Utilizing Unsaturated Compound Patents (Class 570/175)
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Patent number: 11555001Abstract: A process for making 2,3,3,3-tetrafluoropropene (HFO-1234yf) includes providing a composition including 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) to a reactor including a heater surface at a surface temperature greater than about 850° F. (454° C.), and then bringing the composition into contact with the heater surface for a contact time of less than 10 seconds to dehydrochlorinate a portion of the HCFC-244bb to make HFO-1234yf.Type: GrantFiled: June 5, 2019Date of Patent: January 17, 2023Assignee: Honeywell International Inc.Inventors: Haluk Kopkalli, Carlos Navar, Yuon Chiu, Haiyou Wang
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Patent number: 11377406Abstract: The production method according to the present disclosure comprises obtaining a product comprising a fluoroethane from a fluoroethylene by a reaction in the presence of at least one catalyst. The reaction is performed in two or more reaction zones. Each reaction zone comprises a catalyst, and the fluoroethylene is supplied to each reaction zone to perform the reaction.Type: GrantFiled: June 17, 2021Date of Patent: July 5, 2022Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Tomoyuki Iwamoto, Takashi Usui, Takehiro Chaki, Kazuhiro Takahashi, Tsubasa Nakaue
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Patent number: 11052363Abstract: A method for enabling gas exchange and chemical reactions with one or more liquid streams contained in a reactive process vessel are provided. One or more exchange layers within the process vessel can be composed of both collector media and releaser media. The exchange layers allow elements to facilitate increased performance of vessel operations by promoting gas component mixing and diffusion. Improved rates of gas component exchange mean less coking and more gas components available for reaction.Type: GrantFiled: December 21, 2020Date of Patent: July 6, 2021Assignee: Crystaphase Products, Inc.Inventors: John N. Glover, Bradley Glover, Austin Schneider, Peter Gregory Ham
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Patent number: 10364201Abstract: 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: GrantFiled: March 21, 2016Date of Patent: July 30, 2019Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Stephen A. Cottrell, John J. Senetar, Hsueh S. Tung, Daniel C. Merkel, Yuon Chiu, Haluk Kopkalli
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Patent number: 10125066Abstract: 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: GrantFiled: November 29, 2017Date of Patent: November 13, 2018Assignee: Honeywell International Inc.Inventors: Christian Jungong, Daniel C. Merkel
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Patent number: 9856192Abstract: 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, hydrType: GrantFiled: January 12, 2017Date of Patent: January 2, 2018Assignees: 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
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Patent number: 9758455Abstract: 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: GrantFiled: April 1, 2015Date of Patent: September 12, 2017Assignees: DAIKIN INDUSTRIES, LTD., NATIONAL UNIVERSITY CORPORATION HOKKAIDO UNIVERSITYInventors: Masahiro Higashi, Yosuke Kishikawa, Atsushi Shirai, Takashi Namikawa, Sumi Ishihara, Shoji Hara
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Patent number: 9675950Abstract: 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: GrantFiled: January 26, 2015Date of Patent: June 13, 2017Assignee: Honeywell International Inc.Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
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Patent number: 9598336Abstract: 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: GrantFiled: May 16, 2012Date of Patent: March 21, 2017Assignee: E I DU PONT DE NEMOURS AND COMPANYInventors: Patricia Cheung, Allen Capron Sievert, Concetta Lamarca
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Patent number: 9302964Abstract: 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: GrantFiled: June 25, 2015Date of Patent: April 5, 2016Assignee: Asahi Glass Company, LimitedInventors: Shoji Furuta, Tetsuo Otsuka
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Patent number: 9290424Abstract: 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: GrantFiled: March 14, 2013Date of Patent: March 22, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Stephen A. Cottrell, John J. Senetar, Hsueh S. Tung, Daniel C. Merkel, Yuon Chiu, Haluk Kopkalli
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Patent number: 9266800Abstract: 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: GrantFiled: January 31, 2013Date of Patent: February 23, 2016Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventor: Emanuela Antenucci
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Publication number: 20150126785Abstract: 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: ApplicationFiled: July 18, 2012Publication date: May 7, 2015Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.Inventors: Andrew P. Sharratt, Claire Elizabeth Mcguinness, Emma Jane Hodgson
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Patent number: 8969634Abstract: 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: GrantFiled: September 26, 2011Date of Patent: March 3, 2015Assignee: Honeywell International Inc.Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
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Patent number: 8957264Abstract: 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: GrantFiled: December 11, 2013Date of Patent: February 17, 2015Assignee: Asahi Glass Company, LimitedInventors: Shoji Furuta, Yusuke Sugahara, Keiko Nakase, Keisuke Mori
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Patent number: 8952209Abstract: 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: GrantFiled: March 13, 2013Date of Patent: February 10, 2015Assignee: 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
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Patent number: 8946493Abstract: 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: GrantFiled: May 6, 2010Date of Patent: February 3, 2015Assignee: Arkema FranceInventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini
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Patent number: 8921623Abstract: 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: GrantFiled: February 25, 2011Date of Patent: December 30, 2014Assignee: Honeywell Industrial Inc.Inventors: Michael Van Der Puy, George R. Cook, Peter H. Scheidle, Kevin D. Uhrich
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Patent number: 8912370Abstract: 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: GrantFiled: May 5, 2010Date of Patent: December 16, 2014Assignee: Arkema FranceInventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini
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Patent number: 8895788Abstract: 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: GrantFiled: January 21, 2014Date of Patent: November 25, 2014Assignee: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
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Patent number: 8853473Abstract: 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: GrantFiled: August 21, 2009Date of Patent: October 7, 2014Assignee: Daikin Industries, Ltd.Inventor: Kazuhiro Takahashi
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Patent number: 8729321Abstract: 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: GrantFiled: April 19, 2006Date of Patent: May 20, 2014Assignee: Asahi Glass Company, LimitedInventors: Shoji Furuta, Yu{grave over (s)}uke Sugahara, Keiko Nakase, Keisuke Mori
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Publication number: 20140135538Abstract: 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: ApplicationFiled: March 13, 2013Publication date: May 15, 2014Applicant: 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
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Publication number: 20140088328Abstract: 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: ApplicationFiled: May 16, 2012Publication date: March 27, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Patricia Cheung, Allen Capron Sievert, Concetta Lamarca
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Patent number: 8623233Abstract: 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: GrantFiled: January 10, 2011Date of Patent: January 7, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Mark L. Robin, Joan Ellen Bartelt
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Patent number: 8618339Abstract: 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: GrantFiled: April 28, 2008Date of Patent: December 31, 2013Assignee: E I du Pont de Nemours and CompanyInventor: Ekaterina N. Swearingen
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Publication number: 20130225882Abstract: An alpha-alumina support for a hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.Type: ApplicationFiled: April 4, 2013Publication date: August 29, 2013Applicant: HONEYWELL INTERNATIONAL INC.Inventor: HONEYWELL INTERNATIONAL INC.
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Publication number: 20130172577Abstract: 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: ApplicationFiled: February 28, 2013Publication date: July 4, 2013Applicant: BASF SEInventor: BASF SE
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Patent number: 8471078Abstract: A method of providing a blend of tetra- and/or pentafluoroalkanes comprising hydrogenating a pentafluoropropene.Type: GrantFiled: January 23, 2009Date of Patent: June 25, 2013Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Robert E. Low, Andrew P. Sharratt
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Patent number: 8455704Abstract: 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: GrantFiled: November 2, 2011Date of Patent: June 4, 2013Assignee: Honeywell International Inc.Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
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Publication number: 20130102815Abstract: 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 theType: ApplicationFiled: December 12, 2012Publication date: April 25, 2013Applicant: Mexichem Amanco Holding S.A. de C.V.Inventor: Mexichem Amanco Holding S.A. de C.V.
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Patent number: 8426657Abstract: 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: GrantFiled: September 23, 2011Date of Patent: April 23, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Thomas J. Leck, Thomas Frank Saturno, Gregory A. Bell
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Publication number: 20130079563Abstract: 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: ApplicationFiled: September 26, 2011Publication date: March 28, 2013Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
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Patent number: 8404907Abstract: 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: GrantFiled: February 18, 2011Date of Patent: March 26, 2013Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, Andrew Joseph Poss, Rajiv Ratna Singh, Michael Van Der Puy, Ryan J. Hulse
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Publication number: 20130006022Abstract: 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: ApplicationFiled: February 18, 2011Publication date: January 3, 2013Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Yuko Shiotani, Kakeru Hanabusa, Takehiro Chaki, Kazuhiro Takahashi
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Patent number: 8242316Abstract: 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: GrantFiled: August 1, 2011Date of Patent: August 14, 2012Assignee: Honeywell International Inc.Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
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Publication number: 20120178978Abstract: A support of metal oxyfluoride or metal halide for a metal-based hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.Type: ApplicationFiled: March 20, 2012Publication date: July 12, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: HAIYOU WANG, HSUEH S. TUNG
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Publication number: 20120101314Abstract: 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: ApplicationFiled: May 5, 2010Publication date: April 26, 2012Applicant: Arkema FranceInventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini
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Publication number: 20120101315Abstract: 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: ApplicationFiled: May 6, 2010Publication date: April 26, 2012Applicant: Arkema FranceInventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini
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Publication number: 20120065437Abstract: 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: ApplicationFiled: October 25, 2011Publication date: March 15, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Haiyou Wang
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Patent number: 8129574Abstract: 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: GrantFiled: August 31, 2009Date of Patent: March 6, 2012Assignee: Honeywell International Inc.Inventors: Haluk Kopkalli, Yuon Chiu, Orlando George Rodrigues, Gus Cerri, Hsueh Sung Tung, Stephen A. Cottrell
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Publication number: 20110259022Abstract: 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: ApplicationFiled: August 31, 2007Publication date: October 27, 2011Inventors: Andrew Edward Feiring, Viacheslav A. Petrov, Barbara Haviland Minor, Mario Joseph Nappa, Nandini C. Mouli, Thomas J. Leck, Jon Lee Howell
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Publication number: 20110257444Abstract: 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: ApplicationFiled: June 28, 2011Publication date: October 20, 2011Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: JEFFREY P. KNAPP, Barry Asher Mahler, Velliyur Nott Mallikarjuna Rao
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Patent number: 8013194Abstract: 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: GrantFiled: March 11, 2009Date of Patent: September 6, 2011Assignee: Honeywell International Inc.Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
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Publication number: 20110201840Abstract: Disclosed is a process for preparing terminal 1,1-disubstituted alkenes and is to compounds prepared therewith.Type: ApplicationFiled: February 16, 2010Publication date: August 18, 2011Applicant: THE CHINESE UNIVERSITY OF HONG KONGInventor: Chun Yu HO
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Publication number: 20110160500Abstract: 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: ApplicationFiled: August 21, 2009Publication date: June 30, 2011Inventor: Kazuhiro Takahashi
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Publication number: 20110160498Abstract: 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: ApplicationFiled: September 11, 2009Publication date: June 30, 2011Inventors: Anne Pigamo, Michel Devic, Laurent Wendlinger
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Publication number: 20110152586Abstract: A method of providing a blend of tetra- and/or pentafluoroalkanes comprising hydrogenating a pentafluoropropene.Type: ApplicationFiled: January 23, 2009Publication date: June 23, 2011Inventors: Robert E. Low, Andrew P. Sharratt
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Publication number: 20110144394Abstract: 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: ApplicationFiled: February 25, 2011Publication date: June 16, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: PETER H. SCHEIDLE, KEVIN D. ULRICH, MICHAEL VAN DER PUY, GEORGE R. COOK
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Publication number: 20110118513Abstract: 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: ApplicationFiled: April 9, 2009Publication date: May 19, 2011Applicant: INEOS FLUOR HOLDINGS LIMITEDInventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt