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: 9102579
    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: Grant
    Filed: January 3, 2007
    Date of Patent: August 11, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Barbara A. Light, Steven D. Phillips, Kim M. Fleming, Susan A. Ferguson, Jing Ji Ma, Cheryl L. Bortz, Michael Van Der Puy, Daniel C. Merkel, Hsueh S. Tung, Sudip Mukhopadhyay
  • Publication number: 20150183697
    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: Application
    Filed: March 10, 2015
    Publication date: July 2, 2015
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Haseh S. Tung, Haiyou Wang
  • Publication number: 20150183698
    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: Application
    Filed: March 10, 2015
    Publication date: July 2, 2015
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Haseh S. Tung, Haiyou Wang
  • Patent number: 9067856
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ??(II) where Z is H, F, Cl, I or Br.
    Type: Grant
    Filed: August 12, 2014
    Date of Patent: June 30, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
  • Publication number: 20150166442
    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: Application
    Filed: February 27, 2015
    Publication date: June 18, 2015
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Hang T. Pham, Ryan Hulse
  • Publication number: 20150152028
    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 the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Application
    Filed: January 26, 2015
    Publication date: June 4, 2015
    Inventors: Robert C. Johnson, Daniel C. Merkel
  • Patent number: 9045386
    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: Grant
    Filed: February 2, 2011
    Date of Patent: June 2, 2015
    Assignee: Honeywell International Inc.
    Inventors: Hsueh S. Tung, Robert Johnson, Konstantin A. Pokrovski, Daniel C. Merkel
  • Patent number: 9024092
    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: Grant
    Filed: December 4, 2009
    Date of Patent: May 5, 2015
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Robert C. Johnson, 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
  • Publication number: 20150105595
    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: Application
    Filed: December 15, 2014
    Publication date: April 16, 2015
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • 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: 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
  • Patent number: 8952208
    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 the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Grant
    Filed: June 28, 2010
    Date of Patent: February 10, 2015
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Daniel C. Merkel
  • Publication number: 20150034523
    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: Application
    Filed: August 11, 2014
    Publication date: February 5, 2015
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk KOPKALLI, Haiyou WANG, Hsueh SUNG TUNG, Daniel C. MERKEL
  • Patent number: 8927791
    Abstract: The current invention relates to a process for making a tetrafluoropropene using a tetrafluorochloropropane and/or a pentafluoropropane as starting or intermediate reagents. More specifically, though not exclusively, the present invention relates to a novel method for preparing a tetrafluoropropene by dehydrohalogenating a starting or intermediate tetrafluorochloropropane and/or pentafluoropropane material in the presence of a caustic solution at a temperature range greater than 40° C. and less than or equal to 80° C.
    Type: Grant
    Filed: March 28, 2011
    Date of Patent: January 6, 2015
    Assignee: Honeywell International Inc.
    Inventors: Selma Bektesevic, Hsueh S. Tung, Haiyou Wang, Daniel C. Merkel, Robert C. Johnson
  • 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
  • Patent number: 8916733
    Abstract: A process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of contacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of a catalyst having about 25 to about 99.9 mole percent antimony pentachloride and about 0.1 to about 75 mole percent of a metal of a Lewis acid under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane. There is a second process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating about 75 to about 99.9 mole percent 2-chloro-3,3,3-trifluoropropene and about 0.1 to about 25 mole percent of one or more other hydrocarbons having at least one chlorine atom in the presence of a catalyst of fluorinated antimony pentachloride under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane. There is yet another process for hydrofluorinating 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane.
    Type: Grant
    Filed: June 15, 2009
    Date of Patent: December 23, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
  • Patent number: 8912368
    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: January 16, 2013
    Date of Patent: December 16, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 8907146
    Abstract: Disclosed is a process in which the fluorination of an organic reactant comprising 1,1,1,3,3-pentachloropropane (240fa) with anhydrous HF is conducted in the presence of an effective amount of a phase-transfer catalyst which facilitates the reaction between these incompatible reaction components to produce 1-chloro-3,3,3-trifluoro-propene (1233zd). Other organic reactant materials include 1,1,3,3-tetrachloropropene (HCO-1230za), 1,3,3,3-tetrachloropropene (HCO-1230zd), and various mixtures with or without 240fa.
    Type: Grant
    Filed: January 30, 2014
    Date of Patent: December 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Haiyou Wang, Daniel C. Merkel, Stephen A. Cottrell, Konstantin A. Pokrovski, Ian Shankland
  • Publication number: 20140350311
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3 ??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3 ??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ ??(II) where Z is H, F, Cl, I or Br.
    Type: Application
    Filed: August 12, 2014
    Publication date: November 27, 2014
    Inventors: ROBERT C. JOHNSON, HSUEH S. TUNG, DANIEL C. MERKEL