Preparing Unsaturated Compound Patents (Class 570/153)
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Patent number: 11219875Abstract: Disclosed is a device for the synthesis of a radiotracer, including a universal confined enclosure designed for the insertion of a specific synthesis cassette of the radiotracer and the removal of same. The synthesis cassette includes a synthesis module designed to receive reagents and a radioisotope for the synthesis of the radiotracer. An inner connector plate includes at least one inlet, designed to be connected to a radioisotope admission and also to the inlet of the cassette, and an outlet, designed to be connected to a syringe to be filled with the radiotracer and also to the outlet of the cassette. Such a synthesis device can be installed in a facility including, in a confined room, as well as such devices normally arranged in a storage area, a synthesis station, a radioisotope admission, at least one window for communication to the outside, and a manipulator robot.Type: GrantFiled: April 14, 2016Date of Patent: January 11, 2022Assignee: PMBInventors: Laurent Tanguy, Jerome Corneille, Bertrand Loubaton, Marc Delmas, Alain Perez Delaume
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Patent number: 11008267Abstract: The disclosure relates to a method for hydrofluorination of an olefin of the formula: RCX?CYZ to produce a hydrofluoroalkane of formula RCXFCHYZ or RCXHCFYZ, wherein X, Y, and Z are independently the same or different and are selected from the group consisting of H, F, Cl, Br, and C1-C6 alkyl which is partially or fully substituted with chloro or fluoro or bromo; and R is a C1-C6 alkyl which is unsubstituted or substituted with chloro or fluoro or bromo, comprising reacting the olefin with HF in the liquid-phase, in the presence of SbF5, at a temperature ranging from about ?30° C. to about 65° C. and compositions formed by the process.Type: GrantFiled: May 28, 2019Date of Patent: May 18, 2021Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Xuehui Sun, Mario Joseph Nappa, Karl Krause
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Patent number: 10800720Abstract: The invention relates to a process comprising contacting a composition comprising a (hydro)halocarbon and a compound of formula Rf—C?CX with a basic solution comprising an hydroxide, an alkoxide and/or an amide to reduce the concentration of Rf—C?CX, wherein Rf is a perfluorinated alkyl group and X is H, F, Cl, Br, or I. The invention further relates to process for preparing a (hydro)halocarbon comprising (i) converting a starting material, optionally in the presence of HF and/or a catalyst, to a composition comprising the (hydro)halocarbon and a compound of formula Rf—C?CX, wherein Rf is a perfluorinated alkyl group and X is H, F, Cl, Br, or I; (ii) contacting the composition with a basic solution comprising an hydroxide, an alkoxide and/or an amide to reduce the concentration of the compound of formula Rf—C?CX; and (iii) recovering the (hydro)halocarbon.Type: GrantFiled: January 19, 2018Date of Patent: October 13, 2020Assignee: MEXICHEM FLUOR S.A. DE C.V.Inventor: Andrew Paul Sharratt
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Patent number: 10392326Abstract: The present invention provides an economically advantageous method for efficiently producing a fluorine-containing compound while ensuring high conversion of the starting compound, reducing production of 245cb, and reducing equipment costs and energy costs.Type: GrantFiled: January 19, 2016Date of Patent: August 27, 2019Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Daisuke Karube, Takehiro Chaki
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Patent number: 10377686Abstract: An efficient method for producing 1-chloro-2,3,3,3-tetorafluoropropene from 1,1-dichloro-2,3,3,3-tetrafluoropropene is provided. The method produces 1-chloro-2,3,3,3-tetorafluoropropene by reducing 1,1-dichloro-2,3,3,3-tetrafluoropropene with fewer over-reduced by-products, such as 2,3,3,3-tetrafluoropropene and 1,1,1,2-tetrafluoropropane. In the method, 1,1-dichloro-2,3,3,3-tetrafluoropropene reacts with hydrogen in a gas phase in the presence of a palladium catalyst-carrying carrier, in which a palladium catalyst having a specific surface area of 40 m2/g or less is carried on the carrier.Type: GrantFiled: August 20, 2018Date of Patent: August 13, 2019Assignee: AGC Inc.Inventors: Shingo Nomura, Hidekazu Okamoto, Hirokazu Takagi
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Patent number: 10343148Abstract: A catalyst structure includes a plurality of metal oxides formed on a support, where the support includes zirconia and/or silica. The metal oxides include at least three metals selected from the group consisting of chromium, iron, nickel, and a platinum group metal. The catalyst structure can be used in an oxidative dehydrogenation (ODH) reaction process for converting an alkane to an olefin. In some embodiments, carbon dioxide utilized in the ODH reaction process is obtained from a flue gas derived from a fossil fuel burning power plant.Type: GrantFiled: December 1, 2016Date of Patent: July 9, 2019Assignee: SOUTHERN RESEARCH INSTITUTEInventors: Amit Goyal, Jadid Samad
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Patent number: 10258634Abstract: The invention relates to the field of medicine, in particular to the field of veterinary medicine. The invention relates to glucocorticoids, especially ciclesonide or a pharmaceutically acceptable derivative or salt thereof, for the treatment of airway disease in horses, such as pulmonary disease, preferably recurrent airway obstruction (RAO), Summer Pasture Associated Obstructive Pulmonary disease (SPAOPD), and inflammatory airway disease (IAD).Type: GrantFiled: October 13, 2016Date of Patent: April 16, 2019Assignee: Boehringer Ingelheim Vetmedica GmbHInventors: Balazs Albrecht, Michael Aven, Janine Lamar, Ingo Lang
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Patent number: 10189758Abstract: To provide a method for producing a hydrofluoroolefin, wherein formation of an over-reduced product having hydrogen added to an aimed hydrofluorolefin and an over-reduced product having some of fluorine atoms in the aimed product replaced with hydrogen atoms, as by-products, is suppressed. A method for producing a hydrofluoroolefin, which comprises reacting a specific chlorofluoroolefin with hydrogen in the presence of a catalyst supported on a carrier, to obtain a specific hydrofluoroolefin, wherein the catalyst is a catalyst composed of particles of an alloy containing at least one platinum group metal selected from the group consisting of palladium and platinum, and gold, and the proportion of the gold at the surface of the alloy particles is from 5 to 30 mass % per 100 mass % in total of the platinum group metal and the gold at the surface of the alloy particles.Type: GrantFiled: June 1, 2017Date of Patent: January 29, 2019Assignee: AGC Inc.Inventors: Xu Wang, Shinji Terazono, Yuki Hayasaka, Toshio Suzuki, Satoshi Kawaguchi, Mitsugu Kasagawa
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Patent number: 9988327Abstract: A method for producing a hydrofluoroolefin is provided. The formation of by-products of an over-reduced product having hydrogen added to a material chlorofluoroolefin and an over-reduced product having not only chlorine atoms but also fluorine atoms in the chlorofluoroolefin replaced with hydrogen atoms is suppressed in the method. The method includes reacting a specific chlorofluoroolefin with hydrogen in the presence of a catalyst supported on a carrier to obtain the hydrofluoroolefin. The catalyst is a catalyst composed of an alloy containing at least one platinum group element of palladium and platinum, and at least one second element of manganese, copper, aluminum, gold, lithium, sodium, potassium, magnesium, silver, zinc, cadmium, indium, silicon, germanium, tin, lead, arsenic, antimony, and bismuth.Type: GrantFiled: February 16, 2017Date of Patent: June 5, 2018Assignee: Asahi Glass Company, LimitedInventors: Shinji Terazono, Xu Wang, Masahiro Kanda, Satoshi Kawaguchi, Mitsugu Kasagawa
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Patent number: 9944852Abstract: The present invention is a 1H-Heptafluorocyclopentene having a purity of 99.9 wt % or more and an organochlorine-based compound content of 350 ppm by weight or less. The present invention provides a high-purity 1H-Heptafluorocyclopentene that may be useful as a plasma reaction gas for semiconductors.Type: GrantFiled: February 19, 2014Date of Patent: April 17, 2018Assignee: ZEON CORPORATIONInventor: Tatsuya Sugimoto
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Patent number: 9643904Abstract: A method for preparing 2,3,3,3-tetrafluoropropene, including: a) introducing hexafluoropropylene and hydrogen to a first reactor for reaction in the presence of a catalyst to obtain a first mixture; b) washing and drying the first mixture, and introducing the treated first mixture to a first distillation column to obtain 1,1,1,2,3,3-hexafluoropropane, 1,1,1,2,3-pentafluoropropene, and hexafluoropropylene; recycling the 1,1,1,2,3,3-hexafluoropropane to the first reactor, and introducing the 1,1,1,2,3-pentafluoropropene and the hexafluoropropylene to a second distillation column to yield hexafluoropropylene and 1,1,1,2,3-pentafluoropropene; and recycling the hexafluoropropylene to the first reactor; c) introducing the 1,1,1,2,3-pentafluoropropene and hydrogen to a second reactor in the presence of a catalyst to obtain a second mixture; and d) washing and drying the second mixture, and introducing the second mixture to a third distillation column to yield 1,1,1,2,3-pentafluoropropane; and recycling the 1,1,1,2,3Type: GrantFiled: December 13, 2016Date of Patent: May 9, 2017Assignees: ZHEJIANG QUZHOU JUXIN FLUORINE CHEMICAL CO., LTD., ZHEJIANG QUHUA FLUOR-CHEMISTRY CO., LTD.Inventors: Jun Lei, Aiguo Wang, Bo Yang, Yan Zhang, Huadong Zhou, Yang Zhao, Yi Zhu, Haili Xia, Haojin Shi
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Patent number: 9328043Abstract: The present invention relates, in part, an improved process for the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf). In certain non-limiting embodiments, the invention relates to methods for improving process efficiency during the fluorination of 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, and/or 1,1,1,2,3-pentachloropropane to 2-chloro-3,3,3-trifluoropropene by separating and recycling unreacted HF, unreacted starting materials, and/or certain process intermediates from the 2-chloro-3,3,3-trifluoropropene product stream.Type: GrantFiled: February 25, 2013Date of Patent: May 3, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Selma Bektesevic, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu
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Patent number: 9249072Abstract: The invention provides a process comprising contacting (1243zf) or (253fb) with hydrogen in the presence of a hydrogenation catalyst to produce a composition comprising 1,1,1-trifluoropropane (263fb).Type: GrantFiled: July 18, 2012Date of Patent: February 2, 2016Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew P. Sharratt, Claire E. McGuinness, Emma J. Hodgson
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Patent number: 9139495Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.Type: GrantFiled: November 26, 2014Date of Patent: September 22, 2015Assignee: Occidental Chemical CorporationInventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
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Patent number: 9085504Abstract: Various compositions, including particularly solvent compositions, containing fluorinated olefins, including particularly tetra- and penta-fluorpropenes, in a variety of applications are disclosed.Type: GrantFiled: September 4, 2007Date of Patent: July 21, 2015Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Rajiv R. Singh, Raymond H. Thomas, Gary Knopeck
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Patent number: 9040760Abstract: This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl?CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.Type: GrantFiled: October 27, 2011Date of Patent: May 26, 2015Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
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Patent number: 9029617Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides several routes for forming HCFO-1233zd from 3,3,3-trifluoropropene (FC-1234zf).Type: GrantFiled: July 14, 2014Date of Patent: May 12, 2015Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, David Nalewajek, Andrew Joseph Poss, Yian Zhai
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Patent number: 9018428Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.Type: GrantFiled: March 14, 2013Date of Patent: April 28, 2015Assignee: Honeywell International Inc.Inventor: Stephen A. Cottrell
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Publication number: 20150105595Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.Type: ApplicationFiled: December 15, 2014Publication date: April 16, 2015Inventors: Daniel C. Merkel, Hsueh S. Tung
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Patent number: 9000241Abstract: The disclosure describes a process for dehalogenation of chlorofluorocompounds. The process comprises contacting a saturated chlorofluorocompound with hydrogen in the presence of a catalyst at a temperature sufficient to remove chlorine and/or fluorine substituents to produce a fluorine containing terminal olefin.Type: GrantFiled: October 20, 2011Date of Patent: April 7, 2015Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Ekaterina N. Swearingen, Allen Capron Sievert, Xuehui Sun
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Patent number: 8987532Abstract: Disclosed is a process for producing 1,2-dichloro-3,3,3-trifluoropropene, which is characterized by that 1-halogeno-3,3,3-trifluoropropene represented by the general formula [1]: (In the formula, X represents a fluorine atom, chlorine atom or bromine atom.) is reacted with chlorine in a gas phase in the presence of a catalyst. It is possible by this process to produce 1,2-dichloro-3,3,3-trifluoropropene in an industrial scale with good yield by using 1-halogeno-3,3,3-trifluoropropene, which is available with a low price, as the raw material.Type: GrantFiled: April 1, 2014Date of Patent: March 24, 2015Assignee: Central Glass Company, LimitedInventors: Satoru Okamoto, Yoshio Nishiguchi, Fuyuhiko Sakyu
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Publication number: 20150045590Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides several routes for forming HCFO-1233zd from 3,3,3-trifluoropropene (FC-1234zf).Type: ApplicationFiled: July 14, 2014Publication date: February 12, 2015Inventors: Haridasan K. Nair, David Nalewajek, Andrew Joseph Poss, Yian Zhai
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Publication number: 20150008357Abstract: To provide a method for efficiently separating 2,3,3,3-tetrafluoropropene (HFO-1234yf) and chloromethane (R40) from a composition comprising HFO-1234yf and R40. An azeotrope-like composition comprising from 58 to 78 mol % of HFO-1234yf and from 22 to 42 mol % of R40, and a method for producing HFO-1234yf, which comprises steps of distilling an initial mixture containing HFO-1234yf in a content exceeding 63 mol % in the total amount of HFO-1234yf and R40, thereby to separate the initial mixture into a first fraction in which the content of HFO-1234yf in the total amount of HFO-1234yf and R40 is lower than the content of HFO-1234yf in the total amount of HFO-1234yf and R40 in the initial mixture, and a second fraction in which the content of HFO-1234yf in the total amount of HFO-1234yf and R40 is higher than the content of HFO-1234yf in the total amount of HFO-1234yf and R40 in the initial mixture, and then obtaining HFO-1234yf having a reduced R40 concentration, from the second fraction.Type: ApplicationFiled: September 26, 2014Publication date: January 8, 2015Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Shoji Furuta, Tetsuo Otsuka
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Publication number: 20150011804Abstract: The present invention relates, in part, an improved process for the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf). In certain non-limiting embodiments, the invention relates to methods for improving process efficiency during the fluorination of 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, and/or 1,1,1,2,3-pentachloropropane to 2-chloro-3,3,3-trifluoropropene by separating and recycling unreacted HF, unreacted starting materials, and/or certain pro cess intermediates from the 2-chloro-3,3,3-trifluoropropene product stream.Type: ApplicationFiled: February 25, 2013Publication date: January 8, 2015Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Selma Bektesevic, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu
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Publication number: 20140357907Abstract: Disclosed is a process for producing 1,2-dichloro-3,3,3-trifluoropropene, which is characterized by that 1-halogeno-3,3,3-trifluoropropene represented by the general formula [1]: (In the formula, X represents a fluorine atom, chlorine atom or bromine atom.) is reacted with chlorine in a gas phase in the presence of a catalyst. It is possible by this process to produce 1,2-dichloro-3,3,3-trifluoropropene in an industrial scale with good yield by using 1-halogeno-3,3,3-trifluoropropene, which is available with a low price, as the raw material.Type: ApplicationFiled: April 1, 2014Publication date: December 4, 2014Applicant: CENTRAL GLASS COMPANY, LIMITEDInventors: Satoru OKAMOTO, Yoshio NISHIGUCHI, Fuyuhiko SAKYU
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Patent number: 8901360Abstract: Disclosed is a process for preparing cis-1,1,1,4,4,4-hexafluorobutene comprising the steps of (a) reacting CCl4 with a compound having the formula CF3CX?CXH, where each X is independently halogen or hydrogen, to form a compound having the formula CF3CXClCXHCCl3; (b) fluorinating the compound formed in step (a) to form a compound having the formula CF3CXHCXHCF3; (c) converting the compound formed in step (b) by a reaction selected from the group consisting of dehydrohalogenation, dehalogenation and both reactions, to form a compound having the formula CF3C?CCF3; and (d) catalytically reducing the compound formed in step (c) with hydrogen to form the compound having the formula:Type: GrantFiled: May 19, 2011Date of Patent: December 2, 2014Assignee: Honeywell International Inc.Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy
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Publication number: 20140249329Abstract: Methods of halogenating a carbon containing compound having an sp3 C—H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond are provided. The halogenated products of the methods are provided.Type: ApplicationFiled: August 20, 2012Publication date: September 4, 2014Applicant: The Trustees of Princeton UniversityInventors: John T. Groves, Wei Liu
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Patent number: 8779217Abstract: The invention relates to a method for preparing fluoropropenes of formula (I) CF3CF?CHR, where R is a hydrogen or a fluorine atom from at least one compound of formula (Ia) CF3CF?CFR, where R has the same meaning as in formula (I), said method including the following steps: (i) hydrogenating at least one compound of formula (Ia) in an adiabatic reactor in the presence of a catalyst with a superstoichiometric amount of hydrogen so as to produce a hydrofluoropropane; (ii) partially condensing the flow from the adiabatic reactor of step (i) so as to produce a gaseous phase fraction, including unreacted hydrogen and a portion of the formed hydrofluoropropane, which is recirculated to step (i), and a liquid phase fraction including the residue of the hydrofluoropropane; (iii) dehydrofluorinating hydrofluoropropane from the liquid fraction of step (ii) using potassium hydroxide in an aqueous reaction medium contained in an agitated reactor so as to produce the fluoropropene of formula (I); and (iv) purifying the flType: GrantFiled: May 21, 2010Date of Patent: July 15, 2014Assignee: Arkema FranceInventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini, Pierre-Marie Sedat, Karine Avril
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Patent number: 8766020Abstract: The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.Type: GrantFiled: July 28, 2009Date of Patent: July 1, 2014Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung, Rajiv R. Singh, Ian Shankland
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Patent number: 8742181Abstract: A process for isomerizing a (hydrohalo)fluoroalkene, the process comprising contacting the (hydrohalo)fluoroalkene with a catalyst a catalyst which is a chromia-containing catalyst supported on AlF3 or fluorinated alumina.Type: GrantFiled: November 21, 2012Date of Patent: June 3, 2014Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew Paul Sharratt, John Charles McCarthy
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Patent number: 8680345Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.Type: GrantFiled: December 7, 2011Date of Patent: March 25, 2014Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
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Patent number: 8653309Abstract: Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.Type: GrantFiled: April 20, 2011Date of Patent: February 18, 2014Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20140031595Abstract: The present invention provides continuous, gas phase, free radical processes for the production of chlorinated and/or fluorinated propenes or higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes, wherein wherein at least a portion of any intermediate boiler by-products generated by the process are removed from the processType: ApplicationFiled: October 4, 2013Publication date: January 30, 2014Applicant: DOW GLOBAL TECHNOLOGIES, LLCInventors: Max Markus Tirtowidjojo, Patrick Ho-Sing Au-Yeung, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt Frederick Hirsekorn, Manfred Kokott, William J. Kruper, JR., Thomas Ulrich Luebbe, Holger Meeman, Shirley Shaw Sexton, Peter Wenzel, Marcus Wobser
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Patent number: 8633340Abstract: The invention provides a process for preparing 1,1,1-trifluoro-2,3-dichloropropane (243db), which process comprises contacting 3,3,3-trifluoropropene (1243zf) with chlorine in the presence of a catalyst, wherein the catalyst comprises activated carbon, alumina and/or an oxide of a transition metal.Type: GrantFiled: April 9, 2009Date of Patent: January 21, 2014Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Publication number: 20140018582Abstract: The present disclosure relates to processes for reducing the concentration of RfC?CX impurities in fluoroolefins. The process involves: contacting a mixture comprising at least one fluoroolefin and at least one RfC?CX impurity with at least one amine to reduce the concentration of the at least one RfC?CX impurity in the mixture; wherein Rf is a perfluorinated alkyl group, and X is H, F, Cl, Br or I. The present disclosure also relates to processes for making at least one hydrotetrafluoropropene product selected from the group consisting of CF3CF?CH2, CF3CH?CHF, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process. The present disclosure also relates to processes for making at least one hydrochlorotrifluoropropene product selected from the group consisting of CF3CCl?CH2, CF3CH?CHCl, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process.Type: ApplicationFiled: June 6, 2013Publication date: January 16, 2014Inventors: Xuehui SUN, Mario Joseph NAPPA
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Publication number: 20140012050Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the compound of formula CF3CHFCH2X to produce 1234yf.Type: ApplicationFiled: August 19, 2013Publication date: January 9, 2014Applicant: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Publication number: 20140012049Abstract: Disclosed are processes for producing halogenated olefins, and preferably tetrafluorinated propene(s), from one or more alkanes having both fluorine substituents and non-fluorine substituents, preferably with a high degree of conversion and selectivity. Preferably the process comprises the use of a catalyzed reaction in which the catalyst is selected from the group consisting of activated carbons, halogentated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.Type: ApplicationFiled: August 16, 2013Publication date: January 9, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: HAIYOU WANG, HSUEH SUNG TUNG, SUDIP MUKHOPADHYAY
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Patent number: 8623233Abstract: Azeotropic or azeotrope-like compositions are disclosed. The azeotropic or azeotrope-like compositions are mixtures of Z-1,1,1,4,4,4-hexafluoro-2-butene, trans-1,2-dichloroethylene and 1,1,1,3,3-pentafluorobutane. Also disclosed is a process of preparing a thermoplastic or thermoset foam by using such azeotropic or azeotrope-like compositions as blowing agents. Also disclosed is a process of producing refrigeration by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as solvents. Also disclosed is a process of producing an aerosol product by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as heat transfer media. Also disclosed is a process of extinguishing or suppressing a fire by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as dielectrics.Type: GrantFiled: January 10, 2011Date of Patent: January 7, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Mark L. Robin, Joan Ellen Bartelt
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Publication number: 20140005446Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a composition containing a compound of the general formula (1): CF3—CH2—CHClX (where X is a fluorine atom or a chlorine atom) into contact with a solid catalyst in the presence of hydrogen chloride. In this production method, the composition containing ozone depleting HCFC such as 3-chloro-1,1,1,3-tetraluoforpropane or 3,3-dichloro-1,1,1-trifluoropropane can be efficiently converted to the 1-chloro-3,3,3-trifluoropropene, which has less influence on the global environment and is useful as a solvent, a cleaning agent, a coolant, a working fluid, a propellant, a raw material for fluorinated resins etc.Type: ApplicationFiled: June 27, 2013Publication date: January 2, 2014Applicant: Central Glass Company, LimitedInventors: Hideaki IMURA, Naoto TAKADA
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Patent number: 8618338Abstract: In this invention we are disclosing a process for the synthesis of hydrocchlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the gas phase, noncatalytic fluorination of hydrochlorofluoropropenes to form hydrofluoropropenes.Type: GrantFiled: November 16, 2011Date of Patent: December 31, 2013Assignee: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
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Publication number: 20130317262Abstract: To provide a method for purifying R-1234yf, whereby it is possible to efficiently remove even impurities such as R-1243zf, etc. which are difficult to separate by distillation purification, from a mixture containing R-1234yf as the main component and various impurities, such as a gas formed by reacting R-1214ya with hydrogen. The method for purifying R-1234yf comprises a step of bringing a mixture which contains R-1234yf as the main component and also contains hydrohaloalkene impurities other than R-1234yf and hydrohaloalkane impurities, into contact with a solvent that has an extraction/removal index (r), as represented by the formula r=[4×(?D?17.2)2+(?P?8.3)2+(?H?2.6)2]1/2, of at most 6.5, so as to remove at least a part of the hydrohaloalkene impurities and hydrohaloalkane impurities.Type: ApplicationFiled: August 5, 2013Publication date: November 28, 2013Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Kazuyoshi KURASHIMA, Kunio Watanabe, Hiroshi Yamamoto
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Publication number: 20130303808Abstract: Provided are methods for producing fluorinated organic compounds, which preferably comprises converting at least one compound of formula (I) CH2XCHZCF3 to at least one compound of formula (II) CHX?CZCF3 where X and Z are independently H or F, with the proviso that X and Z are not the same. The converting step comprises catalytically reacting at least one compound of formula (I), preferably via dehydrogenation or oxidative dehydrogenation. In another aspect, the inventive method of preparing fluorinated organic compounds comprises converting a reaction stream comprising at least one pentafluoropropene to a product stream comprising at least one pentafluoropropane and at least one compound of formula (I), separating out the compound of formula (I) from the product stream, and converting the compound of formula (I) separated from the product stream to at least one compound of formula (II), wherein the conversion the compound of formula (I) to 3,3,3-trifluoropropyne is substantially limited.Type: ApplicationFiled: July 17, 2013Publication date: November 14, 2013Inventors: HAIYOU WANG, HSUEH SUNG TUNG
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Publication number: 20130296617Abstract: Disclosed are the combinations containing Z and E stereoisomers of hydrofluoroolefins where the more toxic isomer is less than about 30% weight of the combination (vs the sum of Z+E), to minimize the toxicity impact in the applications they will. be used for such as cooling and heat fluids, foams blowing agents or solvents. Also disclosed are means to obtain combinations containing Z and E stereoisomers of hydrofluoroolefins.Type: ApplicationFiled: July 11, 2013Publication date: November 7, 2013Applicant: Arkema Inc.Inventors: Philippe Bonnet, Maher Y. Elsheikh
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Publication number: 20130281700Abstract: The invention relates to palladium(0)-tris{tri-[3,5-bis(trifluoromethyl)-phenyl]-phosphine} complex of formula (I), as well as to its preparation and use. This compound is outstandingly stable, and can be used as catalyst with excellent results.Type: ApplicationFiled: June 14, 2013Publication date: October 24, 2013Applicants: CHINOIN GYOGYSZER-ES VEGYESZETI TER-MEKEK GYARA ZRT, H4SEP KFTInventors: Zoltán DALICZEK, Tibor SOÓS, Zoltán FINTA, Géza Timári, Gábor Vlád
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Patent number: 8563789Abstract: In this invention we are disclosing a process for the synthesis of hydrocchlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the steps of fluorination of hydrochloropropenes or hydrochloropropanes to form hydrochlorofluoropropenes and/or hydrofluoropropenes, followed by gas phase, catalytic fluorination of the hydrochlorofluoropropenes to form hydrofluoropropenes.Type: GrantFiled: November 16, 2011Date of Patent: October 22, 2013Assignee: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
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Patent number: 8524104Abstract: Fire extinguishing compositions and methods of extinguishing a fire comprising compounds of formula (I) where Rf is a fluorocarbon group. The compounds and compositions described herein are useful as intermediates in the preparation of or as additives to AFFF (aqueous film forming foam) formulations used for the extinguishment of fuel and solvent fires.Type: GrantFiled: August 27, 2009Date of Patent: September 3, 2013Assignee: Ansul, IncorporatedInventor: Jeffrey D. Michael
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Patent number: 8524955Abstract: Disclosed is a process for making hexafluoro-2-butyne comprising the steps of: (a) providing a composition comprising CF3CX?CXCF3, where X=halogen; and (b) treating CF3CX?CXCF3 with a dehalogenation catalyst in the presence of a halogen acceptor compound Y, where Y is not hydrogen. The halogen acceptor compound Y is a material capable of being halogenated, preferably a compound having a multiple bond, such as an alkyne, alkene, allene, or carbon monoxide. Another suitable material capable of being halogenated is a cyclopropane. A catalyst effectively transfers halogen from CF3CX?CXCF3 to the halogen acceptor compound. Since Y is not hydrogen, the formation of CF3CX?CHCF3 is greatly reduced or eliminated.Type: GrantFiled: May 19, 2011Date of Patent: September 3, 2013Assignee: Honeywell International Inc.Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy, Rajiv Ratna Singh
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Publication number: 20130217928Abstract: This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl?CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.Type: ApplicationFiled: October 27, 2011Publication date: August 22, 2013Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
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Patent number: 8461401Abstract: Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides a method for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and 3,3,3-trifluoropropene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.Type: GrantFiled: March 11, 2011Date of Patent: June 11, 2013Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Haiyou Wang
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Publication number: 20130123448Abstract: A method for capturing certain fluorinated vinyl monomers from a gaseous mixture using ionic liquids is described. The gaseous mixture is contacted with at least one ionic liquid, whereby at least a portion of the fluorinated vinyl monomer is absorbed by the ionic liquid. The method is useful for reducing emissions of fluorinated vinyl monomers and for increasing the product yields in the manufacture of polymers from these monomers.Type: ApplicationFiled: May 9, 2012Publication date: May 16, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: CHARLES JOSEPH NOELKE, Mark Brandon Shiflett