Patents by Inventor Daniel C. Merkel

Daniel C. Merkel has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 9272968
    Abstract: This invention relates to a process for the suppression of 3,3,3-trifluoropropyne during the manufacture of fluorocarbons, fluoroolefins, hydrochlorofluoroolefins. More particularly, this invention is directed to a process to suppress the formation of 3,3,3-trifluoropropyne during processes for the manufacture of HCFO-1233zd(E), HCFO-1233zd(Z), HFO-1234ze(E), and/or HFO-1234ze(Z).
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: March 1, 2016
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Jeffrey A. Ball, Yuon Chiu, Hsueh Sung Tung, Konstantin A. Pokrovski, Daniel C. Merkel
  • Patent number: 9272969
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,3,3-trichloro-1,1-difluoro-propane (HCFC-242fa) and hydrogen fluoride. Such compositions are useful as a feed stock or intermediate in the production of HFC-245fa and HCFO-1233zd.
    Type: Grant
    Filed: March 13, 2013
    Date of Patent: March 1, 2016
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Haiyou Wang, Stephen A. Cottrell, Hang T. Pham
  • 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
  • Publication number: 20160039729
    Abstract: Disclosed is a process for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of Formula (I): C(X)3CF2C(X)3??(I) to at least one compound of Formula (II) CF3CF?CHZ??(II) where each X and Z is independently H, F, Cl, I or Br, said process preferably not including any substantial amount of oxygen-containing catalyst in certain embodiments. Preferably Z is H.
    Type: Application
    Filed: August 10, 2015
    Publication date: February 11, 2016
    Inventors: Hsueh S. Tung, Sudip Mukhopadhyay, Michael Van Der Puy, Daniel C. Merkel, Jing Ji Ma, Cheryl L. Bortz, Barbara A. Light, Steven D. Phillips, Kim M. Fleming, Susan A. Ferguson
  • Patent number: 9242910
    Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, co-feed species HFC-245cb is added to the reaction at a pressure of at least about 100 psig; and in another embodiment it is added to maintain a mole ratio of HFC-245cb to HCFO-1233xf of between about 0.005:1 to about 1:1. The HFC-245cb may be added as recycled by-product of the reaction and/or added as fresh feed. The HFC-245cb provides elevated pressures to the reaction thereby facilitating reactor operation, mixing and HCFC-244bb product removal. Other co-feed species are also disclosed.
    Type: Grant
    Filed: March 13, 2014
    Date of Patent: January 26, 2016
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
  • Patent number: 9233895
    Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, one or more co-feed species having a normal boiling point of between about ?80° C. to about 0° C., such as HFC-245cb, is added to the reaction at a pressure of at least about 100 psig; and in another embodiment it is added to maintain a mole ratio of HFC-245cb to HCFO-1233xf of between about 0.005:1 to about 1:1. The HFC-245cb may be added as recycled by-product of the reaction and/or added as fresh feed. The HFC-245cb provides elevated pressures to the reaction thereby facilitating reactor operation, mixing and HCFC-244bb product removal. Other co-feed species are also disclosed.
    Type: Grant
    Filed: April 24, 2015
    Date of Patent: January 12, 2016
    Assignee: HONEYWELL INTERNATIONAL, INC.
    Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
  • Patent number: 9228128
    Abstract: The present invention relates in part to a container for stabilized chloropropenes, such as 1,1,2,3-tetrachloropropene, otherwise known to decompose and degrade, and to the resulting stabilized chloropropene, using a morpholine compound and/or a trialkyl phosphate compound as defined herein. Such stabilized chloropropenes are useful in the manufacture of hydrofluoroolefins such as 2,3,3,3-tetrafluoroprop-1-ene (1234yf).
    Type: Grant
    Filed: August 11, 2014
    Date of Patent: January 5, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk Kopkalli, Haiyou Wang, Hsueh Sung Tung, Daniel C. Merkel
  • Patent number: 9227893
    Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
    Type: Grant
    Filed: December 15, 2014
    Date of Patent: January 5, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9222177
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,3,3,3-tetrachloroprop-1-ene (HCO-1230zd) and hydrogen fluoride. Such compositions are useful as a feed stock in the production of HFC245fa and HCFO1233zd.
    Type: Grant
    Filed: March 13, 2013
    Date of Patent: December 29, 2015
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Ryan Hulse, Hang T. Pham
  • Publication number: 20150361014
    Abstract: Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl3, SbCl5, SbF5, TiCl4, SnCl4, Cr2O3, and fluorinated Cr2O3.
    Type: Application
    Filed: May 5, 2015
    Publication date: December 17, 2015
    Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
  • Patent number: 9211483
    Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.
    Type: Grant
    Filed: January 30, 2014
    Date of Patent: December 15, 2015
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
  • Patent number: 9181151
    Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Grant
    Filed: September 9, 2013
    Date of Patent: November 10, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
  • Publication number: 20150315108
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2?CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl?CH2, preferably in a 80-96% selectivity. The CF3CCl?CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl?CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3.
    Type: Application
    Filed: May 5, 2014
    Publication date: November 5, 2015
    Inventors: SUDIP MUKHOPADHYAY, Hsueh S. Tung, Michael Van der Puy, Daniel C. Merkel, Jing Ji Ma, Cheryl L. Bortz, Barbara A. Light, Steven D. Phillips, Rajesh K. Dubey
  • Patent number: 9162947
    Abstract: Disclosed are processes for a high temperature isomerization reaction converting (E)-1-chloro-3,3,3-trifluoropropene to (Z)-1-chloro-3,3,3-trifluoropropene. In certain aspects of the invention, such a process includes contacting a feed stream with a heated surface, where the feed stream includes (E)-1-chloro-3,3,3-trifluoropropene or mixture of (E)-1-chloro-3,3,3-trifluoropropene with (Z)-1-chloro-3,3,3-trifluoropropene. The resulting product stream includes (Z)-1-chloro-3,3,3-trifluoropropene and (E)-1-chloro-3,3,3-trifluoropropene, where the ratio of (Z) isomer to (E) isomer in the product stream is higher than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.
    Type: Grant
    Filed: March 11, 2014
    Date of Patent: October 20, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9139499
    Abstract: Provided are methods for forming 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 27, 2015
    Date of Patent: September 22, 2015
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Hang T. Pham, Ryan Hulse
  • Publication number: 20150225316
    Abstract: The present invention relates to a hydrofluorinating process which comprises reacting a fluoroolefin with hydrogen fluoride in the liquid phase in the presence of a hydrofluorination catalyst in the reaction zone of a reactor, said reactor comprised of a reactor body having a length to diameter ratio of about 2:1 or greater; a stirred reaction zone containing said hydrofluorination catalyst, which may be prepared in situ, at least one inlet for supplying said hydrogen fluoride and fluoroolefin to the reaction zone and at least one outlet for recovering said fluoroalkane, said stirrer disposed in the reaction zone and comprising a plurality of blades fixedly attached to shaft drivable by a motor, said blades extending from about the bottom of the reaction zone to about the top of the reaction zone and said shaft extending on a longitudinal axis from the bottom of the reactor to the top of the reactor, said stirrer being rotated at a speed sufficient to promote a swirling of the liquid to effect the occurrence
    Type: Application
    Filed: February 10, 2015
    Publication date: August 13, 2015
    Inventors: Daniel C. MERKEL, Barry Asher MAHLER, Hsueh Sung TUNG, Mario Joseph NAPPA
  • Publication number: 20150225317
    Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, one or more co-feed species having a normal boiling point of between about ?80° C. to about 0° C., such as HFC-245cb, is added to the reaction at a pressure of at least about 100 psig; and in another embodiment it is added to maintain a mole ratio of HFC-245cb to HCFO-1233xf of between about 0.005:1 to about 1:1. The HFC-245cb may be added as recycled by-product of the reaction and/or added as fresh feed. The HFC-245cb provides elevated pressures to the reaction thereby facilitating reactor operation, mixing and HCFC-244bb product removal. Other co-feed species are also disclosed.
    Type: Application
    Filed: April 24, 2015
    Publication date: August 13, 2015
    Applicant: HONEWELL INTERNATIONAL, INC.
    Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
  • Publication number: 20150224470
    Abstract: The present invention relates to methods, process, and integrated systems for economically producing (E)-1-chloro-3,3,3-trifluoropropene via vapor phase and/or liquid processes.
    Type: Application
    Filed: April 28, 2015
    Publication date: August 13, 2015
    Inventors: Hsueh Sung Tung, Konstantin A. Pokrovski, Daniel C. Merkel, Robert Johnson
  • Publication number: 20150225315
    Abstract: A reactor apparatus is provided having a reaction chamber; a compartmentalizing apparatus including a plurality of compartments, each compartment being open at a top end and bottom end, the compartmentalizing apparatus being disposed within the reaction chamber; and an inlet disposed at an area of the reactor and in fluid communication between the reaction chamber and a feed source. Also provided is a reactor apparatus having an assembly having a reaction chamber; at least one agitator assembly configured to generate mixing within the reaction chamber, the agitator assembly including: a shaft partially lined or coated with a fluoropolymer or other non-metallic corrosion-resistant material, and an impeller lined or coated with the fluoropolymer or other non-metallic corrosion-resistant material; and an inlet disposed at an area of the reactor and in fluid communication between the reaction chamber and a feed source. The provided reactor apparatus can be utilized in hydrofluorination processes.
    Type: Application
    Filed: February 10, 2015
    Publication date: August 13, 2015
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk KOPKALLI, Yuon CHIU, Daniel C. MERKEL, Ron Joseph ROOF, Robert A. SMITH, Austin V. PRANKE
  • Patent number: 9102580
    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: Grant
    Filed: November 9, 2012
    Date of Patent: August 11, 2015
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Mario Joseph Nappa, Andrew Jackson, Daniel C. Merkel