Alkali Or Alkaline Earth Metal Containing Catalyst Patents (Class 570/157)
  • Patent number: 10384992
    Abstract: A method for manufacturing hydrofluoroolefin, includes: converting hydrofluorocarbon represented by a formula (1) into hydrofluoroolefin (HFO) represented by formula (2) in the presence of carbon dioxide to obtain a first gas composition containing hydrofluoroolefin and carbon dioxide; and separating carbon dioxide contained in the first gas composition to obtain a second gas composition containing HFO, CR1R2X1CR3R4X2 . . . (1), CR1R2?CR3R4 . . . (2), wherein R1 to R3 are each independently hydrogen atom or fluorine atom, R4 is hydrogen atom, fluorine atom, CH3, CH2F, CHF2 or CF3, the total number of fluorine atoms of R1 to R4 is one or more, and the total number of hydrogen atoms of R1 to R4 is one or more, X1 and X2 are each hydrogen atom or fluorine atom where X2 is the fluorine atom when X1 is the hydrogen atom, and X2 is the hydrogen atom when X1 is the fluorine atom.
    Type: Grant
    Filed: October 5, 2017
    Date of Patent: August 20, 2019
    Assignee: AGC Inc.
    Inventors: Yusuke Tomiyori, Masahiko Nakamura
  • Patent number: 9533926
    Abstract: A production method of 2-chloro-1,3,3,3-tetrafluoropropene (1224) according to the present invention includes bringing 2,3-dichloro-1,1,1,3-tetrafluoropropane (234da) into contact with an inorganic base having a pKa of 4.8 or greater in an aqueous medium in the presence of a phase transfer catalyst. Preferably, the inorganic base has a pKa of 10 or greater. Further, the phase transfer catalyst is preferably at least one selected from the group consisting of tetrabutylammonium bromide, methyltri-n-octylammonium chloride, benzyltrimethylammonium chloride and tetraethylammonium chloride. It is possible by this method to selectively produce 1224 from 234da.
    Type: Grant
    Filed: July 27, 2015
    Date of Patent: January 3, 2017
    Assignee: Central Glass Company, Limited
    Inventors: Hideaki Imura, Naoto Takada
  • Patent number: 9532567
    Abstract: A copolymer comprising trans-1,3,3,3-tetrafluoropropene units and vinylidene fluoride units, and methods of making the same. A method of preventing biofouling on an article of manufacture, comprising applying such copolymer to the article of manufacture. A process of preparing a surface having a surface energy of between about 20 and about 30 mJ/m2, comprising applying such a copolymer to a support. A method of preventing accumulation of ice on an article of manufacture, comprising applying such a copolymer to an article of manufacture. A method of preparing a polymer, comprising a step of adding trans-1,3,3,3-tetrafluoropropene/vinylidene fluoride copolymer as a polymer processing additive/aid to said polymer.
    Type: Grant
    Filed: November 11, 2013
    Date of Patent: January 3, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Changqing Lu, Andrew J. Poss, Rajiv R. Singh, David Nalewajek, Cheryl Cantlon
  • Patent number: 9428809
    Abstract: Provided are a solid-phase carrier for solid-phase synthesis of nucleic acid having improved amino group reactivity, and an aminated oligonucleotide to which an amino group has been attached. The present invention relates to an aminated oligonucleotide represented by formula (I).
    Type: Grant
    Filed: July 31, 2012
    Date of Patent: August 30, 2016
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Yasuo Komatsu, Naoshi Kojima
  • Patent number: 9187386
    Abstract: This disclosure relates to processes of making 1,3,3,3-tetrafluoropropene. The processes involve dehydrofluorinating 1,1,1,3,3-pentafluoropropane in vapor phase in the presence of a catalyst comprising a metal compound supported on alumina to produce a product mixture comprising 1,3,3,3-tetrafluoropropene, wherein said metal compound is selected from the group consisting of salts of sodium, potassium, zinc, magnesium, calcium, cobalt, copper, and chromium, and mixtures thereof.
    Type: Grant
    Filed: May 13, 2014
    Date of Patent: November 17, 2015
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Patent number: 9162948
    Abstract: The invention provides a process for the preparation of 1234yf comprising (a) contacting 1,1,2,3,3,3 hexafluoropropene (1216) with hydrogen in the presence of a hydrogenation catalyst to produce 1,1,2,3,3,3 hexafluoropropane (236ea); (b) dehydrofluorinating 236ea to produce 1,2,3,3,3 -pentafluoropropene (1225ye); (c) contacting 1225 ye with hydrogen in the presence of a hydrogenation catalyst to produce 1,2,3,3,3 -pentafluoropropane (245eb); and (d) dehydrofluorinating (245eb) to produce (1234yf).
    Type: Grant
    Filed: May 15, 2009
    Date of Patent: October 20, 2015
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: John W Smith, Claire McGuiness, Andrew P Sharratt, Andrew M Taylor
  • Patent number: 9149796
    Abstract: The use of metal-accumulating plants for implementing chemical reactions.
    Type: Grant
    Filed: November 18, 2010
    Date of Patent: October 6, 2015
    Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, UNIVERSITE MONTPELLIER 2 SCIENCES ET TECHNIQUES
    Inventors: Claude Grison, Jose Escarre
  • Patent number: 9090530
    Abstract: A method for producing 1,2-dichloro-3,3,3-trifluoropropene of the present invention includes reacting 1,2-dichloro-1-halogeno-3,3,3-trifluoropropane with a base in a liquid phase; and extracting generated 1,2-dichloro-3,3,3-trifluoropropene to the outside of a reaction system to recover while the reaction is continued. According to the present invention, 1,2-dichloro-3,3,3-trifluoropropene is obtained at a high yield by a simple method. Thus, 1,2-dichloro-3,3,3-trifluoropropene is produced in an industrial scale.
    Type: Grant
    Filed: March 19, 2015
    Date of Patent: July 28, 2015
    Assignee: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Yoshio Nishiguchi, Satoru Okamoto, Fuyuhiko Sakyu
  • Patent number: 9012702
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCFClCH2X with a catalyst in a reaction zone to produce a product mixture comprising RfCF?CHX, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, X ?H, F, Cl, Br or I, M=K, Na or Cs, and Y?F, Cl or Br.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: April 21, 2015
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Publication number: 20150080618
    Abstract: A production method of cis-1,3,3,3-tetrafluoropropene according to the present invention includes the steps of: subjecting 1,1,1,3,3-pentafluoropropane to dehydrofluorination to form a reaction mixture (A) containing cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and unreacted 1,1,1,3,3-pentafluoropropane; distilling the reaction mixture (A) to separate the trans-1,3,3,3-tetrafluoropropene from the reaction mixture (A) and collect a reaction mixture (B) containing the cis-1,3,3,3-tetrafluoropropene and the 1,1,1,3,3-pentafluoropropane; and reacting the reaction mixture (B) with a base and thereby obtaining the cis-1,3,3,3-tetrafluoropropene from the reaction mixture (B). This production method enables efficient production of high-purity cis-1,3,3,3-tetrafluoropropene and thus has industrial advantages.
    Type: Application
    Filed: April 2, 2013
    Publication date: March 19, 2015
    Inventors: Satoshi Yoshikawa, Satoru Okamoto, Yoshio Nishiguchi, Fuyuhiko Sakyu
  • Publication number: 20140350310
    Abstract: This disclosure relates to processes of making 1,3,3,3-tetrafluoropropene. The processes involve dehydrofluorinating 1,1,1,3,3-pentafluoropropane in vapor phase in the presence of a catalyst comprising a metal compound supported on alumina to produce a product mixture comprising 1,3,3,3-tetrafluoropropene, wherein said metal compound is selected from the group consisting of salts of sodium, potassium, zinc, magnesium, calcium, cobalt, copper, and chromium, and mixtures thereof.
    Type: Application
    Filed: May 13, 2014
    Publication date: November 27, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: XUEHUI SUN, MARIO JOSEPH NAPPA
  • Publication number: 20140350311
    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: Application
    Filed: August 12, 2014
    Publication date: November 27, 2014
    Inventors: ROBERT C. JOHNSON, HSUEH S. TUNG, DANIEL C. MERKEL
  • 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: 8884083
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, M=K, Na or Cs, and Y=F, Cl or Br.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: November 11, 2014
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Patent number: 8841493
    Abstract: The subject matter of the invention is a process for preparing fluoroolefin compounds. The invention relates more particularly to a process for producing a (hydro)fluoroolefin compound, which comprises (i) bringing at least one compound comprising from three to six carbon atoms, at least two fluorine atoms and at least one hydrogen atom, on the condition that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, into contact with a solid reactant comprising calcium hydroxide.
    Type: Grant
    Filed: May 4, 2010
    Date of Patent: September 23, 2014
    Assignee: Arkema France
    Inventors: Dominique Guillet, Michel Devic
  • Publication number: 20140275649
    Abstract: The present invention relates to a provides a catalyst comprising (a) a solid support comprising an alkaline earth metal oxide, fluoride, or oxyfluoride, and (b) at least one elemental metal disposed on or within said support, preferably wherein said elemental metal is present in an amount from about 0.01 to about 10 weight percent based upon the total weight of the metal and support. It also relates to the use of the catalyst for the dehydrochlorination of a hydrochlorofluorocarbon.
    Type: Application
    Filed: March 12, 2014
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou WANG, Hsueh Sung TUNG
  • Patent number: 8835698
    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: May 7, 2013
    Date of Patent: September 16, 2014
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
  • Patent number: 8829254
    Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: September 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv Ratna Singh, David Nalewajek, Andrew Joseph Poss
  • Patent number: 8779217
    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: Grant
    Filed: May 21, 2010
    Date of Patent: July 15, 2014
    Assignee: Arkema France
    Inventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini, Pierre-Marie Sedat, Karine Avril
  • Patent number: 8710282
    Abstract: The instant invention relates, at least in part, to a method increasing the cost efficiency for dehydrohalogenation production of a fluorinated olefin by recovering and recycling spent dehydrohalogenation agent. In one aspect, the present invention relates to dehydrohalogenating a fluorinated alkane (e.g. pentafluoropropane and/or hexafluoropropane) in the presence of a dehydrohalogenating agent to produce a fluorinated olefin (e.g. tetrafluoropropenes and/or pentafluoropropenes). Removal of spent dehydrohalogenating agent from the reactor allows for facile separation of organic and dehydrohalogenating agent, the latter of which is recycled.
    Type: Grant
    Filed: September 9, 2011
    Date of Patent: April 29, 2014
    Assignee: Honeywell International Inc.
    Inventors: Selma Bektesevic, Hsueh Sung Tung, Haluk Kopkalli
  • Patent number: 8648222
    Abstract: There is provided methods for making a catalyst composition represented by the formula MX/M?F2 wherein MX is an alkali metal halide; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?; M?F2 is a bivalent metal fluoride; and M? is a bivalent metal ion. There is also a method for making a fluorinated olefin.
    Type: Grant
    Filed: July 6, 2011
    Date of Patent: February 11, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20140012049
    Abstract: Disclosed are processes for producing halogenated olefins, and preferably tetrafluorinated propene(s), from one or more alkanes having both fluorine substituents and non-fluorine substituents, preferably with a high degree of conversion and selectivity. Preferably the process comprises the use of a catalyzed reaction in which the catalyst is selected from the group consisting of activated carbons, halogentated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.
    Type: Application
    Filed: August 16, 2013
    Publication date: January 9, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HAIYOU WANG, HSUEH SUNG TUNG, SUDIP MUKHOPADHYAY
  • Patent number: 8618340
    Abstract: Disclosed is a process for the manufacture of HFO-1234yf from TCP in three integrated steps that include hydrofluorination of TCP (tetrachloropropene) to HCFC-1233xf in the vapor phase followed by hydrofluorination of HCFC-1233xf to HCFC-244bb in the liquid phase which is then followed by dehydrochlorination in liquid or vapor phase to produce HFO-1234yf. The vapor phase hydrofluorination is carried out at a higher pressure than the liquid phase hydrofluorination, thereby eliminating the need for compression and/or intermediate recovery. Also, any HCl generated from this reaction is fed to the liquid phase hydrofluorination section to promote agitation and mixing. This results in a more economical process from an initial capital and operating cost versus conducting the 3-steps sequentially.
    Type: Grant
    Filed: November 3, 2009
    Date of Patent: December 31, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Kevin Uhrich
  • Patent number: 8536388
    Abstract: The present invention provides a process for its preparation comprising (a) converting 1,1,1-trifluoro-2,3-dichloropropane (243db) to 3,3,3-trifluoro-2-chloro-prop-1-ene (CF3CCI?CH2) in the presence of a first catalyst in a first reactor, (b) contacting CF3CCI?CH2 with a fluorinating agent in the presence of a second catalyst in a second reactor to produce a compound of formula CF3CFXCH3, wherein X?Cl or F, and (c) dehydrohalogenating the compound of formula CF3CFXCH3 to produce 2,3,3,3-tetrafluoropropene (1234yf).
    Type: Grant
    Filed: April 9, 2009
    Date of Patent: September 17, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: John W. Smith, Claire E McGuiness, Andrew Paul Sharratt
  • Patent number: 8530708
    Abstract: Disclosed are processes for producing halogenated olefins, and preferably tetrafluorinated propene(s), from one or more alkanes having both fluorine substituents and non-fluorine substituents, preferably with a high degree of conversion and selectivity. Preferably the process comprises the use of a catalyzed reaction in which the catalyst is selected from the group consisting of activated carbons, halogentated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: September 10, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Sudip Mukhopadhyay
  • Publication number: 20130211155
    Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.
    Type: Application
    Filed: February 4, 2013
    Publication date: August 15, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: Honeywell International Inc.
  • Publication number: 20130211156
    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: Application
    Filed: February 4, 2013
    Publication date: August 15, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: HONEYWELL INTERNATIONAL INC.
  • Patent number: 8487145
    Abstract: Disclosed is a process for the manufacture of 2,3,3,3-tetrafluoropropene comprising: (a) contacting 1,1,1,2,3-pentafluoropropane with a catalyst comprised of chromium (III) oxide having a surface area of at least 150 m2/g and having an alkali metal loading of at least 7 milligrams of alkali metal per 100 square meters of catalyst surface area, to produce a product mixture comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride; and (b) recovering said 2,3,3,3-tetrafluoropropene from the product mixture produced in (a).
    Type: Grant
    Filed: March 12, 2012
    Date of Patent: July 16, 2013
    Assignee: E I de Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Andrew Jackson
  • 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: 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: 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: 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
  • 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: 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: 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
  • Publication number: 20120215037
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCFClCH2X with a catalyst in a reaction zone to produce a product mixture comprising RfCF?CHX, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, X?H, F, Cl, Br or I, M=K, Na or Cs, and Y?F, Cl or Br.
    Type: Application
    Filed: February 10, 2012
    Publication date: August 23, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: XUEHUI SUN, Mario Joseph Nappa
  • Publication number: 20120215038
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, M=K, Na or Cs, and Y=F, Cl or Br.
    Type: Application
    Filed: February 10, 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: 8227649
    Abstract: Disclosed is a process for the manufacture of 2,3,3,3-tetrafluoropropene comprising: (a) contacting 1,1,1,2,3-pentafluoropropane with a catalyst comprised of chromium (III) oxide and from 0.1% to 2% of an alkali metal disposed on the surface of said catalyst, to produce a product mixture comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride; and (b) recovering said 2,3,3,3-tetrafluoropropene from the product mixture produced in (a).
    Type: Grant
    Filed: July 22, 2011
    Date of Patent: July 24, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Andrew Jackson
  • Publication number: 20120172639
    Abstract: Disclosed is a process for the manufacture of 2,3,3,3-tetrafluoropropene comprising: (a) contacting 1,1,1,2,3-pentafluoropropane with a catalyst comprised of chromium (III) oxide having a surface area of at least 150 m2/g and having an alkali metal loading of at least 7 milligrams of alkali metal per 100 square meters of catalyst surface area, to produce a product mixture comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride; and (b) recovering said 2,3,3,3-tetrafluoropropene from the product mixture produced in (a).
    Type: Application
    Filed: March 12, 2012
    Publication date: July 5, 2012
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: MARIO JOSEPH NAPPA, Andrew Jackson
  • Publication number: 20120172638
    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: Application
    Filed: June 30, 2011
    Publication date: July 5, 2012
    Applicant: E. I. DUPONT DE NEMOURS AND COMPANY
    Inventors: Mario Joseph Nappa, Robert D. Lousenberg, Andrew Jackson
  • Patent number: 8148586
    Abstract: A process is disclosed for making CF3CF?CHF. The process involves contacting at least one hexafluoropropane selected from the group consisting of CF3CF2CH2F and CF3CHFCHF2 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CF?CHF, and recovering CF3CF?CHF from the product mixture. A process is disclosed for making CF3CH?CHF. The process involves contacting CF3CH2CHF2 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CH?CHF, and recovering CF3CH?CHF from the product mixture. A process is disclosed for making CF3CF?CH2. The process involves contacting CF3CF2CH3 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CF?CH2, and recovering CF3CF?CH2 from the product mixture.
    Type: Grant
    Filed: June 3, 2011
    Date of Patent: April 3, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao
  • Publication number: 20120059201
    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: Application
    Filed: September 3, 2010
    Publication date: March 8, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Patent number: 8067649
    Abstract: Disclosed is a process for producing tetrafluoropropene comprising: (a) catalytically fluorinating at least one tetrafluoropropene in a first reactor to produce HCFO-1233xf; (b) reacting said HCFO-1233xf with hydrogen fluoride in a second reactor to produce HCFC-244bb; (c) recycling at least a portion of said HCFC-244bb back to said first reactor as recycled HCFC-244bb; and (d) catalytically dehydrochlorinating said recycled HCFC-244bb in said first reactor to produce HFO-1234yf.
    Type: Grant
    Filed: May 14, 2009
    Date of Patent: November 29, 2011
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Hsueh Sung Tung
  • Publication number: 20110282112
    Abstract: Disclosed is a process for the manufacture of 2,3,3,3-tetrafluoropropene comprising: (a) contacting 1,1,1,2,3-pentafluoropropane with a catalyst comprised of chromium (III) oxide and from 0.1% to 2% of an alkali metal disposed on the surface of said catalyst, to produce a product mixture comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride; and (b) recovering said 2,3,3,3-tetrafluoropropene from the product mixture produced in (a).
    Type: Application
    Filed: July 22, 2011
    Publication date: November 17, 2011
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: MARIO JOSEPH NAPPA, ANDREW JACKSON
  • Publication number: 20110282111
    Abstract: There is provided methods for making a catalyst composition represented by the formula MX/M?F2 wherein MX is an alkali metal halide; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?; M?F2 is a bivalent metal fluoride; and M? is a bivalent metal ion. One method has the following steps: (a) dissolving an amount of the alkali metal halide in an amount of solvent sufficient to substantially dissolve or solubilize the alkali metal halide to form an alkali metal halide solution; (b) adding an amount of the bi-valent metal fluoride to the alkali metal halide solution to form a slurry of the alkali metal halide and bi-valent metal fluoride; and (c) removing substantially all of the solvent from the slurry to form a solid mass of the alkali metal halide and bi-valent metal fluoride.
    Type: Application
    Filed: July 6, 2011
    Publication date: November 17, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HAIYOU WANG, HSUEH SUNG TUNG
  • Patent number: 8053612
    Abstract: A process for making a fluorinated olefin. The process has the step of dehydrochlorinating a hydrochlorofluorocarbon having at least one hydrogen atom and at least one chlorine atom on adjacent carbon atoms in the presence of a catalytically effective amount of a catalyst composition. The catalyst composition is represented by the following: n wt. % MX/M?OyFz, wherein 0<y<1 and 0<z<2 and wherein y+z/2=1; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?, M? is a bivalent metal ion; wherein n is a weight percentage of about 0.05% to about 50% MX based on the total weight of the MX and M?OyFz, and wherein y and z are the mole fractions of oxygen and fluorine in M?OyFz, respectively. There are also methods for making catalyst compositions.
    Type: Grant
    Filed: May 27, 2009
    Date of Patent: November 8, 2011
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8034984
    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 22, 2010
    Date of Patent: October 11, 2011
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh S. Tung