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: 8969634
    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: September 26, 2011
    Date of Patent: March 3, 2015
    Assignee: Honeywell International Inc.
    Inventors: Yuon Chiu, Haluk Kopkalli, Richard Durick Horwath
  • Publication number: 20150057472
    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: Application
    Filed: April 18, 2014
    Publication date: February 26, 2015
    Applicant: Honeywell International Inc.
    Inventors: Selma Bektesevic, Haluk Kopkalli, Haiyou Wang
  • Patent number: 8951431
    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: April 8, 2011
    Date of Patent: February 10, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
  • 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
  • Publication number: 20150011804
    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 pro cess intermediates from the 2-chloro-3,3,3-trifluoropropene product stream.
    Type: Application
    Filed: February 25, 2013
    Publication date: January 8, 2015
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Selma Bektesevic, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu
  • Publication number: 20150005536
    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: Application
    Filed: February 8, 2013
    Publication date: January 1, 2015
    Applicant: HONEYWELL INTERNATIONAL, INC.
    Inventors: Haiyou Wang, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu, Gustavo Cerri, Jeffrey Ball, Philip L. Da Prato, Xuehui Sun, Mario Joseph Nappa
  • Publication number: 20140364657
    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: Application
    Filed: January 8, 2013
    Publication date: December 11, 2014
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Xuehui Sun, Mario Joseph Nappa, Haiyou Wang, Haluk Kopkalli
  • Publication number: 20140343331
    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: Application
    Filed: March 13, 2014
    Publication date: November 20, 2014
    Applicant: HONEWELL INTERNATIONAL, INC.
    Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
  • Patent number: 8859829
    Abstract: The present invention relates in part to a method of stabilizing 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: March 11, 2014
    Date of Patent: October 14, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Haiyou Wang, Hsueh Sung Tung, Daniel C. Merkel
  • Publication number: 20140284517
    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: June 9, 2014
    Publication date: September 25, 2014
    Inventors: RYAN HULSE, HALUK KOPKALLI, HANG T. PHAM
  • Publication number: 20140275646
    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: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou WANG, Daniel C. MERKEL, Hsueh Sung TUNG, Haluk KOPKALLI
  • Publication number: 20140275645
    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 14, 2013
    Publication date: September 18, 2014
    Inventors: STEPHEN A. COTTRELL, JOHN J. SENETAR, HSUEH S. TUNG, DANIEL C. MERKEL, YUON CHIU, HALUK KOPKALLI
  • Publication number: 20140275662
    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: Application
    Filed: March 14, 2013
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk Kopkalli, Jeffrey A. Ball, Yuon Chiu, Hsueh Sung Tung, Konstantin A. Pokrovski, Daniel C. Merkel
  • Publication number: 20140275650
    Abstract: The present invention relates in part to a method of stabilizing 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: March 11, 2014
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haluk KOPKALLI, Haiyou WANG, Hsueh SUNG TUNG, Daniel C. MERKEL
  • Publication number: 20140275647
    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: March 12, 2014
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL, INC.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Haiyou Wang, Haluk Kopkalli, Yuon Chiu
  • Publication number: 20140275648
    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: Application
    Filed: March 12, 2014
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL, INC.
    Inventors: Yuon Chiu, Haluk Kopkalli, Robert A. Smith, Daniel C. Merkel
  • Patent number: 8747691
    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: April 8, 2011
    Date of Patent: June 10, 2014
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
  • Patent number: 8710282
    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: Grant
    Filed: September 9, 2011
    Date of Patent: April 29, 2014
    Assignee: Honeywell International Inc.
    Inventors: Selma Bektesevic, Hsueh Sung Tung, Haluk Kopkalli
  • Patent number: 8618340
    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: Grant
    Filed: November 3, 2009
    Date of Patent: December 31, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Kevin Uhrich
  • Patent number: 8496892
    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: Grant
    Filed: January 31, 2012
    Date of Patent: July 30, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Orlando George Rodrigues, Gus Cerri, Hsueh Sung Tung, Stephen A. Cottrell