Increasing The Number Of Carbon Atoms In The Compound Patents (Class 570/171)
  • Patent number: 11878290
    Abstract: Disclosed is a method for reducing carbon deposits on a catalyst in recycling HFC-23. The recycling is realized by means of a fluorine-chlorine exchange reaction with HFC-23 and a halogenated hydrocarbon. The catalyst for the fluorine-chlorine exchange reaction comprises a main body catalyst and a precious metal. The precious metal is selected from at least one of Pt, Pd, Ru, Au or Rh, and has an addition amount of 0.01-2 wt %. During the fluorine-chlorine exchange reaction, hydrogen gas is introduced. The invention has advantages of good catalyst stability, long life, etc.
    Type: Grant
    Filed: February 24, 2020
    Date of Patent: January 23, 2024
    Assignees: SINOCHEM LANTIAN CO., LTD., ZHEJIANG LANTIAN ENVIRONMENTAL PROTECTION HI-TECH CO., LTD., ZHEJIANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.
    Inventors: Jianjun Zhang, Wenfeng Han, Shucheng Wang, Wucan Liu, Feixiang Zhou
  • Patent number: 11655199
    Abstract: A halogenated alkene compound and a fluorinated alkyne compound are obtained at a high conversion rate and high selectivity by employing any of the following methods (1) to (4): (1) a halogenated butane compound represented by CX1X2X3CHX4CFHCX5X6X7, wherein X1, X2, X3, X4, X5, X6, and X7 are the same or different and each is a halogen atom, to a dehydrofluorination reaction; (2) a halogenated butene compound represented by CX1X2X3CX4?CHCX5X6X7, wherein X1, X2, X3, X4, X5, X6, and X7 are as defined above, to a dehydrohalogenation reaction; (3) a halogenated alkane compound represented by CHX8A1CHX9A2, wherein A1 and A2 are each a fluorine atom or a perfluoroalkyl group, and X8 and X9 are the same or different and each is a halogen atom, to a dehydrohalogenation reaction in the presence of a catalyst in a gas phase; and (4) a halogenated alkene compound represented by CX8A1=CHA2, wherein A1, A2, and X8 are as defined above, to a dehydrohalogenation reaction in the presence of a catalyst.
    Type: Grant
    Filed: August 20, 2021
    Date of Patent: May 23, 2023
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Yuusuke Etou, Shingo Nakamura
  • Patent number: 8957264
    Abstract: A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.
    Type: Grant
    Filed: December 11, 2013
    Date of Patent: February 17, 2015
    Assignee: Asahi Glass Company, Limited
    Inventors: Shoji Furuta, Yusuke Sugahara, Keiko Nakase, Keisuke Mori
  • Patent number: 8889924
    Abstract: The present invention provides a simple three step process for the production of 1,3,3,3-tetrafluoropropene (HFO-1234ze). In the first step, carbon tetrachloride is added to vinyl fluoride to afford the compound CCl3CH2CHClF (HCFC-241fb). HCFC-241fb is then fluorinated with anhydrous HF to afford CF3CH2CHClF (HCFC-244fa) in the second step. Dehydrochlorination of HCFC-244fa, in the third step, affords the desired product, CF3CH?CHF (HFO-1234ze). Following similar chemistry, vinyl chloride may be used in place of vinyl fluoride.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv Ratna Singh, Andrew Joseph Poss, David Nalewajek
  • Patent number: 8809218
    Abstract: There is provided a substance having much higher catalytic activity for a Suzuki-Miyaura coupling reaction than conventional heterogenous catalysts. The present invention provides a zeolite-palladium complex including USY-zeolite and Pd supported on the USY-zeolite, the Pd having a Pd—Pd coordination number of 4 or less and an oxidation number of 0.5 or less.
    Type: Grant
    Filed: February 23, 2010
    Date of Patent: August 19, 2014
    Assignee: National University Corporation Tottori University
    Inventors: Kazu Okumura, Miki Niwa, Hirosuke Matsui, Yoshinori Enmi, Takuya Tomiyama, Shizuyo Okuda
  • Patent number: 8791310
    Abstract: To provide a process for producing a fluoroalkyl iodide, whereby the selectivity for a fluoroalkyl iodide having a desired degree of polymerization is high and the productivity is high. A process for producing a fluoroalkyl iodide (2) represented by RfCF2CF2I (wherein Rf is a fluoroalkyl group having at most 4 carbon atoms), which comprises reacting a fluoroalkyl iodide (1) represented by RfI with tetrafluoroethylene in the presence of a radical initiator, wherein a first reaction step of supplying and reacting tetrafluoroethylene and a radical initiator to the fluoroalkyl iodide (1), is followed by repeating (n?1) times (provided that n is an integer of at least 3) a subsequent reaction step of supplying and reacting a radical initiator, or a radical initiator and tetrafluoroethylene, to a reaction mixture (1) formed in the first reaction step.
    Type: Grant
    Filed: December 4, 2012
    Date of Patent: July 29, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Tetsuo Otsuka, Shoji Furuta
  • Patent number: 8729321
    Abstract: A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state is under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.
    Type: Grant
    Filed: April 19, 2006
    Date of Patent: May 20, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Shoji Furuta, Yu{grave over (s)}uke Sugahara, Keiko Nakase, Keisuke Mori
  • Patent number: 8461401
    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: Grant
    Filed: March 11, 2011
    Date of Patent: June 11, 2013
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Haiyou Wang
  • Patent number: 8426655
    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: Grant
    Filed: March 11, 2011
    Date of Patent: April 23, 2013
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Haiyou Wang
  • Patent number: 8299309
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF?CHR from halofluorocarbons of the structure RfCFX2. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(?O)R?.
    Type: Grant
    Filed: October 11, 2011
    Date of Patent: October 30, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Patent number: 8247625
    Abstract: A process is disclosed for making RR1R2CCR1R2F wherein R is selected from the group consisting of CH3, CH2F, C2H4F, and F(CF2)nCH2CH2 where n is an integer from 1 to 10, each R1 is independently selected from the group consisting of H, Cl, F and CF3, and each R2 is independently selected from the group consisting of H, F and CF3. The process involves reacting RF with R1R2C?CR1R2 in the presence of SbF5 to produce a product mixture comprising RR1R2CCR1R2F, wherein the reaction temperature is from about ?60° C. to about ?10° C., provided that total number of carbon atoms in R1R2C?CR1R2 is 5 or less.
    Type: Grant
    Filed: July 3, 2007
    Date of Patent: August 21, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Xuehui Sun, Viacheslav A. Petrov, Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Ekaterina N. Swearingen
  • Patent number: 8236425
    Abstract: A composition comprises a distribution of telomers of ethylene and at least one fluoroalkyl or perfluoroalkyl halide, the telomers comprising at least one polymethylene segment (—(CH2)n—) and at least one halomethyl group (—CXH2) and optionally comprising at least one non-fluorine heteroatom, and the halogen being selected from iodine and bromine; wherein the distribution has a number average ratio of methylene moieties of the polymethylene segment to the halomethyl groups of at least about 15.
    Type: Grant
    Filed: December 27, 2007
    Date of Patent: August 7, 2012
    Assignee: 3M Innovative Properties Company
    Inventors: George G. I. Moore, Yu Yang, Richard M. Flynn
  • Publication number: 20120065436
    Abstract: The present invention provides a process for preparing a fluorine-containing propane represented by the formula: CF2XCF2CH3 wherein X is F or Cl, the process including reacting tetrafluoroethylene and methyl chloride in the presence of an antimony halide represented by the formula: SbFxC5-x wherein x is a value of 0 to 5. According to the present invention, the fluorine-containing propane represented by the formula: CF2XCF2CH3 wherein X is F or Cl, which is useful as a starting material of 2,3,3,3-tetrafluoropropene (1234yf), can be obtained by a simple process, using relatively inexpensive starting materials.
    Type: Application
    Filed: May 11, 2010
    Publication date: March 15, 2012
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Daisuke Karube, Tsuneo Yamashita, Akinarri Sugiyama, Takashi Shibanuma
  • Patent number: 8058488
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol.
    Type: Grant
    Filed: November 20, 2008
    Date of Patent: November 15, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Patent number: 7951982
    Abstract: Disclosed is a process for the preparation of fluorinated olefins. In preferred embodiments C3 olefins are produced by methods comprising contacting a compound of the Formula (I) C(R1aR2bR3c)??(I) with a compound of Formula (II) C(R1aR2bR3c)Cn(R1aR2bR3c)??II wherein R1a, R2b, and R3c are independently a hydrogen atom or a halogen selected from the group consisting of fluorine; chlorine, bromine and iodine, provided that the compound of formula I has at least three halogen substituents and that said at three halogen substituents comprise at least one fluorine; a, b and c are independently=0, 1, 2 or 3 and (a+b+c)=2 or 3; and n is 0 or 1, under conditions effective to produce at least one C3 fluoroolefin.
    Type: Grant
    Filed: November 3, 2006
    Date of Patent: May 31, 2011
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy, Robert C. Johnson, Daniel C. Merkel
  • Publication number: 20090253929
    Abstract: The present invention concerns a compound of formula (I): wherein R1 is C1-4 alkyl, or benzyl optionally substituted by halogen, C1-4alkyl (optionally substituted by halogen or C1-4 alkoxy), C1-4 alkoxy, C1-4 alkoxycarbonyl, nitro or cyano; and a process for preparing a compound of formula (I).
    Type: Application
    Filed: December 7, 2005
    Publication date: October 8, 2009
    Applicant: ASTRAZENECA AB
    Inventors: Allison Noble, Matthew Perry
  • Publication number: 20090143604
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol.
    Type: Application
    Filed: November 20, 2008
    Publication date: June 4, 2009
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Patent number: 7498468
    Abstract: 4-Aminopicolinic acids having tri- and tetra-substituted aryl substituents in the 6-position, and their amine and acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control.
    Type: Grant
    Filed: October 4, 2007
    Date of Patent: March 3, 2009
    Assignee: Dow AgroSciences LLC
    Inventors: Terry W. Balko, John F. Daeuble, Thomas L. Siddall
  • Patent number: 7371904
    Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene which comprises, in one embodiment, reacting a compound of CF3X1 with a compound of CX2H?CHX3, wherein X1, X2, and X3 are each independently selected from the group consisting of fluorine, chlorine, bromine and iodine, to produce a reaction product comprising a compound of CF3CH?CHX3, wherein X3 is as described above; and when X3 is not fluorine, fluorinating the compound to produce 1,3,3,3-tetrafluoropropene. The process in another embodiment comprises preparing tetrafluoropropene comprising thermally cracking one or more compounds capable of producing a reaction mixture which preferably comprises diflurocarbene radicals and vinylidene fluoride, and converting said reaction mixture into—tetrafluoropropene (1,3,3,3-tetrafluoropropene).
    Type: Grant
    Filed: April 29, 2005
    Date of Patent: May 13, 2008
    Assignee: Honeywell International Inc.
    Inventors: Jing Ji Ma, Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
  • Patent number: 7364908
    Abstract: A method of separating at least a first non-fluorous compound from a mixture of compounds including at least the first non-fluorous compound and a second fluorous compound includes: charging the of compounds to a non-fluorous solid (stationary) phase and eluting with a fluorous eluting fluid (mobile phase). In one embodiment, the non-fluorous solid phase is polar in nature. The method can further include a second phase elution with a suitable organic solvent. A method conducting a chemical reaction, includes: mixing at least a first fluorous compound and a second compound, the first fluorous compound differing in fluorous nature from the second compound; exposing the first mixture to conditions to convert at least one of the first fluorous compound and the second compound to give a second mixture containing at least a third compound, charging the second mixture to a non-fluorous solid phase; and eluting with a fluorous fluid.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: April 29, 2008
    Assignees: University of Pittsburgh - Of the Commonwealth System of Higher Education, Fluorous Technologies Inc.
    Inventors: Dennis P. Curran, Masato Matsugi, Marvin S. Yu
  • Patent number: 7230147
    Abstract: The invention concerns a method for functionalizing a double bond and, more particularly, a double bond bearing a metalloid atom. Said functionalization is produced by the action of perhalogenated sulphonyl chloride on the carbon bearing sulphur in the presence of a free radical initiator, preferably by homolytic cleavage. The invention is useful in organic synthesis.
    Type: Grant
    Filed: June 11, 2004
    Date of Patent: June 12, 2007
    Assignee: Shasun Pharma Solutions Limited
    Inventor: Nicolas Roques
  • Patent number: 7208645
    Abstract: The present invention provides a process for producing 4-(2-methylphenyl)benzotrifluoride, comprising reacting 4-chlorobenzotrifluoride with 2-methylphenylmagnesium chloride in the presence of cobalt-based catalyst and zinc salt.
    Type: Grant
    Filed: March 9, 2006
    Date of Patent: April 24, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kiyoshi Sugi, Masahide Tanaka
  • Patent number: 7102041
    Abstract: A process for preparing a haloalkane comprising: (a) contacting a haloalkane starting material with an alkene in the presence of an effective amount of a catalyst complex under conditions effective to facilitate an addition reaction and to form a product stream comprising a haloalkane product from the addition reaction, wherein the catalyst complex has a boiling point higher than that of the haloalkane product; and (b) recovering the haloalkane product from the product stream.
    Type: Grant
    Filed: December 8, 2004
    Date of Patent: September 5, 2006
    Assignee: Honeywell International Inc.
    Inventor: Hsueh Sung Tung
  • Patent number: 7094936
    Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: August 22, 2006
    Assignee: Great Lakes Chemical Corporation
    Inventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
  • Patent number: 7053253
    Abstract: Perfluoro-4-methyl-2-pentene containing the undesirable perfluoro-2-methyl-2-pentene may be purified by contacting the mixture with at least a stoichiometric equivalent of an aqueous inorganic base (relative to the perfluoro-2-methyl-2-pentene), in the presence of a polar solvent.
    Type: Grant
    Filed: May 2, 2005
    Date of Patent: May 30, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Zhongxing Zhang, Zai-Ming Qiu
  • Patent number: 6992229
    Abstract: The present invention has an object to provide a method for purifying a fluorinated hydroxyl compound of the formula 1 safely in a high yield under industrially practical conditions. Namely, a mixture containing a fluorinated hydroxyl compound of Rf—CR1R2—OH (Formula 1, wherein Rf is a C1-20 polyfluoroalkyl group, and each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group) such as 2,2,3,3-tetrafluoropropanol, and a compound having an unshared electron pair, is distilled by heating in the presence of a solid acid catalyst such as a cation exchange resin catalyst, or by adding a proton source such as water.
    Type: Grant
    Filed: November 19, 2002
    Date of Patent: January 31, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Hidekazu Okamoto, Akihiro Wada, Toshihiko Toma, Nobuyuki Yamagishi
  • Patent number: 6958422
    Abstract: The present invention relates to the pyrolysis of hydrochlorofluorocarbons to form fluoromonomers such as tetrafluoroethylene, the pyrolysis being carried out in a reaction zone lined with nickel and mechanically supported by a jacket of other corrosion resistant metal, the nickel lining providing an improved yield of valuable reaction products.
    Type: Grant
    Filed: December 17, 2003
    Date of Patent: October 25, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Charles Joseph Noelke, Velliyur Nott Mallikarjuna Rao
  • Patent number: 6924403
    Abstract: The present invention relates to the process of pyrolyzing tetrafluoroethylene to hexafluoropropylene by carrying out the pyrolysis in a tubular reactor that is lined with either nickel or nickel alloy which contains no greater than 8 wt % chromium.
    Type: Grant
    Filed: May 7, 2003
    Date of Patent: August 2, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: John James Barnes, Kenneth Paul Kelch, Thomas D. Sandbrook, David John Van Bramer
  • Patent number: 6919490
    Abstract: The present invention relates to a process for continuously producing a perfluoroalkyl iodide represented by the general formula Rf(CF2CF2)nI, wherein Rf is a C1-6 perfluoroalkyl and n is an integer from 1 to 4, the method comprising continuously supplying a perfluoroalkyl iodide as a telogen represented by the general formula RfI, wherein Rf is as defined above, and tetrafluoroethylene as a taxogen to a tubular reactor packed with a metal catalyst comprising a powdery spherical metal or a sintered metal; and conducting telomerization at a temperature of 60 to 160° C. under a pressure of 0.1 to 5 MPa (gauge pressure). According to the present invention, medium-chain perfluoroalkyl iodides can be continuously and efficiently produced with little generation of impurities, such as hydrogen-containing organic compounds and the like.
    Type: Grant
    Filed: April 17, 2002
    Date of Patent: July 19, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshio Funakoshi, Jun Miki
  • Patent number: 6858763
    Abstract: The present invention relates to a process for preparing an elastomeric ethylene-hexafluoropropylene copolymer with excellent vulcanization properties, which comprises emulsion polymerizing ethylene, hexafluoropropylene and when in demand, a monomer copolymerizable therewith in a aqueous medium at a low temperature of ?20° C. to 40° C. using a radical polymerization initiator.
    Type: Grant
    Filed: September 19, 2001
    Date of Patent: February 22, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Mitsuo Tsukamoto, Masao Otsuka, Mitsuhiro Otani, Tatsuya Morikawa, Hideya Saito
  • Patent number: 6844474
    Abstract: The present invention provides a vapor phase process for the production of difluoromethane, HFC-32. The process of this invention provides for the preparation of HFC-32 by a process that exhibits both good product yield and selectivity.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: January 18, 2005
    Assignee: Allied Signal Inc.
    Inventors: Paul Gene Clemmer, Addison Miles Smith, Hsueh Sung Tung, John Stephen Bass
  • Patent number: 6825043
    Abstract: A method of increasing the fluorous nature of a compound includes the step of reacting the compound with at least one second compound having the formula: wherein Rf is a fluorous group, Rs is a spacer group, d is 1 or 0, m is 1, 2 or 3, Ra is an alkyl group and X is a suitable leaving group. A compound has the formula: wherein Rf is a fluorous group, n is an integer between 0 and 6, m is 1, 2 or 3, Ra is an alkyl group and X is a leaving group.
    Type: Grant
    Filed: May 5, 2000
    Date of Patent: November 30, 2004
    Assignee: University of Pittsburgh
    Inventors: Dennis P. Curran, Roger Read, Zhiyong Luo
  • Publication number: 20040225166
    Abstract: A continuous process is provided for the manufacture of haloalkanes by the reaction of carbon tetrachloride with olefins in the presence of iron metal, trialkylphosphate, and ferric chloride. A fraction of the catalyst and co-catalyst are separated after the reaction and recycled. In a preferred application, the olefin is ethene, and the haloalkane product is 1,1,1,3-tetrachloropropane. Two distillation steps take place in order to enhance the production of 1,1,1,3-tetrachloropropane.
    Type: Application
    Filed: August 26, 2003
    Publication date: November 11, 2004
    Applicant: VULCAN CHEMICALS A BUSINESS GROUP OF VULCAN MATERIALS COMPANY
    Inventors: Richard L. Wilson, John L. Dawkins
  • Patent number: 6806396
    Abstract: The present invention relates to the co-pyrolysis of fluoroform and chlorodifluoromethane to form a mixture of useful fluoroolefin and saturated HFCs, notably, tetrafluoroethylene and hexafluoropropylene and CF3CHF2 and CF3CHFCF3, respectively.
    Type: Grant
    Filed: December 16, 2002
    Date of Patent: October 19, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Peter Gideon Gelblum, Velliyur Nott Mallikarjuna Rao, Charles Joseph Noelke, Norman Herron
  • Publication number: 20040082822
    Abstract: The present invention relates to a process for simultaneously preparing tetrafluoroethylene and hexafluoropropylene by the pyrolysis of difluorochloromethane mixed in the molar ratio of super-heated steam/pre-heated difluorochloromethane ([H2O]/[R22]) of 5-10 under the conditions such as a temperature of 730° C. to 760° C. and a residence time of 0.01 to 0.2 seconds, where the unreacted R22 and produced HFP are recycled and controlled to have an appropriate molar ratio of HFP/R22 of 0.01 to 0.1 in order to obtain a high yield of HFP. Thus, the pyrolysis process of the present invention is efficient for preparing TFE and HFP, which are essential monomers in fluorinated resin industry.
    Type: Application
    Filed: April 16, 2003
    Publication date: April 29, 2004
    Inventors: Dong Ju Moon, Jung Jo Jung, Yong Joon Lee, Sang Deuk Lee, Byoung Sung Ahn
  • Publication number: 20040073032
    Abstract: A process for preparing compounds of the formula (II), 1
    Type: Application
    Filed: October 2, 2003
    Publication date: April 15, 2004
    Applicant: Clariant GmbH
    Inventors: Andreas Meudt, Michael Erbes, Klaus Forstinger
  • Publication number: 20040049089
    Abstract: A mixture of fluoroalkyl iodide telomers represented by the formula: Rf(CF2CF2)nI wherein Rf represents a fluoroalkyl group whose number of carbon atoms is in the range of 1 to 10, with the polymerization degree n equal to or more than k that is an integer of 3 or more, is obtained by reacting a fluoroalkyl iodide with tetrafluoroethylene in a first reactor followed by fractionating a first reaction mixture which contains fluoroalkyl iodide telomers of low polymerization degree, as well as by reacting the telomer with n of (k−1) separated from the first reaction mixture with tetrafluoroethylene in the second reactor.
    Type: Application
    Filed: July 18, 2003
    Publication date: March 11, 2004
    Inventors: Yukio Homoto, Kunitada Tanaka
  • Publication number: 20040002621
    Abstract: The present invention relates to the process of pyrolyzing tetrafluoroethylene to hexafluoropropylene by carrying out the pyrolysis in a tubular reactor that is lined with either nickel or nickel alloy which contains no greater than 8 wt % chromium.
    Type: Application
    Filed: May 7, 2003
    Publication date: January 1, 2004
    Inventors: John James Barnes, Kenneth Paul Kelch, Thomas D. Sandbrook, David John Van Bramer
  • Publication number: 20030166981
    Abstract: The present invention relates to the co-pyrolysis of fluoroform and chlorodifluoromethane to form a mixture of useful fluoroolefin and saturated HFCs, notably, tetrafluoroethylene and hexafluoropropylene and CF3CHF2 and CF3CHFCF3, respectively.
    Type: Application
    Filed: December 16, 2002
    Publication date: September 4, 2003
    Inventors: Peter Gideon Gelblum, Velliyur Nott Mallikarjuna Rao, Charles Joseph Noelke, Norman Herron
  • Patent number: 6548712
    Abstract: The invention relates to a process for producing 1,1,1,5,5,5-hexafluoroacetylacetone. This process includes (a) hydrolyzing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone into a 1,1,1,5,5,5-hexafluoroacetylacetone hydrate; and (b) dehydrating the hydrate into the 1,1,1,5,5,5-hexafluoroacetylacetone with high purity from a material containing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone.
    Type: Grant
    Filed: March 15, 2001
    Date of Patent: April 15, 2003
    Assignee: Central Glass Company, Limited
    Inventors: Takeo Komata, Nariaki II
  • Patent number: 6518467
    Abstract: A method of producing hydrofluorocarbons and/or hydrochlorofluorocarbons by using halogenated alkanes as a principal reactant. Generally, the method comprises the step of: (a) reacting a starting halogenated alkane corresponding to the formula (I): H3C—CX3  (I) wherein X is independently fluorine or chlorine, with a hydrohalocarbon adduct in the presence of a catalyst to form a hydrofluorocarbon and/or hydrochlorofluorocarbon.
    Type: Grant
    Filed: December 29, 2000
    Date of Patent: February 11, 2003
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Michael Van Der Puy
  • Patent number: 6440892
    Abstract: The present invention provides a method and catalyst composition for carbonylating aromatic hydroxy compounds, comprising the step of contacting at least one aromatic hydroxy compound with oxygen and carbon monoxide in the presence of a carbonylation catalyst composition comprising an effective amount of at least one Group 8, 9, or 10 metal source, an effective amount of a combination of inorganic co-catalysts comprising at least one Group 4 metal source and at least one Group 11 metal source, an effective amount of at least one salt co-catalyst with an anion selected from the group consisting of carboxylate, benzoate, acetate, sulfate, and nitrate, wherein the carbonylation catalyst composition is free of a halide source.
    Type: Grant
    Filed: March 30, 2001
    Date of Patent: August 27, 2002
    Assignee: General Electric Company
    Inventors: Kirill Vladimirovich Shalyaev, Grigorii Lev Soloveichik, Donald Wayne Whisenhunt, Jr., Bruce Fletcher Johnson
  • Publication number: 20020087039
    Abstract: A method of producing hydrofluorocarbons and/or hydrochlorofluorocarbons by using halogenated alkanes as a principal reactant.
    Type: Application
    Filed: December 29, 2000
    Publication date: July 4, 2002
    Inventors: Hsueh Sung Tung, Michael Van Der Puy
  • Patent number: 6355849
    Abstract: The subject-matter of the present invention is a process of use in perfluoroalkylation and a reactant for making use of this process. This process is defined in that it comprises a stage in which a material of formula RfH and a base (or a species capable of generating a base) are brought into contact, in a polar and anhydrous medium, with a substrate carrying at least one electrophilic functional group. Application to organic synthesis.
    Type: Grant
    Filed: February 17, 2000
    Date of Patent: March 12, 2002
    Assignee: Rhodia Chimie
    Inventors: Nicolas Roques, James Russel
  • Patent number: 6348634
    Abstract: A reductive dimerization process of 1,1,1-trifluoro, 2,2,2-trichloroethane (CFC-113a) with hydrogen, with formation of 1,1,1,4,4,4-hexafluoro-2,2,3,3-tetrachlorobutane and 1,1,1,4,4,4-hexafluoro-2,2-dichlorobutene, and mixtures thereof, wherein the catalyst is constituted by metal ruthenium supported on graphitized carbon obtainable by treatment of the carbon at temperatures higher than 2000° C., in inert gas, or aluminum fluoride having an high surface area.
    Type: Grant
    Filed: February 2, 2000
    Date of Patent: February 19, 2002
    Assignee: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Ornella Majaron, Francesco Pinna
  • Patent number: 6156163
    Abstract: A reagent comprising a compound of formula (I): R.sub.f --M(X) (Z).sub.n --Y--R, wherein R is a hydrocarbon radical advantageously having at most 10 carbon atoms and being selected from alkyls and aryls; R.sub.f is a radical of formula II: R.sub.1 --(C.XI..sub.2).sub.m --CF.sub.2 --, where R.sub.1 is a fluorine or chlorine atom or a carbon radical, m is 0 or a integer from 0-12, and each .XI., which may be the same or different, is a chlorine or preferably fluorine atom, with the proviso that when m is 0, R.sub.1 is electroattractive, preferably a fluorine atom;n is 0 or 1; M is a non-metal selected from carbon and chalcogens with an atomic number higher than oxygen; and each of X, Y and Z, which are the same or different, is a chalcogen; as well as a generator, for consecutive or simultaneous addition. The reagent is useful for organic synthesis.
    Type: Grant
    Filed: November 6, 1997
    Date of Patent: December 5, 2000
    Assignee: Rhodia Chimie
    Inventors: Bernard Langlois, Nicolas Roques, Claude Wakselman, Marc Tordeux, Gerard Forat
  • Patent number: 6031141
    Abstract: This invention provides a process for the manufacture of a fluoroolefin of the formula (R.sup.1).sub.2 C.dbd.C(R.sup.1).sub.2 wherein each R.sup.1 is independently selected from the group consisting of --H, --F, --CF.sub.3, --CHF.sub.2, --CH.sub.2 F, --C.sub.2 F.sub.5, --C.sub.2 HF.sub.4 and --C.sub.2 H.sub.2 F.sub.3, provided that at least one R.sup.1 is not --H. The process comprises contacting a hydrofluorocarbon of the formula (R.sup.1).sub.2 CHCF(R.sup.1).sub.2 with a catalyst comprising cubic chromium trifluoride, i.e., a chromium trifluoride having an X-ray diffraction powder pattern shown in Table I, at a temperature of from about 200.degree. C. to about 500.degree. C.
    Type: Grant
    Filed: August 6, 1998
    Date of Patent: February 29, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rao V.N. Mallikarjuna, Munirpallam A. Subramanian
  • Patent number: 6025532
    Abstract: In order to manufacture pentafluoroethane (F125) and/or 1,1,1,2,3,3,3-haptafluoropropane (F227ea), a trifluoromethane gas stream is subjected to pyrolysis and then the mixture of gases which result from this pyrolysis is brought into contact with a fluorination catalyst.
    Type: Grant
    Filed: June 17, 1998
    Date of Patent: February 15, 2000
    Assignee: Elf Atochem S.A.
    Inventors: Jean-Marc Sage, Eric Lacroix, Philippe Bonnet, Eric Jorda
  • Patent number: 5750810
    Abstract: The present invention relates to the simultaneous manufacture of difluoromethane (F32) and 1,1,1,2-tetrafluoroethane (F134a) by pyrolysis of chlorodifluoromethane in the presence of hydrogen, working at a temperature above 500.degree. C. in the absence of any catalyst or metal surface. Depending on the operating conditions chosen, this process also makes it possible predominantly to manufacture either F134a or F32.
    Type: Grant
    Filed: July 30, 1997
    Date of Patent: May 12, 1998
    Assignee: Elf Atochem S.A.
    Inventors: Jean-Pierre Schirmann, Serge Hub, Andre Lantz
  • Patent number: 5536890
    Abstract: 1,1,1,4,4,4-hexafluorobutane is obtained from a trifluoroethane compound, by reacting this with hydrogen in the gas phase and without a diluent on a palladium- and/or nickel-containing supported catalyst and subsequently hydrogenating the reaction product.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: July 16, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Bielefeldt, Albrecht Marhold