Fluorine Is The Halogen (i.e., Carboxylic Fluorides) Patents (Class 562/849)
  • Patent number: 10010632
    Abstract: It is intended to provide a novel amino acid organic compound which can be used as a labeling precursor compound for radioactive halogen-labeled amino acid compounds including [18F]FACBC, and which prevents methanol from remaining in the radioactive halogen-labeled amino acid compounds produced therefrom. The novel amino acid organic compound is a compound represented by the following formula: wherein n is an integer of 0 or of 1 to 4; R1 is an ethyl, 1-propyl or isopropyl substituent; X is a halogen substituent or a group represented by —OR2; R2 is a straight-chain or branched-chain haloalkylsulfonic acid substituent with one to 10 carbon atoms, trialkylstannyl substituent with 3 to 12 carbon atoms, fluorosulfonic acid substituent or aromatic sulfonic acid substituent; and R3 is a protective group.
    Type: Grant
    Filed: October 1, 2015
    Date of Patent: July 3, 2018
    Assignee: NIHON MEDI-PHYSICS CO., LTD.
    Inventors: Osamu Ito, Akio Hayashi, Fumie Kurosaki, Masahito Toyama, Toshiyuki Shinmura, Arinori Harano
  • Patent number: 9732212
    Abstract: A composition comprising a mixture of fluoropolyether acids or salts having a number average value of about 800 to about 2500 g/mol. The amount of fluoropolyether acids or salt in the mixture having a molecular weight of not more than 500 g/mol is not more than 50 ppm by weight of the total amount of fluoropolyether acids or salts in the mixture. The amount of fluoropolyether acids or salts in the mixture having a molecular weight of 2500 g/mol or greater is not more than 40% by weight of the total amount of fluoropolyether acids or salts in the mixture. Preferably the fluoropolyether acids or salts comprise an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion and phosphonate. Also disclosed is an aqueous dispersion polymerization process for fluoropolymer manufacture employing polymerization agent comprising the specified mixture of fluoropolyether acids or salts.
    Type: Grant
    Filed: February 20, 2015
    Date of Patent: August 15, 2017
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Gregory Allen Chapman, Jon Lee Howell, Adam Paul Smith
  • Patent number: 9387266
    Abstract: It is intended to provide a novel amino acid organic compound which can be used as a labeling precursor compound for radioactive halogen-labeled amino acid compounds including [18F]FACBC, and which prevents methanol from remaining in the radioactive halogen-labeled amino acid compounds produced therefrom. The novel amino acid organic compound is a compound represented by the following formula: wherein n is an integer of 0 or of 1 to 4; R1 is an ethyl, 1-propyl or isopropyl substituent; X is a halogen substituent or a group represented by —OR2; R2 is a straight-chain or branched-chain haloalkylsulfonic acid substituent with one to 10 carbon atoms, trialkylstannyl substituent with 3 to 12 carbon atoms, fluorosulfonic acid substituent or aromatic sulfonic acid substituent; and R3 is a protective group.
    Type: Grant
    Filed: August 21, 2015
    Date of Patent: July 12, 2016
    Assignee: NIHON MEDI-PHYSICS CO., LTD.
    Inventors: Osamu Ito, Akio Hayashi, Fumie Kurosaki, Masahito Toyama, Toshiyuki Shinmura, Arinori Harano
  • Patent number: 9381259
    Abstract: It is intended to provide a novel amino acid organic compound which can be used as a labeling precursor compound for radioactive halogen-labeled amino acid compounds including [18F]FACBC, and which prevents methanol from remaining in the radioactive halogen-labeled amino acid compounds produced therefrom. The novel amino acid organic compound is a compound represented by the following formula: wherein n is an integer of 0 or of 1 to 4; R1 is an ethyl, 1-propyl or isopropyl substituent; X is a halogen substituent or a group represented by —OR2; R2 is a straight-chain or branched-chain haloalkylsulfonic acid substituent with one to 10 carbon atoms, trialkylstannyl substituent with 3 to 12 carbon atoms, fluorosulfonic acid substituent or aromatic sulfonic acid substituent; and R3 is a protective group.
    Type: Grant
    Filed: April 7, 2014
    Date of Patent: July 5, 2016
    Assignee: NIHON MEDI-PHYSICS CO., LTD.
    Inventors: Osamu Ito, Akio Hayashi, Fumie Kurosaki, Masahito Toyama, Toshiyuki Shinmura, Arinori Harano
  • Publication number: 20140312276
    Abstract: This invention relates to liquid crystal compound of formula I containing a difluoromethyleneoxy linking group that hydrogen substituted by deuterium and therefore being very suitable for formulating a liquid crystal mixture. A liquid crystal mixture containing such type of liquid crystal compounds can be applied in various display devices.
    Type: Application
    Filed: July 3, 2014
    Publication date: October 23, 2014
    Inventors: Wen Hai LU, Ze Feng HOU, Xing ZHANG, Guo Liang YUN, Rui Mao HUA, Jin WANG, Ya Jie DUAN
  • Patent number: 8785689
    Abstract: A method for purifying difluoroacetic acid chloride, including the step of bringing a difluoroacetic acid chloride composition that contains at least difluoroacetic acid fluoride into contact with calcium chloride at a temperature enabling reaction thereof thereby converting difluoroacetic acid fluoride into difluoroacetic acid chloride.
    Type: Grant
    Filed: March 28, 2012
    Date of Patent: July 22, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Naoto Takada, Masamune Okamoto, Hideaki Imura
  • Patent number: 8716526
    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: Grant
    Filed: March 16, 2011
    Date of Patent: May 6, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Masamune Okamoto, Hideaki Imura, Naoto Takada
  • Patent number: 8513459
    Abstract: Perfluoropolyether carboxylic acid fluoride having the following general formula: F(CF2CF2CF2O)nCF2CF2COF (n: 2-200, preferably 35-70) can be produced by starting fluorination reaction of polyfluoropolyether carboxylic acid having the general formula as a tetrafluorooxetane polymer: F(CH2CF2CF2O)nCH2CF2COF (n: 2-200) in a dispersed state in a perfluoropolyether-based solvent with a fluorine gas at 50°-80° C., then slowly elevating the fluorination reaction temperature, and finally completing the fluorination reaction at 100°-120° C., where even in the case of fluorination reaction of the starting material with a high degree of polymerization the desired product can be produced in high yield, while suppressing the decomposition and keeping the high degree of polymerization substantially.
    Type: Grant
    Filed: February 1, 2007
    Date of Patent: August 20, 2013
    Assignee: Unimatec Co., Ltd.
    Inventor: Sunao Ikeda
  • Patent number: 8394989
    Abstract: Provided are fluorinated oxy-carboxylic acids, derivatives of oxy-carboxylic acids, and methods of preparing oxy-carboxylic acids and derivatives thereof.
    Type: Grant
    Filed: September 26, 2008
    Date of Patent: March 12, 2013
    Assignee: 3M Innovative Properties Company
    Inventors: Werner Schwertfeger, Klaus Hintzer, Egon Obermaier
  • Patent number: 8338502
    Abstract: To provide a polymerizable fluorine-containing compound useful for producing a treated substrate having a hydrophilic region and a water repellent region, of which the contrast is high on its surface, without requiring a special apparatus, high energy light, or irradiation with light for a long time. A polymerizable fluorine-containing compound, which is a derivative of a polyhydric alcohol and comprises at least one following structure (A) and at least one following structure (B) in its molecule: structure (A): a structure wherein a compound having a fluoroalkyl group and a carboxyl group is bonded to one hydroxyl group of a polyhydric alcohol by an ester linkage, structure (B): a structure wherein a compound having an ethylenic double bond and a carboxyl group is bonded to one hydroxyl group of a polyhydric alcohol by an ester linkage or a structure wherein a compound having an ethylenic double bond and an isocyanate group is bonded to one hydroxyl group of a polyhydric alcohol by a urethane bond.
    Type: Grant
    Filed: February 5, 2009
    Date of Patent: December 25, 2012
    Assignee: Asahi Glass Company, Limited
    Inventors: Taiki Hoshino, Yutaka Furukawa
  • Publication number: 20120234351
    Abstract: Disclosed is a cleaning gas for deposits, which contains CHF2COF. The cleaning gas may contain O2, O3, CO, CO2, F2, NF3, Cl2, Br2, I2, XFn (In this formula, X represents Cl, I or Br. n represents an integer satisfying 1?n?7.), CH4, CH3F, CH2F2, CHF3, N2, He, Ar, Ne, Kr and the like, and can be applied to deposits that include at least one selected from the group consisting of W, Ti, Mo, Re, Ge, P, Si, V, Nb, Ta, Se, Te, Os, Ir, Sb, Au, Ag, As, Cr, Hf, Zr, Ni, Co, their compounds, and the like. This cleaning gas is not only excellent in cleaning performances but also easily available and does not substantially by-produce CF4 that places a burden on the environment.
    Type: Application
    Filed: November 19, 2010
    Publication date: September 20, 2012
    Applicant: Central Glass Company ,Limited
    Inventors: Naoto Takada, Isamu Mori
  • Publication number: 20120065347
    Abstract: The present invention provides novel polymers obtained by polymerizing a compound of formula (1) which has a highly fluorinated norbornane structure.
    Type: Application
    Filed: November 22, 2011
    Publication date: March 15, 2012
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventors: Yasuhisa MATSUKAWA, Daisuke SHIRAKAWA, Eisuke MUROTANI, Naoko SHIROTA, Yoko TAKEBE
  • Patent number: 8067585
    Abstract: The present invention relates to producing a disulfonyl fluoride compound easily and efficiently by utilizing coupling reaction where a compound (2) is obtained by subjecting a compound (1) wherein Y is a fluorine atom to photocoupling reaction, or subjecting a compound (1) wherein Y is a hydroxyl group, —OMa wherein Ma is an alkali metal atom, or —O(Mb)1/2 wherein Mb is an alkaline earth metal atom to electrolytic coupling reaction, and derivatives such as the following compound (7A) are obtained from the compound (2): FSO2-E-CX2—COY??(1) FSO2-E-CX2—CX2-E-SO2F??(2) wherein E is a single bond, —O—, a C1-20 alkylene group which may contain an etheric oxygen atom, or the like, X is a fluorine atom or the like, and Y is a fluorine atom, a hydroxyl group, or the like.
    Type: Grant
    Filed: October 1, 2007
    Date of Patent: November 29, 2011
    Assignee: Asahi Glass Company, Limited
    Inventors: Masao Iwaya, Kazuya Oharu, Hidekazu Okamoto
  • Publication number: 20110251427
    Abstract: A polyfluoroalkane carboxylic acid represented by the following general formula: CnF2n+1(CH2CF2)m(CF2CF2)l?1CF2COOM (M: an alkali metal, a NH4 group or H; n: an integer of 1 to 6; m: an integer of 1 to 4; and l: 1 or 2) can be produced by hydrolysis reaction of polyfluoroalkane carboxylic acid fluoride represented by the following general formula: CnF2n+1(CH2CF2)m(CF2CF2)l?1CF2COF , where its carboxylic acid salt can be formed as an alkali metal salt, or a NH4 salt. The polyfluoroalkane carboxylic acid (or its salt) can act as a surfactant having distinguished monomer emulsificability and latex stability when used as an emulsifying agent or as a dispersing agent for polymerization reaction of fluorine-containing monomers, or as an effective surfactant capable of enhancing the micelles solubility of fluorine-containing monomers such as vinylidene fluoride, etc., when used as an emulsifying agent or a dispersing agent for homopolymerization or copolymerization reaction of vinylidene fluoride.
    Type: Application
    Filed: July 17, 2007
    Publication date: October 13, 2011
    Applicant: Nippon Mektron, Limited
    Inventors: Daisuke Murai, Takashi Enokida, Seiichiro Murata
  • Publication number: 20110177693
    Abstract: Gas mixtures which comprise acids like HF, HCl or HBr and other constituents, especially gas mixtures which comprise or consist of carboxylic acid fluorides, C(O)F2 or phosphorous pentafluoride and HCl and optionally HF, can be separated by ionic liquids. The process is performed reversibly. Ionic liquids are applied the anion of which corresponds to a stronger acid than the acid to be removed. Highly purified products, for example, highly purified carbonyl fluoride can be obtained.
    Type: Application
    Filed: April 1, 2011
    Publication date: July 21, 2011
    Applicant: SOLVAY FLUOR GMBH
    Inventors: Jens Olschimke, Carsten Brosch, Andreas Grossmann
  • Publication number: 20100121106
    Abstract: A process for preparing perfluoropolyethers of formula T-O—(RF)z-T???(I) wherein: T, T? are end groups, z=0 or 1; RF is a perfluoro(poly)oxyalkylene chain containing one or more fluorooxyalkylene repeating units selected from the group consisting of (CF2O), —(CF(CF3)O)—, —(CF2CF2O)—, —(CF2CF(CF3)O)—, —(CF(CF3)CF2O)—, —(CF2CF2CF2O)—, —(CF2CF2CF2CF2O)—, and —(CF2)j—CFZ—O— wherein j is an integer from 0 to 3, and Z is a fluorooxyalkylene chain comprising from 1 to 20 repeating units selected from the above reported fluorooxyalkylene units; comprising the reduction of peroxidic perfluoropolyethers comprising one or more of the above defined repeating units by using gaseous hydrogen in the presence of a catalyst comprising one or more metals of the VIII group supported on graphitic materials.
    Type: Application
    Filed: April 8, 2008
    Publication date: May 13, 2010
    Applicant: SOLVAY SOLEXIS S.P.A.
    Inventors: Ugo De Patto, Giuseppe Marchionni, Pier Antonio Guarda
  • Patent number: 7501540
    Abstract: The present invention provides a process for producing compounds useful as raw materials for various fluororesins in high yields in few steps from inexpensive and readily available starting materials. The following compound (1) and the following compound (2) are reacted to form the following compound (3), then the compound (3) is fluorinated in a liquid phase to form the following compound (4), and the ester bonds in the compound (4) are dissociated to form the compound (5), or the compound (5) and the compound (6). HOCH2-Q-O—(CH2)3—OH??(1), CRBCOX??(2), RBCOOCH2-Q-O—(CH2)3—OCORB??(3), RBFCOOCF2-QF-O—(CF2)3—OCORBF??(4), FCO-QF-O—(CF2)2—COF??(5), RBFCOF??(6).
    Type: Grant
    Filed: June 29, 2007
    Date of Patent: March 10, 2009
    Assignee: Asahi Glass Company, Limited
    Inventors: Shu-zhong Wang, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Daisuke Shirakawa, Kazuya Oharu
  • Publication number: 20090054687
    Abstract: Perfluoropolyether carboxylic acid fluoride having the following general formula: F(CF2CF2CF2O)nCF2CF2COF (n: 2-200, preferably 35-70) can be produced by starting fluorination reaction of polyfluoropolyether carboxylic acid having the general formula as a tetrafluorooxetane polymer: F(CH2CF2CF2O)nCH3CF2COF (n: 2-200) in a dispersed state in a perfluoropolyether-based solvent with a fluorine gas at 50° -80° C. , then slowly elevating the fluorination reaction temperature, and finally completing the fluorination reaction at 100°-120° C., where even in the case of fluorination reaction of the starting material with a high degree of polymerization the desired product can be produced in high yield, while suppressing the decomposition and keeping the high degree of polymerization substantially.
    Type: Application
    Filed: February 1, 2007
    Publication date: February 26, 2009
    Applicant: UNI-CHARM CORPORATION
    Inventor: Sunao Ikeda
  • Patent number: 7425646
    Abstract: A compound represented by the formula AF(—COF)n, provided that AF and n have the following meanings. AF: a fluorinated adamantane residue which is an n-valent group having an n number of hydrogen atoms removed from adamantane (provided that when n is at least 2, the removed hydrogen atoms are hydrogen atoms bonded to different carbon atoms), wherein at least one of the remaining hydrogen atoms is substituted by a fluorine atom, and the remaining hydrogen atoms may be substituted by a C1-6 alkyl group or fluoroalkyl group, and n: an integer of from 1 to 4, provided the when n is 1, AF has at least one hydrogen atom.
    Type: Grant
    Filed: December 15, 2006
    Date of Patent: September 16, 2008
    Assignee: Asahi Glass Company, Limited
    Inventors: Kazuya Oharu, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Masahiro Ito
  • Patent number: 7423174
    Abstract: The present invention provides a process for selectively separating HF and like acids present along with water-unstable organic acid fluorides. In particular, the invention provides a process for separating an acid from a system in which the acid and an organic acid fluoride are present, the organic acid fluoride being represented by formula (I): RCOF??(I) wherein R is a fluorine atom; a C1-20 linear, branched or cyclic alkyl or halogenated alkyl group that may contain a heteroatom; or a C6-20 aryl or halogenated aryl group that may contain a heteroatom; the process comprising using as a deacidifying agent an aromatic heterocyclic compound having a boiling point of at least 50° C. and having one or more nitrogen atoms as heteroatom.
    Type: Grant
    Filed: May 30, 2002
    Date of Patent: September 9, 2008
    Assignee: Daikin Industries, Ltd.
    Inventors: Masaki Irie, Masahiro Kondou
  • Patent number: 7393961
    Abstract: (Per)haloethers having formula: X-(Rf)L-O—CF2CF2—O—CX1X2—CFX3X4 , ??(I) process for obtaining them and hypofluorites usable in the synthesis of said (per)haloethers.
    Type: Grant
    Filed: March 8, 2005
    Date of Patent: July 1, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 7381420
    Abstract: This invention concerns novel labeling reactants suitable for labeling of a biospecific binding reactant using solid-phase synthesis. The novel reactants are derivatives of diethylenetriaminepentaacetic acid (DTPA), wherein a suitable group is linked to the DTPA molecule, thus allowing site specific introduction of the ligand of the derivatives to bioactive molecules on solid phase in an oligopeptide synthesizer.
    Type: Grant
    Filed: December 1, 2006
    Date of Patent: June 3, 2008
    Assignee: Wallac Oy
    Inventors: Jari Hovinen, Jari Peuralahti, Veli-Matti Mukkala
  • Patent number: 7375253
    Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I): F-A-RF—B—C(O)X1??(I) wherein: X1=F, CF3; A, B equal to or different from each other, are independently (per)fluoroalkylene or (per)fluorooxyalkylene groups; RF is —ORf1O— wherein Rf1=perfluoroalkylene or —ORf2, wherein Rf2 is a perfluorooxyalkylene chain; said process comprising the following steps: A) obtainment of the formula (II) mono-hypofluorite: FO—CFX2-A-RF—B—C(O)X1??(II) by partial fluorination with elemental fluorine of the carbonyl groups of the formula (III) compound: X2(O)C-A-RF—B—C(O)X1??(III) in the presence of a formula MeFy catalyst, Me being an alkaline or alkaline-earth metal or Ag, y=1 or 2; B) thermal decomposition of the compound (II) to give the compounds according to the following scheme: FO—CFX2-A-RF—B—C(O)X1 (II) - - - ?F-A-RF—B—C(O)X1 (I)+(O)CFX2.
    Type: Grant
    Filed: January 9, 2004
    Date of Patent: May 20, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 7371899
    Abstract: To provide a method for producing carbonyl fluoride by employing carbon monoxide and fluorine as starting materials, without such a problem as vigorous heat generation or a decrease in the reaction yield due to a side reaction.
    Type: Grant
    Filed: June 15, 2007
    Date of Patent: May 13, 2008
    Assignee: Asahi Glass Company, Limited
    Inventors: Yuuki Mitsui, Koichi Yanase
  • Patent number: 7321062
    Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula: F—A—(RF)t—B—C(O)X1??(I) wherein: X1=F, CF3; t=0, 1; A, B equal to or different from each other, are independently C1-C5 (per)fluoroalkylene groups or C1-C5 (per)fluorooxy-alkylene groups; RF is —Rf1—, C1-C20 perfluoroalkylene, —ORf1O—; or —ORf2—, wherein Rf2 is a perfluorooxyalkylene chain; wherein the carbonyl groups of a (per)fluorinated di-functional carbonyl compound of formula (III): X2(O)C—A—(RF)t—B—C(O)X1??(III) wherein: X1, RF, t, A and B have the above meanings; X2, equal to or different from X1, has the same meanings as X1; are partially fluorinated with elemental fluorine in the presence of a catalyst having formula MeFy.zHF, Me being an alkaline or alkaline-earth metal or Ag, y=1 or 2, z an integer from 0 to 4, carrying out said reaction at a temperature higher than a temperature such that it leads to the formation of C(O)FX2.
    Type: Grant
    Filed: January 9, 2004
    Date of Patent: January 22, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 7253315
    Abstract: A fluorocarboxylic acid preparation process which includes hydrolyzing fluorocarboxylic acid fluoride in the presence of an aqueous sulfuric acid solution to form a reaction product containing a fluorocarboxylic acid and hydrogen fluoride (present as hydrofluoric acid); and removing at least some of the hydrogen fluoride from the reaction product by washing the reaction production with aqueous sulfuric acid solution. The hydrolyzing and washing are carried out at a temperature at which the fluorocarboxylic acid is a liquid.
    Type: Grant
    Filed: March 24, 2005
    Date of Patent: August 7, 2007
    Assignees: Daikin Industries, Ltd., E. I. du Pont de Nemours and Company
    Inventors: Ta-Wei Fu, Steven H. Swearingen, Takuya Ichida, Shigeyuki Yoshii
  • Patent number: 7208638
    Abstract: A process for preparing (per)fluorohalogenethers having general formula: wherein: A and A?, equal to or different from each other, are selected among Cl, Br and H; m=1, 2; n=0, 1; R? is a C1 to C3 (per)fluoroalkyl substituent; R is a (per)fluoropolyether substituent; z and z? are 1 or zero, X1=F, CF3; by reaction of carbonyl compounds having formula: (R?)n—C(O)(F)q(CFX1(CF2)z(CH2)z?OR1)??(II) wherein: R? and n are as above; q=0, 1; X1=F or CF3; z=0 or 1; R1 is a (per)fluoropolyether substituent; in liquid phase, with elemental fluorine and with olefinic compounds of formula: CAF=CA?F2 ??(III) wherein A and A? are as above, at temperatures from ?120° C. to ?20° C., preferably from ?100° C. to ?40° C.
    Type: Grant
    Filed: January 28, 2005
    Date of Patent: April 24, 2007
    Assignee: Solvay Solexis, S.p.A.
    Inventors: Vito Tortelli, Stefano Millefanti, Pierangelo Calini
  • Patent number: 7141704
    Abstract: Process for obtaining hydrofluoroethers of formula (I): A-(Rf)n0—CF(Rf1)—O—Rh??(I) wherein a mono- or bifunctional carbonyl compound of formula (IV): B—Rf—C(O)Rf1??(IV) is reacted with at least one equivalent of a fluoroformate of formula (III) R—OC(O)F??(III) in the presence of an ion fluoride compound (catalyst) and of a dipolar aprotic organic compound, liquid and inert under the reaction conditions.
    Type: Grant
    Filed: March 26, 2004
    Date of Patent: November 28, 2006
    Assignee: Solvay Solexis S.P.A.
    Inventors: Walter Navarrini, Marco Galimberti, Giovanni Fontana
  • Patent number: 7002040
    Abstract: This invention relates generally to a improvement in a process for the purification of fluoroxy compounds, such as bis(fluoroxy)difluoromethane and fluoroxytrifluoromethane produced by the fluorination of carbon oxides. The improvement in effecting purification of the fluoroxy compounds is effected by initially selectively removing the fluorine by contacting with a crystalline zeolite and then removing the carbon oxide by selective adsorption.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: February 21, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Robert George Syvret, Philip Bruce Henderson, Donald Elson Fowler, Beth Ann Campion
  • Patent number: 6998506
    Abstract: A process for preparing acylfluorides by reaction of carbonyl fluoride COF2 with compounds having general formula: T=CR1R2??(I) wherein: T is O or CF2 R1 and R2, equal or different, are F or a R(O)t radical, wherein R=linear or branched C1–C7 (per)fluoroalkyl, optionally containing one or more oxygen atoms, t is an integer equal to zero or 1; wherein a catalyst supported on porous compound is used, the catalyst being selected from: CsF, RbF, KF, AgF, each optionally in admixture with one or more of the others.
    Type: Grant
    Filed: December 3, 2004
    Date of Patent: February 14, 2006
    Assignee: Solvay Solexis SpA
    Inventors: Marco Galimberti, Walter Navarrini
  • Patent number: 6969776
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: November 29, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6956138
    Abstract: The present invention provides a method for obtaining a compound useful as a raw material for various fluororesins in high yield by a short process by using a starting material which is inexpensive and readily available.
    Type: Grant
    Filed: April 28, 2004
    Date of Patent: October 18, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Masahiro Ito, Daisuke Shirakawa, Masao Iwaya, Hidekazu Okamoto
  • Patent number: 6923921
    Abstract: Described are fluorinated polyether compounds having a molecular weight range between 750 g/mol and 4000 g/mol where such polyether compounds are intermediates used in fluorinated compositions for treating various substrates.
    Type: Grant
    Filed: December 30, 2002
    Date of Patent: August 2, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Daniel R. Vitcak, Richard S. Buckanin, Cheryl L. S. Elsbernd
  • Patent number: 6919479
    Abstract: A process for the preparation of perfluoropolyethers of formula: T-CFX?—O—Rf—CFX—COF??(I) wherein: T=COF, F, C1-C3 perfluoroalkyl; X, X?=—F, —CF3; Rf=—(C2F4O)m(CF2CF(CF3)O)n(CF2O)p(CF(CF3)O)q—, the sum n+m+p+q ranges from 2 to 200, by reduction with hydrogen of the corresponding peroxidic perfluoropolyethers, in the presence of a catalyst formed by metals of the VIII group supported on metal fluorides, at a temperture from 20° C. to 140° C., and at a pressure between 1 and 50 atm.
    Type: Grant
    Filed: August 1, 2003
    Date of Patent: July 19, 2005
    Assignee: Solvay Solexis S.p.A.
    Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
  • 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: 6852884
    Abstract: A process for preparing acylfluorides by reaction of carbonyl fluoride COF2 with compounds having general formula: T=CR1R2??(I) wherein: T is O or CF2 R1 and R2, equal or different, are F or a R(O)t radical, wherein R=linear or branched C1-C7 (per)fluoroalkyl, optionally containing one or more oxygen atoms, t is an integer equal to zero or 1; wherein a catalyst supported on porous compound is used, the catalyst being selected from: CsF, RbF, KF, AgF, each optionally in admixture with one or more of the others.
    Type: Grant
    Filed: June 16, 2003
    Date of Patent: February 8, 2005
    Assignee: Solvay Solexis S.p.A.
    Inventors: Marco Galimberti, Walter Navarrini
  • Patent number: 6833477
    Abstract: The process for producing a vic-dichloro acid fluoride compound in a short process and in good yield from the starting material which is inexpensive and readily available is provided. (RH1—EH1—)CRH2RH3CH2—OCORHB (I) is fluorinated in a liquid phase to form (CF2ClCFCl—EFF1—) CRF2RF3CF2—OCORFB (II), and then, an ester bond of the compound (II) is decomposed to form (CF2ClCFCl—EF1—)CRF2RF3COF(III) or the compound (III) and FCORFB (IV).
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: December 21, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • Patent number: 6803488
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: October 12, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Publication number: 20040158100
    Abstract: The present invention provides a process for selectively separating HF and like acids present along with water-unstable organic acid fluorides.
    Type: Application
    Filed: November 17, 2003
    Publication date: August 12, 2004
    Inventors: Masaki Irie, Masahiro Kondou
  • Publication number: 20040147778
    Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I):
    Type: Application
    Filed: January 9, 2004
    Publication date: July 29, 2004
    Applicant: SOLVAY SOLEXIS S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Publication number: 20040116742
    Abstract: A method is provided for reacting hexafluoropropylene oxide (HFPO) with a perfluoroacyl fluorides according to the formula X—Rf—COF (II) to selectively produce a monoaddition product according to the formula X—Rf—CF2—O—CF(CF3)COF (I), wherein selectivity for the monoaddition product over the biaddition product is 90% or greater or more typically 95% or greater. A continuous or repeated-batch process is provided comprising the steps of: a) providing a mixture of X—Rf—COF (II), a fluoride salt, and a polar solvent; b) adding hexafluoropropylene oxide (HFPO) in an amount such that X—Rf—COF remains in molar excess of HFPO by at least 10% and reacting X—Rf—COF with HFPO; c) separating unreacted X—Rf—COF from a mixture of addition products of hexafluoropropylene oxide (HFPO) and X—Rf—COF; and d) repeating step a) using unreacted X—Rf—COF separated in step c).
    Type: Application
    Filed: December 17, 2002
    Publication date: June 17, 2004
    Applicant: 3M Innovative Properties Company
    Inventor: Miguel Antonio Guerra
  • Publication number: 20040110968
    Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.
    Type: Application
    Filed: December 5, 2003
    Publication date: June 10, 2004
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • 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
  • Publication number: 20040097758
    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: Application
    Filed: August 1, 2003
    Publication date: May 20, 2004
    Applicant: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Carsten Brosch
  • Patent number: 6632949
    Abstract: Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.
    Type: Grant
    Filed: July 10, 2002
    Date of Patent: October 14, 2003
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
  • Publication number: 20030187280
    Abstract: (Per)haloethers having formula:
    Type: Application
    Filed: February 4, 2003
    Publication date: October 2, 2003
    Applicant: Solvay Solexis S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 6586626
    Abstract: The invention provides a process for producing a fluorine-containing compound from an inexpensive material. Namely, Compound I such as RACH2OH is reacted with Compound II such as XCORB to form Compound III such as RACH2OCORB, followed by fluorination in a liquid phase to form Compound IV such as RAFCF2OCORBF, which is converted to Compound V such as RAFCOF and/or Compound VI such as RBFCOF. RA is an alkyl group or the like, RB is a perhalogenoalkyl group or the like, RAF and RBF are fluorinated RA and RB, and X is halogen.
    Type: Grant
    Filed: September 24, 2001
    Date of Patent: July 1, 2003
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
  • Patent number: 6489510
    Abstract: A method for producing carboxylic acid fluorides of the formula RCFXC(O)F, where X represents fluorine or chlorine, in good yields and with good selectivity for the carboxylic acid fluorides by reacting compounds of the formula RCFXCHFCl with oxygen by photochemical oxidation in the gaseous phase, preferably under sensitization with chlorine and using light having a wavelength &lgr;≧280 nm, which conditions make it possible to work without the use of pressure. Glass apparatus may be covered with a protective coating so as to protect it against traces of hydrogen fluoride. To this end, for example, heat-shrinkable sleeves made of light-permeable hydrogen fluoride-resistant material may be used. Polytetrafluoroethylene, polyfluoropropylene or a mixture thereof are especially suitable for this purpose.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: December 3, 2002
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Kerstin Eichholz, Werner Rudolph
  • Publication number: 20020169276
    Abstract: A synthetic process of perfluoropolyether iodides, by reaction with LiI of monoacyl- or diacyl-halides of perfluoropolyethers, having number average molecular weight from 200 to 3,000, and having the following structure:
    Type: Application
    Filed: May 9, 2002
    Publication date: November 14, 2002
    Applicant: AUSIMONT S.P.A.
    Inventors: Ivan Wlassics, Vito Tortelli
  • Publication number: 20020156321
    Abstract: The invention provides an improved process for preparing bis(fluoroxy)difluoro-methane (BDM) by continuously reacting F2 with CO2 in a reactor containing a fluorination catalyst (e.g., CsF), wherein the process is conducted at a pressure above atmospheric pressure. The process provides BDM of very high purity and very low residual F2.
    Type: Application
    Filed: February 13, 2001
    Publication date: October 24, 2002
    Inventor: Robert George Syvret