Catalyst Utilized Patents (Class 570/156)
  • Patent number: 8455704
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ??(II) where Z is H, F, Cl, I or Br.
    Type: Grant
    Filed: November 2, 2011
    Date of Patent: June 4, 2013
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
  • Patent number: 8450537
    Abstract: A process is disclosed for making CF3CH2CHF2, CF3CH?CHF, and/or CF3CH?CHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX3CH?CH2 and halopropenes of the formula CX2?CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 in a reaction zone to produce a product mixture comprising HF, HCl, CF3CH2CHF2, CF3CH?CHF and CF3CH?CHCl; and recovering the CF3CH2CHF2, CF3CH?CHF, and/or CF3CH?CHCl from the product mixture. The molar ratio of HF to the total amount of starting materials fed to the reaction zone is at least stoichiometric, and the molar ratio of Cl2 to total amount of starting material fed to the reaction zone is 2:1 or less.
    Type: Grant
    Filed: October 23, 2012
    Date of Patent: May 28, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20130131402
    Abstract: A catalytic process for the synthesis of trifluoroethylene from chlorotrifluoroethylene which comprises contacting chlorotrifluoroethylene with hydrogen in the presence of a catalyst consisting of palladium or platinum supported on extruded activated carbon.
    Type: Application
    Filed: June 22, 2011
    Publication date: May 23, 2013
    Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Stefano Millefanti, Vito Tortelli, Giuseppe Marchionni
  • Patent number: 8436216
    Abstract: A process is disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent and 2,2?-bipyridine. A process is also disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent and a Cu(I) salt. A process is further disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent, 2,2?-bipyridine and a Cu(I) salt.
    Type: Grant
    Filed: March 18, 2009
    Date of Patent: May 7, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa, Win-Chung Lee
  • Publication number: 20130102814
    Abstract: A process is disclosed for making CF3CH2CHF2, CF3CH?CHF and/or CF3CH?CHCl. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHClCH2X, halopropenes of the formula CX3CCl?CH2 and halopropenes of the formula CX2?CClCH2X, wherein each X is independently F or Cl, with HF in a reaction zone to produce a product mixture comprising HF, HCl, CF3CH2CHF2, CF3CH?CHF and CF3CH?CHCl; and recovering the CF3CH2CHF2, CF3CH?CHF and/or CF3CH?CHCl from the product mixture. Also disclosed is a process for making CF3CF2CH3 and/or CF3CF?CH2.
    Type: Application
    Filed: November 29, 2012
    Publication date: April 25, 2013
    Applicant: E I Du Pont De Nemours and Company
    Inventor: E I Du Pont De Nemours and Company
  • Patent number: 8426656
    Abstract: The disclosed integrated manufacturing process includes a combined liquid phase reaction and purification operation which directly produces trans-1-chloro-3,3,3-trifluoropropene and 3-chloro-1,1,1,3-tetrafluoropropane which is a precursor to the manufacture of trans-1,3,3,3-tetrafluoropropene. The mixture of co-products is easily separated by conventional distillation and 3-chloro-1,1,1,3-tetrafluoropropane is then dehydrochlorinated to produce trans-1,3,3,3-tetrafluoropropene by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrochlorination catalyst.
    Type: Grant
    Filed: April 5, 2010
    Date of Patent: April 23, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Robert Johnson, Hsueh Sung Tung, Haiyou Wang, Konstantin A. Pokrovski
  • Patent number: 8420873
    Abstract: The present invention provides a process for producing 2,3,3,3-tetrafluoropropene including the step of dehydrofluorinating 1,1,1,2,3-pentafluoropropane, wherein 1,3,3,3-tetrafluoropropene and 1,1,3,3,3-pentafluoropropane are supplied together with 1,1,1,2,3-pentafluoropropane to a reactor containing a catalyst to simultaneously perform dehydrofluorination reaction and isomerization reaction. According to the process of the present invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be efficiently produced by effectively using the by-products of the dehydrofluorination reaction.
    Type: Grant
    Filed: August 20, 2009
    Date of Patent: April 16, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Kazuhiro Takahashi, Takehiro Chaki, Yuko Shiotani
  • Patent number: 8410325
    Abstract: The invention relates to a process for preparing a compound of formula CF3CF?CHX, CHX2CX?CX2 or a linear or branched C4-7 (hydro)fluoroalkene, wherein each X is, independently, H or F provided that in CHX2CX?CX2 at least one X is F, which process comprises dehydrohalogenating a compound of formula CF3CFYCH2X, CF3CFHCYHX, CHX2CXYCX2H, CHX2CXHCX2Y, or a linear or branched C4-7 hydro(halo)fluoroalkane, wherein each X is, independently, H or F provided that in CHX2CXYCX2H and CHX2CXHCX2Y at least one X is F, wherein Y is F, Cl, Br, or I, in the presence of a base.
    Type: Grant
    Filed: December 18, 2007
    Date of Patent: April 2, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew Paul Sharratt, Robert Elliott Low, John Charles McCarthy
  • Patent number: 8399721
    Abstract: Disclosed is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkene with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents of the chlorofluoroalkene with hydrogen to produce a fluorine-containing olefin, wherein said catalyst is a composition comprising chromium, nickel and optionally an alkali metal selected from potassium and cesium. Also disclosed are catalyst compositions for the hydrodechlorination of chlorofluoroalkenes comprising copper, nickel, and an alkali metal selected from potassium and cesium, and methods of making such catalysts.
    Type: Grant
    Filed: December 18, 2009
    Date of Patent: March 19, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Ekaterina N. Swearingen
  • Patent number: 8395001
    Abstract: To provide processes for efficiently and economically producing 2-chloro-1,1,1,2-tetrafluoropropane (R244bb) and 2,3,3,3-tetrafluoropropene (R1234yf) in an industrially practical manner. A process for producing 2-chloro-1,1,1,2-tetrafluoropropane, which comprises a chlorination step of reacting 1,2-dichloro-2-fluoropropane and chlorine in the presence of a solvent under irradiation with light to obtain 1,1,1,2-tetrachloro-2-fluoropropane, and a fluorination step of reacting the 1,1,1,2-tetrachloro-2-fluoropropane obtained in the chlorination step and hydrogen fluoride in the presence of a catalyst to obtain 2-chloro-1,1,1,2-tetrafluoropropane, and a process for producing 2,3,3,3-tetrafluoropropene, which comprises dehydrochlorinating it in the presence of a catalyst.
    Type: Grant
    Filed: June 10, 2011
    Date of Patent: March 12, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Satoshi Kawaguchi, Takashi Okazoe, Hidekazu Okamoto
  • Patent number: 8395000
    Abstract: Disclosed are methods for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CHXCH2X??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where X is independently Cl, Br, I or F, and Z independently is H or F. In certain preferred embodiments, each Z is different.
    Type: Grant
    Filed: February 8, 2010
    Date of Patent: March 12, 2013
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy, Daniel C. Merkel, Rajesh K. Dubey, Jing Ji Ma
  • Publication number: 20130060069
    Abstract: A method for producing a tetrafluoroolefin, such as 2,3,3,3-tetrafluoropropene (HFO-123434), comprises dehydrofluorinating a pentafluoroalkane in a gas phase in the presence of a catalyst comprising chromium oxyfluoride. In a preferred embodiment, 2,3,3,3-tetrafluoropropene (HFO-1234yf) is produced by forming a catalyst comprising chromium oxyfluoride by calcining CrF3?xH2O, where x is 1-10, in the presence of a flowing gas comprising nitrogen to form a calcined chromium oxyfluoride, and dehydrofluorinating 1,1,1,2,2-pentafluoropropane (HFC-245cb) in a gas phase in the presence of the catalyst to form the 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Application
    Filed: May 3, 2011
    Publication date: March 7, 2013
    Applicant: ARKEMA INC.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Olga C.N. Keeley, Benjamin Bin Chen
  • Patent number: 8389779
    Abstract: A subject-matter of the invention is a process for the preparation of 2,3,3,3-tetrafluoro-1-propene comprising the following stages: (i) hydrogenation of hexafluoropropylene to give 1,1,1,2,3,3-hexafluoropropane; (ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in the preceding stage to give 1,2,3,3,3-pentafluoro-1-propene; (iii) hydrogenation of the 1,2,3,3,3-pentafluoro-1-propene obtained in the preceding stage to give 1,1,1,2,3-pentafluoropropane; (iv) purification of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage; and (v) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage to give 2,3,3,3-tetrafluoro-1-propene; and (vi) purification of the 2,3,3,3-tetrafluoro-1-propene of the preceding stage.
    Type: Grant
    Filed: July 23, 2010
    Date of Patent: March 5, 2013
    Assignee: Arkema France
    Inventors: Karine Avril, Bertrand Collier
  • Patent number: 8383867
    Abstract: Disclosed is a method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CFnCHmXa-m??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where each X is independently Cl, F, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a-m?0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a Cl addition agent under conditions effective to produce a compound of formula (I).
    Type: Grant
    Filed: November 3, 2006
    Date of Patent: February 26, 2013
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Rajesh K. Dubey, Rajiv R. Singh, George A. Shia
  • Patent number: 8377327
    Abstract: A process is disclosed for the manufacture of CF3CF?CH2 and CF3CH?CHF. The process involves dehydrofluorinating CF3CHFCH2F in the presence of a dehydrofluorination catalyst to produce a product mixture comprising CF3CF?CH2 and CF3CH?CHF, and recovering said CF3CF?CH2 and CF3CH?CHF from the product mixture. The present invention also provides a composition comprising (a) the Z-isomer of CF3CH?CHF and (b) HF; wherein the HF is present in an effective amount to form an azeotropic combination with the Z—CF3CH?CHF.
    Type: Grant
    Filed: April 13, 2010
    Date of Patent: February 19, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Mario Joseph Nappa, Allen Capron Sievert, Ralph Newton Miller
  • Patent number: 8378158
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: February 19, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham
  • Publication number: 20130041190
    Abstract: Process of catalytic fluorination in liquid phase of product 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane into product 2-chloro-3,3,3-trifluoropropene in presence of a catalyst.
    Type: Application
    Filed: March 21, 2011
    Publication date: February 14, 2013
    Applicant: Arkema France
    Inventors: Anne Pigamo, Laurent Wendlinger, Philippe Bonnet
  • Patent number: 8373010
    Abstract: Disclosed is a process for the preparation of 3,3,3-trifluoropropene comprising the steps of; (1) fluorination of 240fa to form 245fa; (2) conversion of 245fa to a cis/trans mixture of 1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form 254fb ; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene. Alternatively or additionally, a second process for the preparation of the desired compound comprises the following steps; (1) fluorination of HCC-240fa to form HCFC-244fa; (2) conversion of 244fa to a cis/trans mixture of HFO-1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form HFC-254fb; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene.
    Type: Grant
    Filed: September 3, 2010
    Date of Patent: February 12, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Selma Bektesevic
  • Publication number: 20130035526
    Abstract: A method for producing a tetrafluoroolefin, such as 2,3,3,3-tetrafluoropropene (HFO-1234yf), comprises contacting 1,1,1,2-tetrachloro-2-fluoropropane (HCFC-241bb) with or without a catalyst under conditions effective to convert the 1,1,1,2-tetrachloro-2-fluoropropane (HCFC-241bb) to the tetrafluoroolefin, optionally, via an intermediate. The conversion may be a one-step fluorination or a two-step fluorination and dehydrochlorination process. The 1,1,1,2-tetrachloro-2-fluoropropane (HCFC-241bb) may also be obtained by dehydrochlorinating 1,2,3-trichloropropane (HCC-260da) to form 2,3-dichloropropene (HCO-1250xf); fluorinating 2,3-dichloropropene (HCO-1250xf) to form 1,2-dichloro-2-fluoropropane (HCFC-261bb); and chlorinating 1,2-dichloro-2-fluoropropane (HCFC-261bb) to form 1,1,1,2-tetrachloro-2-fluoropropane (HCFC-241bb).
    Type: Application
    Filed: April 8, 2011
    Publication date: February 7, 2013
    Applicant: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Patent number: 8367878
    Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
    Type: Grant
    Filed: February 7, 2012
    Date of Patent: February 5, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Publication number: 20130023703
    Abstract: A process for the selective dehydrofluorination of hydrochlorofluoroalkanes and novel hydrochlorofluoroalkenes is described wherein an effective amount of a catalytically active metal compound is applied which is selected from the group consisting of AlF3??, MgAlxF2+3x?? and MgZryF2+4y??, wherein x and y have, independently of one another, values in the range of from 0 to 0.33 and ? has a value in the range of from 0 to 0.1. Certain hydrofluorochloroalkenes are also described, as well as their use as intermediates in chemical reactions.
    Type: Application
    Filed: March 31, 2011
    Publication date: January 24, 2013
    Applicant: SOLVAY SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Patent number: 8357828
    Abstract: To provide a simple and economical process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, which does not require purification of the raw material component obtained in the form of a mixture of isomers, and a process for producing 2,3,3,3-tetrafluoropropene from the product thereby obtained. A process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, characterized by bringing a mixture of dichloropentafluoropropane isomers which contains 1,1-dichloro-2,2,3,3,3-pentafluoropropane into contact with an aqueous alkali solution in the presence of a phase transfer catalyst, and thereby selectively dehydrofluorinating only the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture, and a process for producing 2,3,3,3-tetrafluoropropene from the 1,1-dichloro-2,3,3,3-tetrafluoropropene thereby obtained.
    Type: Grant
    Filed: June 20, 2011
    Date of Patent: January 22, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Hidekazu Okamoto, Yasuyuki Sasao
  • Publication number: 20120330073
    Abstract: The present invention provides a process for producing a fluorine-containing alkene of the general formula CF3 (CX2)nCF?CH2, wherein X each independently represents F or Cl, and n is an integer of 0 to 2. The process includes a first reaction step of allowing a specific chlorine-containing compound to react with a fluorinating agent under increased pressure in a gas phase in the presence of at least one fluorination catalyst selected from the group consisting of chromium oxide and fluorinated chromium oxide, and a second reaction step of heating the product of the first reaction step in a gas phase under a pressure lower than the pressure in the first reaction step. The process of the present invention can produce a fluorine-containing alkene with a high selectivity with the use of a catalyst that can be easily handled, while suppressing production of by-products that cannot be easily converted into the target or separated.
    Type: Application
    Filed: February 8, 2011
    Publication date: December 27, 2012
    Inventors: Daisuke Karube, Yuzo Komatsu, Atsushi Suzuki
  • Publication number: 20120330072
    Abstract: This invention relates to a method of reacting fluoroolefin with an organic magnesium compound in the presence of a catalyst comprising nickel or palladium so as to efficiently produce fluoroolefin, such as TFE, in which a fluorine (F) atom or atoms bonded to the sp2 hybridized carbon atom are substituted with an organic group.
    Type: Application
    Filed: March 3, 2011
    Publication date: December 27, 2012
    Inventors: Takabumi Nagai, Takashi Shibanuma, Sensuke Ogoshi, Masato Ohashi
  • Patent number: 8338652
    Abstract: The present invention provides a simple and efficient process for producing 2,3,3,3-tetrafluoropropene(HFC-1234yf), the process being useful for industrial production. More specifically, the present invention relates to: a process for producing 2,3,3,3-tetrafluoropropene, comprising the steps of: (I) reacting a compound expressed by Formula (1): CF3CF2CH2X??(1) wherein X represents Cl, Br or I, with a base to produce a compound expressed by Formula (2): CF3CF?CHX??(2) wherein X is the same as above; and (II) reducing the compound expressed by Formula (2) with hydrogen in the presence of a catalyst to produce 2,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: September 10, 2008
    Date of Patent: December 25, 2012
    Assignee: Daikin Industries, Ltd.
    Inventors: Junpei Terada, Takuji Ishikawa
  • Patent number: 8338651
    Abstract: Halogenated alkenes, especially fluorinated alkenes can be prepared from halogenated and fluorinated alkanes, respectively, by dehydrohalogenation or dehydrofluorination in the presence of a high-surface metal fluoride or oxifluoride. Preferably, trifluoroethylene, pentafluoropropene, tetrafluorobutenes or trifluorobutadiene are prepared. Aluminum fluoride is highly suitable. The metal fluoride or oxifluoride can be applied supported on a carrier.
    Type: Grant
    Filed: July 11, 2008
    Date of Patent: December 25, 2012
    Assignee: Solvay Fluor GmbH
    Inventors: Ercan Uenveren, Erhard Kemnitz, Stephan Rudiger, Anton Dimitrov, Johannes Eicher
  • Patent number: 8329964
    Abstract: The invention relates to a gas-phase continuous method for preparing 2,3,3,3-tetrafluoro-1-propene, said method comprising the following steps: (i) hydrogenation of hexafluoropropylene to form 1,1,1,2,3,3-hexafluoropropane; (ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in the previous step to 1,2,3,3,3-pentafluoropropene-1; (iii) hydrogenation of the 1,2,3,3,3-pentafluoropropene-1 obtained in the previous step to form 1,1,1,2,3-pentafluoropropane; and (iv) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the previous step to form 2,3,3,3-tetrafluoro-1-propene.
    Type: Grant
    Filed: March 27, 2009
    Date of Patent: December 11, 2012
    Assignee: Arkema France
    Inventors: Michel Devic, Dominique Guillet, Emmanuel Guiraud, Laurent Wendlinger
  • Publication number: 20120302804
    Abstract: A production method of 3,3,3-trifluoropropene includes the step of hydrogenating 1-chloro-3,3,3-trifluoropropene with hydrogen (H2) in a gas phase in the presence of either of: (A) a catalyst having carried on a carrier at least one kind of transition metal selected from the group consisting of ruthenium, nickel, rhodium, iridium, iron, osmium and cobalt, or an oxide of said transition metal; (B) an oxide catalyst of copper and manganese; and (C) a catalyst having carried on a carrier palladium and at least one kind of element selected from the group consisting of bismuth, zinc, copper, silver, lanthanum, lead, zirconium, niobium, hafnium, magnesium, tin and arsenic.
    Type: Application
    Filed: January 18, 2011
    Publication date: November 29, 2012
    Applicant: Central Glass Company, Limited
    Inventors: Fuyuhiko Sakyu, Yasuo Hibino
  • Publication number: 20120302802
    Abstract: The present invention provides a process for producing fluorine-containing alkene represented by Formula (2): Rf1C(Rf2)?CH2 wherein Rf1 and Rf2 are the same or different, and are F, H, F(CF2)n- wherein n is an integer of 1 to 5, or H(CF2)m- wherein m is an integer of 1 to 5, with the proviso that Rf1 and Rf2 are not simultaneously H, by heating fluorine-containing alkane represented by Formula (1): Rf1CF(Rf2))CH3 wherein Rf1 and Rf2 are as defined above, in a gas phase to perform a dehydrofluorination reaction, the dehydrofluorination reaction being carried out in the presence of 5 mol or more of anhydrous hydrogen fluoride per mol of the fluorine-containing alkane. The process of the present invention can significantly enhance the selectivity of fluorine-containing alkene without reducing conversion in the production of fluorine-containing alkene from fluorine-containing alkane, such as fluorine-containing propane.
    Type: Application
    Filed: February 8, 2011
    Publication date: November 29, 2012
    Inventors: Yuzo Komatsu, Daisuke Karube
  • Publication number: 20120302803
    Abstract: The present invention provides a process for producing 2-chloro-3,3,3-trifluoropropene represented by the chemical formula: CF3CCl?CH2, comprising mixing a fluorine-containing alkane, in a liquid state, represented by the formula: CF3CH—ClCH2X, wherein X is halogen, with an aqueous solution containing at least one metal hydroxide selected from the group consisting of alkali metal hydroxides and alkali earth metal hydroxides in the presence of a catalyst to perform a dehydrohalogenation reaction of the fluorine-containing alkane. According to the present invention, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) can be obtained at a very high yield at a relatively low reaction temperature.
    Type: Application
    Filed: February 17, 2011
    Publication date: November 29, 2012
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Tsuneo Yamashita, Masatoshi Nose, Kenichi Katsukawa
  • Patent number: 8318992
    Abstract: A process is disclosed for making CF3CF2CH3, CF3CF?CH2 and/or CF3CCl?CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CH2CH2X, halopropenes of the formula CX3CH?CH2 and halopropenes of the formula CX2?CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 in a reaction zone to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF?CH2, and CF3CCl?CH2; and recovering the CF3CF2CH3, CF3CF?CH2 and/or CF3CCl?CH2 from the product mixture. Also disclosed is a process for making CF3CH2CHF2, CF3CH?CHF, and/or CF3CH?CHCl.
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: November 27, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20120296127
    Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.
    Type: Application
    Filed: May 15, 2012
    Publication date: November 22, 2012
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 8309774
    Abstract: The invention is directed to a process for preparing 2,2,2,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) 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, 2,2,2,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb); (iii) recycling at least a part of the second stream at least in part back to step (i).
    Type: Grant
    Filed: March 9, 2012
    Date of Patent: November 13, 2012
    Assignee: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Publication number: 20120271070
    Abstract: Disclosed is a fully integrated process for making 1,1,1,3,3-pentafluoropropane (HFC-245fa), trans-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), and trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)).
    Type: Application
    Filed: April 25, 2011
    Publication date: October 25, 2012
    Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • Patent number: 8293954
    Abstract: This invention achieves a catalyst life improvement for the catalyzed vapor phase reaction of 1,1,1,3,3-pentachloropropane with hydrogen fluoride to form 1-chloro-3,3,3-trifluoropropene by introducing an oxygen co-feed into the fluorination reactor. By introduction of an oxygen co-feed to the reactor feed, the catalyst life was extended a minimum of two-fold (2×).
    Type: Grant
    Filed: March 10, 2010
    Date of Patent: October 23, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Patent number: 8293953
    Abstract: To provide a method for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) at a high content ratio, which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (R1214ya). The method comprises subjecting a starting material comprising one isomer or a mixture of at least two isomers of dichloropentafluoropropane (HCFC-225) and having a HCFC-225ca content of less than 60 mol %, to an isomerization reaction in the presence of a Lewis acid catalyst or a metal oxide catalyst so as to increase the HCFC-225ca content in the product to be higher than the content in the starting material.
    Type: Grant
    Filed: March 21, 2011
    Date of Patent: October 23, 2012
    Assignee: Asahi Glass Company, Limited
    Inventor: Hidekazu Okamoto
  • Patent number: 8288597
    Abstract: Disclosed is a process for the manufacture of hydrofluoroolefins of the structure CF3CF?CHY, wherein Y can be H or F, comprising reacting at least one fluoropropane reactant of the structure CF3CFXCFYH, wherein X can be either F or H, and Y can be either F or H, provided that both X and Y? are not both F, with a basic aqueous solution in the presence of a non-aqueous, non-alcoholic solvent, and in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: October 16, 2012
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert, Mario Joseph Nappa
  • Patent number: 8263816
    Abstract: A process is disclosed for making CF3CF?CHF. The process involves reacting CF3CClFCCl2F with H2 in a reaction zone in the presence of a catalyst to produce a product mixture comprising CF3CF?CHF. The catalyst has a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina, fluorided alumina, aluminum fluoride and mixtures thereof and the mole ratio of H2 to CF3CClFCCl2F fed to the reaction zone is between about 1:1 and about 5:1. Also disclosed are azeotropic compositions of CF3CClFCCl2F and HF and azeotropic composition of CF3CHFCH2F and HF.
    Type: Grant
    Filed: June 22, 2007
    Date of Patent: September 11, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Mario Joseph Nappa, Allen Capron Sievert
  • Patent number: 8263817
    Abstract: Disclosed is a process for the manufacture of 2,3,3,3-tetrafluoropropene comprising: (a) contacting 1,1,1,2,tetrafluoro-2-chloropropane with a catalyst comprised of chromium (III) oxide, and at least 1% of an alkali metal, to produce a product mixture comprising 2,3,3,3-tetrafluoropropene; and (b) recovering said 2,3,3,3-tetrafluoropropene from the product mixture produced in step (a) above.
    Type: Grant
    Filed: June 30, 2011
    Date of Patent: September 11, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Robert D. Lousenberg, Andrew Jackson
  • Patent number: 8258353
    Abstract: The present invention provides one-step processes for the production of chlorinated and/or fluorinated propenes. The processes provide good product yield with low, e.g., less than about 20%, or even less than 10%, concentrations of residues/by-products. Advantageously, the processes may be conducted at low temperatures relative to conventional processes, so that energy savings are provided, and/or at higher pressures so that high throughputs may also be realized. The use of catalysts may provide enhancements to conversion rates and selectivity over those seen in conventional processes, as may adjustments to the molar ratio of the reactants.
    Type: Grant
    Filed: April 20, 2010
    Date of Patent: September 4, 2012
    Assignee: Dow Global Technologies, LLC
    Inventors: William J. Kruper, Jr., Max M. Tirtowidjojo, Kurt F. Hirsekorn, Debashis Chakraborty, Juergen Eiffler
  • Publication number: 20120215035
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a chromium oxyfluoride catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.
    Type: Application
    Filed: February 16, 2012
    Publication date: August 23, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventor: MARIO JOSEPH NAPPA
  • Publication number: 20120215036
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a carbon catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.
    Type: Application
    Filed: February 16, 2012
    Publication date: August 23, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Patent number: 8247624
    Abstract: Dehydrohalogenation processes for the preparation of fluoropropenes from corresponding halopropanes, in which the fluoropropenes have the formula CF3CY?CXNHP, wherein X and Y are independently hydrogen or a halogen selected from fluorine, chlorine, bromine and iodine; and N and P are independently integers equal to 0, 1 or 2, provided that (N+P)=2.
    Type: Grant
    Filed: September 6, 2011
    Date of Patent: August 21, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh S. Tung
  • Patent number: 8242316
    Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.
    Type: Grant
    Filed: August 1, 2011
    Date of Patent: August 14, 2012
    Assignee: Honeywell International Inc.
    Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
  • Patent number: 8232435
    Abstract: The present disclosure relates to a new and efficient manufacturing process for the production of HFC-1225ye. The process involves contacting at least one hexafluoropropane selected from the group consisting of 1,1,1,2,2,3-hexafluoropropane and 1,1,1,2,3,3-hexafluoropropane with a suitable catalyst in a reactor to obtain a product mixture containing HFC-1225ye (1,2,3,3,3-pentafluoropropene) where the pressure in the reactor ranges from about 0.5 psig to about 100 psig.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: July 31, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Allen Capron Sievert, Mario Joseph Nappa, Barry Asher Mahler
  • Publication number: 20120184786
    Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd(E)), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 240fa with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd(E) and 244fa (plus byproduct HCl); (2) the 244fa stream can then be used to directly produce any of the three desired products; (3a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze(E); and/or (3b) the 244fa stream can be dehydrofluorinated to produce 1233zd(E) if more of that product is desired; and/or (3c) the 244fa stream can be further fluorinated to form 245fa.
    Type: Application
    Filed: December 9, 2011
    Publication date: July 19, 2012
    Inventors: Daniel C. Merkel, Haiyou Wang, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • Publication number: 20120149951
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2?CClCH2Cl is fluorinated to synthesize a compound such as CF3CCl?CH2. The CF3CCl?CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl?CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.
    Type: Application
    Filed: November 22, 2011
    Publication date: June 14, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: SUDIP MUKHOPADHYAY, HSUEH S. TUNG, MICHAEL VAN DER PUY, DANIEL C. MERKEL, JING JI MA, CHERYL L. BORTZ, BARBARA A. LIGHT, STEVEN D. PHILLIPS, RAJESH K. DUBEY
  • Patent number: 8198491
    Abstract: The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene represented by CF3CF?CH2 and 1,3,3,3-tetrafluoropropene represented by CF3CH?CHF, in which 3,3,3-trifluoropropyne represented by the chemical formula CF3C?CH is reacted with hydrogen fluoride under heating. The process of the present invention is a simple, effective and industrially applicable process for preparing 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: June 12, 2012
    Assignee: Daikin Industries, Ltd.
    Inventors: Nose Masatoshi, Komatsu Yuzo, Sugiyama Akinari, Shibanuma Takashi
  • Publication number: 20120136183
    Abstract: The invention relates to a method for preparing fluoropropenes of formula (I) CF3CF?CHR, where R is a hydrogen or a fluorine atom from at least one compound of formula (Ia) CF3CF?CFR, where R has the same meaning as in formula (I), said method including the following steps: (i) hydrogenating at least one compound of formula (Ia) in an adiabatic reactor in the presence of a catalyst with a superstoichiometric amount of hydrogen so as to produce a hydrofluoropropane; (ii) partially condensing the flow from the adiabatic reactor of step (i) so as to produce a gaseous phase fraction, including unreacted hydrogen and a portion of the formed hydrofluoropropane, which is recirculated to step (i), and a liquid phase fraction including the residue of the hydrofluoropropane; (iii) dehydrofluorinating hydrofluoropropane from the liquid fraction of step (ii) using potassium hydroxide in an aqueous reaction medium contained in an agitated reactor so as to produce the fluoropropene of formula (I); and (iv) purifying the fl
    Type: Application
    Filed: May 21, 2010
    Publication date: May 31, 2012
    Applicant: Arkema France
    Inventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini, Pierre-Marie Sedat, Karine Avril
  • Publication number: 20120136182
    Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
    Type: Application
    Filed: February 7, 2012
    Publication date: May 31, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh S. Tung