Catalyst In Liquid Phase Patents (Class 570/228)
  • Patent number: 11918980
    Abstract: A catalyst for continuous production of 1,1,1,3-tetrachloropropane through gas-solid reaction as well as a preparation method and use thereof are provided. The catalyst includes a zero-valent iron and phosphorus co-modified carbon material which includes a carbon material as a carrier, a zero-valent iron supported onto the carrier and serving as an active component, and a phosphate functional group formed on the surface of the carbon material. The preparation method includes: co-modifying a carbon material using a ferric salt and organic phosphorus to obtain the catalyst for continuous production of 1,1,1,3-tetrachloropropane through gas-solid reaction. The present application further provides a method for continuous production of 1,1,1,3-tetrachloropropane through gas-solid reaction.
    Type: Grant
    Filed: December 24, 2021
    Date of Patent: March 5, 2024
    Assignees: NINGBO INSTITUTE OF MATERIALS TECHNOLOGY & ENGINEERING, CHINESE ACADEMY OF SCIENCES, NINGBO JUHUA CHEMICAL & SCIENCE CO., LTD.
    Inventors: Yexin Zhang, Qiang Zhou, Jian Zhang, Junliang Zhong, Xiuxiu Wang, Jili Du, Hui Chen, Chengjun Mu, Jie Yang, Linbing Xia, Yong Yang, Gang Wu
  • Patent number: 8907147
    Abstract: The present invention provides an improved process for producing 1,1,2,3-tetrachloropropene. By using a first reactive distillation column for HCC-250fb dehydrochlorination, and a second reactive distillation column for HCC-240db dehydrochlorination/HCC-1230xf isomerization, the 1,1,2,3-tetrachloropropene manufacturing process can be greatly simplified, resulting in reduced equipment use, energy use, as well as increased productivity.
    Type: Grant
    Filed: January 30, 2014
    Date of Patent: December 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Joshua Close, Terris Tianxue Yang
  • Patent number: 8877991
    Abstract: This invention relates to a method to improve 1,1,3-trichloropropene selectivity in HCC-250fb (1,1,1,3-tetrachloropropane) dehydrochlorination. In normal practice, FeCl3 is used as the catalyst for the dehydrochlorination of HCC-250fb to produce 1,1,3-trichloropropene. In this invention as source of water is added into the reaction system to inhibit the formation of high boiling compounds such as pentachlorocyclohexene and/or hexachlorocyclohexane. Once source of water is H2O itself. Another source of water is one or more hydrated metal halides.
    Type: Grant
    Filed: February 17, 2014
    Date of Patent: November 4, 2014
    Assignee: Honeywell International Inc.
    Inventors: Terris Yang, Hsueh Sung Tung, Robert Johnson, Joshua Close
  • Patent number: 8779222
    Abstract: A production method of 1,1,3-trichloro-1-propene comprising the following steps A and B; Step A: 1,1,1,3-tetrachloropropane is dehydrochlorinated at a temperature between 30° C. and 50° C. in the presence of at least one base selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, and a phase transfer catalyst, Step B: 3,3,3-trichloro-1-propene obtained in the step A is isomerized into 1,1,3-trichloro-1-propene in the presence of a metal catalyst.
    Type: Grant
    Filed: August 27, 2010
    Date of Patent: July 15, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Souda, Koji Hagiya
  • Patent number: 8779218
    Abstract: Process of catalytic fluorination in liquid phase of product 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane into product 2-chloro-3,3,3-trifluoropropene in presence of a catalyst.
    Type: Grant
    Filed: March 21, 2011
    Date of Patent: July 15, 2014
    Assignee: Arkema France
    Inventors: Anne Pigamo, Laurent Wendlinger, Philippe Bonnet
  • Publication number: 20140100394
    Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of a feedstream comprising 1,2-dichloropropane, a by-product in the production of chlorohydrin, as a low cost starting material, alone or in combination with 1,2,3-trichloropropane. Selectivity of the process is enhanced over conventional processes employing successive chlorinations and/or dehydrochlorinations, by conducting at least one chlorination in the presence of an ionic chlorination catalyst. The present processes may also generate anhydrous HCl as a byproduct that can be removed from the process and used as a feedstock for other processes, providing further time and cost savings.
    Type: Application
    Filed: May 18, 2012
    Publication date: April 10, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES, LLC
    Inventors: Max M. Tirtowidjojo, William J. Kruper, JR., Barry B. Fish, David S. Laitar
  • Patent number: 8258355
    Abstract: Provided is a continuous process for preparing 1,1,2,3-tetrachloro-1-propene having the steps of catalytically dehydrochlorinating CH2ClCCl2CH2Cl in the gas phase to produce CHCl?CClCH2Cl; chlorinating the CHCl?CClCH2Cl to form CHCl2CCl2CH2Cl; and catalytically dehydrochlorinating the CHCl2CCl2CH2Cl in the gas phase to form CCl2?CClCH2Cl.
    Type: Grant
    Filed: July 24, 2008
    Date of Patent: September 4, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung, Michael Van Der Puy, Jing Ji Ma
  • Patent number: 6909024
    Abstract: This invention is a process for producing vinyl chloride from an ethylene-containing feed, oxygen, and a chlorine source in the presence of a catalyst. The process permits direct production of vinyl chloride in a single reactor system, and further permits ethane to be used as the C2 hydrocarbon feed with recycle of ethylene from the product stream to constitute the ethylene specified for the feed. This invention in another aspect concerns also a composition of matter, and a method for making the composition, wherein the composition is useful as a catalyst for the vinyl chloride process. The composition comprises a rare earth-containing material, with the proviso that the catalyst prepared therefrom is substantially free of iron and copper and with the further proviso that when cerium is present the catalyst further comprises at least one more rare earth element other than cerium.
    Type: Grant
    Filed: October 3, 2000
    Date of Patent: June 21, 2005
    Assignee: The Dow Chemical Company
    Inventors: Mark E. Jones, Michael M. Olken, Daniel A. Hickman
  • Patent number: 6797845
    Abstract: A process for producing vinyl chloride monomer where significant quantities of both ethane and ethylene in input streams to the affiliated reactor where hydrogen chloride in the reactor effluent is essentially fully recovered from the reactor effluent in the first unit operation after the ethane/ethylene-to-vinyl reaction step or stage. Steps are presented of oxydehydro-chlorination catalytic reaction of ethane, ethylene, hydrogen chloride, oxygen, and chlorine; quenching the reactor effluent stream to provide a raw product stream having essentially no hydrogen chloride; and separation of the raw product stream into a vinyl chloride monomer product stream and into a lights stream; and recycling the lights steam to the reactor.
    Type: Grant
    Filed: May 14, 2002
    Date of Patent: September 28, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Daniel A. Hickman, John P. Henley, Mark E. Jones, Kenric A. Marshall, Daniel J. Reed, William D. Clarke, Michael M. Olken, Lee E. Walko
  • Patent number: 6388151
    Abstract: A method for synthesizing tetramethylcyclopentadiene from 2,3-dibromobutane is described. A 2-bromo-2-butene Grignard is reacted with an ethyl formate to produce a 3,5-dimethyl-2,5-heptadiene-4-ol magnesium bromide which is then quenched with acetic acid to produce 3,5-dimethyl-2,5-hepadiene-4-ol.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: May 14, 2002
    Assignee: Boulder Scientific Company
    Inventors: Jeffrey M. Sullivan, Richard D. Crawford
  • Patent number: 6380446
    Abstract: Halogenated compounds are dehydrohalogenated in a multi-stage bubble reactor wherein agitation of the reactor contents is provided by in situ generation and vaporization of reaction product having a boiling point lower than that of the reactants.
    Type: Grant
    Filed: March 7, 2001
    Date of Patent: April 30, 2002
    Assignee: DuPont Dow Elastomers, L.L.C.
    Inventors: David William Drew, Terry Wayne Redwine
  • Patent number: 5811605
    Abstract: The dehydrochlorination of 1,1,2,3,3-pentachloropropane to produce 1,2,3,3-tetrachloropropene is conducted using aqueous alkali metal hydroxide in the substantial absence of added ethanol.The 1,2,3,3-tetrachloropropene is recovered from the reaction mixture in the substantial absence of added ether. The preferred methods of recovery are steam distillation and flash distillation.
    Type: Grant
    Filed: February 19, 1997
    Date of Patent: September 22, 1998
    Assignee: PPG Industries, Inc.
    Inventors: Robert H. Tang, G. V. Bindu Madhavan, Yingchao Zhang
  • Patent number: 5763705
    Abstract: There are provided production methods of 1,1,1,3,3-pentafluoropropane characterized in that 1,1,1,3,3-pentafluoro-2,3-dichloropropane is reacted with hydrogen fluoride in the presence of a noble metal catalyst; of 1,1,1,3,3-pentafluoro-2-halogeno-3-chloropropane characterized in that the halogenated propene indicated as general formula I is fluorinated in the presence of antimony trihalogenide and/or antimony pentahalogenide by hydrogen fluoride of mole ratio of or over five times the said antimony halogenide in a liquid phase; and of 1,1,1,2,3,3-hexachloropropene characterized in that 1,1,1,2,2,3,3-heptachloropropane is reacted with an aqueous solution of alkali metal hydroxide in the presence of a phase transfer catalyst. Therefore, an industrial manufacturing method which is possible to obtain the objective product easily at low cost and high yield can be provided.
    Type: Grant
    Filed: March 10, 1997
    Date of Patent: June 9, 1998
    Assignee: Daikin Industries Ltd.
    Inventors: Seiji Takubo, Hirokazu Aoyama, Tatsuo Nakada
  • Patent number: 5648571
    Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.
    Type: Grant
    Filed: March 27, 1996
    Date of Patent: July 15, 1997
    Inventors: Charles J. Rogers, Alfred Kornel
  • Patent number: 5608130
    Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.
    Type: Grant
    Filed: April 22, 1996
    Date of Patent: March 4, 1997
    Inventors: Charles J. Rogers, Alfred Kornel
  • Patent number: 5545388
    Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: August 13, 1996
    Inventors: Charles J. Rogers, Alfred Kornel
  • Patent number: 5478548
    Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: December 26, 1995
    Inventors: Charles J. Rogers, Alfred Kornel
  • Patent number: 5463153
    Abstract: Process for preparing 1-chloro-1,3-butadiene, which consists in gas-phase dehydrochlorinating a dichlorobutene selected from 3,4-dichloro-1-butene and 1,4-dichloro-2-butene, in the presence of a catalyst selected from lanthanum phosphate and lanthanum phosphate doped with an alkali or alkaline-earth metal.
    Type: Grant
    Filed: September 19, 1994
    Date of Patent: October 31, 1995
    Assignee: Enichem Elastomeres France S.A.
    Inventor: Isabelle Storet
  • Patent number: 5396002
    Abstract: The invention concerns a process for producing unsaturated compounds from chlorinated alkanes by dehydrochlorination wherein a phase transfer catalyst is used during reaction of chlorinated alkane with aqueous base. After dehydrochlorination, the products are distilled or flashed off. Then, the phase transfer catalyst is recovered and reused by extracting the catalyst from spent aqueous base with fresh chlorinated alkane and using the mixture of chlorinated alkane and catalyst from the extraction as feedstock.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: March 7, 1995
    Assignee: The Dow Chemical Company
    Inventors: Daniel J. Reed, T. Gayle Snedecor, Jr.
  • Patent number: 5237114
    Abstract: Quaternary ammonium phase transfer catalyst is removed from the dehydrochlorination product of 3,4-dichlorobutene-1 by treatment of the organic, chloroprene-containing phase with an oxy acid which combines with the catalyst to form a separate phase.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: August 17, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Joseph F. Englert, Jr., Willie Harrison, Jr.
  • Patent number: 5210344
    Abstract: In a process for production of vinylidene chloride by dehydrohalogenation of 1,1,2-trichloroethane using a base, improved selectively for formation of vinylidene chloride is obtained by using as the base a cyclic amine having a pK.sub.a greater than about 11 as dehydrohalogenating agent.
    Type: Grant
    Filed: May 27, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: Daniel J. Reed, Tarver G. Snedecor
  • Patent number: 5196617
    Abstract: A process for hydrodehalogenating halogenated organic compounds present in a contaminated aqueous environmental source in which the halogenated organic compounds are reacted with hydrogen gas or a source of hydrogen gas in the presence of a catalyst of palladium on carbon.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: March 23, 1993
    Assignee: Engelhard Corporation
    Inventors: Suphan Kovenklioglu, Edward N. Balko, Jeffrey B. Hoke, Robert J. Farrauto, Gary A. Gramiccioni
  • Patent number: 5151263
    Abstract: A process for the catalytic decomposition of chlorofluoro-alkanes commonly named as "flons" into harmless substances against destructing ozone layer of the stratosphere by using the catalyst comprising alumina or alumina -silica complexed oxide, wherein the range of Al/(Al+Si)atomic ratio is 1.0 to 0.5, in the presence of steam at the temperature of 350.degree. to 1.000.degree. C.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: September 29, 1992
    Assignee: Dupont-Mitsui Fluorochemicals Co., Ltd.
    Inventors: Susumu Okazaki, Akito Kurosaki
  • Patent number: 5107040
    Abstract: A process comprising contacting a solvent, magnesium hydroxide, and a halogenated hydrocarbon at a pressure sufficient to keep the solvent and the halogenated hydrocarbon under liquid conditions, and a temperature greater than 150.degree. C. under conditions suitable to dehydrohalogenate the halogenated hydrocarbon, and recovering the dehydrohalogenated product.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: April 21, 1992
    Assignee: The Dow Chemical Company
    Inventors: Joseph F. Repman, Tarver G. Snedecor, Jr.
  • Patent number: 5099085
    Abstract: The use of hitherto known supported catalysts in chlorination processes and oxychlorination processes leads to high pressure drops and to the formation of hot spot temperatures in the reactor. When honeycomb monolithic catalyst supports provided with a multiplicity of channels open at both ends and parallel to the longitudinal axis are used, both the heat dissipation is improved and the pressure drops across the reactor are lowered drastically. This leads ultimately to an increase in the selectivity of the reaction and to a minimization of the combustion rate.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: March 24, 1992
    Assignees: Wacker Chemie GmbH, Degussa AG
    Inventors: Rudolf Strasser, Ludwig Schmidhammer, Klaus Deller, Helmfried Krause
  • Patent number: 4849561
    Abstract: The liquid phase dehydrochlorination of haloalkanes is performed with an initiator mainly comprising decachlorobutane and/or octachloro-1-butene.The process is applicable, in particular, to the production of chloroethylenes from the corresponding polychloroethanes.
    Type: Grant
    Filed: February 18, 1987
    Date of Patent: July 18, 1989
    Assignee: Solvay & Cie (Societe Anonyme)
    Inventor: James Franklin
  • Patent number: 4816609
    Abstract: An unsaturated halohydrocarbon such as vinylidene chloride is produced by the dehydrohalogenation of haloalkanes such as 1,1,1-trichloroethane or 1,1,2-trichloroethane, in the presence of a novel mixed salt catalyst containing a Group IA metal cation such as Cs, a Group IIA metal cation such as Mg and a neutralizing number of counter anions such as chloride distributed on a support such as silica.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: March 28, 1989
    Assignee: The Dow Chemical Company
    Inventor: A. Dale Harley
  • Patent number: 4650914
    Abstract: A process is disclosed for preparing 1,1,2,3-tetrachloropropene comprising allylic rearrangement of 2,3,3,3-tetrachloropropene using a substantially anhydrous ferric chloride catalyst. Alternatively, 1,1,2,3-tetrachloropropene is prepared by dehydrochlorination of 1,1,1,2,3-pentachloropropane using a ferric chloride catalyst. Process schemes commencing with the preparation of the precursor 1,1,1,3-tetrachloropropane by reaction of ethylene with carbon tetrachloride are also disclosed.
    Type: Grant
    Filed: January 9, 1985
    Date of Patent: March 17, 1987
    Assignee: Monsanto Company
    Inventor: Scott S. Woodard
  • Patent number: 4629816
    Abstract: 2,3-Dichlorobutadiene-(1,3) is obtained from 2,3,4-trichlorobutene-1 by dehydrohalogenation in the presence of a phase transfer catalyst, an inhibitor and oxygen according to an improved process in which the aqueous solution of an alkali metal hydroxide is added to the mixture of trichlorobutene, catalyst, inhibitor and optionally water, and the reaction is carried out at a temperature of from -10.degree. to +60.degree. C. under an inert gas which contains from 0.1 to 8% by weight of oxygen.
    Type: Grant
    Filed: March 1, 1983
    Date of Patent: December 16, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef Heinrich, Rudolf Casper, Manfred Beck
  • Patent number: 4613709
    Abstract: The pyrolytic dehydrochlorination of haloalkanes is carried out with an initiator comprising chiefly decachlorobutane and octachloro-1-butene.The process can be applied particularly to the production of chloroethylenes from the corresponding polychloroethanes.
    Type: Grant
    Filed: August 15, 1985
    Date of Patent: September 23, 1986
    Assignee: Solvay & Cie.
    Inventor: James Franklin
  • Patent number: 4605800
    Abstract: An improved process for the catalytic dehydrochlorination of 3,4-dichlorobutene-1 with aqueous alkali, wherein the effluent from the dehydrochlorination reactor is separated into phases, and the organic phase is steam-stripped at low temperature (below about 80.degree. C.) to recover chloroprene product, while the steam stripper heels are returned to the dehydrochlorination reactor. A small portion of the heels are purged prior to being recycled. Most of the catalyst is recovered and returned to the reaction, but a small amount of make-up catalyst is added. Chloroprene made in this process is a valuable monomer which finds use in the manufacture of a broad line of synthetic elastomers of considerable industrial interest.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: August 12, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Joseph F. Englert, Jr., Louis J. Maurin, III, Clare A. Stewart, Jr.
  • Patent number: 4535194
    Abstract: A process is disclosed for preparing 1,1,2,3-tetrachloropropene comprising allylic rearrangement of 2,3,3,3-tetrachloropropene using a substantially anhydrous ferric chloride catalyst. Alternatively, 1,1,2,3-tetrachloropropene is prepared by dehydrochlorination of 1,1,1,2,3-pentachloropropane using a ferric chloride catalyst. Process schemes commencing with the preparation of the precursor 1,1,1,3-tetrachloropropane by reaction of ethylene with carbon tetrachloride are also disclosed.
    Type: Grant
    Filed: July 6, 1983
    Date of Patent: August 13, 1985
    Assignee: Monsanto Co.
    Inventor: Scott S. Woodard
  • Patent number: 4418232
    Abstract: Improvement in the catalytic dehydrohalogenation of a halogenated hydrocarbon to an ethylenically unsaturated product with aqueous alkali in a series of reactors in a cascade arrangement, wherein the fresh alkali feed is relocated from the first reactor to a reactor subsequent to the first, and partly spent alkali solution from the last reactor is recirculated to the first reactor, while the ethylenically unsaturated product is recovered from the effluent from the last reactor, and waste brine is removed from the effluent from the reactor immediately preceding that to which fresh alkali is fed. In this manner, the amount of both the alkali and the catalyst can be reduced, and the conversion is increased. Dehydrochlorination of 3,4-dichlorobutene-1 gives chloroprene, which is a valuable monomer for making synthetic elastomers.
    Type: Grant
    Filed: November 29, 1982
    Date of Patent: November 29, 1983
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventor: Louis J. Maurin, III
  • Patent number: 4271325
    Abstract: The dehydrohalogenation of a 1,1,1,3-tetrahalo-4-methylpentane to a 1,1-dihalo-4-methyl-1,3-pentadiene is accomplished in the liquid phase in the presence of a catalytic amount of stannic chloride. The diene is a useful intermediate in the manufacture of insecticidal synthetic pyrethroid esters.
    Type: Grant
    Filed: January 9, 1978
    Date of Patent: June 2, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Harold M. Pitt