Transition Metal Halide Containing Catalyst Patents (Class 570/168)
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Patent number: 11207668Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a chromium oxyfluoride catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.Type: GrantFiled: November 19, 2019Date of Patent: December 28, 2021Assignee: THE CHEMOURS COMPANY FC, LLCInventor: Mario Joseph Nappa
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Patent number: 11148994Abstract: The invention relates to a new process for the manufacture of fluoroaryl compounds and derivatives thereof, in particular of fluorobenzenes and derivatives thereof, and especially wherein said manufacture relates to an environmentally friendly production of the said compounds. Thus, the present invention overcomes the disadvantages of the prior art processes, and in a surprisingly simple and beneficial manner, and as compared to the prior art processes, in particular, the invention provides a more efficient and energy saving processes, and also provides a more environmentally friendly process, for the manufacture of nuclear fluorinated aromatics, and preferably of nuclear fluorinated fluorobenzenes. Accordingly, in one aspect of the invention, an industrially beneficial process for preparing fluorobenzenes from halobenzene precursors using HF to form hydrogen halide is provided by the present invention.Type: GrantFiled: June 20, 2020Date of Patent: October 19, 2021Inventors: Hongjun Du, Wenting Wu
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Patent number: 9024093Abstract: Methods for fluorinating organic compounds are described herein.Type: GrantFiled: November 20, 2009Date of Patent: May 5, 2015Assignee: President and Fellows of Harvard CollegeInventors: Tobias Ritter, Takeru Furuya, Pingping Tang
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Patent number: 9000242Abstract: The invention is directed to a catalyst for the gas phase fluorination of 1,1,2-trichloroethane and/or 1,2-dichloroethene with HF to give 1-chloro-2,2-difluoroethane which catalyst is prepared by co-depositing FeCl3 and MgCl2 on chromia-alumina, or co-depositing Cr(NO3)3 and Ni(NO3)2 on active carbon, or by doping alumina with ZnCl2, and to a process for the preparation of 1-chloro-2,2-difluoroethane comprising a catalytic gas phase fluorination of 1,1,2-trichloroethane and/or 1,2-dichloroethene wherein one of the catalysts according to claim 2 or 3 is used.Type: GrantFiled: October 11, 2012Date of Patent: April 7, 2015Assignee: Bayer Intellectual PropertyInventors: Norbert Lui, Shanthan Rao Pamulaparthy, Srinivas Pvss, Thomas Vijaya, Sridhar Madabhushi, Rambabu Yadla, Narsaiah Banda, Sergii Pazenok
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Patent number: 8975455Abstract: The present invention aims in a method wherein tetrachloroethylene (PCE) is reacted with HF in a gas phase in the presence of a catalyst to obtain pentafluoroethane (HFC-125), to reduce production of undesirable by-products and maintain a catalytic activity at a high level over a long period of time while achieving a high conversion ratio of PCE and suppressing deterioration of the catalyst. In a method for producing pentafluoroethane wherein tetrachloroethylene is reacted with HF in a gas phase in the presence of a catalyst to obtain pentafluoroethane, characterized in that chromium oxyfluoride is disposed in a reactor as the catalyst, and oxygen is fed into the reactor together with tetrachloroethylene and HF, at a amount of 0.4-1.8% by mole with respect to tetrachloroethylene.Type: GrantFiled: November 12, 2008Date of Patent: March 10, 2015Assignee: Daikin Industries, Ltd.Inventors: Masatoshi Nose, Kazuhiro Takahashi, Takashi Shibanuma
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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: 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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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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Publication number: 20140309462Abstract: The present disclosure provides a fluorination process which involves reacting a hydrohaloalkene of the formula RfC—Cl?CH2 with HF in a reaction zone in the presence of a fluorination catalyst selected from the group consisting of TaF5 and TiF4 to produce a product mixture containing a hydrohaloalkane of the formula RfCFClCH3, wherein Rf is a perfluorinated alkyl group.Type: ApplicationFiled: November 9, 2012Publication date: October 16, 2014Inventors: Mario Joseph NAPPA, Andrew JACKSON, Daniel C. MERKEL
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Publication number: 20140275648Abstract: The invention relates to a process to produce 244bb from 1233xf in multiple reaction zones whereby the 1233xf starting material is at least 95% converted to 244bb and by-product such as 245cb forms in amounts less than about 2%.Type: ApplicationFiled: March 12, 2014Publication date: September 18, 2014Applicant: HONEYWELL INTERNATIONAL, INC.Inventors: Yuon Chiu, Haluk Kopkalli, Robert A. Smith, Daniel C. Merkel
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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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Patent number: 8648221Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd(E)), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 240fa with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd(E) and 244fa (plus byproduct HCl); (2) the 244fa stream can then be used to directly produce any of the three desired products; (3a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze(E); and/or (3b) the 244fa stream can be dehydrofluorinated to produce 1233zd(E) if more of that product is desired; and/or (3c) the 244fa stream can be further fluorinated to form 245fa.Type: GrantFiled: December 9, 2011Date of Patent: February 11, 2014Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Haiyou Wang, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
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Patent number: 8575407Abstract: A support of metal oxyfluoride or metal halide for a metal-based hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.Type: GrantFiled: March 20, 2012Date of Patent: November 5, 2013Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 8309774Abstract: The invention is directed to a process for preparing 2,2,2,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) 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, 2,2,2,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb); (iii) recycling at least a part of the second stream at least in part back to step (i).Type: GrantFiled: March 9, 2012Date of Patent: November 13, 2012Assignee: Arkema FranceInventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
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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: 8236997Abstract: A process for the production of pentafluoroethane is described. The process comprises reacting perchloroethylene with hydrogen fluoride in the vapor phase in a first reactor or a first plurality of reactors in the presence of a fluorination catalyst to produce a composition comprising dichlorotrifluoroethane, hydrogen chloride, unreacted hydrogen fluoride and perchloroethylene. This composition is subjected to a separation step to yield a purified composition comprising at least 95 weight % of dichlorotrifluorethane and less than 0.5 weight % of compounds having the formula C2C16-XFX, where x is an integer of from 0 to 6, base the total weight of organic compounds in the composition. The composition from the separation step is then reacted with hydrogen fluoride in the vapor phase in a second reactor or a second plurality of reactors in the presence of a fluorination catalyst to produce a composition comprising pentafluoroethane and less than 0.Type: GrantFiled: December 18, 2006Date of Patent: August 7, 2012Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Clive Robert Giddis, Paul Hendry Stewert
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Patent number: 8207384Abstract: The invention provides a process for preparing 1234yf, comprising: (i) contacting 243db 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, 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: Laurent Wendlinger, Anne Pigamo, Dominique Deur-Bert
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Publication number: 20120116131Abstract: A new chromium-containing fluorination catalyst is described. The catalyst comprises an amount of zinc that promotes activity. The zinc is contained in aggregates which have a size across their largest dimension of up to 1 micron. The aggregates are distributed throughout at least the surface region of the catalyst and greater than 40 weight % of the aggregates contain a concentration of zinc that is within ±1 weight % of the modal concentration of zinc in those aggregates.Type: ApplicationFiled: September 4, 2009Publication date: May 10, 2012Applicant: Mexichem Amanco Holdings S.A. DE C.V.Inventor: Andrew P. Sharratt
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Patent number: 8158836Abstract: The invention is directed to a process for preparing 2,3,3,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) 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, 2,3,3,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (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: April 17, 2012Assignee: Arkema FranceInventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
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Patent number: 8058487Abstract: The present invention relates to a continuous process for the fluorination of perchloroethylene (PER) in the gas phase in a single stage with hydrofluoric acid (HF) in the presence of a catalyst to give, as major product, pentafluoroethane. The process is characterized in that it is carried out at a temperature of between 280 and 430° C. and with an HF/PER molar ratio of greater than or equal to 20.Type: GrantFiled: November 30, 2006Date of Patent: November 15, 2011Assignee: Arkema FranceInventors: Beatrice Boussand, Michel Devic
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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: 20110201853Abstract: The present invention relates to methods, process, and integrated systems for economically producing (E)-1-chloro-3,3,3-trifluoropropene via vapor phase and/or liquid processes.Type: ApplicationFiled: February 2, 2011Publication date: August 18, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Hsueh S. Tung, Robert Johnson, Konstantin A. Pokrovski, Daniel C. Merkel
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Publication number: 20110060171Abstract: The present invention relates to a process for the manufacture of pentafluoroethane. It more particularly relates to a process for the manufacture of pentafluoroethane by gas-phase fluorination of perchloroethylene (PER) in the presence of a catalyst, characterized in that (i) the reaction of the PER with HF is carried out with an HF/PER molar ratio of greater than or equal to 20 and a pressure of greater than 5 bar absolute, and that (ii) the stream leaving this reaction step is recycled directly to the reaction step after separation of pentafluoroethane and of HCl.Type: ApplicationFiled: October 10, 2007Publication date: March 10, 2011Applicant: Arkema FranceInventors: Béatrice Boussand, Emmanuel Guiraud
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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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Publication number: 20100268002Abstract: The present invention aims in a method wherein tetrachloroethylene (PCE) is reacted with HF in a gas phase in the presence of a catalyst to obtain pentafluoroethane (HFC-125), to reduce production of undesirable by-products and maintain a catalytic activity at a high level over a long period of time while achieving a high conversion ratio of PCE and suppressing deterioration of the catalyst. In a method for producing pentafluoroethane wherein tetrachloroethylene is reacted with HF in a gas phase in the presence of a catalyst to obtain pentafluoroethane, characterized in that chromium oxyfluoride is disposed in a reactor as the catalyst, and oxygen is fed into the reactor together with tetrachloroethylene and HF, at a amount of 0.4-1.8% by mole with respect to tetrachloroethylene.Type: ApplicationFiled: November 12, 2008Publication date: October 21, 2010Inventors: Masatoshi Nose, Kazuhiro Takahashi, Takashi Shibanuma
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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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Publication number: 20100191025Abstract: The present invention relates to a process for preparing (hydro)(chloro)fluoroolefins comprising at least one step of fluorination in the liquid phase of a (hydro)haloalkane or of a (hydro)haloalkene in the presence of at least one ionic liquid as a catalyst. The ionic liquids are derivatives of Lewis acids based on aluminum, titanium, niobium, tantalum, tin, antimony, nickel, zinc or iron.Type: ApplicationFiled: May 13, 2008Publication date: July 29, 2010Applicant: Arkema FranceInventor: Sylvain Perdrieux
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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: 20090182179Abstract: A process for making 2-chloro-1,1,1,2-tetrafluoropropane comprising hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of: SbCl3, SbCl5, SbF5, TiCl4, SnCl4, Cr2O3, and fluorinated Cr2O3.Type: ApplicationFiled: December 18, 2008Publication date: July 16, 2009Inventors: Daniel C. Merkel, Robert C. Johnson, Hsuehsung Tung
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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: 7420094Abstract: The present invention relates to a process of catalyzed isomerization of HFC-1234ze to make HFC-1234yf. The process comprises contacting HFC-1234ze with a suitable catalyst in a reactor to obtain a product mixture comprising HFC-1234yf.Type: GrantFiled: August 31, 2007Date of Patent: September 2, 2008Assignee: E.I. du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Mario Joseph Nappa
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Publication number: 20080091053Abstract: A process for the manufacture of haloalkanes, or more particularly to a process for the manufacture of 1,1,1,3,3-pentachloropropane (HCC-240fa) and/or and/or 1,1,1,3-tetrachloropropane (HCC-250fb). The process includes (a) mixing a catalyst, co-catalyst and a haloalkane starting material under conditions suitable to produce a homogeneous mixture; (b) reacting the homogeneous mixture with a haloalkene and/or alkene starting material under conditions suitable to produce a haloalkane product stream; and (c) recovering a haloalkane product from said product stream.Type: ApplicationFiled: October 9, 2007Publication date: April 17, 2008Inventors: Hsueh Sung Tung, Ian Shankland
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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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Publication number: 20080058562Abstract: The present invention relates to a process of catalyzed isomerization of HFC-1234ze to make HFC-1234yf. The process comprises contacting HFC-1234ze with a suitable catalyst in a reactor to obtain a product mixture comprising HFC-1234yf.Type: ApplicationFiled: August 31, 2007Publication date: March 6, 2008Applicant: E. I. DUPONT DE NEMOURS AND COMPANYInventors: Viacheslav A. Petrov, Mario Joseph Nappa
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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: 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: 7294747Abstract: Process for the manufacture of 1,1-difluoroethane by liquid-phase fluorination of 1,2-dichloroethane using hydrofluoric acid in the presence of a Lewis acid as catalyst and of FeCl3 as cocatalyst. Process for the manufacture of 1,1-difluoroethylene employing it.Type: GrantFiled: October 17, 2003Date of Patent: November 13, 2007Assignee: Arkema FranceInventor: Phillipe Bonnet
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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: 7176338Abstract: The invention relates to a process for preparing 1,1,1-trifluoro-2,2-dichloroethane (F123). This process consists in placing 1,1,1-trifluoro-2-chloroethane (F133a) in contact with chlorine in the presence of hydrogen fluoride and a fluorination catalyst. F133a may be obtained by fluorination of trichloroethylene, and the F123 may be subsequently fluorinated to F125.Type: GrantFiled: April 1, 2004Date of Patent: February 13, 2007Assignee: AtofinaInventors: Béatrice Boussand, Eric Jorda
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Patent number: 7109386Abstract: Process for the preparation of a halogenated olefin by reaction of an alkyne and/or of an allene compound with a hydrogen halide in a liquid medium comprising at least one hydrohalogenation catalyst comprising at least one palladium compound.Type: GrantFiled: March 20, 2002Date of Patent: September 19, 2006Assignee: Solvay (Societe Anonyme)Inventor: Véronique Mathieu
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Patent number: 7102040Abstract: The invention provides an apparatus useful in fluorinating organic compounds, or more particularly to a reactor system suitable for the fluorination of organic compounds on a commercial scale. The apparatus is also useful in chemical reactions including heating or cooling.Type: GrantFiled: April 4, 2003Date of Patent: September 5, 2006Assignee: Honeywell International Inc.Inventors: Yuon Chiu, Merwyn E. Howells, Stephen A. Cottrell
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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: 7074973Abstract: A process for the preparation of pentafluoroethane is disclosed which involves contacting a mixture comprising hydrogen fluoride and at least one starting material selected from haloethanes of the formula CX3CHX2 and haloethanes of the formula CX2?CX2, where each X is independently selected from the group consisting of F and Cl (provided that no more than four of X are F), with a fluorination catalyst in a reaction zone to produce a product mixture comprising HF, HCl, pentafluoroethane, underfluorinated halogenated hydrocarbon intermediates and less than 0.2 mole percent chloropentafluoroethane based on the total moles of halogenated hydrocarbons in the product mixture. The process is characterized by the fluorination catalyst comprising (i) a crystalline cobalt-substituted alpha-chromium oxide where from about 0.05 atom % to about 6 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by trivalent cobalt (Co+3) and/or (ii) a fluorinated crystalline oxide of (i).Type: GrantFiled: August 21, 2003Date of Patent: July 11, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario J. Nappa, Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Shekhar Subramoney, Munirpallam A. Subramanian, Allen C. Sievert