Patents Represented by Attorney Bruce Bradford
  • Patent number: 8178466
    Abstract: The present disclosure provides methods for pre-treating activated carbon before it is used in a dehydrochlorination process. The methods can comprise mixing the activated carbon with an acid, an oxidizing agent in a liquid phase, or an oxidizing agent in a gas phase. Activated carbons undergoing one or more of these methods can exhibit improved stability during the dehydrochlorination process.
    Type: Grant
    Filed: January 14, 2011
    Date of Patent: May 15, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh S. Tung
  • Patent number: 8168837
    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: May 12, 2009
    Date of Patent: May 1, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Patent number: 8158549
    Abstract: A support of metal oxyfluoride or metal halide for a metal-based hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.
    Type: Grant
    Filed: September 4, 2009
    Date of Patent: April 17, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8119845
    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: September 13, 2010
    Date of Patent: February 21, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 8119557
    Abstract: There is provided methods for making a catalyst composition represented by the formula MX/M?F2 wherein MX is an alkali metal halide; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?; M?F2 is a bivalent metal fluoride; and M? is a bivalent metal ion. There is also a method for making a fluorinated olefin.
    Type: Grant
    Filed: November 21, 2008
    Date of Patent: February 21, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8114308
    Abstract: Provided are azeotropic and azeotrope-like compositions of 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf) 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: Grant
    Filed: March 30, 2010
    Date of Patent: February 14, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hang T. Pham, Ryan Hulse, Rajiv R. Singh, Konstantin A. Pokrovski, Hsueh S. Tung
  • Patent number: 8084653
    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 (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl?CH2, preferably in a 80-96% selectivity. The CF3CCl?CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. 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.
    Type: Grant
    Filed: January 3, 2007
    Date of Patent: December 27, 2011
    Assignee: Honeywell International, Inc.
    Inventors: Hsueh S. Tung, Sudip Mukhopadhyay, Michael Van Der Puy, Daniel C. Merkel, Jing Ji Ma, Cheryl L. Bortz, Barbara A. Light, Steven D. Phillips, Rajesh K. Dubey
  • Patent number: 8075797
    Abstract: The invention is directed to a ternary azeotrope-like mixture consisting essentially of effective amounts of 1,1,1,3,3-pentafluoropropane, 1-chloro-3,3,3-trifluoropropene, and hydrogen fluoride.
    Type: Grant
    Filed: January 25, 2010
    Date of Patent: December 13, 2011
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Rajiv R. Singh, Hsueh S. Tung, Ian Shankland
  • Patent number: 8070975
    Abstract: Provided are azeotropic and azeotrope-like compositions of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) 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: Grant
    Filed: February 10, 2009
    Date of Patent: December 6, 2011
    Assignee: Honeywell International Inc.
    Inventors: Hang T. Pham, Rajiv R. Singh, HsuehSung Tung, Konstantin A. Pokrovski, Daniel C. Merkel
  • Patent number: 8071825
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ??(II) where Z is H, F, Cl, I or Br.
    Type: Grant
    Filed: August 1, 2008
    Date of Patent: December 6, 2011
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
  • Patent number: 8071826
    Abstract: A process for the preparation of 2,3,3,3-tetrafluoropropene (HFO-1234yf). HFO-1234yf is a refrigerant with low global warming potential. A process comprises a) reacting chlorotrifluoroethylene with a methyl halide to form an intermediate product stream; and b) reacting the intermediate product stream with hydrogen fluoride to thereby produce a result comprising 2,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: February 24, 2009
    Date of Patent: December 6, 2011
    Assignee: Honeywell International Inc.
    Inventor: Michael Van Der Puy
  • 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
  • Patent number: 8063257
    Abstract: A method for preparing 2,3,3,3-tetrafluoropropene comprising contacting a reactant comprising CCl2?CFCH2Cl with a fluorinating agent, such as HF, under conditions effective to produce a reaction product comprising CF3CF?CH2.
    Type: Grant
    Filed: August 15, 2008
    Date of Patent: November 22, 2011
    Assignee: Honeywell International Inc.
    Inventors: Jing Ji Ma, Michael Van Der Puy
  • Patent number: 8058486
    Abstract: A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX2?CCl—CH2X??(Formula I) CX3—CCl?CH2??(Formula II) CX3—CHCl—CH2X??(Formula III) wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.
    Type: Grant
    Filed: March 13, 2009
    Date of Patent: November 15, 2011
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Selma Bektesevic, Robert C. Johnson, Haiyou Wang
  • Patent number: 8053612
    Abstract: A process for making a fluorinated olefin. The process has the step of dehydrochlorinating a hydrochlorofluorocarbon having at least one hydrogen atom and at least one chlorine atom on adjacent carbon atoms in the presence of a catalytically effective amount of a catalyst composition. The catalyst composition is represented by the following: n wt. % MX/M?OyFz, wherein 0<y<1 and 0<z<2 and wherein y+z/2=1; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?, M? is a bivalent metal ion; wherein n is a weight percentage of about 0.05% to about 50% MX based on the total weight of the MX and M?OyFz, and wherein y and z are the mole fractions of oxygen and fluorine in M?OyFz, respectively. There are also methods for making catalyst compositions.
    Type: Grant
    Filed: May 27, 2009
    Date of Patent: November 8, 2011
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8044250
    Abstract: A process for producing hydrofluorocarbon compounds represented by the following formula: CF3CHFCHm+1Fn wherein m is 0 or 2; n is 0 or 2; and m+n=2. The process has the step of contacting, i.e., reacting, hydrogen with a precursor compound represented by the following formula: CF3CF?CHmFn wherein m is 0 or 2; n is 0 or 2; and m+n=2. The contact is carried out in the presence of a solid catalyst and in the presence or absence of an inert gas. The catalyst is selected from the group consisting of: Fe, Co, Ni, Cu, Cr, Ru, Rh, Ag, Re, Os, Ir, Pt, Au, Sn, and any combinations thereof. For the hydrogenation of 1234yf to 254eb, Pd can also be used as catalyst in addition to the other above-referenced metals. These metals are preferably supported on a carrier such as activated carbon.
    Type: Grant
    Filed: November 4, 2008
    Date of Patent: October 25, 2011
    Assignee: Honeywell International Inc.
    Inventors: Shuwu Yang, Hsueh Sung Tung
  • Patent number: 8034251
    Abstract: Provided are ternary azeotropic and azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), 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: Grant
    Filed: March 18, 2009
    Date of Patent: October 11, 2011
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsuehsung Tung, Hang T. Pham, Rajiv R. Singh
  • Patent number: 8034984
    Abstract: Dehydrohalogenation processes for the preparation of fluoropropenes from corresponding halopropanes, in which the fluoropropenes have the formula CF3CY?CXNHP, wherein X and Y are independently hydrogen or a halogen selected from fluorine, chlorine, bromine and iodine; and N and P are independently integers equal to 0, 1 or 2, provided that (N+P)=2.
    Type: Grant
    Filed: September 22, 2010
    Date of Patent: October 11, 2011
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh S. Tung
  • 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
  • Patent number: 8008243
    Abstract: An azeotrope-like composition consisting essentially of 1,1,2,3-tetrachloropropene and hydrogen fluoride is provided, as well as methods that involve such an azeotrope-like composition.
    Type: Grant
    Filed: October 28, 2009
    Date of Patent: August 30, 2011
    Assignee: Honeywell International Inc.
    Inventors: Hsueh S. Tung, Hang T. Pham, Rajiv R. Singh, Daniel C. Merkel, Robert Johnson