Fluorine Is The Halogen (i.e., Carboxylic Fluorides) Patents (Class 562/849)
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Patent number: 10010632Abstract: 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: GrantFiled: October 1, 2015Date of Patent: July 3, 2018Assignee: NIHON MEDI-PHYSICS CO., LTD.Inventors: Osamu Ito, Akio Hayashi, Fumie Kurosaki, Masahito Toyama, Toshiyuki Shinmura, Arinori Harano
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Patent number: 9732212Abstract: 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: GrantFiled: February 20, 2015Date of Patent: August 15, 2017Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Gregory Allen Chapman, Jon Lee Howell, Adam Paul Smith
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Patent number: 9387266Abstract: 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: GrantFiled: August 21, 2015Date of Patent: July 12, 2016Assignee: NIHON MEDI-PHYSICS CO., LTD.Inventors: Osamu Ito, Akio Hayashi, Fumie Kurosaki, Masahito Toyama, Toshiyuki Shinmura, Arinori Harano
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Patent number: 9381259Abstract: 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: GrantFiled: April 7, 2014Date of Patent: July 5, 2016Assignee: NIHON MEDI-PHYSICS CO., LTD.Inventors: Osamu Ito, Akio Hayashi, Fumie Kurosaki, Masahito Toyama, Toshiyuki Shinmura, Arinori Harano
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Publication number: 20140312276Abstract: 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: ApplicationFiled: July 3, 2014Publication date: October 23, 2014Inventors: Wen Hai LU, Ze Feng HOU, Xing ZHANG, Guo Liang YUN, Rui Mao HUA, Jin WANG, Ya Jie DUAN
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Patent number: 8785689Abstract: 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: GrantFiled: March 28, 2012Date of Patent: July 22, 2014Assignee: Central Glass Company, LimitedInventors: Naoto Takada, Masamune Okamoto, Hideaki Imura
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Patent number: 8716526Abstract: 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: GrantFiled: March 16, 2011Date of Patent: May 6, 2014Assignee: Central Glass Company, LimitedInventors: Masamune Okamoto, Hideaki Imura, Naoto Takada
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Patent number: 8513459Abstract: 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: GrantFiled: February 1, 2007Date of Patent: August 20, 2013Assignee: Unimatec Co., Ltd.Inventor: Sunao Ikeda
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Patent number: 8394989Abstract: Provided are fluorinated oxy-carboxylic acids, derivatives of oxy-carboxylic acids, and methods of preparing oxy-carboxylic acids and derivatives thereof.Type: GrantFiled: September 26, 2008Date of Patent: March 12, 2013Assignee: 3M Innovative Properties CompanyInventors: Werner Schwertfeger, Klaus Hintzer, Egon Obermaier
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Patent number: 8338502Abstract: 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: GrantFiled: February 5, 2009Date of Patent: December 25, 2012Assignee: Asahi Glass Company, LimitedInventors: Taiki Hoshino, Yutaka Furukawa
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Publication number: 20120234351Abstract: 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: ApplicationFiled: November 19, 2010Publication date: September 20, 2012Applicant: Central Glass Company ,LimitedInventors: Naoto Takada, Isamu Mori
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Publication number: 20120065347Abstract: The present invention provides novel polymers obtained by polymerizing a compound of formula (1) which has a highly fluorinated norbornane structure.Type: ApplicationFiled: November 22, 2011Publication date: March 15, 2012Applicant: ASAHI GLASS COMPANY LIMITEDInventors: Yasuhisa MATSUKAWA, Daisuke SHIRAKAWA, Eisuke MUROTANI, Naoko SHIROTA, Yoko TAKEBE
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Patent number: 8067585Abstract: 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: GrantFiled: October 1, 2007Date of Patent: November 29, 2011Assignee: Asahi Glass Company, LimitedInventors: Masao Iwaya, Kazuya Oharu, Hidekazu Okamoto
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Publication number: 20110251427Abstract: 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: ApplicationFiled: July 17, 2007Publication date: October 13, 2011Applicant: Nippon Mektron, LimitedInventors: Daisuke Murai, Takashi Enokida, Seiichiro Murata
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Publication number: 20110177693Abstract: 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: ApplicationFiled: April 1, 2011Publication date: July 21, 2011Applicant: SOLVAY FLUOR GMBHInventors: Jens Olschimke, Carsten Brosch, Andreas Grossmann
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Publication number: 20100121106Abstract: 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: ApplicationFiled: April 8, 2008Publication date: May 13, 2010Applicant: SOLVAY SOLEXIS S.P.A.Inventors: Ugo De Patto, Giuseppe Marchionni, Pier Antonio Guarda
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Patent number: 7501540Abstract: 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: GrantFiled: June 29, 2007Date of Patent: March 10, 2009Assignee: Asahi Glass Company, LimitedInventors: Shu-zhong Wang, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Daisuke Shirakawa, Kazuya Oharu
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Publication number: 20090054687Abstract: 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: ApplicationFiled: February 1, 2007Publication date: February 26, 2009Applicant: UNI-CHARM CORPORATIONInventor: Sunao Ikeda
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Patent number: 7425646Abstract: A compound represented by the formula AF(—COF)n, provided that AF and n have the following meanings. AF: a fluorinated adamantane residue which is an n-valent group having an n number of hydrogen atoms removed from adamantane (provided that when n is at least 2, the removed hydrogen atoms are hydrogen atoms bonded to different carbon atoms), wherein at least one of the remaining hydrogen atoms is substituted by a fluorine atom, and the remaining hydrogen atoms may be substituted by a C1-6 alkyl group or fluoroalkyl group, and n: an integer of from 1 to 4, provided the when n is 1, AF has at least one hydrogen atom.Type: GrantFiled: December 15, 2006Date of Patent: September 16, 2008Assignee: Asahi Glass Company, LimitedInventors: Kazuya Oharu, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Masahiro Ito
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Patent number: 7423174Abstract: 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: GrantFiled: May 30, 2002Date of Patent: September 9, 2008Assignee: Daikin Industries, Ltd.Inventors: Masaki Irie, Masahiro Kondou
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Patent number: 7393961Abstract: (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: GrantFiled: March 8, 2005Date of Patent: July 1, 2008Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 7381420Abstract: 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: GrantFiled: December 1, 2006Date of Patent: June 3, 2008Assignee: Wallac OyInventors: Jari Hovinen, Jari Peuralahti, Veli-Matti Mukkala
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Patent number: 7375253Abstract: 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: GrantFiled: January 9, 2004Date of Patent: May 20, 2008Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 7371899Abstract: 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: GrantFiled: June 15, 2007Date of Patent: May 13, 2008Assignee: Asahi Glass Company, LimitedInventors: Yuuki Mitsui, Koichi Yanase
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Patent number: 7321062Abstract: 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: GrantFiled: January 9, 2004Date of Patent: January 22, 2008Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 7253315Abstract: 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: GrantFiled: March 24, 2005Date of Patent: August 7, 2007Assignees: Daikin Industries, Ltd., E. I. du Pont de Nemours and CompanyInventors: Ta-Wei Fu, Steven H. Swearingen, Takuya Ichida, Shigeyuki Yoshii
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Patent number: 7208638Abstract: 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: GrantFiled: January 28, 2005Date of Patent: April 24, 2007Assignee: Solvay Solexis, S.p.A.Inventors: Vito Tortelli, Stefano Millefanti, Pierangelo Calini
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Patent number: 7141704Abstract: 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: GrantFiled: March 26, 2004Date of Patent: November 28, 2006Assignee: Solvay Solexis S.P.A.Inventors: Walter Navarrini, Marco Galimberti, Giovanni Fontana
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Patent number: 7002040Abstract: 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: GrantFiled: January 28, 2003Date of Patent: February 21, 2006Assignee: Air Products and Chemicals, Inc.Inventors: Robert George Syvret, Philip Bruce Henderson, Donald Elson Fowler, Beth Ann Campion
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Patent number: 6998506Abstract: 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: GrantFiled: December 3, 2004Date of Patent: February 14, 2006Assignee: Solvay Solexis SpAInventors: Marco Galimberti, Walter Navarrini
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Patent number: 6969776Abstract: 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: GrantFiled: June 17, 2004Date of Patent: November 29, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
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Patent number: 6956138Abstract: 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: GrantFiled: April 28, 2004Date of Patent: October 18, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Masahiro Ito, Daisuke Shirakawa, Masao Iwaya, Hidekazu Okamoto
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Patent number: 6923921Abstract: 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: GrantFiled: December 30, 2002Date of Patent: August 2, 2005Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Daniel R. Vitcak, Richard S. Buckanin, Cheryl L. S. Elsbernd
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Patent number: 6919479Abstract: 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: GrantFiled: August 1, 2003Date of Patent: July 19, 2005Assignee: Solvay Solexis S.p.A.Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
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Patent number: 6919480Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.Type: GrantFiled: December 5, 2003Date of Patent: July 19, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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Patent number: 6852884Abstract: 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: GrantFiled: June 16, 2003Date of Patent: February 8, 2005Assignee: Solvay Solexis S.p.A.Inventors: Marco Galimberti, Walter Navarrini
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Patent number: 6833477Abstract: 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: GrantFiled: February 28, 2002Date of Patent: December 21, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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Patent number: 6803488Abstract: 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: GrantFiled: February 26, 2003Date of Patent: October 12, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
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Publication number: 20040158100Abstract: The present invention provides a process for selectively separating HF and like acids present along with water-unstable organic acid fluorides.Type: ApplicationFiled: November 17, 2003Publication date: August 12, 2004Inventors: Masaki Irie, Masahiro Kondou
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Publication number: 20040147778Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I):Type: ApplicationFiled: January 9, 2004Publication date: July 29, 2004Applicant: SOLVAY SOLEXIS S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Publication number: 20040116742Abstract: 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: ApplicationFiled: December 17, 2002Publication date: June 17, 2004Applicant: 3M Innovative Properties CompanyInventor: Miguel Antonio Guerra
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Publication number: 20040110968Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.Type: ApplicationFiled: December 5, 2003Publication date: June 10, 2004Applicant: ASAHI GLASS COMPANY LIMITEDInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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Patent number: 6747174Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.Type: GrantFiled: January 28, 2003Date of Patent: June 8, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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Publication number: 20040097758Abstract: 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: ApplicationFiled: August 1, 2003Publication date: May 20, 2004Applicant: Solvay Fluor und Derivate GmbHInventors: Max Braun, Carsten Brosch
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Patent number: 6632949Abstract: 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: GrantFiled: July 10, 2002Date of Patent: October 14, 2003Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
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Publication number: 20030187280Abstract: (Per)haloethers having formula:Type: ApplicationFiled: February 4, 2003Publication date: October 2, 2003Applicant: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 6586626Abstract: 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: GrantFiled: September 24, 2001Date of Patent: July 1, 2003Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
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Patent number: 6489510Abstract: 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: GrantFiled: July 29, 1999Date of Patent: December 3, 2002Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Kerstin Eichholz, Werner Rudolph
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Publication number: 20020169276Abstract: 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: ApplicationFiled: May 9, 2002Publication date: November 14, 2002Applicant: AUSIMONT S.P.A.Inventors: Ivan Wlassics, Vito Tortelli
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Publication number: 20020156321Abstract: 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: ApplicationFiled: February 13, 2001Publication date: October 24, 2002Inventor: Robert George Syvret