Antimony Halide Containing Catalyst Patents (Class 570/167)
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Patent number: 6111150Abstract: The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes a step of adding hydrogen fluoride to 1,3,3,3-tetrafluoropropene in a liquid phase in the presence of a hydrohalogenation catalyst. This method is a useful method for producing 1,1,1,3,3-pentafluoropropane in an industrial scale, because yield of 1,1,1,3,3-pentafluoropropane is high. According to the invention, 1,3,3,3-tetrafluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst, or by another method including a step of reacting 1-chloro-3,3,3-trifluoropropene with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst.Type: GrantFiled: December 12, 1996Date of Patent: August 29, 2000Assignee: Central Glass Company, LimitedInventors: Fuyuhiko Sakyu, Yasuo Hibino, Satoshi Yoshikawa, Ryouichi Tamai, Yoshihiko Gotoh
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Patent number: 6103944Abstract: Water present in a hot gaseous product stream from a reactor system A.B (FIG. 1) containing hydrogen fluoride is separated from the stream in order to eliminate a potentially corrosive combination of water and HF. The water is removed by contacting the gaseous product stream with liquid HF in a distillation column so as to obtain a bottoms product containing liquid HF and water and a top product containing dry HF and the product to be recovered. The invention encompasses the separation process, a vessel for carrying out the process (FIGS. 2 to 4), a control system for the liquid HF supply to the distillation column (FIGS. 5 and 6) and a recovery system for recovering HF employed during operation of the reactor system in different regimes employing HF as a fluorination agent, as a diluent during catalyst regeneration and/or catalyst prefluorination (FIG. 7).Type: GrantFiled: May 2, 1994Date of Patent: August 15, 2000Assignee: Imperial Chemical Industries PLCInventors: Charles Brian Blake, James Malcolm Forsyth, Ann San Liow, Stephen John Adams, Ralph Jones Doy, Rowland John Porter Brierley, Jane Andrea Eileen Roberts, Brian Schofield, Neil David Shilling
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Patent number: 6080899Abstract: A process for producing a fluorinated organic compound comprising: (a) reacting an organic starting material with hydrogen fluoride in the presence of a fluorination catalyst and an HFC reaction solvent to produce a product stream containing the fluorinated organic compound wherein the reaction solvent has a boiling point higher than that of the fluorinated organic compound; and (b) recovering the fluorinated organic compound from the product stream.Type: GrantFiled: January 25, 1999Date of Patent: June 27, 2000Assignee: AlliedSignal Inc.Inventors: David E. Bradley, Kevin Benson, David Nalewajek, Alagappan Thenappan
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Patent number: 6075172Abstract: The present invention provides the novel chlorofluorohydrocarbon 1,1-difluoro-1,4-dichlorobutane, and a process for its preparation comprising reacting 1,1,1,4-tetrachlorobutane or 1,1,4-trichlorobut-1-ene with hydrogen fluoride in the liquid or vapor phase. The product has useful solvent properties and is also useful in synthetic chemistry for the introduction of fluorocarbon functionality.Type: GrantFiled: January 9, 1998Date of Patent: June 13, 2000Assignee: Zeneca LimitedInventors: Alfred Glyn Williams, Martin Charles Bowden, Stephen Martin Brown
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Patent number: 6074985Abstract: A supported Lewis acid catalyst such as antimony V on a fluorine-treated moisture-free activated carbon support is provided, as are fluorination processes using such a catalyst.Type: GrantFiled: August 3, 1999Date of Patent: June 13, 2000Assignee: Elf Atochem North America, Inc.Inventors: Maher Y. Elsheikh, Bin Chen
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Patent number: 6066769Abstract: A process is disclosed for producing a compound of the formula: CF.sub.3 CHXCF.sub.3-z Y.sub.2 where X and Y are independently selected from the group consisting of H and Cl, and z is 0 or 1. The process involves (1) contacting CCl.sub.3 CHXCC.sub.3-z Y.sub.z,CCl.sub.2-z .dbd.CXCC.sub.3, and/or CCl.sub.2 CX.dbd.CC.sub.3-z Y.sub.z starting material, with hydrogen fluoride at a temperature of less than 200.degree. C. to produce a fluorination product of said starting material which includes at least 90 mole percent total of C.sub.3 HXY.sub.z Cl.sub.6-z-x F.sub.x saturated compounds and C.sub.3 XY.sub.z Cl.sub.5-z-y F.sub.y olefinic compounds, wherein x is an integer from 1 to 6-z and y is an integer from 1 to 5-z, (the fluorination product including no more than about 40 mole percent of the desired product, CF.sub.3 CHXCF.sub.3-z Y.sub.z); (2) contacting saturated compounds and olefinic compounds produced in (1) with hydrogen fluoride in the vapor phase at a temperature of from 200.degree. C. to about 400.Type: GrantFiled: October 6, 1998Date of Patent: May 23, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Allen Capron Sievert, Edwin J. Warwas
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Patent number: 6063969Abstract: A process for the preparation of 142 is provided, wherein 1130 is fluorinated in the gas phase in the presence of a catalyst which is a supported or unsupported fluorinated salt of one or more of chromium, iron, niobium, nickel, antimony, tin, tantalum or titanium. 142 is a known foam blowing agent.Type: GrantFiled: December 8, 1998Date of Patent: May 16, 2000Assignee: Elf Atochem North America, Inc.Inventors: Michael S. Bolmer, Bin Chen
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Patent number: 6049016Abstract: There is provided a process for producing HFC-125 and/or HCFC-124 from PCE, characterized by the first reaction step of fluorinating PCE in the presence of catalyst in a liquid phase to form HCFC-123 and/or HCFC-122 and the second reaction step of fluorinating HCFC-123 and/or HCFC-122 in the presence of catalyst in a vapor phase to form HFC-125 and/or HCFC-124.This process is improved in the yield of objective products, and life of catalyst, and the controllability of reaction temperature.Type: GrantFiled: July 26, 1999Date of Patent: April 11, 2000Assignee: Daikin Industries Ltd.Inventors: Toshikazu Yoshimura, Yukio Homoto, Yasufu Yamada, Takehide Tsuda, Takashi Shibanuma
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Patent number: 6018084Abstract: A manufacturing method for 1,1,1,3,3-pentafluoropropane comprises a first process, in which 1,1,1-trifluoro-3-chloro-2-propene is obtained by inducing a reaction between 1,1,1,3,3-pentafluoropropane and hydrogen fluoride in the vapor phase, and a second process, in which the 1,1,1,3,3-pentafluoropropane is obtained by inducing a reaction between 1,1,1-trifluoro-3-chloro-2-propene and hydrogen in the vapor phase, and 1,1,1-trifluoro-3-chloro-2-propene obtained in the first process is supplied to the second process after removing the HCl by-products. This invention can provide a new economic manufacturing method of 1,1,1,3,3-pentafluoropropane with high yield and selectivity.Type: GrantFiled: June 25, 1998Date of Patent: January 25, 2000Assignee: Daikin Industries Ltd.Inventors: Tatsuo Nakada, Hirokazu Aoyama, Akinori Yamamoto
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Patent number: 6013846Abstract: An azeotrope containing HF and 1233zd is provided, as are methods for separating this azeotrope from mixtures of HF and 1233zd which are HF-rich or 1233zd-rich and methods for making use of the azeotrope and separation methods to improve processes for preparing 1233zd, an intermediate used in the preparation of 245fa. 245fa is a known foam blowing agent and refrigerant.Type: GrantFiled: March 5, 1998Date of Patent: January 11, 2000Assignee: Elf Atochem North America, Inc.Inventors: John A. Wismer, Michael S. Bolmer, Bin Chen
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Patent number: 6011185Abstract: There is provided a process for producing HFC-125 and/or HCFC-124 from PCE, characterized by the first reaction step of fluorinating PCE in the presence of catalyst in a liquid phase to form HCFC-123 and/or HCFC-122 and the second reaction step of fluorinating HCFC-123 and/or HCFC-122 in the presence of catalyst in a vapor phase to form HFC-125 and/or HCFC-124.This process is improved in the yield of objective products, and life of catalyst, and the controllability of reaction temperature.Type: GrantFiled: August 20, 1997Date of Patent: January 4, 2000Assignee: Daikin Industries Ltd.Inventors: Toshikazu Yoshimura, Yukio Homoto, Yasufu Yamada, Takehide Tsuda, Takashi Shibanuma
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Patent number: 5981814Abstract: A process is disclosed for the preparation of a fluorinated aliphatic hydrocarbon having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-bwherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3. The reaction occurs in the vapor phase. A chlorofluoro olefin of the formulaCH.sub.c Cl.sub.2-c .dbd.CH--CH.sub.d F.sub.3--dwherein c is 0 or the integer 1 or 2, and d is 0 or the integer 1 or 2 is treated in the vapor phase with hydrogen fluoride. This treating is catalyzed with a compound that is a metal oxide, a metal halide or a mixture thereof. The metallic part of such compound is selected from a metal in Group IIIa, IIIb, IVa, Va, IVb, Vb, VIa, VIb, VIIb and VIII of the Periodic Table of the Elements. The treating is carried out for a time sufficient to form the desired fluorinated aliphatic hydrocarbon which is subsequently recovered from the vapor phase reaction.The process is particularly suitable for the preparation of 1,1,1,3,3-pentafluoropropane.Type: GrantFiled: March 23, 1998Date of Patent: November 9, 1999Assignee: LaRoche Industries Inc.Inventors: C. Bradford Boyce, Randolph K. Belter
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Patent number: 5969198Abstract: A process for preparing 1,1,1,3,3-pentafluoropropane from a hydrochlorocarbon of the formula C.sub.3 H.sub.y Cl.sub.x, wherein x is an integer from 3 to 5, y is an integer from 1 to 3, x+y=4, 6, or 8, and x-y=2 is provided.Type: GrantFiled: June 27, 1997Date of Patent: October 19, 1999Assignee: AlliedSignal Inc.Inventors: Alagappan Thenappan, Michael Van Der Puy, Hsueh S. Tung
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Patent number: 5910616Abstract: A process is disclosed for the preparation of a fluorinated aliphatic hydrocarbon. The process utilizes a C.sub.1 to C.sub.6 hydrocarbon substituted with a halogen selected from the group consisting of chlorine, bromine and iodine as the starting material. The alkyl hydrocarbon is reacted in the vapor phase at a temperature from about 75.degree. to about 150.degree. C. with hydrogen fluoride and a catalytically effective amount of at least one antimony compound having the formulaSb.sub.w.sup.u M.sub.x.sup.v X.sub.y F.sub.z.nHFwhere n is 0 or an integer that is at least 1; M is selected from the group consisting of a metal from Group IIIa, IIIb, IVa, IVb, Va, Vb, VIa, VIb, VIIb and VIII of the Periodic Table of the Elements; X is chloro, bromo or iodo; u is an integer that is the valence of antimony; v is an integer that is the valence of M; w, x and z are an integer of at least 1; y is 0 or an integer of at least 1; and (w.multidot.u)+(x.multidot.Type: GrantFiled: June 22, 1998Date of Patent: June 8, 1999Assignee: LaRoche Industries, Inc.Inventors: C. Bradford Boyce, Randolph K. Belter
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Patent number: 5902912Abstract: A process for producing a hydrofluorocarbon (HFC) comprising (a) providing a fluoropolymer-lined reactor; (b) adding a chlorinated organic compound in liquid phase and a fluorination agent to the reactor; and (c) reacting at least a portion of the chlorinated organic compound with at least a portion of the fluorination agent to produce the HFC.Type: GrantFiled: June 26, 1997Date of Patent: May 11, 1999Assignee: AlliedSignal Inc.Inventors: Hsueh Sung Tung, Daniel Christopher Merkel, Addison Miles Smith
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Patent number: 5902913Abstract: A process for the co-production of two or more hydrofluoroalkanes which comprises contacting an alkene or a halogenated alkane with hydrogen fluoride at elevated temperature in the presence of a fluorination catalyst to produce a first hydrofluoroalkane and wherein an organic precursor to a second hydrofluoroalkane is provided in the process whereby to produce a second hydrofluoroalkane in addition to the first hydrofluoroalkane. In particularly preferred embodiments of the process, the first hydrofluoroalkane is 1,1,1,2-tetrafluoroethane derived from 1-chloro-2,2,2-trifluoroethane or trichloroethylene and the second hydrofluoroalkane is one or more of pentafluoroethane, difluoromethane and 1,1,2,2-tetrafluoroethane.Type: GrantFiled: February 6, 1997Date of Patent: May 11, 1999Assignee: Imperial Chemical Industries PLCInventors: Richard Llewellyn Powell, John David Scott, Charles John Shields, David William Bonniface
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Patent number: 5895825Abstract: A process for the preparation of 245fa is provided, wherein 1233zd is first fluorinated to 1234ze, followed by fluorination of 1234ze to 245fa. 245fa is a known foam blowing agent and refrigerant.Type: GrantFiled: December 1, 1997Date of Patent: April 20, 1999Assignee: Elf Atochem North America, Inc.Inventors: Maher Y. Elsheikh, Michael S. Bolmer, Bin Chen
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Patent number: 5880317Abstract: The present invention relates to a process for the reduction dechlorination of ClCF.sub.2 CFClCF.sub.2 Cl to HCF.sub.2 CHFCF.sub.2 H comprising the step of contacting 1,2,3-trichloropentafluoroethane and H.sub.2 over a catalyst selected from the group consisting of palladium, platinum, ruthinium, rhodium, iridium and mixtures thereof under reaction conditions sufficent to produce a product stream containing 1,1,2,3,3-pentafluoropropane. The present invention further relates to a three step process wherein the ClCF.sub.2 CFClCF.sub.2 Cl to be reduced is synthesized by:(a) reacting HF with a compound of formula I: XCH.dbd.CYCH.sub.2 X, where X is H, Cl, or F, Y is H or Cl;to give a compound of formula II: CH.sub.2 XCFYCH.sub.2 X, where X and Y are the same as in the compound of formula I:(b) chlorinating the compound of formula II to give a compound of formula III: CCl.sub.3-m F.sub.m CFClCCl.sub.3-m F.sub.m where m is zero or 1, and(c) fluorinating the compound of formula III to give CClF.sub.2 CFClCF.sub.Type: GrantFiled: September 30, 1993Date of Patent: March 9, 1999Assignee: AlliedSignal Inc.Inventor: M. Van Der Puy
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Patent number: 5847244Abstract: A production method in which reaction processes are divided into two regions comprising one reaction region where mainly perohloroethylene is made to react with HF in a vapor phase in the presence of a catalyst and the other reaction region where HCFC-123 (CF.sub.3 CHCl.sub.2) and/or HCFC-124 (CF.sub.3 CFHCl) is made to react with HF in a vapor phase in the presence of a catalyst, the former region being kept at a higher pressure and the latter region at a lower pressure during the reaction procedure. By this method it is possible to keep the conversion of perchloroethylene at a high level while securing the life of a catalyst, and it is also possible to raise the selectivity of HFC-125. This is a method of producing HFC-125 in which the content of CFC-115 is lowered to not more than 15 vol % of the total amount of HFC-125 and CFC-115, and then CFC-115 is made to react with hydrogen in the presence of a catalyst.Type: GrantFiled: February 13, 1998Date of Patent: December 8, 1998Assignee: Daikin Industries, Ltd.Inventors: Takashi Shibanuma, Yukio Homoto, Satoshi Komatsu, Toshikazu Yoshimura
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Patent number: 5841007Abstract: The present invention relates to a process for manufacturing 1,1,1,2-tetrafluoroethane (HFC-134a) from trichloroethylene (TCE) and hydrogen fluoride (HF) by reacting the HCFC-133a with the HF to produce the HFC-134a and reacting the TCE with the HF to produce 1-choro-2,2,2-trifluoroethane (HCFC-133a), characterized by that a part of said HF is mixed with the mixture containing the HFC-134a and the remaining portion of said HF is fed with said TCE in portions to at least two sections of a reactor for producing said HCFC-133a. According the present process, the temperature change in the reactor for producing HCFC-133a is maintained within a narrow range over the whole reaction procedures, and the catalytic activity is well maintained. Further, the formation of by-products is considerably prevented and thus the productivity is remarkably enhanced.Type: GrantFiled: April 12, 1996Date of Patent: November 24, 1998Assignee: Korea Institute of Science and TechnologyInventors: Byoung Sung Ahn, Young Soo Kwon, Kun You Park, Moon Jo Chung
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Patent number: 5817894Abstract: Difluoromethane is produced from dichloromethane and hydrogen fluoride by continuous reaction in a liquid medium comprising an inorganic fraction and an organic fraction, in which a content by weight of the said organic fraction in the liquid medium is maintained at less than or equal to 25% of the sum of the inorganic and organic fractions and a content by weight of dichloromethane in the liquid medium is maintained at less than or equal to 10% of the sum of the inorganic and organic fractions.Type: GrantFiled: September 3, 1997Date of Patent: October 6, 1998Assignee: Solvay (Societe Anonyme)Inventors: Vincent Wilmet, Francine Janssens
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Patent number: 5811604Abstract: A process for the continuous production of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa) and/or 1-chloro-1,1,3,3,3-pentafluoropropane (HCFC-235fa) in the liquid phase wherein the HFC-235fa and/or HFC-236fa serve as solvents for the reaction. When the reaction is conducted in the presence of a catalyst of SbF.sub.3, SbF.sub.5 or a mixture of SbF.sub.5 and HSO.sub.3 F, the reaction mass is unexpectedly less corrosive to the reaction vessel used.Type: GrantFiled: February 5, 1997Date of Patent: September 22, 1998Assignee: AlliedSignal, Inc.Inventors: Kevin Robert Benson, David Elliott Bradley, David Nalewajek
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Patent number: 5763706Abstract: An integrated manufacturing process for producing HFC-245fa, HFC-236fa or a mixture thereof by reaction of HCC-240fa, HCC-230 or a mixture thereof with HF. HCC-240fa, HCC-230 or a mixture thereof is reacted with hydrogen fluoride in a liquid phase in the presence of a fluorination catalyst. Optionally, produced HCl is removed by distillation. HF present is thereafter recovered by liquid-vapor extraction. Unsaturated compounds are then removed by photochlorination and HFC-245fa, HFC-236fa or a mixture thereof is obtained by distillation.Type: GrantFiled: July 3, 1996Date of Patent: June 9, 1998Assignee: AlliedSignal Inc.Inventors: Hsueh Sung Tung, Daniel Chistopher Merkel, Zenart Joseph Dziadyk, Clayton Herbert Carson, Hang Thanh Pham
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Patent number: 5763707Abstract: There is provided a process for the production of pentafluoroethane which comprises contacting a hydrofluorochloroethane having the formula: C.sub.2 H.sub.1 Cl.sub.1+x F.sub.1+y wherein x and y are each independently 0,1,2 or 3 provided x+y is 3 with hydrogen fluoride in the vapor phase and in the presence of a fluorination catalyst which comprises zinc or a compound of zinc and chromia, chromium fluoride or chromium oxyfluoride.Type: GrantFiled: September 19, 1996Date of Patent: June 9, 1998Assignee: Imperial Chemical Industries PLCInventors: John David Scott, Michael John Watson, Paul Nicholas Ewing
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Patent number: 5763705Abstract: There are provided production methods of 1,1,1,3,3-pentafluoropropane characterized in that 1,1,1,3,3-pentafluoro-2,3-dichloropropane is reacted with hydrogen fluoride in the presence of a noble metal catalyst; of 1,1,1,3,3-pentafluoro-2-halogeno-3-chloropropane characterized in that the halogenated propene indicated as general formula I is fluorinated in the presence of antimony trihalogenide and/or antimony pentahalogenide by hydrogen fluoride of mole ratio of or over five times the said antimony halogenide in a liquid phase; and of 1,1,1,2,3,3-hexachloropropene characterized in that 1,1,1,2,2,3,3-heptachloropropane is reacted with an aqueous solution of alkali metal hydroxide in the presence of a phase transfer catalyst. Therefore, an industrial manufacturing method which is possible to obtain the objective product easily at low cost and high yield can be provided.Type: GrantFiled: March 10, 1997Date of Patent: June 9, 1998Assignee: Daikin Industries Ltd.Inventors: Seiji Takubo, Hirokazu Aoyama, Tatsuo Nakada
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Patent number: 5750809Abstract: A production method in which reaction processes are divided into two regions comprising one reaction region where mainly perchloroethylene is made to react with HF in a vapor phase in the presence of a catalyst and the other reaction region where HCFC-123 (CF.sub.3 CHCl.sub.2) and/or HCFC-124 (CF.sub.3 CFHCl) is made to react with HF in a vapor phase in the presence of a catalyst, the former region being kept at a higher pressure and the latter region at a lower pressure during the reaction procedure. By this method it is possible to keep the conversion of perchloroethylene at a high level while securing the life of a catalyst, and it is also possible to raise the selectivity of HFC-125. This is a method of producing HFC-125 in which the content of CFC-115 is lowered to not more than 15 vol % of the total amount of HFC-125 and CFC-115, and then CFC-115 is made to react with hydrogen in the presence of a catalyst.Type: GrantFiled: September 5, 1995Date of Patent: May 12, 1998Assignee: Daikin Industries Ltd.Inventors: Takashi Shibanuma, Yukio Homoto, Satoshi Komatsu, Toshikazu Yoshimura
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Patent number: 5744660Abstract: This invention relates to a process for the production of 1,1,2,2- and/or 1,1,1,2-tetrafluoroethanes, and in particular to a process for the production of 1,1,1,2-tetrafluoroethane.Type: GrantFiled: December 21, 1995Date of Patent: April 28, 1998Assignee: Imperial Chemical Industries PLCInventors: Lisa Bradley, Leslie Burgess, Richard Llewellwyn Powell, Geoffrey James Moore, Paul Nicholas Ewing, Kenneth Taylor
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Patent number: 5744658Abstract: A method of producing 1,1,1,2-tetrafluoroethane in two separation reaction zones involving (1) reaction of trichloroethylene and hydrogen fluoride to produce l,l,l-trifluoro-2-chloroethane and (2) reaction of the 1,1,1-trifluoro-2-chloroethane and hydrogen fluoride to produce 1,1,1,2-tetrafluoroethane wherein both reactions are carried out at superatmospheric pressure, reaction (2) is carried out at a temperature in the range of 250.degree.-450.degree. C., reaction (1) is carried out at a temperature in the range of 200.degree.-400.degree. C. but below that used in reaction (2) and unconverted 1,1,1-trifluoro-2-chloroethane is recycled for further reaction with hydrogen fluoride.Type: GrantFiled: July 18, 1996Date of Patent: April 28, 1998Assignee: Imperial Chemical Industries PLCInventors: John David Scott, Rachel Anne Steven
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Patent number: 5744659Abstract: Difluoromethane is prepared by reacting dichloromethane and hydrogen fluoride in a liquid phase in the presence of a fluorination catalyst under reaction conditions in which the reaction pressure is between 1 and 10 kg/cm.sup.2 ab., and the reaction temperature is between 50 and 150.degree. C., provided that the selected reaction temperature is higher than a temperature at which hydrogen fluoride is not liquefied under the selected reaction pressure.Under the above conditions, the conversions of dichloromethane and HF are very high, and amounts of by-products other than R30 are very low, typically less than 0.1% per difluoromethane, when the unreacted materials are recycled.A material of a reactor is hardly corroded by the reaction using an antimony chlorofluoride and HF which are highly corrosive, as long as the above conditions are maintained.Type: GrantFiled: December 19, 1996Date of Patent: April 28, 1998Assignee: Daikin Industries, Ltd.Inventors: Takehide Tsuda, Yasufu Yamada, Takashi Shibanuma
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Patent number: 5739406Abstract: Process for the hydrofluorination of chloro(fluoro)butane of general formula C.sub.4 H.sub.5 Cl.sub.x F.sub.5-x in which x=1 to 5, by means of hydrogen fluoride and in the presence of a catalyst chosen from the derivatives of metals of groups IIIa, IVa, IVb, Va, Vb and VIb of the Periodic Table of the elements.Type: GrantFiled: August 30, 1995Date of Patent: April 14, 1998Assignee: Solvay (Societe Anonyme)Inventors: Pascal Pennetreau, Francine Janssens
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Patent number: 5714650Abstract: A process is disclosed for producing 1,1-difluoroethane (HFC-152a) in a liquid phase by contacting chloroethene and hydrogen fluoride in the presence of a tin tetrahalide catalyst. The ability to reduce tar formation and increase volumetric productivity is also disclosed.Type: GrantFiled: June 7, 1995Date of Patent: February 3, 1998Assignee: E. I. Du Pont de Nemours and CompanyInventor: Klaus Guenter Wuttke
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Patent number: 5714652Abstract: The invention relates to a process for the preparation of 1,1-difluoroethane by reaction of vinyl chloride with hydrogen fluoride, in the presence of perchloroethylene or 1,1,1,3,3-pentafluorobutane.Type: GrantFiled: April 11, 1996Date of Patent: February 3, 1998Assignee: Solvay (Societe Anonyme)Inventors: Frans Grunchard, Francine Janssens, Vincent Wilmet
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Patent number: 5710352Abstract: A method for the preparation of 1,1,1,3,3-pentafluoropropane (HFC-245fa) and 1-chloro-3,3,3-trifluoropropene (HCFC-1233). 1,1,1,3,3-pentachloropropane (HCC-240fa) is fluorinated with HF in a vapor phase in the presence of a vapor phase catalyst. The HCFC-1233 and any co-produced 1,3,3,3-tetrafluoropropene (HFC-1234) are recycled for further fluorination by HF for a greater than 99% HCC-240fa conversion.Type: GrantFiled: September 19, 1996Date of Patent: January 20, 1998Assignee: AlliedSignal Inc.Inventor: Hsueh Sung Tung
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Patent number: 5705717Abstract: Fluorination processes using hydrogen fluoride-containing fluorinating agents that are safely and easily handled, transported, and stored and that also exhibit good reactivity are provided. More particularly, the invention provides processes for producing fluorinated products using fluorinating agents comprising hydrogen fluoride and a carrier that may be an acid salt or a water-soluble polymer.Type: GrantFiled: March 7, 1996Date of Patent: January 6, 1998Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, Jeffrey Warren Mckown, Hang Thanh Pham, Andrew Joseph Poss, Rajiv Ratna Singh
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Patent number: 5689019Abstract: A manufacturing method for 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ea) wherein 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ea) is obtained by reacting hexafluoropropene (HFP) with anhydrous hydrogen fluoride (HF) under the presence of antimony catalyst.A manufacturing method can be provided in which HFC-227ea can be obtained at high yield under the mild condition without producing by-products such as olefin compounds and so on.Type: GrantFiled: January 14, 1997Date of Patent: November 18, 1997Assignee: Daikin Industries Ltd.Inventors: Hirokazu Aoyama, Noriaki Shibata
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Patent number: 5672786Abstract: A process for the production of difluoromethane comprising (a) contacting dichloromethane with hydrogen fluoride in the presence of a fluorination catalyst to produce a product stream comprising difluoromethane, monochloromonofluoromethane and unreacted starting materials and (b) separating difluoromethane from the product stream from step (a), wherein sufficient hydrogen fluoride is employed in the process such that during step (b) the molar ratio of hydrogen fluoride to monochloromonofluoromethane is at least about 100:1.Type: GrantFiled: September 6, 1995Date of Patent: September 30, 1997Assignee: Imperial Chemical Industries PLCInventors: David William Bonniface, John David Scott, Michael John Watson
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Patent number: 5672785Abstract: A process for producing 1,1-dichloro-1,2,2,2-tetrafluoroethane, which comprises isomerizing 1,1,2-trichloro-1,2,2-trifluoroethane to form 1,1,1-trichloro-2,2,2-trifluoroethane, followed by fluorination with hydrofluoric acid.Type: GrantFiled: February 17, 1995Date of Patent: September 30, 1997Assignee: Asahi Glass Company Ltd.Inventors: Shinsuke Morikawa, Shunichi Samejima, Masaru Yoshitake, Shin Tatematsu
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Patent number: 5659093Abstract: There are provided production methods of 1,1,1,3,3-pentafluoropropane characterized in that 1,1,1,3,3-pentafluoro-2,3-dichloropropane is reacted with hydrogen fluoride in the presence of a noble metal catalyst; of 1,1,1,3,3-pentafluoro-2-halogeno-3-chloropropane characterized in that the halogenated propene indicated as general formula I is fluorinated in the presence of antimony trihalogenide and/or antimony pentahalogenide by hydrogen fluoride of mole ratio of or over five times the said antimony halogenide in a liquid phase; and of 1,1,1,2,3,3-hexaohloropropene characterized in that 1,1,1,2,2,3,3-heptachloropropane is reacted with an aqueous solution of alkali metal hydroxide in the presence of a phase transfer catalyst. Therefore, an industrial manufacturing method which is possible to obtain the objective product easily at low cost and high yield can be provided.Type: GrantFiled: June 27, 1995Date of Patent: August 19, 1997Assignee: Daikin Industries Ltd.Inventors: Seiji Takubo, Hirokazu Aoyama, Tatsuo Nakada
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Patent number: 5616819Abstract: A process is disclosed for the preparation of a fluorinated aliphatic olefin having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-bwherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3.In the first step of the process, a chlorinated olefinic hydrocarbon of the formulaCH.sub.c Cl.sub.2-c .dbd.CH--CH.sub.d Cl.sub.3-dwherein c is 0 or the integer 1 and d is 0 or the integer 1 or 2 is reacted with anhydrous hydrogen fluoride for a period of time and at a temperature sufficient to form a chlorofluoro olefin of the formulaCH.sub.e Cl.sub.2-e .dbd.CH--CH.sub.f F.sub.3-fwherein e is 0 or the integer 1 and f is 0 or the integer 1 or 2.The chlorofluoro olefin produced in the first step is then reacted with anhydrous hydrogen fluoride in a second reaction. This second reaction is catalyzed with at least one compound that is a metal oxide or metal halide. Mixtures of said metal oxides, metal halides and metal oxides with metal halides may also be used.Type: GrantFiled: August 28, 1995Date of Patent: April 1, 1997Assignee: LaRoche Industries Inc.Inventors: C. Bradford Boyce, Randolph K. Belter
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Patent number: 5608126Abstract: A process for preparing 1,1,1,3,3-pentafluoropropane, which comprises reacting 1,1-difluoroethylene with dichlorofluoromethane in the presence of a Lewis acid catalyst to form 1,2,2-trihydrodichlorotrifluoropropane and fluorinating the 1,2,2-trihydrodichlorotrifluoropropane with hydrogen fluoride.Type: GrantFiled: June 23, 1995Date of Patent: March 4, 1997Assignee: AG Technology Co., Ltd.Inventors: Shinsuke Morikawa, Hidekazu Okamoto, Keiichi Ohnishi, Shin Tatematsu
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Patent number: 5574192Abstract: This invention is related to the preparation of hydrofluorocarbons (HFCs). Specifically, it relates to the fluorination of a compound of the formula:CF.sub.y Cl.sub.3-y CH.sub.2 CHF.sub.w Cl.sub.2-wwherein w=0 or 1, and y=0-3, with hydrogen fluoride in the presence of a fluorination catalyst under conditions sufficient to produce a compound of the formula CF.sub.3 CH.sub.2 CF.sub.2 H.CF.sub.3 CH.sub.2 CF.sub.2 H or HFC 245fa may be used as a blowing agent, a propellant, and a heat transfer agent.Type: GrantFiled: August 25, 1995Date of Patent: November 12, 1996Assignee: AlliedSignal Inc.Inventors: Michael VanDerPuy, Alagappan Thenappan
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Patent number: 5574191Abstract: 1,1,1-Trifluoroethane is produced, in addition to 1,1,-dichloro-1-fluoroethane and/or 1-chloro-1,1-difluoroethane, by hydrofluorination in the liquid phase, using hydrogen fluoride, vinylidene fluoride and at least one chloro compound chosen from vinylidene chloride and 1,1,1-trichloroethane.Type: GrantFiled: September 25, 1995Date of Patent: November 12, 1996Assignee: Solvay (Soci et e Anonyme)Inventors: Dominique Balthasart, Pascal Pennetreau
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Patent number: 5569793Abstract: The invention relates to continuous production of 1,1,1-chlorodifluoroethane from 1,1,1-trichloroethane and hydrofluoric acid by reaction in liquid phase in the presence of at least one fluorination catalyst. According to the invention, the process is carried out under an absolute pressure of between 6 and 30 bars and at a temperature of between 50.degree. and 120.degree. C., the content of catalyst(s) in the reaction mixture, expressed as a percentage by weight of metal, being between 0.05 and 10% and the content of organohalogenated by-products not belonging to series 140 in the reaction mixture being controlled at a value below 40% by weight. This process makes it possible, at the same time, to obtain a high degree of conversion of hydrofluoric acid, to minimize the coproduction of 1,1,1-trifluoroethane and organohalogenated by-products and to facilitate the recovery of the hydrochloric acid formed.Type: GrantFiled: June 7, 1995Date of Patent: October 29, 1996Assignee: Societe AtochemInventors: Michel Bergougnan, Jean-Michel Galland, Sylvain Perdrieux
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Patent number: 5559276Abstract: A method of producing 1,1,1,2-tetrafluoroethane in two separation reaction zones involving (1) reaction of trichloroethylene and hydrogen fluoride to produce 1,1,1-trifluoro-2-chloroethane and (2) reaction of the 1,1,1- trifluoro-2-chloroethane and hydrogen fluoride to produce 1,1,1,2-tetrafluoroethane wherein both reactions are carried out at superatmospheric pressure, reaction (2) is carried out at a temperature in the range of 250.degree.-450.degree. C., reaction (1) is carried out at a temperature in the range of 200.degree.-400.degree. C. but below that used in reaction (2) and unconverted 1,1,1-trifluoro-2-chloroethane is recycled for further reaction with hydrogen fluoride.Type: GrantFiled: September 15, 1994Date of Patent: September 24, 1996Assignee: Imperial Chemical Industries PLCInventors: John D. Scott, Rachel A. Steven
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Patent number: 5545778Abstract: A process for the preparation of one or more of CHClFCF.sub.3 (HCFC-124), CHF.sub.2 CClF.sub.2 (HCFC-124a) and CHF.sub.2 CF.sub.3 (HFC-125) by reaction of perchloroethylene with hydrogen fluoride in a single stage reaction vessel in the presence of a fluorination catalyst. These compounds are useful in a variety of industrial applications including blowing agents, refrigerants, sterilant gases and solvent applications. Distilling the reaction product produces a distillate comprising HCl, CHClFCF.sub.3, CHF.sub.2 CClF.sub.2 and CHF.sub.2 CF.sub.3 and a minor amount of HF which distillate is scrubbed to remove the acids. The bottoms product comprises perchloroethylene, hydrogen fluoride and organic by-products which is phase separated to sequester the hydrogen fluoride from the mixture of perchloroethylene and organic by-products. The hydrogen fluoride and mixture of perchloroethylene with organic by-products are then preferably re-mixed at a controlled rate and recycled to the reaction vessel.Type: GrantFiled: May 25, 1994Date of Patent: August 13, 1996Assignee: AlliedSignal Inc.Inventors: Hsueh S. Tung, Addison M. Smith, Charles F. Swain
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Patent number: 5545775Abstract: 1,1-difluoroethane is produced by the reaction of 1,2-dichloroethane with anhydrous hydrogen fluoride in a liquid phase and in the presence of a Lewis acid. Preferably the Lewis acid is tin, antimony, titanium, molybdenum, tungsten, niobium or tantalum halide or a mixture thereof.Type: GrantFiled: August 25, 1995Date of Patent: August 13, 1996Assignee: AlliedSignal Inc.Inventors: Alagappan Thenappan, Charles F. Swain, Matthew H. Luly
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Patent number: 5545773Abstract: In an improved process and plant for carrying out liquid phase fluorination in the presence of a catalyst, consisting in reacting hydrofluoric acid and an organic starting material in a reaction zone, and in separating, in a separating zone, reactional mixture and at least one light fraction containing the desired fluorinated organic products and at least a first part of the sub-fluorinated organic products formed, and a heavy fraction that includes the remainder of the sub-fluorinated organic products formed, and further comprising partial condensation of the said light fraction in order to obtain a gaseous phase containing the desired fluorinated organic products and a liquid phase containing said first part of the said sub-fluorinated organic products, said heavy fraction being returned to said reaction zone and said liquid phase being returned as a reflux to the top of the separation zone, intermediate recovery is carried out at, or in the proximity of, the lower portion of said separation zone.Type: GrantFiled: July 25, 1994Date of Patent: August 13, 1996Assignee: Elf Atochem S.A.Inventor: Bernard Berthe
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Patent number: 5545770Abstract: A process is disclosed for producing a product comprising CCl.sub.2 FCF.sub.3 substantially free of CClF.sub.2 CClF.sub.2. The process includes (i) contacting a mixture of perhalogenated hydrocarbons which is essentially free of CClF.sub.2 CClF.sub.2 and comprises from 20 to 80 mole percent CCl.sub.3 CF.sub.3 and from 5 to 80 mole percent total of at least one compound selected from the group consisting of CCl.sub.2 .dbd.CCl.sub.2, CCl.sub.3 CCl.sub.2 F, CCl.sub.2 FCCl.sub.2 F and CClF.sub.2 CCl.sub.3 with HF and optionally Cl.sub.2 (provided that when the mixture comprises CCl.sub.2 .dbd.CCl.sub.2, Cl.sub.2 is supplied in a mole ratio of Cl.sub.2 to CCl.sub.2 .dbd.CCl.sub.2 of at least 1:2) over a fluorination catalyst at an elevated temperature no higher than 375.degree. C., to provide a product mixture comprising CCl.sub.2 FCClF.sub.2 and C.sub.2 Cl.sub.2 F.sub.4 wherein the ratio of CClF.sub.2 CClF.sub.2 to CCl.sub.2 FCF.sub.3 is less than about 1:50; (ii) recovering said C.sub.2 Cl.sub.2 F.sub.Type: GrantFiled: May 8, 1995Date of Patent: August 13, 1996Assignee: E.I. Du Pont de Nemours and CompanyInventor: V. N. Mallikarjuna Rao
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Processes for the preparation of fluorinated olefins and hydrofluorocarbons using fluorinated olefin
Patent number: 5532419Abstract: The invention relates to a cost effective and convenient process for the manufacture of fluorinated olefins of the formula RCF.sub.2 CH.dbd.CH.sub.2 where R is C.sub.x Cl.sub.y F.sub.z and y+z=2x+1. The invention is also directed to a practical process for converting these olefins to hydrofluorocarbons via the catalyzed fluorination with hydrogen fluoride. Hydrofluorocarbons produced via this process have application as solvents among other uses.Type: GrantFiled: September 15, 1995Date of Patent: July 2, 1996Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung -
Patent number: 5495057Abstract: There is disclosed a method for the preparation of difluoromethane wherein methylene chloride is reacted with. hydrogen fluoride in liquid phase, at a temperature of about 70.degree. to 90.degree. C. under a pressure of about 11 to 12 kg/cm.sup.2.g in the presence of antimony pentachloride. It is important that the concentration of quinquevalent antimony is maintained at a level of 85% or more with the feed mole ratio of hydrogen fluoride to methylene chloride ranging from about 2.0 to 2.3.Applicable to industrial scale, the method is operated in a batch system or in a continuous system. In addition, it exhibits superior conversion rate of the materials and production yield.Type: GrantFiled: March 2, 1995Date of Patent: February 27, 1996Assignee: Ulsan Chemical Co., Ltd.Inventors: Kyung H. Nam, Doo C. Na, Dae S. Kim