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).

  • Patent number: 10005704
    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 the presence of a fluorination catalyst, where by using 2-chloro-3,3,3, -trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Grant
    Filed: January 26, 2015
    Date of Patent: June 26, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert C. Johnson, Daniel C. Merkel
  • Patent number: 10000431
    Abstract: A process for enhancing the selective and efficient production of (E)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E), or 1233zd(E)). During the manufacture of HCFO-1233zd(E) by fluorination of 1,1,1,3,3-pentachloropropane (HCC-240fa), a by-product of 1,1,3,3-tetrachloro-1-fluoropropane (HCFC-241fa) is separated and then dehydrochlorinated to form 1,3,3-trichloro-3-fluoropropene (HCFO-1231zd). The HCFO-1231zd is then fluorinated to form HCFO-1233zd(E).
    Type: Grant
    Filed: January 30, 2018
    Date of Patent: June 19, 2018
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung
  • Patent number: 9994502
    Abstract: A process for enhancing the selective and efficient production of (E)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E), or 1233zd(E)). During the manufacture of HCFO-1233zd(E) by fluorination of 1,1,1,3,3-pentachloropropane (HCC-240fa), a by-product of 1,3,3-trichloro-1,1-difluoropropane (HCFC-242fa) is separated and then dehydrochlorinated to form 1,3-chloro-3,3-difluoropropene (HCFO-1232zd). The HCFO-1232zd is then fluorinated to form HCFO-1233zd(E).
    Type: Grant
    Filed: January 30, 2018
    Date of Patent: June 12, 2018
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung
  • Patent number: 9994504
    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: Grant
    Filed: May 5, 2017
    Date of Patent: June 12, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9950973
    Abstract: Azeotropic or azeotrope-like mixtures of 1,3-dichloro-3,3-difluoroprop-1-ene (HCFO-1232zd) and hydrogen fluoride (HF). Such compositions are useful as a feed stock or intermediate in the production of 1,1,1,3,3-pentafluoropropane (HFC-245fa),1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), and 1,3,3,3-tetrafluoropropene (HFO-1234ze).
    Type: Grant
    Filed: August 31, 2016
    Date of Patent: April 24, 2018
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Haiyou Wang, Ryan J. Hulse, Hang T. Pham
  • Patent number: 9950974
    Abstract: Azeotropic or azeotrope-like mixtures of 1,3,3-trichloro-3-fluoroprop-1-ene (HCFO-1231zd) and hydrogen fluoride (HF). Such compositions are useful as a feed stock or intermediate in the production of 1,1,1,3,3-pentafluoropropane (HFC-245fa), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), and 1,3,3,3-tetrafluoropropene (HFO-1234ze).
    Type: Grant
    Filed: August 31, 2016
    Date of Patent: April 24, 2018
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Haiyou Wang, Ryan J. Hulse, Hang T. Pham
  • Patent number: 9938212
    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 starting feed material or a mixture of unsaturated hydrochlorocarbon feed materials comprising 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloropropene. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E) 1-chloro-3,3,3-trifluoro-propene (1233zd (E)) from these feed materials, which may also include 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.
    Type: Grant
    Filed: March 28, 2012
    Date of Patent: April 10, 2018
    Assignee: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 9914680
    Abstract: Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl3, SbCl5, SbF5, TiCl4, SnCl4, Cr2O3, and fluorinated Cr2O3.
    Type: Grant
    Filed: May 5, 2015
    Date of Patent: March 13, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
  • Publication number: 20180057433
    Abstract: Azeotropic or azeotrope-like mixtures of 1,3,3-trichloro-3-fluoroprop-1-ene (HCFO-1231zd) and hydrogen fluoride (HF). Such compositions are useful as a feed stock or intermediate in the production of 1,1,1,3,3-pentafluoropropane (HFC-245fa),1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), and 1,3,3,3-tetrafluoropropene (HFO-1234ze).
    Type: Application
    Filed: August 31, 2016
    Publication date: March 1, 2018
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Haiyou Wang, Ryan J. Hulse, Hang T. Pham
  • Publication number: 20180057430
    Abstract: Azeotropic or azeotrope-like mixtures of 1,3-dichloro-3,3-difluoroprop-1-ene (HCFO-1232zd) and hydrogen fluoride (HF). Such compositions are useful as a feed stock or intermediate in the production of 1,1,1,3,3-pentafluoropropane (HFC-245fa), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), and 1,3,3,3-tetrafluoropropene (HFO-1234ze).
    Type: Application
    Filed: August 31, 2016
    Publication date: March 1, 2018
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Haiyou Wang, Ryan J. Hulse, Hang T. Pham
  • 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
  • Publication number: 20180056210
    Abstract: A method for separating halocarbons and, in particular, a method for separating (Z)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(Z), or simply 1233zd(Z)) and 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa, or simply 244fa) via distillation by adding a third component, hydrogen fluoride (HF), forming a binary azeotrope of 1233zd(Z) and HF. The binary 1233zd(Z)/HF azeotrope may then be recovered from the distillation column as an overhead stream which includes only a relatively minor amount of 244fa, while the 244fa may be recovered from the distillation column as a bottoms stream which includes only relatively minor amounts of 1233zd(Z) and HF.
    Type: Application
    Filed: August 28, 2017
    Publication date: March 1, 2018
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Rajat S. Basu, Hsueh Sung Tung
  • Patent number: 9902671
    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: Grant
    Filed: January 10, 2017
    Date of Patent: February 27, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • 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: 20180008956
    Abstract: The invention provides for a method of regenerating a solid adsorbent, such as a molecular sieve or activated carbon, using stable fluorinated hydrocarbon compounds such as, for example, HFC-245cb (1,1,1,2,2-pentafluoropropane, as a regeneration fluid.
    Type: Application
    Filed: July 20, 2017
    Publication date: January 11, 2018
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou WANG, Hsueh Sung Tung, Daniel C. Merkel
  • Publication number: 20170313639
    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: July 20, 2017
    Publication date: November 2, 2017
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou WANG, Selma BEKTESEVIC, Daniel C. MERKEL, Hsueh SUNG TUNG, Konstantin A. POKROVSKI
  • Patent number: 9758450
    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: April 8, 2016
    Date of Patent: September 12, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Selma Bektesevic, Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Publication number: 20170253544
    Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, particularly, 1,1,2,3-tetrachloropropene (1230xa), oligomerization/polyinerization of such starting reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that providing one or more organic co-feed to the fluooolefin starting stream reduces such oligomerization/polymerization and improves catalystic stability.
    Type: Application
    Filed: March 21, 2017
    Publication date: September 7, 2017
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Selma BEKTESEVIC, Daniel C. MERKEL, Mario Joseph NAPPA, Xuehui SUN, Hsueh Sung TUNG, Haiyou WANG
  • Publication number: 20170253545
    Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefm starting reagents, particularly, 1,1,2,3-tetrachloropropene (1230xa), oligomerization/polymerization of such starting reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that providing one or more organic co-feed to the fluooolefin starting stream reduces such oligomerization/polymerization and improves catalystic stability.
    Type: Application
    Filed: March 21, 2017
    Publication date: September 7, 2017
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Selma BEKTESEVIC, Daniel C. MERKEL, Mario Joseph NAPPA, Xuehui SUN, Hsueh Sung TUNG, Haiyou WANG
  • Publication number: 20170247304
    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: May 5, 2017
    Publication date: August 31, 2017
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung