Catalyst Utilized Patents (Class 570/156)
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PROCESSES FOR THE SYNTHESIS OF 2-CHLORO-1,1,1,3,3,4,4,4-HEPTAFLUORO-2-BUTENE AND HEXAFLUORO-2-BUTYNE
Publication number: 20090156869Abstract: 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: ApplicationFiled: December 15, 2008Publication date: June 18, 2009Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventor: Mario Joseph Nappa -
Publication number: 20090143604Abstract: 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: ApplicationFiled: November 20, 2008Publication date: June 4, 2009Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
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Publication number: 20090127496Abstract: 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: ApplicationFiled: June 22, 2007Publication date: May 21, 2009Inventors: Velliyur Nott Mallikarjuna Rao, Mario Joseph Nappa, Allen Capron Sievert
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Publication number: 20090118554Abstract: 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: ApplicationFiled: August 4, 2006Publication date: May 7, 2009Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
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Publication number: 20090099395Abstract: 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: ApplicationFiled: December 12, 2008Publication date: April 16, 2009Applicant: CENTRAL GLASS COMPANY, LIMITEDInventors: Fuyuhiko Sakyu, Yasuo Hibino
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Publication number: 20090088593Abstract: 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: ApplicationFiled: September 28, 2007Publication date: April 2, 2009Applicant: Honeywell International Inc.Inventors: Hsueh Sung Tung, Rajiv R. Singh, Michael Van Der Puy
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Patent number: 7504547Abstract: 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: GrantFiled: May 2, 2007Date of Patent: March 17, 2009Assignee: Foosung Co., Ltd.Inventors: Hae-Seok Ji, Ook-Jae Cho, Jae-Gug Ryu, Young-Hoon Ahn, Bong-Suk Kim, Dong-Hyun Kim
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Publication number: 20090043138Abstract: 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: ApplicationFiled: August 4, 2006Publication date: February 12, 2009Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
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Patent number: 7485760Abstract: 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: GrantFiled: January 24, 2007Date of Patent: February 3, 2009Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
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Patent number: 7482499Abstract: 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: GrantFiled: April 28, 2004Date of Patent: January 27, 2009Assignee: Central Glass Company, LimitedInventors: Adam C. Alty, Richard A. Du Boisson
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Publication number: 20090018375Abstract: 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: ApplicationFiled: March 29, 2007Publication date: January 15, 2009Inventor: Mario Joseph Nappa
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Patent number: 7473810Abstract: 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: GrantFiled: October 12, 2007Date of Patent: January 6, 2009Assignee: Honeywell International Inc.Inventors: Michael Van Der Puy, Jingji Ma
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Patent number: 7470827Abstract: 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: GrantFiled: June 3, 2005Date of Patent: December 30, 2008Assignee: PPG Industries Ohio, Inc.Inventors: Yurii Oleksiyovych Serhuchev, Yurii Vasyliyovych Bilokopytov, Igorlvanovych Chernobaev
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Publication number: 20080207962Abstract: 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: ApplicationFiled: February 21, 2008Publication date: August 28, 2008Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Publication number: 20080207963Abstract: 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: ApplicationFiled: February 21, 2008Publication date: August 28, 2008Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 7396965Abstract: 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: GrantFiled: May 12, 2005Date of Patent: July 8, 2008Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, HsuehSung Tung, Haridasan Nair, Jingji Ma
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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: 7348461Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.Type: GrantFiled: October 31, 2003Date of Patent: March 25, 2008Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
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Patent number: 7345209Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene that comprises, in one preferred embodiment, providing a compound of the formula CF3CH2CHFX, wherein X is a selected from the group consisting of chlorine, bromine and iodine, and exposing said compound to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene. Other processes for forming 1,3,3,3-tetrafluoropropene are also disclosed.Type: GrantFiled: April 29, 2005Date of Patent: March 18, 2008Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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Publication number: 20080051610Abstract: 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: ApplicationFiled: January 24, 2007Publication date: February 28, 2008Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
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Patent number: 7329786Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.Type: GrantFiled: September 28, 2001Date of Patent: February 12, 2008Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Chengping Chien, Julie Sacarias, Vimal Sharma
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Patent number: 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: 7268261Abstract: 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: GrantFiled: August 31, 2005Date of Patent: September 11, 2007Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Vicki Hedrick, Stephen M. Brandstadter, Mitchel Cohn
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Patent number: 7250540Abstract: 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: GrantFiled: June 29, 2005Date of Patent: July 31, 2007Assignee: 3M Innovative Properties CompanyInventors: Gerald L. Bauer, Jeffrey D. Weigelt, Klaus Hintzer, Gernot Loehr, Werner Schwertfeger, Arthur A. Ponelis
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Patent number: 7241928Abstract: 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: GrantFiled: October 1, 2004Date of Patent: July 10, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur N.Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 7183448Abstract: A mixture comprising at least 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene is subjected to a distillation operation, and thereby, a distillate comprising an azeotropic composition consisting substantially of 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene is obtained and a bottom product comprising 1,1,1,3,3-pentafluoropropane or 1,1,1-trifluoro-3-chloro-2-propene which each is separated and purified.Type: GrantFiled: November 10, 1999Date of Patent: February 27, 2007Assignee: Daikin Industries, Ltd.Inventors: Tatsuo Nakada, Masayoshi Imoto, Takashi Shibanuma
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Patent number: 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: 7030283Abstract: 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: GrantFiled: January 23, 2004Date of Patent: April 18, 2006Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Kathryn Sue Hayes, Guido Peter Pez
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Patent number: 6963016Abstract: 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: GrantFiled: August 29, 2003Date of Patent: November 8, 2005Assignee: Council of Scientific and Industrial ResearchInventors: Janmanchi K. Murthy, Sridara C. Shekar, Kamaraju S. Ramarao, Burri D. Raju, Kondapuram Vijaya Raghavan
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Patent number: 6703533Abstract: 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: GrantFiled: November 21, 2001Date of Patent: March 9, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Gennadii Gerskovich Belen'Kii, Viacheslav Alexandrovich Petrov, Sergei Arnol'Dovich Postovoi, Paul Raphael Resnick, Yurii Vilovich Zeifman
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Patent number: 6683226Abstract: 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: GrantFiled: February 14, 2003Date of Patent: January 27, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Allen Capron Sievert, V. N. Mallikarjuna Rao
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Patent number: 6583328Abstract: 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: GrantFiled: April 5, 1999Date of Patent: June 24, 2003Assignee: PCBU Services, Inc.Inventors: John Cheng-Ping Qian, Julia Ann Sacarias
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Patent number: 6476281Abstract: 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: GrantFiled: July 26, 2001Date of Patent: November 5, 2002Assignee: PCBU Services, Inc.Inventors: John Cheng-Ping Qian, Julia Ann Sacarias
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Publication number: 20020151755Abstract: 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: ApplicationFiled: February 12, 2002Publication date: October 17, 2002Applicant: Ausimont S.p.A.Inventors: Paolo Cuzzato, Letanzio Bragante
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Publication number: 20020115895Abstract: 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: ApplicationFiled: January 30, 2002Publication date: August 22, 2002Inventors: William H. Manogue, V.N. Mallikarjuna Rao, Allen Capron Sievert, Steven H. Swearingen
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Patent number: 6403847Abstract: 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: GrantFiled: March 20, 2001Date of Patent: June 11, 2002Assignee: Daikin Industries Ltd.Inventors: Tatsuo Nakada, Takashi Shibanuma, Noriaki Shibata
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Patent number: 6380446Abstract: 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: GrantFiled: March 7, 2001Date of Patent: April 30, 2002Assignee: DuPont Dow Elastomers, L.L.C.Inventors: David William Drew, Terry Wayne Redwine
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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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Publication number: 20020035300Abstract: 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: ApplicationFiled: August 19, 1999Publication date: March 21, 2002Inventors: V.N. MALLIKARJUNA RAO, ALLEN CAPRON SIEVERT
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Patent number: 6359183Abstract: 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: GrantFiled: December 1, 1999Date of Patent: March 19, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Frank J. Christoph, George W. Coulston, Velliyur Nott 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: 6235951Abstract: 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: GrantFiled: November 20, 1996Date of Patent: May 22, 2001Assignee: Central Glass Company, LimitedInventors: Fuyuhiko Sakyu, Satoshi Yoshikawa, Yasuo Hibino, Yoshihiko Gotoh, Ryouichi Tamai
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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: 6124510Abstract: Preparation of cis/trans 1234ze monomer is provided, by dehydrofluorination of 245fa using an alkaline solution or using a gas phase catalyzed process.Type: GrantFiled: July 21, 1998Date of Patent: September 26, 2000Assignee: Elf Atochem North America, Inc.Inventors: Maher Y. Elsheikh, Paul D. Fellenger
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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: 6034289Abstract: 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: GrantFiled: December 3, 1997Date of Patent: March 7, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Frank J. Christoph, George W. Coulston, Velliyur Nott Mallikarjuna Rao
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Patent number: 6031141Abstract: 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: GrantFiled: August 6, 1998Date of Patent: February 29, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Rao V.N. Mallikarjuna, Munirpallam A. Subramanian
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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: 5986151Abstract: 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: GrantFiled: August 28, 1998Date of Patent: November 16, 1999Assignee: AlliedSignal Inc.Inventor: Michael Van Der Puy
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Patent number: 5945573Abstract: 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: GrantFiled: January 9, 1998Date of Patent: August 31, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao, Allen Capron Sievert