Patents by Inventor Haluk Kopkalli

Haluk Kopkalli 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: 10351494
    Abstract: The present disclosure provides various manufacturing processes for the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf or 1234yf). Such methods may allow for the improved yields, more economical processes, and waste reduction in the production of 1234yf and subsequent processes.
    Type: Grant
    Filed: January 8, 2018
    Date of Patent: July 16, 2019
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Terris Yang, Daniel C. Merkel, Haluk Kopkalli, Gustavo Cerri, Yuon Chiu, Richard D. Horwath
  • Publication number: 20190210944
    Abstract: The present disclosure provides various manufacturing processes for the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf or 1234yf). Such methods may allow for the improved yields, more economical processes, and waste reduction in the production of 1234yf and subsequent processes.
    Type: Application
    Filed: January 8, 2018
    Publication date: July 11, 2019
    Inventors: Haiyou Wang, Terris Yang, Daniel C. Merkel, Haluk Kopkalli, Gustavo Cerri, Yuon Chiu, Richard D. Horwath
  • Publication number: 20190144364
    Abstract: 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: Application
    Filed: June 11, 2018
    Publication date: May 16, 2019
    Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
  • Publication number: 20190084906
    Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, oligomerization/polymerization of such reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that vaporizing such starting reagents in the presence of one or more organic co-feed reduces such oligomerization/polymerization and improves catalytic stability.
    Type: Application
    Filed: November 20, 2018
    Publication date: March 21, 2019
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou WANG, Hsueh Sung TUNG, Selma BEKTESEVIC, Daniel C. MERKEL, Haluk KOPKALLI, Yuon CHIU
  • Patent number: 10131597
    Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, oligomerization/polymerization of such reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that vaporizing such starting reagents in the presence of one or more organic co-feed reduces such oligomerization/polymerization and improves catalytic stability.
    Type: Grant
    Filed: November 2, 2012
    Date of Patent: November 20, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Selma Bektesevic, Daniel C. Merkel, Haluk Kopkalli, Yuon Chiu
  • Publication number: 20180327340
    Abstract: A process for the manufacture of halogenated olefins in semi-batch mode by dehydrohalogenation of halogenated alkanes in the presence of an aqueous base such as KOH which simultaneously neutralizes the resulting hydrogen halide. During the process, aqueous base is continuously added to the haloalkane which results in better yields, lower by-product formation and safer/more controllable operation.
    Type: Application
    Filed: February 5, 2018
    Publication date: November 15, 2018
    Inventors: GEORGE R. COOK, HALUK KOPKALLI, STEPHEN A. COTTRELL, YUON CHIU, PETER SCHEIDLE, DANIEL C. MERKEL
  • Publication number: 20180318788
    Abstract: Disclosed is a process to separate halogenated organic contaminants such as 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2,3,3,3-tetrafluoropropene (HFO-1234yf), trifluoropropyne (TFPY) from hydrochloric acid (HCl) with an adsorbent selected from an activated carbon, an MFI molecular sieve, a carbon molecular sieve, silica, and combinations thereof.
    Type: Application
    Filed: November 4, 2016
    Publication date: November 8, 2018
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Richard Durick HORWATH, Yuon CHIU, Haluk KOPKALLI, Robert A. SMITH, Haiyou WANG, Michael GATTER, Hsueh Sung TUNG, Daniel C. MERKEL
  • Publication number: 20180297917
    Abstract: The invention provides a reactor comprising a reaction chamber having a catalytic surface in contact with reactants in said chamber, and a source for passing electrical current through said catalytic surface. The reactor can be used for dehydrohalogentation reactions, such as dehydrochlorination of HCFC-244bb to HFO-1234yf and for reactions where zero valent metals are employed for catalysis. The invention further provides a process to prepare HFO-1234yf from HCFC-244bb using an electrically heated reaction chamber.
    Type: Application
    Filed: October 14, 2016
    Publication date: October 18, 2018
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk KOPKALLI, Ron Joseph ROOF, Yuon CHIU, Hsueh Sung TUNG, Robert A. SMITH
  • Patent number: 10029964
    Abstract: Azeotropic or azeotrope-like compositions of 3,3,3-trifluoropropyne and water, such as from about 1 to about 50 wt. % water and from about 50 to about 99 wt. % 3,3,3-trifluoropropyne, based on the combined weight of the water and 3,3,3-trifluoropropyne, and methods of producing essentially water free 3,3,3-trifluoropropyne.
    Type: Grant
    Filed: August 30, 2016
    Date of Patent: July 24, 2018
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Hang T. Pham, Daniel C. Merkel
  • Patent number: 9994503
    Abstract: 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: Grant
    Filed: April 4, 2016
    Date of Patent: June 12, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
  • Publication number: 20180057434
    Abstract: Azeotropic or azeotrope-like compositions of 3,3,3-trifluoropropyne and water, such as from about 1 to about 50 wt. % water and from about 50 to about 99 wt. % 3,3,3-trifluoropropyne, based on the combined weight of the water and 3,3,3-trifluoropropyne, and methods of producing essentially water free 3,3,3-trifluoropropyne.
    Type: Application
    Filed: August 30, 2016
    Publication date: March 1, 2018
    Inventors: Haluk Kopkalli, Hang T. Pham, Daniel C. Merkel
  • Patent number: 9890096
    Abstract: Disclosed is a process for the manufacture of 1234yf from 1,1,2,3-tetrachloropropene, abbreviated herein as “TCP,” in three integrated steps: (a) the R-1 hydrofluorination of TCP to form 1233xf in the vapor phase; (b) the R-2 hydrofluorination of 1233xf to form 244bb in either the liquid phase or in the liquid phase followed by the vapor phase; and (c) the R-3 dehydrochlorination of the 244bb in either the liquid or the vapor phase to produce 1234yf; wherein the vapor phase hydrofluorination of TCP in step (a) is carried out at a higher pressure than the liquid phase hydrofluorination of 1233xf; and wherein the HC1 generated during these steps is scrubbed with water to form an acid solution and the organic components are scrubbed with a caustic solution and then dried before further processing.
    Type: Grant
    Filed: December 7, 2011
    Date of Patent: February 13, 2018
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Yuon Chiu, Haluk Kopkalli, Hsueh Sung Tung, Kevin D. Uhrich, Peter Scheidle
  • Patent number: 9884796
    Abstract: A process for the manufacture of halogenated olefins in semi-batch mode by dehydrohalogenation of halogenated alkanes in the presence of an aqueous base such as KOH which simultaneously neutralizes the resulting hydrogen halide. During the process, aqueous base is continuously added to the haloalkane which results in better yields, lower by-product formation and safer/more controllable operation.
    Type: Grant
    Filed: April 16, 2013
    Date of Patent: February 6, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: George R. Cook, Haluk Kopkalli, Stephen A. Cottrell, Yuon Chiu, Peter Scheidle, Daniel C. Merkel
  • Publication number: 20170239638
    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 1,2,3-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: Application
    Filed: May 9, 2017
    Publication date: August 24, 2017
    Applicant: Honeywell International, Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Haiyou Wang, Haluk Kopkalli, Yuon Chiu
  • Patent number: 9676687
    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: April 27, 2016
    Date of Patent: June 13, 2017
    Assignee: HONEYWELL INTERNATIONAL. INC.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Haiyou Wang, Haluk Kopkalli, Yuon Chiu
  • Patent number: 9675950
    Abstract: The present invention is directed to a combination reactor system for exothermic reactions comprising a trickle-bed reactor and a shell-and-tube reactor. This combination allows the system to efficiently remove heat while also providing the ability to control both the temperature and/or reaction progression. The trickle-bed reactor removes heat efficiently from the system by utilizing latent heat and does not require the use of a cooling or heating medium. The shell-and-tube reactor is used to further progress the reaction and provides a heat exchanger in order to introduce fluid at the desired temperature in the shell-and-tube reactor. Also, additional reactant or reactants and/or other fluids may be introduced to the shell-and-tube section of the reactor under controlled temperature conditions.
    Type: Grant
    Filed: January 26, 2015
    Date of Patent: June 13, 2017
    Assignee: Honeywell International Inc.
    Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
  • Publication number: 20160340277
    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: Application
    Filed: March 21, 2016
    Publication date: November 24, 2016
    Inventors: STEPHEN A. COTTRELL, JOHN J. SENETAR, HSUEH S. TUNG, DANIEL C. MERKEL, YUON CHIU, HALUK KOPKALLI
  • Publication number: 20160332934
    Abstract: The invention relates to a composition comprising 2-choro-1,1,1,2-tetrafluoropropane (244bb) and less than about 2% by weight 1,1,1,2,2-pentafluoropropane (245cb).
    Type: Application
    Filed: June 22, 2016
    Publication date: November 17, 2016
    Applicant: Honeywell International, Inc.
    Inventors: Yuon Chiu, Haluk Kopkalli, Robert A. Smith, Daniel C. Merkel
  • Publication number: 20160304421
    Abstract: 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: Application
    Filed: April 4, 2016
    Publication date: October 20, 2016
    Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
  • Patent number: RE46928
    Abstract: Provided are azeotropic and azeotrope-like compositions of 1,2,3,3,3-pentafluoropropene (HFO-1225ye) and water. Such azeotropic and azeotrope-like compositions are useful in isolating 1,2,3,3,3-pentafluoropropene from impurities during production. Azeotropes of the instant invention are similarly useful in final compositions or manufacturing final compositions, such as blowing agent, propellants, refrigerants, diluents for gaseous sterilization and the like.
    Type: Grant
    Filed: February 10, 2017
    Date of Patent: July 3, 2018
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham