Halogenated Hydrocarbon Component Patents (Class 510/412)
  • Patent number: 10738001
    Abstract: A hydrofluoroolefin is represented by the following general formula (A): in which, Rf1 and Rf2 are (i) independently linear or branched fluoroalkyl groups having with 1-8 carbon atoms and optionally include one or more catenated heteroatoms; or (ii) bonded together to form a ring structure having 4-8 carbon atoms and optionally include one or more catenated heteroatoms; ? is CF3, F, H; ? is F or H; ? is CF3, F, CF2H, CFH2, or CH3, and the compound includes a total of 1-4 H atoms; and with the provisos that at least one of ? and ? is F or H; when ? is CF3 or F, at least one of ? and ? is H; when ? is CH3, at least one of ? and ? is F, and when ? is CF3, then ? is H and ? is F; wherein at least one of Rf1 and Rf2 have two or more carbon atoms.
    Type: Grant
    Filed: May 27, 2016
    Date of Patent: August 11, 2020
    Assignee: 3M Innovative Properties Company
    Inventors: William M. Lamanna, Michael J. Bulinski, Michael G. Costello, Kiah A. Smith, Sean M. Smtih
  • Patent number: 10329388
    Abstract: A solvent composition and method for making same is disclosed having a composition between 26 to 90 weight percent propionate, butyrate, or combination thereof and between 10 to 74 weight percent fluorinated solvent blend, wherein the fluorinated solvent blend includes t-DCE. A polymer solvent system is also disclosed incorporating the solvent composition and dissolved polymers, such as SEBS polymers. The solvent composition and polymer solvent system is minimally combustible or preferably nonflammable.
    Type: Grant
    Filed: August 16, 2016
    Date of Patent: June 25, 2019
    Assignee: ZYP Coatings, Inc.
    Inventor: Cressie E Holcombe
  • Patent number: 9587207
    Abstract: A solvent composition and system is disclosed having a composition including n-propyl bromide and a propionate containing liquid and/or a butyrate containing liquid. The solvent system may include approximately 35 to 92.5 weight percent propionate containing liquid and approximately 7.5 to 65 weight percent n-propyl bromide. Alternatively, the solvent system may include approximately 40 to 85 weight percent butyrate containing liquid and 15 to 60 weight percent, n-propyl bromide. The solvent system may incorporate a polymer, such as a synthetic rubber polymer. Further the solvent system preferably has high solvency while maintaining desirable evaporation rates and is preferably nonflammable, combustible, or minimally a class IC flammable liquid.
    Type: Grant
    Filed: January 6, 2016
    Date of Patent: March 7, 2017
    Assignee: ZYP COATINGS, INC.
    Inventor: Cressie E Holcombe, Jr.
  • Patent number: 9296981
    Abstract: Methods of cleaning a medical device are provided via exposing the medical device to a compressed CO2-based mixture. The compressed CO2-based mixture includes carbon dioxide, a surfactant, and water in the form of water-in-CO2 microemulsions. In one particular embodiment, the ratio of water-to-surfactant mixed together in the CO2 has a range of about 5-100 molecules of water per molecule of surfactant (e.g., about 5-30 molecules of water per molecule of surfactant).
    Type: Grant
    Filed: August 3, 2011
    Date of Patent: March 29, 2016
    Assignee: University of South Carolina
    Inventors: Michael A. Matthews, Pedro J. Tarafa
  • Patent number: 9260595
    Abstract: A solvent composition and system is disclosed having a composition including n-propyl bromide and a propionate containing liquid and/or a butyrate containing liquid. The solvent system may include approximately 35 to 92.5 weight percent propionate containing liquid and approximately 7.5 to 65 weight percent n-propyl bromide. Alternatively, the solvent system may include approximately 40 to 85 weight percent butyrate containing liquid and 15 to 60 weight percent n-propyl bromide. The solvent system may incorporate a polymer, such as a synthetic rubber polymer. Further the solvent system preferably has high solvency while maintaining desirable evaporation rates and is preferably nonflammable, combustible, or minimally a class IC flammable liquid.
    Type: Grant
    Filed: August 26, 2014
    Date of Patent: February 16, 2016
    Assignee: ZYP COATINGS, INC.
    Inventor: Cressie E. Holcombe, Jr.
  • Patent number: 9126888
    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: Grant
    Filed: June 9, 2014
    Date of Patent: September 8, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
  • Patent number: 9120906
    Abstract: A composition including an effective amount of trans-1,3,3,3-tetrafluoropropene component combined with an effective amount of an alcohol selected from the group of methanol, ethanol, propanol, isopropanol, tert-butanol, isobutanol, 2-ethyl hexanol and any combination thereof, where the composition has azeotropic properties.
    Type: Grant
    Filed: July 25, 2014
    Date of Patent: September 1, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: James M. Bowman, Rajiv R. Singh, David J. Williams, Hang T. Pham, Justin L. Becker
  • Patent number: 8999190
    Abstract: The invention provides a heat transfer composition comprising R-1234ze (E), R-32 and 1,1,1,2-tetrafluoroethane (R-134a).
    Type: Grant
    Filed: December 18, 2012
    Date of Patent: April 7, 2015
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventor: Robert E Low
  • Patent number: 8999909
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,1,1,3,3-pentachloro-propane (240fa) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of HFC-245fa and HCFO-1233zd.
    Type: Grant
    Filed: February 23, 2012
    Date of Patent: April 7, 2015
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Hang T. Pham, Ryan Hulse
  • Patent number: 8974690
    Abstract: Compositions and methods based on the use of fluoroalkene containing from 3 to 4 carbon atoms and at least one carbon-carbon double bond, such as HFO-1214, HFO-HFO-1233, or HFO-1354, having properties highly beneficial in foaming and blowing agent applications, articles and methods.
    Type: Grant
    Filed: June 6, 2014
    Date of Patent: March 10, 2015
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh S. Tung, Rajiv R. Singh, Ian Shankland
  • Patent number: 8969279
    Abstract: This invention relates to solvent systems useful for foam nozzle cleaning, which solvent systems are formed by combining at least a brominated compound, an alcohol and a stabilizer in amounts such that the solvent system has no flash point.
    Type: Grant
    Filed: October 6, 2010
    Date of Patent: March 3, 2015
    Assignee: Albemarle Corporation
    Inventor: Hisashi Miwa
  • Patent number: 8961808
    Abstract: Azeotrope-like compositions are disclosed. The azeotrope-like compositions are mixtures of E-1-chloro-2,3,3,3-tetrafluoropropene with E-1,1,1,4,4,4-hexafluoro-2-butene or E-1,1,1,4,4,5,5,5-octafluoro-2-pentene. Also disclosed is a process of preparing a thermoplastic or thermoset foam by using such azeotrope-like compositions as blowing agents. Also disclosed is a process of producing refrigeration by using such azeotrope-like compositions. Also disclosed is a process of using such azeotrope-like compositions as solvents. Also disclosed is a process of producing an aerosol product by using such azeotrope-like compositions. Also disclosed is a process of using such azeotrope-like compositions as heat transfer media. Also disclosed is a process of extinguishing or suppressing a fire by using such azeotrope-like compositions. Also disclosed is a process of using such azeotrope-like compositions as dielectrics.
    Type: Grant
    Filed: October 19, 2012
    Date of Patent: February 24, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventor: Mark L Robin
  • Patent number: 8951358
    Abstract: The present invention relates, in part, to cleaning methods and solvent cleaning compositions including at least one hydrofluoro-olefin or hydrochlorofluoro-olefin solvent for use in connection with cleaning of metal parts, and in certain preferred embodiments cleaning metal parts to be used in an aircraft.
    Type: Grant
    Filed: February 28, 2014
    Date of Patent: February 10, 2015
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Kane D. Cook
  • Patent number: 8877087
    Abstract: Nonflammable compositions comprising fluorinated compounds selected from the group consisting of hydrofluoroalkanes, hydrofluoroalkenes, partially or perfluorinated aromatic compounds, hydrofluoroethers, and fluoroketones; 1,2-dichloroethylene, especially trans-1,2-dichloroethylene; and a stabilizer. These non-flammable compositions which preferably contain 1,1,1,3,3-pentafluorobutane, can be used especially as solvents for cleaning and defluxing electronic components and for degreasing metals. The compositions further may comprise a propellant, e.g. 1,1,1,2-tetrafluoroethane. These compositions are especially suitable as flushing agent.
    Type: Grant
    Filed: November 2, 2012
    Date of Patent: November 4, 2014
    Assignee: Solvay Fluor GmbH
    Inventors: Michael Marhold, Helge Rau, Karsten Borner, Christoph Meurer
  • Patent number: 8858823
    Abstract: A composition based on 3,3,3-trifluoropropene and ammonia, and to the use thereof, especially as a heat transfer fluid. A heat-transfer composition including the composition based on 3,3,3-trifluoropropene and ammonia and also one or more additives chosen from lubricants, stabilizers, surfactants, tracers, fluorescers, odorant agents and solubilizers, and mixtures thereof. A process for heating or cooling a fluid or a body by means of a vapor compression circuit containing a heat-transfer fluid, said process successively including evaporation of the heat-transfer fluid, compression of the heat-transfer fluid, condensation of the heat fluid and depressurization of the heat-transfer fluid, in which the heat-transfer fluid is a composition based on 3,3,3-trifluoropropene and ammonia.
    Type: Grant
    Filed: March 9, 2012
    Date of Patent: October 14, 2014
    Assignee: Arkema France
    Inventors: Wissam Rached, Jean-Christophe Boutier
  • Patent number: 8809254
    Abstract: Provided are azeotrope-like compositions comprising heptafluoropropane and trifluoroiodomethane and uses thereof, including use in refrigerant compositions, refrigeration systems, blowing agents, fire suppressant compositions, and aerosol propellants.
    Type: Grant
    Filed: October 28, 2013
    Date of Patent: August 19, 2014
    Assignee: Honeywell International Inc.
    Inventors: Rajiv Ratna Singh, Hang T. Pham, Robert G. Richard
  • Patent number: 8791167
    Abstract: A composition including an effective amount of trans-1,3,3,3-tetrafluoropropene component combined with an effective amount of an alcohol selected from the group of methanol, ethanol, propanol, isopropanol, tert-butanol, isobutanol, 2-ethyl hexanol and any combination thereof, where the composition has azeotropic properties.
    Type: Grant
    Filed: February 13, 2012
    Date of Patent: July 29, 2014
    Assignee: Honeywell International Inc.
    Inventors: James M. Bowman, Rajiv R. Singh, David J. Williams, Hang T. Pham, Justin L. Becker
  • Patent number: 8772213
    Abstract: The present invention relates to solvent compositions including an effective amount of 1-chloro-3,3,3-trifluoropropene and uses thereof. In certain aspects, such solvent compositions may be applied to the surface of an article or portion of an article having an ink or ink-based marking so as to remove the ink or ink-based marking without deleteriously impacting the article or surface of the article.
    Type: Grant
    Filed: December 20, 2012
    Date of Patent: July 8, 2014
    Assignee: Honeywell International Inc.
    Inventors: Barbara Ruth DeCaire, Ryan Hulse, Diana Mercier, Kane D. Cook
  • Patent number: 8758640
    Abstract: Nonflammable compositions comprising fluorinated compounds selected from the group consisting of hydrofluoroalkanes, hydrofluoroalkenes, partially or perfluorinated aromatic compounds, hydrofluoroethers, and fluoroketones; 1,2-dichloroethylene, especially trans-1,2-dichloroethylene; and a stabilizer. These non-flammable compositions which preferably contain 1,1,1,3,3-pentafluorobutane, can be used especially as solvents for cleaning and defluxing electronic components and for degreasing metals. The compositions further may comprise a propellant, e.g. 1,1,1,2-tetrafluoroethane. These compositions are especially suitable as flushing agent.
    Type: Grant
    Filed: November 2, 2012
    Date of Patent: June 24, 2014
    Assignee: Solvay Fluor GmbH
    Inventors: Michael Marhold, Helge Rau, Karsten Borner, Christoph Meurer
  • Patent number: 8754024
    Abstract: A liquefied-gas aerosol dusting composition for preventing inhalation abuse incidents. The composition comprises at least one liquefied gas and Sucrose Octaacetate wherein the concentration of said aerosol dusting composition ranges from 5 ppm to about 50 ppm.
    Type: Grant
    Filed: February 26, 2013
    Date of Patent: June 17, 2014
    Inventors: Michael Scott Fishman, Neal Markus
  • Patent number: 8741829
    Abstract: Provided are azeotrope-like compositions comprising tetrafluoropropene and hydrofluorocarbons and uses thereof, including use in refrigerant compositions, refrigeration systems, blowing agent compositions, and aerosol propellants.
    Type: Grant
    Filed: March 26, 2012
    Date of Patent: June 3, 2014
    Assignee: Honeywell International Inc.
    Inventors: Rajiv R. Singh, Hang T. Pham, Gary Knopeck
  • Patent number: 8669222
    Abstract: Compositions and methods for release of adherent deposits from nonporous surfaces and substrates are provided. The compositions are low volatile organic compound (low VOC) compositions, solutions or mixtures that can be applied in a form that clings to the underlying surface while it is working. Adherent deposits removed using the compositions include grease and oil, and printers ink. The compositions may be used on any nonporous surface or substrate including metals, ceramics and plastics, without harming the surface or substrate. The composition may contain a thixotropic agent to act as an anti-shearing agent.
    Type: Grant
    Filed: April 12, 2012
    Date of Patent: March 11, 2014
    Inventor: Gregg Motsenbocker
  • Patent number: 8637443
    Abstract: The invention provides solvent and cleaning compositions comprising an ionic surfactant, which preferably has a fluorinated portion thereof, and a solvent selected from hydrofluoro- and/or hydrochlorofluoro-olefins. Additionally, the invention provides drying, dry cleaning, and soil repellency compositions containing a hydrofluoro- or hydrochlorofluoro-olefin and said surfactant. Additionally, the invention provides drying compositions containing a hydrofluoro-olefin or hydrochlorofluoro-olefin and an alcohol such as methanol, ethanol or isopropanol.
    Type: Grant
    Filed: December 17, 2009
    Date of Patent: January 28, 2014
    Assignee: Honeywell International Inc.
    Inventors: Rajat Basu, Gary Zyhowski, Kane Cook, David Nalewajek
  • Patent number: 8623808
    Abstract: Disclosed are compositions useful in a wide variety of applications, including heat transfer fluids which possess a highly desirable and unexpectedly superior combination of properties, and heat transfer systems and methods based on these fluids. The preferred heat transfer fluid comprises from about 1 to about 40 percent, on a weight basis, of carbon dioxide (CO2) and from about 99 to about 60 percent, on a weight basis, of a compound having the Formula I XCFzR3-z (I), where X is a C2 or a C3 unsaturated, substituted or unsubstituted, alkyl radical, each R is independently Cl, F, Br, I or H, and z is 1 to 3. A preferred compound of Formula I is tetrafluoropropene, particularly 1,1,1,3-tetrafluoropropene and/or 1,1,1,3-tetrafluoropropene.
    Type: Grant
    Filed: August 5, 2011
    Date of Patent: January 7, 2014
    Assignee: Honeywell International Inc.
    Inventors: Rajiv R. Singh, Hang T. Pham, Ian Shankland
  • Patent number: 8618040
    Abstract: Compositions and methods based on the use of fluoroalkene containing from 3 to 4 carbon atoms and at least one carbon-carbon double bond, such as HFO-1214, HFO-HFO-1233, or HFO-1354, having properties highly beneficial in foaming and blowing agent applications, articles and methods.
    Type: Grant
    Filed: July 7, 2011
    Date of Patent: December 31, 2013
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh Sung Tung, Rajiv Ratna Singh, Ian Shankland
  • Patent number: 8598107
    Abstract: Provided are azeotrope-like compositions comprising heptafluoropropane and trifluoroiodomethane and uses thereof, including use in refrigerant compositions, refrigeration systems, blowing agents, fire suppressant compositions, and aerosol propellants.
    Type: Grant
    Filed: January 13, 2009
    Date of Patent: December 3, 2013
    Assignee: Honeywell International Inc.
    Inventors: Rajiv Ratna Singh, Hang T. Pham, Robert Gerard Richard
  • Patent number: 8557759
    Abstract: A flushing solvent for flushing an HVAC-R system is a mixture of hydrofluoroether, acetone, t-Butyl acetate, and trans 1,2 Dichloroethylene.
    Type: Grant
    Filed: December 6, 2011
    Date of Patent: October 15, 2013
    Assignee: Diversitech Corporation
    Inventor: Anthony Edward Jernigan
  • 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
  • Patent number: 8519200
    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: Grant
    Filed: February 23, 2012
    Date of Patent: August 27, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hang T. Pham, Hsueh Sung Tung, Ryan Hulse
  • Patent number: 8492327
    Abstract: Provided are azeotrope-like compositions comprising difluoromethane and trifluoroiodomethane and uses thereof, including use in refrigerant compositions, refrigeration systems, blowing agent compositions, and aerosol propellants.
    Type: Grant
    Filed: April 23, 2012
    Date of Patent: July 23, 2013
    Assignee: Honeywell International Inc.
    Inventors: Rajiv R. Singh, Hang T. Pham, David P. Wilson
  • Patent number: 8420706
    Abstract: Various uses of fluoroalkenes, including tetrafluoropropenes, particularly (HFO-1234) in a variety of applications, including as blowing agents are disclosed.
    Type: Grant
    Filed: September 27, 2007
    Date of Patent: April 16, 2013
    Assignee: Honeywell International Inc.
    Inventors: James M. Bowman, David J. Williams, Rajiv R. Singh, Ian Shankland
  • Patent number: 8415255
    Abstract: A micellar solution is used to seal pores exposed at the bottom and sidewall surfaces of a structure etched in or through a porous low dielectric constant material. The micellar solution is also effective to clean away etch residues from the etched structure.
    Type: Grant
    Filed: August 5, 2005
    Date of Patent: April 9, 2013
    Assignee: Freescale Semiconductor, Inc.
    Inventor: Balgovind Sharma
  • Patent number: 8378158
    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: October 5, 2011
    Date of Patent: February 19, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham
  • Publication number: 20130037058
    Abstract: The invention relates to the use of a liquid composition including 1-chloro-3,3,3-trifluoropropene and 1,2-transdichloroethylene for cleaning solid surfaces, the 1-chloro-3,3,3-trifluoropropene and the 1,2-transdichloroethylene being at least 99 wt % of the composition. The invention also relates to a liquid composition containing 1-chloro-3,353-trifluoropropene and 1,2-transdichloroethylene, the 1-chloro-3,3,34triluoropropene and 1,2-transdichloroethylene being at least 99 wt % of the composition and the weight ratio of the 1-chloro-3,3,3?trifluoropropene over the 1,2-transdichloroethylene being between 57:43 and 65:35, preferably between 58:42 and 63:37, and more preferably between 59:41 and 61:39.
    Type: Application
    Filed: January 13, 2011
    Publication date: February 14, 2013
    Applicant: Arkema France
    Inventor: Laurent Abbas
  • Patent number: 8354039
    Abstract: Halocarbons of the structure CF3CF2CH2X, wherein X is either F or Cl or mixtures thereof prepared by: contacting at least one 2-fluorochloropropane with hydrogen fluoride in a first fluorination step in the gas phase or liquid phase under substantially anhydrous conditions, in the absence of added catalyst to partially fluorinate said 2-fluorochloropropane; contacting said partially fluorinated 2-fluorochloropropane with at least the stoichiometric molar equivalent of hydrogen fluoride under substantially anhydrous conditions, in the presence of at least one fluorination catalyst in a second fluorination step; removing said reaction products from contact with said catalyst, and isolating a substantial yield of at least 1,1,1,2,2,3-hexafluoropropane or 1,1,1,2,2, penta-3-chloropropane, or mixtures thereof, respectively.
    Type: Grant
    Filed: June 6, 2011
    Date of Patent: January 15, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert, Jeffrey P. Knapp
  • Patent number: 8333901
    Abstract: The invention provides a heat transfer composition comprising R-1234ze(E), R-32 and 1,1,1,2-tetrafluoroethane (R-134a).
    Type: Grant
    Filed: February 16, 2011
    Date of Patent: December 18, 2012
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventor: Robert E. Low
  • Patent number: 8247366
    Abstract: 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: Grant
    Filed: August 4, 2011
    Date of Patent: August 21, 2012
    Assignee: Honeywell International Inc.
    Inventors: Hsueh S. Tung, Hang T. Pham, Rajiv R. Singh, Daniel C. Merkel, Robert Johnson
  • Patent number: 8245512
    Abstract: Use of working fluids for energy conversion in a thermal Organic Rankine Cycle (ORC) process for combined generation of electrical and heat energy. The heat source used in the ORC process is in particular thermal water. The working fluids used in the ORC process are partially or perfluorinated hydrocarbons and/or partially or perfluorinated polyethers and/or partially or perfluorinated ketones. In some embodiments, the working fluid used is a combination of 1,1,1,3,3-pentafluorobutane and a fluorinated polyether having a molecular weight of 340 and a boiling point of 57° C. at 101.3 kPa, or a combination of 1,1,1,3,3-pentafluorobutane and at least one partially or perfluorinated ketone.
    Type: Grant
    Filed: March 11, 2011
    Date of Patent: August 21, 2012
    Assignee: SOLVAY FLUOR GmbH
    Inventors: Martin Schwiegel, Felix Flohr, Christoph Meurer
  • Patent number: 8193398
    Abstract: A process for oxygen-initiated hydrobromination of propene to form a crude reaction mixture of 95 GC area % n-propyl bromide. The process includes feeding an oxygen-containing gas, propene and hydrogen bromide into a liquid phase mixture comprised of n-propyl bromide and hydrogen bromide. At least the oxygen-containing gas and the propene of the feed are fed subsurface to the liquid phase mixture and either (a) the oxygen-containing gas and the propene do not come together in the absence of hydrogen bromide or (b) the oxygen-containing gas and the propene come together only in a propene:oxygen molar ratio in the range of 145:1 to 180:1. Purification processes provide a propyl bromide product containing at least 99.7 GC area % n-propyl bromide. Also provided is a novel composition of enhanced thermal stability which comprises a mixture of n-propyl bromide and isopropyl bromide. The mixture has an n-propyl bromide content of at least 99.7 GC area %, and an isopropyl bromide content of no more than 0.
    Type: Grant
    Filed: April 13, 2006
    Date of Patent: June 5, 2012
    Assignee: Albemarle Corporation
    Inventors: William B. Harrod, Bonnie G. McKinnie, Alireza M. Dadgar, Tyson J. Hall
  • Patent number: 8163689
    Abstract: Provided are azeotrope-like compositions comprising difluoromethane and trifluoroiodomethane and uses thereof, including use in refrigerant compositions, refrigeration systems, blowing agent compositions, and aerosol propellants.
    Type: Grant
    Filed: December 15, 2008
    Date of Patent: April 24, 2012
    Assignee: Honeywell International Inc.
    Inventors: Rajiv R. Singh, Hang T. Pham, David P. Wilson
  • Patent number: 8153018
    Abstract: 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: Grant
    Filed: September 30, 2011
    Date of Patent: April 10, 2012
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh Sung Tung
  • Patent number: 8148317
    Abstract: Provided are azeotrope-like compositions comprising tetrafluoropropene and hydrofluorocarbons and uses thereof, including use in refrigerant compositions, refrigeration systems, blowing agent compositions, and aerosol propellants.
    Type: Grant
    Filed: July 28, 2009
    Date of Patent: April 3, 2012
    Assignee: Honeywell International Inc.
    Inventors: Rajiv R. Singh, Hang T. Pham, Gary Knopeck, Louis E. Herena, Jeremy N. Diringer
  • Patent number: 8133407
    Abstract: Provided is a composition comprising (a) at least one halogenated compound selected from the group consisting of C3-C5 hydrofluoroolefin, CF3I, and combinations thereof, and (b) an effective stabilizing amount of a sesquiterpene selected from the group consisting of farnesol, farnesene, and mixtures thereof.
    Type: Grant
    Filed: May 15, 2009
    Date of Patent: March 13, 2012
    Assignee: Honeywell International Inc.
    Inventors: Gary Zyhowski, Rajiv Ratna Singh, Raymond H. Thomas, Mark W. Spatz, Roy P. Robinson, George J. Samuels, Gregory J. Shafer, Michael Van Der Puy, David P. Wilson, John L. Welch, Ronald P. Vogl, Samuel F. Yana Motta
  • Patent number: 8133406
    Abstract: A process is disclosed for making CF3CF?CH2 or mixtures thereof with CHF2CF?CHF. This process involves (a) reacting CHCl2CF2CF3, and optionally CHClFCF2CClF2, with H2 in the presence of a catalytically effective amount of a hydrogenation catalyst to form CH3CF2CF3 and, when CHClFCF2CClF2 is present, CH2FCF2CHF2; (b) dehydrofluorinating CH3CF2CF3, and optionally any CH2FCF2CHF2, from (a) to form a product mixture including CF3CF?CH2 and, if CH2FCF2CHF2 is present, CHF2CF?CHF; and optionally (c) recovering CF3CF?CH2, or a mixture thereof with CHF2CF?CHF from the product mixture formed in (b) and/or (d) separating at least a portion of any CHF2CF?CHF in the product mixture formed in (b) from the CF3CF?CH2 in the product mixture formed in (b).
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: March 13, 2012
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 8114828
    Abstract: A composition including an effective amount of trans-1,3,3,3-tetrafluoropropene component combined with an effective amount of an alcohol selected from the group of methanol, ethanol, propanol, isopropanol, tert-butanol, isobutanol, 2-ethyl hexanol and any combination thereof, where the composition has azeotropic properties.
    Type: Grant
    Filed: April 16, 2007
    Date of Patent: February 14, 2012
    Assignee: Honeywell International Inc.
    Inventors: Jim M Bowman, David J Williams, Rajiv R Singh, Hang T Pham, Justin L Becker
  • Patent number: 8101672
    Abstract: The invention pertains to azeotrope-like compositions of 1,1,2,3,3-pentafluoropropene (HFC-1225yc) and any one of 1,1,1,2-tetrafluoropropene (HFC-1234yf) or the Z-isomer of 1,1,1,2,3-pentafluoropropene (HFC-1225yeZ), and uses thereof, including use in refrigerant compositions, refrigeration systems, blowing agent compositions, and aerosol propellants.
    Type: Grant
    Filed: December 13, 2007
    Date of Patent: January 24, 2012
    Assignee: Honeywell International Inc.
    Inventors: Ryan J. Hulse, Hang T. Pham, Rajiv R. Singh
  • Publication number: 20110289748
    Abstract: Disclosed are compositions useful in a wide variety of applications, including heat transfer fluids which possess a highly desirable and unexpectedly superior combination of properties, and heat transfer systems and methods based on these fluids. The preferred heat transfer fluid comprises from about 1 to about 40 percent, on a weight basis, of carbon dioxide (CO2) and from about 99 to about 60 percent, on a weight basis, of a compound having the Formula I XCFzR3-z (I), where X is a C2 or a C3 unsaturated, substituted or unsubstituted, alkyl radical, each R is independently Cl, F, Br, I or H, and z is 1 to 3. A preferred compound of Formula I is tetrafluoropropene, particularly 1,1,1,3-tetrafluoropropene and/or 1,1,1,3-tetrafluoropropene.
    Type: Application
    Filed: August 5, 2011
    Publication date: December 1, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: RAJIV R. SINGH, HANG T. PHAM, IAN SHANKLAND
  • Patent number: 8062429
    Abstract: The present invention relates to aqueous compositions comprising amidoxime compounds and methods for cleaning plasma etch residue from semiconductor substrates including such dilute aqueous solutions. The compositions of the invention may optionally contain one or more other acid compounds, one or more basic compounds, and a fluoride-containing compound and additional components such as organic solvents, chelating agents, amines, and surfactants. The invention also relates to a method of removing residue from a substrate during integrated circuit fabrication.
    Type: Grant
    Filed: October 29, 2008
    Date of Patent: November 22, 2011
    Assignee: EKC Technology, Inc.
    Inventor: Wai Mun Lee
  • Patent number: 8053403
    Abstract: The subject of the invention is a composition comprising (i) from 10% to 25% by weight of 1,1,1,3,3-pentafluorobutane, preferably 16% to 24% by weight of 1,1,1,3,3-pentafluorobutane; (ii) from 62% to 70% by weight of trans-dichloroethylene, preferably from 63% to 68% by weight of trans-dichloroethylene, (iii) from 10% to 21% by weight of nonafluoromethoxybutane, preferably from 11% to 17% by weight of nonafluoromethoxybutane; and; (iv) from 1% to 4% by weight of nonafluoroethoxybutane, preferably from 2% to 4% by weight of nonafluoroethoxybutane. The subject matter of the invention is also to the use of said composition as a cleaning, solvent, degreasing, defluxing or drying agent.
    Type: Grant
    Filed: October 2, 2009
    Date of Patent: November 8, 2011
    Assignee: Arkema France
    Inventor: Laurent Abbas
  • Patent number: 8053404
    Abstract: Disclosed are compositions useful in a wide variety of applications, including heat transfer fluids which possess a highly desirable and unexpectedly superior combination of properties, and heat transfer systems and methods based on these fluids. The preferred heat transfer fluid comprises from about 1 to about 40 percent, on a weight basis, of carbon dioxide (CO2) and from about 99 to about 60 percent, on a weight basis, of a compound having the Formula I XCFzR3-z (I), where X is a C2 or a C3 unsaturated, substituted or unsubstituted, alkyl radical, each R is independently Cl, F, Br, I or H, and z is 1 to 3. A preferred compound of Formula I is tetrafluoropropene, particularly 1,1,1,3-tetrafluoropropene and/or 1,1,1,3-tetrafluoropropene.
    Type: Grant
    Filed: September 11, 2009
    Date of Patent: November 8, 2011
    Assignee: Honeywell International Inc.
    Inventors: Rajiv R. Singh, Hang T. Pham, Ian Shankland