Patents Examined by Medhanit Bahta
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Patent number: 9416075Abstract: 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: GrantFiled: July 16, 2014Date of Patent: August 16, 2016Assignee: ZEON CORPORATIONInventor: Tatsuya Sugimoto
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Patent number: 9399609Abstract: 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: GrantFiled: March 11, 2014Date of Patent: July 26, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Daniel C. Merkel, Hsueh Sung Tung, Haluk Kopkalli
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Patent number: 9399739Abstract: 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: GrantFiled: June 13, 2014Date of Patent: July 26, 2016Assignee: SYNGAG TECHNOLOGY LLCInventors: Duane A Goetsch, Christian T Goralski, Jr., Jacqueline R Hitchingham
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Patent number: 9388102Abstract: 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: GrantFiled: December 15, 2011Date of Patent: July 12, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Kun Wang, Roberto Garcia, Jihad M. Dakka, Edmund J. Mozeleski
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Patent number: 9388099Abstract: 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: GrantFiled: April 24, 2015Date of Patent: July 12, 2016Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
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Patent number: 9371259Abstract: 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: GrantFiled: July 12, 2012Date of Patent: June 21, 2016Assignees: SHANGHAI ADVANCED RESEARCH INSTITUTE, CHINESE ACADEMY OF SCIENCES, ZHONGKE YIGONG (SHANGHAI) CHEMICAL TECHNOLOGY CO., LTD.Inventors: Biao Jiang, Jinguang Zhong
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Patent number: 9371346Abstract: 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: GrantFiled: June 13, 2011Date of Patent: June 21, 2016Assignee: INVISTA North America S.a.r.l.Inventor: John J. Ostermaier
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Patent number: 9370768Abstract: 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: GrantFiled: October 2, 2015Date of Patent: June 21, 2016Assignee: Chevron U.S.A. Inc.Inventor: Kandaswamy Jothimurugesan
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Patent number: 9365472Abstract: 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: GrantFiled: December 26, 2014Date of Patent: June 14, 2016Assignee: CENTRAL GLASS COMPANY, LTD.Inventors: Satoru Okamoto, Naoto Takada, Fuyuhiko Sakyu, Takamasa Kitamoto, Takuya Tonomura, Masatomi Kanai
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Patent number: 9353028Abstract: 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 occurrenceType: GrantFiled: February 10, 2015Date of Patent: May 31, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Barry Asher Mahler, Hsueh Sung Tung, Mario Joseph Nappa
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Patent number: 9346723Abstract: 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: GrantFiled: January 11, 2013Date of Patent: May 24, 2016Assignee: Arkema FranceInventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
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Patent number: 9340473Abstract: 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: GrantFiled: January 21, 2011Date of Patent: May 17, 2016Assignee: Arkema FranceInventors: Anne Pigamo, Nicolas Doucet, Laurent Wendlinger
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Patent number: 9334208Abstract: 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: GrantFiled: December 14, 2011Date of Patent: May 10, 2016Assignee: Arkema FranceInventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
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Patent number: 9334454Abstract: 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: GrantFiled: April 15, 2011Date of Patent: May 10, 2016Assignee: SICHUAN YALIAN TECHNOLOGY CO., TDLInventors: Yaling Zhong, Yuming Zhong, Qiming Zeng, Yueming Cai, Tianhong Chen
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Patent number: 9334206Abstract: 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: GrantFiled: March 11, 2014Date of Patent: May 10, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Selma Bektesevic, Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
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Patent number: 9321708Abstract: 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: GrantFiled: January 24, 2013Date of Patent: April 26, 2016Assignee: Central Glass Company, LimitedInventors: Hideaki Imura, Naoto Takada, Masamune Okamoto
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Patent number: 9315431Abstract: 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: GrantFiled: October 8, 2014Date of Patent: April 19, 2016Assignee: ARKEMA FRANCEInventor: Anne Pigamo
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Patent number: 9309176Abstract: 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: GrantFiled: March 19, 2015Date of Patent: April 12, 2016Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew P. Sharratt, Claire E. McGuinness, John Hayes
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Patent number: 9308513Abstract: 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: GrantFiled: June 11, 2013Date of Patent: April 12, 2016Assignee: UOP LLCInventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
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Patent number: 9309175Abstract: 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: GrantFiled: April 18, 2014Date of Patent: April 12, 2016Assignee: Honeywell International Inc.Inventors: Selma Bektesevic, Haluk Kopkalli, Haiyou Wang