Inventors: Seiichiro Murata, Masayosi Horiuti, Katsuyuki Sato, Hideki Abe, Haruyoshi Tatsu
  • Publication number: 20090177017
    Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.
    Type: Application
    Filed: March 12, 2009
    Publication date: July 9, 2009
    Applicant: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Publication number: 20090143621
    Abstract: A method of forming an alkoxylated fluoroalcohol is accomplished by providing a boron compound having or providing at least one boron-oxygen bond and an iodine source. The boron compound and iodine source are combined with reactants of a fluoroalcohol and an alkylene oxide in the presence of a base. The reactants are allowed to react to form an alkoxylated fluoroalcohol reaction product.
    Type: Application
    Filed: December 1, 2008
    Publication date: June 4, 2009
    Inventor: Thomas Joseph Martin
  • Publication number: 20090137773
    Abstract: Compositions and methods for making compositions such as RF(R?)nQ are provided. The RF group can include at least two —CF3 groups, the R? group can be a group having at least two carbons, n can be at least 1, and the Q group can include one or more atoms of the periodic table of elements. RF-intermediates (RF(RT)nQg); Surfactants (RF(RT)nQs); Foam stabilizers (RF(RT)IIQFS); Metal complexes (RF(RT)IIQMC); Phosphate ester (RF(RT)HQPE); Polymers (RF(RT)IIQMU); Monomers (RF(RT)IIQM); Urethanes (RF(R?)nQu); and/or Glycols (RF(RT)IIQH) and methods for making the same are provided.
    Type: Application
    Filed: July 28, 2006
    Publication date: May 28, 2009
    Inventors: Andrew Jackson, Vimal Sharma, Bradley E. Edwards, Janet Boggs, Victoria Hedrick, Stephan Brandstadter, John Chien, Edward Norman, Robert Kaufman, Bruno Ameduri, George K. Kostov
  • Patent number: 7524995
    Abstract: A continuous process for producing hexafluoroisopropanol is provided which comprises contacting hexafluoroacetone with hexafluoroisopropanol and hydrogen to produce a liquid feed stream; introducing the liquid feed stream to a reactor containing an immobilized hydrogenation catalyst to convert the hexafluoroacetone to hexafluoroisopropanol and provide a product stream; and recovering at least a portion of the hexafluoroisopropanol from the product stream. Preferably a portion of the product stream is recycled. The reactor can be a packed bed or stirred tank reactor.
    Type: Grant
    Filed: June 12, 2008
    Date of Patent: April 28, 2009
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Stephen M. Tieri, John Joseph Hagedom, James Arnold Schultz, Tiberiu M. Leib, Susanne Hawthorne Wolff, Sourav K. Sengupta, Gregory Paul Shankwitz
  • Patent number: 7521582
    Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.
    Type: Grant
    Filed: August 24, 2007
    Date of Patent: April 21, 2009
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Publication number: 20090042996
    Abstract: A surfactant of formula 1 (Rf-A)a-Q-([B]k—R)b??Formula 1 wherein a and b are each independently 1 or 2; Rf is a linear or branched perfluoroalkyl radical having from 2 to about 20 carbon atoms, optionally interrupted with at least one oxygen; R is a C1 to C20 linear, branched or cyclic alkyl, or a C6 to C10 aryl; B is —(CH2CHR1O)x—, k is 0 or 1, x is 1 to about 20, A is —(CH2)m[(CHR1CH2O)]s—[(CH2)m(CH)tCHOH(CH2)m]e—, wherein each m is independently 0 to 3, s is 0 to about 30, t is 0 or 1, and e is 0 or 1, R1 is H or CH3, Q is: —OP(O)(O?M+)(O)—, —O—, —S—(CH2)m—C(O)—O—, —SO2—O— —CH2CH2O—C(O)CH2C(OH)(V)CH2C(O)O—; —(CH2CH2O)xCH2CH(OH)—(CH2CH2O)x—(CH2)m—Si[OSi(R2)3]2—, —SO2NR2—, —(CH2CH2O)zC(O)CH(SO3?M+)CH2C(O)(OCH2CH2)z— wherein z is 1 to about 15, or a bond when s is a positive integer, V is —C(O)OR3 and R3 is H, CH3 or Rf; R2 is C1 to C4 alkyl, and M+ is a Group 1 metal or an ammonium (NHxR2y)+ cation wherein x+y=4, and R2 is C1 to C4 alkyl, provided that when Q is —OP(O)(O?M+)(O)— or when Q is —(
    Type: Application
    Filed: August 6, 2007
    Publication date: February 12, 2009
    Inventors: Charles Kenneth Taylor, Michael Joseph Michalczyk, Erick Jose Acosta
  • Publication number: 20090036706
    Abstract: A polyfluoroalkyl alcohol, or a (meth)acrylic acid derivative thereof, represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOR (R:H or (meth)acrylic acid group; n: 1-6; a: 1-4; b: 1-3; and c: 1-3). Polyfluoroalkyl alcohol (R: hydrogen atom) can be produced by reaction of fluoroalkyl iodide represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cI with N-methyl formamide, followed by hydrolysis in the presence of an acid catalyst, whereas polyfluoroalkyl alcohol (meth)acrylic acid derivative (R: (meth)acrylic acid group) can be produced by reaction of the polyfluoroalkyl alcohol with (meth)acrylic acid.
    Type: Application
    Filed: March 9, 2007
    Publication date: February 5, 2009
    Applicant: UNIMATEC CO., LTD.
    Inventors: Seiichiro Murata, Masayosi Horiuti, Katsuyuki Sato, Hideki Abe, Haruyoshi Tatsu
  • Patent number: 7462734
    Abstract: The present invention relates to a process for producing an optically active ?-fluorocarboxylate derivative represented by the formula [2], by reacting an optically active ?-hydroxycarboxylate derivative with trifluoromethanesulfonyl fluoride (CF3SO2F) in the presence of an organic base, in the formula [2], R represents a straight-chain or branched-chain alkyl group of a carbon number of 1 to 12; one of or two by any combination of aromatic hydrocarbon groups, unsaturated hydrocarbon groups, straight-chain or branched alkoxy groups of a carbon number of 1 to 6, aryloxy groups, halogen atoms (fluorine, chlorine, bromine and iodine), protected carboxyl groups, protected amino groups or protected hydroxyl group can be substituted on any carbon atoms of the alkyl group; R1 represents a straight-chain or branched-chain alkyl group of a carbon number of 1 to 8; any carbon atoms of the alkyl groups of R and R1 may form a covalent bond; and * represents an asymmetric carbon.
    Type: Grant
    Filed: August 5, 2005
    Date of Patent: December 9, 2008
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Hideyuki Tsuruta, Takashi Ootsuka, Yokusu Kuriyama, Manabu Yasumoto, Kenjin Inomiya, Koji Ueda