Patents Examined by Medhanit Bahta
  • Patent number: 9416075
    Abstract: The present invention is a method for 2-fluorobutane to obtain highly purified 2-fluorobutane through a process comprising a step for: bringing crude 2-fluorobutane that includes 5 to 50 wt % of butene into contact with a brominating agent that can form a bromonium ion in an aprotic polar solvent in the presence of water or an alcohol having up to 4 carbon atoms; converting the butene into compounds having a boiling point higher than that of 2-fluorobutane, then recovering 2-fluorbutane from the reaction solution; and purifying the recovered 2-fluorabutane by distillation.
    Type: Grant
    Filed: July 16, 2014
    Date of Patent: August 16, 2016
    Assignee: ZEON CORPORATION
    Inventor: Tatsuya Sugimoto
  • 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: 9399739
    Abstract: A process for producing distillate fuels, such as a diesel fuel, from a syngas feedstream having a relatively low H2/CO ratio of greater than 1 and equal to or less than 2.0. The syngas feedstream is preferably passed to a CO2 removal zone, then to at least one Fischer-Tropsch zone, wherein the resulting Fischer-Tropsch product stream is passed to a separation zone to obtain a hydrocarbon-containing fraction that is hydroconverted to result in a distillate boiling range stream.
    Type: Grant
    Filed: June 13, 2014
    Date of Patent: July 26, 2016
    Assignee: SYNGAG TECHNOLOGY LLC
    Inventors: Duane A Goetsch, Christian T Goralski, Jr., Jacqueline R Hitchingham
  • Patent number: 9388102
    Abstract: In a process for producing phenol, cyclohexylbenzene is contacted with an oxygen-containing compound in the presence of an oxidation catalyst comprising a cyclic imide under oxidation conditions effective to produce a product comprising cyclohexylbenzene hydroperoxide and unreacted cyclic imide catalyst. Without removing all the unreacted cyclic imide catalyst, at least a portion of the product is contacted with an acidic molecular sieve under conditions effective to adsorb at least a portion of the unreacted cyclic imide and to convert at least part of the cyclohexylbenzene hydroperoxide in the product portion into phenol and cyclohexanone.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: July 12, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, Roberto Garcia, Jihad M. Dakka, Edmund J. Mozeleski
  • Patent number: 9388099
    Abstract: This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl?CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.
    Type: Grant
    Filed: April 24, 2015
    Date of Patent: July 12, 2016
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
  • Patent number: 9371259
    Abstract: Provided is a method for preparing vinyl chloride with acetylene and dichlorethane for large-scale industrial production. Acetylene, dichlorethane vapor and hydrogen chloride gas at a molar ratio of 1:(0.3-1.0):(0-0.20) are mixed; the raw mixed gas is preheated; the preheated raw mixed gas passes through a reactor containing a catalyst and reacts; the resultant mixed gas is cooled to 30-50° C. and pressurized to 0.4-1.0 MPa, and then cooled to ambient temperature, and further frozen to ?25-15° C. for liquefaction isolation, and unliquefied gas is recycled and reused; liquefied liquid is sent to a rectifying tower for rectification, and vinyl chloride monomers meeting polymerization requirements are obtained. The present invention has the advantages of eliminating mercury contamination completely, simplifying the reactor structure, recycling hydrogen chloride and acetylene, reducing waterwash process, avoiding mass production of waste acid and improving utilization of chlorine.
    Type: Grant
    Filed: July 12, 2012
    Date of Patent: June 21, 2016
    Assignees: SHANGHAI ADVANCED RESEARCH INSTITUTE, CHINESE ACADEMY OF SCIENCES, ZHONGKE YIGONG (SHANGHAI) CHEMICAL TECHNOLOGY CO., LTD.
    Inventors: Biao Jiang, Jinguang Zhong
  • Patent number: 9371346
    Abstract: The present invention relates to a method of preparing a nickel complex including nickel and at least one phosphorus-containing ligand by reacting at least a portion of a nickel metal with at least one phosphorus-containing ligand. The nickel metal is prepared from a nickel composition including nickel(II).
    Type: Grant
    Filed: June 13, 2011
    Date of Patent: June 21, 2016
    Assignee: INVISTA North America S.a.r.l.
    Inventor: John J. Ostermaier
  • Patent number: 9370768
    Abstract: A process has been developed for preparing a Fischer-Tropsch catalyst precursor and a Fischer-Tropsch catalyst made from the precursor. The process includes contacting a gamma alumina catalyst support material with a first solution containing a vanadium compound and a phosphorus compound, to obtain a modified catalyst support material. The modified catalyst support material is calcined at a temperature of at least 500° C. The modified catalyst support is less soluble in acid solutions than an equivalent unmodified catalyst support. The modified catalyst support loses no more than 6% of its pore volume when exposed to water vapor. The modified catalyst support is contacted with a second solution which includes a precursor compound of an active cobalt catalyst component to obtain a catalyst precursor. The Fischer-Tropsch catalyst has enhanced hydrothermal stability as measured by losing no more than 10% of its pore volume when exposed to water vapor.
    Type: Grant
    Filed: October 2, 2015
    Date of Patent: June 21, 2016
    Assignee: Chevron U.S.A. Inc.
    Inventor: Kandaswamy Jothimurugesan
  • Patent number: 9365472
    Abstract: A method for producing 1234Z from 1234E while generation of 245fa as a byproduct is suppressed. The method for producing cis-1,3,3,3-tetrafluoropropene includes putting trans-1,3,3,3-tetrafluoropropene into contact with a catalyst. The trans-1,3,3,3-tetrafluoropropene is put into contact with the catalyst at a reaction temperature of higher than or equal to 200° C. and lower than or equal to 550° C. for a contact time of longer than or equal to 0.01 seconds and shorter than or equal to 500 seconds.
    Type: Grant
    Filed: December 26, 2014
    Date of Patent: June 14, 2016
    Assignee: CENTRAL GLASS COMPANY, LTD.
    Inventors: Satoru Okamoto, Naoto Takada, Fuyuhiko Sakyu, Takamasa Kitamoto, Takuya Tonomura, Masatomi Kanai
  • Patent number: 9353028
    Abstract: The present invention relates to a hydrofluorinating process which comprises reacting a fluoroolefin with hydrogen fluoride in the liquid phase in the presence of a hydrofluorination catalyst in the reaction zone of a reactor, said reactor comprised of a reactor body having a length to diameter ratio of about 2:1 or greater; a stirred reaction zone containing said hydrofluorination catalyst, which may be prepared in situ, at least one inlet for supplying said hydrogen fluoride and fluoroolefin to the reaction zone and at least one outlet for recovering said fluoroalkane, said stirrer disposed in the reaction zone and comprising a plurality of blades fixedly attached to shaft drivable by a motor, said blades extending from about the bottom of the reaction zone to about the top of the reaction zone and said shaft extending on a longitudinal axis from the bottom of the reactor to the top of the reactor, said stirrer being rotated at a speed sufficient to promote a swirling of the liquid to effect the occurrence
    Type: Grant
    Filed: February 10, 2015
    Date of Patent: May 31, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Barry Asher Mahler, Hsueh Sung Tung, Mario Joseph Nappa
  • Patent number: 9346723
    Abstract: The invention concerns a method for producing 2,3,3,3-tetrafluoropropene comprising: a fluoridation reaction of a halopropane and/or halopropene into 2,3,3,3-tetrafluoropropene by means of hydrogen fluoride; the recovery of a gas stream resulting from the reaction; the cooling and partial condensation of the gas stream resulting from the reaction into a partially condensed stream; the separation of the partially condensed stream into a gas fraction and a liquid fraction; the compression of the gas fraction into a compressed gas fraction; the compression of the liquid fraction into a compressed liquid fraction; the distillation of the compressed gas fraction and compressed liquid fraction in order to provide a stream of 2,3,3,3-tetrafluoropropene, a stream of hydrochloric acid, and a stream of unreacted hydrogen fluoride. The invention also concerns an installation suitable for implementing said method.
    Type: Grant
    Filed: January 11, 2013
    Date of Patent: May 24, 2016
    Assignee: Arkema France
    Inventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
  • Patent number: 9340473
    Abstract: The present invention relates to a fluorination process, comprising: an activation stage comprising contacting a fluorination catalyst with an oxidizing agent-containing gas flow for at least one hour; and at least one reaction stage comprising reacting a chlorinated compound with hydrogen fluoride in gas phase in the presence of the fluorination catalyst, so as to produce a fluorinated compound.
    Type: Grant
    Filed: January 21, 2011
    Date of Patent: May 17, 2016
    Assignee: Arkema France
    Inventors: Anne Pigamo, Nicolas Doucet, Laurent Wendlinger
  • Patent number: 9334208
    Abstract: The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene from 1,1,1,2,3-pentachloropropane and/or 1,1,2,2,3-pentachloropropane, comprising the following steps: (a) catalytic reaction of 1,1,1,2,3-pentachloropropane and/or 1,1,2,2,3-pentachloropropane with HF into a reaction mixture comprising HCl, 2-chloro-3,3,3-trifluoropropene, 2,3,3,3-tetrafluoropropene, unreacted HF, and optionally 1,1,1,2,2-pentafluoropropane; (b) separating the reaction mixture into a first stream comprising HCl and 2,3,3,3-tetrafluoropropene and a second stream comprising HF, 2-chloro-3,3,3-trifluoropropene and optionally 1,1,1,2,2-pentafluoropropane; (c) catalytic reaction of the second stream into a reaction mixture comprising 2,3,3,3-tetrafluoropropene, HCl, unreacted 2-chloro-3,3,3-trifluoropropene, unreacted HF and optionally 1,1,1,2,2-pentafluoropropane and (d) feeding the reaction mixture of step (c) directly without separation to step (a).
    Type: Grant
    Filed: December 14, 2011
    Date of Patent: May 10, 2016
    Assignee: Arkema France
    Inventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
  • Patent number: 9334454
    Abstract: A method for producing synthesis natural gas using a straw gas, includes the steps of: pressurizing and heating a conventional straw gas, conveying the straw gas to a converter containing carbon monoxide and hydrogen to react therewith in the presence of nickel-based catalyst, so as to result in conversion gas mixture with main components of methane, carbon dioxide, water and impurity; and cooling, gas-liquid separating and purifying to obtain a synthesis natural gas with methane content of over 90%. The synthesis natural gas obtained according to the method of present invention has high energy utilization efficiency, and can not only be used for civilian by a conventional natural gas infrastructure, but also serve as an energy supply for a combustion engine or a small gas turbine.
    Type: Grant
    Filed: April 15, 2011
    Date of Patent: May 10, 2016
    Assignee: SICHUAN YALIAN TECHNOLOGY CO., TDL
    Inventors: Yaling Zhong, Yuming Zhong, Qiming Zeng, Yueming Cai, Tianhong Chen
  • Patent number: 9334206
    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: March 11, 2014
    Date of Patent: May 10, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Selma Bektesevic, Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 9321708
    Abstract: Provided is a purification method for efficiently reducing an undesirable organic compound or compound in (E)-1-chloro-3,3,3-trifluoropropene and thereby obtaining (E)-1-chloro-3,3,3-trifluoropropene with high purity. The purification method of OF-1233E according to the present invention is characterized by bringing a composition containing OF-1233E and at least one organic compound selected from the group consisting of HCFC-142 isomers, HCFC-244fa, HFC-245fa, OF-1234E, OF-1234Z and OF-1233Z into contact with a solid adsorbent.
    Type: Grant
    Filed: January 24, 2013
    Date of Patent: April 26, 2016
    Assignee: Central Glass Company, Limited
    Inventors: Hideaki Imura, Naoto Takada, Masamune Okamoto
  • Patent number: 9315431
    Abstract: The present invention provides a process of fluorination in liquid phase in a solvent medium of a compound of formula (II) CX1X2=CZCX3X4X5, in which Z represents H, Cl or F, and each X1 represents independently hydrogen or chlorine, given that at least one of the X1 represents a chlorine.
    Type: Grant
    Filed: October 8, 2014
    Date of Patent: April 19, 2016
    Assignee: ARKEMA FRANCE
    Inventor: Anne Pigamo
  • Patent number: 9309176
    Abstract: The invention relates to a process for removing one or more undesired (hydro)halocarbon compounds from a (hydro)fluoroalkene, the process comprising contacting a composition comprising the (hydro)fluoroalkene and one or more undesired (hydro)halocarbon compounds with an aluminum-containing absorbent, activated carbon, or a mixture thereof.
    Type: Grant
    Filed: March 19, 2015
    Date of Patent: April 12, 2016
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew P. Sharratt, Claire E. McGuinness, John Hayes
  • Patent number: 9308513
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes processing the acetylene to form a hydrocarbon stream having vinyl chloride. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream is be treated to convert acetylene to other hydrocarbon processes. The method according to certain aspects includes controlling the level of carbon monoxide in the hydrocarbon stream to limit downstream side reactions in the downstream processing units.
    Type: Grant
    Filed: June 11, 2013
    Date of Patent: April 12, 2016
    Assignee: UOP LLC
    Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
  • 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