Fluorine Patents (Class 568/683)
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Patent number: 6509509Abstract: A process for preparing perfluoropolyoxyalkylenes with hydroxyl end groups having structure: T1—CFW1—O—Rf—CFW2—T2 (I) wherein: T1, T2, are selected from —CH2OH, —F, —CF3, —CF2CF3 with the proviso that at least one of T1 and T2 is —CH2OH; W1 and W2 are selected from F, CF3; Rf is a perfluoropolyoxyalkylene chain having a number average molecular weight 500-10,000 comprising one or more units of the type —CF2CF2O—, —CF2O—, —C3F6O—, —CF2(CF2)zCF2O— (z=1,2); —CR4R5CF2CF2O— with R4 and R5 selected from H, Cl, perfluoroalkyl group; said process comprising the following steps: a) adding an ester precursor having structure (I) and T1, T2 end groups selected from —F, —CF3, —CF2CF3, —COOR (R=linear or branched alkyl group having a number of C atoms from 1 to 5), with the proviso that at least one of T1 and T2 is —COOR, in a reaction mixture fType: GrantFiled: December 29, 2000Date of Patent: January 21, 2003Assignee: Ausimont S.p.A.Inventors: Claudio Tonelli, Antonio Russo, Ezio Strepparola
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Publication number: 20020177739Abstract: A method for the preparation of sevoflurane which comprises (a) providing a liquid mixture of (CF3)2CHOCH2Cl, hydrogen fluoride, and an amine and (b) reacting the mixture, to form (CF3)2CHOCH2F.Type: ApplicationFiled: July 11, 2002Publication date: November 28, 2002Applicant: Medeva Pharmaceuticals PA, Inc.Inventor: Ross C. Terrell
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Patent number: 6469219Abstract: An improved process for preparing fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether(sevoflurane) by reacting 1,1,1,3,3,3-hexafluoro-2-propanol with formaldahyde and hydrogen fluoride either A) under distillation conditions or B) in the presence of or with the subsequent addition of a solvent capable of selectively extracting sevoflurane.Type: GrantFiled: March 16, 2000Date of Patent: October 22, 2002Assignee: Halocarbon Products CorporationInventors: Achot Pavlikovich Khrimian, Barry Malcolm Jones
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Patent number: 6448452Abstract: A polymer which contains monomer units formed by polymerization of a fluorine-containing diene of formula 1: CF2═CF(CF2)nCXYOCF═CF2 Wherein X and Y are hydrogen and chlorine, hydrogen and-bromine, hydrogen and iodine, fluorine and chlorine, fluorine and bromine, fluorine and iodine, chlorine and bromine, chlorine and iodine, bromine and bromine, bromine and iodine, or iodine and iodine and n is an integer from 1 to 3.Type: GrantFiled: April 25, 2001Date of Patent: September 10, 2002Assignee: Asahi Glass Company LimitedInventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
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Patent number: 6448451Abstract: The invention provides a process for purifying methyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether, comprising: passing a composition comprising methyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether and dimethyl ether through an evaporation zone; evaporating dimethyl ether by passing a gas stream through the composition; and removing the gas comprising dimethyl ether from the composition.Type: GrantFiled: June 5, 2001Date of Patent: September 10, 2002Assignee: Baxter International, Inc.Inventors: Ralph Rudzinski, Ralph Lessor
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Patent number: 6444859Abstract: The present invention relates to an anesthetic composition containing a fluoroether compound and a physiologically acceptable Lewis acid inhibitor. This composition exhibits improved stability and does not readily degrade in the presence of a Lewis acid.Type: GrantFiled: August 8, 2001Date of Patent: September 3, 2002Assignees: Abbott Laboratories, Central Glass Company LTDInventors: Christopher Bieniarz, Steve H. Chang, Keith R. Cromack, Shuyen L. Huang, Toshikazu Kawai, Manami Kobayashi, David Loffredo, Rajagopalan Raghavan, Earl R. Speicher, Honorate A. Stelmach
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Patent number: 6365769Abstract: Novel mixtures of perfluoroalkyl halides and derivatives thereof are described. These mixtures contain some compounds with a straight perfluoroalkyl group and some with a branched perfluoroalkyl group. Methods of preparation and use are also described.Type: GrantFiled: February 15, 2000Date of Patent: April 2, 2002Assignee: 3M Innovative Properties CompanyInventors: Frederick E. Behr, Rudolf J. Dams, Johan E. DeWitte, Donald F. Hagen
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Patent number: 6361713Abstract: Normally liquid, omega-hydrofluoroalkyl ether compounds (and selected mixtures thereof) have a saturated perfluoroaliphatic chain of carbon atoms interrupted by one or more ether oxygen atoms. The compounds can be prepared, e.g., by decarboxylation of the corresponding fluoroalkyl ether carboxylic acids and are useful, e.g., in cleaning and drying applications.Type: GrantFiled: August 17, 2000Date of Patent: March 26, 2002Assignee: 3M Innovative Properties CompanyInventors: George G. I. Moore, Richard M. Flynn, Miguel A. Guerra, John G. Owens
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Publication number: 20010056213Abstract: A method for the preparation of sevoflurane which comprises (a) providing a liquid mixture of (CF3)2CHOCH2Cl, hydrogen fluoride, and an amine and (b) reacting the mixture, to form (CF3)2CHOCH2F.Type: ApplicationFiled: June 21, 1999Publication date: December 27, 2001Inventor: ROSS C. TERRELL
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Patent number: 6316636Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.Type: GrantFiled: February 28, 1996Date of Patent: November 13, 2001Assignee: Rhone-Poulenc ChimieInventors: Robert Janin, Laurent Saint-Jalmes
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Patent number: 6315869Abstract: A perfluorovinyl ether of the formula: RfO(CF2CFXO)nCF═CF2 (1) in which Rf is a perfluoralkyl group, X is a fluorine atom or a trifluoromethyl group, and n is a number of 0 to 20 containing impurities is purified by removing a hydrogen fluoride adduct of the perfluorovinyl ether (1) through distillation, the perfluorovinyl ether (1) is distilled in the presence of a ketone or an ether having a lower boiling point than that of the perfluorovinyl ether (1) while refluxing such a solvent. This method can remove the hydrogen fluoride adduct of a perfluorovinyl ether as an impurity and provide a high purity perfluorovinyl ether.Type: GrantFiled: May 21, 1999Date of Patent: November 13, 2001Assignee: Daikin Industries, Ltd.Inventors: Shigeru Morita, Toshihiko Amano
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Patent number: 6303831Abstract: A method for fluoromethylation of a halogenated alcohol. The method includes refluxing a halogenated alcohol with a dihalomethane under basic conditions in a first solvent to form a halomethyl ether and fluorinating the halomethyl ether in the presence of a fluorinating agent.Type: GrantFiled: June 1, 2000Date of Patent: October 16, 2001Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Kornepati V. Ramakrishna
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Patent number: 6300526Abstract: Hydro-2,2-difluoroalkylvinylethers having the formula CF2═CH—O—RA (I) wherein RA is a radical containing fluorine, optionally containing halogens such as Cl, Br, I, hydrogen, functional groups CM, COOR′, CON(R′)2, SO2OR′, m wherein R′ is a C1-C5 alkyl, RA being selected from the following: a linear or branched, saturated or unsaturated C2-C20 fluoroalkyl, or a saturated or unsaturated C4-C6 fluorinated cyclic group wherein optionally from 1 to 2 carbon atoms are substituted with oxygen atoms, or a linear, branched saturated or unsaturated, C3-C15 fluorooxyalkyl group, containing one or Core oxygen atoms.Type: GrantFiled: July 29, 1999Date of Patent: October 9, 2001Assignee: Austmont S.p.A.Inventors: Walter Navarrini, Antonio Russo
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Patent number: 6288127Abstract: The present invention relates to an anesthetic composition containing a fluoroether compound and a physiologically acceptable Lewis acid inhibitor. This composition exhibits improved stability and does not readily degrade in the presence of a Lewis acid.Type: GrantFiled: November 23, 1999Date of Patent: September 11, 2001Assignee: Abbott Laboratories & Central Glass Co LTDInventors: Christopher Bieniarz, Steve H. Chang, Keith R. Cromack, Shuyen L. Huang, Toshikazu Kawai, Manami Kobayashi, David Loffredo, Rajagopalan Raghavan, Earl R. Speicher, Honorate A. Stelmach
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Patent number: 6271422Abstract: A method for fluoromethylation of an alcohol via halogenative decarboxylation. The method includes the step of reacting an alcohol of the formula R1C(CX3)2OH with an alpha-haloester of the formula X2CH2CO2R2 to form an alpha-alkoxy ester, wherein R1 is selected from the group consisting of hydrogen and alkyl groups, wherein R2 is selected from the group consisting of hydrogen and alkyl groups, wherein X, at each occurrence, is independently selected from the group consisting of hydrogen, bromine, fluorine, and chlorine, and wherein X2 is selected from the group consisting of bromine and chlorine. The resulting alpha-alkoxy ester is saponified to form an alpha-alkoxy acid which is heated at reflux with lead tetraacetate and a chlorinating agent to form a chloride compound of the formula R1C(CX3)2OCH2Cl. The chloride compound is converted to a fluoride compound of the formula R1C(CX3)2OCH2F with a fluorinating agent.Type: GrantFiled: June 1, 2000Date of Patent: August 7, 2001Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Kornepati V. Ramakrishna, Christopher Behme
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Patent number: 6245949Abstract: A method for fluoromethylating halogenated alcohols. The method includes the step of providing an alpha-halogenated alcohol of the formula R1C(CX3)2OH, wherein R1 is selected from the group consisting of hydrogen and alkyl groups. The alpha-halogenated alcohol is reacted with a first compound of the formula CH2(OR2)2 in the presence of an acid catalyst to form an acetal. The resulting acetal is then chlorinated with a chlorinating agent to form a chloride compound of the formula R1C(CX3)2OCH2Cl. The chloride compound is then converted to a fluoride compound of the formula R1C(CX3)2OCH2F using a fluorinating agent.Type: GrantFiled: June 1, 2000Date of Patent: June 12, 2001Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Kornepati V. Ramakrishna
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Patent number: 6225511Abstract: Fluorinated ethers of the formula: wherein R is hydrogen, fluorine, alkyl of 1 to 6 carbon atoms, or fluoroalkyl of 1 to 6 carbon atoms, R′ is hydrogen, alkyl of 1 to 6 carbon atoms, or fluoroalkyl of 1 to 6 carbon atoms, and R″ is fluorine, alkyl of 1 to 6 carbon atoms or fluoroalkyl of 1 to 6 carbon atoms are prepared by fluorinating a corresponding ether of formula: with a solid transition metal fluoride fluorinating agent such as cobaltic fluoride.Type: GrantFiled: March 14, 2000Date of Patent: May 1, 2001Assignee: Rhone-Poulenc Chemicals Ltd.Inventors: Owen Ross Chambers, Roderic Nigel Fraser Simpson
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Patent number: 6100434Abstract: A method for synthesizing fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether. The method includes the step of combining in the presence of aluminum trichloride a quantity of hexafluoroisopropanol and a quantity of either 1,3,5-trioxane or paraformaldehyde to produce sevochlorane. The resulting sevochlorane is then combined with an alkali metal fluoride to produce fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether.Type: GrantFiled: March 26, 1999Date of Patent: August 8, 2000Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Kornepati V. Ramakrishna, Christopher Behme
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Patent number: 6072088Abstract: A compound having the formula:CF.sub.3 CH.sub.2-w (H.sub.1-x CH.sub.2-y R.sub.m R'.sub.n CH.sub.1-z).sub.p H.sub.2-q CF.sub.3wherein w=0, 1 or 2; x=0 or 1; y=0, 1 or 2; m=0, 1 or 2; n=0 or 1; z=0 or 1; p=1 or 2; and q=0, 1 or 2; with the provisos that 1.ltoreq.w+x.ltoreq.2, 1.ltoreq.q+z.ltoreq.2, and p.multidot.y=p(m+2n)+(p-1)(x+z)+q+w+x+z-2; and wherein R includes the halogens having an atomic number greater than 9, and radicals having a valence of 1, and wherein R' is a group having a valence of 2, and a process for preparing the compound.Type: GrantFiled: August 10, 1999Date of Patent: June 6, 2000Assignee: Alliedsignal Inc.Inventor: Michael Van Der Puy
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Patent number: 6054626Abstract: Fluorinated ethers of the formula: ##STR1## wherein R is hydrogen, fluorine, alkyl of 1 to 6 carbon atoms, or fluoroalkyl of 1 to 6 carbon atoms, R' is hydrogen, alkyl of 1 to 6 carbon atoms, or fluoroalkyl of 1 to 6 carbon atoms, and R" is fluorine, alkyl of 1 to 6 carbon atoms or fluoroalkyl of 1 to 6 carbon atoms, e.g. Desflurane, are prepared by fluorinating a corresponding ether of formula: ##STR2## with a solid transition metal fluoride fluorinating agent such as cobaltic fluoride.Type: GrantFiled: November 10, 1993Date of Patent: April 25, 2000Assignee: Rhodia LimitedInventors: Owen Ross Chambers, Roderic Nigel Fraser Simpson
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Patent number: 6046368Abstract: Briefly, in one aspect, this invention provides a catalytic method of preparation of primary and secondary hydrofluoroethers, the process comprising reacting a fluorinated precursor material and an alkylating agent in the presence of a Lewis acid catalyst or a mixture comprising Lewis acid and Bronsted acid catalysts.Type: GrantFiled: March 17, 1998Date of Patent: April 4, 2000Assignee: 3M Innovative Properties CompanyInventors: William M. Lamanna, Richard M. Flynn, Daniel R. Vitcak, Zai-Ming Qiu
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Patent number: 6023002Abstract: Described is a reaction of a fluorinated alkoxide with an alkyl fluorovinylalkyl ether, the alkyl fluorovinylalkyl ether having alpha-beta carbon-carbon unsaturation relative to the ether oxygen, to produce a hydrofluoroether.Type: GrantFiled: January 26, 1998Date of Patent: February 8, 2000Assignee: 3M Innovative Properties CompanyInventors: Frederick E. Behr, Yuri Cheburkov
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Patent number: 6019909Abstract: A novel fluorinated hydrocarbon compound containing an oxygen or sulfur atom in its molecule, produced by the nucleophilic reaction of a fluorine compound with a hydrocarbon compound. This compound is useful as a lubricant for various applications and particularly excellent as an oil for refrigerators wherein hydrochlorofluorocarbon is used as the refrigerant and as a magnetic recording medium lubricant.Type: GrantFiled: July 21, 1995Date of Patent: February 1, 2000Assignee: Daikin Industries, Ltd.Inventors: Satoshi Ide, Katsuki Fujiwara, Masayuki Yamana, Yoshitaka Honda, Ikuo Yamamoto, Fumihiko Yamaguchi, Eiji Seki, Tatsuya Otsuka, Satoshi Ishida
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Patent number: 5990176Abstract: The present invention relates to an anesthetic composition containing a fluoroether compound and a physiologically acceptable Lewis acid inhibitor. This composition exhibits improved stability and does not readily degrade in the presence of a Lewis acid.Type: GrantFiled: January 27, 1997Date of Patent: November 23, 1999Assignees: Abbott Laboratories, Central Glass Company Ltd.Inventors: Christopher Bieniarz, Steve H. Chang, Keith R. Cromack, Shuyen L. Huang, Toshikazu Kawai, Manami Kobayashi, David Loffredo, Rajagopalan Raghavan, Earl R. Speicher, Honorate A. Stelmach
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Patent number: 5990359Abstract: Process for producing Sevoflurane anaesthetic which comprises reacting hexafluoroisopropyl alcohol with essentially pure bis(fluoromethyl)ether. The bis(fluoromethyl)ether is preferably obtained by the reaction of formaldehyde with hydrogen fluoride.Type: GrantFiled: June 30, 1998Date of Patent: November 23, 1999Assignee: Imperial Chemical Industries PLCInventors: Thomas Anthony Ryan, Leslie Burgess
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Patent number: 5969193Abstract: A method for the preparation of sevoflurane which comprises (a) providing a liquid mixture of (CF.sub.3).sub.2 CHOCH.sub.2 Cl, hydrogen fluoride, and an amine and (b) reacting the mixture, to form (CF.sub.3).sub.2 CHOCH.sub.2 F.Type: GrantFiled: August 18, 1997Date of Patent: October 19, 1999Assignee: Medeva Pharmaceuticals PA, Inc.Inventor: Ross C. Terrell
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Patent number: 5965779Abstract: The present invention provides processes for preparing 2,2,3,3,4-pentafluorooxetane and/or 2,2,3,3,4,4-hexafluorooxetane which comprises reacting 2,2,3,3-tetrafluorooxetane with fluorine gas, the process inhibiting decomposition of the oxetane ring during the reaction and producing a reduced amount of by-products.Type: GrantFiled: February 20, 1998Date of Patent: October 12, 1999Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Otsuka, Hirokazu Aoyama
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Patent number: 5917008Abstract: Polytetrafluoroethylene (PTFE) dispersions in an organic solvent, comprising:(A) from 2 to 40% by weight of PTFE in powder form;(B) from 50 to 95% by weight of an organic solvent;(C) from 0.5 to 10% by weight of a dispersing agent of formula:(R.sub.H -L).sub.y -(R.sub.F -L).sub.x R.sub.H (I)whereinx is an integer from 1 to 3;y is 0 or 1, with the proviso that x=1 when y=1;R.sub.H is a x-functional radical having an alkylic or polyoxyalkylenic structure;R.sub.F is (per)fluoropolyoxyalkylenic radical;L is a divalent organic group.Such dispersions are utilized for the surface treatment of metals, glass fibers, and the like, and in particular as mould release agents.Type: GrantFiled: June 19, 1998Date of Patent: June 29, 1999Assignee: Ausimont S.p.A.Inventors: Laura Montagna, Ezio Strepparola
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Patent number: 5886239Abstract: A method of preparing fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (sevoflurane) and structurally related monofluoromethyl ethers in which the monochloromethyl ether precursor thereof is reacted with a sterically hindered tertiary amine hydrofluoride salt.Type: GrantFiled: November 21, 1997Date of Patent: March 23, 1999Assignee: Baxter International Inc.Inventors: Linas V. Kudzma, Ralph A. Lessor, Leonid A. Rozov, Keith Ramig
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Patent number: 5856587Abstract: Extinguishing compositions comprising a liquid extinguishing agent constituted by hydrofluoropolyethers having general formulaHF.sub.2 CO(CF.sub.2 O).sub.n (CF.sub.2 CF.sub.2 O).sub.m CF.sub.2 Hwherein n and m are integers comprised between 0 and 20, excluding when m and m are contemporaneously 0 and having boiling point between 30.degree. and 200.degree. C. and having an O/C molar ratio between 0.5-1.Type: GrantFiled: March 5, 1997Date of Patent: January 5, 1999Assignee: Ausimot SpAInventors: Mario Visca, Gianfranco Spataro, Giuseppe Marchionni
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Patent number: 5814698Abstract: Polytetrafluoroethylene (PTFE) dispersions in an organic solvent, comprising:(A) from 2 to 40% by weight of PTFE in powder form;(B) from 50 to 95% by weight of an organic solvent;(C) from 0.5 to 10% by weight of a dispersing agent of formula:(R.sub.H --L).sub.y --(R.sub.F --L).sub.x R.sub.H (I)wherein:x is an integer from 1 to 3;y is 0 or 1, with the proviso that x=1 when y=1;R.sub.H is a x-functional radical having an alkylic or polyoxyalkylenic structure;R.sub.F is (per)fluoropolyoxyalkylenic radical;L is a divalent organic group.Such dispersions are utilized for the surface treatment of metals, glass fibers, and the like, and in particular as mold release agents.Type: GrantFiled: March 22, 1996Date of Patent: September 29, 1998Assignee: Ausimont S.p.A.Inventors: Laura Montagna, Ezio Strepparola
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Patent number: 5811596Abstract: The present invention provides a novel method of producing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether. It is a method of producing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether by bringing a polyether represented by the following general formula (1) into contact with a medium comprising hydrogen fluoride and an accelerant,R.sup.1 O(CH.sub.2 O).sub.n R.sup.2 ( 1)where R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1 -C.sup.10 alkyl or haloalkyl groups, where halogen is fluorine, chlorine or bromine, n is an integer of from 1 to 10, and both of R.sup.1 and R.sup.2 are not hydrogen at the same time.Type: GrantFiled: October 20, 1997Date of Patent: September 22, 1998Assignee: Central Glass Co., Ltd.Inventors: Toshikazu Kawai, Mineo Watanabe
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Patent number: 5763684Abstract: The present invention relates to a method of removing bisfluoromethyl ether contained in fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether in a simple, effective manner, and is characterized in that fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether containing bisfluoromethyl ether is brought into contact with zeolite.Type: GrantFiled: September 16, 1997Date of Patent: June 9, 1998Assignee: Central Glass Co., Ltd.Inventors: Toshikazu Kawai, Mineo Watanabe, Manami Kobayashi
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Patent number: 5753776Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: May 19, 1998Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5750807Abstract: A process for the production of a hydro(halo)fluorocarbon which comprises heating an .alpha.-fluoroether in the vapor phase at elevated temperature. .alpha.-fluoroethers are obtained by reacting a non-enolisable aldehyde with hydrogen fluoride to form an intermediate and reacting the intermediate with an alcohol or a halogenating agent. Novel .alpha.-fluoroethers are also provided.Type: GrantFiled: May 19, 1995Date of Patent: May 12, 1998Assignee: Imperial Chemical Industries PLCInventors: Leslie Burgess, Jane Lesley Butcher, Thomas Anthony Ryan, Peter Paul Clayton
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Patent number: 5750797Abstract: Briefly, in one aspect, this invention provides an improved alkylation process for the preparation of primary and secondary hydrofluoroether compounds, said process comprising:(1) combining in a polar, aprotic solvent:a) a fluorinated carbonyl-containing compound;b) an anhydrous source of fluoride ion;c) a tertiary or aromatic amine; andd) optionally, an effective amount of a phase transfer catalyst;(2) contacting the resulting mixture with an alkylating agent; and(3) recovering hydrofluoroether from the resulting product mixture.Type: GrantFiled: April 15, 1996Date of Patent: May 12, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Daniel R. Vitcak, Richard M. Flynn
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Patent number: 5741950Abstract: A method of preparing nonafluoroisobutyl methyl ether comprising the step of fluorinating heptafluoroisobutenyl methyl ether.Type: GrantFiled: December 16, 1996Date of Patent: April 21, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventor: Michael G. Costello
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Patent number: 5723684Abstract: A composition comprising bis(fluoromethyl)ether and less than an equimolar amount of water, a process for the production of the composition comprising contacting formaldehyde with hydrogen fluoride and separating at least some of the by-product water from bis(fluoromethyl)ether, and use of the composition for the production of difluoromethane.Type: GrantFiled: May 21, 1996Date of Patent: March 3, 1998Assignee: Imperial Chemical Industries PLCInventors: Jane Lesley Butcher, Thomas Anthony Ryan, Leslie Burgess
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Patent number: 5710317Abstract: A method for preparing difluoroacetic acid fluoride, which comprises reacting a 1-alkoxy-1,1,2,2-tetrafluoroethane of the formula HCF.sub.2 CF.sub.2 OR.sup.1 wherein R.sup.1 is a C.sub.1-4 alkyl group in a gas phase in the presence of a metal oxide catalyst.Type: GrantFiled: July 26, 1995Date of Patent: January 20, 1998Assignee: Asahi Glass Company Ltd.Inventors: Kazuya Oharu, Seisaku Kumai
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Patent number: 5705710Abstract: This invention relates to a method of synthesizing 1,1,1,3,3,3-hexafluoroisopropyl ether compounds from the reaction of methoxymalanonitrile with a bromine trifluoride composition.Type: GrantFiled: January 15, 1997Date of Patent: January 6, 1998Assignee: University of Iowa Research FoundationInventors: Max T. Baker, John H. Tinker, Jan A. Ruzicka
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Patent number: 5684210Abstract: It is possible to obtain fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether which has a high purity and in which an impurity making the purification by distillation difficult has been removed, by contacting a crude fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether with a Bronsted acid(s), a Lewis acid(s) or an acid(s) fixed to a resin or the like.Type: GrantFiled: November 10, 1995Date of Patent: November 4, 1997Assignee: Central Glass Company, LimitedInventors: Toshikazu Kawai, Takaaki Yoshimura, Mineo Watanabe, Manami Kumakura
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Patent number: 5684211Abstract: The present invention provides a method of purifying fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether by adding a compound selected from hydroxides of, hydrogenphosphates of, phosphates of, hydrogencarbonates of, borates of or sulfites of alkali metals, or alkali metal salts of acetic acid or of phthalic acid, or boric acid to fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether, add then by distillation. It is possible to effectively suppress the decomposition, at the time of distillation, of fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether that is used as a pharmaceutical and particularly as an inhalation anesthetic and thus to obtain fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether of high purity.Type: GrantFiled: November 16, 1995Date of Patent: November 4, 1997Assignee: Central Glass Company, LimitedInventors: Toshikazu Kawai, Takaaki Yoshimura, Manami Kumakura, Mineo Watanabe
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Patent number: 5679576Abstract: The present invention provides a method in which organic matter in the product accompanied with a non-reacted hydrogen fluoride can be handled without damaging the apparatus, using a cross-linked cyanopropylmethylphenylsilicone capillary column with which impurities of very small amounts can be separated, and with which non-reacted raw materials and by-products, which have a wide range of boiling points can be quantitated.Type: GrantFiled: December 5, 1995Date of Patent: October 21, 1997Assignee: Central Glass Co., Ltd.Inventors: Toshikazu Kawai, Takaaki Yoshimura, Mineo Watanabe, Manami Kamakura
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Patent number: 5648560Abstract: A process for preparing perhaloethers from perhaloolefins by reacting at least one fluorooxy compound R.sub.x --OF, wherein R.sub.x is a perhaloalkyl radical, with a perfluoroolefin in a liquid phase, optionally containing an organic solvent inert to the perfluoroolefin, while maintaining the temperature of the liquid phase in the range of -30.degree. to -120.degree. C. The process includes continuously feeding to the liquid phase a stream of an inert gas and a gaseous stream of the fluorooxy compound.Type: GrantFiled: December 9, 1994Date of Patent: July 15, 1997Assignee: Ausimont S.p.A.Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani, Walter Navarrini
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Patent number: 5637776Abstract: A process for the production of a hydro(halo)fluorocarbon which comprises heating an .alpha.-fluoroether in the vapour phase at elevated temperature. .alpha.-fluoroethers are obtained by reacting a non-enolisable aldehyde with hydrogen fluoride to form an intermediate and reacting the intermediate with an alcohol or a halogenating agent. Novel .alpha.-fluoroethers are also provided.Type: GrantFiled: November 30, 1995Date of Patent: June 10, 1997Assignee: Imperial Chemical Industries PLCInventors: Leslie Burgess, Jane L. Butcher, Thomas A. Ryan, Peter P. Clayton
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Patent number: 5623091Abstract: A composition comprising bis(fluoromethyl)ether and less than an equimolar amount of water, a process for the production of the composition comprising contacting formaldehyde with hydrogen fluoride and separating at least some of the by-product water from bis(fluoromethyl)ether, and use of the composition for the production of difluoromethane.Type: GrantFiled: September 5, 1995Date of Patent: April 22, 1997Assignee: Imperial Chemical Industries PLCInventors: Jane L. Butcher, Thomas A. Ryan, Leslie Burgess
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Patent number: 5571870Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: May 10, 1994Date of Patent: November 5, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5557012Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoroether polymers that can be prepared by fluorinating polymers made by the polymerization of acetals, ketals, polyacetals, polyketals and orthoesters with elemental fluorine.Type: GrantFiled: June 5, 1995Date of Patent: September 17, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5545769Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.Type: GrantFiled: September 29, 1994Date of Patent: August 13, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
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Patent number: RE35568Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine .[.group.]. in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and .Iadd.halogenated .Iaddend.alkoxy-substituted .[.halogenated.]. aliphatic groups, wherein the method comprises the step of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.Type: GrantFiled: November 16, 1994Date of Patent: July 22, 1997Assignee: Ohmeda Pharmaceutical Products Division Inc.Inventors: Donald F. Halpern, Mark L. Robin