Isomerization Patents (Class 570/202)
  • Patent number: 11065611
    Abstract: Catalyst regeneration processes that include measures for controlling emissions generated during the regeneration are described. The present invention further relates to catalytic processes for producing various chlorinated aromatic compounds that include provisions for controlling emissions during catalyst regeneration.
    Type: Grant
    Filed: October 5, 2017
    Date of Patent: July 20, 2021
    Assignee: Monsanto Technology LLC
    Inventor: Kam-To Wan
  • Patent number: 10926215
    Abstract: A method of drying a fluid comprising a fluoropropene, which method comprises the step of contacting the fluid with a desiccant comprising a molecular sieve having openings which have a size across their largest dimension of from about 3 ? to about 5 ?. A heat transfer device comprising a heat transfer fluid comprising a fluoropropene, and a desiccant comprising a molecular sieve having openings which have a size across their largest dimension of from about 3 ? to about 5 ?. Preferably, the fluoropropene is R134yf or R-1225ye.
    Type: Grant
    Filed: December 3, 2019
    Date of Patent: February 23, 2021
    Assignee: Mexichem Amaneo Holding S.A. de C.V.
    Inventors: Robert Elliott Low, Stuart Corr
  • Patent number: 9975823
    Abstract: The present invention relates to a process for the preparation of a compound of formula I (I), comprising reacting a compound of formula II (II), with a brominating agent in the presence of an acidic catalyst to a compound of formula III (III), and reacting the compound of formula III in tetrahydrofuran or 2-methyl-tetrahydrofuran with potassium tert-butoxide to a compound of formula I.
    Type: Grant
    Filed: October 8, 2015
    Date of Patent: May 22, 2018
    Assignee: Syngenta Participations AG
    Inventor: Helmars Smits
  • Patent number: 9353029
    Abstract: The invention relates to a process to prepare tetrahalopropenes, such as 2-chloro-3,3,3-trifluoropropene (1233xf). The process comprises atomizing a feed material, such as 1,1,2,3-tetrachloropropene (1230xa) and the like, and mixing it with superheated HF to form a vaporized composition of feed material and HF with substantially instantaneous contact with a vapor phase fluorination catalyst. The invention extends catalyst life and forestalls catalyst deactivation.
    Type: Grant
    Filed: March 12, 2014
    Date of Patent: May 31, 2016
    Assignee: HONEYWELL INTERNATIONAL, INC.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Haiyou Wang, Haluk Kopkalli, Yuon Chiu
  • Patent number: 8420873
    Abstract: The present invention provides a process for producing 2,3,3,3-tetrafluoropropene including the step of dehydrofluorinating 1,1,1,2,3-pentafluoropropane, wherein 1,3,3,3-tetrafluoropropene and 1,1,3,3,3-pentafluoropropane are supplied together with 1,1,1,2,3-pentafluoropropane to a reactor containing a catalyst to simultaneously perform dehydrofluorination reaction and isomerization reaction. According to the process of the present invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be efficiently produced by effectively using the by-products of the dehydrofluorination reaction.
    Type: Grant
    Filed: August 20, 2009
    Date of Patent: April 16, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Kazuhiro Takahashi, Takehiro Chaki, Yuko Shiotani
  • Patent number: 7906694
    Abstract: The present invention relates to a method of preparing mono-iodo benzene with a transiodination reaction, and more preferably a method of preparing mono-iodo benzene including a step of performing transiodination of a reactant including benzene and at least a multi-iodo benzene selected from the group consisting of di-iodo benzene and tri-iodo benzene with an HY or HBeta type of zeolite having a Si/Al molar ratio of 10 to 100 as a catalyst. The method of the present invention has an advantage that iodine is recovered from by-products including m-di-iodo benzene, o-di-iodo benzene, and tri-iodo benzene obtained in the process of preparing p-di-iodo benzene, thereby resulting in minimizing the loss of iodine.
    Type: Grant
    Filed: November 23, 2007
    Date of Patent: March 15, 2011
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Han-Seok Kim, Jong-In Lee, Il-Hoon Cha, Yong-Ki Park, Won-Choon Choi, Bu-Sub Song
  • Patent number: 7268262
    Abstract: Describes a method for recovering trans-1,2-dichloroethene from a liquid feed composition comprising both the cis-and trans-isomers of 1,2-dichloroethene and contaminating amounts of other chlorinated hydrocarbons, e.g., lower alkyl chlorinated hydrocarbons, such as C1-C2 chlorinated hydrocarbons. In one of the described methods, the liquid feed composition is introduced into a first distillation column 10 wherein the stereoisomers and chlorinated hydrocarbons more volatile than the stereoisomers are removed as overhead 12 and charged to a second distillation column 20. In column 20, the stereoisomers are separated from the more volatile chlorinated hydrocarbons, and a bottoms fraction 24 comprising the stereoisomers is charged to a reactive distillation column 30 wherein the cis-isomer is isomerized to the trans-isomer in the liquid phase and in the presence of an organic free-radical initiator, e.g., an azonitrile initiator.
    Type: Grant
    Filed: April 29, 2004
    Date of Patent: September 11, 2007
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Clark S. Graybill, Stephen R. Lester
  • Patent number: 7138554
    Abstract: A method for the synthesis of cyclobuta aromatic compounds by cyclizing two ortho dibromoalkyl substituents is described. Using a mediator, such as nickel metal, and continuous removal of product from contact with the mediator, high product yields are achieved. A method for bromination of ortho alkyl substituents of aromatic compounds is also described.
    Type: Grant
    Filed: June 12, 2002
    Date of Patent: November 21, 2006
    Assignee: Technion Research and Development Foundation
    Inventor: Amnon Stanger
  • Patent number: 6781021
    Abstract: A catalyst composition with a high halogenated aromatics isomerization activity, a halogenated aromatic isomerization method using said catalyst composition, and a halogenated aromatics isomerization method capable of prolonging the life or regeneration period of the catalyst. The invention also includes a catalyst composition characterized in that the maximum diameter of secondary particles of the zeolite in the formed catalyst is 5 microns or less is used to improve the halogenated aromatics isomerization activity. Furthermore, if dissolved oxygen is decreased, the life or regeneration period of the catalyst can be prolonged.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: August 24, 2004
    Assignee: Toray Industries, Inc.
    Inventors: Hajime Kato, Kazuyoshi Iwayama, Masashi Kato, Shinobu Yamakawa, Hirohito Okino
  • Publication number: 20020132723
    Abstract: The present invention provides a catalyst composition with a high halogenated aromatics isomerization activity, a halogenated aromatic isomerization method using said catalyst composition, and a halogenated aromatics isomerization method capable of prolonging the life or regeneration period of the catalyst.
    Type: Application
    Filed: November 8, 2001
    Publication date: September 19, 2002
    Applicant: Toray Industries, Inc.
    Inventors: Hajime Kato, Kazuyoshi Iwayama, Masashi Kato, Shinobu Yamakawa, Hirohito Okino
  • Publication number: 20010012910
    Abstract: Prior to carrying out a gaseous phase chemical reaction, a liquid phase organic compound which is prone to degrade is vaporized at elevated pressures with the aid of a second compound. In one embodiment of the invention, vaporization is effected by co-vaporizing a mixture of the two compounds in a vaporizer. In another embodiment, the first compound is injected into a hot gaseous stream and undergoes atomization into droplets which then vaporize within the gaseous stream. The second compound is used to assist the atomization process and/or to sweep atomized droplets of the first compound away from hot surfaces where the first compound would otherwise tend to undergo degradation if the droplets are allowed to reside in contact with such surfaces.
    Type: Application
    Filed: April 11, 2001
    Publication date: August 9, 2001
    Inventors: John David Scott, Charles Brian Blake, Paul Nicholas Ewing, Jeremy Charles Bauser Hunns, Steven Toplis, Andrew Neil Irwin, Mark Spruce
  • Patent number: 6235952
    Abstract: A method for isomerizing a halogenated ethylbenzene characterized by bringing the same into contact with an acidic zeolite containing at least one metal selected among metals of Groups 7 to 11; and a method of efficiently isolating a m-halogenated ethylbenzene from a mixture of halogenated ethylbenzene isomers by adsorption using a specific zeolite X or Y as the adsorbent. The isomerization method enables a halogenated ethylbenzene to be efficiently isomerized with the zeolite catalyst. The separation method enables m-chloroethylbenzene to be efficiently separated from a mixture of chloroethylbenzene isomers by using a specific zeolite as the adsorbent.
    Type: Grant
    Filed: December 4, 1998
    Date of Patent: May 22, 2001
    Assignee: Toray Industries, Inc.
    Inventors: Eiichi Minomiya, Satoru Miyata
  • Patent number: 5466881
    Abstract: In the preparation of m-chloroaromatics by isomerizing corresponding o- and/or p-chloroaromatics in the liquid phase over zeolites, the activity of the zeolites remains at a high level for a particularly long time if the process is carried out in the presence of from 1 to 30 mol % of hydrogen, based on the chloroaromatics used.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: November 14, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Pies, Helmut Fiege, Lothar Puppe, Josef Kasbauer
  • Patent number: 5180862
    Abstract: A process for isomerizing trichlorobenzene is disclosed. In the process of the present invention, a mixture of trichlorobenzene isomers containing 1,3,5-trichlorobenzene and/or 1,2,3-trichlorobenzene in small concentrations is contacted with a catalyst including acid type mordenite zeolite or acid type beta zeolite and a rhenium component and/or silver component in liquid phase in the presence of hydrogen, thereby increasing concentrations of 1,3,5-trichlorobenzene and/or 1,2,3-trichlorobenzene in said mixture.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: January 19, 1993
    Assignee: Toray Industries, Inc.
    Inventors: Kazuyoshi Iwayama, Hiroaki Honda
  • Patent number: 5159082
    Abstract: A process for producing an aromatic compound is disclosed, which comprises coupling an aromatic sulfinic acid or a salt thereof with an aromatic halogen compound having at least one halogen atom attached to the carbon atom of the aromatic nucleus thereof or a vinyl group-containing halogen compound having at least one halogen atom attached to the carbon atom of said vinyl group in the presence of a catalyst compound containing an element selected from platinum metals.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: October 27, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Toru Okoshi
  • Patent number: 5051536
    Abstract: One stereoisomer of 1,2-dichloroethene is isomerized to the other stereoisomer in the liquid phase and in the presence of free radical initiator.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: September 24, 1991
    Assignee: PPG Industries, Inc.
    Inventors: Earl M. Gorton, John D. Driskill, Randall M. Hall
  • Patent number: 5043493
    Abstract: Process for the preparation of 2-chloro- or 2-bromonaphthalene by isomerizing 1-chloro- or 1-bromonaphthalene over a zeolite as a catalyst which, in the anhydrous and template-free form, has the general formula (A)Z.Al.sub.2 O.sub.3..times.SiO.sub.2 (A)in which Z deontesM.sub.2.sup.I O, M.sup.II O or (M.sup.III).sub.2 O.sub.3,in which M.sup.I represents an alkali metal atom or ammonium or a hydrogen atom, M.sup.II represents an alkaline earth metal atom and M.sup.III represents a rare earth metal of atomic number 57 to 71 in the Periodic Table of the Elements, and x denotes a number from 4 to 4,000, with the proviso that if Z represents M.sub.2.sup.I O, at least some of the alkali metal atoms are replaced by hydrogen atoms, ammonium and/or the other metal atoms mentioned.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: August 27, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: marita Neuber, Ernst I. Leupold
  • Patent number: 4962245
    Abstract: By a process for preparing halogenated benzene derivatives comprising distilling or stripping a mixture of the isomers of a halogenated benzene derivative containing a hydrogen halide to remove the hydrogen halide from the isomeric mixture of the halogenated benzene derivative and then contacting with a zeolite adsorbent for selectivity separating the desired isomer of the halogenated benzene derivative, it is possible to prevent from degrading the zeolite adsorbent. And it is possible to separate selectively industrially an desired isomer of the halogenated benzene derivative for a long time without reduction of productivity and to separate selectively the desired isomer in high purity.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: October 9, 1990
    Assignee: Toray Industries
    Inventors: Takashi Kanai, Michio Kimura, Yoshio Noguchi
  • Patent number: 4935561
    Abstract: The invention relates to a process for isomerizing monochlorotoluenes or dichlorotoluenes on a zirconium-containing zeolite catalyst of the Pentasil type. Catalysts of this type are distinguished by a particularly high activity coupled with a long service life. In particular, the invention relates to the preparation of a mixture 3-chlorotoluene and 4-chlorotoluene by isomerizing 2-chlorotoluene on zircoium-containing zeolite catalysts of the Pentasil type.The invention also relates to the preparation of a mixture of 2,5-dichlorotoluene and 3,4-dichlorotoluene by appropriate isomerization of 2,4-dichlorotoluene, and to the preparation of a mixture of 2,4-dichlorotoluene and 2,5-dichlorotoluene by appropriate isomerization of 3,4-dichlorotoluene.
    Type: Grant
    Filed: May 31, 1985
    Date of Patent: June 19, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus Eichler, Hans-Jurgen Arpe, Herbert Baltes, Ernst I. Leupold
  • Patent number: 4895993
    Abstract: An isomerization of a haloalkene is conducted in the presence of a mixture of a copper compound and a trithiocarbonic acid derivative or dithiocarbonic acid derivative.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: January 23, 1990
    Assignee: Phillips Petroleum Company
    Inventors: H. Wayne Mark, Richard C. Doss, Clarence R. Bresson
  • Patent number: 4861928
    Abstract: By using a catalyst containing an acid type zeolite and at least one component of metal selected from the group consisting of rhenium, nickel and silver and isomerizing a mixture of the isomers of dichlorotoluene in the presence of hydrogen, the concentration of at least one or more components of the isomers of dichlorotoluene can be increased. According to this method, there is provided a process for isomerization of DCT which exhibits a high isomerization capacity not degraded with reaction time.
    Type: Grant
    Filed: February 4, 1988
    Date of Patent: August 29, 1989
    Assignee: Toray Industries, Inc.
    Inventors: Kazuyoshi Iwayama, Yasuhiro Magatani, Kuniyuki Tada
  • Patent number: 4808759
    Abstract: The invention concerns a process for the catalytic trans-halogenation of a poly-iodo-benzene, wherein said poly-iodo-benzene is made to react with benzene and with oxygen, in the presence of a zeolite of the X type or of the Y type, exchanged with an alkali metal, with thallium or with a rare earth and anyway present in a form different from the acidic form.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: February 28, 1989
    Assignee: Montedipe S.p.A.
    Inventor: Giuseppe Paparatto
  • Patent number: 4806698
    Abstract: The invention relates to a process for isomerizing liquid iodoaromatic compounds over an acid catalyst.
    Type: Grant
    Filed: March 25, 1987
    Date of Patent: February 21, 1989
    Assignee: Eastman Kodak Company
    Inventors: Mark Rule, Gerald C. Tustin
  • Patent number: 4806697
    Abstract: The invention relates to a process for isomerizing iodoaromatic compounds over a non-acidic zeolite catalyst in the liquid or gas phase in the presence of a source of iodine.
    Type: Grant
    Filed: March 25, 1987
    Date of Patent: February 21, 1989
    Assignee: Eastman Kodak Company
    Inventors: Mark Rule, Gerald C. Tustin
  • Patent number: 4792641
    Abstract: The invention relates to a process for isomerizing and transiodinating iodoaromatic compounds over a non-acid catalyst.
    Type: Grant
    Filed: March 25, 1987
    Date of Patent: December 20, 1988
    Assignee: Eastman Kodak Company
    Inventors: Mark Rule, Donald W. Lane, Thomas H. Larkins, Gerald C. Tustin
  • Patent number: 4774371
    Abstract: A specific isomer of a trisubstituted benzene is continuously separated from a mixture containing at least two isomers of the trisubstituted benzene by adsorptive separation using a simulated moving bed, wherein a faujasite type zeolite adsorbent is used as the adsorpent and the specific isomer is separated as the extract component in the presence of a substituted benzene compound. The specific isomer to be separated is, for example, 2,6-dichlorotoluene, 3,5-dichlorotoluene and 2-chloro-m-xylene. The substituted benzene compound is preferably a compound represented by the formula: ##STR1## wherein R.sup.1 is H or CH.sub.3, R.sup.2 is H, CH.sub.3 or Cl and R.sup.3 is CH.sub.3 or Cl, with the proviso that the case where R.sup.1 is CH.sub.3, R.sup.2 is Cl and R.sup.3 is Cl is excluded.
    Type: Grant
    Filed: April 3, 1986
    Date of Patent: September 27, 1988
    Assignee: Toray Industries, Inc.
    Inventors: Kishio Miwa, Yukiko Nagaoka, Takehisa Inoue, Kuniyuki Tada
  • Patent number: 4760209
    Abstract: In the preparation of 3,5-dichloro-.alpha.-methylstyrene by isopropylation of an m/p-dichlorobenzene mixture, isomerization of the resulting alkylation mixture, subsequent side chain bromination of the alkylation mixture and dehydrobromination of the resulting bromination mixture, the improvement which comprises reacting an excess of an m/p-dichlorobenzene mixture which contains at least 50% by weight of m-dichlorobenzene with isopropyl halide, isomerizing the resulting alkylation mixture under pressure in the presence of aluminum chloride until thermodynamic equilibrium has been attained, separating off the isomerized alkylation mixture from the unreacted m/p-dichlorobenzene mixture, and recycling the unreacted mixture for further reaction.
    Type: Grant
    Filed: December 11, 1986
    Date of Patent: July 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Erich Wolters, Bernhard Beitzke, Karlfried Wedemeyer, Michael Herzhoff, Karl-Wilhelm Henneke, Guido Steffan, Otto Neuner
  • Patent number: 4727201
    Abstract: 1,2-dichlorobenzene is isomerized to 1,4-dichlorobenzene in the presence of a catalyst comprising (a) at least one of AlCl.sub.3 and AlBr.sub.3 and (b) at least one of iodine, alkaline earth metal halides and sulfates and lanthanide halides. Benzene and/or dichlorobenzene is chlorinated with free chlorine in the presence of a catalyst composition comprising (a) at least one suitable metal halide (preferably AlCl.sub.3, SbCl.sub.5 or FeCl.sub.3) and (b) free iodine and/or at least one organic iodo-compound (preferably methyl iodide or p-iodochlorobenzene), so as to obtain a reaction product comprising 1,4-dichlorobenzene). A preferred catalyst composition comprises (a) at least one of AlCl.sub.3 and AlBr.sub.3, (b) free iodine and (c) at least one of alkaline earth metal halides, alkaline earth metal sulfates and lanthanide halides.
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: February 23, 1988
    Assignee: Phillips Petroleum Company
    Inventor: Raymond L. Cobb
  • Patent number: 4650915
    Abstract: The invention relates to a process for preparing p-chlorotoluene and/or m-chlorotoluene by ring-chlorination of toluene by using the following two pages (a) and (b) when further processing the toluene chlorination product composed of mixed isomers:(a) Isolation of p-chlorotoluene from a mixture of o-, m- and p-chlorotoluene by selective adsorption of p-chlorotoluene onto a mesoporous or macroporous zeolite and subsequent desorption of p-chlorotoluene(b) Treatment of an o-chlorotoluene-rich mixture of isomers with an isomerization catalyst.For the exclusive preparation of p-chlorotoluene first p-chlorotoluene is isolated and removed from the toluene chlorination product in stage (a). The remaining mixed isomers are then treated in stage (b) to increase their content of m- and p-isomers and then returned into stage (a).
    Type: Grant
    Filed: August 9, 1985
    Date of Patent: March 17, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Jurgen Arpe, Heinz Litterer, Norbert Mayer
  • Patent number: 4629815
    Abstract: Polychlorobenzenes are isomerized/rearranged, by reacting (i) at least one tetrachlorobenzene, or at least one tetrachlorobenzene in admixture with at least one trichlorobenzene, pentachlorobenzene and/or hexachlorobenzene, or (ii) pentachlorobenzene, or pentachlorobenzene in admixture with at least one trichlorobenzene and/or hexachlorobenzene, or (iii) hexachlorobenzene, or hexachlorobenzene in admixture with at least one trichlorobenzene and/or dichlorobenzene, with at least one alkali metal amide, or at least one alkali metal alcoholate, or admixture thereof, said reaction being conducted in the presence of an agent which complexes the cation of the amide, alcoholate, or admixture thereof.
    Type: Grant
    Filed: June 23, 1981
    Date of Patent: December 16, 1986
    Assignee: Rhone-Poulenc Industries
    Inventor: Gerard Soula
  • Patent number: 4479022
    Abstract: Bromohalogenobenzenes are isomerized to useful, e.g., pharmaceutical or phytosanitary intermediates, by contacting the same with an alkaline base and a catalyst compound which forms a complex with the cation of said alkaline base.
    Type: Grant
    Filed: April 6, 1982
    Date of Patent: October 23, 1984
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Gerard Soula
  • Patent number: 4409407
    Abstract: 1,3,5-Trichlorobenzene is prepared by the isomerization of other trichlorobenzenes at an elevated temperature after the addition of aluminum trichloride and formic acid.
    Type: Grant
    Filed: August 16, 1982
    Date of Patent: October 11, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerd-Michael Petruck, Paul R. Wambach, deceased
  • Patent number: 4368340
    Abstract: 1,3,5,-Trichlorobenzene is produced by chlorinating 1,3,5-trihalobenzene having 1 to 3 bromine atom and 2 to 0 chlorine atom. The gaseous 1,3,5-halobenzene having 1 to 3 bromine atom and 2 to 0 chlorine atom is brought into contact with chlorine gas at a molar ratio of 0.5 to 3.0 of the stoichiometric amount of chlorine required for said conversion, in a vapor phase at a temperature of 280.degree. to 500.degree. C.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: January 11, 1983
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Itaru Shigehara, Mikio Miyaji
  • Patent number: 4368339
    Abstract: Provided is a process for isomerizing a halogenated toluene using an acid form of zeolite as a catalyst.
    Type: Grant
    Filed: August 5, 1981
    Date of Patent: January 11, 1983
    Assignee: Toray Industries, Incorporated
    Inventors: Kuniyuki Tada, Eiichi Minomiya, Takehisa Inoue
  • Patent number: 4347390
    Abstract: 1-Bromo-3,5-dichlorobenzene is produced in high efficiency by a special isomerization of monobromodichlorobenzene in the presence of an aluminum halide and separating the object product and recycling a residue.1-Bromo-3,5-dichlorobenzene is useful intermediates for various agricultural chemicals, dyes and medicines.
    Type: Grant
    Filed: November 13, 1980
    Date of Patent: August 31, 1982
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Itaru Shigehara, Kuniaki Nagatani, Shigeyuki Nishimura