Utilizing Unsaturated Compound Patents (Class 570/175)
  • Patent number: 10364201
    Abstract: In certain aspects, the present invention relates to methods for increasing the cost efficiency and safety of the hydrogenation of a fluorinated olefin by controlling the reaction conditions and parameters. In further aspects, the hydrogenation reaction is provided in a two stage reaction wherein the reactant amounts, temperature and other parameters are controlled such that the conversion percentage, selectivity, and reaction parameters are all within commercially acceptable levels.
    Type: Grant
    Filed: March 21, 2016
    Date of Patent: July 30, 2019
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Stephen A. Cottrell, John J. Senetar, Hsueh S. Tung, Daniel C. Merkel, Yuon Chiu, Haluk Kopkalli
  • Patent number: 10125066
    Abstract: A method for producing 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from a reaction composition including a mixture of HCFC-244bb and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) by selectively hydrogenating the HCFO-1233xf component of the mixture in a vapor phase in the presence of hydrogen gas and a catalyst to generate a product composition including unreacted HCFC-244bb and hydrogenation products of HCFO-1233xf, such as 2-chloro-1,1,1-trifluoropropane (HCFC-253db), which may be separated from the HCFC-244bb by distillation. The separated HCFC-244bb may then be purified by subsequent acid neutralization and drying steps.
    Type: Grant
    Filed: November 29, 2017
    Date of Patent: November 13, 2018
    Assignee: Honeywell International Inc.
    Inventors: Christian Jungong, Daniel C. Merkel
  • Patent number: 9856192
    Abstract: A method for preparing 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene, including: providing a first reactor including a first section, a second section, and a third section, with each section being filled with different catalysts, preheating hexafluoropropylene and hydrogen, and introducing the hexafluoropropylene and the hydrogen to the first reactor to yield a first mixture including: 1,1,1,2,3-pentafluoropropane, 1,1,1,2,3,3-hexafluoropropane, and hydrogen fluoride; introducing the first mixture to a first distillation column to yield 1,1,1,2,3,3-hexafluoropropane at a top of the first distillation column and 1,1,1,2,3-pentafluoropropane and hydrogen fluoride at a bottom of the first distillation column, recycling the 1,1,1,2,3,3-hexafluoropropane to a lower part of the first section of the first reactor, and introducing the 1,1,1,2,3-pentafluoropropane and the hydrogen fluoride to a second reactor to yield a second mixture including: 2,3,3,3-tetrafluoropropene, 1,3,3,3-tetrafluoropropene, hydr
    Type: Grant
    Filed: January 12, 2017
    Date of Patent: January 2, 2018
    Assignees: ZHEJIANG QUZHOU JUXIN FLUORINE CHEMICAL CO., LTD., ZHEJIANG QUHUA FLUOR-CHEMISTRY CO., LTD.
    Inventors: Jun Lei, Aiguo Wang, Bo Yang, Yan Zhang, Huadong Zhou, Yang Zhao, Guoan Liu, Yi Zhu, Gang Su
  • Patent number: 9758455
    Abstract: Object: An object of the present invention is to provide a method for producing, with a high yield, a fluorinated organic compound, the fluorinated organic compound having not been produced with a sufficient yield by a conventional method for producing a fluorinated organic compound using a fluorinating agent containing IF5-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent. Means for achieving the object: A method for producing a fluorinated organic compound comprising step A of fluorinating an organic compound by bringing the organic compound into contact with (1) IF5-pyridine-HF and (2) at least one additive selected from the group consisting of amine hydrogen fluorides, XaF (wherein Xa represents hydrogen, potassium, sodium, or lithium), oxidizers, and reducing agents.
    Type: Grant
    Filed: April 1, 2015
    Date of Patent: September 12, 2017
    Assignees: DAIKIN INDUSTRIES, LTD., NATIONAL UNIVERSITY CORPORATION HOKKAIDO UNIVERSITY
    Inventors: Masahiro Higashi, Yosuke Kishikawa, Atsushi Shirai, Takashi Namikawa, Sumi Ishihara, Shoji Hara
  • Patent number: 9675950
    Abstract: The present invention is directed to a combination reactor system for exothermic reactions comprising a trickle-bed reactor and a shell-and-tube reactor. This combination allows the system to efficiently remove heat while also providing the ability to control both the temperature and/or reaction progression. The trickle-bed reactor removes heat efficiently from the system by utilizing latent heat and does not require the use of a cooling or heating medium. The shell-and-tube reactor is used to further progress the reaction and provides a heat exchanger in order to introduce fluid at the desired temperature in the shell-and-tube reactor. Also, additional reactant or reactants and/or other fluids may be introduced to the shell-and-tube section of the reactor under controlled temperature conditions.
    Type: Grant
    Filed: January 26, 2015
    Date of Patent: June 13, 2017
    Assignee: Honeywell International Inc.
    Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
  • Patent number: 9598336
    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: May 16, 2012
    Date of Patent: March 21, 2017
    Assignee: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Patricia Cheung, Allen Capron Sievert, Concetta Lamarca
  • Patent number: 9302964
    Abstract: To provide a method for efficiently separating 2,3,3,3-tetrafluoropropene (HFO-1234yf) and chloromethane (R40) from a composition containing HFO-1234yf and R40. A method for separating HFO-1234yf containing substantially no R40, which comprises bringing an azeotropic composition or azeotrope-like composition of H FO-1234yf and R40 into contact with a specific extraction solvent.
    Type: Grant
    Filed: June 25, 2015
    Date of Patent: April 5, 2016
    Assignee: Asahi Glass Company, Limited
    Inventors: Shoji Furuta, Tetsuo Otsuka
  • Patent number: 9290424
    Abstract: In certain aspects, the present invention relates to methods for increasing the cost efficiency and safety of the hydrogenation of a fluorinated olefin by controlling the reaction conditions and parameters. In further aspects, the hydrogenation reaction is provided in a two stage reaction wherein the reactant amounts, temperature and other parameters are controlled such that the conversion percentage, selectivity, and reaction parameters are all within commercially acceptable levels.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: March 22, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Stephen A. Cottrell, John J. Senetar, Hsueh S. Tung, Daniel C. Merkel, Yuon Chiu, Haluk Kopkalli
  • Patent number: 9266800
    Abstract: A trifluoroethylene composition which is safe to handle and which can be safely stored and transported at pressures of up to 5.00 MPa. The composition comprises trifluoroethylene and HCl in a molar ratio trifluoroethylene:HCl from 10:90 to 63:37. When the composition is a compressed gas it has a pressure of from 0.50 to 5.00 MPa.
    Type: Grant
    Filed: January 31, 2013
    Date of Patent: February 23, 2016
    Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventor: Emanuela Antenucci
  • Publication number: 20150126785
    Abstract: The invention provides a process comprising contacting (1243zf) or (253fb) with hydrogen in the presence of a hydrogenation catalyst to produce a composition comprising 1,1,1-trifluoropropane (263fb).
    Type: Application
    Filed: July 18, 2012
    Publication date: May 7, 2015
    Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.
    Inventors: Andrew P. Sharratt, Claire Elizabeth Mcguinness, Emma Jane Hodgson
  • Patent number: 8969634
    Abstract: The present invention is directed to a combination reactor system for exothermic reactions comprising a trickle-bed reactor and a shell-and-tube reactor. This combination allows the system to efficiently remove heat while also providing the ability to control both the temperature and/or reaction progression. The trickle-bed reactor removes heat efficiently from the system by utilizing latent heat and does not require the use of a cooling or heating medium. The shell-and-tube reactor is used to further progress the reaction and provides a heat exchanger in order to introduce fluid at the desired temperature in the shell-and-tube reactor. Also, additional reactant or reactants and/or other fluids may be introduced to the shell-and-tube section of the reactor under controlled temperature conditions.
    Type: Grant
    Filed: September 26, 2011
    Date of Patent: March 3, 2015
    Assignee: Honeywell International Inc.
    Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
  • Patent number: 8957264
    Abstract: A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.
    Type: Grant
    Filed: December 11, 2013
    Date of Patent: February 17, 2015
    Assignee: Asahi Glass Company, Limited
    Inventors: Shoji Furuta, Yusuke Sugahara, Keiko Nakase, Keisuke Mori
  • Patent number: 8952209
    Abstract: A method and apparatus for method of continuously producing 1,1,1,2,3-pentafluoropropane with high yield is provided. The method includes (a) bringing a CoF3-containing cobalt fluoride in a reactor into contact with 3,3,3-trifluoropropene to produce a CoF2-containing cobalt fluoride and 1,1,1,2,3-pentafluoropropane, (b) transferring the CoF2-containing cobalt fluoride in the reactor to a regenerator and bringing the transferred CoF2-containing cobalt fluoride into contact with fluorine gas to regenerate a CoF3-containing cobalt fluoride, and (c) transferring the CoF3-containing cobalt fluoride in the regenerator to the reactor and employing the transferred CoF3-containing cobalt fluoride in Operation (a). Accordingly, the 1,1,1,2,3-pentafluoropropane can be continuously produced with high yield from the 3,3,3-trifluoropropene using a cobalt fluoride (CoF2/CoF3) as a fluid catalyst, thereby improving the reaction stability and readily adjusting the optimum conversion rate and selectivity.
    Type: Grant
    Filed: March 13, 2013
    Date of Patent: February 10, 2015
    Assignee: Foosung Co., Ltd.
    Inventors: ook jae Cho, Jae Kug Ryu, Bong Seok Kim, Donghyun Kim, Byounghun Park, su jin Park, Jin-A Jung, Daewoo Kim
  • Patent number: 8946493
    Abstract: The present invention relates to a method for producing 1,2,3,3,3-pentafluoropropane, involving reacting gaseous phase 1,2,3,3,3-pentafluoropropene with hydrogen in a superstoichimetric amount in the presence of a hydrogenation catalyst in a reactor, and recirculating a part of the gaseous effluent from the reactor.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: February 3, 2015
    Assignee: Arkema France
    Inventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini
  • Patent number: 8921623
    Abstract: A process for the production of fluorinated alkanes by contacting a feed stream containing a fluorinated olefin and a reducing agent, preferably with a first amount of catalyst to produce a fluorinated alkane, at a first conversion level, wherein a first effluent stream contains unreacted fluorinated olefin and reducing agent; and contacting the first effluent stream under conditions effective to produce a higher level of conversion than said conversion level.
    Type: Grant
    Filed: February 25, 2011
    Date of Patent: December 30, 2014
    Assignee: Honeywell Industrial Inc.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Scheidle, Kevin D. Uhrich
  • Patent number: 8912370
    Abstract: The present invention relates to a method for producing 1,1,1,2,3,3-hexaafluoropropane, involving reacting gaseous phase hexafluoropropene with hydrogen in a superstoichimetric amount in the presence of a hydrogenation catalyst in a reactor, and recirculating a part of the gaseous effluent from the reactor.
    Type: Grant
    Filed: May 5, 2010
    Date of Patent: December 16, 2014
    Assignee: Arkema France
    Inventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini
  • 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
  • Patent number: 8853473
    Abstract: The present invention provides a process for producing 2,3,3,3-tetrafluoropropene, comprising distilling a mixture of water and 2,3,3,3-tetrafluoropropene to separate the mixture into a first stream and a second stream, the first stream containing 2,3,3,3-tetrafluoropropene with a water content higher than the original mixture, and the second stream containing 2,3,3,3-tetrafluoropropene with a water content lower than the original mixture; and obtaining 2,3,3,3-tetrafluoropropene with a reduced water content from the second stream. The process of the invention can efficiently remove water from 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: August 21, 2009
    Date of Patent: October 7, 2014
    Assignee: Daikin Industries, Ltd.
    Inventor: Kazuhiro Takahashi
  • Patent number: 8729321
    Abstract: A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state is under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.
    Type: Grant
    Filed: April 19, 2006
    Date of Patent: May 20, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Shoji Furuta, Yu{grave over (s)}uke Sugahara, Keiko Nakase, Keisuke Mori
  • Publication number: 20140135538
    Abstract: A method and apparatus for method of continuously producing 1,1,1,2,3-pentafluoropropane with high yield is provided. The method includes (a) bringing a CoF3-containing cobalt fluoride in a reactor into contact with 3,3,3-trifluoropropene to produce a CoF2-containing cobalt fluoride and 1,1,1,2,3-pentafluoropropane, (b) transferring the CoF2-containing cobalt fluoride in the reactor to a regenerator and bringing the transferred CoF2-containing cobalt fluoride into contact with fluorine gas to regenerate a CoF3-containing cobalt fluoride, and (c) transferring the CoF3-containing cobalt fluoride in the regenerator to the reactor and employing the transferred CoF3-containing cobalt fluoride in Operation (a). Accordingly, the 1,1,1,2,3-pentafluoropropane can be continuously produced with high yield from the 3,3,3-trifluoropropene using a cobalt fluoride (CoF2/CoF3) as a fluid catalyst, thereby improving the reaction stability and readily adjusting the optimum conversion rate and selectivity.
    Type: Application
    Filed: March 13, 2013
    Publication date: May 15, 2014
    Applicant: FOOSUNG CO., LTD.
    Inventors: ook jae Cho, Jae Kug Ryu, Bong Seok Kim, Donghyun Kim, Byounghun Park, Su Jin Park, Jin-A Jung, Daewoo Kim
  • Publication number: 20140088328
    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: Application
    Filed: May 16, 2012
    Publication date: March 27, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Patricia Cheung, Allen Capron Sievert, Concetta Lamarca
  • Patent number: 8623233
    Abstract: Azeotropic or azeotrope-like compositions are disclosed. The azeotropic or azeotrope-like compositions are mixtures of Z-1,1,1,4,4,4-hexafluoro-2-butene, trans-1,2-dichloroethylene and 1,1,1,3,3-pentafluorobutane. Also disclosed is a process of preparing a thermoplastic or thermoset foam by using such azeotropic or azeotrope-like compositions as blowing agents. Also disclosed is a process of producing refrigeration by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as solvents. Also disclosed is a process of producing an aerosol product by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as heat transfer media. Also disclosed is a process of extinguishing or suppressing a fire by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as dielectrics.
    Type: Grant
    Filed: January 10, 2011
    Date of Patent: January 7, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mark L. Robin, Joan Ellen Bartelt
  • Patent number: 8618339
    Abstract: Disclosed is a method for the synthesis of fluorinated alkenes comprising contacting a fluorinated alkyne of the formula R1 C?C R2, wherein R1 and R2 are independently selected from CF3, C2F5, C3F7, and C4F9, in a pressure vessel, with a Lindlar catalyst, with substantially one molar equivalent of hydrogen, to make the corresponding cis-alkene of formula R1 C?C R2 with high selectivity, wherein said hydrogen is added in portions over a period of time, so as to produce an initial pressure in the pressure in the vessel of no more than about 100 psi.
    Type: Grant
    Filed: April 28, 2008
    Date of Patent: December 31, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventor: Ekaterina N. Swearingen
  • Publication number: 20130225882
    Abstract: An alpha-alumina support for a hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.
    Type: Application
    Filed: April 4, 2013
    Publication date: August 29, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: HONEYWELL INTERNATIONAL INC.
  • Publication number: 20130172577
    Abstract: A process for producing a ringlike oxidic shaped body by mechanically compacting a pulverulent aggregate introduced into the fill chamber of a die, wherein the outer face of the resulting compact corresponds to that of a frustocone.
    Type: Application
    Filed: February 28, 2013
    Publication date: July 4, 2013
    Applicant: BASF SE
    Inventor: BASF SE
  • Patent number: 8471078
    Abstract: A method of providing a blend of tetra- and/or pentafluoroalkanes comprising hydrogenating a pentafluoropropene.
    Type: Grant
    Filed: January 23, 2009
    Date of Patent: June 25, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Robert E. Low, Andrew P. Sharratt
  • 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
  • Publication number: 20130102815
    Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the
    Type: Application
    Filed: December 12, 2012
    Publication date: April 25, 2013
    Applicant: Mexichem Amanco Holding S.A. de C.V.
    Inventor: Mexichem Amanco Holding S.A. de C.V.
  • Patent number: 8426657
    Abstract: The present invention relates to compositions and processes of using perfluoropolyether to maintain or improve the oil return, lubrication, cooling capacity, or energy efficiency of a refrigeration, air conditioning or heat transfer system.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: April 23, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Thomas J. Leck, Thomas Frank Saturno, Gregory A. Bell
  • Publication number: 20130079563
    Abstract: The present invention is directed to a combination reactor system for exothermic reactions comprising a trickle-bed reactor and a shell-and-tube reactor. This combination allows the system to efficiently remove heat while also providing the ability to control both the temperature and/or reaction progression. The trickle-bed reactor removes heat efficiently from the system by utilizing latent heat and does not require the use of a cooling or heating medium. The shell-and-tube reactor is used to further progress the reaction and provides a heat exchanger in order to introduce fluid at the desired temperature in the shell-and-tube reactor. Also, additional reactant or reactants and/or other fluids may be introduced to the shell-and-tube section of the reactor under controlled temperature conditions.
    Type: Application
    Filed: September 26, 2011
    Publication date: March 28, 2013
    Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
  • Patent number: 8404907
    Abstract: Disclosed is a process for making one isomer of CF3CH?CHCl. More particularly, the invention comprises the production of CF3C?CCl and its selective reduction to cis-1-chloro-3,3,3-trifluoropropene (CF3CH?CHCl).
    Type: Grant
    Filed: February 18, 2011
    Date of Patent: March 26, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Andrew Joseph Poss, Rajiv Ratna Singh, Michael Van Der Puy, Ryan J. Hulse
  • Publication number: 20130006022
    Abstract: The present invention provides a method for producing a fluorine-containing alkane, which comprises reacting at least one fluorine-containing compound selected from the group consisting of chlorine-containing fluoroalkanes and fluorine-containing alkenes with hydrogen gas in the presence of catalysts, wherein two or more catalysts having different catalytic activities are used, and the fluorine-containing compound and hydrogen gas, which are starting materials, are sequentially brought into contact with the catalysts in the order of the catalyst having a lower catalytic activity followed by the catalyst having a higher catalytic activity. According to the present invention, in the method for producing a fluorine-containing alkane by using chlorine-containing fluoroalkane or fluorine-containing alkene as a starting material, and subjection it to a reduction reaction or a hydrogen addition reaction, the objective fluorine-containing alkane can be produced with high productivity.
    Type: Application
    Filed: February 18, 2011
    Publication date: January 3, 2013
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Yuko Shiotani, Kakeru Hanabusa, Takehiro Chaki, Kazuhiro Takahashi
  • 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
  • Publication number: 20120178978
    Abstract: A support of metal oxyfluoride or metal halide for a metal-based hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.
    Type: Application
    Filed: March 20, 2012
    Publication date: July 12, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HAIYOU WANG, HSUEH S. TUNG
  • Publication number: 20120101315
    Abstract: The present invention relates to a method for producing 1,2,3,3,3-pentafluoropropane, involving reacting gaseous phase 1,2,3,3,3-pentafluoropropene with hydrogen in a superstoichimetric amount in the presence of a hydrogenation catalyst in a reactor, and recirculating a part of the gaseous effluent from the reactor.
    Type: Application
    Filed: May 6, 2010
    Publication date: April 26, 2012
    Applicant: Arkema France
    Inventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini
  • Publication number: 20120101314
    Abstract: The present invention relates to a method for producing 1,1,1,2,3,3-hexaafluoropropane, involving reacting gaseous phase hexafluoropropene with hydrogen in a superstoichimetric amount in the presence of a hydrogenation catalyst in a reactor, and recirculating a part of the gaseous effluent from the reactor.
    Type: Application
    Filed: May 5, 2010
    Publication date: April 26, 2012
    Applicant: Arkema France
    Inventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini
  • Publication number: 20120065437
    Abstract: The instant invention relates to a process and method for manufacturing 2,3,3,3-tetrafluoropropene by dehydrohalogenating a reactant stream of 2-chloro-1,1,1,2-tetrafluoropropane that is substantially free from impurities, particularly halogenated propanes, propenes, and propynes.
    Type: Application
    Filed: October 25, 2011
    Publication date: March 15, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Haiyou Wang
  • Patent number: 8129574
    Abstract: Disclosed is a process and apparatus for the catalytic hydrogenation of fluoroolefins to fluorocarbons where the reaction is carried out in a multi-tube shell and tube reactor. Reactions involving hydrogenation of fluoro-olefins are typically exothermic. In commercial processes where a fluoro-olefin C(n)H(2n?x)F(x) to C(n)H(2n?x+2)F(x) is hydrogenated (e.g. hexafluoropropylene to 236ea, 1225ye to 245eb, and the like), inadequate management or control of heat removal may induce excess hydrogenation, decomposition and hot spots resulting in reduced yields and potential safety issues. In the hydrogenation of fluoro-olefins, it is therefore necessary to control the reaction temperature as precisely as practical to overcome challenges associated with heat management and safety.
    Type: Grant
    Filed: August 31, 2009
    Date of Patent: March 6, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Orlando George Rodrigues, Gus Cerri, Hsueh Sung Tung, Stephen A. Cottrell
  • Publication number: 20110259022
    Abstract: The present invention relates to compositions comprising at least one fluoroolefin and an effective amount of stabilizer that may be an epoxide, fluorinated epoxide or oxetane, or a mixture thereof with other stabilizers. The stabilized compositions may be useful in cooling apparatus, such as refrigeration, air-conditioning, chillers, and heat pumps, as well as in applications as foam blowing agents, solvents, aerosol propellants, fire extinguishants, and sterilants.
    Type: Application
    Filed: August 31, 2007
    Publication date: October 27, 2011
    Inventors: Andrew Edward Feiring, Viacheslav A. Petrov, Barbara Haviland Minor, Mario Joseph Nappa, Nandini C. Mouli, Thomas J. Leck, Jon Lee Howell
  • Publication number: 20110257444
    Abstract: Disclosed herein are azeotrope and near-azeotrope compositions comprising E-1,1,1,2,3-pentafluoropropene (E-HFC-1225ye) and hydrogen fluoride. The azeotrope and near-azeotrope compositions are useful in processes to produce and in processes to purify E-HFC-1225ye and/or Z-1,1,1,2,3-pentafluoropropene (Z-HFC-1225ye). Also disclosed are processes for the extractive distillation to separate E-HFC-1225ye from Z-HFC-1225ye.
    Type: Application
    Filed: June 28, 2011
    Publication date: October 20, 2011
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: JEFFREY P. KNAPP, Barry Asher Mahler, Velliyur Nott Mallikarjuna Rao
  • Patent number: 8013194
    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: March 11, 2009
    Date of Patent: September 6, 2011
    Assignee: Honeywell International Inc.
    Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
  • Publication number: 20110201840
    Abstract: Disclosed is a process for preparing terminal 1,1-disubstituted alkenes and is to compounds prepared therewith.
    Type: Application
    Filed: February 16, 2010
    Publication date: August 18, 2011
    Applicant: THE CHINESE UNIVERSITY OF HONG KONG
    Inventor: Chun Yu HO
  • Publication number: 20110160498
    Abstract: The subject of the invention is a process for the preparation of 2,3-dichloro-1,1,1-trifluoropropane by chlorination of 3,3,3-trifluoropropene at a pressure greater than 2 bar. Application in the synthesis of 1234yf.
    Type: Application
    Filed: September 11, 2009
    Publication date: June 30, 2011
    Inventors: Anne Pigamo, Michel Devic, Laurent Wendlinger
  • Publication number: 20110160500
    Abstract: The present invention provides a process for producing 2,3,3,3-tetrafluoropropene, comprising distilling a mixture of water and 2,3,3,3-tetrafluoropropene to separate the mixture into a first stream and a second stream, the first stream containing 2,3,3,3-tetrafluoropropene with a water content higher than the original mixture, and the second stream containing 2,3,3,3-tetrafluoropropene with a water content lower than the original mixture; and obtaining 2,3,3,3-tetrafluoropropene with a reduced water content from the second stream. The process of the invention can efficiently remove water from 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Application
    Filed: August 21, 2009
    Publication date: June 30, 2011
    Inventor: Kazuhiro Takahashi
  • Publication number: 20110152586
    Abstract: A method of providing a blend of tetra- and/or pentafluoroalkanes comprising hydrogenating a pentafluoropropene.
    Type: Application
    Filed: January 23, 2009
    Publication date: June 23, 2011
    Inventors: Robert E. Low, Andrew P. Sharratt
  • Publication number: 20110144394
    Abstract: A process for the production of fluorinated alkanes by contacting a feed stream containing a fluorinated olefin and a reducing agent, preferably with a first amount of catalyst to produce a fluorinated alkane, at a first conversion level, wherein a first effluent stream contains unreacted fluorinated olefin and reducing agent; and contacting the first effluent stream under conditions effective to produce a higher level of conversion than said conversion level.
    Type: Application
    Filed: February 25, 2011
    Publication date: June 16, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: PETER H. SCHEIDLE, KEVIN D. ULRICH, MICHAEL VAN DER PUY, GEORGE R. COOK
  • Publication number: 20110118513
    Abstract: The invention provides a process for preparing 1,1,1-trifluoro-2,3-dichloropropane (243db), which process comprises contacting 3,3,3-trifluoropropene (1243zf) with chlorine in the presence of a catalyst, wherein the catalyst comprises activated carbon, alumina and/or an oxide of a transition metal.
    Type: Application
    Filed: April 9, 2009
    Publication date: May 19, 2011
    Applicant: INEOS FLUOR HOLDINGS LIMITED
    Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
  • Publication number: 20110087056
    Abstract: The present invention provides adiabatic plug flow reactors suitable for the production of chlorinated and/or fluorinated propene and higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes. The reactors comprise one or more designs that minimize the production of by-products at a desired conversion.
    Type: Application
    Filed: October 8, 2010
    Publication date: April 14, 2011
    Applicant: DOW GLOBAL TECHNOLOGIES
    Inventors: Max M. Tirtowidjojo, Hua Bai, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt F. Hirsekorn, Manfred Kokott, William J. Kruper, JR., Thomas U. Luebbe, Thomas J. Parsons, Avani Maulik Patel, Marcus Wobser
  • Patent number: 7902410
    Abstract: A process for the production of fluorinated alkanes by contacting a feed stream containing a fluorinated olefin and a reducing agent, preferably with a first amount of catalyst to produce a fluorinated alkane, at a first conversion level, wherein a first effluent stream contains unreacted fluorinated olefin and reducing agent; and contacting the first effluent stream under conditions effective to produce a higher level of conversion than said conversion level.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: March 8, 2011
    Assignee: Honeywell International Inc.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Scheidle, Kevin D. Uhrich
  • Publication number: 20110054226
    Abstract: Disclosed is a process and apparatus for the catalytic hydrogenation of fluoroolefins to fluorocarbons where the reaction is carried out in a multi-tube shell and tube reactor. Reactions involving hydrogenation of fluoro-olefins are typically exothermic. In commercial processes where a fluoro-olefin C(n)H(2n?x)F(x) to C(n)H(2n?x|2)F(x) is hydrogenated (e.g. hexafluoropropylene to 236ea, 1225ye to 245eb, and the like), inadequate management or control of heat removal may induce excess hydrogenation, decomposition and hot spots resulting in reduced yields and potential safety issues. In the hydrogenation of fluoro-olefins, it is therefore necessary to control the reaction temperature as precisely as practical to overcome challenges associated with heat management and safety.
    Type: Application
    Filed: August 31, 2009
    Publication date: March 3, 2011
    Inventors: Haluk Kopkalli, Yuon Chiu, Orlando George Rodrigues, Gus Cerri, Hsueh Sung Tung, Stephen A. Cottrell