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).

  • Publication number: 20160221898
    Abstract: The invention relates to a separation process whereby 2-chloro-3,3,3-trifluoropropene (1233xf) is separated from a mixture containing other fluorinated organics and high boiling materials such as dimers using azeotropes of HF formed by adding appropriate amounts to the mixture which facilitate separation by, e.g. distillation.
    Type: Application
    Filed: April 8, 2016
    Publication date: August 4, 2016
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou WANG, Selma BEKTESEVIC, Daniel C. MERKEL, Hsueh SUNG TUNG, Konstantin A. POKROVSKI
  • Publication number: 20160214914
    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: Application
    Filed: November 9, 2015
    Publication date: July 28, 2016
    Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
  • Patent number: 9399609
    Abstract: The present process relates to a method for minimizing the formation of 1,1,1,2,2-pentafluoropropane in a liquid phase reaction of 2-chloro-3,3,3-trifluoropropene and HF in the presence of a hydrofluorination catalyst comprising: (a) reacting HF with sufficient amount of 2-chloro-3,3,3-trifluoropropene in the presence of a hydrofluorination catalyst under conditions effective to form 2-chloro-1,1,1,2-tetrafluoropropane, the hydrofluorination catalyst being present in sufficient amounts to catalyze said reaction and the 2-chloro-1,1,1,2-tetrafluoropropane being formed with both a conversion of greater than 80% and a 1,1,1,2,2-pentafluoropropane selectivity lower than 20%; and (b) maintaining the 2-chloro-1,1,1,2-tetrafluoropropane being formed with both a conversion of about 80% or more and a 1,1,1,2,2-pentafluoropropane selectivity of about 20% or less by adding said hydrofluorination catalyst to the reactor in small increments.
    Type: Grant
    Filed: March 11, 2014
    Date of Patent: July 26, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Daniel C. Merkel, Hsueh Sung Tung, Haluk Kopkalli
  • Patent number: 9394217
    Abstract: The invention relates to a process to produce 244bb from 1233xf in multiple reaction zones whereby the 1233xf starting material is at least 95% converted to 244bb and by-product such as 245cb forms in amounts less than about 2%.
    Type: Grant
    Filed: March 12, 2014
    Date of Patent: July 19, 2016
    Assignee: HONEYWELL INTERNATIONAL, INC.
    Inventors: Yuon Chiu, Haluk Kopkalli, Robert A. Smith, Daniel C. Merkel
  • Publication number: 20160194261
    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: January 4, 2016
    Publication date: July 7, 2016
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Publication number: 20160185692
    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: Application
    Filed: October 19, 2015
    Publication date: June 30, 2016
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9359273
    Abstract: The present invention relates, in part, to the discovery that the presence of impurities in 1,1,2,3-tetrachloropropene (1230xa) results in catalyst instability during the fluorination of 1230xa to 2-chloro-3,3,3-trifluoropropene. By substantially removing the impurities, it is shown that the catalyst life is extended and results in improved operation efficiency of the fluorination reaction. Such steps similarly result in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf).
    Type: Grant
    Filed: October 11, 2012
    Date of Patent: June 7, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Selma Bektesevic, Daniel C. Merkel, Mario Joseph Nappa, Xuehui Sun, Hsueh Sung Tung, Haiyou Wang
  • Patent number: 9353029
    Abstract: The invention relates to a process to prepare tetrahalopropenes, such as 2-chloro-3,3,3-trifluoropropene (1233xf). The process comprises atomizing a feed material, such as 1,1,2,3-tetrachloropropene (1230xa) and the like, and mixing it with superheated HF to form a vaporized composition of feed material and HF with substantially instantaneous contact with a vapor phase fluorination catalyst. The invention extends catalyst life and forestalls catalyst deactivation.
    Type: Grant
    Filed: March 12, 2014
    Date of Patent: May 31, 2016
    Assignee: HONEYWELL INTERNATIONAL, INC.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Haiyou Wang, Haluk Kopkalli, Yuon Chiu
  • Patent number: 9353028
    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: Grant
    Filed: February 10, 2015
    Date of Patent: May 31, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Barry Asher Mahler, Hsueh Sung Tung, Mario Joseph Nappa
  • Patent number: 9334207
    Abstract: Disclosed is an integrated manufacturing process to co-produce (E)1-chloro-3,3,3-trifluoropropene, (E)1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single chlorinated hydrocarbon feed stock, 240fa. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E)1-chloro-3,3,3-trifluoropropene (1233zd(E)) from 240fa. In the second liquid phase fluorination reactor 1233zd(E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E)1,3,3,3-tetrafluoropropene (1234ze(E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst. This operation may be followed by one or more purification processes to recover the 1234ze(E) product.
    Type: Grant
    Filed: August 29, 2011
    Date of Patent: May 10, 2016
    Assignee: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung, Ian Shankland
  • Patent number: 9334210
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,1,3,3-tetrachloroprop-1-ene (HCO-1230za) and hydrogen fluoride. Such compositions are useful as feed stock in the production of HFC-245fa and HCFO-1233zd.
    Type: Grant
    Filed: March 13, 2013
    Date of Patent: May 10, 2016
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Stephen A. Cottrell, Hang T. Pham
  • Patent number: 9334206
    Abstract: The invention relates to a separation process whereby 2-chloro-3,3,3-trifluoropropene (1233xf) is separated from a mixture containing other fluorinated organics and high boiling materials such as dimers using azeotropes of HF formed by adding appropriate amounts to the mixture which facilitate separation by, e.g. distillation.
    Type: Grant
    Filed: March 11, 2014
    Date of Patent: May 10, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Selma Bektesevic, Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Publication number: 20160083317
    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: Application
    Filed: December 1, 2015
    Publication date: March 24, 2016
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Haiyou Wang, Ryan Hulse
  • Patent number: 9290424
    Abstract: In certain aspects, the present invention relates to methods for increasing the cost efficiency and safety of the hydrogenation of a fluorinated olefin by controlling the reaction conditions and parameters. In further aspects, the hydrogenation reaction is provided in a two stage reaction wherein the reactant amounts, temperature and other parameters are controlled such that the conversion percentage, selectivity, and reaction parameters are all within commercially acceptable levels.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: March 22, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Stephen A. Cottrell, John J. Senetar, Hsueh S. Tung, Daniel C. Merkel, Yuon Chiu, Haluk Kopkalli
  • 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: 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: 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