Catalyst Utilized Patents (Class 570/156)
  • Publication number: 20090156869
    Abstract: Disclosed is a process comprising reacting CF3CCl2CF2CF3 (CFC-318ma) with hydrogen in the presence of a dehalogenation catalyst to produce CF3CCl=CFCF3(CFC-1317mx). Also disclosed is a process comprising reacting CF3CCl?CFCF3 (CFC-1317mx) with hydrogen in the presence of a dehalogenation catalyst to produce CF3C?CCF3 (hexafluoro-2-butyne). Hexafluoro-2-butyne can be used to produce CF3CH?CHCF2CF3 (1,1,1,4,4,5,5,5-octafluoro-2-pentene).
    Type: Application
    Filed: December 15, 2008
    Publication date: June 18, 2009
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventor: Mario Joseph Nappa
  • Publication number: 20090143604
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol.
    Type: Application
    Filed: November 20, 2008
    Publication date: June 4, 2009
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Publication number: 20090127496
    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: Application
    Filed: June 22, 2007
    Publication date: May 21, 2009
    Inventors: Velliyur Nott Mallikarjuna Rao, Mario Joseph Nappa, Allen Capron Sievert
  • Publication number: 20090118554
    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: Application
    Filed: August 4, 2006
    Publication date: May 7, 2009
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Publication number: 20090099395
    Abstract: There is provided a method for producing 1,3,3,3-tetrafluoropropene. This method includes dehydrofluorinating 1,1,1,3,3-pentafluoropropane in gas phase in the presence of a zirconium compound-carried catalyst in which a zirconium compound is carried on a metal oxide or activated carbon.
    Type: Application
    Filed: December 12, 2008
    Publication date: April 16, 2009
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Fuyuhiko Sakyu, Yasuo Hibino
  • Publication number: 20090088593
    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: Application
    Filed: September 28, 2007
    Publication date: April 2, 2009
    Applicant: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Rajiv R. Singh, Michael Van Der Puy
  • Patent number: 7504547
    Abstract: Disclosed herein is a method of preparing a perfluoroalkadiene. A dihaloperfluorocarbon used as a starting material is added dropwise to a nonpolar organic solvent, a metal powder and an organic metal compound. The dihaloperfluorocarbon is slowly added dropwise in a temperature range from 30° C. to 150° C. for a certain period of time. Moreover, the nonpolar organic solvent used may be benzene, toluene, xylene, etc., and the organic metal compound is used by being dissolved in ethyl ether or tetrahydrofuran at a concentration of 1 to 3M. The metal powder used may be Mg, Zn, Cd, etc.
    Type: Grant
    Filed: May 2, 2007
    Date of Patent: March 17, 2009
    Assignee: Foosung Co., Ltd.
    Inventors: Hae-Seok Ji, Ook-Jae Cho, Jae-Gug Ryu, Young-Hoon Ahn, Bong-Suk Kim, Dong-Hyun Kim
  • Publication number: 20090043138
    Abstract: A process for the manufacture of CF3CH?CHF and/or CF3CH?CF2 is disclosed. The process involves 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: Application
    Filed: August 4, 2006
    Publication date: February 12, 2009
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Patent number: 7485760
    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 24, 2007
    Date of Patent: February 3, 2009
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
  • Patent number: 7482499
    Abstract: The present invention provides novel compounds, 2,4,4,4-tetrafluoro-1-butene and (E)- and (Z)-1,1,1,3-tetrafluoro-2 butenes. Furthermore, the present invention provides the following novel first and second processes for producing 2,4,4,4-tetrafluoro-1-butene, (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes, and 1,1,3-trifluorobutadiene. The first process is a process for producing 2,4,4,4-tetrafluoro-1-butene by heating 1,1,1,3,3-pentaflurobutane at from about 200° C. to about 700° C. The second process is a process for producing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes by bringing 1,1,1,3,3-pentafluorobutane with a base. By the first and second processes, it is possible to obtain respective target fluorobutenes with high selectivity. In third to fifth processes, 2,4,4,4-tetrafluoro-1-butene, (E)- and (Z)-1,1,1,3-tetrafluoro-2-butene, and 1,1,3,-trifluorobutadiene can be produced by heating 1,1,1,3,3-pentafluorobutane in the presence of a catalyst.
    Type: Grant
    Filed: April 28, 2004
    Date of Patent: January 27, 2009
    Assignee: Central Glass Company, Limited
    Inventors: Adam C. Alty, Richard A. Du Boisson
  • Publication number: 20090018375
    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: Application
    Filed: March 29, 2007
    Publication date: January 15, 2009
    Inventor: Mario Joseph Nappa
  • Patent number: 7473810
    Abstract: Provided is a method for selectively preparing 2-chloropentafluoropropene comprising catalytic dechlorination of 1,2,2-trichloro-1,1,3,3,3-pentafluoropropane in the presence of hydrogen and a noble metal catalyst. Also provided is method for dechlorinating a vicinal chloride substituted organic compound using a palladium/barium sulfate catalyst.
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: January 6, 2009
    Assignee: Honeywell International Inc.
    Inventors: Michael Van Der Puy, Jingji Ma
  • Patent number: 7470827
    Abstract: Described are compositions adapted to catalyze the vapor phase dehydrohalogenation of 1,1,2-trihaloethane to 1,1-dihaloethylene, e.g., 1,1,2-trichloroethane to vinylidene chloride. These materials include activated carbon and at least one benzimidazole-containing material defined herein as including benzimidazole, a derivative thereof, a salt thereof or mixtures thereof. Also described are methods for producing and using these catalytic compositions.
    Type: Grant
    Filed: June 3, 2005
    Date of Patent: December 30, 2008
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Yurii Oleksiyovych Serhuchev, Yurii Vasyliyovych Bilokopytov, Igorlvanovych Chernobaev
  • Publication number: 20080207962
    Abstract: A catalyst composition is disclosed that includes chromium, oxygen, and at least two of gold, silver, and palladium as essential constituent elements. The amount of modifier metals (gold, silver, and/or palladium) in the composition is from about 0.05 atom % to about 10 atom % based on the total amount of chromium and modifier metals. Also disclosed is a process for changing the fluorine distribution (i.e., content and/or arrangement) in a hydrocarbon or halogenated hydrocarbon in the presence of the catalyst composition; and methods for preparing said catalyst composition. One preparation method involves (a) co-precipitating a solid by adding ammonium hydroxide (aqueous ammonia) to an aqueous solution of soluble salts of modifier metals and a soluble chromium salt that contains at least three moles of nitrate per mole of chromium in the solution and has a modifier metal content of from about 0.
    Type: Application
    Filed: February 21, 2008
    Publication date: August 28, 2008
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20080207963
    Abstract: A method for preparing a catalyst composition suitable for increasing the fluorine content in a hydrocarbon or a halogenated hydrocarbon is disclosed. The method involves (a) co-precipitating a solid by adding ammonium hydroxide to an aqueous solution of a soluble trivalent chromium salt and a soluble salt of a modifier metal selected from silver and palladium, that contains at least three moles of nitrate (i.e., NO3?) per mole of chromium (i.e., Cr+3) in the solution and has a modifier metal concentration of from about 0.05 atom % to about 10 atom % of the total concentration of modifier metal and chromium in the solution to form an aqueous mixture containing co-precipitated solid and dissolved ammonium nitrate; and after at least three moles of ammonium hydroxide per mole of chromium in the solution has been added to the solution, (b) drying said aqueous mixture formed in (a); and (c) calcining the dried solid formed in (b) in an atmosphere containing at least 10% oxygen by volume (e.g., air).
    Type: Application
    Filed: February 21, 2008
    Publication date: August 28, 2008
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7396965
    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: May 12, 2005
    Date of Patent: July 8, 2008
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, HsuehSung Tung, Haridasan Nair, Jingji Ma
  • Patent number: 7358405
    Abstract: A process for obtaining vinyl compounds by dehalogenation of halofluorinated compounds with aromatic substituents, having formula: T-Ar—(O)y—CFX?—CF2X???(I) wherein: X?=F, Cl, Br, I; X?=Cl, Br, I; y=0,1; when y=0 X??F; T=H, —(O)y—CFX?—CF2X?, wherein y, X? and X? are as above; Ar is a monocyclic, bicyclic or tricyclic bivalent aromatic radical from 6 to 14 carbon atoms, optionally containing heteroatoms, or Ar is formed of two aromatic rings linked by a bivalent radical; said process characterized in that the halofluorinated compounds are dehalogenated in the presence of a transition metal, by operating in a biphasic system of solvents immiscible among each other, formed of a (per)fluorinated solvent and a dipolar aprotic or protic solvent (co-solvent), wherein the ratio moles co-solvent/equivalents of the halofluorinated compound with aromatic substituents ranges from 0.5 to 10.
    Type: Grant
    Filed: May 3, 2006
    Date of Patent: April 15, 2008
    Assignee: Solvay Solexis SpA
    Inventors: Ivan Wlassics, Vito Tortelli
  • Patent number: 7348461
    Abstract: 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: Grant
    Filed: October 31, 2003
    Date of Patent: March 25, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
  • Patent number: 7345209
    Abstract: 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: Grant
    Filed: April 29, 2005
    Date of Patent: March 18, 2008
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
  • Publication number: 20080051610
    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: Application
    Filed: January 24, 2007
    Publication date: February 28, 2008
    Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
  • Patent number: 7329786
    Abstract: 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: Grant
    Filed: September 28, 2001
    Date of Patent: February 12, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Chengping Chien, Julie Sacarias, Vimal Sharma
  • Patent number: 7271301
    Abstract: A gold-lined pyrolysis reactor is used to pyrolyze compounds to form fluoroolefins like tetrafluoroethylene and hexafluoropropylene in high yield, with minimum to no formation of perfluoroisobutylene, chlorotrifluoroethylene, coke, salts, or polymer.
    Type: Grant
    Filed: February 22, 2006
    Date of Patent: September 18, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Peter Gideon Gelblum, Norman Herron, Charles Joseph Noelke, Velliyur Nott Mallikarjuna Rao
  • Patent number: 7268261
    Abstract: Methods and materials are disclosed for the recovery of valuable hydrofluorocarbons and subsequent conversion to environmentally inert compounds. More specifically methods and materials are provided for recovering hydrofluorocarbons such as HFC-227, HFC-236, HFC-245, HFC-125, HFC-134, HFC-143, HFC-152, HFC-32, HFC-23 and their respective isomers. Processes are provided for converting hydrofluorocarbons such as these to fluoromonomer precursors such as CFC-217, CFC-216, CFC-215, CFC-115, CFC-114, CFC-113, CFC-112, HCFC-22, CFC-12, CFC-13 and their respective isomers. Materials, methods and schemes are provided for the conversion of these fluoromonomer precursors to fluoromonomers such as HFP, PFP, TFP, TFE, and VDF.
    Type: Grant
    Filed: August 31, 2005
    Date of Patent: September 11, 2007
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Vicki Hedrick, Stephen M. Brandstadter, Mitchel Cohn
  • Patent number: 7250540
    Abstract: A process for manufacturing fluoroolefins comprising perfluorinating a starting material comprising at least one carbon-bonded hydrogen by electrochemical fluorination, dissociating this separated effluent in a pyrolysis, quenching and separating the effluent to yield tetrafluoroethylene and/or hexafluoropropylene.
    Type: Grant
    Filed: June 29, 2005
    Date of Patent: July 31, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: Gerald L. Bauer, Jeffrey D. Weigelt, Klaus Hintzer, Gernot Loehr, Werner Schwertfeger, Arthur A. Ponelis
  • Patent number: 7241928
    Abstract: 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: Grant
    Filed: October 1, 2004
    Date of Patent: July 10, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur N.Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7183448
    Abstract: 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: Grant
    Filed: November 10, 1999
    Date of Patent: February 27, 2007
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuo Nakada, Masayoshi Imoto, Takashi Shibanuma
  • Patent number: 7164050
    Abstract: A process for preparing a halo-olefin to minimize one or more side reactions which form at least one impurity, said process comprising contacting a halogenated hydrocarbon with a metal dehalogenating agent dissolved in a solvent under conditions sufficient to dehalogenate said halogenated hydrocarbon to produce a product stream comprising said halo-olefin and at least one impurity, said metal dehalogenating agent having an average particle size within a range of average particle sizes, said impurity concentration of said product stream being essentially constant within said range and increasing significantly below said range.
    Type: Grant
    Filed: May 2, 2005
    Date of Patent: January 16, 2007
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, William R. Jones
  • Patent number: 7030283
    Abstract: This invention relates to a process for the preparation of 1,1-difluoroolefins, e.g., difluorovinyl cycloaliphatic compounds such as difluorovinylcyclohexane and derivatives by the dehydrofluorination of a trifluoromethyl-substituted cycloaliphatic compound and the resulting compositions. This method utilizes a “sterically hindered super-base” system represented by the formula M+?NRR?; where M is Na or K and R is a secondary, or tertiary alkyl or cycloalkyl group of amines for effecting dehydrofluorination of the trifluoromethyl group leading to the difluorovinyl based cycloaliphatic compounds. The sterically hindered super base can be formed by the, in situ, reaction of a sodium or potassium alkoxide, e.g., KtBuO with a lithium dialkylamide where the lithium is bonded to nitrogen atom of an amine bearing secondary or tertiary aliphatic groups.
    Type: Grant
    Filed: January 23, 2004
    Date of Patent: April 18, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Kathryn Sue Hayes, Guido Peter Pez
  • Patent number: 6963016
    Abstract: The present invention relates to a process for the synthesis of highly active modified carbon supported palladium catalyst by simultaneously impregnating activated carbon with a palladium precursor and an aluminium precursor. The carbon supported palladium catalyst is useful for the hydrodechlorination of dichlorodifluoromethane to produce difluoromethane.
    Type: Grant
    Filed: August 29, 2003
    Date of Patent: November 8, 2005
    Assignee: Council of Scientific and Industrial Research
    Inventors: Janmanchi K. Murthy, Sridara C. Shekar, Kamaraju S. Ramarao, Burri D. Raju, Kondapuram Vijaya Raghavan
  • Patent number: 6703533
    Abstract: A process is disclosed for producing (CF3)2C═CH2, CF3CH═CF2, CF2═C(CF3)OCF2CHF2 and C6H5C(CF3)═CF2. The process involves contacting the corresponding fluorocarbon starting material selected from (CF3)2CFCH2F, (CF3)2CHF, (CF3)2CFOCF2CHF2 and C6H5CF(CF3)2, in the vapor phase, with a defluorination reagent selected from carbon, copper, iron nickel and zinc at an elevated temperature of at least 300 ° C.
    Type: Grant
    Filed: November 21, 2001
    Date of Patent: March 9, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Gennadii Gerskovich Belen'Kii, Viacheslav Alexandrovich Petrov, Sergei Arnol'Dovich Postovoi, Paul Raphael Resnick, Yurii Vilovich Zeifman
  • Patent number: 6683226
    Abstract: A process for the manufacture of CF3CF═CF2 is disclosed. The process involves contacting 2,3-dichloro-1,1,1,2,3,3-hexafluoropropane with at least 0.1 mole of hydrogen in a reaction vessel of titanium, nickel or iron or their alloys, which is either empty or packed with particles or formed shapes of titanium, nickel or iron or their alloys, at a temperature within the range of from about 350° C. to about 600° C. and for a time sufficient to produce hexafluoropropene. Also disclosed are compositions which comprise hydrogen fluoride in combination with an effective amount of CClF2CClFCF3 to form an azeotrope or azeotrope-like composition with hydrogen fluoride. The compositions contain from about 8.7 to 33.6 mole percent CClF2CClFCF3.
    Type: Grant
    Filed: February 14, 2003
    Date of Patent: January 27, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Allen Capron Sievert, V. N. Mallikarjuna Rao
  • Patent number: 6583328
    Abstract: A method for the production of 1,1,1,3,3-pentafluoropropene, and particularly to a method characterized by high conversion, yield and selectivity by contacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with hydrogen in the presence of a metal-containing catalyst. The 1,1,1,3,3-pentafluoropropene then can be reacted with hydrogen in the presence of a metal-containing catalyst to produce 1,1,1,3,3-pentafluoropropane.
    Type: Grant
    Filed: April 5, 1999
    Date of Patent: June 24, 2003
    Assignee: PCBU Services, Inc.
    Inventors: John Cheng-Ping Qian, Julia Ann Sacarias
  • Patent number: 6476281
    Abstract: A method for the production of 1,1,1,3,3-pentafluoropropene, and particularly to a method characterized by high conversion, yield and selectivity by contacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with hydrogen in the presence of a metal-containing catalyst. The 1,1,1,3,3-pentafluoropropene then can be reacted with hydrogen in the presence of a metal-containing catalyst to produce 1,1,1,3,3-pentafluoropropane.
    Type: Grant
    Filed: July 26, 2001
    Date of Patent: November 5, 2002
    Assignee: PCBU Services, Inc.
    Inventors: John Cheng-Ping Qian, Julia Ann Sacarias
  • Publication number: 20020151755
    Abstract: A process in gaseous phase to obtain CFC 113a starting from CFC 113, wherein CFC 113, optionally diluted with a gas inert under the reaction conditions, is let flow on a catalyst formed by aluminum fluoride.
    Type: Application
    Filed: February 12, 2002
    Publication date: October 17, 2002
    Applicant: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Letanzio Bragante
  • Publication number: 20020115895
    Abstract: A process is disclosed for producing the pentfluropropenes of the formula CF3CX=CF2, where X is H or Cl. The process involves hydrodehalogenating CF3CCl2CF3 with hydrogen at an elevated temperature in the vapor phase over a catalyst comprising an elemental metal, metal oxide, metal halide and/or metal oxyhalide (the metal being copper, nickel, chromium and the halogen of said halides and said oxyhalides being fluorine and/or chlorine. Processes for producing the hydrofluorocarbons CF3CH2CHF2, CF3CHFCF3 and CF3CH2CF3 are also disclosed which involve (a) hydrodehalogenating CF3CCl2CF3 with the hydrogen as indicated above to produce a product comprising CF3CCl=CF2, CF3CH=CF2, HCl and HF; and (b) either reacting the CF3CCl=CF2 and/or CF3CH=CF2 produced in (a) in the vapor phase with hydrogen to produce CF3CH2CHF2, reacting CF3CCl=CF2 produced in (a) with HF to produce CF3CHFCF3, or reacting the CF3CH=CF2produced in (a) with HF to produce CF3CH2CF3.
    Type: Application
    Filed: January 30, 2002
    Publication date: August 22, 2002
    Inventors: William H. Manogue, V.N. Mallikarjuna Rao, Allen Capron Sievert, Steven H. Swearingen
  • Patent number: 6403847
    Abstract: One or more materials selected from 1,1,1,3,3-pentachloropropane, 1,1,3,3-tetrachloropropene and 1,3,3,3-tetrachloropropene are used as the specific materials described above. Before submitting the materials and HF to a fluorination reaction, almost all water is removed from them. To continuously manufacture useful intended products efficiently as well as to prevent deactivation of the catalyst and the accumulation of organic substances with high boiling points when manufacturing said useful 1,1,1,3,3-pentafluoropropane and/or 1-chloro-3,3,3-trifluoropropene, by fluorinating the specific materials with HF in the presence of a catalyst.
    Type: Grant
    Filed: March 20, 2001
    Date of Patent: June 11, 2002
    Assignee: Daikin Industries Ltd.
    Inventors: Tatsuo Nakada, Takashi Shibanuma, Noriaki Shibata
  • Patent number: 6380446
    Abstract: Halogenated compounds are dehydrohalogenated in a multi-stage bubble reactor wherein agitation of the reactor contents is provided by in situ generation and vaporization of reaction product having a boiling point lower than that of the reactants.
    Type: Grant
    Filed: March 7, 2001
    Date of Patent: April 30, 2002
    Assignee: DuPont Dow Elastomers, L.L.C.
    Inventors: David William Drew, Terry Wayne Redwine
  • Patent number: 6369284
    Abstract: A process is disclosed for the manufacture of a pentafluoropropene of the formula: CFX═CYCF3 where X is selected from H and F and where Y is F when X is H and Y is H when X is F. The process involves contacting a hexafluoropropane of the formula: CF2XCHYCF3 at a temperature of from about 200° C. to 500° C. with a catalyst, optionally in the presence of an inert gas. Suitable catalysts include (1) catalysts of (a) at least one compound selected from the oxides, fluorides and oxyfluorides of magnesium, zinc and mixtures of magnesium and zinc, and optionally (b) at least one compound selected from the oxides, fluorides and oxyfluorides of aluminum; provided that the atomic ratio of aluminum to the total of magnesium and zinc in said catalyst is about 1:4, or less (e.g., 1:9), (2) lanthanum fluoride, (3) fluorided lanthanum oxide, (4) activated carbon, and (5) three-dimensional matrix carbonaceous materials.
    Type: Grant
    Filed: July 26, 1999
    Date of Patent: April 9, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, V.N.Mallikarjuna Rao
  • Publication number: 20020035300
    Abstract: A process is disclosed for producing the pentafluoropropenes of the formula CF 3 CX═CF 2 , where X is H or Cl. The process involves hydrodehalogenating CF 3 CCl 2 CF 3 with hydrogen at an elevated temperature in the vapor phase over a catalyst comprising an elemental metal, metal oxide, metal halide and/or metal oxyhalide (the metal being copper, nickel, chromium and the halogen of said halides and said oxyhalides being fluorine and/or chlorine).
    Type: Application
    Filed: August 19, 1999
    Publication date: March 21, 2002
    Inventors: V.N. MALLIKARJUNA RAO, ALLEN CAPRON SIEVERT
  • Patent number: 6359183
    Abstract: Advantageous processes are disclosed for the production of vinyl fluoride. Also disclosed are advantageous methods which may be employed for the preparation of catalysts useful in such processes. Included are methods which involve (i) reducing surface B2O3 present in a bulk chromium oxide composition containing surface B2O3 by treating said composition with HF at an elevated temperature and/or (ii) treating a bulk chromium oxide composition containing B2O3 to enrich the B2O3 present on its surface by heating said composition in oxygen or an oxygen-containing environment (e.g., air) at an elevated temperature for a time sufficient to enrich the B2O3 on the surface of the composition by at least a factor of two compared to the surface analysis of the untreated bulk composition.
    Type: Grant
    Filed: December 1, 1999
    Date of Patent: March 19, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Frank J. Christoph, George W. Coulston, Velliyur Nott Mallikarjuna Rao
  • Patent number: 6262321
    Abstract: This invention relates to a process for the production of vinyl fluoride by dehydrofluorination of 1,1-difluoroethane in the presence of a catalyst containing magnesium and/or zinc.
    Type: Grant
    Filed: May 18, 1999
    Date of Patent: July 17, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao
  • Patent number: 6235951
    Abstract: The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes the steps of (a) adding hydrogen fluoride to 1-chloro-3,3,3-trifluoropropene in the presence of an addition catalyst to obtain 1,1,1,3-tetrafluoro-3-chloropropane; and (b) disproportionating the 1,1,1,3-tetrafluoro-3-chloropropane into the 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3,3-dichloropropane, in the presence of a disproportionation catalyst. This method is a useful method for producing 1,1,1,3,3-pentafluoropropane in an industrial scale, because its steps (a) and (b) are respectively superior in selectivity and yield. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. This method is useful, because yield of 1-chloro-3,3,3-trifluoropropene is high.
    Type: Grant
    Filed: November 20, 1996
    Date of Patent: May 22, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Fuyuhiko Sakyu, Satoshi Yoshikawa, Yasuo Hibino, Yoshihiko Gotoh, Ryouichi Tamai
  • Patent number: 6166156
    Abstract: Halofluorinated alkylene monomers are made by a method comprising the steps of: (a) subjecting a first polymer which is the reaction product of a fluorinated vinyl monomer and a vinyl comonomer to dehydrohalogenation to form a second polymer; (b) treating the second polymer with an oxidizing agent to form an oxidation product consisting of a .alpha., .omega.-dicarboxylic acid or an ester derivative thereof; and (c) treating said oxidation product with a reducing agent to form a reduction product consisting of a a .alpha., .omega.-diol. Preferably, the first polymer has a structure of --[CH.sub.2 CYZ(CF.sub.2 CFX).sub.n ].sub.m -- wherein X and Y=F, Cl or Br; X and Y may be the same or different; Z=H, F, Cl, Br, alkyl or perfluoroalkyl containing from about 1 to about 10 carbon atoms; n=an integer larger than about 1; and m is an integer between about 2 and about 10.sup.5. The .alpha., .omega.-dicarboxylic acids and .alpha., .omega.-diols produced herein can be directly used as polycondensation monomers.
    Type: Grant
    Filed: November 12, 1998
    Date of Patent: December 26, 2000
    Inventors: Chengjiu Wu, Baopei Xu, James T. Yardley
  • Patent number: 6124510
    Abstract: Preparation of cis/trans 1234ze monomer is provided, by dehydrofluorination of 245fa using an alkaline solution or using a gas phase catalyzed process.
    Type: Grant
    Filed: July 21, 1998
    Date of Patent: September 26, 2000
    Assignee: Elf Atochem North America, Inc.
    Inventors: Maher Y. Elsheikh, Paul D. Fellenger
  • Patent number: 6093859
    Abstract: A process is disclosed for producing the hydrofluorocarbon CF.sub.3 CH.dbd.CF.sub.2. The process involves dehydrofluorinating CF.sub.3 CH.sub.2 CF.sub.3 at an elevated temperature in the vapor phase over a catalyst of (1) aluminum fluoride, (2) fluorided alumina, (3) metal supported on a trivalent aluminum compound containing fluoride anion, (4) lanthanum fluoride, (5) fluorided lanthanum oxide, (6) metal supported on a trivalent lanthanum compound containing fluoride anion, (7) trivalent chromium compounds and/or (8) catalysts of (a) at least one compound selected from the oxides, fluorides and oxyfluorides of magnesium, zinc and mixtures of magnesium and zinc, and optionally (b) at least one compound selected from the oxides, fluorides and oxyfluorides of aluminum, provided that the atomic ratio of aluminum to the total of magnesium and zinc in said catalyst is about 1:4, or less, to produce a product containing CF.sub.3 CH.dbd.CF.sub.2 and HF. The CF.sub.3 CH.dbd.CF.sub.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: July 25, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 6034289
    Abstract: Advantageous processes are disclosed for the production of vinyl fluoride. Also disclosed are advantageous methods which may be employed for the preparation of catalysts useful in such processes. Included are methods which involve (i) reducing surface B.sub.2 O.sub.3 present in a bulk chromium oxide composition containing surface B.sub.2 O.sub.3 by treating said composition with HF at an elevated temperature and/or (ii) treating a bulk chromium oxide composition containing B.sub.2 O.sub.3 to enrich the B.sub.2 O.sub.3 present on its surface by heating said composition in oxygen or an oxygen-containing environment (e.g., air) at an elevated temperature for a time sufficient to enrich the B.sub.2 O.sub.3 on the surface of the composition by at least a factor of two compared to the surface analysis of the untreated bulk composition.
    Type: Grant
    Filed: December 3, 1997
    Date of Patent: March 7, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Frank J. Christoph, George W. Coulston, Velliyur Nott Mallikarjuna Rao
  • Patent number: 6031141
    Abstract: This invention provides a process for the manufacture of a fluoroolefin of the formula (R.sup.1).sub.2 C.dbd.C(R.sup.1).sub.2 wherein each R.sup.1 is independently selected from the group consisting of --H, --F, --CF.sub.3, --CHF.sub.2, --CH.sub.2 F, --C.sub.2 F.sub.5, --C.sub.2 HF.sub.4 and --C.sub.2 H.sub.2 F.sub.3, provided that at least one R.sup.1 is not --H. The process comprises contacting a hydrofluorocarbon of the formula (R.sup.1).sub.2 CHCF(R.sup.1).sub.2 with a catalyst comprising cubic chromium trifluoride, i.e., a chromium trifluoride having an X-ray diffraction powder pattern shown in Table I, at a temperature of from about 200.degree. C. to about 500.degree. C.
    Type: Grant
    Filed: August 6, 1998
    Date of Patent: February 29, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rao V.N. Mallikarjuna, Munirpallam A. Subramanian
  • Patent number: 6018083
    Abstract: A process is disclosed for the separation of a mixture of HF and CF.sub.3 CClFCF.sub.3. The process involves placing the mixture in a separation zone at a temperature of from about -30.degree. C. to about 100.degree. C. and at a pressure sufficient to maintain the mixture in the liquid phase, whereby an organic-enriched phase comprising less than 50 mole percent HF is formed as the bottom layer and an HF-enriched phase comprising more than 90 mole percent HF is formed as the top layer. The organic-enriched phase can be withdrawn from the bottom of the separation zone and subjected to distillation in a distillation column to recover essentially pure CF.sub.3 CClFCF.sub.3. The distillate comprising HF and CF.sub.3 CClFCF.sub.3 can be removed from the top of the distillation column while essentially pure CF.sub.3 CClFCF.sub.3 can be recovered from the bottom of the distillation column.
    Type: Grant
    Filed: April 1, 1999
    Date of Patent: January 25, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: William H. Manogue, Mario Joseph Nappa, Allen Capron Sievert, V. N. Mallikarjuna Rao
  • Patent number: 5986151
    Abstract: A process for the preparation of fluorinated propanes and propenes. CF.sub.3 CH.dbd.CH.sub.2 is produced from CF.sub.3 CH.sub.2 CHF.sub.2 by the sequential steps of dehydrofluorination, a reduction, and a second dehydrofluorination in which the same catalyst is preferably used for each step. Preferably the catalysts is palladium on carbon. The process provides the steps of passing CF.sub.3 CH.sub.2 CHF.sub.2 over a Pd/C catalyst to form CF.sub.3 CH.dbd.CHF; hydrogenating CF.sub.3 CH.dbd.CHF over a Pd/C catalyst to give CF.sub.3 CH.sub.2 CH.sub.2 F; and passing CF.sub.3 CH.sub.2 CH.sub.2 F over a Pd/C catalyst to give CF.sub.3 CH.dbd.CH.sub.2.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: November 16, 1999
    Assignee: AlliedSignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5945573
    Abstract: A process is disclosed for producing the hydrofluorocarbon CF.sub.3 CH.sub.2 CHF.sub.2. The process involves dehydrofluorinating CF.sub.3 CH.sub.2 CF.sub.3 at an elevated temperature in the vapor phase over a catalyst of (1) aluminum fluoride, (2) fluorided alumina, (3) metal supported on a trivalent aluminum compound containing fluoride anion, (4) lanthanum fluoride, (5) fluorided lanthanum oxide, (6) metal supported on a trivalent lanthanum compound containing fluoride anion, (7) trivalent chromium compounds and/or (8) catalysts of (a) at least one compound selected from the oxides, fluorides and oxyfluorides of magnesium, zinc and mixtures of magnesium and zinc, and optionally (b) at least one compound selected from the oxides, fluorides and oxyfluorides of aluminum, provided that the atomic ratio of aluminum to the total of magnesium and zinc in said catalyst is about 1:4, or less, to produce a product containing CF.sub.3 CH.dbd.CF.sub.2 and HF; and reacting the CF.sub.3 CH.dbd.CF.sub.
    Type: Grant
    Filed: January 9, 1998
    Date of Patent: August 31, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao, Allen Capron Sievert