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).

  • Publication number: 20130079563
    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: Application
    Filed: September 26, 2011
    Publication date: March 28, 2013
    Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
  • Publication number: 20120301373
    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: August 9, 2012
    Publication date: November 29, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: YUON CHIU, STEPHEN A. COTTRELL, HSUEH SUNG TUNG, HALUK KOPKALLI, GUSTAVO CERRI
  • Patent number: 8242316
    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: August 1, 2011
    Date of Patent: August 14, 2012
    Assignee: Honeywell International Inc.
    Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
  • Publication number: 20120184785
    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 lower pressure than the liquid phase hydrofluorination of 123xf; and wherein the HCl 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: Application
    Filed: December 7, 2011
    Publication date: July 19, 2012
    Inventors: Stephen A. Cottrell, Yuon Chiu, Haluk Kopkalli, Hsueh Sung Tung, Kevin D. Uhrich, Peter Scheidle
  • Publication number: 20120134892
    Abstract: Disclosed is a process and apparatus for the catalytic hydrogenation of fluoro-olefins to fluorocarbons where the reaction is carried out in a multi-tube shell and tube reactor. Reactions involving hydrogenation of fluoro-olefins are typically exothermic. In commercial processes where a fluoro-olefin CnH2n-xFx to CnH2n-x2Fx is hydrogenated (e.g., hexafluoropropylene to 236ea, 1225ye to 245eb, and the like), inadequate management or control of heat removal may induce excess hydrogenation, decomposition and hot spots resulting in reduced yields and potential safety issues. In the hydrogenation of fluoro-olefins, it is therefore necessary to control the reaction temperature as precisely as practical to overcome challenges associated with heat management and safety.
    Type: Application
    Filed: January 31, 2012
    Publication date: May 31, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk Kopkalli, Yuon Chiu, Orlando George Rodrigues, Gus Cerri, Hsueh Sung Harry Tung, Stephen A. Cottrell
  • Patent number: 8129574
    Abstract: Disclosed is a process and apparatus for the catalytic hydrogenation of fluoroolefins to fluorocarbons where the reaction is carried out in a multi-tube shell and tube reactor. Reactions involving hydrogenation of fluoro-olefins are typically exothermic. In commercial processes where a fluoro-olefin C(n)H(2n?x)F(x) to C(n)H(2n?x+2)F(x) is hydrogenated (e.g. hexafluoropropylene to 236ea, 1225ye to 245eb, and the like), inadequate management or control of heat removal may induce excess hydrogenation, decomposition and hot spots resulting in reduced yields and potential safety issues. In the hydrogenation of fluoro-olefins, it is therefore necessary to control the reaction temperature as precisely as practical to overcome challenges associated with heat management and safety.
    Type: Grant
    Filed: August 31, 2009
    Date of Patent: March 6, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Orlando George Rodrigues, Gus Cerri, Hsueh Sung Tung, Stephen A. Cottrell
  • Publication number: 20120022302
    Abstract: The instant invention relates, at least in part, to a method increasing the cost efficiency for dehydrohalogenation production of a fluorinated olefin by recovering and recycling spent dehydrohalogenation agent. In one aspect, the present invention relates to dehydrohalogenating a fluorinated alkane (e.g. pentafluoropropane and/or hexafluoropropane) in the presence of a dehydrohalogenating agent to produce a fluorinated olefin (e.g. tetrafluoropropenes and/or pentafluoropropenes). Removal of spent dehydrohalogenating agent from the reactor allows for facile separation of organic and dehydrohalogenating agent, the latter of which is recycled.
    Type: Application
    Filed: September 9, 2011
    Publication date: January 26, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: SELMA BEKTESEVIC, HSUEH SUNG TUNG, HALUK KOPKALLI
  • Patent number: 8067649
    Abstract: Disclosed is a process for producing tetrafluoropropene comprising: (a) catalytically fluorinating at least one tetrafluoropropene in a first reactor to produce HCFO-1233xf; (b) reacting said HCFO-1233xf with hydrogen fluoride in a second reactor to produce HCFC-244bb; (c) recycling at least a portion of said HCFC-244bb back to said first reactor as recycled HCFC-244bb; and (d) catalytically dehydrochlorinating said recycled HCFC-244bb in said first reactor to produce HFO-1234yf.
    Type: Grant
    Filed: May 14, 2009
    Date of Patent: November 29, 2011
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Hsueh Sung Tung
  • Publication number: 20110288347
    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: August 1, 2011
    Publication date: November 24, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: YUON CHIU, STEPHEN A. COTTRELL, HSUEH SUNG TUNG, HALUK KOPKALLI, GUSTAVO CERRI
  • Publication number: 20110275723
    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: Application
    Filed: April 8, 2011
    Publication date: November 10, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
  • Publication number: 20110275724
    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: Application
    Filed: April 8, 2011
    Publication date: November 10, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
  • Publication number: 20110269999
    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: April 29, 2010
    Publication date: November 3, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: George R. Cook, Haluk Kopkalli, Stephen A. Cottrell, Yuon Chiu, Peter Scheidle, Daniel C. Merkel
  • Patent number: 8034308
    Abstract: A multi-stage, multi-tube, shell-and-tube reactor which contains reaction zones and interstage temperature control (cooling/heating) zones in series. The reactor has at least two types of zones which both contribute to removing or supplying heat to the system depending on the system's need. The reactor will have a group of reaction zones which contain tubes packed with catalyst to progress the reaction and remove or supply heat simultaneously. There are also a number of interstage temperature control (cooling/heating) zones which are designed to supply or remove heat to or from the system. The positioning, number, and design of the zones will depend on the amount of temperature control desired and exothermic or endothermic nature of the processes to be conducted in the reactor.
    Type: Grant
    Filed: June 9, 2009
    Date of Patent: October 11, 2011
    Assignee: Honeywell International, Inc.
    Inventors: Yuon Chiu, Stephen A. Cottrell, Richard Durick Horwath, Haluk Kopkalli
  • Patent number: 8013194
    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: March 11, 2009
    Date of Patent: September 6, 2011
    Assignee: Honeywell International Inc.
    Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
  • Publication number: 20110207974
    Abstract: Disclosed is a process for producing tetrafluoropropene comprising: (a) catalytically fluorinating at least one tetrafluoropropene in a first reactor to produce HCFO-1233xf; (b) reacting said HCFO-1233xf with hydrogen fluoride in a second reactor to produce HCFC-244bb; (c) recycling at least a portion of said HCFC-244bb back to said first reactor as recycled HCFC-244bb; and (d) catalytically dehydrochlorinating said recycled HCFC-244bb in said first reactor to produce HFO-1234yf.
    Type: Application
    Filed: May 14, 2009
    Publication date: August 25, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk Kopkalli, Yuon Chiu, Hsueh Sung Tung
  • Publication number: 20110105807
    Abstract: Disclosed is a process for the manufacture of HFO-1234yf from TCP in three integrated steps that include hydrofluorination of TCP (tetrachloropropene) to HCFC-1233xf in the vapor phase followed by hydrofluorination of HCFC-1233xf to HCFC-244bb in the liquid phase which is then followed by dehydrochlorination in liquid or vapor phase to produce HFO-1234yf. The vapor phase hydrofluorination is carried out at a higher pressure than the liquid phase hydrofluorination, thereby eliminating the need for compression and/or intermediate recovery. Also, any HCl generated from this reaction is fed to the liquid phase hydrofluorination section to promote agitation and mixing. This results in a more economical process from an initial capital and operating cost versus conducting the 3-steps sequentially.
    Type: Application
    Filed: November 3, 2009
    Publication date: May 5, 2011
    Applicant: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Kevin D. Uhrich
  • Publication number: 20110054226
    Abstract: Disclosed is a process and apparatus for the catalytic hydrogenation of fluoroolefins to fluorocarbons where the reaction is carried out in a multi-tube shell and tube reactor. Reactions involving hydrogenation of fluoro-olefins are typically exothermic. In commercial processes where a fluoro-olefin C(n)H(2n?x)F(x) to C(n)H(2n?x|2)F(x) is hydrogenated (e.g. hexafluoropropylene to 236ea, 1225ye to 245eb, and the like), inadequate management or control of heat removal may induce excess hydrogenation, decomposition and hot spots resulting in reduced yields and potential safety issues. In the hydrogenation of fluoro-olefins, it is therefore necessary to control the reaction temperature as precisely as practical to overcome challenges associated with heat management and safety.
    Type: Application
    Filed: August 31, 2009
    Publication date: March 3, 2011
    Inventors: Haluk Kopkalli, Yuon Chiu, Orlando George Rodrigues, Gus Cerri, Hsueh Sung Tung, Stephen A. Cottrell
  • Publication number: 20100324345
    Abstract: Systems and processes relating to the formation and production of CFO-1113 HCFC-123a. Such systems and processes can include one or more reactors in series that react HCFC-123a and base to produce reaction product vapors including CFO-1113. Optionally, a phase transfer agent or catalyst can be added to the reaction to enhance the reaction rate. The CFO-1113 can be separated from the reaction product vapors to produce a CFO-1113 product stream. The reactions can be conducted continuously, and a liquid effluent stream can be removed from the reactors during the reaction. Unreacted HCFC-123a can be separated from the liquid effluent stream and provided back to the reactors.
    Type: Application
    Filed: June 22, 2009
    Publication date: December 23, 2010
    Applicant: Honeywell International Inc.
    Inventors: Selma Bektesevic, Hsueh Sung Harry Tung, Haluk Kopkalli
  • Publication number: 20100307726
    Abstract: A multi-stage, multi-tube, shell-and-tube reactor which contains reaction zones and interstage temperature control (cooling/heating) zones in series. The reactor has at least two types of zones which both contribute to removing or supplying heat to the system depending on the system's need. The reactor will have a group of reaction zones which contain tubes packed with catalyst to progress the reaction and remove or supply heat simultaneously. There are also a number of interstage temperature control (cooling/heating) zones which are designed to supply or remove heat to or from the system. The positioning, number, and design of the zones will depend on the amount of temperature control desired and exothermic or endothermic nature of the processes to be conducted in the reactor.
    Type: Application
    Filed: June 9, 2009
    Publication date: December 9, 2010
    Applicant: Honeywell International Inc.
    Inventors: Yuon Chiu, Stephen A. Cottrell, Richard Durick Horwath, Haluk Kopkalli
  • Publication number: 20100119460
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 2,3,3,3-tetrafluoropropene (1234yf) and 3,3,3-trifluoropropene (1243zf), as well as methods for producing and using the same.
    Type: Application
    Filed: November 9, 2009
    Publication date: May 13, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HANG T. PHAM, RAJIV R. SINGH, HSUEH S. TUNG, DANIEL C. MERKEL, HALUK KOPKALLI, RYAN HULSE