Antimony Halide Containing Catalyst Patents (Class 570/167)
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Patent number: 11572326Abstract: A method hydrofluorinates an olefin of the formula: RCX=CYZ to produce a hydrofluoroalkane of formula RCXFCHYZ or RCXHCFYZ, where 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. The method includes reacting the olefin with HF in the vapor 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: April 1, 2021Date of Patent: February 7, 2023Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Xuehui Sun, Mario Joseph Nappa, Karl Krause
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Patent number: 10988422Abstract: 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: April 13, 2020Date of Patent: April 27, 2021Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Xuehui Sun, Mario Joseph Nappa, Karl Krause
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Patent number: 10711343Abstract: A novel method, composition and storage and delivery container for using antimony-containing dopant materials are provided. The composition is selected with sufficient vapor pressure to flow at a steady, sufficient and sustained flow rate into an arc chamber as part of an ion implant process. The antimony-containing material is represented by a non-carbon containing chemical formula, thereby reducing or eliminating the introduction of carbon-based deposits into the ion chamber. The composition is stored in a storage and delivery vessel under stable conditions, which includes a moisture-free environment that does not contain trace amounts of moisture. The storage and delivery container is specifically designed to allow delivery of high purity, vapor phase antimony-containing dopant material at a steady, sufficient and sustained flow rate.Type: GrantFiled: February 22, 2019Date of Patent: July 14, 2020Assignee: Praxair Technology, Inc.Inventors: Aaron Reinicker, Ashwini K Sinha, Douglas C Heiderman
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Patent number: 9938212Abstract: Disclosed is an integrated manufacturing process to co-produce (E) 1-chloro-3,3,3-trifluoropropene, (E) 1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single starting feed material or a mixture of unsaturated hydrochlorocarbon feed materials comprising 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloropropene. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E) 1-chloro-3,3,3-trifluoro-propene (1233zd (E)) from these feed materials, which may also include 240fa. In the second liquid phase fluorination reactor 1233zd (E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E) 1,3,3,3-tetrafluoropropene (1234ze (E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst.Type: GrantFiled: March 28, 2012Date of Patent: April 10, 2018Assignee: Honeywell International Inc.Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung
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Patent number: 9452958Abstract: This invention provides a process for producing a fluoroolefin comprising reacting, in a vapor phase, a fluorinating agent and a chlorine-containing alkene or a chlorine-containing alkane in the presence of at least one catalyst selected from the group consisting of chromium oxide containing a Group 5 element and fluorinated chromium oxide containing a Group 5 element. According to the process of the present invention, the target fluoroolefin can be obtained with high starting material conversion and good selectivity.Type: GrantFiled: January 24, 2013Date of Patent: September 27, 2016Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Daisuke Karube, Takehiro Chaki, Masami Nishiumi, Takashi Shibanuma, Masashi Arai
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Patent number: 9334210Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,1,3,3-tetrachloroprop-1-ene (HCO-1230za) and hydrogen fluoride. Such compositions are useful as feed stock in the production of HFC-245fa and HCFO-1233zd.Type: GrantFiled: March 13, 2013Date of Patent: May 10, 2016Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Stephen A. Cottrell, Hang T. Pham
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Patent number: 9222177Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,3,3,3-tetrachloroprop-1-ene (HCO-1230zd) and hydrogen fluoride. Such compositions are useful as a feed stock in the production of HFC245fa and HCFO1233zd.Type: GrantFiled: March 13, 2013Date of Patent: December 29, 2015Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Ryan Hulse, Hang T. Pham
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Patent number: 9096489Abstract: The invention provides a process for preparing 3,3,3-trifluoropropene (1243zf), the process comprising contacting a compound of formula CX3CH2CH2X or CX3CH?CH2, with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst, wherein each X independently is F, Cl, Br or I, provided that in the compound of formula CX3CH?CH2, at least one X is not F.Type: GrantFiled: April 9, 2010Date of Patent: August 4, 2015Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew Paul Sharratt, Claire McGuinness
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Patent number: 9051231Abstract: According to the first characteristic of the present invention, there is provided a production process for 1,3,3,3-tetrafluoropropene including: the first step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride thereby obtaining 1-chloro-3,3,3-trifluoropropene; and the second step of reacting 1-chloro-3,3,3-trifluoropropene obtained in the first step with hydrogen fluoride in a gaseous phase in the presence of a fluorination catalyst. According to the second characteristic of the present invention, there is provided a dehydration process including bringing 1,3,3,3-tetrafluoropropene containing at least water into contact with zeolite.Type: GrantFiled: September 24, 2009Date of Patent: June 9, 2015Assignee: Central Glass Company, LimitedInventors: Fuyuhiko Sakyu, Satoshi Yoshikawa, Satoru Okamoto, Yasuo Hibino, Yoshio Nishiguchi
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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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Patent number: 8916733Abstract: A process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of contacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of a catalyst having about 25 to about 99.9 mole percent antimony pentachloride and about 0.1 to about 75 mole percent of a metal of a Lewis acid under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane. There is a second process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating about 75 to about 99.9 mole percent 2-chloro-3,3,3-trifluoropropene and about 0.1 to about 25 mole percent of one or more other hydrocarbons having at least one chlorine atom in the presence of a catalyst of fluorinated antimony pentachloride under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane. There is yet another process for hydrofluorinating 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane.Type: GrantFiled: June 15, 2009Date of Patent: December 23, 2014Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
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Patent number: 8889924Abstract: The present invention provides a simple three step process for the production of 1,3,3,3-tetrafluoropropene (HFO-1234ze). In the first step, carbon tetrachloride is added to vinyl fluoride to afford the compound CCl3CH2CHClF (HCFC-241fb). HCFC-241fb is then fluorinated with anhydrous HF to afford CF3CH2CHClF (HCFC-244fa) in the second step. Dehydrochlorination of HCFC-244fa, in the third step, affords the desired product, CF3CH?CHF (HFO-1234ze). Following similar chemistry, vinyl chloride may be used in place of vinyl fluoride.Type: GrantFiled: February 4, 2013Date of Patent: November 18, 2014Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, Rajiv Ratna Singh, Andrew Joseph Poss, David Nalewajek
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Patent number: 8889925Abstract: The present invention provides a process of fluorination in liquid phase in a solvent medium of a compound of formula (II) CX1X2?CZCX3X4X5, in which Z represents H, Cl or F, and each X1 represents independently hydrogen or chlorine, given that at least one of the X1 represents a chlorine.Type: GrantFiled: March 10, 2010Date of Patent: November 18, 2014Assignee: Arkema FranceInventor: Anne Pigamo
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Publication number: 20140303410Abstract: Disclosed is a process involving contacting a hydrohalobutane selected from the group consisting of CF2HCHClCH2CCl2H, CF3CHClCH2CCl2H, CF3CHClCH2CCl3, CF3CClHCHFCCl2H and CF3CClHCHFCCl3, with HF in a reaction zone in the presence of an antimony halide catalyst selected from SbCl5 and SbF5 to form a first product mixture containing a hydromonochlorofluorobutane. Also disclosed is a process involving contacting a hydrohalopentane selected from the group consisting of CF2HCHClCH2CX2CX3 and CF3CHClCH2CX2CX3, wherein each X is independently selected from the group consisting of F and Cl, and not all X are fluorines, with HF in a reaction zone in the presence of an antimony halide catalyst selected from SbCl5 and SbF5to form a first product mixture containing a hydromonochlorofluoropentane. A compound of the formula CF3CHClCH2CHF2 is also disclosed.Type: ApplicationFiled: October 5, 2012Publication date: October 9, 2014Inventor: Ekaterina N. Swearingen
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Publication number: 20140275646Abstract: The present process relates to a method for minimizing the formation of 1,1,1,2,2-pentafluoropropane in a liquid phase reaction of 2-chloro-3,3,3-trifluoropropene and HF in the presence of a hydrofluorination catalyst comprising: (a) reacting HF with sufficient amount of 2-chloro-3,3,3-trifluoropropene in the presence of a hydrofluorination catalyst under conditions effective to form 2-chloro-1,1,1,2-tetrafluoropropane, the hydrofluorination catalyst being present in sufficient amounts to catalyze said reaction and the 2-chloro-1,1,1,2-tetrafluoropropane being formed with both a conversion of greater than 80% and a 1,1,1,2,2-pentafluoropropane selectivity lower than 20%; and (b) maintaining the 2-chloro-1,1,1,2-tetrafluoropropane being formed with both a conversion of about 80% or more and a 1,1,1,2,2-pentafluoropropane selectivity of about 20% or less by adding said hydrofluorination catalyst to the reactor in small increments.Type: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou WANG, Daniel C. MERKEL, Hsueh Sung TUNG, Haluk KOPKALLI
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Publication number: 20140100393Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).Type: ApplicationFiled: June 28, 2010Publication date: April 10, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Robert C. Johnson, Daniel C. Merkel
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Publication number: 20140012047Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).Type: ApplicationFiled: September 9, 2013Publication date: January 9, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: DANIEL C. MERKEL, STEPHEN A. COTTRELL, ROBERT C. JOHNSON
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Patent number: 8541634Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.Type: GrantFiled: January 14, 2013Date of Patent: September 24, 2013Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Hang T Pham
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Patent number: 8426656Abstract: The disclosed integrated manufacturing process includes a combined liquid phase reaction and purification operation which directly produces trans-1-chloro-3,3,3-trifluoropropene and 3-chloro-1,1,1,3-tetrafluoropropane which is a precursor to the manufacture of trans-1,3,3,3-tetrafluoropropene. The mixture of co-products is easily separated by conventional distillation and 3-chloro-1,1,1,3-tetrafluoropropane is then dehydrochlorinated to produce trans-1,3,3,3-tetrafluoropropene by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrochlorination catalyst.Type: GrantFiled: April 5, 2010Date of Patent: April 23, 2013Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Robert Johnson, Hsueh Sung Tung, Haiyou Wang, Konstantin A. Pokrovski
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Patent number: 8378158Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.Type: GrantFiled: October 5, 2011Date of Patent: February 19, 2013Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Hang T. Pham
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Patent number: 8324436Abstract: A multi-step process for preparing 2,3,3,3-tetrafluoro-1-propene comprising the steps of (a) contacting a starting material comprising 2-chloro-3,3,3-trifluoro-1-propene with hydrogen fluoride in the presence of activated first catalyst selected from the group consisting of antimony-halides, iron-halides, titanium halides, and tin-halides, to produce an intermediate composition; and (b) contacting said intermediate composition with a second catalyst of activated carbon to produce a final product comprising 2,3,3,3-tetrafluoro-1-propene.Type: GrantFiled: November 5, 2008Date of Patent: December 4, 2012Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Barbara A. Light, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
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Patent number: 8247624Abstract: Dehydrohalogenation processes for the preparation of fluoropropenes from corresponding halopropanes, in which the fluoropropenes have the formula CF3CY?CXNHP, wherein X and Y are independently hydrogen or a halogen selected from fluorine, chlorine, bromine and iodine; and N and P are independently integers equal to 0, 1 or 2, provided that (N+P)=2.Type: GrantFiled: September 6, 2011Date of Patent: August 21, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh S. Tung
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Publication number: 20120203036Abstract: A multi-step process for preparing 2,3,3,3-tetrafluoro-1-propene comprising the steps of (a) contacting a starting material comprising 2-chloro-3,3,3-trifluoro-1-propene with hydrogen fluoride in the presence of activated first catalyst selected from the group consisting of antimony-halides, iron-halides, titanium halides, and tin-halides, to produce an intermediate composition; and (b) contacting said intermediate composition with a second catalyst of activated carbon to produce a final product comprising 2,3,3,3-tetrafluoro-1-propene.Type: ApplicationFiled: November 5, 2008Publication date: August 9, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Sudip Mukhopadhyay, Barbara A. Light, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
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Patent number: 8207383Abstract: The present invention provides a process for preparing 1234yf, comprising: (i) contacting 1233xf with hydrogen fluoride HF in gas phase in the presence of a fluorination catalyst under conditions sufficient to produce a reaction mixture; (ii) separating the reaction mixture into a first stream comprising HCl, 1234yf and a second stream comprising HF, unreacted 1233xf and 245cb; (iii) recycling at least a part of the second stream at least in part back to step (i).Type: GrantFiled: December 23, 2010Date of Patent: June 26, 2012Assignee: Arkema FranceInventors: Dominique Deur-Bert, Laurent Wendlinger, Anne Pigamo
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Publication number: 20120059200Abstract: Disclosed is an integrated manufacturing process to co-produce (E)1-chloro-3,3,3-trifluoropropene, (E)1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single chlorinated hydrocarbon feed stock, 240fa. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E)1-chloro-3,3,3-trifluoropropene (1233zd(E)) from 240fa. In the second liquid phase fluorination reactor 1233zd(E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E)1,3,3,3-tetrafluoropropene (1234ze(E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst. This operation may be followed by one or more purification processes to recover the 1234ze(E) product.Type: ApplicationFiled: August 29, 2011Publication date: March 8, 2012Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung, Ian Shankland
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Patent number: 8058486Abstract: A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX2?CCl—CH2X??(Formula I) CX3—CCl?CH2??(Formula II) CX3—CHCl—CH2X??(Formula III) wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.Type: GrantFiled: March 13, 2009Date of Patent: November 15, 2011Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Selma Bektesevic, Robert C. Johnson, Haiyou Wang
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Patent number: 8053613Abstract: A process is disclosed for making CH2ClCF2CClF2. The process involves reacting CH2ClF with CClF?CF2 in an addition reaction zone in the presence of an aluminum halide composition having a bulk formula of AlClxBryF3-x-y wherein the average value of x is 0 to 3, the average value of y is 0 to 3?x, provided that the average values of x and y are not both 0. Also disclosed is a process for making CH2FCF2CF3 that involves reacting the CH2ClCF2CClF2 with HF in a fluorination reaction zone in the presence of a fluorination catalyst. Also disclosed is a process for making CHF?CFCF3 that involves dehydrofluorinating the CH2FCF2CF3.Type: GrantFiled: September 5, 2007Date of Patent: November 8, 2011Assignee: E.I. du Pont de Nemours and CompanyInventor: Allen Capron Sievert
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Patent number: 8034984Abstract: Dehydrohalogenation processes for the preparation of fluoropropenes from corresponding halopropanes, in which the fluoropropenes have the formula CF3CY?CXNHP, wherein X and Y are independently hydrogen or a halogen selected from fluorine, chlorine, bromine and iodine; and N and P are independently integers equal to 0, 1 or 2, provided that (N+P)=2.Type: GrantFiled: September 22, 2010Date of Patent: October 11, 2011Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh S. Tung
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Publication number: 20100331583Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).Type: ApplicationFiled: June 28, 2010Publication date: December 30, 2010Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Robert C. Johnson, Daniel C. Merkel
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Patent number: 7803973Abstract: Dehydrohalogenation processes for the preparation of fluoropropenes from corresponding halopropanes, in which the fluoropropenes have the formula CF3CY?CXNHP, wherein X and Y are independently hydrogen or a halogen selected from fluorine, chlorine, bromine and iodine; and N and P are independently integers equal to 0, 1 or 2, provided that (N+P)=2.Type: GrantFiled: April 16, 2008Date of Patent: September 28, 2010Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh Sung Tung
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Patent number: 7786335Abstract: A process for the production of C2-C4 hydrofluorocarbon, such as 1,1,1,3,3-pentafluoropropane, by contacting a non-fluorinated hydrochlorocarbon with a fluorinating agent, such as hydrogen fluoride, in a liquid catalyst system preferably comprising fluorinated superacid catalyst prepared from SbF5, NbF5, TaF5 or TaF5/SnF4 and HF.Type: GrantFiled: November 3, 2008Date of Patent: August 31, 2010Assignee: Honeywell International Inc.Inventors: David E. Bradley, David Nalewajek, Robert L. Bell
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Patent number: 7714177Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene comprising: a) reacting a compound of the formula (I) CHFX2 with a compound of formula (II) CH2?CF2 to produce a reaction product comprising a compound of formula (III) CHXFCH2CXF2, wherein each X is independently selected from the group consisting of chlorine, bromine and iodine; and (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene.Type: GrantFiled: January 7, 2008Date of Patent: May 11, 2010Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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Publication number: 20090312585Abstract: A process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of contacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of a catalyst having about 25 to about 99.9 mole percent antimony pentachloride and about 0.1 to about 75 mole percent of a metal of a Lewis acid under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane. There is a second process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating about 75 to about 99.9 mole percent 2-chloro-3,3,3-trifluoropropene and about 0.1 to about 25 mole percent of one or more other hydrocarbons having at least one chlorine atom in the presence of a catalyst of fluorinated antimony pentachloride under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane. There is yet another process for hydrofluorinating 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane.Type: ApplicationFiled: June 15, 2009Publication date: December 17, 2009Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
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Publication number: 20090149681Abstract: A process for the production of C2-C4 hydrofluorocarbon, such as 1,1,1,3,3-pentafluoropropane, by contacting a non-fluorinated hydrochlorocarbon with a fluorinating agent, such as hydrogen fluoride, in a liquid catalyst system preferably comprising fluorinated superacid catalyst prepared from SbF5, NbF5, TaF5 or TaF5/SnF4 and HF.Type: ApplicationFiled: November 3, 2008Publication date: June 11, 2009Applicant: HONEYWELL INTERNATIONAL INC.Inventors: David E. Bradley, David Nalewajek, Robert L. Bell
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Publication number: 20090124837Abstract: A multi-step process for preparing 2,3,3,3-tetrafluoro-1-propene comprising the steps of (a) contacting a starting material comprising 2-chloro-3,3,3-trifluoro-1-propene with hydrogen fluoride in the presence of activated first catalyst selected from the group consisting of antimony-halides, iron-halides, titanium halides, and tin-halides, to produce an intermediate composition; and (b) contacting said intermediate composition with a second catalyst of activated carbon to produce a final product comprising 2,3,3,3-tetrafluoro-1-propene.Type: ApplicationFiled: November 5, 2008Publication date: May 14, 2009Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Sudip Mukhopadhyay, Barbara A. Light, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
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Patent number: 7348461Abstract: 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: GrantFiled: October 31, 2003Date of Patent: March 25, 2008Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
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Patent number: 7345209Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene that comprises, in one preferred embodiment, providing a compound of the formula CF3CH2CHFX, wherein X is a selected from the group consisting of chlorine, bromine and iodine, and exposing said compound to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene. Other processes for forming 1,3,3,3-tetrafluoropropene are also disclosed.Type: GrantFiled: April 29, 2005Date of Patent: March 18, 2008Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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Patent number: 7329786Abstract: 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: GrantFiled: September 28, 2001Date of Patent: February 12, 2008Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Chengping Chien, Julie Sacarias, Vimal Sharma
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Patent number: 7319175Abstract: Catalysts such as antimony halides, which are useful in fluorination reactions involving hydrogen fluoride, may be reduced during the reaction and require regeneration. Regenerative oxidation is usually carried out by introducing elemental halogen, preferably fluorine or chlorine, into the reaction mixture. In accordance with the invention elemental halogen is prevented from coming into contact with starting materials or intermediate products which are reactive therewith. This is preferably achieved by withdrawing part of the reaction mixture from the reactor, mixing the withdrawn part with chlorine or fluorine in order to regenerate the catalyst, and thereafter returning the withdrawn part to the reactor.Type: GrantFiled: October 27, 2005Date of Patent: January 15, 2008Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Carsten Brosch
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Patent number: 7317071Abstract: Processes for producing a fluoromonomer from a fluoropolymer, among which one that can be carried out more simply is a process wherein thermal decomposition of a fluoropolymer is preformed by means of a rotary kiln (5) so as to produce a fluoromonomer, the process comprising feeding a fluoropolymer and steam (3) into a rotary kiln and heating the fluoropolymer.Type: GrantFiled: February 27, 2003Date of Patent: January 8, 2008Assignee: Daikin Industries, Ltd.Inventors: Takuya Ichida, Yukio Homoto
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Patent number: 7312367Abstract: The invention provides an economic process for the manufacture of the hydrofluorocarbon 1,1,3,3,3-pentafluoropropene (HFC-1225zc). HFC-1225zc can be made from the dehydrochlorination of 1-chloro-1,1,3,3,3-pentafluoropropane (HCFC-235fa). Alternatively, HFC-1225zc can also be made from the dehydrofluorination of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa). HFC-1225zc) is a compound that has the potential to be used as a low Global Warming Potential refrigerant, blowing agent, aerosol propellant, or solvent.Type: GrantFiled: June 14, 2006Date of Patent: December 25, 2007Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Daniel C. Merkel, Rajiv R. Singh
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Patent number: 7241928Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2?CR3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. New compounds disclosed include CF3CF2CCl2CH2CCl3, CF3CCl2CH2CH2Cl and CF3CCl2CH2CHClF. These compounds are useful as intermediates for producing hydrofluorocarbons.Type: GrantFiled: October 1, 2004Date of Patent: July 10, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur N.Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 7230146Abstract: Dehydrohalogenation processes for the preparation of fluoropropenes from corresponding halopropanes, in which the fluoropropenes have the formula CF3CY?CXNHP, wherein X and Y are independently hydrogen or a halogen selected from fluorine, chlorine, bromine and iodine; and N and P are independently integers equal to 0, 1 or 2, provided that (N+P)=2.Type: GrantFiled: October 27, 2003Date of Patent: June 12, 2007Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh Sung Tung
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Patent number: 7214839Abstract: A manufacturing process for making hydrofluorocarbons (HFCs), by reacting a hydrochlorocarbon and HF in a liquid phase catalytic reactor using a large mole ratio of HF to hydrochlorocarbon to minimize formation of high boiling by-products and improve HF consumption and hydrofluorocarbon yields.Type: GrantFiled: May 23, 2003Date of Patent: May 8, 2007Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Chad L. Marks, Stephen A. Cottrell
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Patent number: 7183448Abstract: A mixture comprising at least 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene is subjected to a distillation operation, and thereby, a distillate comprising an azeotropic composition consisting substantially of 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene is obtained and a bottom product comprising 1,1,1,3,3-pentafluoropropane or 1,1,1-trifluoro-3-chloro-2-propene which each is separated and purified.Type: GrantFiled: November 10, 1999Date of Patent: February 27, 2007Assignee: Daikin Industries, Ltd.Inventors: Tatsuo Nakada, Masayoshi Imoto, Takashi Shibanuma
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Patent number: 7112708Abstract: A process for the production of difluoromethane (HFC-32), 1,1,1-trifluoroethane (HFC-143a) and 1,1-difluoroethane (HFC-152a).Type: GrantFiled: April 1, 2004Date of Patent: September 26, 2006Assignee: Honeywell International Inc.Inventors: Daniel C Merkel, Hsuehsung Tung, Ian Shankland
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Patent number: 7094934Abstract: In a process for producing a hydrogen-containing fluorinated hydrocarbon in which a halogenated hydrocarbon reaction raw material, which includes a chlorinated alkene and/or a hydrogen-containing chlorinated alkane, is subjected to a fluorination reaction with hydrogen fluoride in a liquid phase in a reactor in the presence of a fluorination catalyst to obtain a reaction mixture which includes the hydrogen-containing fluorinated hydrocarbon, the reactor to be used has a portion which is able to contact with the reaction mixture, at least a part of this portion being made of an alloy material of 18 to 20% by weight of chromium, 18 to 20% by weight of molybdenum, 1.5 to 2.2% by weight of at least one element selected from niobium and tantalum and the balance of nickel.Type: GrantFiled: January 31, 2001Date of Patent: August 22, 2006Assignee: Daikin Industries, Ltd.Inventors: Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
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Patent number: 7091388Abstract: The invention provides an economic process for the manufacture of the hydrofluorocarbon 1,1,3,3,3-pentafluoropropene (HFC-1225zc). HFC-1225zc can be made from the dehydrochlorination of 1-chloro-1,1,3,3,3-pentafluoropropane (HCFC-235fa). Alternatively, HFC-1225zc can also be made from the dehydrofluorination of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa). HFC-1225zc) is a compound that has the potential to be used as a low Global Warming Potential refrigerant, blowing agent, aerosol propellant, or solvent.Type: GrantFiled: September 26, 2003Date of Patent: August 15, 2006Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Daniel C. Merkel, Rajiv R. Singh
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Patent number: 7074434Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.Type: GrantFiled: October 29, 2002Date of Patent: July 11, 2006Assignee: Solvay (Societe Anonyme)Inventors: Alain Lambert, Vincent Wilmet
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Patent number: 7071368Abstract: A process for producing 1,1,1-trifluoroethane (HFC-143a) which process comprises reacting hydrogen fluoride with vinylidene chloride along with one or more of 1,1,-dichloro-1-fluoroethane (HCFC-141b), 1-chloro-1,1-difluoroethane (HCFC-142b) and 1,1,1-trichloroethane (HCC-140a) in the presence of pentavalent antimony as a fluorination catalyst under conditions to produce 1,1,1-trifluoroethane (HFC-143a), generally in yields of 90% or more.Type: GrantFiled: February 9, 2005Date of Patent: July 4, 2006Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Robert C. Johnson