Purification Or Recovery Patents (Class 570/177)
  • Patent number: 10633312
    Abstract: The invention concerns a method for purifying and drying a hydrofluoroolefin stream comprising a hydrofluoroolefin, water and impurities composed of halogenated carbon compounds, characterised in that said stream is brought into contact with an adsorbent and in that the purification and the drying processes are carried out simultaneously in one and the same step, said hydrofluoroolefin being a compound of formula (I): CX1X2?CX3CX4X5X6 in which each Xi (i ranging from 1 to 6) represents, independently of one another, a hydrogen atom or a chlorine or fluorine atom, it being understood that at least one of the Xi's represents a fluorine atom.
    Type: Grant
    Filed: September 19, 2016
    Date of Patent: April 28, 2020
    Assignee: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 10487031
    Abstract: The present application discloses compositions comprising hydrogen fluoride and fluorinated compounds (e.g., hydrofluorocarbons), wherein the fluorinated compound is present in the composition in an amount effective to form an azeotrope composition or azeotrope-like composition with the hydrogen fluoride.
    Type: Grant
    Filed: September 10, 2018
    Date of Patent: November 26, 2019
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Sheng Peng, Jeffrey Knapp
  • Patent number: 9410064
    Abstract: The present invention relates to fluoroolefin compositions. The fluoroolefin compositions of the present invention are useful as refrigerants or heat transfer fluids and in processes for producing cooling or heat. Additionally, the fluoroolefin compositions of the present invention may be used to replace currently used refrigerant or heat transfer fluid compositions that have higher global warming potential.
    Type: Grant
    Filed: January 23, 2015
    Date of Patent: August 9, 2016
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Mario Joseph Nappa, Barbara Haviland Minor, Allen Capron Sievert
  • Patent number: 9266799
    Abstract: The present invention relates to a method for separating a composition containing 2,3,3,3-tetrafluoropropene and hydrofluoric acid, and for recovering the thus-separated 2,3,3,3-tetrafluoropropene and hydrofluoric acid. The invention also relates to a method for manufacturing and purifying 2,3,3,3-tetrafluoropropene using a hydrofluorination reaction of the saturated or unsaturated compound having three carbon atoms and including at least one chlorine atom in the presence of a fluorination catalyst.
    Type: Grant
    Filed: June 14, 2012
    Date of Patent: February 23, 2016
    Assignee: Arkema France
    Inventors: Dominique Deur-Bert, Bertrand Collier
  • Patent number: 9260365
    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: Grant
    Filed: March 10, 2015
    Date of Patent: February 16, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Haiyou Wang
  • Patent number: 9156752
    Abstract: The present invention discloses high purity E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and methods to produce the same. More specifically, the present invention discloses the methods of making 1233zd(E) essentially free of toxic impurities (e.g. 2-chloro-3,3,3-trifluoropropene (1233xf), chlorotetrafluoro-propene (1224), and 3,3,3-trifluoropropyne). The present invention further provides methods for making high purity 1233zd(E) with concentration of 1233xf and 1224 at or below 200 parts per million (ppm) and 3,3,3-trifluoropropyne impurities at or below 20 ppm. Formation of 1233xf impurity can be avoided if pure 1,1,1,3,3-pentachloropropane is used as a starting material. It was also found that formation of 1233xf is avoided if a liquid phase manufacturing process is used.
    Type: Grant
    Filed: January 4, 2011
    Date of Patent: October 13, 2015
    Assignee: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Rajiv Ratna Singh, Ian Shankland, Hsueh Sung Tung
  • Patent number: 9018430
    Abstract: The present invention provides a method for separating halocarbons. In particular, the invention provides a method for separating halogenated olefin impurities from 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) using a solid adsorbent, particularly activated carbon. More particularly the invention pertains to a method for separating 2-chloro-3,3,3-trifluoro-propene (HCFO-1233xf) from HCFC-244bb, which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: June 19, 2014
    Date of Patent: April 28, 2015
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Patent number: 9018428
    Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 28, 2015
    Assignee: Honeywell International Inc.
    Inventor: Stephen A. Cottrell
  • Patent number: 9012703
    Abstract: The invention relates to a process for removing one or more undesired (hydro)halocarbon compounds from a (hydro)fluoroalkene, the process comprising contacting a composition comprising the (hydro)fluoroalkene and one or more undesired (hydro)halocarbon compounds with an aluminum-containing absorbent, activated carbon, or a mixture thereof.
    Type: Grant
    Filed: October 8, 2010
    Date of Patent: April 21, 2015
    Assignee: Mexichem Amanco Holdings S.A. de C.V.
    Inventors: Andrew P Sharratt, Claire E McGuiness, John Hayes
  • Patent number: 9000240
    Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.
    Type: Grant
    Filed: May 15, 2012
    Date of Patent: April 7, 2015
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 8987536
    Abstract: The present disclosure relates to processes for reducing the concentration of RfC?CX impurities in fluoroolefins. The process involves: contacting a mixture comprising at least one fluoroolefin and at least one RfC?CX impurity with at least one amine to reduce the concentration of the at least one RfC?CX impurity in the mixture; wherein Rf is a perfluorinated alkyl group, and X is H, F, Cl, Br or I. The present disclosure also relates to processes for making at least one hydrotetrafluoropropene product selected from the group consisting of CF3CF?CH2, CF3CH?CHF, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process. The present disclosure also relates to processes for making at least one hydrochlorotrifluoropropene product selected from the group consisting of CF3CCl?CH2, CF3CH?CHCl, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process.
    Type: Grant
    Filed: June 6, 2013
    Date of Patent: March 24, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Patent number: 8975456
    Abstract: The present invention provides a method for purifying HFO-1234yf, comprising the steps of (1) cooling a liquid mixture containing HFO-1234yf and HF to separate the mixture into a upper liquid phase having a high concentration of HF and a lower liquid phase having a high concentration of 2,3,3,3-tetrafluoropropene; and (2) subjecting the lower liquid phase obtained in step (1) to a distillation operation to withdraw a mixture containing HFO-1234yf and HF from a top of a distillation column, thereby obtaining substantially HF-free HFO-1234yf from a bottom of the distillation column. According to the present invention, HF and HFO-1234yf contained in a mixture containing HF and HFO-1234yf can be separated under simple and economically advantageous conditions.
    Type: Grant
    Filed: November 9, 2010
    Date of Patent: March 10, 2015
    Assignee: Daikin Industries, Ltd.
    Inventors: Takehiro Chaki, Kazuhiro Takahashi, Yoshinori Tanaka, Hitoshi Yoshimi
  • Patent number: 8975454
    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: Grant
    Filed: October 25, 2011
    Date of Patent: March 10, 2015
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Haiyou Wang
  • Publication number: 20150038749
    Abstract: Disclosed is a process for producing 2-chloro-1,3,3,3-tetrafluoropropene (1224), including a first step of separating 2,3-dichloro-1,1,1,3-tetrafluoropropane 234da) into erythro form and threo form, and a second step of bringing the separated erythro form or threo form in contact with a base to obtain 2-chloro-1,3,3,3-tetrafluoropropene (1224). The first step is a step of separating 234da by distillation to achieve a separation into a fraction containing mainly erythro form and a fraction containing mainly threo form. In the second step, 1224 cis form is obtained from the erythro form, and 1224 trans form is obtained from the threo form. By this process, it is possible to selectively and efficiently produce cis form or trans form of 2-chloro-1,3,3,3-tetrafluoropropene (1224).
    Type: Application
    Filed: May 8, 2014
    Publication date: February 5, 2015
    Applicant: Central Glass Company, Limited
    Inventors: Hideaki IMURA, Yoshio NISHIGUCHI, Masamune OKAMOTO, Tatsuya HAYASAKA, Minako OOMURA, Satoru OKAMOTO, Naoto TAKADA
  • Publication number: 20150018587
    Abstract: Useful processes for isolating the fluorinated products formed by reaction with 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead) are disclosed. The processes comprise the conversion of the byproduct (formula I) to sulfinate ester (formula V), and to sulfonate eater (formula VI), and then to the water-soluble sulfonate salt (formula IV) in the presence of the fluorinated products.
    Type: Application
    Filed: February 7, 2013
    Publication date: January 15, 2015
    Applicant: UBE Industries, Ltd.
    Inventors: Norimichi Saito, Junichi Chika, Teruo Umemoto
  • Patent number: 8921621
    Abstract: A process for the manufacture of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) at commercial scale from the reaction of HCC-240 and HF is disclosed. In one embodiment, HCC-240fa and HF are fed to a reactor operating at high pressure. Several different reactor designs useful in this process include; a stirred-tank reactor (batch and/or continuous flow); a plug flow reactor; a static mixer used as a reactor; at least one of the above reactors operating at high pressure; optionally combined with a distillation column running at a lower pressure; and combinations of the above; and/or with a distillation column. The resulting product stream consisting of 1233zd, HCl, HF, and other byproducts is partially condensed to recover HF by phase separation. The recovered HF phase is recycled to the reactor. The HCl is scrubbed from the vapor stream and recovered as an aqueous solution.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: December 30, 2014
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Daniel C. Merkel
  • Publication number: 20140309462
    Abstract: The present disclosure provides a fluorination process which involves reacting a hydrohaloalkene of the formula RfC—Cl?CH2 with HF in a reaction zone in the presence of a fluorination catalyst selected from the group consisting of TaF5 and TiF4 to produce a product mixture containing a hydrohaloalkane of the formula RfCFClCH3, wherein Rf is a perfluorinated alkyl group.
    Type: Application
    Filed: November 9, 2012
    Publication date: October 16, 2014
    Inventors: Mario Joseph NAPPA, Andrew JACKSON, Daniel C. MERKEL
  • 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: 8853472
    Abstract: A process is disclosed for reducing the amount of monofluoroacetate. The process involves (a) contacting a hydrofluorocarbon with a reactant basic aqueous solution to produce an organic phase solution containing a hydrofluoroolefin and an aqueous phase solution containing a monofluoroacetate; and (b) heating the aqueous phase solution to an effective temperature to reduce the amount of monofluoroacetate in the aqueous phase solution, wherein fluoride concentration in the aqueous phase solution is substantially high. Another process is disclosed for reducing the amount of monofluoroacetate.
    Type: Grant
    Filed: May 7, 2010
    Date of Patent: October 7, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Patricia Cheung, Karl R. Krause, Michael A. Sisk
  • Publication number: 20140296585
    Abstract: The present invention relates to a method for separating a composition containing 2,3,3,3-tetrafluoropropene and hydrofluoric acid, and for recovering the thus-separated 2,3,3,3-tetrafluoropropene and hydrofluoric acid. The invention also relates to a method for manufacturing and purifying 2,3,3,3-tetrafluoropropene using a hydrofluorination reaction of the saturated or unsaturated compound having three carbon atoms and including at least one chlorine atom in the presence of a fluorination catalyst.
    Type: Application
    Filed: June 14, 2012
    Publication date: October 2, 2014
    Inventors: Dominique Deur-Bert, Bertrand Collier
  • Patent number: 8845921
    Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) by adding a third component and then separating via conventional distillation. More particularly the invention pertains to a method for separating HCFC-244bb from HCFC-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: September 30, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Hang T. Pham, Rajiv R. Singh
  • Patent number: 8846990
    Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.
    Type: Grant
    Filed: October 10, 2012
    Date of Patent: September 30, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20140284517
    Abstract: Provided are azeotropic and azeotrope-like compositions of trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)) and water. Such azeotropic and azeotrope-like compositions are useful in isolating trans-1,3,3,3-tetrafluoropropene from impurities during production. Azeotropes of the instant invention are similarly useful in final compositions or for the manufacture of final compositions, such as blowing agent, propellants, refrigerants, diluents for gaseous sterilization and the like.
    Type: Application
    Filed: June 9, 2014
    Publication date: September 25, 2014
    Inventors: RYAN HULSE, HALUK KOPKALLI, HANG T. PHAM
  • Publication number: 20140275655
    Abstract: The present process relates to a process comprising: contacting a mixture comprising 2,3,3,3-tetrafluoropropene and at least one halogenated ethylene impurity with at least one adsorbent or at least one chemisorption catalyst to reduce the concentration of said at least one halogenated ethylene impurity.
    Type: Application
    Filed: March 12, 2014
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou WANG, Hsueh Sung TUNG
  • Publication number: 20140219901
    Abstract: Methods for releasing associated guest materials from a metal organic framework are provided. Methods for associating guest materials with a metal organic framework are also provided. Methods are provided for selectively associating or dissociating guest materials with a metal organic framework. Systems for associating or dissociating guest materials within a series of metal organic frameworks are provided. Thermal energy transfer assemblies are provided. Methods for transferring thermal energy are also provided.
    Type: Application
    Filed: April 4, 2014
    Publication date: August 7, 2014
    Applicant: Battelle Memorial Institute
    Inventors: B. Peter McGrail, Daryl R. Brown, Praveen K. Thallapally
  • Patent number: 8796493
    Abstract: The present invention provides a method for separating halocarbons. In particular, the invention provides a method for separating halogenated olefin impurities from 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) using a solid adsorbent, particularly activated carbon. More particularly the invention pertains to a method for separating 2-chloro-3,3,3-trifluoro-propene (HCFO-1233xf) from HCFC-244bb, which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: September 30, 2011
    Date of Patent: August 5, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Patent number: 8779220
    Abstract: A method for capturing certain fluorinated vinyl monomers from a gaseous mixture using ionic liquids is described. The gaseous mixture is contacted with at least one ionic liquid, whereby at least a portion of the fluorinated vinyl monomer is absorbed by the ionic liquid. The method is useful for reducing emissions of fluorinated vinyl monomers and for increasing the product yields in the manufacture of polymers from these monomers.
    Type: Grant
    Filed: May 9, 2012
    Date of Patent: July 15, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Charles Joseph Noelke, Mark Brandon Shiflett
  • Patent number: 8716538
    Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.
    Type: Grant
    Filed: August 2, 2013
    Date of Patent: May 6, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung
  • Patent number: 8628644
    Abstract: The present invention relates to a process for separating close-boiling and azeotropic components of mixtures, wherein said mixtures contain at least one hydrofluorocarbon compound, using at least one ionic liquid.
    Type: Grant
    Filed: September 22, 2006
    Date of Patent: January 14, 2014
    Assignee: E I du Pont Nemours and Company
    Inventors: Mark B. Shiflett, Akimichi Yokozeki
  • 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: 8541634
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: January 14, 2013
    Date of Patent: September 24, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T Pham
  • Publication number: 20130231448
    Abstract: A process for separating tetrafluoroethylene from a mixture comprising tetrafluoroethylene and carbon dioxide by contacting the mixture with at least one ionic liquid.
    Type: Application
    Filed: November 19, 2012
    Publication date: September 5, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Mark Brandon SHIFLETT, Akimichi YOKOZEKI
  • Patent number: 8524956
    Abstract: Disclosed is a method of purifying (Z)-1-chloro-3,3,3-trifluoropropene of the formula [1], comprising: distilling a mixture containing (Z)-1-chloro-3,3,3-trifluoropropene and 1-chloro-1,3,3,3-tetrafluoropropane (CF3CH2CHClF), wherein the distilling is performed by extractive distillation of the mixture in the coexistence of at least one kind of compound selected from the group consisting of halogenated hydrocarbons of the formula [2], halogenated unsaturated hydrocarbons, nitriles, ketones, carbonates, ethers, esters and alcohols as an extractant [Chem. 8] CFnCl3-nCHXCClFmH2-m??[2] where X represents a hydrogen atom (H), a fluorine atom (F) or a chlorine atom (Cl); n represents an integer of 0 to 3; and m represents an integer of 0 to 2.
    Type: Grant
    Filed: January 25, 2010
    Date of Patent: September 3, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Akira Ishihara, Yasuo Hibino, Ryoichi Tamai
  • Publication number: 20130221273
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,1,3,3-tetrachloro-1-fluoropropane (HCFC-241fa) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of HFC-245fa and HCFO-1233zd.
    Type: Application
    Filed: February 23, 2012
    Publication date: August 29, 2013
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hang T. Pham, Hsueh Sung Tung, Ryan Hulse
  • Patent number: 8519201
    Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.
    Type: Grant
    Filed: March 19, 2012
    Date of Patent: August 27, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung
  • Publication number: 20130217929
    Abstract: The present invention relates to an azeotropic or azeotrope-like mixture consisting essentially of 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and hydrogen fluoride.
    Type: Application
    Filed: April 11, 2013
    Publication date: August 22, 2013
    Applicant: Honeywell International Inc.
    Inventor: Honeywell International Inc.
  • Patent number: 8497401
    Abstract: The invention is directed to a ternary azeotrope-like mixture consisting essentially of effective amounts of 1,1,1,3,3-pentafluoropropane, 1-chloro-3,3,3-trifluoropropene, and hydrogen fluoride.
    Type: Grant
    Filed: November 7, 2011
    Date of Patent: July 30, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Rajiv Ratna Singh, Hsueh Sung Tung, Ian Shankland
  • Patent number: 8481793
    Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: July 26, 2012
    Date of Patent: July 9, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung, Konstantin A. Pokrovski
  • Publication number: 20130158305
    Abstract: The present invention provides a method for removing moisture from fluorine-containing compounds, the method comprising bringing a fluorine-containing compound contaminated with moisture into contact with an aqueous solution containing a metal salt. The method of the present invention can continuously and efficiently remove moisture from various fluorine-containing compounds, such as hydrofluoroolefins. In addition, the method produces less waste, etc., and is an industrially advantageous moisture removal method.
    Type: Application
    Filed: September 6, 2011
    Publication date: June 20, 2013
    Applicant: DAIKIN INDUSTRIES LTD.
    Inventor: Kazuhiro Takahashi
  • Publication number: 20130131404
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Application
    Filed: January 14, 2013
    Publication date: May 23, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: Honeywell International Inc.
  • Patent number: 8426658
    Abstract: Provided are azeotropic and azeotrope-like compositions of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and hydrogen fluoride (HF). Such azeotropic and azeotrope-like compositions are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: October 28, 2011
    Date of Patent: April 23, 2013
    Assignee: Honeywell International Inc.
    Inventors: Hang T. Pham, Rajiv R. Singh, Hsueh Sung Tung, Konstantin A. Pokrovski, Daniel C. Merkel
  • Patent number: 8404906
    Abstract: The present invention provides a process for producing 1,2,3,4-tetrachlorohexafluorobutane having a high purity at a low cost industrially and efficiently. The process for producing 1,2,3,4-tetrachlorohexafluorobutane according to the present invention comprises a step of allowing 1,2,3,4-tetrachlorobutane to react with a fluorine gas to prepare a reaction product containing 1,2,3,4-tetrachlorohexafluorobutane and hydrogen-containing compounds as an impurity, and a step of introducing the reaction product into single or plural distillation columns and distilling to separate the hydrogen-containing compounds from the reaction product and thereby preparing purified 1,2,3,4-tetrachlorohexafluorobutane wherein the at least one of distillation columns has a theoretical plate number of 15 or more.
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: March 26, 2013
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi, Takami Ohe
  • Publication number: 20130006023
    Abstract: A method and apparatus for removing fluorinated hydrocarbons and/or perchlorate species from groundwater which can utilize ion exchange media comprising a hydrophobic polymeric matrix. Fluorinated hydrocarbons can be reduced to a parts per trillion level and perchlorate to a low parts per billion level, rendering the groundwater suitable for consumption as drinking water under regulatory standards.
    Type: Application
    Filed: November 21, 2007
    Publication date: January 3, 2013
    Inventors: Gregory Bachman, Timothy J. Peschman, Douglas C. Kellogg, Jeffrey J. Ogle
  • Patent number: 8344192
    Abstract: The invention provides a technique enabling the separation and recovery of an unreacted fluoromonomer from an aqueous fluoropolymer dispersion obtained by emulsion polymerization, without using any extraction solvent, and enabling the prevention of a hydrolysis of —SO2F and a like sulfonic acid precursor functional group convertible to sulfonic acid group. Thus, the invention provides a recovering method fluoromonomer having a sulfonic acid precursor functional group convertible to a sulfonic acid group and remaining unreacted from an aqueous fluoropolymer dispersion obtained by emulsion polymerization of the fluoromonomer, wherein the unreacted fluoromonomer is recovered from the aqueous fluoropolymer dispersion by evaporation, wherein the aqueous fluoropolymer dispersion has an acidic pH.
    Type: Grant
    Filed: December 7, 2007
    Date of Patent: January 1, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Tadaharu Isaka, Tadashi Ino, Masaharu Nakazawa, Masahiro Kondo
  • Patent number: 8299280
    Abstract: A process for recovering hexafluoropropylene and hexafluoropropylene oxide from a liquid mixture of these components is provided. The process includes, in a stripping stage, contacting the mixture with a gaseous stripping agent, thereby to strip hexafluoropropylene from the mixture. A gaseous product comprising hexafluoropropylene and gaseous stripping agent is withdrawn from the stripping stage, as is a liquid product comprising hexafluoropropylene oxide.
    Type: Grant
    Filed: October 27, 2009
    Date of Patent: October 30, 2012
    Assignee: University of Kwazulu-Natal
    Inventors: Deresh Ramjugernath, Paramespri Naidoo, Clinton Shalendra Subramoney, Michael Wayne Nelson
  • Patent number: 8269052
    Abstract: The invention relates to a method for producing pentafluoroethane, and especially to a method comprising (i) a step during which perchloroethylene and optionally 2,2-dichloro-1,1,1-trifluoroethane and/or 2-chloro-1,1,1,2-tetrafluoroethane react(s) with hydrofluoric acid in a gaseous phase in the presence of a catalyst in an adiabatic multi-stage reactor, and optionally (ii) a step of separating the flow produced in step (i) in order to obtain a fraction of light products and a fraction of heavy products.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: September 18, 2012
    Assignee: Arkema France
    Inventors: Bertrand Collier, Géraldine Cavallini, Béatrice Boussand
  • Patent number: 8252965
    Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: August 12, 2009
    Date of Patent: August 28, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 8252964
    Abstract: The subject of the invention is a process for the purification of 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf). More particularly, it relates to a purification process in which 2,3,3,3-tetrafluoro-1-propene, comprising impurities based on halogen compounds, is brought into contact with an adsorbent, preferably molecular sieves and advantageously molecular sieves having a pore opening with an average diameter between 5 and 11 ?, preferably between 5 and 9 ?.
    Type: Grant
    Filed: June 8, 2009
    Date of Patent: August 28, 2012
    Assignee: Arkema France
    Inventors: Michel Devic, Anne Pigamo, Laurent Wendlinger
  • Patent number: 8232436
    Abstract: Provided is a process for purifying a fluorine compound capable of yielding a highly pure fluorine compound by removing at least oxygen from a fluorine compound containing an oxygen compound as an impurity. In a process according to the present invention for purifying a fluorine compound, the following is brought into contact with the fluorine compound, which contains an oxygen compound as an impurity, thereby removing at least oxygen: carbonyl fluoride in an amount of a 0.1-fold equivalent or more and a 100-fold equivalent or less of oxygen atoms in the fluorine compound.
    Type: Grant
    Filed: August 29, 2008
    Date of Patent: July 31, 2012
    Assignee: Stella Chemifa Corporation
    Inventors: Masahide Waki, Daisuke Sakai, Toshihisa Sakurai
  • Patent number: 8212092
    Abstract: The present invention relates to processes for reducing the concentration of acidic impurities HF, HCl, HBr, HI, HNO3 and H2SO4 in fluorinated hydrocarbons. The process involves: (i) contacting the fluorinated hydrocarbon with a phosphorous oxyacid salt, and (ii) recovering the fluorinated hydrocarbon having reduced concentration of, or substantially free of, said acidic contaminant, provided that said fluorinated hydrocarbon is not CF3CH2CF3 or CF3CHFCF3.
    Type: Grant
    Filed: June 23, 2008
    Date of Patent: July 3, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen C Sievert