Isomerization Patents (Class 570/151)
  • Patent number: 12123631
    Abstract: A fluoropropene composition comprising Z-1,3,3,3-tetrafluoropropene, E-1,3,3,3-tetrafluoropropene, 1,1,3,3,3-pentafluoropropene, 2,3,3,3-tetrafluoropropene, and optionally 1,1,1,3,3-pentafluoropropane wherein the 2,3,3,3-tetrafluoropropene being present in an amount of 0.00001 to 1.0%. A method of producing the fluoropropene, methods for using the fluoropropene and the composition formed are also disclosed.
    Type: Grant
    Filed: January 17, 2024
    Date of Patent: October 22, 2024
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Sheng Peng, Mario Joseph Nappa
  • Patent number: 12054445
    Abstract: A method for efficiently obtaining trans-1-halo-2-fluoroethylene (E-isomer) and/or cis-1-halo-2-fluoroethylene (Z-isomer) is provided. The method for producing trans-1-halo-2-fluoroethylene (E-isomer) and/or cis-1-halo-2-fluoroethylene (Z-isomer) includes supplying a composition containing trans-1-halo-2-fluoroethylene (E-isomer) and/or cis-1-halo-2-fluoroethylene (Z-isomer) to a reactor to perform isomerization between the trans-1-halo-2-fluoroethylene (E-isomer) and the cis-1-halo-2-fluoroethylene (Z-isomer) in a liquid phase by performing light irradiation in the presence of a photosensitizer.
    Type: Grant
    Filed: December 7, 2021
    Date of Patent: August 6, 2024
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Tomo Otsuka, Tsubasa Nakaue, Kazuhiro Takahashi
  • Patent number: 11267772
    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 1225ye 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: June 9, 2020
    Date of Patent: March 8, 2022
    Assignee: MEXICHEM AMANCO HOLDING S.A. DE C.V.
    Inventors: John W Smith, Claire McGuinness, Andrew P Sharratt, Andrew M Taylor
  • Patent number: 10703696
    Abstract: The method for isomerizing an organic compound comprises a step of selecting an alumina so that the acid amount calculated from the amount of ammonia desorbed at a desorption temperature of at least 300° C. by temperature-programmed desorption of ammonia is at least 0.10 mmol/g and at most 0.25 mmol/g; a step of fluorinating the selected alumina by a fluorinating agent to produce a partially fluorinated alumina; and a step of isomerizing, by using the obtained partially fluorinated alumina, an organic compound having at least two carbon atoms wherein to at least one of the adjacent carbon atoms, at least one fluorine atom is bonded and to the other, at least one chlorine atom or hydrogen atom is bonded.
    Type: Grant
    Filed: April 19, 2019
    Date of Patent: July 7, 2020
    Assignee: AGC Inc.
    Inventors: Taku Yamada, Yusuke Suzuki, Mitsugu Kasagawa
  • Patent number: 10683248
    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 1225ye 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: April 24, 2018
    Date of Patent: June 16, 2020
    Assignee: MEXICHEM AMANCO HOLDING S.A. DE C.V.
    Inventors: John W Smith, Claire McGuinness, Andrew P Sharratt, Andrew M Taylor
  • Patent number: 10590051
    Abstract: The present invention provides a method for producing a target fluorine-containing olefin with high conversion and selectivity using a process comprising a dehydrofluorination reaction of a hydrofluorocarbon. The method comprises a first reaction step comprising subjecting a hydrofluorocarbon to dehydrofluorination in the presence of a catalyst. The hydrofluorocarbon is a compound represented by Formula (1): RfCFYCHZ2, wherein Rf represents a straight or branched C1-3 perfluoroalkyl group, and Y and Z each independently represent H or F wherein when all Zs are H, Y represents F. The catalyst comprises chromium oxide represented by the chemical formula: CrOm (1.5<m<3).
    Type: Grant
    Filed: May 18, 2016
    Date of Patent: March 17, 2020
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Takehiro Chaki, Shun Ohkubo, Daisuke Karube
  • Patent number: 10513479
    Abstract: A method for isomerizing a hydrohalofluoroolefin isomer to produce a corresponding hydrohalofluoroolefin isomer includes a step contacting a composition that contains at least a hydrohalofluoroolefin isomer and that has been adjusted to 100 ppm or lower in moisture concentration, with a catalyst in a gas phase, thereby obtaining a product. This method makes it possible to suppress the catalyst performance lowering.
    Type: Grant
    Filed: May 27, 2016
    Date of Patent: December 24, 2019
    Assignee: Central Glass Company, Limited
    Inventors: Takamasa Kitamoto, Satoru Okamoto, Masahiko Tani, Masatomi Kanai, Kohei Sumida
  • Patent number: 10442743
    Abstract: The present invention provides a process for the preparation of a (hydro)(chloro)fluoroalkene by contacting a reagent stream comprising a hydrochlorofluoroalkane with a catalyst in a reactor to dehydrochlorinate at least a portion of the hydrochlorofluoroalkane to produce a product stream comprising the (hydro)(chloro)fluoroalkene and hydrogen chloride (HCl), wherein the catalyst is selected from the group consisting of metal oxide catalysts, metal halide catalysts, zero-valent metal catalysts, carbon-based catalysts and mixtures thereof, and wherein (i) the catalyst is chlorinated prior to contacting it with the reagent stream comprising the hydrochlorofluoroalkane; and/or (ii) the contacting step is carried out in the presence of a HCl co-feed.
    Type: Grant
    Filed: April 16, 2018
    Date of Patent: October 15, 2019
    Assignee: MEXICHEM AMANCO HOLDING S.A. de C.V.
    Inventors: Andrew Paul Sharratt, Claire Nicola Rees, Maxine Doran
  • Patent number: 10221113
    Abstract: A hydrogenation process is disclosed. The process involves reacting a fluoroolefin with H2 in a reaction zone in the presence of a palladium catalyst to produce a hydrofluoroalkane product, wherein the palladium catalyst comprises palladium supported on a carrier wherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the carrier. Also disclosed is a palladium catalyst composition consisting essentially of palladium supported on ?-Al2O3 wherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the ?-Al2O3. Also disclosed is a hydrogenation process comprising reacting a fluoroolefin with H2 in a reaction zone in the presence of a palladium catalyst to produce a hydrofluoroalkane product, characterized by: the palladium catalyst consisting essentially of palladium supported on ?-Al2O3 wherein the palladium concentration is from about 0.001 wt % to about 0.
    Type: Grant
    Filed: January 26, 2017
    Date of Patent: March 5, 2019
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Patricia Cheung, Concetta Lamarca
  • Patent number: 10099976
    Abstract: Disclosed is a process for the preparation of cis-1,1,1,4,4,4-hexafluoro-2-butene comprising contacting 1,1,1-trifluorotrichloroethane with hydrogen in the presence of a catalyst comprising ruthenium to produce a product mixture comprising 1316mxx, recovering said 1316mxx as a mixture of Z- and E-isomers, contacting said 1316mxx with hydrogen, in the presence of a catalyst selected from the group consisting of copper on carbon, nickel on carbon, copper and nickel on carbon and copper and palladium on carbon, to produce a second product mixture, comprising E- or Z-CFC-1326mxz, and subjecting said second product mixture to a separation step to provide E- or Z-1326mxz.
    Type: Grant
    Filed: September 8, 2017
    Date of Patent: October 16, 2018
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Ivan Sergeyevich Baldychev, Stephan M Brandstadter, Patricia Cheung, Mario Joseph Nappa, Sheng Peng, Donald J Toton
  • Patent number: 9994504
    Abstract: Disclosed are processes for a high temperature isomerization reaction converting (E)-1-chloro-3,3,3-trifluoropropene to (Z)-1-chloro-3,3,3-trifluoropropene. In certain aspects of the invention, such a process includes contacting a feed stream with a heated surface, where the feed stream includes (E)-1-chloro-3,3,3-trifluoropropene or mixture of (E)-1-chloro-3,3,3-trifluoropropene with (Z)-1-chloro-3,3,3-trifluoropropene. The resulting product stream includes (Z)-1-chloro-3,3,3-trifluoropropene and (E)-1-chloro-3,3,3-trifluoropropene, where the ratio of (Z) isomer to (E) isomer in the product stream is higher than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.
    Type: Grant
    Filed: May 5, 2017
    Date of Patent: June 12, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9764998
    Abstract: Disclosed is a process for the production of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) which includes reacting a propane feedstock comprising tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, or a mixture thereof, in the presence of a solid catalyst. The process generally comprises the following four steps: (i) providing a propane feedstock comprising trichlorodifluoropropanes and dichlorotrifluoropropanes, (ii) reacting the feedstock in a vapor phase reactor in the presence of HF and in the presence of a solid catalyst under conditions effective to form a product stream comprising HCFO-1233zd and unconverted starting materials, (iii) recovering or removing HCl and HF, and (iv) isolating HCFO-1233zd(E), HCFO-1233zd(Z), or both.
    Type: Grant
    Filed: April 1, 2016
    Date of Patent: September 19, 2017
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Stephen A. Cottrell
  • Patent number: 9650320
    Abstract: Disclosed are processes for a high temperature isomerization reaction converting (E)-1-chloro-3,3,3-trifluoropropene to (Z)-1-chloro-3,3,3-trifluoropropene. In certain aspects of the invention, such a process includes contacting a feed stream with a heated surface, where the feed stream includes (E)-1-chloro-3,3,3-trifluoropropene or mixture of (E)-1-chloro-3,3,3-trifluoropropene with (Z)-1-chloro-3,3,3-trifluoropropene. The resulting product stream includes (Z)-1-chloro-3,3,3-trifluoropropene and (E)-1-chloro-3,3,3-trifluoropropene, where the ratio of (Z) isomer to (E) isomer in the product stream is higher than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.
    Type: Grant
    Filed: October 19, 2015
    Date of Patent: May 16, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9346723
    Abstract: The invention concerns a method for producing 2,3,3,3-tetrafluoropropene comprising: a fluoridation reaction of a halopropane and/or halopropene into 2,3,3,3-tetrafluoropropene by means of hydrogen fluoride; the recovery of a gas stream resulting from the reaction; the cooling and partial condensation of the gas stream resulting from the reaction into a partially condensed stream; the separation of the partially condensed stream into a gas fraction and a liquid fraction; the compression of the gas fraction into a compressed gas fraction; the compression of the liquid fraction into a compressed liquid fraction; the distillation of the compressed gas fraction and compressed liquid fraction in order to provide a stream of 2,3,3,3-tetrafluoropropene, a stream of hydrochloric acid, and a stream of unreacted hydrogen fluoride. The invention also concerns an installation suitable for implementing said method.
    Type: Grant
    Filed: January 11, 2013
    Date of Patent: May 24, 2016
    Assignee: Arkema France
    Inventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
  • Patent number: 9328042
    Abstract: The present invention provides an efficient and cost effect synthesis route from a specific starting material of 2,3-dichloro-1,3-butadiene to the desired product of Z-1,1,1,4,4,4-hexafluoro-2-butene.
    Type: Grant
    Filed: July 30, 2015
    Date of Patent: May 3, 2016
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Sheng Peng, Andrew Jackson, Mario Joseph Nappa
  • Patent number: 9255046
    Abstract: Disclosed is a method for forming HFO-1234ze, and for forming compositions comprising HFO-1234ze, by (a) converting, preferably by dehydrofluorination, pentafluorpropane (HFC-245), preferably 1,1,1,3,3-pentafluorpropane (HFC-245fa), preferably by contact with a caustic solution, to a reaction product comprising cis-HFO-1234ze and trans-HFO-1234ze; and (b) contacting at least a portion, preferably substantially portion, and in certain embodiments substantially all of said reaction product with at least one isomerization catalyst to convert at least a portion, and preferably at least a substantial portion, of cis-HFO-1234ze in said reaction product to trans-HFO-1234ze.
    Type: Grant
    Filed: May 21, 2008
    Date of Patent: February 9, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Haiyou Wang, Yuon Chiu, Gustavo Cerri
  • Patent number: 9212109
    Abstract: Disclosed is a process involving contacting a hydrohalobutane selected from the group consisting of CF2HCHClCH2CCl2H, CF3CHClCH2CCl2H, CF3CHClCH2CCl3, CF3CClHCHFCCl2H and CF3CClHCHFCCl3, with HF in a reaction zone in the presence of an antimony halide catalyst selected from SbCl5 and SbF5 to form a first product mixture containing a hydromonochlorofluorobutane. Also disclosed is a process involving contacting a hydrohalopentane selected from the group consisting of CF2HCHClCH2CX2CX3 and CF3CHClCH2CX2CX3, wherein each X is independently selected from the group consisting of F and Cl, and not all X are fluorines, with HF in a reaction zone in the presence of an antimony halide catalyst selected from SbCl5 and SbF5 to form a first product mixture containing a hydromonochlorofluoropentane. A compound of the formula CF3CHClCH2CHF2 is also disclosed.
    Type: Grant
    Filed: October 5, 2012
    Date of Patent: December 15, 2015
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventor: Ekaterina N Swearingen
  • Publication number: 20150112103
    Abstract: A method for producing 1234Z from 1234E while generation of 245fa as a byproduct is suppressed. The method for producing cis-1,3,3,3-tetrafluoropropene includes putting trans-1,3,3,3-tetrafluoropropene into contact with a catalyst. The trans-1,3,3,3-tetrafluoropropene is put into contact with the catalyst at a reaction temperature of higher than or equal to 200° C. and lower than or equal to 550° C. for a contact time of longer than or equal to 0.01 seconds and shorter than or equal to 500 seconds.
    Type: Application
    Filed: December 26, 2014
    Publication date: April 23, 2015
    Inventors: Satoru OKAMOTO, Naoto TAKADA, Fuyuhiko SAKYU, Takamasa KITAMOTO, Takuya TONOMURA, Masatomi KANAI
  • Publication number: 20150099907
    Abstract: A method for producing a desired isomer of 1-chloro-3,3,3-trifluoro-1-propene or a desired isomer of 1,3,3,3-tetrafluoropropene at a high conversion ratio with no use of a solid catalyst is provided. Since no solid catalyst is used, a desired isomer of 1-chloro-3,3,3-trifluoro-1-propene and a desired isomer of 1,3,3,3-tetrafluoropropene can be stably obtained with no undesired possibility that the solid catalyst is deteriorated due to coking or the like caused as a result of long-time use thereof.
    Type: Application
    Filed: December 9, 2014
    Publication date: April 9, 2015
    Inventors: Hideaki IMURA, Satoru OKAMOTO, Masamune OKAMOTO, Naoto TAKADA, Fuyuhiko SAKYU
  • Patent number: 9000239
    Abstract: The present invention provides processes for the production of HCFO-1233zd, 1-chloro-3,3,3-trifluoropropene, from the starting material, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf). In a first process, HCFO-1233zd is produced by the isomerization of HCFO-1233xf. In a second process, HCFO-1233zd is produced in a two-step procedure which includes (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne; and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 7, 2015
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8987535
    Abstract: The invention also relates a process for the manufacture of trans 1-chloro3,3,3-trifluoropropene. The process comprises an isomerization step from cis 1233zd to trans 1233zd.
    Type: Grant
    Filed: February 19, 2014
    Date of Patent: March 24, 2015
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Anne Pigamo, Sri R. Seshadri
  • Patent number: 8987534
    Abstract: The invention also relates a process for the manufacture of trans 1-chloro3,3,3-trifluoropropene. The process comprises an isomerization step from cis 1233zd to trans 1233zd.
    Type: Grant
    Filed: January 29, 2014
    Date of Patent: March 24, 2015
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer, Sri R. Seshadri
  • Patent number: 8895788
    Abstract: The invention relates to a process for manufacturing 1,1,1,2-tetrafluoropropene (1234yf, CF3—CF?CH2) from 1,1,3,3-tetrachlororopropene (1230za, CCl2?CH—CHCl2) and/or 1,1,1,3,3-pentachloropropane (240fa, CCl3CH2CHCl2). The process comprises a step of isomerization of 1,1,3,3-tetrafluoropropene (1230za) to 1,1,2,3-tetrachloropropene (1230xa) followed by conversion of the 1,1,2,3-tetrachloropropene (1230xa) to 1,1,1,2-tetrafluoropropene (1234yf) via a hydrofluorination process.
    Type: Grant
    Filed: January 21, 2014
    Date of Patent: November 25, 2014
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
  • Publication number: 20140336424
    Abstract: Provided is a method for producing trans-1-chloro-3,3,3-trifluoropropene usable as a raw material for a foaming agent for a hard polyurethane foam, a solvent, a cleaning agent, a cooling medium, a working fluid, a propellant, a fluorinated resin, etc., the method involving a step of bringing cis-1-chloro-3,3,3-trifluoropropene into contact with a catalyst, wherein the catalyst includes a fluorinated metal oxide or a metal fluoride each produced by applying a fluorination treatment to a metal oxide containing one kind or two or more kinds of metals and containing aluminum atoms that make up 50 at. % or more of metal atoms to thereby substitute some or all of oxygen atoms in the metal oxide with fluorine atom(s), wherein the fluorinated metal oxide or the metal fluoride is a compound produced through a drying treatment at 400 to 600° C.
    Type: Application
    Filed: November 8, 2012
    Publication date: November 13, 2014
    Inventors: Satoru Okamoto, Fuyuhiko Sakyu
  • Publication number: 20140288336
    Abstract: Disclosed are processes for a high temperature isomerization reaction converting (E)-1-chloro-3,3,3-trifluoropropene to (Z)-1-chloro-3,3,3-trifluoropropene. In certain aspects of the invention, such a process includes contacting a feed stream with a heated surface, where the feed stream includes (E)-1-chloro-3,3,3-trifluoropropene or mixture of (E)-1-chloro-3,3,3-trifluoropropene with (Z)-1-chloro-3,3,3-trifluoropropene. The resulting product stream includes (Z)-1-chloro-3,3,3-trifluoropropene and (E)-1-chloro-3,3,3-trifluoropropene, where the ratio of (Z) isomer to (E) isomer in the product stream is higher than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 25, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung
  • Publication number: 20140275644
    Abstract: The present invention discloses methods to produce cis-1-chloro-3,3,3-trifluoropropene in high yield by the isomerization of trans-1-chloro-3,3,3-trifluoropropene. These isomers are also known as 1233zd(Z) and 1233zd(E), respectively. This is done by using reactive distillation whereby as cis-1-chloro-3,3,3-trifluoropropene is produced, it is removed from the reaction zone. This product removal causes a shift in the thermodynamic equilibrium of the reaction system, forcing the production of additional cis isomer.
    Type: Application
    Filed: March 14, 2013
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski
  • Patent number: 8822739
    Abstract: An isomerization process is disclosed. The process involves contacting 2,3,3,3-tetrafluoropropene with a suitable catalyst in a reaction zone to produce a product mixture comprising 1,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: March 6, 2013
    Date of Patent: September 2, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventor: Mario Joseph Nappa
  • Publication number: 20140206910
    Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system including one or more reactors for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.
    Type: Application
    Filed: March 4, 2014
    Publication date: July 24, 2014
    Applicant: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung
  • Publication number: 20140171698
    Abstract: The invention also relates a process for the manufacture of trans 1-chloro 3,3,3-trifluoropropene. The process comprises an isomerization step from cis 1233zd to trans 1233zd.
    Type: Application
    Filed: February 19, 2014
    Publication date: June 19, 2014
    Applicant: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Anne Pigamo, Sri R. Seshadri
  • Patent number: 8742181
    Abstract: A process for isomerizing a (hydrohalo)fluoroalkene, the process comprising contacting the (hydrohalo)fluoroalkene with a catalyst a catalyst which is a chromia-containing catalyst supported on AlF3 or fluorinated alumina.
    Type: Grant
    Filed: November 21, 2012
    Date of Patent: June 3, 2014
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew Paul Sharratt, John Charles McCarthy
  • Patent number: 8653309
    Abstract: Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.
    Type: Grant
    Filed: April 20, 2011
    Date of Patent: February 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8642818
    Abstract: The invention relates to a process for manufacturing 1,1,1,2-tetrafluoropropene (1234yf, CF3—CF?CH2) from 1,1,3,3-tetrachlororopropene (1230za, CCl2?CH—CHCl2) and/or 1,1,1,3,3-pentachloropropane (240fa, CCl3CH2CHCl2). The process comprises an isomerization step of 1-chloro-3,3,3 trifluoropropene (1233zd, CF3—CH?CHCl) to 2-chloro-3,3,3 trifluoropropene (1233xf or CF3—CCl?CH2).
    Type: Grant
    Filed: November 12, 2009
    Date of Patent: February 4, 2014
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
  • Patent number: 8642820
    Abstract: To provide a process to produce 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO-1214ya) simply and economically without requiring purification of 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) from the raw material component obtained as a mixture of isomers, i.e. dichloropentafluoropropane (HCFC-225) including HCFC-225ca and at the same time to produce simply and economically 2,3,3,3-tetrafluoropropene (HFO-1234yf) from 1-chloro-2,3,3,3-tetrafluoropropane (HCFC-244eb). A raw material composition comprising HCFC-244eb and HCFC-225 including HCFC-225ca is contacted with an alkali aqueous solution in the presence of a phase-transfer catalyst to produce CFO-1214ya from HCFC-225ca and at the same time to produce HFO-1234yf from HCFC-244eb.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: February 4, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Ryuji Seki, Hidekazu Okamoto, Hirokazu Takagi, Satoshi Kawaguchi
  • Patent number: 8642819
    Abstract: The present invention provides a process for the manufacture of trans 1-chloro-3,3,3-trifluoropropene (E-1233zd). The first step of the process comprises the fluorination of 1,1,3,3-tetrachlororopropene (1230za, CCh?CH—CHCh) and/or 1,1,1,3,3-pentaachloropropane (240fa) to a mixture of cis 1233zd (Z-1233zd) and trans 1233zd (E-1233zd). The second step of the process comprises a separation of the mixture formed in the first step to isolate cis 1233zd (Z-1233zd) from the mixture. The third step of the process comprises isomerization of cis 1233zd (Z-1233zd) to trans 1233zd (E-1233zd).
    Type: Grant
    Filed: November 12, 2009
    Date of Patent: February 4, 2014
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
  • Patent number: 8609908
    Abstract: To provide a process for producing, at a high content ratio, 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO1214ya). The process for producing HCFC-225ca of the present invention comprises subjecting a raw material composed of dichloropentafluoropropane (HCFC-225) including 2,2-dichloro-1,1,1,3,3-pentafluoropropane (HCFC225aa) to an isomerization reaction at a temperature of at most 290° C. in a gas phase in the presence of a metal oxide catalyst thereby to isomerize HCFC-225aa to HCFC-225ca.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: December 17, 2013
    Assignee: Asahi Glass Company, Limited
    Inventor: Hidekazu Okamoto
  • Publication number: 20130310614
    Abstract: The present invention provides processes for the production of HCFO-1233zd, 1-chloro-3,3,3-trifluoropropene, from the starting material, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf). In a first process, HCFO-1233zd is produced by the isomerization of HCFO-1233xf. In a second process, HCFO-1233zd is produced in a two-step procedure which includes (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne; and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd.
    Type: Application
    Filed: March 14, 2013
    Publication date: November 21, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20130261353
    Abstract: Disclosed is an integrated manufacturing process to co-produce (E) 1-chloro-3,3,3-trifluoropropene, (E) 1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single starting feed material or a mixture of unsaturated hydrochloro-carbon feed materials comprising 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloro-propene. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E) 1-chloro-3,3,3-trifluoro-propene (1233zd (E)) from these feed materials, which may also include 240fa. In the second liquid phase fluorination reactor 1233zd (E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E) 1,3,3,3-tetrafluoro-propene (1234ze (E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst.
    Type: Application
    Filed: March 28, 2012
    Publication date: October 3, 2013
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20130253234
    Abstract: An isomerization process is disclosed. The process involves contacting 2,3,3,3-tetrafluoropropene with a suitable catalyst in a reaction zone to produce a product mixture comprising 1,3,3,3-tetrafluoropropene.
    Type: Application
    Filed: March 6, 2013
    Publication date: September 26, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: Mario Joseph Nappa
  • Patent number: 8513473
    Abstract: There is provided a method for producing trans-1,3,3,3-tetrafluoropropene, which includes the step of bringing cis-1,3,3,3-tetrafluoropropene into contact, in a gas phase, with a metal oxide, an activated carbon supporting thereon a metal compound, or a fluorinated derivative thereof, as a catalyst.
    Type: Grant
    Filed: October 7, 2008
    Date of Patent: August 20, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Fuyuhiko Sakyu, Satoru Okamoto, Yasuo Hibino
  • Publication number: 20130158304
    Abstract: An object is to provide a method for producing 1,1,1,4,4,4-hexafluoro-2-butene with high efficiency, which is suitable for a flow reaction, and cis-1,1,1,4,4,4-hexafluoro-2-butene can be efficiently obtained when isomerization of hexafluoro-1,3-butadiene is conducted using a catalyst and the resultant mixture is successively subjected to catalytic hydrogenation to produce cis-1,1,1,4,4,4-hexafluoro-2-butene, wherein the whole process is performed by a flow catalytic reaction.
    Type: Application
    Filed: June 13, 2011
    Publication date: June 20, 2013
    Inventors: Heng-dao Quan, Masanori Tamura, Junji Mizukado, Akira Sekiya
  • Publication number: 20130150632
    Abstract: Disclosed is a process for the preparation of cis-1-chloro-3,3,3-trifluoropropene (cis-1233zd) comprising the steps of (a) providing CF3CHClCHCl2 (233da), and (b) treating the 233da with a dechlorinating agent to produce a mixture of compounds including cis-1-chloro-3,3,3-trifluoropropene, preferably wherein the amount of the cis-isomer generated in the reaction is not less than 30%.
    Type: Application
    Filed: November 12, 2012
    Publication date: June 13, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: Honeywell International Inc.
  • 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: 8436217
    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: Grant
    Filed: April 25, 2011
    Date of Patent: May 7, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • 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: 8410324
    Abstract: A process for isomerising a (hydrohalo)fiuoroalkene, the process comprising contacting the (hydrohalo)fluoroalkene with a catalyst comprising an unsupported Lewis acid, a chromia-containing catalyst containing at least one additional metal, an alumina, a supported liquid catalyst, and mixtures thereof.
    Type: Grant
    Filed: April 11, 2008
    Date of Patent: April 2, 2013
    Assignee: Mexichem Amanco Holding, S.A. de C.V.
    Inventors: Andrew Paul Sharratt, John Charles McCarthy
  • Publication number: 20130079562
    Abstract: A process for isomerising a (hydrohalo)fluoroalkene, the process comprising contacting the (hydrohalo)fluoroalkene with a catalyst a catalyst which is a chromia-containing catalyst supported on AlF3 or fluorinated alumina.
    Type: Application
    Filed: November 21, 2012
    Publication date: March 28, 2013
    Inventors: ANDREW PAUL SHARRATT, John Charles McCarthy
  • 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: 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
  • Publication number: 20120271069
    Abstract: Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.
    Type: Application
    Filed: April 20, 2011
    Publication date: October 25, 2012
    Inventors: Haiyou Wang, 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