Patents Represented by Attorney Bruce O. Bradford
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Patent number: 8337595Abstract: Disclosed is a process for removing impurities from a product stream comprising trans HFO-1234ze and an HFO-1234 impurity that uses one or more adsorbents that are selective for the HFO-1234 impurity, such that the HFO-1234 impurity is removed from the product stream. One such impurity is HFO-1234zc, which is removed from its mixture with trans HFO-1234ze by action of an adsorbent having pores in the range of from about 5 angstroms to about 10 angstroms.Type: GrantFiled: April 20, 2011Date of Patent: December 25, 2012Assignee: Honeywell International Inc.Inventors: Raymond Hilton Thomas, Stephen A. Cottrell
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Patent number: 8324436Abstract: A multi-step process for preparing 2,3,3,3-tetrafluoro-1-propene comprising the steps of (a) contacting a starting material comprising 2-chloro-3,3,3-trifluoro-1-propene with hydrogen fluoride in the presence of activated first catalyst selected from the group consisting of antimony-halides, iron-halides, titanium halides, and tin-halides, to produce an intermediate composition; and (b) contacting said intermediate composition with a second catalyst of activated carbon to produce a final product comprising 2,3,3,3-tetrafluoro-1-propene.Type: GrantFiled: November 5, 2008Date of Patent: December 4, 2012Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Barbara A. Light, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
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Patent number: 8293954Abstract: This invention achieves a catalyst life improvement for the catalyzed vapor phase reaction of 1,1,1,3,3-pentachloropropane with hydrogen fluoride to form 1-chloro-3,3,3-trifluoropropene by introducing an oxygen co-feed into the fluorination reactor. By introduction of an oxygen co-feed to the reactor feed, the catalyst life was extended a minimum of two-fold (2×).Type: GrantFiled: March 10, 2010Date of Patent: October 23, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
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Patent number: 8288598Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.Type: GrantFiled: January 13, 2010Date of Patent: October 16, 2012Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Konstantin A. Pokrovski, Hsueh S. Tung, Michael Van Der Puy
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Patent number: 8268063Abstract: A method and composition for transforming a latent physiological biometric into a visible physiological biometric are provided, the method comprising: providing a latent biometric disposed on a surface of an article, wherein said biometric comprises at least one eccrine-derived compound; contacting said latent biometric with a developing solution, wherein said developing solution comprises at least one imaging reagent selected from ninhydrin and 1,8-diazafluoren-9-one and a carrier solvent comprising at least one C3-C4 hydrofluorocarbon; and reacting said imaging reagent with said eccrine-derived compound to produce a visible physiological biometric.Type: GrantFiled: April 11, 2009Date of Patent: September 18, 2012Assignee: Honeywell International Inc.Inventors: David Nalewajek, Cheryl L. Cantlon, Andrew J. Poss, Rajiv Ratna Singh, Ian Shankland
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Patent number: 8263818Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.Type: GrantFiled: January 13, 2010Date of Patent: September 11, 2012Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Konstantin A. Pokrovski, Hsueh S. Tung, Michael Van Der Puy
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Patent number: 8258355Abstract: Provided is a continuous process for preparing 1,1,2,3-tetrachloro-1-propene having the steps of catalytically dehydrochlorinating CH2ClCCl2CH2Cl in the gas phase to produce CHCl?CClCH2Cl; chlorinating the CHCl?CClCH2Cl to form CHCl2CCl2CH2Cl; and catalytically dehydrochlorinating the CHCl2CCl2CH2Cl in the gas phase to form CCl2?CClCH2Cl.Type: GrantFiled: July 24, 2008Date of Patent: September 4, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh S. Tung, Michael Van Der Puy, Jing Ji Ma
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Patent number: 8252965Abstract: 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: GrantFiled: August 12, 2009Date of Patent: August 28, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
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Patent number: 8247366Abstract: An azeotrope-like composition consisting essentially of 1,1,2,3-tetrachloropropene and hydrogen fluoride is provided, as well as methods that involve such an azeotrope-like composition.Type: GrantFiled: August 4, 2011Date of Patent: August 21, 2012Assignee: Honeywell International Inc.Inventors: Hsueh S. Tung, Hang T. Pham, Rajiv R. Singh, Daniel C. Merkel, Robert Johnson
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Patent number: 8247624Abstract: Dehydrohalogenation processes for the preparation of fluoropropenes from corresponding halopropanes, in which the fluoropropenes have the formula CF3CY?CXNHP, wherein X and Y are independently hydrogen or a halogen selected from fluorine, chlorine, bromine and iodine; and N and P are independently integers equal to 0, 1 or 2, provided that (N+P)=2.Type: GrantFiled: September 6, 2011Date of Patent: August 21, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh S. Tung
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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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Patent number: 8153018Abstract: Disclosed are compositions and systems having utility in numerous situations, including in particular solvent cleaning systems, as well as refrigerant lubricants and/or compatibilizing agents, and to methods which utilize such compositions and systems. More particularly, the present invention in preferred aspects is directed to solvents, blowing agents, heat transfer fluids and compatibilizing agents comprising the compound 3-chloro-1,1,1,6,6,6-hexafluoro-2,4-hexadiene. In particular, this invention provides a method for the production of the compound of Formula I, 3-chloro-1,1,1,6,6,6- hexafluoro-2,4-hexadiene,comprising reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in the presence of a catalyst, in a reactor.Type: GrantFiled: September 30, 2011Date of Patent: April 10, 2012Assignee: Honeywell International Inc.Inventors: Robert C. Johnson, Hsueh Sung Tung
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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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Patent number: 8067650Abstract: This invention relates a process for the manufacture of the HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze). More particularly, the invention pertains to a process for the manufacture of the HFO trans-1234ze by first dehydrofluorinating 1,1,1,3,3-pentafluoropropane to thereby produce a mixture of cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and hydrogen fluoride. Then optionally recovering hydrogen fluoride and then recovering trans-1,3,3,3-tetrafluoropropene.Type: GrantFiled: July 10, 2007Date of Patent: November 29, 2011Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 8066901Abstract: Provided are azeotropic and azeotrope-like compositions of trans-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz(E)) and water. Such azeotropic and azeotrope-like compositions are useful in isolating HFO-1336mzz(E) from impurities during production. Azeotropes of the instant invention are similarly useful in final compositions, such as blowing agent, propellants, refrigerants, diluents for gaseous sterilization and the like.Type: GrantFiled: January 19, 2011Date of Patent: November 29, 2011Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Hang T. Pham, Rajiv Ratna Singh
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Patent number: 8044015Abstract: Disclosed are compositions and systems having utility in numerous situations, including in particular solvent cleaning systems, as well as refrigerant lubricants and/or compatibilizing agents, and to methods which utilize such compositions and systems. More particularly, the present invention in preferred aspects is directed to solvents, blowing agents, heat transfer fluids and compatibilizing agents comprising the compound 3-chloro-1,1,1,6,6,6-hexafluoro-2,4-hexadiene.Type: GrantFiled: March 12, 2010Date of Patent: October 25, 2011Assignee: Honeywell International Inc.Inventors: Robert C. Johnson, Hsueh Sung Tung
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Patent number: 8034985Abstract: A process for the preparation of a fluoroiodoalkane compound represented by the formula: CF3(CF2)n—Y, wherein n is 0 or 1. The process includes contacting A, B and C. A is represented by the formula: CF3(CF2)n—Y, wherein n is 0 or 1, and Y is selected from the group consisting of: H, Cl, Br, and COOH. B is a source of iodine, and C is a catalyst containing elements with d1s1 configuration and lanthanide elements. The process occurs at a temperature, and for a contact time, sufficient to produce the fluoroiodoalkane compound.Type: GrantFiled: February 15, 2007Date of Patent: October 11, 2011Assignee: Honeywell International, Ltd.Inventors: Shuwu Yang, HsuehSung Tung
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Patent number: 8034308Abstract: A multi-stage, multi-tube, shell-and-tube reactor which contains reaction zones and interstage temperature control (cooling/heating) zones in series. The reactor has at least two types of zones which both contribute to removing or supplying heat to the system depending on the system's need. The reactor will have a group of reaction zones which contain tubes packed with catalyst to progress the reaction and remove or supply heat simultaneously. There are also a number of interstage temperature control (cooling/heating) zones which are designed to supply or remove heat to or from the system. The positioning, number, and design of the zones will depend on the amount of temperature control desired and exothermic or endothermic nature of the processes to be conducted in the reactor.Type: GrantFiled: June 9, 2009Date of Patent: October 11, 2011Assignee: Honeywell International, Inc.Inventors: Yuon Chiu, Stephen A. Cottrell, Richard Durick Horwath, Haluk Kopkalli
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Patent number: 7994371Abstract: Disclosed is a process for the making chlorotrifluoroethylene. The process comprises the step of reacting 1,1,2-trichlorotrifluoroethane with a reducing metal in the presence of a polar aprotic solvent under conditions sufficient to form chlorotrifluoroethylene.Type: GrantFiled: May 14, 2010Date of Patent: August 9, 2011Assignee: Honeywell International, Inc.Inventors: Selma Bektesevic, Michael John Murphy
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Patent number: 7880040Abstract: Disclosed is a method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CFnCHmXa-m??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where each X is independently Cl, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a-m?0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a C1 addition agent under conditions effective to produce a compound of formula (I).Type: GrantFiled: November 3, 2006Date of Patent: February 1, 2011Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy, Rajiv R. Singh, Haiyou Wang, Robert C. Johnson, Rajesh K. Dubey