Utilizing Halogen Fluoride Or A Mixture Of Elemental Fluorine And Another Elemental Halogen Patents (Class 570/161)
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Publication number: 20030105368Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.Type: ApplicationFiled: September 28, 2001Publication date: June 5, 2003Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
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Publication number: 20030036668Abstract: Novel techniques are disclosed for the direct fluoridation of organic compounds by treatment with fluorine gas in a reaction mixture comprising hydrofluoric acid and at least one of water and formic acid. The techniques are particularly applicable to aromatic organic compounds and beta-dicarbonyl compounds. Increased efficiency of reaction is observed, together with improvements in yield and purity of product, with especially beneficial effects being apparent at low temperatures.Type: ApplicationFiled: June 3, 2002Publication date: February 20, 2003Inventors: Roy Dennis Bowden, John Steward Moilliet
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Publication number: 20020143215Abstract: Disclosed is an improved HFC manufacturing processes of the type which produces an intermediate product stream that includes a mixture of HF and at least one compound, usually an HCFC, which is relatively resistant to further fluorination. The improvement involves separating the unreactive compound(s) from the product stream, preferably using liquid:liquid phase separation, and substantially avoiding recycle of the unreactive compound to the fluorination reaction. The separated unreactive compound(s) are substantially free of HF.Type: ApplicationFiled: January 25, 2002Publication date: October 3, 2002Inventors: Hsueh Sung Tung, Clayton Herbert Carson, Hang Thanh Pham
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Patent number: 6426439Abstract: Continuous process for the preparation of pentafluoroethyl iodide from iodine, iodine pentafluoride and tetrafluoroethylene, which comprises dissolving the iodine in iodine pentafluoride and continuously feeding the resulting solution to a vertical bubble column (1), which is filled with iodine pentafluoride and at its lower end has a feed line for tetrafluoroethylene, where the reaction zone is maintained at from 85 to 95° C., preferably 90° C., and the pentafluoroethyl iodide formed escapes in gaseous form at the top of the reactor (1), is liquefied in a downstream cooled condenser and is drawn off into storage vessels.Type: GrantFiled: December 30, 1999Date of Patent: July 30, 2002Assignee: Clariant GmbHInventors: Hans-Bodo Richter, Norbert Paul, Rudolf Huber
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Patent number: 6384289Abstract: A process is provided which allows a 1,4-bis(difluoroalkyl)benzene derivative to be produced inexpensively by a simple procedure without requiring any special facility. This process comprises causing a compound (A) of the following formula (1): wherein X1, X2, X3, and X4 independently stand for an oxygen or sulfur atom, Y1 and Y2 independently stand for a group of the formula: —CnH2n—, in which n is 2 or 3, k is an integer in the range of 0 to 4, G stands for a halogen group, an alkyl group, a perfluoroalkyl group, or an alkoxy group, and m is an integer in the range of 0 to 4, to react with a fluorine-containing species, the molar ratio of the fluorine-containing species to compound (A) being in the range of 20-40. The process is carried out in the presence of a bromine-containing compound, which is in an amount of 2 to 3 equivalences to the amount of compound (A), in an organic solvent at −80° C. to 30° C.Type: GrantFiled: January 11, 2001Date of Patent: May 7, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Seiichi Teshima, Yoshinobu Asako
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Publication number: 20020038061Abstract: 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: ApplicationFiled: September 25, 2001Publication date: March 28, 2002Applicant: Huntsman Petrochemical CorporationInventors: Robert Janin, Laurent Saint-Jalmes
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Publication number: 20010003786Abstract: The invention relates to the synthesis of difluoromethane by gas-phase catalytic fluorination of methylene chloride.Type: ApplicationFiled: January 18, 2001Publication date: June 14, 2001Applicant: ELF ATOCHEM S.A.Inventors: Benoit Requieme, Sylvain Perdrieux, Bernard Cheminal, Eric Lacroix, Andre Lantz
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Publication number: 20010002425Abstract: A process is provided which allows a 1,4-bis(difluoroalkyl)benzene derivative to be produced inexpensively by a simple procedure without requiring any special facility.Type: ApplicationFiled: January 11, 2001Publication date: May 31, 2001Applicant: Nippon Shokubai Co., Ltd., a Japan CorporationInventors: Seiichi Teshima, Yoshinobu Asako
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Patent number: 6077819Abstract: A process is disclosed for recovering HF from a product mixture comprising HF and at least one compound having the formula CF.sub.3 CCl.sub.2+x F.sub.1-x (where x is 0 or 1). The process includes the steps of distilling the product mixture to remove all products which have a lower boiling point than the lowest boiling azeotrope containing HF and said at least one compound; and distilling said azeotrope to recover HF as an azeotropic composition containing HF and said at least one compound. Also disclosed are azeotrope and azeotrope-like compositions which consist essentially of hydrogen fluoride in combination with from about 10 to 27 mole percent CCl.sub.3 CF.sub.3 or from about 35 to 56 mole percent CCl.sub.2 FCF.sub.3.Type: GrantFiled: November 1, 1993Date of Patent: June 20, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Barry A. Mahler, Ralph N. Miller, V. N. Mallikarjuna Rao
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Patent number: 6034288Abstract: Prior to carrying out a gaseous phase chemical reaction, a liquid phase organic compound which is prone to degrade is vaporised at elevated pressures with the aid of a second compound. In one embodiment of the invention, vaporisation is effected by co-vaporising a mixture of the two compounds in a vaporiser. In another embodiment, the first compound is injected into a hot gaseous stream and undergoes atomisation into droplets which then vaporise within the gaseous stream. The second compound is used to assist the atomisation process and/or to sweep atomised droplets of the first compound away from hot surfaces where the first compound would otherwise tend to undergo degradation if the droplets are allowed to reside in contact with such surfaces.Type: GrantFiled: September 25, 1995Date of Patent: March 7, 2000Assignee: Imperial Chemical Industries PLCInventors: John David Scott, Charles Brian Blake, Paul Nicholas Ewing
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Patent number: 5847243Abstract: A vic-dichloro-fluorinated alkene of the formula: R.sup.1 --CCl.dbd.CCl--R.sup.2, and a fluorinated alkane of the formula: R.sup.1 --CR.sup.3 R.sup.4 --CR.sup.5 R.sup.6 --R.sup.2, wherein each of R.sup.1 and R.sup.2 independently represents a perfluoroalkyl group or both of R.sup.1 and R.sup.2 form together a perfluoroalkylene group, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently represent hydrogen or fluorine, are produced from an inexpensive raw material. More specifically, hexachlorocyclopentadiene is reacted with gaseous chlorine using an antimony catalyst, and then the reaction product is reacted with hydrogen fluoride to give 1,2-dichlorohexafluorocyclopentene. Thus-obtained compound is either (i) hydrogenated, or (ii) treated with a fluorinating agent to substitute the chlorine atoms by fluorine atoms, and then hydrogenated, to give the intended fluorinated alkane.Type: GrantFiled: December 27, 1996Date of Patent: December 8, 1998Assignees: Japan as represented by Director General of the Agency of Industrial Science and Technology, Nippon Zeon Co. Ltd.Inventors: Akira Sekiya, Toshiro Yamada, Kazunori Watanabe
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Patent number: 5789580Abstract: A process for the preparation of a selectively fluorinated organic compound, which process includes reaction of a precursor of said organic compound, the precursor containing at least one Group VI element selected from sulfur, selenium and tellurium, with a fluorinating agent and another halogenating agent and characterized in that the fluorinating agent is elemental fluorine.Type: GrantFiled: April 25, 1996Date of Patent: August 4, 1998Assignee: British Nuclear Fuels plcInventors: Richard Dickinson Chambers, Graham Sandford
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Patent number: 5780691Abstract: The invention provides a process for production of 1,1,1,2,3,3,3-heptafluoropropane, HFC-227ea. In particular, the invention provides an inexpensive process for producing HFC-227ea in good yield by reacting 1,1,1,3,3,3-hexafluoropropane, HFC-236fa, with elemental fluorine in an inert gas.Type: GrantFiled: December 23, 1996Date of Patent: July 14, 1998Assignee: Allied Signal Inc.Inventors: Hsueh Sung Tung, Lois Anne Ellis
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Patent number: 5710351Abstract: A process for producing hexafluoroethane which comprises reacting a hydrofluorocarbon containing two carbon atoms in the molecule with fluorine gas at an elevated temperature in a vapor phase in the presence of a diluent gas.Type: GrantFiled: April 10, 1996Date of Patent: January 20, 1998Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Tetsuo Nakajo, Tatsuharu Arai, Toshio Ohi
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Patent number: 5705718Abstract: To remove the unsaturated impurities (in particular 1-chloro-2,2-difluoroethylene and polyfluoropropenes) present in crude 1,1,1,2-tetrafluoroethane (F134a), a gaseous mixture of crude F134a, of hydrofluoric acid and of chlorine is treated in gaseous phase in the presence of a fluorination catalyst at a temperature of between 100.degree. and 300.degree. C. and at a pressure between atmospheric pressure and 2.5 MPa, the molar ratio HF/F134a being between 0.05 and 0.5 and the molar ratio Cl.sub.2 /F134a between 0.0001 and 0.1.Type: GrantFiled: October 15, 1996Date of Patent: January 6, 1998Assignee: Elf Atochem S.A.Inventors: Bernard Cheminal, Andre Lantz
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Patent number: 5324873Abstract: Hydrogen fluoride and 1,1,1-trifluoro-2-chloroethane forms an azeotropic mixture. A mixture comprising hydrogen fluoride and 1,1,1-trifluoro-2-chloroethane is phase separated when it is cooled to a temperature below 7.degree. C. 1,1,1-Trifluoro-2-chloroethane is purified effectively from the mixture by cooling the mixture to form an upper liquid phase and a lower liquid phase and distilling the lower liquid phase so that the hydrogen fluoride is removed as an azeotropic distillate and 1,1,1-trifluoro-2-chloroethane substantially free from hydrogen fluoride is obtained as a bottom product.Type: GrantFiled: February 12, 1993Date of Patent: June 28, 1994Assignee: Daikin Industries LimitedInventors: Takehide Tsuda, Nobuyoshi Iwashita, Satoshi Komatsu, Satoshi Koyama
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Patent number: 5283380Abstract: This invention relates to an improved method of preparing the active telogen CF.sub.3 CFClI. The process comprises reacting chlorotrifluoroethylene, iodine, and iodine pentafluoride in the presence of an aluminum bromide catalyst at a temperature above about 25.degree. C.Type: GrantFiled: June 11, 1993Date of Patent: February 1, 1994Assignee: Dow Corning CorporationInventors: Bernard Boutevin, Gerald A. Gornowicz
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Patent number: 5258561Abstract: A chlorofluorination process is disclosed which employs a catalyst comprising chromium oxide for producing halohydrocarbons of the formula CHXFCF.sub.3 (where X is selected from Cl and F). The process is characterized by feeding a combination of components comprising, (i) at least one halohydrocarbon starting compound of the formula CY.sub.3 CH.sub.2 R.sup.1 (where R.sup.1 is selected from the group of H and F and each Y is independently selected from the group of Cl and F), (ii) hydrogen fluoride and (iii) chlorine to a reaction zone; contacting said combination of compounds in said reaction zone with a catalyst comprising chromium oxide at an elevated temperature to produce reaction zone products containing halohydrocarbon reaction products of the formula CHXFCF.sub.3 together with halohydrocarbons of the formula CZ.sub.3 CHR.sup.2 R.sup.3 (wherein R.sup.2 is selected from the group of H and Cl, R.sup.Type: GrantFiled: November 6, 1992Date of Patent: November 2, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Mario J. Nappa, V. N. Mallikarjuna Rao
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Patent number: 4952708Abstract: An improved method for making biaryl compounds is disclosed, in which an aromatic acid halide having at least one strong electron-withdrawing group attached to or within the aromatic ring is reacted with at least one polysilane in the presence of an effective amount of a transition metal catalyst.Type: GrantFiled: April 3, 1989Date of Patent: August 28, 1990Assignee: General Electric CompanyInventors: Jonathan D. Rich, Terry E. Krafft, Philip J. McDermott, Tony C. Chang
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Patent number: 4760205Abstract: New processes for the preparation of 2-iodo-perfluoro-2-methyl-butane and the corresponding -pentane are described. In one process, perfluoro-2-methyl-2-butene or the corresponding -pentene is reacted in an amount of at least 5 mol with a mixture of 2 mol of iodine and 1 mol of iodine pentafluoride in the presence of more than 1 mol of at least one fluoride of a metal of group I of the periodic table of the elements under the autogenous pressure of the reaction mixture at 170.degree. to 220.degree. C. for 2 to 30 hours. In another process, the same perfluoroolefins are reacted, as the starting substances, with iodine and an alkali metal fluoride in the presence of at least 1 mol of a soluble silver salt per mole of the perfluorinated olefin at 20.degree. to 100.degree. C. for 0.5 to 10 hours. After working up by distillation, the pure iodoperfluoroalkanes are obtained. They are suitable for numerous reactions, but in particular as a packing for lasers.Type: GrantFiled: December 31, 1986Date of Patent: July 26, 1988Assignee: Hoechst AktiengesellschaftInventors: Anton Probst, Klaus Raab, Konrad von Werner
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Patent number: 4513154Abstract: A process for consecutive-competitive gas phase halogenation of organic compounds, i.e. alkanes, alkenes and benzene, alkyl benzenes and alkenyl benzenes containing labile hydrogens and having no more than 12 and 9 carbon atoms, respectively, in a thin reaction film on the surface of a porous barrier for production of highly halogenated products by substantial suppression of diffusion of partially halogenated intermediates away from the reaction film is disclosed.Type: GrantFiled: July 28, 1980Date of Patent: April 23, 1985Assignee: Allied CorporationInventor: Bruce E. Kurtz