Zinc Containing Catalyst Patents (Class 570/158)
  • Patent number: 9242910
    Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, co-feed species HFC-245cb is added to the reaction at a pressure of at least about 100 psig; and in another embodiment it is added to maintain a mole ratio of HFC-245cb to HCFO-1233xf of between about 0.005:1 to about 1:1. The HFC-245cb may be added as recycled by-product of the reaction and/or added as fresh feed. The HFC-245cb provides elevated pressures to the reaction thereby facilitating reactor operation, mixing and HCFC-244bb product removal. Other co-feed species are also disclosed.
    Type: Grant
    Filed: March 13, 2014
    Date of Patent: January 26, 2016
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
  • Publication number: 20140350310
    Abstract: This disclosure relates to processes of making 1,3,3,3-tetrafluoropropene. The processes involve dehydrofluorinating 1,1,1,3,3-pentafluoropropane in vapor phase in the presence of a catalyst comprising a metal compound supported on alumina to produce a product mixture comprising 1,3,3,3-tetrafluoropropene, wherein said metal compound is selected from the group consisting of salts of sodium, potassium, zinc, magnesium, calcium, cobalt, copper, and chromium, and mixtures thereof.
    Type: Application
    Filed: May 13, 2014
    Publication date: November 27, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: XUEHUI SUN, MARIO JOSEPH NAPPA
  • Patent number: 8829254
    Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: September 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv Ratna Singh, David Nalewajek, Andrew Joseph Poss
  • Patent number: 8664457
    Abstract: A production method of 3,3,3-trifluoropropene includes the step of hydrogenating 1-chloro-3,3,3-trifluoropropene with hydrogen (H2) in a gas phase in the presence of either of: (A) a catalyst having carried on a carrier at least one kind of transition metal selected from the group consisting of ruthenium, nickel, rhodium, iridium, iron, osmium and cobalt, or an oxide of said transition metal; (B) an oxide catalyst of copper and manganese; and (C) a catalyst having carried on a carrier palladium and at least one kind of element selected from the group consisting of bismuth, zinc, copper, silver, lanthanum, lead, zirconium, niobium, hafnium, magnesium, tin and arsenic.
    Type: Grant
    Filed: January 18, 2011
    Date of Patent: March 4, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Fuyuhiko Sakyu, Yasuo Hibino
  • Patent number: 8648222
    Abstract: There is provided methods for making a catalyst composition represented by the formula MX/M?F2 wherein MX is an alkali metal halide; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?; M?F2 is a bivalent metal fluoride; and M? is a bivalent metal ion. There is also a method for making a fluorinated olefin.
    Type: Grant
    Filed: July 6, 2011
    Date of Patent: February 11, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20140031596
    Abstract: The invention relates to a process for preparing a C3-6 (hydro)fluoroalkene comprising dehydrohalogenating a C3-6 hydro(halo)fluoroalkane in the presence of a zinc/chromia catalyst, wherein the C3-6 (hydro)fluoroalkene produced is isomerised in the presence of the zinc/chromia catalyst.
    Type: Application
    Filed: October 1, 2013
    Publication date: January 30, 2014
    Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.
    Inventors: Andrew Paul Sharratt, Leslie Richard Seddon
  • Publication number: 20140012050
    Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the compound of formula CF3CHFCH2X to produce 1234yf.
    Type: Application
    Filed: August 19, 2013
    Publication date: January 9, 2014
    Applicant: Mexichem Amanco Holding S.A. de C.V.
    Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
  • Patent number: 8546623
    Abstract: The invention relates to a process for preparing a C3-6 hydrofluoroalkene comprising dehydrohalogenating a C3-6 hydrohalofluoroalkane in the presence of a zinc/chromia catalyst.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: October 1, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew Paul Sharratt, Leslie Seddon
  • Patent number: 8536387
    Abstract: Process for preparing perfluoro-1,3-butadiene, comprising the following steps: A) preparation of fluoro-halo-butanes of formula: CF2YI—CFYII—CFYII—CF2YI??(V) in which YI and YII, which may be identical or different, may be H, Cl or Br, with the condition that YI and YII are not simultaneously hydrogen; starting with a chloroolefin having the formula: CY?Y?CY?Cl??(II) in which Y, Y?, Y?, which may be identical or different, are H, Cl or Br, with the condition that Y, Y?, Y? are not simultaneously hydrogen; and performing the following steps: a fluorodimerization, and a fluorination with elemental fluorine, the order of the two steps also possibly being inverted, a dehalogenation or dehydrohalogenation step being performed between the two steps, B) dehalogenation or dehydrohalogenation of the fluoro-halo compounds of formula (V) to give the compound perfluoro-1,3-butadiene.
    Type: Grant
    Filed: December 24, 2008
    Date of Patent: September 17, 2013
    Assignee: Solvay Solexis. S.p.A.
    Inventors: Vito Tortelli, Stefano Millefanti, Serena Carella
  • Patent number: 8536388
    Abstract: The present invention provides a process for its preparation comprising (a) converting 1,1,1-trifluoro-2,3-dichloropropane (243db) to 3,3,3-trifluoro-2-chloro-prop-1-ene (CF3CCI?CH2) in the presence of a first catalyst in a first reactor, (b) contacting CF3CCI?CH2 with a fluorinating agent in the presence of a second catalyst in a second reactor to produce a compound of formula CF3CFXCH3, wherein X?Cl or F, and (c) dehydrohalogenating the compound of formula CF3CFXCH3 to produce 2,3,3,3-tetrafluoropropene (1234yf).
    Type: Grant
    Filed: April 9, 2009
    Date of Patent: September 17, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: John W. Smith, Claire E McGuiness, Andrew Paul Sharratt
  • Publication number: 20130211155
    Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.
    Type: Application
    Filed: February 4, 2013
    Publication date: August 15, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: Honeywell International Inc.
  • Patent number: 8436217
    Abstract: Disclosed is a fully integrated process for making 1,1,1,3,3-pentafluoropropane (HFC-245fa), trans-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), and trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)).
    Type: Grant
    Filed: April 25, 2011
    Date of Patent: May 7, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • Patent number: 8373010
    Abstract: Disclosed is a process for the preparation of 3,3,3-trifluoropropene comprising the steps of; (1) fluorination of 240fa to form 245fa; (2) conversion of 245fa to a cis/trans mixture of 1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form 254fb ; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene. Alternatively or additionally, a second process for the preparation of the desired compound comprises the following steps; (1) fluorination of HCC-240fa to form HCFC-244fa; (2) conversion of 244fa to a cis/trans mixture of HFO-1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form HFC-254fb; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene.
    Type: Grant
    Filed: September 3, 2010
    Date of Patent: February 12, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Selma Bektesevic
  • Patent number: 8338651
    Abstract: Halogenated alkenes, especially fluorinated alkenes can be prepared from halogenated and fluorinated alkanes, respectively, by dehydrohalogenation or dehydrofluorination in the presence of a high-surface metal fluoride or oxifluoride. Preferably, trifluoroethylene, pentafluoropropene, tetrafluorobutenes or trifluorobutadiene are prepared. Aluminum fluoride is highly suitable. The metal fluoride or oxifluoride can be applied supported on a carrier.
    Type: Grant
    Filed: July 11, 2008
    Date of Patent: December 25, 2012
    Assignee: Solvay Fluor GmbH
    Inventors: Ercan Uenveren, Erhard Kemnitz, Stephan Rudiger, Anton Dimitrov, Johannes Eicher
  • Publication number: 20120302804
    Abstract: A production method of 3,3,3-trifluoropropene includes the step of hydrogenating 1-chloro-3,3,3-trifluoropropene with hydrogen (H2) in a gas phase in the presence of either of: (A) a catalyst having carried on a carrier at least one kind of transition metal selected from the group consisting of ruthenium, nickel, rhodium, iridium, iron, osmium and cobalt, or an oxide of said transition metal; (B) an oxide catalyst of copper and manganese; and (C) a catalyst having carried on a carrier palladium and at least one kind of element selected from the group consisting of bismuth, zinc, copper, silver, lanthanum, lead, zirconium, niobium, hafnium, magnesium, tin and arsenic.
    Type: Application
    Filed: January 18, 2011
    Publication date: November 29, 2012
    Applicant: Central Glass Company, Limited
    Inventors: Fuyuhiko Sakyu, Yasuo Hibino
  • Publication number: 20120271070
    Abstract: Disclosed is a fully integrated process for making 1,1,1,3,3-pentafluoropropane (HFC-245fa), trans-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), and trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)).
    Type: Application
    Filed: April 25, 2011
    Publication date: October 25, 2012
    Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • Publication number: 20120071699
    Abstract: The invention provides a process for preparing 3,3,3-trifluoropropene (1243zf), the process comprising contacting a compound of formula CX3CH2CH2X or CX3CH?CH2, with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst, wherein each X independently is F, Cl, Br or I, provided that in the compound of formula CX3CH?CH2, at least one X is not F.
    Type: Application
    Filed: April 9, 2010
    Publication date: March 22, 2012
    Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.
    Inventors: Andrew Paul Sharratt, Claire McGuinness
  • Patent number: 8080696
    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: Grant
    Filed: October 26, 2007
    Date of Patent: December 20, 2011
    Assignee: Daikin Industries, Ltd.
    Inventors: Akinari Sugiyama, Takehiro Chaki
  • Patent number: 8053612
    Abstract: A process for making a fluorinated olefin. The process has the step of dehydrochlorinating a hydrochlorofluorocarbon having at least one hydrogen atom and at least one chlorine atom on adjacent carbon atoms in the presence of a catalytically effective amount of a catalyst composition. The catalyst composition is represented by the following: n wt. % MX/M?OyFz, wherein 0<y<1 and 0<z<2 and wherein y+z/2=1; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?, M? is a bivalent metal ion; wherein n is a weight percentage of about 0.05% to about 50% MX based on the total weight of the MX and M?OyFz, and wherein y and z are the mole fractions of oxygen and fluorine in M?OyFz, respectively. There are also methods for making catalyst compositions.
    Type: Grant
    Filed: May 27, 2009
    Date of Patent: November 8, 2011
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8044251
    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: Grant
    Filed: April 7, 2010
    Date of Patent: October 25, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Xuehui Sun
  • Publication number: 20110237844
    Abstract: Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides a method for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and 3,3,3-trifluoropropene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.
    Type: Application
    Filed: March 11, 2011
    Publication date: September 29, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Hsueh Sung Tung, Haiyou Wang
  • Publication number: 20110237843
    Abstract: Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides methods for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and ethylene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.
    Type: Application
    Filed: March 11, 2011
    Publication date: September 29, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Hsueh Sung Tung, Haiyou Wang
  • Patent number: 7994371
    Abstract: Disclosed is a process for the making chlorotrifluoroethylene. The process comprises the step of reacting 1,1,2-trichlorotrifluoroethane with a reducing metal in the presence of a polar aprotic solvent under conditions sufficient to form chlorotrifluoroethylene.
    Type: Grant
    Filed: May 14, 2010
    Date of Patent: August 9, 2011
    Assignee: Honeywell International, Inc.
    Inventors: Selma Bektesevic, Michael John Murphy
  • Publication number: 20110160499
    Abstract: 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: Application
    Filed: December 23, 2010
    Publication date: June 30, 2011
    Applicant: Arkema France
    Inventors: Laurent Wendlinger, Anne Pigamo, Dominique Deur-Bert
  • Patent number: 7829748
    Abstract: The invention provides an economic process for the manufacture of 1,3,3,3-tetrafluoropropene (HFO-1234ze) by a two stage process. A vapor phase hydrofluorination of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) into 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa) and/or 1,1,1,3,3-pentafluoropropane (HFC-245fa) is conducted, followed by the thermal dehydrochlorination of HCFC-244fa and dehydro fluorination of HFC-245fa into HFO-1234ze in the presence of a catalyst which comprises one or more of alkali metal halides, alkaline earth metal halides, halogenated metal oxides, zero oxidation state metals, zinc halides, palladium halides, and activated carbon.
    Type: Grant
    Filed: September 21, 2009
    Date of Patent: November 9, 2010
    Assignee: Honeywell International Inc.
    Inventors: Hsuehsung Tung, Robert C. Johnson, Daniel C. Merkel, Haiyou Wang
  • Publication number: 20100210882
    Abstract: The invention relates to a process for preparing a C3-6 hydrofluoroalkene comprising dehydrohalogenating a C3-6 hydrohalofluoroalkane in the presence of a zinc/chromia catalyst.
    Type: Application
    Filed: October 3, 2007
    Publication date: August 19, 2010
    Inventors: Andrew Paul Sharratt, Leslie Seddon
  • 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
  • Patent number: 7723552
    Abstract: A process for the making chlorotrifluoroethylene. The process has the step of reacting 1,1,2-trichlorotrifluoroethane with a reducing metal in the presence of a polar aprotic solvent under conditions sufficient to form chlorotrifluoroethylene.
    Type: Grant
    Filed: August 7, 2009
    Date of Patent: May 25, 2010
    Assignee: Honeywell International Inc.
    Inventors: Selma Bektesevic, Michael John Murphy
  • 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
  • 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: 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: 20080300432
    Abstract: Chemical production processes are provided that include reacting a metal comprising olefin to form a conjugated olefin; reacting a heterohalogenated olefin to form a conjugated olefin; reacting a halogenated alkane to form a conjugated olefin; and/or reacting a hydrohalogenated olefin to form a conjugated olefin. Chemical production systems are also provided that can include: a first reactant reservoir configured to house a perhalogenated olefin; a second reactant reservoir configured to house a catalyst mixture; a first reactor coupled to both the first and second reservoirs, the first reactor configured to house a metal-comprising mixture and receive both the perhalogenated olefin form the first reactant reservoir and the reactant mixture from the second reactant reservoir; and a product collection reservoir coupled to the first reactor and configured to house a conjugated olefin.
    Type: Application
    Filed: August 26, 2005
    Publication date: December 4, 2008
    Inventors: Vicki Hedrick, Stephan Brandstadter, Janet Boggs, Mitchel Cohn, Venkat Reddy Ghojala, P.V. Ramachandran
  • 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: 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
  • 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: 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: 6992038
    Abstract: The present invention is to solve the problems caused by a conventional method for producing a zinc chloride-loaded support wherein zinc chloride is adsorbed on a solid support in an aqueous solution of zinc chloride. The problems include environmental destruction caused by the treatment of a used aqueous solution of zinc chloride, corrosion to a reactor, a threat to health for workers, deterioration of zinc chloride due to deliquescence thereof, and reduction of specific surface area.
    Type: Grant
    Filed: November 18, 2003
    Date of Patent: January 31, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Mitsuo Narita, Masaki Tabata, Kazuhisa Hayakawa
  • Patent number: 6610896
    Abstract: A process for preparing a perfluoroalkadiene compound of formula (I) CF2═CF—(CF2)n-4—CF═CF2  (I) (wherein n is an integer from 4 to 20) by the deiodofluorination of a compound of formula (II) I—(CF2)n—I  (II) (wherein n is as defined above), characterised in that said deiodofluorination is conducted in the presence of metallic zinc and a nitrogen-containing organic compound.
    Type: Grant
    Filed: July 5, 2002
    Date of Patent: August 26, 2003
    Assignee: Daikin Industries, Ltd.
    Inventors: Jun Miki, Hitoshi Yoshimi, Hirokazu Aoyama
  • Publication number: 20030100806
    Abstract: A method of preparing vicinal difluoro aromatic compounds in high yield from hydroxy aromatic compounds and a method of preparing intermediates thereof. The hydroxy aromatic compound can be a mono-, bi- or tricyclic aromatic in which the rings are separate or fused. One or more of the rings can contain heteroatoms, such as oxygen, nitrogen, or sulfur, and can contain one or more substitutions, in addition to the hydroxy substitution.
    Type: Application
    Filed: December 30, 2002
    Publication date: May 29, 2003
    Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
  • Patent number: 6534456
    Abstract: The invention relates to a plurality of liquid cleansing compositions having at least one lamellar phase which possesses a lotion-like appearance conveying signals of enhanced moisturization and at least one abutting isotropic phase having enhanced cleansing ability. The inventive composition is contained in a partitionless container in one embodiment conveying signals of a plurality of compositions. This multiphase composition is stable upon storage and is dispensed as a striped product where typically one stripe has primarily a cleansing function and a second stripe has primarily a moisturization function.
    Type: Grant
    Filed: January 23, 2001
    Date of Patent: March 18, 2003
    Assignee: Unilever Home and Personal Care USA, division of Conopco, Inc.
    Inventors: Christine Hayward, Rosa Paredes
  • Publication number: 20020193643
    Abstract: A process for preparing a perfluoroalkadiene compound of formula (I)
    Type: Application
    Filed: July 5, 2002
    Publication date: December 19, 2002
    Inventors: Jun Miki, Hitoshi Yoshimi, Hirokazu Aoyama
  • 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
  • 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: 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: 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: 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: 5914423
    Abstract: A process for the preparation of a compound of formula (I):HetSCH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 (I)wherein Het is an optionally substituted 5- or 6-membered heterocyclic ring, which comprises reacting a compound of formula (II):HetSH (II)with a compound of formula (III):CF.sub.2 .dbd.CHCH.sub.2 CH.sub.2 L (III)wherein L is chlorine or bromine or a group --OSO2R.sup.a wherein R.sup.a is a C1-4 alkyl group or a phenyl group optionally substituted by a C1-4 alkyl group.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: June 22, 1999
    Assignee: Zeneca, Limited
    Inventors: Michael Drysdale Turnbull, Nigel James Willetts, Steven Fitzjohn, Prafula Govind Kholia, Harjindersingh Bansal, Alfred Glyn Williams
  • Patent number: 5880315
    Abstract: A process for the manufacture of vinyl fluoride (i.e., CH.sub.2 .dbd.CHF, VF or 1141) from 1,1-difluoroethane (i.e., CH.sub.3 CHF.sub.2, F152a or HFC-152a) is disclosed which involves contacting the 1,1-difluoroethane at an elevated temperature (200.degree. C.-400.degree. C.) with a multiphase catalyst composition consisting essentially of (a) fluorides of at least one divalent metal selected from magnesium and zinc, and (b) fluorides of trivalent aluminum, in which phases of the divalent fluorides are homogeneously dispersed with phases of the trivalent fluorides.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: March 9, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: V.N. Mallikarjuna Rao, Munirpallam A. Subramanian
  • Patent number: 5856593
    Abstract: Production of trifluoroethylene from 1,1,1,2-tetrafluoroethane and/or 1,1,2,2-tetrafluoroethane in a heated reaction zone in the presence of a Lewis acid catalyst.
    Type: Grant
    Filed: February 4, 1997
    Date of Patent: January 5, 1999
    Assignee: Imperial Chemical Industries PLC
    Inventors: Richard Llewellyn Powell, Andrew Paul Sharratt
  • Patent number: 5728903
    Abstract: A method for producing a fluorine-containing silicone compound, which comprises subjecting a compound of the following formula (I) and a hydrosilicone compound having at least one hydrogen atom bonded to a silicon atom to hydrosilylation to obtain a fluorine-containing silicone compound having a R.sup.f --Q--CR.sup.1 R.sup.2 CR.sup.3 HCR.sup.4 R.sup.5 -- group bonded to the silicon atom:R.sup.f --Q--CR.sup.1 R.sup.2 CR.sup.3 .dbd.CR.sup.4 R.sup.5(I)wherein R.sup.f is a monovalent fluorine-containing organic group, Q is a single bond or a bivalent organic group containing no fluorine atom, and each of R.sup.1 to R.sup.5 which are independent of one another, is a hydrogen atom or a monovalent organic group.
    Type: Grant
    Filed: January 6, 1997
    Date of Patent: March 17, 1998
    Assignee: Asahi Glass Company Ltd.
    Inventors: Yutaka Furukawa, Mami Kotera, Seisaku Kumai, Kazuya Oharu, Toshihiko Toma