Zinc Containing Catalyst Patents (Class 570/158)
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Patent number: 9242910Abstract: 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: GrantFiled: March 13, 2014Date of Patent: January 26, 2016Assignee: Honeywell International Inc.Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
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Publication number: 20140350310Abstract: 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: ApplicationFiled: May 13, 2014Publication date: November 27, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: XUEHUI SUN, MARIO JOSEPH NAPPA
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Patent number: 8829254Abstract: 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: GrantFiled: February 4, 2013Date of Patent: September 9, 2014Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, Rajiv Ratna Singh, David Nalewajek, Andrew Joseph Poss
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Patent number: 8664457Abstract: 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: GrantFiled: January 18, 2011Date of Patent: March 4, 2014Assignee: Central Glass Company, LimitedInventors: Fuyuhiko Sakyu, Yasuo Hibino
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Patent number: 8648222Abstract: 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: GrantFiled: July 6, 2011Date of Patent: February 11, 2014Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20140031596Abstract: 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: ApplicationFiled: October 1, 2013Publication date: January 30, 2014Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.Inventors: Andrew Paul Sharratt, Leslie Richard Seddon
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Publication number: 20140012050Abstract: 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: ApplicationFiled: August 19, 2013Publication date: January 9, 2014Applicant: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Patent number: 8546623Abstract: 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: GrantFiled: October 3, 2007Date of Patent: October 1, 2013Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew Paul Sharratt, Leslie Seddon
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Patent number: 8536387Abstract: 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: GrantFiled: December 24, 2008Date of Patent: September 17, 2013Assignee: Solvay Solexis. S.p.A.Inventors: Vito Tortelli, Stefano Millefanti, Serena Carella
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Patent number: 8536388Abstract: 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: GrantFiled: April 9, 2009Date of Patent: September 17, 2013Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire E McGuiness, Andrew Paul Sharratt
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Publication number: 20130211155Abstract: 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: ApplicationFiled: February 4, 2013Publication date: August 15, 2013Applicant: HONEYWELL INTERNATIONAL INC.Inventor: Honeywell International Inc.
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Patent number: 8436217Abstract: 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: GrantFiled: April 25, 2011Date of Patent: May 7, 2013Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
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Patent number: 8373010Abstract: 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: GrantFiled: September 3, 2010Date of Patent: February 12, 2013Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Selma Bektesevic
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Patent number: 8338651Abstract: 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: GrantFiled: July 11, 2008Date of Patent: December 25, 2012Assignee: Solvay Fluor GmbHInventors: Ercan Uenveren, Erhard Kemnitz, Stephan Rudiger, Anton Dimitrov, Johannes Eicher
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Publication number: 20120302804Abstract: 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: ApplicationFiled: January 18, 2011Publication date: November 29, 2012Applicant: Central Glass Company, LimitedInventors: Fuyuhiko Sakyu, Yasuo Hibino
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Publication number: 20120271070Abstract: 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: ApplicationFiled: April 25, 2011Publication date: October 25, 2012Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
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Publication number: 20120071699Abstract: 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: ApplicationFiled: April 9, 2010Publication date: March 22, 2012Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.Inventors: Andrew Paul Sharratt, Claire McGuinness
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Patent number: 8080696Abstract: 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: GrantFiled: October 26, 2007Date of Patent: December 20, 2011Assignee: Daikin Industries, Ltd.Inventors: Akinari Sugiyama, Takehiro Chaki
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Patent number: 8053612Abstract: 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: GrantFiled: May 27, 2009Date of Patent: November 8, 2011Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 8044251Abstract: 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: GrantFiled: April 7, 2010Date of Patent: October 25, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Xuehui Sun
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Publication number: 20110237844Abstract: 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: ApplicationFiled: March 11, 2011Publication date: September 29, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Hsueh Sung Tung, Haiyou Wang
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Publication number: 20110237843Abstract: 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: ApplicationFiled: March 11, 2011Publication date: September 29, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Hsueh Sung Tung, Haiyou Wang
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Patent number: 7994371Abstract: 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: GrantFiled: May 14, 2010Date of Patent: August 9, 2011Assignee: Honeywell International, Inc.Inventors: Selma Bektesevic, Michael John Murphy
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Publication number: 20110160499Abstract: 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: ApplicationFiled: December 23, 2010Publication date: June 30, 2011Applicant: Arkema FranceInventors: Laurent Wendlinger, Anne Pigamo, Dominique Deur-Bert
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Patent number: 7829748Abstract: 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: GrantFiled: September 21, 2009Date of Patent: November 9, 2010Assignee: Honeywell International Inc.Inventors: Hsuehsung Tung, Robert C. Johnson, Daniel C. Merkel, Haiyou Wang
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Publication number: 20100210882Abstract: 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: ApplicationFiled: October 3, 2007Publication date: August 19, 2010Inventors: Andrew Paul Sharratt, Leslie Seddon
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Publication number: 20100185029Abstract: 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: ApplicationFiled: June 27, 2008Publication date: July 22, 2010Applicant: ARKEMA INC.Inventors: Maher Y. Elsheikh, Philippe Bonnet, Laurent Wendlinger
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Patent number: 7723552Abstract: 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: GrantFiled: August 7, 2009Date of Patent: May 25, 2010Assignee: Honeywell International Inc.Inventors: Selma Bektesevic, Michael John Murphy
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Patent number: 7714177Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene comprising: a) reacting a compound of the formula (I) CHFX2 with a compound of formula (II) CH2?CF2 to produce a reaction product comprising a compound of formula (III) CHXFCH2CXF2, wherein each X is independently selected from the group consisting of chlorine, bromine and iodine; and (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene.Type: GrantFiled: January 7, 2008Date of Patent: May 11, 2010Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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Publication number: 20090306438Abstract: 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: ApplicationFiled: September 5, 2007Publication date: December 10, 2009Inventors: Allen Capron Sievert, Mario Joseph Nappa, Barry Asher Mahler
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Publication number: 20090216053Abstract: 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: ApplicationFiled: April 25, 2007Publication date: August 27, 2009Applicant: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi
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Publication number: 20080300432Abstract: 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: ApplicationFiled: August 26, 2005Publication date: December 4, 2008Inventors: Vicki Hedrick, Stephan Brandstadter, Janet Boggs, Mitchel Cohn, Venkat Reddy Ghojala, P.V. Ramachandran
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Patent number: 7358405Abstract: 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: GrantFiled: May 3, 2006Date of Patent: April 15, 2008Assignee: Solvay Solexis SpAInventors: Ivan Wlassics, Vito Tortelli
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Patent number: 7345209Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene that comprises, in one preferred embodiment, providing a compound of the formula CF3CH2CHFX, wherein X is a selected from the group consisting of chlorine, bromine and iodine, and exposing said compound to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene. Other processes for forming 1,3,3,3-tetrafluoropropene are also disclosed.Type: GrantFiled: April 29, 2005Date of Patent: March 18, 2008Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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Patent number: 7271301Abstract: 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: GrantFiled: February 22, 2006Date of Patent: September 18, 2007Assignee: E.I. du Pont de Nemours and CompanyInventors: Peter Gideon Gelblum, Norman Herron, Charles Joseph Noelke, Velliyur Nott Mallikarjuna Rao
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Patent number: 7164050Abstract: 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: GrantFiled: May 2, 2005Date of Patent: January 16, 2007Assignee: Honeywell International Inc.Inventors: Stephen A. Cottrell, William R. Jones
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Patent number: 6992038Abstract: 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: GrantFiled: November 18, 2003Date of Patent: January 31, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Mitsuo Narita, Masaki Tabata, Kazuhisa Hayakawa
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Patent number: 6610896Abstract: 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: GrantFiled: July 5, 2002Date of Patent: August 26, 2003Assignee: Daikin Industries, Ltd.Inventors: Jun Miki, Hitoshi Yoshimi, Hirokazu Aoyama
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Publication number: 20030100806Abstract: 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: ApplicationFiled: December 30, 2002Publication date: May 29, 2003Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
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Patent number: 6534456Abstract: 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: GrantFiled: January 23, 2001Date of Patent: March 18, 2003Assignee: Unilever Home and Personal Care USA, division of Conopco, Inc.Inventors: Christine Hayward, Rosa Paredes
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Publication number: 20020193643Abstract: A process for preparing a perfluoroalkadiene compound of formula (I)Type: ApplicationFiled: July 5, 2002Publication date: December 19, 2002Inventors: Jun Miki, Hitoshi Yoshimi, Hirokazu Aoyama
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Patent number: 6369284Abstract: 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: GrantFiled: July 26, 1999Date of Patent: April 9, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, V.N.Mallikarjuna Rao
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Patent number: 6262321Abstract: 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: GrantFiled: May 18, 1999Date of Patent: July 17, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao
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Patent number: 6166156Abstract: 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: GrantFiled: November 12, 1998Date of Patent: December 26, 2000Inventors: Chengjiu Wu, Baopei Xu, James T. Yardley
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Patent number: 6093859Abstract: 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: GrantFiled: June 1, 1999Date of Patent: July 25, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 6018083Abstract: 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: GrantFiled: April 1, 1999Date of Patent: January 25, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: William H. Manogue, Mario Joseph Nappa, Allen Capron Sievert, V. N. Mallikarjuna Rao
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Patent number: 5914423Abstract: 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: GrantFiled: November 24, 1997Date of Patent: June 22, 1999Assignee: Zeneca, LimitedInventors: Michael Drysdale Turnbull, Nigel James Willetts, Steven Fitzjohn, Prafula Govind Kholia, Harjindersingh Bansal, Alfred Glyn Williams
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Patent number: 5880315Abstract: 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: GrantFiled: November 4, 1997Date of Patent: March 9, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: V.N. Mallikarjuna Rao, Munirpallam A. Subramanian
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Patent number: 5856593Abstract: 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: GrantFiled: February 4, 1997Date of Patent: January 5, 1999Assignee: Imperial Chemical Industries PLCInventors: Richard Llewellyn Powell, Andrew Paul Sharratt
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Patent number: 5728903Abstract: 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: GrantFiled: January 6, 1997Date of Patent: March 17, 1998Assignee: Asahi Glass Company Ltd.Inventors: Yutaka Furukawa, Mami Kotera, Seisaku Kumai, Kazuya Oharu, Toshihiko Toma