Processes Of Preparing, Purifying, Or Recovering Unsaturated Compound Patents (Class 570/216)
  • Patent number: 9828313
    Abstract: There are provided methods and systems for an electrochemical cell including an anode and a cathode where the anode is contacted with a metal ion that converts the metal ion from a lower oxidation state to a higher oxidation state. The metal ion in the higher oxidation state is reacted with an unsaturated hydrocarbon and/or a saturated hydrocarbon to form products. Separation and/or purification of the products as well as of the metal ions in the lower oxidation state and the higher oxidation state, is provided herein.
    Type: Grant
    Filed: July 30, 2014
    Date of Patent: November 28, 2017
    Assignee: Calera Corporation
    Inventors: Michael Joseph Weiss, Ryan J Gilliam, Kyle Self, Gal Mariansky, Margarete K Leclerc, Riyaz Mohammed Shipchandler, Jacob Nagar
  • 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
  • Patent number: 9000240
    Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.
    Type: Grant
    Filed: May 15, 2012
    Date of Patent: April 7, 2015
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Publication number: 20150031925
    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 1, 2014
    Publication date: January 29, 2015
    Inventors: Scott A. Sherwood, Stephen Robert Lester
  • Patent number: 8936757
    Abstract: Apparatuses and processes are provided for stripping gaseous hydrocarbons from particulate material. One process comprises the step of contacting particles containing hydrocarbons with a stripping vapor in countercurrent flow to remove at least a portion of the hydrocarbons with the stripping vapor to form stripped particles. Contacting the particles includes advancing the particles down a sloping element of a structured packing toward a reinforcing rod that is disposed along a lower channel portion of the sloping element. The particles are advanced over the reinforcing rod. The particles are contacted with the stripping vapor that is rising up adjacent to the lower channel portion.
    Type: Grant
    Filed: December 28, 2011
    Date of Patent: January 20, 2015
    Assignee: UOP LLC
    Inventors: Erick D. Gamas-Castellanos, Mitchell John Kowalczyk
  • Patent number: 8921621
    Abstract: A process for the manufacture of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) at commercial scale from the reaction of HCC-240 and HF is disclosed. In one embodiment, HCC-240fa and HF are fed to a reactor operating at high pressure. Several different reactor designs useful in this process include; a stirred-tank reactor (batch and/or continuous flow); a plug flow reactor; a static mixer used as a reactor; at least one of the above reactors operating at high pressure; optionally combined with a distillation column running at a lower pressure; and combinations of the above; and/or with a distillation column. The resulting product stream consisting of 1233zd, HCl, HF, and other byproducts is partially condensed to recover HF by phase separation. The recovered HF phase is recycled to the reactor. The HCl is scrubbed from the vapor stream and recovered as an aqueous solution.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: December 30, 2014
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Daniel C. Merkel
  • Publication number: 20140323744
    Abstract: The specification relates to compounds and process for the preparation of a compound of formula 7, where LG is a leaving group and hal is a halide and is Cl, Br or I. The compound of formula 7 can be useful in the preparation of natural products, such as halichondrin and its derivatives.
    Type: Application
    Filed: November 29, 2012
    Publication date: October 30, 2014
    Inventors: Fabio E.S. Souza, Huzaifa Rangwala, Boris Gorin, Ming Pan
  • Patent number: 8558041
    Abstract: The present invention provides isothermal multitube reactors suitable for the production of chlorinated and/or fluorinated propene and higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes. The reactors utilize a feed mixture inlet temperature at least 20° C. different from a desired reaction temperature.
    Type: Grant
    Filed: October 8, 2010
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies, LLC
    Inventors: Max M. Tirtowidjojo, Hua Bai, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt F. Hirsekorn, Manfred Kokott, William J. Kruper, Jr., Thomas U. Luebbe, Avani M. Patel, Shirley S. Sexton, Peter Wenzel, Marcus Wobser
  • Patent number: 8552229
    Abstract: With a method for utilization of the reaction heat that occurs in the production of 1,2-dichloroethane from ethylene, by reaction with oxygen and hydrochloride (oxychlorination), in a fluidized bed reactor, with dissipation of this reaction heat through cooling pipe bundles situated within the reactor, positioned in the fluidized bed, utilization of the heat is supposed to be improved, while simultaneously reducing the size of the corresponding system elements. This is achieved in that part of the reaction heat is dissipated by heating boiler feed water, whereby the heated boiler feed water is used to heat heat sinks in the production process.
    Type: Grant
    Filed: September 2, 2009
    Date of Patent: October 8, 2013
    Assignees: ThyssenKrupp Uhde GmbH, Vinnolit GmbH & Co. KG
    Inventors: Ulrike Gnabs, Michael Benje, Walter Kern
  • Publication number: 20130209361
    Abstract: The present invention relates to a new synthetic process in which an alkyne and an azide react to form a radioisotopic bioconjugate construct. The reaction is particularly useful for producing compounds for use in imaging and radiotherapy applications. The present invention also provides bioconjugate labels and further relates to the use of these compounds in diagnostic and therapeutic methods. In addition, the invention provides a related process for introducing a radioisotopic halogen atom into a terminal alkyne.
    Type: Application
    Filed: August 12, 2011
    Publication date: August 15, 2013
    Applicant: UCL BUSINESS PLC
    Inventors: Erik Arstad, Ran Yan
  • Patent number: 8481793
    Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: July 26, 2012
    Date of Patent: July 9, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung, Konstantin A. Pokrovski
  • Publication number: 20130165648
    Abstract: The present invention provides processes and intermediates for the preparation of 3-benzazepines and salts thereof which can be useful as serotonin (5-HT) receptor agonists for the treatment of, for example, central nervous system disorders such as obesity.
    Type: Application
    Filed: September 14, 2012
    Publication date: June 27, 2013
    Inventors: Beverly L. Wolgast, Charles A. Gilson, III, Shelley Aytes, Scott A. Estrada, Dipanjan Sengupta, Brian Smith, Max Rey, Ulrich Weigl, Heidedore Jlsabeth Rey-Papina
  • Patent number: 8449729
    Abstract: A process for converting a tertiary halogenated hydrocarbons in a tertiary halogenated hydrocarbon-containing stream to a corresponding unhalogenated or less-halogenated unsaturated hydrocarbon product with the release of hydrogen halide involves contacting the tertiary halogenated hydrocarbon with a sorbent-type dehydrohalogenation catalyst in a reaction zone and optionally passing a stripping gas through the reaction zone to remove vapor phase reaction products from the reaction zone.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: May 28, 2013
    Assignee: Dow AgroSciences, LLc
    Inventors: Michael L. Trippeer, Timothy C. Frank, Patrick H. Au-Yeung, Jason L. Bronkema, Robin K. Johnston, Mukund R. Patel, Bruce S. Holden, Terrence McCabe, Daniel A. Hickman
  • Patent number: 8404907
    Abstract: Disclosed is a process for making one isomer of CF3CH?CHCl. More particularly, the invention comprises the production of CF3C?CCl and its selective reduction to cis-1-chloro-3,3,3-trifluoropropene (CF3CH?CHCl).
    Type: Grant
    Filed: February 18, 2011
    Date of Patent: March 26, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Andrew Joseph Poss, Rajiv Ratna Singh, Michael Van Der Puy, Ryan J. Hulse
  • Publication number: 20120319062
    Abstract: A flame retardant brominated rubber polymeric composition, wherein the composition can include ethylene propylene ethylidene norbornene rubber polymer and from 12 weight percent to 55 weight percent of bromine covalently bonded thereto. The method can include dissolving a liquid ethylene propylene ethylidene norbornene rubber polymer in hexane with myrcene, forming the composition. The method can include dissolving ethylene propylene ethylidene norbornene rubber polymer in hexane, forming a solution, and adding bromine, or blending N-bromo-succinimide into the solution, forming a suspension. The method can include heating the suspension and stifling the suspension until all bromine in the N-bromo-succinimide has reacted with the ethylene propylene ethylidene norbornene rubber polymer, forming the composition as a solid in a liquid. The method can include removing the liquid from the solid, and flashing off the hexane from the liquid to extract the composition.
    Type: Application
    Filed: June 15, 2012
    Publication date: December 20, 2012
    Applicant: LION COPOLYMER, LLC
    Inventors: Jorge Soto, Jay Reimers, Deepak Rasiklal Parikh
  • Patent number: 8252965
    Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: August 12, 2009
    Date of Patent: August 28, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Publication number: 20120215041
    Abstract: Disclosed is a process for making one isomer of CF3CH?CHCl. More particularly, the invention comprises the production of CF3C?CCl and its selective reduction to cis-1-chloro-3,3,3-trifluoropropene (CF3CH?CHCl).
    Type: Application
    Filed: February 18, 2011
    Publication date: August 23, 2012
    Inventors: Haridasan K. Nair, Andrew Joseph Poss, Rajiv Ratna Singh, Michael Van Der Puy, Ryan J. Hulse
  • Publication number: 20120065412
    Abstract: The present invention relates to a process for producing hydrocarbons from methane, which comprises, in a first stage (i), reacting methane to form ethylene and, in a later stage (ii), reacting the product mixture obtained in stage (i) which comprises ethylene and methane to give higher-value hydrocarbons. In addition, the present invention relates to a plant for producing hydrocarbons from methane in which, in a single plant strand, a plurality of plant units are arranged successively in series comprising: a first reactor A for carrying out a conversion from methane to ethylene a second reactor B for carrying out a conversion from ethylene to higher-value hydrocarbons.
    Type: Application
    Filed: May 10, 2010
    Publication date: March 15, 2012
    Applicant: BASF SE
    Inventors: Radwan Abdallah, Torsten Mäurer, Gerhard Theis
  • Patent number: 8030531
    Abstract: 2,3-dichlorobutadiene-1,3 of high purity is produced from 1,2,3,4-tetrachlorobutane by a process comprising the steps of dehydrochlorination, chlorination of the reaction product obtained in the dehydrochlorination step and subsequent separation of a 2,3-dichlorobutadiene-1,3 composition from the reaction product of the chlorination step.
    Type: Grant
    Filed: December 16, 2008
    Date of Patent: October 4, 2011
    Assignee: Dupont Performance Elastomers LLC
    Inventor: Terry Wayne Redwine
  • Publication number: 20110237848
    Abstract: The invention is directed to a process and to an apparatus for saving fuel in furnaces for thermal dissociation of halogenated aliphatic hydrocarbons, especially of 1,2-dichloroethane, using chemical dissociation promoters or physical measures which initiate the dissociation reaction. The initiation of the dissociation reaction lowers the temperature level in the reaction mixture with the same conversion. This can also lower the mean firing chamber temperature and save fuel. In a preferred process variant, flue gas leaving the convection zone of the dissociation oven is analyzed and its dew point is calculated. The dew point of the flue gas or the conversion of the dissociation reaction serves as command parameter for the intensity of the physical measure for initiation and/or for the amount of the chemical dissociation promoter added and/or for the amount of fuel. In a further preferred process variant, the latent heat content of the flue gas is used to preheat the burner air or other media.
    Type: Application
    Filed: September 3, 2009
    Publication date: September 29, 2011
    Inventors: Michael Benje, Peter Kammerhofer, Klaus Krejci, Rainer Kampschulte, Helmut Grumann
  • Patent number: 8026400
    Abstract: Purified chlorinated alkenes are produced by a process in which a mixture of i) a first chlorinated alkene that has at least one beta-chlorine substituent and no alpha-chlorine substituents and ii) a second chlorinated alkene that has at least one alpha-chlorine substituent is contacted with chlorine in an amount sufficient to further chlorinate the second chlorinated alkene, but which is insufficient to cause conversion of more than 20% of the first chlorinated alkene.
    Type: Grant
    Filed: December 16, 2008
    Date of Patent: September 27, 2011
    Assignee: Dupont Performance Elastomers LLC
    Inventor: Terry Wayne Redwine
  • Publication number: 20110172448
    Abstract: A cost effective process is presented for carrying out catalytic, in particular also exothermic, endothermic or autothermal reactions with optimum yield and selectivity. The system used is a wall-flow monolith which forces a flow from the inlet channel through the porous wall into the outlet channel by reciprocal closure of the gas channels. This is operated such that mass transfer and heat transport are determined virtually exclusively by convection, and diffusion-related thermal conduction phenomena can be neglected.
    Type: Application
    Filed: June 24, 2009
    Publication date: July 14, 2011
    Inventors: Martin Votsmeier, Susanne Ungermann, Juergen Gieshoff, Thomas Kreuzer
  • Publication number: 20110087056
    Abstract: The present invention provides adiabatic plug flow reactors suitable for the production of chlorinated and/or fluorinated propene and higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes. The reactors comprise one or more designs that minimize the production of by-products at a desired conversion.
    Type: Application
    Filed: October 8, 2010
    Publication date: April 14, 2011
    Applicant: DOW GLOBAL TECHNOLOGIES
    Inventors: Max M. Tirtowidjojo, Hua Bai, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt F. Hirsekorn, Manfred Kokott, William J. Kruper, JR., Thomas U. Luebbe, Thomas J. Parsons, Avani Maulik Patel, Marcus Wobser
  • Publication number: 20110082267
    Abstract: Process for the manufacture of 1,2-dichlorethane and of at least one ethylene derivative compound which is different from 1,2-dichloroethane starting with a hydrocarbon source according to which: a) the hydrocarbon source is subjected to a simplified cracking which produces a mixture of products containing ethylene and other constituents; b) the mixture of products is separated at least into a fraction A enriched with compounds which are lighter than ethylene, containing part of the ethylene, into a fraction B enriched with ethylene and into a heavy fraction C; and c) one fraction among fraction A and fraction B is conveyed to the manufacture of 1,2-dichloroethane and optionally of any compound derived therefrom, optionally after having been subjected to an acetylene hydrogenation, while the other fraction is conveyed to the manufacture of at least one ethylene derivative compound manufactured directly starting with ethylene which is different from 1,2-dichloroethane and optionally of any compound derived the
    Type: Application
    Filed: May 29, 2009
    Publication date: April 7, 2011
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Michel Lempereur, Dominique Balthasart, Michel Strebelle, Massimo Giansante
  • Publication number: 20100216958
    Abstract: Isobutene, isoprene, and butadiene are obtained from mixtures of C4 and/or C5 olefins by dehydrogenation. The C4 and/or C5 olefins can be obtained by dehydration of C4 and C5 alcohols, for example, renewable C4 and C5 alcohols prepared from biomass by thermochemical or fermentation processes. Isoprene or butadiene can be polymerized to form polymers such as polyisoprene, polybutadiene, synthetic rubbers such as butyl rubber, etc. in addition, butadiene can be converted to monomers such as methyl methacrylate, adipic acid, adiponitrile, 1,4-butadiene, etc. which can then be polymerized to form nylons, polyesters, polymethylmethacrylate etc.
    Type: Application
    Filed: February 24, 2010
    Publication date: August 26, 2010
    Inventors: Matthew W. Peters, Joshua D. Taylor, Leo E. Manzer, David E. Henton
  • Patent number: 7691282
    Abstract: Disclosed is a hydrofluoroether compound comprising two terminal fluoroalkyl groups and an intervening substituted or unsubstituted oxymethylene group, each of the fluoroalkyl groups comprising only one hydrogen atom and, optionally, at least one catenated (that is, in-chain) heteroatom; with the proviso that the hydrogen atom is part of a monofluoromethylene moiety.
    Type: Grant
    Filed: September 8, 2005
    Date of Patent: April 6, 2010
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Michael G. Costello
  • Patent number: 7674944
    Abstract: Catalysts and methods for alkane oxydehydrogenation are disclosed. The catalysts of the invention generally comprise (i) nickel or a nickel-containing compound and (ii) at least one or more of titanium (Ti), tantalum (Ta), niobium (Nb), hafnium (Hf), tungsten (W), yttrium (Y), zinc (Zn), zirconium (Zr), or aluminum (Al), or a compound containing one or more of such element(s). In preferred embodiments, the catalyst is a supported catalyst, the alkane is selected from the group consisting of ethane, propane, isobutane, n-butane and ethyl chloride, molecular oxygen is co-fed with the alkane to a reaction zone maintained at a temperature ranging from about 250° C. to about 350° C., and the ethane is oxidatively dehydrogenated to form the corresponding alkene with an alkane conversion of at least about 10% and an alkene selectivity of at least about 70%.
    Type: Grant
    Filed: April 11, 2007
    Date of Patent: March 9, 2010
    Assignee: Celanese International Corporation
    Inventor: Yumin Liu
  • Patent number: 7304192
    Abstract: The present invention relates to a simple method for efficiently producing aromatic-substituted chlorinated hydrocarbons, for example, high-purity cumyl chloride (1,4-bis(1-chloro-1-methylethyl)benzene, p-DCC) that can be used as an initiator for cationic polymerization. A corresponding tertiary alcohol such as 1,4-bis(1-hydroxy-1-methylethyl)benzene is mixed with aqueous hydrochloric acid and subjected to stirring, and then the resulting organic layer is brought into contact with a hydrogen chloride gas to produce high-quality aromatic-substituted chlorinated hydrocarbon in high yield. Furthermore, in order to purify a mixture containing a chlorinated hydrocarbon compound, the mixture being produced by reaction between an aqueous solution of a metal hypochiorite and a protonic acid, the mixture is allowed to react with an aqueous alkaline solution to form an alcohol compound. Then, a solid is isolated by solid-liquid separation and chlorinated again with the aqueous hydrochloric acid.
    Type: Grant
    Filed: July 2, 2003
    Date of Patent: December 4, 2007
    Assignee: Kaneka Corporation
    Inventors: Takeshi Kawamura, Chiho Yoshimi, Hidetoshi Odaka
  • 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: 7196235
    Abstract: There is provided a process for producing a fluorinated vinyl ether from a fluorinated acid fluoride compound having an ester group as a precursor of a carboxylic acid group, or a SO2F group as a precursor of a sulfonic acid group, in high yield by simple operations. Said process is a production process comprising pyrolyzing a carboxylic acid potassium salt with a specific structure represented by the following formula in the absence of a solvent and/or while maintaining the salt in the solid state: wherein X is —CO2R or —SO2F, and R is an alkyl group.
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: March 27, 2007
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Nobuto Hoshi, Nobuyuki Uematsu, Masanori Ikeda
  • Patent number: 7186869
    Abstract: A process for removing one or more unsaturated halocarbons from a halocarbon mixture comprising one or more unsaturated halocarbons and one or more saturated halocarbons, which process comprises contacting the halocarbon mixture with a mixture of a solid chemical oxidant and a solid support in the presence of water.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: March 6, 2007
    Assignee: Ineos Fluor Holdings Limited
    Inventors: Stephen Andrew Flaherty, Paul Hendry Stewart
  • 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: 7112709
    Abstract: A method for recovering much of the carbon and chlorine value in the heavy ends and other undesired by-products formed during the production of a C3 or higher polychlorinated alkane through the reaction of carbon tetrachloride with an olefine or chlorinated olefine, the improvement comprising the step of first separating the heavy ends and any other higher or lower boiling chlorohydrocarbon impurities from most of the desired product, and subjecting the separated heavy ends and impurities therewith to a high temperature exhaustive chlorination to produce carbon tetrachloride, tetrachloroethene, and minor amounts of hexachlorobutadiene and hexachlorobenzene by-products.
    Type: Grant
    Filed: September 9, 2003
    Date of Patent: September 26, 2006
    Assignee: Vulcan Chemicals
    Inventor: Rodney L. Klausmeyer
  • Patent number: 7102042
    Abstract: A method for preparing a composition of the formula in a yield greater than 50% where R1 is C 1-20 comprising the steps of combining fluorene or dibromo flourene, an excess of alkali metal hydroxide and a halogenated alkyl in the presence of a phase transfer catalyst but in the absence of a polar aprotic solvent; heating the combination; and separating the dialkylated fluorene or dialylated dibromo fluorene. If the flourene is not brominated prior to alkylation, the dialkylated fluorene is then brominated.
    Type: Grant
    Filed: December 19, 2002
    Date of Patent: September 5, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Timothy J. Adaway, Michael A. Gonzalez, Weishi Wu
  • 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: 6933417
    Abstract: A process for producing vinyl chloride monomer from ethylene and ethane having input of significant quantities of both ethane and ethylene in input streams to the affiliated reactor where hydrogen chloride in the reactor effluent is only partially 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; cooling and condensing the reactor effluent stream; and separating the condensed raw product stream into vinyl chloride monomer and a reactor recycle stream.
    Type: Grant
    Filed: October 6, 2000
    Date of Patent: August 23, 2005
    Assignee: Dow Global Technologies Inc.
    Inventors: John P. Henley, Mark E. Jones, Daniel A. Hickman, Kenric A. Marshall, Daniel J. Reed, William D. Clarke, Michael M. Olken, Lee E. Walko
  • 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: 6881872
    Abstract: Less colored trans-1,3-dichloropropene and a process for producing it, are presented. A composition comprising cis-1,3-dichloropropene, trans-1,3-dichloropropene and C6 compounds, is subjected to a distillation step and to a step of reacting chlorine or bromine, to remove cis-1,3-dichloropropene as a low boiling component, and then the residue is distilled to remove the chlorinated C6 compounds as a high boiling component and to obtain trans-1,3-dichloropropene as a low boiling component.
    Type: Grant
    Filed: March 27, 2003
    Date of Patent: April 19, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Tomoko Matsumoto, Tateo Nakano, Yutaka Yokoyama
  • Patent number: 6835860
    Abstract: Iodohydroxylated olefins can be prepared by treating an olefin with an aqueous solution of an iodine monohalide selected from iodine monochloride and iodine monobromide.
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: December 28, 2004
    Assignee: Merck & Co., Inc.
    Inventors: Yongkui Sun, Thorsten Rosner
  • Patent number: 6825390
    Abstract: Propargyl bromide is effectively stabilized against shock or thermal decomposition by use therewith of an environmentally acceptable inert liquid solvent that forms an azeotrope with propargyl bromide.
    Type: Grant
    Filed: April 18, 2002
    Date of Patent: November 30, 2004
    Assignee: Albemarle Corporation
    Inventors: Robert C. Herndon, Jr., Robert H. Allen, Noel H. Brantley, Hassan Y. Elnagar, Ronny W. Lin, Ralph W. Magin, Mahmood Sabahi
  • Patent number: 6806396
    Abstract: The present invention relates to the co-pyrolysis of fluoroform and chlorodifluoromethane to form a mixture of useful fluoroolefin and saturated HFCs, notably, tetrafluoroethylene and hexafluoropropylene and CF3CHF2 and CF3CHFCF3, respectively.
    Type: Grant
    Filed: December 16, 2002
    Date of Patent: October 19, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Peter Gideon Gelblum, Velliyur Nott Mallikarjuna Rao, Charles Joseph Noelke, Norman Herron
  • 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: 6794551
    Abstract: This invention provides a process of producing propargyl bromide in the absence of a base. The process comprises: A) bringing together in a reaction zone under an inert atmosphere and in the absence of a base and in the presence of an inert diluent, a feed of phosphorus tribromide and a separate feed of propargyl alcohol thereby forming a reaction mixture; B) while mechanically agitating the mixture being formed in A), maintaining the temperature of the mixture in the range of about 0° C. to about 25° C. to form a product mixture, and then C) raising the temperature of the product mixture to a temperature in the range of about 40° C. to about 60° C. while stirring the product mixture for a ride period of at least about 2.5 hours. Such process can be conducted as a batch process, as a semi-batch process, or as a continuous process.
    Type: Grant
    Filed: August 30, 2002
    Date of Patent: September 21, 2004
    Assignee: Albemarle Corporation
    Inventors: Christopher L. Mero, Hassan Y. Elnager, Robert C. Herndon, Jr.
  • Patent number: 6774270
    Abstract: A method of removing hexafluoropropylene dimers (“HFP dimers”), dimer hydrides and other oligomers from a fluid is described. The method comprises heating the fluid to isomerize the HFP dimers to the thermodynamic isomer, and contacting the fluid with a tertiary amine (or salts thereof) to form a hexafluoropropylene dimer—tertiary amine adduct. The method may further comprise the step of separating the dimer adducts from the reaction mixture.
    Type: Grant
    Filed: April 1, 2003
    Date of Patent: August 10, 2004
    Assignee: 3M Innovative Properties Company
    Inventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
  • Publication number: 20030164284
    Abstract: Less colored trans-1,3-dichloropropene and a process for producing it, are presented.
    Type: Application
    Filed: March 27, 2003
    Publication date: September 4, 2003
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventors: Tomoko Matsumoto, Tateo Nakano, Yutaka Yokoyama
  • Publication number: 20020035303
    Abstract: Sample processing methods that utilize a graphitised carbon matrix are useful for determining the relative amounts polyhalogenated biphenyis (PHBs), polyhalogenated dibenzofurans (PHDFs), and polyhalogenated dibenzo-p-dioxins (PHDDs) in a mixture of polyhalogenated diaromatic hydrocarbons (PHDHs). The methods are particularly useful when used in conjunction with cell-based assays for determining the toxicity of PHDH compounds.
    Type: Application
    Filed: June 1, 2001
    Publication date: March 21, 2002
    Inventors: Michael D. Chu, George C. Clark
  • Patent number: 5912371
    Abstract: A method for preparing fatty acid chlorides. The method comprises reacting a silylation product of a fatty acid comprising at 1east 2 aliphatically unsaturated bonds per molecule and a chlorinating agent.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: June 15, 1999
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventors: Koji Nakanishi, Tadashi Okawa
  • Patent number: 5750065
    Abstract: A method for producing biosorbents for adsorption of PCB's in which at least one proteinaceous material is contacted with a molar excess of at least one PCB congener mixture, forming a protein/PCB congener mixture. The protein/PCB congener mixture is dried after which the PCB congeners are extracted from the dried protein/PCB congener mixture forming a biosorbent in the form of an imprinted protein.
    Type: Grant
    Filed: January 25, 1993
    Date of Patent: May 12, 1998
    Assignee: Institute of Gas Technology
    Inventor: John J. Kilbane, II
  • 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: 5689020
    Abstract: A process is disclosed for preparing a compound selected from the group consisting of 1,1,3,3-tetrachloropropene and 1,3,3,3-tetrachloropropene. The process comprisesa. admixing a hydrocarbon compound selected from the group consisting of propene, 1-chloropropene, 3-chloropropene, 1,1-dichloropropene, 1,3-dichloropropene, 3,3,-dichloropropene, 1,1-dichloropropane, 11,2-dichloropropane, 1,3-dichloropropane, 1,1,3-trichloropropene, 1,3,3-trichloropropene, 3,3,3-trichloropropene, and mixtures thereof with an inert diluent gas;b. preheating said mixture to from about 300.degree. C. to about 400.degree. C. and then mixing it with chlorine gas; andc. thermally treating the mixture of step b. at a temperature of from about 400.degree. C. to about 600.degree. C.The desired tetrachloropropene is then separated.
    Type: Grant
    Filed: March 11, 1996
    Date of Patent: November 18, 1997
    Assignee: LaRoche Industries Inc.
    Inventor: C. Bradford Boyce