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: 20160237010
    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: Application
    Filed: April 27, 2016
    Publication date: August 18, 2016
    Applicant: Honeywell International, Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Haiyou Wang, Haluk Kopkalli, Yuon Chiu
  • 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
  • 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: 9328043
    Abstract: The present invention relates, in part, an improved process for the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf). In certain non-limiting embodiments, the invention relates to methods for improving process efficiency during the fluorination of 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, and/or 1,1,1,2,3-pentachloropropane to 2-chloro-3,3,3-trifluoropropene by separating and recycling unreacted HF, unreacted starting materials, and/or certain process intermediates from the 2-chloro-3,3,3-trifluoropropene product stream.
    Type: Grant
    Filed: February 25, 2013
    Date of Patent: May 3, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Selma Bektesevic, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu
  • Patent number: 9309175
    Abstract: The invention relates to the use of a liquid-vapor separator such as a de-entrainer to remove an unvaporized portion of a feed, e.g. 1,1,2,3-tetrachloropropene (1230xa), to a catalytic vapor phase fluorination reaction where e.g. 2-chloro-3,3,3,-trifluoropropene (1233xf) is produced. The invention extends the life of the catalyst.
    Type: Grant
    Filed: April 18, 2014
    Date of Patent: April 12, 2016
    Assignee: Honeywell International Inc.
    Inventors: Selma Bektesevic, Haluk Kopkalli, Haiyou Wang
  • Patent number: 9302963
    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 9, 2012
    Date of Patent: April 5, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
  • Patent number: 9296669
    Abstract: Disclosed is a process for passivating a surface of a dehydrochlorination reactor comprising: stopping a flow of hydrochlorofluoropropane to a reactor, passing a gas mixture comprising hydrogen gas through the reactor at a temperature of at least 25° C. for a period of time sufficient to restore the selectivity of a dehydrochlorination reaction, stopping the flow of the hydrogen gas mixture, and resuming the flow of hydrochlorofluoropropane to the dehydrochlorination reaction.
    Type: Grant
    Filed: January 8, 2013
    Date of Patent: March 29, 2016
    Assignee: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Xuehui Sun, Mario Joseph Nappa, Haiyou Wang, Haluk Kopkalli
  • Patent number: 9296670
    Abstract: A method for forming 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprising providing a dehydrochlorination starting material having relatively low concentrations of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), especially and preferable less than about 8.0% when the dehydrochlorination reaction utilizes no substantial amount of catalyst or catalyst comprising austenitic nickel-based materials.
    Type: Grant
    Filed: February 8, 2013
    Date of Patent: March 29, 2016
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Haiyou Wang, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu, Gustavo Cerri, Jeffrey Ball, Philip L. Da Prato, Xuehui Sun, Mario Joseph Nappa
  • 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: 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
  • Publication number: 20160052842
    Abstract: This disclosure relates to processes which involve: contacting a mixture comprising at least one fluoroolefin and at least one RfC?CX impurity with at least one zeolite to reduce the concentration of the at least one RfC?CX impurity in the mixture; wherein Rf is a straight-chain perfluorinated alkyl group, and X is H, F, Cl, Br or I; and the at least one zeolite is selected from the group consisting of zeolites having pore opening of at least 4 Angstroms and no more than about 5 Angstroms, zeolites having pore opening of at least about 5 Angstroms and Sanderson electronegativity of no more than about 2.6, and mixtures thereof; provided that the at least one zeolite is not zeolite 4A.
    Type: Application
    Filed: November 4, 2015
    Publication date: February 25, 2016
    Applicant: THE CHEMOURS COMPANY FC, LLC
    Inventors: Mario Joseph NAPPA, Xuehui SUN, David Richard CORBIN, Haluk KOPKALLI, Haiyou WANG
  • 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
  • Publication number: 20150259267
    Abstract: This disclosure relates to processes which involve: contacting a mixture comprising at least one fluoroolefin and at least one RfC?CX impurity with at least one zeolite to reduce the concentration of the at least one RfC?CX impurity in the mixture; wherein Rf is a straight-chain perfluorinated alkyl group, and X is H, F, Cl, Br or I; and the at least one zeolite is selected from the group consisting of zeolites having pore opening of at least 4 Angstroms and no more than about 5 Angstroms, zeolites having pore opening of at least about 5 Angstroms and Sanderson electronegativity of no more than about 2.6, and mixtures thereof; provided that the at least one zeolite is not zeolite 4A.
    Type: Application
    Filed: March 14, 2014
    Publication date: September 17, 2015
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Xuehui SUN, David Richard CORBIN, Haluk KOPKALLI, Haiyou WANG
  • Patent number: 9126888
    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: Grant
    Filed: June 9, 2014
    Date of Patent: September 8, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
  • 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: 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
  • Publication number: 20150139869
    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: January 26, 2015
    Publication date: May 21, 2015
    Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath