Dehalogenation Or Dehydrogenation Patents (Class 570/230)
  • Patent number: 9139497
    Abstract: The preparation of chlorinated hydrocarbons by reacting a chlorinated alkane substrate, such as 1,1,1,3-tetrachloropropane, with a source of chlorine, such as chlorine (Cl2), in the presence of a polyvalent bismuth compound, such as triphenyl bismuth and/or triphenyl bismuth dichloride, is described. With the method of the present invention, the chlorinated alkane product has covalently bonded thereto at least one more chlorine group than the chlorinated alkane substrate, and the chlorinated alkane substrate and the chlorinated alkane product each have a carbon backbone structure that is in each case the same.
    Type: Grant
    Filed: September 26, 2014
    Date of Patent: September 22, 2015
    Assignee: AXIALL OHIO, INC.
    Inventor: Scott A. Sherwood
  • Patent number: 9040760
    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: October 27, 2011
    Date of Patent: May 26, 2015
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
  • Patent number: 9018428
    Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 28, 2015
    Assignee: Honeywell International Inc.
    Inventor: Stephen A. Cottrell
  • Publication number: 20150045591
    Abstract: The preparation of chlorinated hydrocarbons, such as pentachloropropanes, such as 1,1,1,2,3-pentachloropropane, from tetrachloropropanes, such as 1,1,1,3-tetrachloropropane, in the presence of a polyvalent antimony compound that includes a pentavalent antimony compound, such as antimony pentachloride, is described. Also described are methods for preparing optionally chlorinated alkenes, such as, tetrachloropropenes, from chlorinated alkanes, such as pentachloropropanes, in the presence of polyvalent antimony compound that includes a pentavalent antimony compound, as well as methods for recovering polyvalent antimony compounds from such processes.
    Type: Application
    Filed: October 22, 2014
    Publication date: February 12, 2015
    Inventors: Scott A. Sherwood, Stephen Robert Lester
  • Patent number: 8921622
    Abstract: A process for the selective dehydrofluorination of hydrochlorofluoroalkanes and novel hydrochlorofluoroalkenes is described wherein an effective amount of a catalytically active metal compound is applied which is selected from the group consisting of AlF3??, MgAlxF2+3x?? and MgZryF2+4y??, wherein x and y have, independently of one another, values in the range of from 0 to 0.33 and ? has a value in the range of from 0 to 0.1. Certain hydrofluorochloroalkenes are also described, as well as their use as intermediates in chemical reactions.
    Type: Grant
    Filed: March 31, 2011
    Date of Patent: December 30, 2014
    Assignee: Solvay SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Publication number: 20140371494
    Abstract: Processes for the production of chlorinated propanes and propenes are provided. The present processes comprise catalyzing at least one chlorination step with one or more regios elective catalysts that provide a regioselectivity to one chloropropane of at least 5:1 relative to other chloropropanes.
    Type: Application
    Filed: December 12, 2012
    Publication date: December 18, 2014
    Inventors: Max Markus Tirtowidjojo, Matthew Lee Grandbois, William J. Kruper, JR., Edward M. Calverley, David Stephen Laitar, Kurt Frederick Hirksekorn
  • Patent number: 8889930
    Abstract: The preparation of chlorinated hydrocarbons, such as pentachloropropanes, such as 1,1,1,2,3-pentachloropropane, from tetrachloropropanes, such as 1,1,1,3-tetrachloropropane, in the presence of a polyvalent antimony compound that includes a pentavalent antimony compound, such as antimony pentachloride, is described. Also described are methods for preparing optionally chlorinated alkenes, such as, tetrachloropropenes, from chlorinated alkanes, such as pentachloropropanes, in the presence of ferric chloride and a polyvalent antimony compound that includes a pentavalent antimony compound.
    Type: Grant
    Filed: October 23, 2013
    Date of Patent: November 18, 2014
    Assignee: Axiall Ohio, Inc.
    Inventors: Scott A. Sherwood, Stephen Robert Lester
  • Publication number: 20140228601
    Abstract: Processes for isolating 1,1,1,2,3-pentachloropropane from a crude product stream containing the 1,1,1,2,3-pentachloropropane and ferric chloride. The processes may include deep distillation of the crude, treatment of the crude with a reagent that deactivates the ferric chloride followed by distillation on the deactivated crude stream, aqueous washing of the crude product stream to remove ferric chloride followed by distillation on the deactivated crude stream. Other embodiments simultaneously prepare 1,1,2,3-tetrachloroprene and 1,1,1,2,3-pentachloroprane.
    Type: Application
    Filed: March 14, 2013
    Publication date: August 14, 2014
    Inventor: Occidental Chemical Corporation
  • Publication number: 20140206911
    Abstract: The preparation of chlorinated hydrocarbons, such as pentachloropropanes, such as 1,1,1,2,3-pentachloropropane, from tetrachloropropanes, such as 1,1,1,3-tetrachloropropane, in the presence of a polyvalent antimony compound that includes a pentavalent antimony compound, such as antimony pentachloride, is described. Also described are methods for preparing optionally chlorinated alkenes, such as, tetrachloropropenes, from chlorinated alkanes, such as pentachloropropanes, in the presence of ferric chloride and a polyvalent antimony compound that includes a pentavalent antimony compound.
    Type: Application
    Filed: October 23, 2013
    Publication date: July 24, 2014
    Applicant: Axiall Ohio, Inc.
    Inventors: Scott A. Sherwood, Stephen Robert Lester
  • Patent number: 8754272
    Abstract: Disclosed is a process for the preparation of cis-1-chloro-3,3,3-trifluoropropene (cis-1233zd) comprising the steps of (a) providing CF3CHClCHCl2 (233da), and (b) treating the 233da with a dechlorinating agent to produce a mixture of compounds including cis-1-chloro-3,3,3-trifluoropropene, preferably wherein the amount of the cis-isomer generated in the reaction is not less than 30%.
    Type: Grant
    Filed: November 12, 2012
    Date of Patent: June 17, 2014
    Assignee: Honeywell International Inc.
    Inventors: Yian Zhai, Andrew Joseph Poss, Michael Van Der Puy, Rajiv Ratna Singh
  • Publication number: 20130190541
    Abstract: A catalyst system for use in oxychlorination, the catalyst system comprising catalyst pellets comprising a catalyst carried on a substrate the pellets having length x, breadth y and depth z, intrinsic density P and bulk density p and diluent beads having length x±25%, breadth y±25% and depth z±25%, intrinsic density?P+25% and a bulk density p ±25%.
    Type: Application
    Filed: July 1, 2011
    Publication date: July 25, 2013
    Applicant: INEOUS EUROPE AG
    Inventors: Lorette Du Preez, Stephen Kevin Lee, Andrea Marsella, Sandro Vidotto
  • Publication number: 20130172191
    Abstract: A method to inhibit the ethylene response in plants with cyclopropene compounds by first generating stable cyclopropane precursor compounds and then converting these compounds to the gaseous cyclopropene antagonist compound by use of a reducing or nucleophilic agent.
    Type: Application
    Filed: February 25, 2013
    Publication date: July 4, 2013
    Inventors: Richard Martin Jacobson, Martha Jean Kelly, William Nixon James
  • Patent number: 8119745
    Abstract: Process for the manufacture of 1,2-dichloroethane (DCE) starting from a stream of ethane which is subjected to a catalytic oxydehydrogenation (ODH) producing a gas mixture containing ethylene then dried and subjected to an absorption to be separated into a fraction enriched with the compounds that are lighter than ethylene containing some of the ethylene conveyed to a chlorination reactor R1 in which most of the ethylene is converted into DCE, and into a fraction F1 which is subjected to a desorption D1 to be separated into an ethylene fraction depleted of the compounds that are lighter than ethylene conveyed to a chlorination reactor R2, the stream of products derived from this reactor being added to the dry gas mixture, and into a fraction F2. Fraction F2 is then subjected to a desorption D2 to be separated into a fraction enriched with ethylene conveyed to an oxychlorination reactor in which most of the ethylene is converted into DCE, and into a fraction F3 which is recycled to the absorption.
    Type: Grant
    Filed: June 22, 2007
    Date of Patent: February 21, 2012
    Assignee: Solvay (Societé Anonyme)
    Inventors: Michel Strebelle, Dominique Balthasart
  • Patent number: 8071827
    Abstract: Process for the manufacture of 1,2-dichloroethane (DCE) starting from a stream of ethane which is subjected to a catalytic oxydehydrogenation (ODH) producing a gas mixture containing ethylene, then dried and subjected to an absorption to be separated into a fraction enriched with the compounds that are lighter than ethylene containing some of the ethylene conveyed to a chlorination reactor in which most of the ethylene is converted to DCE, and into a fraction F1. Fraction F1 is then subjected to a desorption to be separated into a fraction enriched with ethylene conveyed to an oxychlorination reactor in which most of the ethylene is converted into DCE, and into a fraction F3.
    Type: Grant
    Filed: June 22, 2007
    Date of Patent: December 6, 2011
    Assignee: Solvay (Societé Anonyme)
    Inventors: Dominique Balthasart, Michel Strebelle
  • Patent number: 8058490
    Abstract: Process for the manufacture of 1,2-dichloroethane (DCE) starting from a stream of ethane which is subjected to a catalytic oxydehydrogenation (ODH) thus producing a gas mixture containing ethylene which is then dried and conveyed to a chlorination reactor supplied with a flow of chlorine so that at least 10% of the ethylene is converted to DCE. The stream of products derived from the chlorination reactor is then conveyed to an oxychlorination reactor in which the majority of the balance of ethylene is converted to DCE.
    Type: Grant
    Filed: June 22, 2007
    Date of Patent: November 15, 2011
    Assignee: Solvay (Societé Anonyme)
    Inventors: Michel Strebelle, Dominique Balthasart
  • Patent number: 8044251
    Abstract: Described is a process for preparing a halo-olefin comprising contacting a halogenated hydrocarbon with a metal dehalogenating agent, in a solvent, in the presence of a phase transfer catalyst, under conditions sufficient to dehalogenate said halogenated hydrocarbon to produce a product stream comprising said halo-olefin. In one embodiment, the halogenated hydrocarbon is trifluorotrichloroethane and the halo-olefin is chlorotrifluoroethylene.
    Type: Grant
    Filed: April 7, 2010
    Date of Patent: October 25, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Xuehui Sun
  • Publication number: 20110251443
    Abstract: The invention relates to a process for the manufacture of vinyl chloride monomer comprising the preparation of acetylene from one or more renewable starting materials and then the reaction of the acetylene with hydrogen chloride in order to form vinyl chloride monomer. The invention also relates to the vinyl chloride monomer obtained and to its use.
    Type: Application
    Filed: November 30, 2009
    Publication date: October 13, 2011
    Inventor: Jean-Luc Dubois
  • Patent number: 7884255
    Abstract: Chemical Production Processes and Systems. Chemical production processes are provided that include replacing a halogen of an unsaturated halocarbon to produce an unsaturated hydrohalocarbon. Chemical production systems are provided that include a reaction zone coupled to first and second reservoirs, the first reservoir containing an unsaturated halocarbon and the second reservoir containing a hydrogenating reagent with the system being configured to expose the unsaturated halocarbon of the first reservoir to the hydrogenating agent of the second reservoir within the reaction zone.
    Type: Grant
    Filed: August 26, 2005
    Date of Patent: February 8, 2011
    Inventor: Vicki Hedrick
  • Publication number: 20100268001
    Abstract: Described is a process for preparing a halo-olefin comprising contacting a halogenated hydrocarbon with a metal dehalogenating agent, in a solvent, in the presence of a phase transfer catalyst, under conditions sufficient to dehalogenate said halogenated hydrocarbon to produce a product stream comprising said halo-olefin. In one embodiment, the halogenated hydrocarbon is trifluorotrichloroethane and the halo-olefin is chlorotrifluoroethylene.
    Type: Application
    Filed: April 7, 2010
    Publication date: October 21, 2010
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: MARIO JOSEPH NAPPA, Xuehui Sun
  • Patent number: 7704370
    Abstract: An aqueous solution of sodium chloride is electrolyzed in a cell (1) with an ion permselective membrane to produce, on the one hand, chlorine (16) which is converted in a chlorine production unit (6) and, on the other, an aqueous sodium hydroxide solution (19), which is carbonated using a flue gas (13) from an electricity and steam cogeneration unit (5), and the resulting carbonated solution (18) is evaporated to produce sodium carbonate crystals (21).
    Type: Grant
    Filed: March 7, 2006
    Date of Patent: April 27, 2010
    Assignee: Solvay (Societe Anonyme)
    Inventors: Francis Coustry, Michel Hanse
  • Publication number: 20100041927
    Abstract: Process and apparatus to form vinyl chloride monomer from ethylene dichloride in a cracking furnace, including a firebox chamber having a thermal protective layer disposed on refractory walls and/or process tubes disposed within the chamber, a quencher to form vinyl chloride monomer, and fractionator separate products. The thermal protective layer which contains an inorganic adhesive for metal/alloy tubes or colloidal silica and/or colloidal alumina for refractory walls or ceramic tubes, a filler, and one or more emissivity agents.
    Type: Application
    Filed: August 12, 2008
    Publication date: February 18, 2010
    Inventors: John W. Olver, Jason Andrew Simmons
  • Publication number: 20090270579
    Abstract: Process for the manufacture of 1,2-dichloroethane (DCE) starting from a stream of ethane which is subjected to a catalytic oxydehydrogenation (ODH) producing a gas mixture containing ethylene, then dried and subjected to an absorption to be separated into a fraction enriched with the compounds that are lighter than ethylene containing some of the ethylene conveyed to a chlorination reactor in which most of the ethylene is converted to DCE, and into a fraction F1. Fraction F1 is then subjected to a desorption to be separated into a fraction enriched with ethylene conveyed to an oxychlorination reactor in which most of the ethylene is converted into DCE, and into a fraction F3.
    Type: Application
    Filed: June 22, 2007
    Publication date: October 29, 2009
    Applicant: SOLVAY (Société Anonyme)
    Inventors: Dominique Balthasart, Michel Strebelle
  • Patent number: 7473810
    Abstract: Provided is a method for selectively preparing 2-chloropentafluoropropene comprising catalytic dechlorination of 1,2,2-trichloro-1,1,3,3,3-pentafluoropropane in the presence of hydrogen and a noble metal catalyst. Also provided is method for dechlorinating a vicinal chloride substituted organic compound using a palladium/barium sulfate catalyst.
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: January 6, 2009
    Assignee: Honeywell International Inc.
    Inventors: Michael Van Der Puy, Jingji Ma
  • Patent number: 7312368
    Abstract: A method for the selective reduction of an aromatic compound. The present invention provides a method for pre-venting the reduction of at least one halogen substituted aromatic ring of an aromatic compound, while allowing the reduction of at least one functional group on the aromatic compound. In the present invention at least one hydroxyl group is placed on the at least one halogen substituted aromatic ring to be protected from reduction. The aromatic compound is then reacted with at least one alkali metal in at least one nitrogen containing base and at least one alcohol at a ratio of the alcohol to the nitrogen containing base at which the aromatic ring with the hydroxyl group is protected from reduction, while the desired functional group is reduced.
    Type: Grant
    Filed: December 2, 2004
    Date of Patent: December 25, 2007
    Assignee: Mallinckrodt Inc.
    Inventors: Peter Xianqi Wang, Frank W. Moser
  • Patent number: 7164050
    Abstract: A process for preparing a halo-olefin to minimize one or more side reactions which form at least one impurity, said process comprising contacting a halogenated hydrocarbon with a metal dehalogenating agent dissolved in a solvent under conditions sufficient to dehalogenate said halogenated hydrocarbon to produce a product stream comprising said halo-olefin and at least one impurity, said metal dehalogenating agent having an average particle size within a range of average particle sizes, said impurity concentration of said product stream being essentially constant within said range and increasing significantly below said range.
    Type: Grant
    Filed: May 2, 2005
    Date of Patent: January 16, 2007
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, William R. Jones
  • Patent number: 6984763
    Abstract: An oxidative halogenation and optional dehydrogenation process involving contacting a reactant hydrocarbon having three or more carbon atoms, such as propane or propene, or a halogenated derivative thereof, with a source of halogen, and optionally, a source of oxygen in the presence of a rare earth halide or rare earth oxyhalide catalyst, so as to form a halogenated hydrocarbon product, such as allyl chloride, having three or more carbon atoms and having a greater number of halogen substituents as compared with the reactant hydrocarbon, and optionally, an olefinic co-product, such as propene. The less desired of the two products, that is, the halogenated hydrocarbon or the olefin as the case may be, can be recycled to the process to maximize the production of the desired product.
    Type: Grant
    Filed: April 23, 2002
    Date of Patent: January 10, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Albert E. Schweizer, Mark E. Jones, Daniel A. Hickman
  • 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
  • Publication number: 20040267064
    Abstract: The invention concerns a method for obtaining directly polymerisable vinyl chloride which consists in subjecting a cooled raw product derived from of pyrolysis of 1,2-dichloroethane, to another cooling process at a temperature not more than 40° C., under pressure ranging between 10 to 15 bars then in leaving it at substantially identical temperature and pressure levels for a duration not more than 20 minutes. The invention also concerns a device for implementing the method.
    Type: Application
    Filed: August 19, 2004
    Publication date: December 30, 2004
    Inventors: Beatrice Rondot, Francois Vanney
  • 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: 6166277
    Abstract: A process for evaporating 1, 2-dichloroethane (EDC) prior to its thermal decomposition (pyrolysis) is provided so that it facilitates the heating of the liquid-phase EDC at temperatures below 100.degree. C. to meet the inlet conditions for the pyrolysis zone, while dispensing with the need for an evaporation zone and exploiting sensible heat recovery at the same time. This is achieved in that the liquid-phase EDC is first pressurized to attain a value above its critical pressure (5.36 MPa) and then heated to attain at least its critical temperature (approx. 288.degree. C.).
    Type: Grant
    Filed: December 20, 1999
    Date of Patent: December 26, 2000
    Assignee: Krupp Uhde GmbH
    Inventor: Friedrich Seidelbach
  • Patent number: 5716590
    Abstract: Catalytic dehalogenation (or hydrodehalogenation) of halogen-containing compounds of elements of group IV of the periodic table in the presence of hydrogen is carried out using a finely-dispersed catalytically active material which comprises silicon and at least one transition metal, and which is characterized by high catalytic activity and stability. This process can be used, for example, for synthesizing compounds or alternatively for decomposing halogen-containing compounds, for instance in waste-water or waste-gas purification processes. It is also suitable for dehalogenation (hydrodehalogenation) of halogen-containing silane compounds, for instance of silicon tetrachloride or alkyl trichlorosilane compounds, and the original purity of the silanes used as starting materials is retained by the products. Tetrachlorosilane, for example, can be converted into trichlorosilane.
    Type: Grant
    Filed: December 8, 1994
    Date of Patent: February 10, 1998
    Assignee: Wacker-Chemie GmbH
    Inventors: Gerhard Roewer, Uwe Paetzold, Holger Walter
  • Patent number: 5705728
    Abstract: The present invention provides an efficient process for the production of ethylene or a mixture of ethylene and vinyl chloride, in which some 1,2-dichloroethane (EDC) may also be produced, by reacting chlorine with ethane. The process is characterized by a conversion of ethane per pass through the reactor of at least about 50%, and a combined molar yield of ethylene and vinyl chloride of at least about 80% based on the ethane consumed. In accordance with this invention, there is provided a process for preparing ethylene or a mixture of ethylene and vinyl chloride by the reaction of ethane and chlorine which comprises:(a) providing a stream of ethane feed gas and a stream of chlorine feed gas;(b) preheating either said ethane stream only or both said ethane and chlorine streams;(c) thoroughly mixing said ethane and chlorine feed gases within about one second and at a molar ratio of ethane to chlorine of at least about 0.9:1.
    Type: Grant
    Filed: February 10, 1995
    Date of Patent: January 6, 1998
    Assignee: Occidental Chemical Corporation
    Inventors: Krishnan Viswanathan, Hang-Chang Bobby Chen, Sidney W. Benson
  • Patent number: 5705720
    Abstract: A thermal process for cracking 1,2-dichloroethane to form vinyl chloride comprising heating 1,2-dichloroethane in a reaction zone at a temperature between 300.degree. and 650.degree. C. under an absolute pressure between 1 and 40 bars; said heating being conducted in the presence of hydrochloric acid.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: January 6, 1998
    Assignee: Atochem
    Inventors: Claude Demaiziere, Jean Lesparre, Yves Correia
  • Patent number: 5663472
    Abstract: A process for reacting ethane with chlorine to produce a mixture of ethylene and vinyl chloride is disclosed. The process involves the intimate mixing of ethane and chlorine in an ethane to chlorine ratio of at least about 0.9:1 at a temperature such that ethane and chlorine do not react during mixing, and heating the mixture to a temperature above about 215.degree. C. to commence the reaction, allowing the reaction to proceed for a period of less than about 1 minute, and providing sufficient heat to the reacting mixture so that the reacted mixture will have a temperature between about 400.degree. C. and about 800.degree. C.
    Type: Grant
    Filed: February 7, 1995
    Date of Patent: September 2, 1997
    Assignee: University of Southern California
    Inventors: Sidney W. Benson, Maja A. Weissman
  • Patent number: 5600042
    Abstract: The purpose of this invention is to describe a new process for the manufacture of choroethene (C.sub.2 H.sub.3 Cl). This new process involves the use or ethylene (C.sub.2 H.sub.4) as a feedstock. Highly chlorinated ethenes or methanes are used as chlorinating agents. The corresponding less chlorinated ethenes or methanes are recovered as co-products or recycled to the process to produce additional chloroethene. The distribution of the products may be adjusted so that chloroethene is the major product.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: February 4, 1997
    Inventors: Wu-Chi Chen, Harvey R. Chen
  • Patent number: 5476979
    Abstract: A process for converting a chlorinated alkene feedstock including two or more chlorines to reaction products including a less-chlorinated alkene in a commercially substantial proportion, comprising reacting the chlorinated alkene feedstock with hydrogen in the presence of a catalyst consisting essentially of a Group VIII metal other than rhodium, palladium or ruthenium and a Group IB metal on a support.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: December 19, 1995
    Assignee: The Dow Chemical Company
    Inventors: Larry N. Ito, Craig B. Murchison, Michael T. Holbrook, A. Dale Harley, David D. Smith
  • Patent number: 5453557
    Abstract: A process for the catalytic conversion of various chlorinated hydrocarbon byproducts and waste products especially to less chlorinated, useful or salable products, in which a chlorinated hydrocarbon feedstock containing two or more chlorines is reacted with hydrogen in the presence of a catalyst consisting essentially of an active hydrogenating metal component such as platinum in elemental or compound form, and a surface segregating metal component such as copper in elemental or compound form on a support.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: September 26, 1995
    Assignee: The Dow Chemical Company
    Inventors: A. Dale Harley, Michael T. Holbrook, David D. Smith, Mark D. Cisneros, Larry N. Ito, Craig B. Murchison
  • Patent number: 5345032
    Abstract: A method for dehalogenation of organohalogen compounds, e.g. environmental pollutants in industrial waste. The organohalogen is reacted with a reducing agent in the presence of a selected metal-centered corrin, porphyrin or phthalocyanine complex. Preferred complexes are hydrolysis products of cyanocobalamin, of formula (I), in which R.sup.1 is NH.sub.2 or OH, R.sup.2 is H, CH.sub.2 CH.sub.2 COOH or CH.sub.2 CH.sub.2 CONH.sub.2, R.sup.3 is H, CH.sub.2 CH.sub.2 COOH or CH.sub.2 CH.sub.2 CONH.sub.2, and R.sup.4 is NHCH.sub.2 CH(OH)CH.sub.3, OH or NH.sub.2. The complex is preferably immobilized on a substrate. Some novel metal-centered porphyrin complexes are also described. A dehalogenation apparatus using the method of the invention is also described.
    Type: Grant
    Filed: April 19, 1993
    Date of Patent: September 6, 1994
    Assignee: The Public Health Laboratory Service Board
    Inventors: Trevor S. Marks, Andrew Maule
  • 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: 5227560
    Abstract: Active methine compounds are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylonium hydroxide. Chlorinated products, preferably tertiary alkyl chloro compounds, are produced. The tertiary alkyl chloro compounds are useful in elimination reactions, preferably reactions with base, to form unsaturated compounds, particularly compounds having a vinylidene or exomethylene group.
    Type: Grant
    Filed: November 7, 1991
    Date of Patent: July 13, 1993
    Assignee: The Dow Chemical Company
    Inventors: Katherine S. Clement, W. Frank Richey, Marlin E. Walters
  • Patent number: 5208393
    Abstract: A process for the manufacture of chloroform by catalytic hydrogenolysis of carbon tetrachloride in liquid phase, wherein liquid phase carbon tetrachloride is reacted with hydrogen gas or a gas containing molecular hydrogen, at a pressure below 8,000 kPa and at a temperature below 250.degree. C., in the presence of a catalyst formed by a metal selected from the group consisting of palladium, rhodium, ruthenium and platinum, deposited on a substrate and held in suspension in the liquid.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: May 4, 1993
    Assignee: Ercros, S.A.
    Inventors: Emilio Tijer Miquel, Jose M. Sule Gimenez, Antonio Cortes Arroyo, Xose L. Seoane Gomez, Adolfo Arcoya Martin
  • 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: 5177272
    Abstract: The invention relates to a process for preparing perhalogenated olefins which comprises reacting a perhalogenated alkane, having at least one atom of a halogen different from fluorine, with a tris-dialkylamino phosphine at temperature not higher than 60.degree. C.
    Type: Grant
    Filed: January 23, 1992
    Date of Patent: January 5, 1993
    Assignee: Ausimont S.p.A.
    Inventors: Vittorio Montanari, Darryl D. Desmarteau, Walter Navarrini
  • Patent number: 5097081
    Abstract: The highly chlorinated methanes, e.g., carbon tetrachloride, are improvedly dechlorinated by reacting same with hydrogen in the presence of oxygen or an oxygen-containing gas, e.g., air, and a catalytically effective amount of a metal of the copper or precious metal Groups of the Periodic Table, typically in the form of a fixed or fluidized bed thereof, and advantageously in the gaseous phase.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: March 17, 1992
    Assignee: Atochem
    Inventors: Yves Correia, Joseph Nowocien
  • Patent number: 5091603
    Abstract: In the process, a copper/rhodium catalyst impregnated with 0.1 to 10.0% by weight, based on the total weight of active charcoal catalyst support and active components, of a water-soluble phosphonium halide is employed for the preparation of trichloroelethylene from perchloroethylene and hydrogen.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: February 25, 1992
    Assignee: Wacker-Chemie GmbH
    Inventors: Willibald Dafinger, Wolfdietrich Gabler, Eduard Pichl, Roman Hierzegger
  • Patent number: 4943671
    Abstract: Organic halogen compounds in which one or more halogen atoms are covalently bonded to the carbon are subjected to reductive dehalogenation by reaction with a hydrocarbon in the presence of carbon at elevated temperatures with formation of a hydrogen halide, by a process in which the dehalogenation is carried out in the presence of iron powder or an iron compound as a cocatalyst, at from 100.degree. to 450.degree. C.
    Type: Grant
    Filed: May 2, 1988
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Manfred Sauerwald, Herbert Krug, Matthias Irgang
  • Patent number: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4691053
    Abstract: A novel process for producing oxygen-containing organic compounds with high selectivity and good yield by oxidizing organic compounds under mild conditions is provided, which process comprises using as a catalyst for the oxidation, a complex (M.sub.m X.sub.n.L.sub.l) consisting of a transition metal compound (M.sub.m X.sub.n) and an organic phosphorous compound (L) as a ligand, wherein M represents a transition metal belonging to group I, group IV.about.VII or iron group in group VIII of the periodic table; X represents an anion such as a halogen; ligand L represents an organic phosphorous compound; and m and n mean a number of the atomic valence of said transition metal (ion) M and said anion X, respectively, and l means a number of said ligand.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: September 1, 1987
    Assignee: Babcock-Hitachi Kabushiki Kaisha
    Inventors: Mutsuo Yamada, Yasuyuki Nishimura, Yoshijiro Arikawa, Takanori Kuwahara, Taiji Kamiguchi, Hirotoshi Tanimoto
  • Patent number: 4558167
    Abstract: Hydrogen chloride is recovered from a mixture with propylene by extractive distillation with an inert extraction solvent to minimize reaction between hydrogen chloride and propylene during such distillation. The temperature and pressure conditions are coordinated with the extraction solvent and amount thereof to prevent the presence of hydrogen chloride in a liquid state. The process is particularly suitable for recovering hydrogen chloride in the production of allyl chloride by thermal chlorination of propylene.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: December 10, 1985
    Assignee: The Lummus Company
    Inventors: Herbert Riegel, Chiung-Yuan Huang, Vincent A. Strangio
  • Patent number: RE34761
    Abstract: In the process, a copper/rhodium catalyst impregnated with 0.1 to 10.0% by weight, based on the total weight of active charcoal catalyst support and active components, of a water-soluble phosphonium halide is employed for the preparation of trichloroelethylene from perchloroethylene and hydrogen.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: October 18, 1994
    Assignee: Wacker-Chemie GmbH
    Inventors: Willibald Dafinger, Wolfdietrich Gabler, Eduard Pichl, Roman Hierzegger