Catalyst Utilized Patents (Class 570/156)
  • Patent number: 7880040
    Abstract: Disclosed is a method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CFnCHmXa-m??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where each X is independently Cl, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a-m?0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a C1 addition agent under conditions effective to produce a compound of formula (I).
    Type: Grant
    Filed: November 3, 2006
    Date of Patent: February 1, 2011
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy, Rajiv R. Singh, Haiyou Wang, Robert C. Johnson, Rajesh K. Dubey
  • Publication number: 20110021849
    Abstract: A subject-matter of the invention is a process for the preparation of 2,3,3,3-tetrafluoro-1-propene comprising the following stages: (i) hydrogenation of hexafluoropropylene to give 1,1,1,2,3,3-hexafluoropropane; (ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in the preceding stage to give 1,2,3,3,3-pentafluoro-1-propene; (iii) hydrogenation of the 1,2,3,3,3-pentafluoro-1-propene obtained in the preceding stage to give 1,1,1,2,3-pentafluoropropane; (iv) purification of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage; and (v) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage to give 2,3,3,3-tetrafluoro-1-propene; and (vi) purification of the 2,3,3,3-tetrafluoro-1-propene of the preceding stage.
    Type: Application
    Filed: July 23, 2010
    Publication date: January 27, 2011
    Applicant: Arkema France
    Inventors: Karine Avril, Bertrand Collier
  • Publication number: 20110015452
    Abstract: The invention relates to a method for selective dehydrofluorination on a mixed catalyst based on chromium and nickel on a carrier based on aluminium. The invention is used for the synthesis of 2,3,3,3-tetrafluoro-1-propene and 1,2,3,3,3-pentafluoro-1-propene.
    Type: Application
    Filed: March 27, 2009
    Publication date: January 20, 2011
    Applicant: ARKEMA FRANCE
    Inventors: Michel Devic, Laurent Wendlinger
  • Publication number: 20110015453
    Abstract: 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: Application
    Filed: September 22, 2010
    Publication date: January 20, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh Sung Tung
  • Patent number: 7872161
    Abstract: A process is disclosed for making CF3CF?CH2 The process involves (i) contacting CHCl2CF2CF3 in a reaction zone in the presence of a catalytically effective amount of a dehydrofluorination catalyst to produce CCl2?CFCF3; (ii) contacting CCl2?CFCF3 with H2 formed in (i) in a reaction zone in the presence of a catalyst comprising a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina fluorided alumina, aluminum fluoride and mixtures thereof, to produce a product mixture comprising CF3CF?CH2, wherein the mole ratio of H2 to CCl2?CFCF3 fed to the reaction zone is between about 1:1 and about 4:1 and (iii) recovering CF3CF?CH2 from the product mixture formed in (ii).
    Type: Grant
    Filed: November 15, 2007
    Date of Patent: January 18, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20110004035
    Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
    Type: Application
    Filed: September 13, 2010
    Publication date: January 6, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Publication number: 20100331583
    Abstract: 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: Application
    Filed: June 28, 2010
    Publication date: December 30, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert C. Johnson, Daniel C. Merkel
  • Publication number: 20100324345
    Abstract: Systems and processes relating to the formation and production of CFO-1113 HCFC-123a. Such systems and processes can include one or more reactors in series that react HCFC-123a and base to produce reaction product vapors including CFO-1113. Optionally, a phase transfer agent or catalyst can be added to the reaction to enhance the reaction rate. The CFO-1113 can be separated from the reaction product vapors to produce a CFO-1113 product stream. The reactions can be conducted continuously, and a liquid effluent stream can be removed from the reactors during the reaction. Unreacted HCFC-123a can be separated from the liquid effluent stream and provided back to the reactors.
    Type: Application
    Filed: June 22, 2009
    Publication date: December 23, 2010
    Applicant: Honeywell International Inc.
    Inventors: Selma Bektesevic, Hsueh Sung Harry Tung, Haluk Kopkalli
  • Publication number: 20100320412
    Abstract: A process is disclosed for making CF3CF?CH2 or mixtures thereof with CHF2CF?CHF. This process involves (a) reacting CHCl2CF2CF3, and optionally CHClFCF2CClF2, with H2 in the presence of a catalytically effective amount of a hydrogenation catalyst to form CH3CF2CF3 and, when CHClFCF2CClF2 is present, CH2FCF2CHF2; (b) dehydrofluorinating CH3CF2CF3, and optionally any CH2FCF2CHF2, from (a) to form a product mixture including CF3CF?CH2 and, if CH2FCF2CHF2 is present, CHF2CF?CHF; and optionally (c) recovering CF3CF?CH2, or a mixture thereof with CHF2CF?CHF from the product mixture formed in (b) and/or (d) separating at least a portion of any CHF2CF?CHF in the product mixture formed in (b) from the CF3CF?CH2 in the product mixture formed in (b).
    Type: Application
    Filed: October 31, 2007
    Publication date: December 23, 2010
    Applicant: E.I DU PONT DE NEMOURS AND COMPANY
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20100305370
    Abstract: The invention relates to a gas-phase continuous method for preparing 2,3,3,3-tetrafluoro-1-propene, said method comprising the following steps: (i) hydrogenation of hexafluoropropylene to form 1,1,1,2,3,3-hexafluoropropane; (ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in the previous step to 1,2,3,3,3-pentafluoropropene-1; (iii) hydrogenation of the 1,2,3,3,3-pentafluoropropene-1 obtained in the previous step to form 1,1,1,2,3-pentafluoropropane; and (iv) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the previous step to form 2,3,3,3-tetrafluoro-1-propene.
    Type: Application
    Filed: March 27, 2009
    Publication date: December 2, 2010
    Applicant: Arkema France
    Inventors: Michel Devic, Dominique Guillet, Emmanuel Guiraud, Laurent Wendlinger
  • Publication number: 20100294979
    Abstract: A process for making CHF?CFCF3 is disclosed. The process involves (a) reacting CCl2FCF2CF3 with H2 in the presence of a catalytically effective amount of hydrogenation catalyst to form CH2FCF2CF3; and (b) dehydrofluorinating CH2FCF2CF3from (a) to form CHF?CFCF3. Also disclosed are compositions including CCl3CF2CF3 and HF, wherein the HF is present in an effective amount to form an azeotropic combination with the CCl3CF2CF3; and compositions including CCl2FCF2CF3 and HF, wherein the HF is present in an effective amount to form an azeotropic combination with the CCl2FCF2CF3.
    Type: Application
    Filed: September 5, 2007
    Publication date: November 25, 2010
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventor: Allen Capron Sievert
  • Patent number: 7833434
    Abstract: A process is disclosed for producing 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene. The process involves pyrolyzing 1,1,1,2,3-pentafluoropropane.
    Type: Grant
    Filed: June 22, 2007
    Date of Patent: November 16, 2010
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Mario Joseph Nappa, Allen Capron Sievert
  • Patent number: 7829747
    Abstract: A process for making 1-chloro-3,3,3-trifluoropropene. The process has the following step: dehydrofluorinating 3-chloro-1,1,1,3-tetrafluoropropane under conditions sufficient to effect dehydrofluorination in the presence of a catalyst. Preferred catalysts are selected from the group consisting of (i) one or more halogenated trivalent or higher valent metal oxides, (ii) one or more trivalent or higher valent metal halides, and (iii) one or more natural or synthetic graphite materials.
    Type: Grant
    Filed: April 6, 2009
    Date of Patent: November 9, 2010
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20100268001
    Abstract: Described is a process for preparing a halo-olefin comprising contacting a halogenated hydrocarbon with a metal dehalogenating agent, in a solvent, in the presence of a phase transfer catalyst, under conditions sufficient to dehalogenate said halogenated hydrocarbon to produce a product stream comprising said halo-olefin. In one embodiment, the halogenated hydrocarbon is trifluorotrichloroethane and the halo-olefin is chlorotrifluoroethylene.
    Type: Application
    Filed: April 7, 2010
    Publication date: October 21, 2010
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: MARIO JOSEPH NAPPA, Xuehui Sun
  • Patent number: 7812202
    Abstract: Disclosed is a process for producing hexafluoro-1,3-butadiene, which is used for an etching gas capable of being used in fine processing for semiconductors, safely in industrialization and at low cost economically. Specifically disclosed is a process for producing hexafluoro-1,3-butadiene comprises (1) a step comprising allowing a compound having four carbon atoms each which bonds to an atom selected from the group consisting of a bromine atom, an iodine atom and a chlorine atom, to react with a fluorine gas in the presence of a diluting gas in a gas phase, thereby preparing a mixture containing a product (A), and (2) a step comprising eliminating halogens excluding a fluorine atom with a metal from the product (A) prepared in the step (1) in the presence of a solvent, thereby preparing a mixture containing hexafluoro-1,3-butadiene.
    Type: Grant
    Filed: April 25, 2007
    Date of Patent: October 12, 2010
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 7803973
    Abstract: 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: Grant
    Filed: April 16, 2008
    Date of Patent: September 28, 2010
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh Sung Tung
  • Patent number: 7803974
    Abstract: Disclosed are heterogeneous processes (i) for the hydrogenation of a compound containing at least one unsaturated carbon-carbon bond, and (ii) for the hydro-dehalogenation of a compound containing at least one C—Cl, C—Br or C—I bond. The processes comprise reacting said compound with a hydrogenating agent and a heterogeneous hydrogenation catalyst in the presence of an ionic liquid.
    Type: Grant
    Filed: November 4, 2009
    Date of Patent: September 28, 2010
    Assignee: The Queen's University of Belfast
    Inventors: Kris Anderson, Peter Goodrich, Christopher Hardacre, Sarah Elizabeth Jane McMath
  • Patent number: 7795481
    Abstract: Disclosed herein is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkene with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents with hydrogen. Also disclosed is a catalyst composition for the hydrodechlorination of chlorofluoroalkenes comprising copper metal deposited on a support.
    Type: Grant
    Filed: June 3, 2009
    Date of Patent: September 14, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Ekaterina N. Swearingen
  • Patent number: 7786333
    Abstract: A process for the production of fluorinated olefins, preferably fluorinated propenes, by contacting a feed stream containing a fluorinated olefin and hydrogen with a first amount of catalyst to produce the hydrofluorocarbon, wherein a first exit stream contains unreacted fluorinated olefin and hydrogen; contacting the first exit stream with a second amount of catalyst to produce a hydrofluorocarbon, wherein the second amount of catalyst is preferably greater than the first amount of catalyst; and contacting the hydrofluorocarbon with a catalyst for dehydrohalogenation to produce a product stream of fluorinated olefin.
    Type: Grant
    Filed: February 19, 2009
    Date of Patent: August 31, 2010
    Assignee: Honeywell International, Inc.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Sheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20100187464
    Abstract: Disclosed herein are azeotrope and near-azeotrope compositions comprising E-1,1,1,2,3-pentafluoropropene (E-HFC-1225ye) and hydrogen fluoride. The azeotrope and near-azeotrope compositions are useful in processes to produce and in processes to purify E-HFC-1225ye and/or Z-1,1,1,2,3-pentafluoropropene (Z-HFC-1225ye). Also disclosed are processes for the extractive distillation to separate E-HFC-1225ye from Z-HFC-1225ye.
    Type: Application
    Filed: September 7, 2007
    Publication date: July 29, 2010
    Applicant: E.I. Du Pint De Nemours and Company
    Inventors: Jeffrey P. Knapp, Barry Asher Mahler, Velliyur Nott Mallikarjuna Rao
  • Publication number: 20100185028
    Abstract: To provide a method for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) at a high content ratio, which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (R1214ya). The method comprises subjecting a starting material comprising one isomer or a mixture of at least two isomers of dichloropentafluoropropane (HCFC-225) and having a HCFC-225ca content of less than 60 mol%, to an isomerization reaction in the presence of a Lewis acid catalyst or a metal oxide catalyst so as to increase the HCFC-225ca content in the product to be higher than the content in the starting material.
    Type: Application
    Filed: January 19, 2010
    Publication date: July 22, 2010
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventor: Hidekazu OKAMOTO
  • Publication number: 20100185029
    Abstract: The present invention discloses a process for the synthesis of hydrofluoroolefins (HFO). The process is based on the following two steps: the liquid phase fluorination of a hydrochloropropane(s) to hydrofluoropropane(s) (HFP) followed by the dehydrofluorination of the hydrofluoropropane(s) (HFP) to hydrofluoroolefins (HFO).
    Type: Application
    Filed: June 27, 2008
    Publication date: July 22, 2010
    Applicant: ARKEMA INC.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Laurent Wendlinger
  • Publication number: 20100145111
    Abstract: The invention relates to a process for preparing a compound of formula CF3CF?CHX, CHX2CX?CX2 or a linear or branched C4-7 (hydro)fluoroalkene, wherein each X is, independently, H or F provided that in CHX2CX?CX2 at least one X is F, which process comprises dehydrohalogenating a compound of formula CF3CFYCH2X, CF3CFHCYHX, CHX2CXYCX2H, CHX2CXHCX2Y, or a linear or branched hydro(halo)fluoroalkane, wherein each X is, independently, H or F provided that in CHX2CXYCX2H and CHX2CXHCX2Y at least one X is F, wherein Y is F, Cl, Br, or I, in the presence of a base.
    Type: Application
    Filed: December 18, 2007
    Publication date: June 10, 2010
    Inventors: Andrew Paul Sharratt, Robert Elliott Low, John Charles McCarthy
  • Publication number: 20100145112
    Abstract: Disclosed is a method for producing 3,3,3-trifluoropropyne, which is characterized in that a base is reacted with (Z)-1-halogeno-3,3,3-trifluoropropene represented by formula [1]. It is possible by this production method to obtain 3,3,3-trifluoropropyne with high yield. Furthermore, since waste disposal is also easy, it is a production method that is industrially advantageous.
    Type: Application
    Filed: April 4, 2008
    Publication date: June 10, 2010
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Akira Ishihara, Yasuo Hibino
  • Publication number: 20100130797
    Abstract: The present invention provides a method for producing an olefin represented by General Formula (II): RfCF?CH2 (II) (wherein Rf is defined as below), wherein the method includes the step of contacting a fluorohalide represented by General Formula (I): RfCF2CH2X (I) (wherein Rf is H(CF2)n (n=1 to 8) or F(CF2)n (n=1 to 8), and X is Br or I) with a metal in a reaction medium of a polar organic solvent, or a mixed solvent of water and a polar organic solvent to conduct a dehalogenation reaction. The production method of the present invention provides olefins in a highly selective manner at a low cost and high yield under relatively mild reaction conditions.
    Type: Application
    Filed: October 26, 2007
    Publication date: May 27, 2010
    Inventors: Akinari Sugiyama, Takehiro Chaki
  • Patent number: 7722781
    Abstract: A process is disclosed for the manufacture of CF3CF?CH2 and CF3CH?CHF. The process involves dehydrofluorinating CF3CHFCH2F in the presence of a dehydrofluorination catalyst to produce a product mixture comprising CF3CF?CH2 and CF3CH?CHF, and recovering said CF3CF?CH2 and CF3CH?CHF from the product mixture. The present invention also provides a composition comprising (a) the Z-isomer of CF3CH?CHF and (b) HF; wherein the HF is present in an effective amount to form an azeotropic combination with the Z—CF3CH?CHF.
    Type: Grant
    Filed: June 22, 2007
    Date of Patent: May 25, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Mario Joseph Nappa, Allen Capron Sievert
  • Patent number: 7714177
    Abstract: 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: Grant
    Filed: January 7, 2008
    Date of Patent: May 11, 2010
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
  • Patent number: 7700815
    Abstract: Disclosed is a method for producing fluorinated organic compounds, including petnafluoropropenes, which preferably comprises converting at least one compound of formula (I): CFnXmCFaXbCH2X??(I) to at least one compound of formula (II) CF3CF?CHF??(II) where each X is independently Cl, I or Br; n is 2 or 3; m is 0 or 1, a is 1 or 2, b is 0 or 1, m+n=3 and a+b=2.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: April 20, 2010
    Assignee: Honeywell International Inc
    Inventors: Hsueh Sung Tung, Rajiv R. Singh, Michael Van Der Puy
  • Patent number: 7687670
    Abstract: Disclosed is a process for the co-manufacture of the hydrofluoroolefins HFC-1225ye and HFC-1234yf. The process comprises contacting a blend of 1,1,1,2,3,3-hexafluoropropane and 1,1,1,2,3-pentafluoropropane at a temperature of from about 200° C. to about 500° C. with a catalyst, optionally in the presence of an inert gas. The catalyst includes, but is not limited to, aluminum fluoride; fluorided alumina; metals on aluminum fluoride; metals on fluorided alumina; oxides, fluorides, and oxyfluorides of magnesium, zinc and mixtures of magnesium and zinc and/or aluminum; lanthanum oxide and fluorided lanthanum oxide; chromium oxides, fluorided chromium oxides, and cubic chromium trifluoride; carbon, acid-washed carbon, activated carbon, three dimensional matrix carbonaceous materials; and metal compounds supported on carbon.
    Type: Grant
    Filed: March 29, 2007
    Date of Patent: March 30, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Mario Joseph Nappa
  • Publication number: 20100076231
    Abstract: A process is disclosed for making CH2?CFCF3. The process involves contacting CH2ClCF2CF3 with H2 in a reaction zone in the presence of a catalyst including a catalytically effective amount of palladium supported on a support selected from chromium oxide, fluorinated chromium oxide, chromium fluoride, aluminum oxide, aluminum fluoride and/or fluorinated alumina, to produce CH2?CFCF3. The mole ratio of H2 to the CH2ClCF2CF3 fed to the reaction zone is between about 1:1 and about 4:1.
    Type: Application
    Filed: October 31, 2007
    Publication date: March 25, 2010
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7678949
    Abstract: A process for the manufacture of CF3CH?CHF and/or CF3CF?CH2 is disclosed. The process involves (a) reacting HF and chlorine and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or Cl) to produce a product including both CF3CCI2CCIF2 and CF3CCIFCCI2F; (b) reacting CF3CCI2CCIF2 and CF3CCIFCCI2F produced in (a) with hydrogen to produce a product including both CF3CH2CHF2 and CF3CHFCH2F; (c) dehydrofluorinating CF3CH2CHF2 and CF3CHFCH2F produced in (b) to produce a product including both CF3CH?CHF and CF3CF?CH2; and (d) recovering CF3CH?CHF and/or CF3CF?CH2 from the product produced in (c). In (a), both CF3CCI2CCIF2 and CF3CCIFCCI2F are produced in the presence of a chlorofluorination catalyst consisting of (i) compositions comprising a crystalline alpha-chromium oxide where at least 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by copper, and (ii) compositions of (i) which have been treated with a fluorinating agent.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: March 16, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Patent number: 7674939
    Abstract: Disclosed are methods for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CHXCH2X??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where X is independently Cl, Br, I or F, and Z independently is H or F. In certain preferred embodiments, each Z is different.
    Type: Grant
    Filed: November 3, 2006
    Date of Patent: March 9, 2010
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy, Daniel C. Merkel, Rajesh K. Dubey, Jing Ji Ma
  • Publication number: 20100051852
    Abstract: A process is disclosed for making CF3CF?CHF or mixtures thereof with CF2?CFCHF2.
    Type: Application
    Filed: November 15, 2007
    Publication date: March 4, 2010
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7663007
    Abstract: A process for the manufacture of CF3CH?CHF and/or CF3CH?CF2 is disclosed. The process involves (a) reacting HF and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or CI) to produce a product including both CF3CCI?CF2 and CF3CHCICF3; (b) reacting CF3CCI?CF2 and/or CF3CHCICF3 produced in (a) with hydrogen to produce a product including CF3CH2CHF2 and/or CF3CH2CF3; (c) dehydrofluorinating CF3CH2CHF2 and/or CF3CH2CF3 produced in (b) to produce a product comprising CF3CH?CHF and/or CF3CH?CF2; and (d) recovering CF3CH?CHF and/or CF3CH?CF2 from the product produced in (c). In (a), the CF3CCI?CF2 and CF3CHCICF3 are produced in the presence of a fluorination catalyst comprising at least one chromium-containing component selected from (i) a crystalline alpha-chromium oxide where at least 0.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 16, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Publication number: 20100036179
    Abstract: 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: Application
    Filed: July 30, 2009
    Publication date: February 11, 2010
    Inventors: DANIEL C. MERKEL, STEPHEN A. COTTRELL, ROBERT C. JOHNSON
  • Patent number: 7659434
    Abstract: A method for preparing fluorinated organic compounds comprising contacting hydrogen fluoride with at least one compound of formula I: CX3CXYCH3??I where each X is independently Cl, I or Br, and each Y is independently H or F, said contacting step being carried out under conditions effective to produce a compound of formula II CF3CZCH2??II where Z is Cl, I, Br, or F.
    Type: Grant
    Filed: November 3, 2006
    Date of Patent: February 9, 2010
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy, Daniel C. Merkel, Rajesh K. Dubey, Jing Ji Ma, Barbara A. Light, Kim M. Fleming, Cheryl L. Bortz, Richard Udy
  • Publication number: 20100025620
    Abstract: A process is disclosed for making CF3CF?CH2 or mixtures thereof with CHF?CFCHF2. The process involves contacting CCl3CF2CF3 and optionally CCl2FCF2CClF2 with H2 in the presence of a catalyst including a catalytically effective amount of palladium supported on a support of alumina, fluorided alumina and/or aluminum fluoride, to produce a product mixture including CH2?CFCF3 (and when CCl2FCF2CClF2 is present, CHF?CFCHF2); recovering CH2?CFCF3 or a mixture thereof with CHF?CFCHF2 from the product mixture; and optionally, separating at least a portion of any CHF?CFCHF2 in the product mixture from the CH2?CFCF3 in the product mixture. The mole ratio of H2 to the total of CCl3CF2CF3 and CCl2FCF2CClF2 fed to the reaction zone is between about 1:1 and about 5:1.
    Type: Application
    Filed: October 31, 2007
    Publication date: February 4, 2010
    Applicant: E.I.Du Pont De Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Mallikarjuna Nott Rao, Allen Capron Sievert
  • Publication number: 20100022808
    Abstract: A process is disclosed for making CF3CF?CH2 The process involves (i) contacting CHCl2CF2CF3 in a reaction zone in the presence of a catalytically effective amount of a dehydrofluorination catalyst to produce CCl?CFCF3; (ii) contacting CCl2?CFCF3 with H2 formed in (i) in a reaction zone in the presence of a catalyst comprising a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina fluorided alumina, aluminum fluoride and mixtures thereof, to produce a product mixture comprising CF3CF?CH2, wherein the mole ratio of H2 to CCl250 CFCF3 fed to the reaction zone is between about 1:1 and about 4:1 and (iii) recovering CF3CF?CH2 from the product mixture formed in (ii).
    Type: Application
    Filed: November 15, 2007
    Publication date: January 28, 2010
    Applicant: E.I. Du Pont De Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7638660
    Abstract: An integrated process for the manufacture of HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze) by first catalytically dehydrofluorinating 1,1,1,3,3-pentafluoropropane to thereby produce a mixture of cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and hydrogen fluoride. Then optionally recovering hydrogen fluoride, catalytically isomerizing cis-1234ze into trans-1234ze, and recovering trans-1,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: January 5, 2009
    Date of Patent: December 29, 2009
    Assignee: Honeywell International Inc
    Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
  • Publication number: 20090306438
    Abstract: The present disclosure relates to a new and efficient manufacturing process for the production of HFC-1225ye. The process involves contacting at least one hexafluoropropane selected from the group consisting of 1,1,1,2,2,3-hexafluoropropane and 1,1,1,2,3,3-hexafluoropropane with a suitable catalyst in a reactor to obtain a product mixture containing HFC-1225ye (1,2,3,3,3-pentafluoropropene) where the pressure in the reactor ranges from about 0.5 psig to about 100 psig.
    Type: Application
    Filed: September 5, 2007
    Publication date: December 10, 2009
    Inventors: Allen Capron Sievert, Mario Joseph Nappa, Barry Asher Mahler
  • Publication number: 20090287026
    Abstract: Disclosed is a process for producing tetrafluoropropene comprising: (a) catalytically fluorinating at least one tetrafluoropropene in a first reactor to produce HCFO-1233xf; (b) reacting said HCFO-1233xf with hydrogen fluoride in a second reactor to produce HCFC-244bb; (c) recycling at least a portion of said HCFC-244bb back to said first reactor as recycled HCFC-244bb; and (d) catalytically dehydrochlorinating said recycled HCFC-244bb in said first reactor to produce HFO-1234yf.
    Type: Application
    Filed: May 14, 2009
    Publication date: November 19, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk Kopkalli, Yuon Chiu, Hsueh Sung Tung
  • Patent number: 7615668
    Abstract: The present invention provides a novel method for preparing 4,4,4-trifluorobutane-2-one by providing a fluorobutene selected from the group consisting of 2,4,4,4-tetrafluoro-1-butene, (E)-1,1,1,3-tetrafluoro-2-butene, (Z)-1,1,1,3-tetrafluoro-2-butene, and mixture thereof; and reacting the fluorobutene(s) with a proton acid and water.
    Type: Grant
    Filed: October 18, 2004
    Date of Patent: November 10, 2009
    Assignee: Central Glass Co., Ltd.
    Inventors: Adam Alty, Frank Waters, Richard Du Boisson, Yokusu Kuriyama, Masamichi Maruta
  • Publication number: 20090270661
    Abstract: A process for making 1-chloro-3,3,3-trifluoropropene. The process has the following step: dehydrofluorinating 3-chloro-1,1,1,3-tetrafluoropropane under conditions sufficient to effect dehydrofluorination in the presence of a catalyst. Preferred catalysts are selected from the group consisting of (i) one or more halogenated trivalent or higher valent metal oxides, (ii) one or more trivalent or higher valent metal halides, and (iii) one or more natural or synthetic graphite materials.
    Type: Application
    Filed: April 6, 2009
    Publication date: October 29, 2009
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20090264690
    Abstract: A process is disclosed for making CF3CF?CHF. The process involves reacting CF3CClFCCl2F with H2 in a reaction zone in the presence of a catalyst to produce a product mixture comprising CF3CF?CHF. The catalyst has a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina, fluorided alumina, aluminum fluoride and mixtures thereof and the mole ratio of H2 to CF3CClFCCl2F fed to the reaction zone is between about 1:1 and about 5:1. Also disclosed are azeotropic compositions of CF3CClFCCl2F and HF and azeotropic composition of CF3CHFCH2F and HF.
    Type: Application
    Filed: June 22, 2007
    Publication date: October 22, 2009
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Velliyur Nott Mallikarjuna Rao, Mario Joseph Nappa, Allen Capron Sievert
  • Patent number: 7595426
    Abstract: Method for the production of 1,3,5-trifluoro-2,4,6-trichlorobenzene from fluorobenzene comprising steps A) and B): A) chlorination of fluorobenzene derivatives of formula (II), in which X=fluorine of H, Z=nitro, bromo or chloro and n=0 or 1-4 and B) fluorination of the distillation residue and separation by distillation of the 1,3,5-trifluoro-2,4,6-trichlorobenzene thus produced.
    Type: Grant
    Filed: April 21, 2006
    Date of Patent: September 29, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Rack, Sebastian Peer Smidt, Manuel Budich, Volker Maywald, Michael Keil, Bernd Wolf
  • Publication number: 20090240089
    Abstract: Disclosed herein is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkene with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents with hydrogen. Also disclosed is a catalyst composition for the hydrodechlorination of chlorofluoroalkenes comprising copper metal deposited on a support.
    Type: Application
    Filed: June 3, 2009
    Publication date: September 24, 2009
    Applicant: E.I.DE PONT DE NEMOURS AND COMPANY
    Inventors: MARIO JOSEPH NAPPA, EKATERINA N. SWEARINGEN
  • Publication number: 20090216053
    Abstract: Disclosed is a process for producing hexafluoro-1,3-butadiene, which is used for an etching gas capable of being used in fine processing for semiconductors, safely in industrialization and at low cost economically. Specifically disclosed is a process for producing hexafluoro-1,3-butadiene comprises (1) a step comprising allowing a compound having four carbon atoms each which bonds to an atom selected from the group consisting of a bromine atom, an iodine atom and a chlorine atom, to react with a fluorine gas in the presence of a diluting gas in a gas phase, thereby preparing a mixture containing a product (A), and (2) a step comprising eliminating halogens excluding a fluorine atom with a metal from the product (A) prepared in the step (1) in the presence of a solvent, thereby preparing a mixture containing hexafluoro-1,3-butadiene.
    Type: Application
    Filed: April 25, 2007
    Publication date: August 27, 2009
    Applicant: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Publication number: 20090209791
    Abstract: A process for the production of fluorinated olefins, preferably fluorinated propenes, by contacting a feed stream containing a fluorinated olefin and hydrogen with a first amount of catalyst to produce the hydrofluorocarbon, wherein a first exit stream contains unreacted fluorinated olefin and hydrogen; contacting the first exit stream with a second amount of catalyst to produce a hydrofluorocarbon, wherein the second amount of catalyst is preferably greater than the first amount of catalyst; and contacting the hydrofluorocarbon with a catalyst for dehydrohalogenation to produce a product stream of fluorinated olefin.
    Type: Application
    Filed: February 19, 2009
    Publication date: August 20, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Sheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7560602
    Abstract: A process for the production of fluorinated olefins, preferably fluorinated propenes, by contacting a feed stream containing a fluorinated olefin and hydrogen with a first amount of catalyst to produce the hydrofluorocarbon, wherein a first exit stream contains unreacted fluorinated olefin and hydrogen; contacting the first exit stream with a second amount of catalyst to produce a hydrofluorocarbon, wherein the second amount of catalyst is preferably greater than the first amount of catalyst; and contacting the hydrofluorocarbon with a catalyst for dehydrohalogenation to produce a product stream of fluorinated olefin.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: July 14, 2009
    Assignee: Honeywell International Inc.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Scheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7557254
    Abstract: A method for preparing fluorinated organic compounds wherein at least one fluorinated olefin is reacted with methyl fluoride in the gas-phase and in the presence of a Lewis Acid catalyst to form at least one product having at least 3 carbon atoms.
    Type: Grant
    Filed: June 6, 2008
    Date of Patent: July 7, 2009
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Hsueh Sung Tung, Haridasan Nair, Jingji Ma