Preparing By Addition Of Elemental Halogen, Interhalogen Compound, Or Hydrogen Halide To Carbon To Carbon Unsaturation Patents (Class 570/246)
  • Patent number: 8952209
    Abstract: A method and apparatus for method of continuously producing 1,1,1,2,3-pentafluoropropane with high yield is provided. The method includes (a) bringing a CoF3-containing cobalt fluoride in a reactor into contact with 3,3,3-trifluoropropene to produce a CoF2-containing cobalt fluoride and 1,1,1,2,3-pentafluoropropane, (b) transferring the CoF2-containing cobalt fluoride in the reactor to a regenerator and bringing the transferred CoF2-containing cobalt fluoride into contact with fluorine gas to regenerate a CoF3-containing cobalt fluoride, and (c) transferring the CoF3-containing cobalt fluoride in the regenerator to the reactor and employing the transferred CoF3-containing cobalt fluoride in Operation (a). Accordingly, the 1,1,1,2,3-pentafluoropropane can be continuously produced with high yield from the 3,3,3-trifluoropropene using a cobalt fluoride (CoF2/CoF3) as a fluid catalyst, thereby improving the reaction stability and readily adjusting the optimum conversion rate and selectivity.
    Type: Grant
    Filed: March 13, 2013
    Date of Patent: February 10, 2015
    Assignee: Foosung Co., Ltd.
    Inventors: ook jae Cho, Jae Kug Ryu, Bong Seok Kim, Donghyun Kim, Byounghun Park, su jin Park, Jin-A Jung, Daewoo Kim
  • Patent number: 8921624
    Abstract: A process for the production of an aliphatic bromide in which the bromine atom is attached to a terminal carbon atom, which process comprises continuously feeding olefin having a terminal double bond, gaseous hydrogen bromide, and a molecular oxygen-containing gas into a liquid phase reaction medium comprised of aliphatic bromide to cause anti-Markovnikov addition of HBr to terminal olefin, the feeds being proportioned and maintained to provide a molar excess of hydrogen bromide relative to terminal olefin in the range of about 1 to about 5 percent, and a molar ratio of molecular oxygen to terminal olefin of less than 0.005. The process is especially suited for production of n-propyl bromide.
    Type: Grant
    Filed: April 11, 2007
    Date of Patent: December 30, 2014
    Assignee: Albemarle Corporation
    Inventors: James E. Torres, Alvin E. Harkins, Jr., Thanikavelu Manimaran, B. Gary McKinnie
  • Patent number: 8877990
    Abstract: A process of making a chlorinated hydrocarbon through a thermal dehydrochlorination step in which an unsaturated compound represented by the following general formula (2) is obtained by thermally decomposing a saturated compound represented by the following general formula (1). CCl3—CCl2-mHm—CCl3-nHn??(1) CCl2?CCl2-mHm-1—CCl3-nHn??(2) (in the above formulas, m is 1 or 2, and n is an integer of 0 to 3.
    Type: Grant
    Filed: June 17, 2010
    Date of Patent: November 4, 2014
    Assignee: Tokuyama Corporation
    Inventors: Tadahiro Fukuju, Kikuo Yamamoto, Masayuki Moriwaki, Yasutaka Komatsu, Akihiro Saito, Shunsuke Hosaka, Dai Tsunoda, Jun Kawakami
  • Patent number: 8859762
    Abstract: Chlorinated aromatic compounds are prepared by ultrasonicating a mixture of ICl and an aromatic compound.
    Type: Grant
    Filed: November 26, 2010
    Date of Patent: October 14, 2014
    Assignee: Peking University
    Inventors: Yu Wei, Xiangyun Wang
  • Patent number: 8822741
    Abstract: A process for the fluorination of haloolefins with elemental fluorine in the presence of anhydrous HF proceeds with high yield and selectivity in the product deriving from the addition of fluorine to the carbon-carbon double bond.
    Type: Grant
    Filed: July 5, 2011
    Date of Patent: September 2, 2014
    Assignee: Solvay Specialty Polymers Italy S.p.A.
    Inventors: Vito Tortelli, Marco Galimberti
  • Patent number: 8754273
    Abstract: Disclosed is a process for making the compound 1,1,2-trichloro-3,3,3-trifluoropropane (233da) by the catalytic fluorination of 1,1,1,2,3,3-hexachloropropane. 233da is a starting material used in the production cis-1-chloro-3,3,3-trifluoropropene (cis-1233zd).
    Type: Grant
    Filed: November 12, 2012
    Date of Patent: June 17, 2014
    Assignee: Honeywell International Inc.
    Inventors: Yian Zhai, Andrew Joseph Poss, Rajiv Ratna Singh
  • Publication number: 20140005349
    Abstract: The present invention generally relates to alcohol-terminated polyisobutylene (PIB) compounds, and to a process for making such compounds. In one embodiment, the present invention relates to primary alcohol-terminated polyisobutylene compounds, and to a process for making such compounds. In still another embodiment, the present invention relates to polyisobutylene compounds that can be used to synthesize polyurethanes, to polyurethane compounds made via the use of such polyisobutylene compounds, and to processes for making such compounds. In yet another embodiment, the present invention relates to primary alcohol-terminated polyisobutylene compounds having two or more primary alcohol termini and to a process for making such compounds. In yet another embodiment, the present invention relates to primary terminated polyisobutylene compounds having two or more primary termini selected from amine groups or methacrylate groups.
    Type: Application
    Filed: September 4, 2013
    Publication date: January 2, 2014
    Applicant: The University of Akron
    Inventors: Joseph P. Kennedy, Yongmoon Kwon, Subramanyam Ummadisetty
  • 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: 8304589
    Abstract: A process of making a chlorinated hydrocarbon through a thermal dehydrochlorination step in which an unsaturated compound represented by the following general formula (2) is obtained by thermally decomposing a saturated compound represented by the following general formula (1). CCl3—CCl2-mHm—CCl3-nHn??(1) CCl2?CCl2-mHm-1—CCl3-nHn??(2) (in the above formulas, m is 1 or 2, and n is an integer of 0 to 3.).
    Type: Grant
    Filed: February 27, 2012
    Date of Patent: November 6, 2012
    Assignee: Tokuyama Corporation
    Inventors: Tadahiro Fukuju, Kikuo Yamamoto, Masayuki Moriwaki, Yasutaka Komatsu, Akihiro Saito, Shunsuke Hosaka, Dai Tsunoda, Jun Kawakami
  • 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
  • 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
  • Patent number: 8026085
    Abstract: A method and system for selectively fluorinating organic molecules on a target site wherein the target site is activated and then fluorinated are shown together with a method and system for identifying a molecule having a biological activity.
    Type: Grant
    Filed: August 4, 2007
    Date of Patent: September 27, 2011
    Assignee: California Institute of Technology
    Inventors: Rudi Fasan, Frances H. Arnold
  • Patent number: 7943099
    Abstract: A reactor for reacting at least two gases in the presence of a liquid phase, provided with an external liquid phase circulation device and including at least one injector for injecting the gases and the externally circulated liquid phase. In the injector the mixing of the gases together and with the externally circulated liquid phase only begins at the outlet of the injector.
    Type: Grant
    Filed: November 18, 2005
    Date of Patent: May 17, 2011
    Assignee: SOLVAY (Societe Anonyme)
    Inventors: Michel Strebelle, Michel Lempereur
  • 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: 20110077366
    Abstract: Process for the manufacture of at least one ethylene derivative compound starting from a low value residual gas, preferably a refinery off-gas (ROG), according to which: a) the low value residual gas is subjected to a series of treatment steps in a low value residual gas recovery unit in order to remove the undesirable components present therein and to obtain a mixture of products containing ethylene and other constituents; b) the mixture of products is fractionated in one fractionation step into one fraction A containing almost all the ethylene, optionally into one individual fraction of ethane, and into one heavy fraction C; and c) the fraction A is conveyed to the manufacture of at least one ethylene derivative compound.
    Type: Application
    Filed: May 29, 2009
    Publication date: March 31, 2011
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Andre Petitjean, Michel Lempereur, Dominique Balthasart, Michel Strebelle
  • Patent number: 7842264
    Abstract: A multiple stage apparatus and process using aerodynamic reactors and aero-coalescers in sequence for the selective capture and removal of purified carbon dioxide gas, the sequential capture and removal of mercury, metal and particulate aerosols by a recycling chemical generation-regeneration system using alkali metal chloride solution following multiple oxidations of mercury vapor, and nitric oxide in sequence, selective capture and removal of sulfur dioxide and nitrogen dioxide by two stage absorption by a recycling chemical generation-regeneration system using alkali metal hydroxide-carbonate-bicarbonate solution together with sequential oxidation to alkali metal sulfate and alkali metal nitrate compounds through evaporation and crystallization. Carbon dioxide capture and recovery is achieved in sequence by selective thermal decarbonation from an alkaline liquid followed by recovery as a purified gas stream.
    Type: Grant
    Filed: April 2, 2008
    Date of Patent: November 30, 2010
    Assignee: Cefco, LLC
    Inventors: Hal B. H. Cooper, Robert E. Tang, Donald E. Degling, Thomas K. Ewan, Sam M. Ewan
  • Patent number: 7741524
    Abstract: Process for preparing one or more iodinated organic substances having a molecular mass of less than 2000 (substances (S)) using (A) at least one free-radical-generating substance chosen from peroxides, diazo compounds, dialkyldiphenylalkanes, substances derived from tetraphenylethane, boranes and iniferter substances comprising at least one thiuram disulphide group, (B) an ethylenically unsaturated substance capable of adding a free radical to its ethylenic double bond, (C) molecular iodine, which comprises the steps according to which at least a fraction of (A), at least a fraction of (B) and at least a fraction of (C) are introduced into a reactor, and then the contents of the reactor are caused to react, while introducing therein the possible remainder of (A), the possible remainder of (B) and the possible remainder of (C), until a moment is reached when the content of the reactor is a mixture comprising one or more substances (S).
    Type: Grant
    Filed: April 22, 2004
    Date of Patent: June 22, 2010
    Assignee: Solvay (Societe Anonyme)
    Inventors: Patrick Lacroix-Desmazes, Romain Severac, Bernard Boutevin, Vincent Bodart, Vincent Kurowski
  • 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: 7671243
    Abstract: The invention relates to a method for using reaction heat produced by reaction during the production of 1,2-dichloroethane from ethylene and chlorine in a direct chlorination reactor. The chlorine is produced in a sodium chloride electrolysis and the reaction heat, during the formation of 1,2-dichloroethane is used at least partially for the evaporation of NaOH, which is produced during NaCl-electrolysis for producing the required chlorine for direct chlorination, as a coupling product. The invention also relates to a device for carrying out said method, comprising a multi-tube heat exchanger comprising two fixed tubular plates and a NaOH-liquid phase part, and the caustic soda passes through the inside of the tube and 1,2-dichloroethane passes the outside of the tube. The heat exchanger also comprises devices for feeding and distributing the caustic soda in the inside of the tube.
    Type: Grant
    Filed: June 27, 2006
    Date of Patent: March 2, 2010
    Assignees: Uhde GmbH, Vinnolit GmbH & Co. KG
    Inventors: Sven Petersen, Michael Benje, Peter Kammerhofer
  • Patent number: 7671244
    Abstract: The invention relates to a method for producing high-purity 1,2-dichloroethane from dissolved chlorine and dissolved ethylene which are brought into contact with each other using a circulating liquid reaction medium which essentially consists of 1,2-dichloroethane and a catalyst and passes through at least one reaction loop. The two limbs of the loop are connected to a gas-phase stripping container which is arranged at the top and from which the reaction product is outwardly transferred either in a gaseous or liquid form or both in a gaseous form and in a liquid form. The addition points for the addition of chlorine and dissolved ethylene are arranged in the limb of the loop in which the liquid rises. The addition point for dissolved chlorine is always arranged downstream of the ethylene addition point.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: March 2, 2010
    Assignee: UHDE GmbH
    Inventors: Harald Hafenscher, Reinhold Weis, Michael Benje
  • Publication number: 20100010256
    Abstract: Processes which include: (a) providing a gas phase comprising hydrogen chloride; (b) oxidizing the hydrogen chloride in a reactor to form a product gas comprising chlorine, unreacted hydrogen chloride and water, the reactor having structural parts with inner surfaces that are contacted during oxidation by one or both of the gas phase and the product gas; (c) cooling the process gas; (d) separating the unreacted hydrogen chloride and water from the product gas; (e) drying the product gas; and (f) separating the chlorine from the product gas; wherein the inner surfaces of the reactor structural parts that are contacted during oxidation by one or both of the gas phase and the product gas are comprised of a nickel material having a nickel content of at least 60 wt. %, are described.
    Type: Application
    Filed: July 8, 2009
    Publication date: January 14, 2010
    Applicant: Bayer MaterialScience AG
    Inventors: Andreas Bulan, Helmut Diekmann, Gerhard Ruffert, Kaspar Hallenberger
  • Publication number: 20090306439
    Abstract: The invention relates to a method for using reaction heat produced by reaction during the production of 1,2-dichloroethane from ethylene and chlorine in a direct chlorination reactor. The chlorine is produced in a sodium chloride electrolysis and the reaction heat, during the formation of 1,2-dichloroethane is used at least partially for the evaporation of NaOH, which is produced during NaCl-electrolysis for producing the required chlorine for direct chlorination, as a coupling product. The invention also relates to a device for carrying out said method, comprising a multi-tube heat exchanger comprising two fixed tubular plates and a NaOH-liquid phase part, and the caustic soda passes through the inside of the tube and 1,2-dichloroethane passes the outside of the tube. The heat exchanger also comprises devices for feeding and distributing the caustic soda in the inside of the tube.
    Type: Application
    Filed: June 27, 2006
    Publication date: December 10, 2009
    Inventors: Sven Petersen, Michael Benje, Peter Kammerhofer
  • Patent number: 7579509
    Abstract: The invention refers to a process for the production of high-purity 1,2-dichloroethane from dissolved chlorine and dissolved ethylene, which are brought into contact with each other in a circulating liquid reaction fluid, which mainly consists of 1,2-dichlorethane and a catalyst and flows through at least one vertically arranged loop-type reaction section, both legs of the loop being connected to an overhead degassing vessel from where the reaction product is withdrawn either in gaseous or in liquid state or in both gaseous and liquid state, and numerous admixing sections being arranged in the leg of the loop in which the liquid rises, and each of these admixing sections having one upstream feed point for dissolved or gaseous ethylene and one downstream feed point for dissolved chlorine and, if required, the admixing sections featuring static mixers.
    Type: Grant
    Filed: June 15, 2005
    Date of Patent: August 25, 2009
    Assignees: Uhde GmbH, Vinnolit GmbH & Co. KG
    Inventors: Michael Benje, Harald Hafenscher
  • Publication number: 20090163746
    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: Application
    Filed: December 16, 2008
    Publication date: June 25, 2009
    Inventor: TERRY WAYNE REDWINE
  • Publication number: 20090054709
    Abstract: A process for the production of an aliphatic bromide in which the bromine atom is attached to a terminal carbon atom, which process comprises continuously feeding olefin having a terminal double bond, gaseous hydrogen bromide, and a molecular oxygen-containing gas into a liquid phase reaction medium comprised of aliphatic bromide to cause anti-Markovnikov addition of HBr to terminal olefin, the feeds being proportioned and maintained to provide a molar excess of hydrogen bromide relative to terminal olefin in the range of about 1 to about 5 percent, and a molar ratio of molecular oxygen to terminal olefin of less than 0.005. The process is especially suited for production of n-propyl bromide.
    Type: Application
    Filed: April 11, 2007
    Publication date: February 26, 2009
    Applicant: ALBEMARLE CORPORATION
    Inventors: James E. Torres, Alvin E. Harkins, JR., Thanikavelu Manimaran, B. Gary McKinnie
  • Patent number: 7348461
    Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.
    Type: Grant
    Filed: October 31, 2003
    Date of Patent: March 25, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
  • Patent number: 7217849
    Abstract: A method is described for producing n-propyl bromide of a high degree of purity, which contains isopropyl bromide in an amount lower than 0.1% w/w, and usually lower than 0.05%. The method is characterized in that n-propanol is reacted with HBr which is in gas form, preferably dry, and which is in excess over the stoichiometric amount, wherein the excess HBr is at the end of the reaction in an aqueous solution formed from the reaction water. The invention further relates to N-propyl bromide of high purity, containing typically less than 500 ppm of isopropyl bromide.
    Type: Grant
    Filed: November 11, 2002
    Date of Patent: May 15, 2007
    Assignee: Bromine Compounds Ltd.
    Inventors: Aharon Meirom, Arieh Kampf, Dmitri Grinberg, Sarina Grinberg, legal representative, Mark Grinberg, deceased
  • Patent number: 7182840
    Abstract: The invention relates to a method and a device for the optimal use of reaction heat resulting from the production of 1,2-dichloroethane from ethene and chlorine. The aim of the invention is achieved by extracting reaction heat liberated during the reaction of chlorine with ethene and the reaction heat contained in 1,2-dichloroethane. Extraction of said reaction heat from the reaction chamber occurs using at least one part of gaseous 1,2-dichloroethane (latent heat) and at least one part of liquid 1,2-dichloroethane (feelable heat) removed from the reaction chamber. Said reaction heat is used to heat two fractioning columns in order to purify 1,2-dichloroethane of impurities having a boiling point higher than 1,2-dichloroethane.
    Type: Grant
    Filed: October 28, 2000
    Date of Patent: February 27, 2007
    Assignee: UHDE GmbH
    Inventors: Michael Benje, Peter Porscha, Stefan Von Egelstein
  • Patent number: 7132578
    Abstract: A process for the preparation of trifluoromethyl iodide is provided. The process includes the step of contacting in a reactor a compound represented by the formula: CF3—W and a compound represented by the formula: IFn wherein W can be H, Br, Cl, COOH, COCl, COOCH3, COOC2H5, COCH3, COPh, CF3, Si(CH3)3, SPh, SCH3, SSCF3, SSPh, SSCH3, or SO2Cl, wherein n is 1, 3, 5, or 7, and wherein the step of contacting is carried out, at a temperature, pressure and for a length of time sufficient to produce trifluoromethyl iodide. The contacting step can be carried out in the presence or absence of a catalyst and the contacting step can be carried out in the presence or absence of air.
    Type: Grant
    Filed: July 14, 2005
    Date of Patent: November 7, 2006
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Hsueh Sung Tung
  • 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: 7094936
    Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: August 22, 2006
    Assignee: Great Lakes Chemical Corporation
    Inventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
  • Patent number: 7009084
    Abstract: The invention relates to a method for producing high purity 1,2-dichloroethane using a liquid reaction medium that is circulated and that is essentially composed of 1,2-dichloroethane and a catalyst. At least ethylene and chlorine are added to the reaction medium and a mainly chlorine-containing gas flow is dissolved in a part of the reaction medium which is essentially devoid of dissolved ethylene. The gaseous components not dissolved in this solution are removed from the solution by means of a gas-separation device and the solution from which the undissolved gas components were removed is contacted with ethylene which is present in dissolved form.
    Type: Grant
    Filed: February 1, 2003
    Date of Patent: March 7, 2006
    Assignees: Uhde GmbH, Vinnolit Technologie GmbH & Co. KG
    Inventors: Michael Benje, Dieter Jaculi, Ingolf Mielke, Peter Schwarzmaier, Klaus Krejci, Joachim Schubert, Horst Ertl
  • Patent number: 6977316
    Abstract: A catalytic one-step process for the production of CF3I by reacting, preferably in the presence of a source of oxygen, a source of iodine with a reactant of the formula: CF3R where R is —SH, —S—S—CF3, —S-phenyl, or —S—Si—(CH3)3. The catalyst may be a metal salt such as salts of Cu, Hg, Pt, Pd, Co, Mn, Rh, Ni, V, TI, Ba, Cs, Ca, K and Ge and mixtures thereof, preferably on a support such as MgO, BaO and CaO, BaCO3, CsNO3, Ba (NO3)2, activated carbon, basic alumina, and ZrO2.
    Type: Grant
    Filed: December 8, 2004
    Date of Patent: December 20, 2005
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, HsuehSung Tung
  • Patent number: 6841708
    Abstract: With a method or a device for producing 1,2-dichloroethane or ethylene (di)chloride (EDC) with the use of a circulating reaction medium and a catalyst, whereby ethylene and chlorine are supplied to the reaction medium, the goal is to permit the catalytic chlorination of ethylene in a manner that is particularly gentle to the product. This is achieved in terms of the method and by other means in that the ethylene or chlorine gas are introduced into the reaction medium by means of microporous gas diffuser elements for producing gas bubbles with a diameter of 0.3 to 3 mm.
    Type: Grant
    Filed: October 12, 1999
    Date of Patent: January 11, 2005
    Assignees: Vinnolit Technologie GmbH & Co., Uhde GmbH
    Inventor: Michael Benje
  • 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: 6756513
    Abstract: Monochlorinated hydrocarbons of high isomeric purity are prepared by a process, which comprises: reacting a monoalcohol having an alkyl radical having from 3 to 20 carbon atoms with cyanuric chloride; and purifying the resulting monochlorinated hydrocarbon by distillation after separation of salts and washing the monochlorinated hydrocarbon with alkali. The invention relates to a process for preparing monochlorinated hydrocarbons which contain an alkyl radical having from 3 to 20 carbon atoms and have a high isomeric purity by reacting a monoalcohol having a hydrocarbon radical containing an alkyl radical having from 3 to 20 carbon atoms to which additional cycloaliphatic radicals, aryl radicals, aralkyl radicals and alkylaryl radicals may be bound with cyanuric chloride, separating off salts, washing the reaction mixture with alkali and purifying the resulting monochlorinated hydrocarbons by distillation.
    Type: Grant
    Filed: August 16, 2002
    Date of Patent: June 29, 2004
    Assignee: Degussa AG
    Inventors: Manfred Neumann, Clemens Osterholt
  • Patent number: 6740253
    Abstract: The present invention relates to a non-hazardous brominating reagent from an aqueous alkaline bromine byproduct solution obtained from bromine recovery plant and containing 25 to 35% bromine dissolved in aqueous lime or sodium hydroxide containing alkali bromide and alkali bromate mixture having bromide to bromate stoichiometric ratio in the range of 5:1 to 5.1:1 or 2:1 to 2.1:1 and a pH ranging between 8-12 and also relates to a method for borminating aromatic compounds by using the above brominating agent.
    Type: Grant
    Filed: January 23, 2002
    Date of Patent: May 25, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Rajinder Nath Vohra, Pushpito Kumar Ghosh, Maheshkumar Ramniklal Gandhi, Himanshu Labhshanker Joshi, Hasina Hajibhai Deraiya, Rohit Harshadray Dave, Koushik Halder, Kishorkumar Manmohandas Majeethia, Sohan Lal Daga, Vadakke Puthoor Mohandas, Rahul Jasvantrai Sanghavi
  • Patent number: 6693224
    Abstract: The invention relates to a method for the production of 1,2-dichloroethane by direct chlorination using chlorine and ethene in which, despite low reaction temperatures during direct chlorination, reaction heat produced is nevertheless used. According to the invention, vaporous 1,2-dichloroethane obtained in the direct chlorination reactor is compressed and the compressed 1,2-dichloroethane is transported to heat exchangers whereby heat is given off by the 1,2-dichloroethane. The invention also relates to a device including a turbocompressor arranged directly after the direct chlorination reactor.
    Type: Grant
    Filed: May 22, 2002
    Date of Patent: February 17, 2004
    Assignee: Uhde GmbH
    Inventor: Joachim Motz
  • Patent number: 6506952
    Abstract: Hexabromocyclododecane with enhanced gamma isomer content is produced by brominating cyclododecatriene in a liquid medium comprised of (1) at least 50 wt % of at least one liquid inert organic solvent other than 1,4-dioxane having a solubility in water of at least 1 wt % at 25° C., and (2) water in an amount of up to about 40 wt %, in the presence of (3) about 0.5 to about 30 wt % of bromide ion (Br−), each wt % being based on the total weight of the liquid portion of the liquid medium.
    Type: Grant
    Filed: October 18, 2001
    Date of Patent: January 14, 2003
    Assignee: Albemarle Corporation
    Inventor: John K. Kendall
  • Patent number: 6420617
    Abstract: This invention relates to the production of an hexabromocyclododecane product, which process comprises brominating cyclododecatriene in the presence of a 1,4-dioxane and water based solvent and from about 0.5 to about 30 wt % bromide ion in the liquid phase of the reaction mass. Optional post-reaction heat treatment in a finishing step increases process yields if needed. The hexabromocyclododecane product is unrecrystallized and contains no more than about 1.5 wt % tetrabromocyclododecene impurities.
    Type: Grant
    Filed: June 8, 2001
    Date of Patent: July 16, 2002
    Assignee: Albemarle Corporation
    Inventors: John K. Kendall, Jeffrey T. Aplin
  • Patent number: 6284935
    Abstract: This invention relates to the production of an hexabromocyclododecane product, which process comprises brominating cyclododecatriene in the presence of a 1,4-dioxane and water based solvent and from about 0.5 to about 30 wt % bromide ion in the liquid phase of the reaction mass. Optional post-reaction heat treatment in a finishing step increases process yields if needed. The hexabromocyclododecane product is unrecrystallized and contains no more than about 1.5 wt % tetrabromocyclododecene impurities.
    Type: Grant
    Filed: August 18, 1999
    Date of Patent: September 4, 2001
    Assignee: Albemarle Corporation
    Inventors: John K. Kendall, Jeffrey T. Aplin
  • Patent number: 6252125
    Abstract: By a process for the production of 1,2-dichloroethane (EDC) by reaction of ethylene with chlorine in the liquid phase (direct chlorination), the heavy ends being separated from the obtained 1,2-dichloroethane in a heavy-ends column and in a downstream vacuum column and, for the purpose of heat recovery and heating of the column bottoms, a 1,2-dichloroethane part-stream from the direct chlorination passing through a heat exchanger (one attributed to each column) for indirect heat exchange with the bottom product of each column, the aim of the invention is to provide a solution in which the reaction enthalpy of the direct chlorination can be used in a variable manner, thus precluding the above-described disadvantages. This is achieved by using at least one falling-film evaporator for heating the column bottoms, the bottom product of the respective column being routed to the distributor at the head of the column.
    Type: Grant
    Filed: April 14, 2000
    Date of Patent: June 26, 2001
    Assignee: Krupp Uhde GmbH
    Inventor: Peter Porscha
  • Patent number: 6235953
    Abstract: The preparation of 1,2-dichloroethane (EDC) is carried out by feeding ethylene and chlorine into circulating EDC (direct chlorination) such that the reaction mixture boils and the heat of the reaction is led away from the gas space.
    Type: Grant
    Filed: August 23, 1999
    Date of Patent: May 22, 2001
    Assignee: Vinnolit Monomer GmbH & Co. KG
    Inventors: Peter Schwarzmaier, Ingolf Mielke
  • Patent number: 5986152
    Abstract: A supported catalyst includes: a) 0.5-15 wt. % of one or more Cu-II compounds, the quantitative amounts referring to copper metal; b) 0.1-8 wt. % of one or more alkali metal compounds, the quantitative amounts referring to alkali metal; c) 0.1-10 wt. % of an oxide mixture including; c1) 80-95 mole % of oxides of cerite rare earths with atomic Nos. 57 to 62, except promethium, and c2) 5-20 mole % of zirconium dioxide, where c1) and c2) must together total 100 mole % and the quantitative amount of c) refers to the oxides of the mixture, and d) the remainder up to 100 wt. % being .gamma. and/or .alpha.-aluminum oxide as support material, wherein e) the support material d) has a total pore volume in the range from 0.65 to 1.2 cm.sup.3 /g, and wherein f) the supported catalyst is present in the form of cylindrical hollow bodies having at least one passage channel, the ratio of height h to external diameter d.sup.e being less than 1.5 for diameters d.sub.e of up to 6 mm, and the ratio h/d.sub.e being less than 0.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: November 16, 1999
    Assignee: Degussa-Huls AG
    Inventors: Herbert Muller, Stefan Bosing, Ludwig Schmidhammer, Albin Frank, Klaus Haselwarter
  • Patent number: 5905177
    Abstract: In a method for producing 1,2-dichloroethane by an oxychlorination reaction of ethylene, hydrogen chloride and oxygen, a continuous method for producing 1,2-dichloroethane, which comprises cooling a gas discharged from an oxychlorination reactor to condense and separate 1,2-dichloroethane and water therefrom, further removing hydrogen chloride and carbon dioxide therefrom, then mixing oxygen and nitrogen thereto so that the oxygen concentration becomes from 20 to 30 vol % and the ethylene concentration becomes from 1 to 3 vol % and supplying the gas mixture thus adjusted to an oxychlorination reactor.
    Type: Grant
    Filed: March 15, 1996
    Date of Patent: May 18, 1999
    Assignee: Toshoh Corporation
    Inventors: Ikuya Seo, Terumasa Yoshida
  • Patent number: 5866732
    Abstract: Alkyl bromides are prepared from mixtures comprising aqueous hydrobromic acid and olefins in a process in which there is concentration of the aqueous hydrobromic acid present during the reaction.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: February 2, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Eiermann, Klaus Ebel
  • Patent number: 5831137
    Abstract: In the continuous preparation of alkyl halides from branched olefins and hydrohalic acids, the reaction is carried out without the addition of catalysts and without solvents. With a high olefin conversion, alkyl halides are obtained with high selectivity and with very good color quality.
    Type: Grant
    Filed: February 10, 1997
    Date of Patent: November 3, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Josef Metz, Clemens Osterholt
  • Patent number: 5773673
    Abstract: Disclosed is a method of making chlorinated hydrocarbons. A mixture is prepared of a hydrocarbon or partially chlorinated hydrocarbon from C.sub.18 to C.sub.30 and either benzotrifluoride or parachlorobenzotrifluoride in an amount sufficient to liquefy the mixture at the chlorination temperature. The mixture is heated to a temperature of about 50.degree. to 100.degree. C. and sufficient chlorine gas is passed therethrough in the presence of UV light to form a chlorinated hydrocarbon that is about 60 to about 80 wt. % chlorine. One part by weight of the composition is added to at least two parts by weight per part of a C.sub.1 to C.sub.6 monohydric alcohol, which results in the precipitation of the chlorinated hydrocarbon. The precipitated chlorinated hydrocarbon can be removed from the composition by, for example, filtration.
    Type: Grant
    Filed: July 1, 1997
    Date of Patent: June 30, 1998
    Assignee: Occidental Chemical Corporation
    Inventors: Pravin M. Khandare, Edward A. Rowe
  • Patent number: 5527975
    Abstract: Bromochloro-alkanes are made by reaction of a corresponding chloroalkene with hydrogen bromide by a continuous process carried at -20.degree. to +20.degree. C., preferably in a gas-lift reactor.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: June 18, 1996
    Assignee: Albemarle Corporation
    Inventors: Dominique Cosserat, Francois Stutz