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: 8796493
    Abstract: The present invention provides a method for separating halocarbons. In particular, the invention provides a method for separating halogenated olefin impurities from 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) using a solid adsorbent, particularly activated carbon. More particularly the invention pertains to a method for separating 2-chloro-3,3,3-trifluoro-propene (HCFO-1233xf) from HCFC-244bb, which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: September 30, 2011
    Date of Patent: August 5, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Publication number: 20140206910
    Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system including one or more reactors for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.
    Type: Application
    Filed: March 4, 2014
    Publication date: July 24, 2014
    Applicant: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung
  • Patent number: 8784763
    Abstract: Processes and systems for the production of phosphorus pentafluoride (PF5) through continuous fluorination of phosphorus are provided herein. A phosphorus feed stream and a fluorine feed stream are provided to a reactor, wherein they are reacted in a gas-gas or liquid-gas reaction to produce phosphorus pentafluoride (PF5). The phosphorus feed can be derived from white phosphorus or yellow phosphorus, and can be provided to the reactor as a liquid or a vapor. The fluorine can be provided to the reactor as a vapor, and preferably comprises elemental fluorine gas.
    Type: Grant
    Filed: March 11, 2010
    Date of Patent: July 22, 2014
    Assignee: Honeywell International Inc.
    Inventors: Matthew H. Luly, Robert A. Smith, Haridasan K. Nair, Philip DePrato, Konstantin A. Pokrovski, Daniel C. Merkel, Kevin Uhrich, Stephen A. Cottrell, Daniel J. Brenner
  • Publication number: 20140186230
    Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.
    Type: Application
    Filed: March 4, 2014
    Publication date: July 3, 2014
    Applicant: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung
  • Patent number: 8754271
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2?CClCH2Cl is fluorinated to synthesize a compound such as CF3CCl?CH2. The CF3CCl?CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl?CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.
    Type: Grant
    Filed: November 22, 2011
    Date of Patent: June 17, 2014
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Hsueh S. Tung, Michael Van Der Puy, Daniel C. Merkel, Jing Ji Ma, Cheryl L. Bortz, Barbara A. Light, Steven D. Phillips, Rajesh K. Dubey
  • Patent number: 8741828
    Abstract: The present invention pertains to ternary azeotrope and azeotrope-like composition including 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), HF, and either 1,1,2,3-tetrachloropropene (TCP) or 1,1,1,2,2-pentafluoropropane (HFC-245cb). The present invention also relates to binary azeotropes of 2,3,3,3-tetrachloropropene and HF. Such azeotropic and azeotrope-like compositions are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: January 23, 2012
    Date of Patent: June 3, 2014
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham, Hsueh Sung Tung, Konstantin Pokrovski, Daniel C. Merkel
  • Publication number: 20140147343
    Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.
    Type: Application
    Filed: January 30, 2014
    Publication date: May 29, 2014
    Applicant: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
  • Patent number: 8716538
    Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.
    Type: Grant
    Filed: August 2, 2013
    Date of Patent: May 6, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung
  • Patent number: 8704017
    Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.
    Type: Grant
    Filed: August 29, 2011
    Date of Patent: April 22, 2014
    Assignee: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung
  • Publication number: 20140100393
    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: Application
    Filed: June 28, 2010
    Publication date: April 10, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert C. Johnson, Daniel C. Merkel
  • Patent number: 8680345
    Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.
    Type: Grant
    Filed: December 7, 2011
    Date of Patent: March 25, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
  • Patent number: 8664455
    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 a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Grant
    Filed: July 30, 2009
    Date of Patent: March 4, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
  • Patent number: 8664456
    Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd (E)), trans-1,3,3,3-tetrafluoropropene (1234ze (E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloropropene with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd (E) and 244fa (plus by-product HCl); an optionally (2) the 244fa stream can then be used to directly produce any (or all) of the following desired products; (a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze (E); and/or (b) the 244fa stream can be dehydrofluorinated to produce 1233zd (E) if more of that product is desired; and/or (c) the 244fa stream can be further fluorinated to form 245fa.
    Type: Grant
    Filed: March 28, 2012
    Date of Patent: March 4, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Patent number: 8653311
    Abstract: The present invention relates to an azeotropic or azeotrope-like mixture consisting essentially of 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and hydrogen fluoride.
    Type: Grant
    Filed: April 11, 2013
    Date of Patent: February 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung, Daniel C. Merkel, Konstantin A. Pokrovski
  • Patent number: 8648221
    Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd(E)), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 240fa with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd(E) and 244fa (plus byproduct HCl); (2) the 244fa stream can then be used to directly produce any of the three desired products; (3a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze(E); and/or (3b) the 244fa stream can be dehydrofluorinated to produce 1233zd(E) if more of that product is desired; and/or (3c) the 244fa stream can be further fluorinated to form 245fa.
    Type: Grant
    Filed: December 9, 2011
    Date of Patent: February 11, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Haiyou Wang, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • Publication number: 20140012052
    Abstract: Provided are azeotropic and azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) and hydrogen fluoride (HF). Such azeotropic and azeotrope-like compositions are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Application
    Filed: September 10, 2013
    Publication date: January 9, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HANG T. PHAM, DANIEL C. MERKEL, KONSTANTIN A. POKROVSKI, HSUEH S. TUNG, RAJIV R. SINGH
  • Publication number: 20140012047
    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 a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Application
    Filed: September 9, 2013
    Publication date: January 9, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: DANIEL C. MERKEL, STEPHEN A. COTTRELL, ROBERT C. JOHNSON
  • Publication number: 20130338408
    Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.
    Type: Application
    Filed: August 2, 2013
    Publication date: December 19, 2013
    Applicant: Honeywell International Inc.
    Inventors: DANIEL C. MERKEL, KONSTANTIN A. POKROVSKI, HSUEH S. TUNG
  • Publication number: 20130261354
    Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd (E)), trans-1,3,3,3-tetrafluoropropene (1234ze (E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloropropene with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd (E) and 244fa (plus by-product HCl); an optionally (2) the 244fa stream can then be used to directly produce any (or all) of the following desired products; (a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze (E); and/or (b) the 244fa stream can be dehydrofluorinated to produce 1233zd (E) if more of that product is desired; and/or (c) the 244fa stream can be further fluorinated to form 245fa.
    Type: Application
    Filed: March 28, 2012
    Publication date: October 3, 2013
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Publication number: 20130261353
    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 hydrochloro-carbon feed materials comprising 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloro-propene. 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-tetrafluoro-propene (1234ze (E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst.
    Type: Application
    Filed: March 28, 2012
    Publication date: October 3, 2013
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung