Preparing By Addition Of Elemental Halogen, Interhalogen Compound, Or Hydrogen Halide To Carbon To Carbon Unsaturation Patents (Class 570/246)
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Patent number: 8952209Abstract: 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: GrantFiled: March 13, 2013Date of Patent: February 10, 2015Assignee: 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
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Patent number: 8921624Abstract: 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: GrantFiled: April 11, 2007Date of Patent: December 30, 2014Assignee: Albemarle CorporationInventors: James E. Torres, Alvin E. Harkins, Jr., Thanikavelu Manimaran, B. Gary McKinnie
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Patent number: 8877990Abstract: 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: GrantFiled: June 17, 2010Date of Patent: November 4, 2014Assignee: Tokuyama CorporationInventors: Tadahiro Fukuju, Kikuo Yamamoto, Masayuki Moriwaki, Yasutaka Komatsu, Akihiro Saito, Shunsuke Hosaka, Dai Tsunoda, Jun Kawakami
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Patent number: 8859762Abstract: Chlorinated aromatic compounds are prepared by ultrasonicating a mixture of ICl and an aromatic compound.Type: GrantFiled: November 26, 2010Date of Patent: October 14, 2014Assignee: Peking UniversityInventors: Yu Wei, Xiangyun Wang
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Patent number: 8822741Abstract: 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: GrantFiled: July 5, 2011Date of Patent: September 2, 2014Assignee: Solvay Specialty Polymers Italy S.p.A.Inventors: Vito Tortelli, Marco Galimberti
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Patent number: 8754273Abstract: 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: GrantFiled: November 12, 2012Date of Patent: June 17, 2014Assignee: Honeywell International Inc.Inventors: Yian Zhai, Andrew Joseph Poss, Rajiv Ratna Singh
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Publication number: 20140005349Abstract: 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: ApplicationFiled: September 4, 2013Publication date: January 2, 2014Applicant: The University of AkronInventors: Joseph P. Kennedy, Yongmoon Kwon, Subramanyam Ummadisetty
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Publication number: 20130172191Abstract: 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: ApplicationFiled: February 25, 2013Publication date: July 4, 2013Inventors: Richard Martin Jacobson, Martha Jean Kelly, William Nixon James
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Patent number: 8304589Abstract: 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: GrantFiled: February 27, 2012Date of Patent: November 6, 2012Assignee: Tokuyama CorporationInventors: Tadahiro Fukuju, Kikuo Yamamoto, Masayuki Moriwaki, Yasutaka Komatsu, Akihiro Saito, Shunsuke Hosaka, Dai Tsunoda, Jun Kawakami
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Patent number: 8030531Abstract: 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: GrantFiled: December 16, 2008Date of Patent: October 4, 2011Assignee: Dupont Performance Elastomers LLCInventor: Terry Wayne Redwine
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Patent number: 8026400Abstract: 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: GrantFiled: December 16, 2008Date of Patent: September 27, 2011Assignee: Dupont Performance Elastomers LLCInventor: Terry Wayne Redwine
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Patent number: 8026085Abstract: 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: GrantFiled: August 4, 2007Date of Patent: September 27, 2011Assignee: California Institute of TechnologyInventors: Rudi Fasan, Frances H. Arnold
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Patent number: 7943099Abstract: 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: GrantFiled: November 18, 2005Date of Patent: May 17, 2011Assignee: SOLVAY (Societe Anonyme)Inventors: Michel Strebelle, Michel Lempereur
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Publication number: 20110082267Abstract: 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 theType: ApplicationFiled: May 29, 2009Publication date: April 7, 2011Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Michel Lempereur, Dominique Balthasart, Michel Strebelle, Massimo Giansante
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Publication number: 20110077366Abstract: 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: ApplicationFiled: May 29, 2009Publication date: March 31, 2011Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Andre Petitjean, Michel Lempereur, Dominique Balthasart, Michel Strebelle
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Patent number: 7842264Abstract: 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: GrantFiled: April 2, 2008Date of Patent: November 30, 2010Assignee: Cefco, LLCInventors: Hal B. H. Cooper, Robert E. Tang, Donald E. Degling, Thomas K. Ewan, Sam M. Ewan
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Patent number: 7741524Abstract: 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: GrantFiled: April 22, 2004Date of Patent: June 22, 2010Assignee: Solvay (Societe Anonyme)Inventors: Patrick Lacroix-Desmazes, Romain Severac, Bernard Boutevin, Vincent Bodart, Vincent Kurowski
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Patent number: 7691282Abstract: 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: GrantFiled: September 8, 2005Date of Patent: April 6, 2010Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Michael G. Costello
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Patent number: 7671243Abstract: 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: GrantFiled: June 27, 2006Date of Patent: March 2, 2010Assignees: Uhde GmbH, Vinnolit GmbH & Co. KGInventors: Sven Petersen, Michael Benje, Peter Kammerhofer
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Patent number: 7671244Abstract: 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: GrantFiled: December 15, 2005Date of Patent: March 2, 2010Assignee: UHDE GmbHInventors: Harald Hafenscher, Reinhold Weis, Michael Benje
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Publication number: 20100010256Abstract: 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: ApplicationFiled: July 8, 2009Publication date: January 14, 2010Applicant: Bayer MaterialScience AGInventors: Andreas Bulan, Helmut Diekmann, Gerhard Ruffert, Kaspar Hallenberger
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Publication number: 20090306439Abstract: 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: ApplicationFiled: June 27, 2006Publication date: December 10, 2009Inventors: Sven Petersen, Michael Benje, Peter Kammerhofer
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Patent number: 7579509Abstract: 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: GrantFiled: June 15, 2005Date of Patent: August 25, 2009Assignees: Uhde GmbH, Vinnolit GmbH & Co. KGInventors: Michael Benje, Harald Hafenscher
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Publication number: 20090163746Abstract: 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: ApplicationFiled: December 16, 2008Publication date: June 25, 2009Inventor: TERRY WAYNE REDWINE
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Publication number: 20090054709Abstract: 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: ApplicationFiled: April 11, 2007Publication date: February 26, 2009Applicant: ALBEMARLE CORPORATIONInventors: James E. Torres, Alvin E. Harkins, JR., Thanikavelu Manimaran, B. Gary McKinnie
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Patent number: 7348461Abstract: 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: GrantFiled: October 31, 2003Date of Patent: March 25, 2008Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
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Patent number: 7217849Abstract: 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: GrantFiled: November 11, 2002Date of Patent: May 15, 2007Assignee: Bromine Compounds Ltd.Inventors: Aharon Meirom, Arieh Kampf, Dmitri Grinberg, Sarina Grinberg, legal representative, Mark Grinberg, deceased
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Patent number: 7182840Abstract: 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: GrantFiled: October 28, 2000Date of Patent: February 27, 2007Assignee: UHDE GmbHInventors: Michael Benje, Peter Porscha, Stefan Von Egelstein
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Patent number: 7132578Abstract: 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: GrantFiled: July 14, 2005Date of Patent: November 7, 2006Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Hsueh Sung Tung
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Patent number: 7112709Abstract: 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: GrantFiled: September 9, 2003Date of Patent: September 26, 2006Assignee: Vulcan ChemicalsInventor: Rodney L. Klausmeyer
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Patent number: 7102042Abstract: 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: GrantFiled: December 19, 2002Date of Patent: September 5, 2006Assignee: Dow Global Technologies Inc.Inventors: Timothy J. Adaway, Michael A. Gonzalez, Weishi Wu
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Patent number: 7094936Abstract: 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: GrantFiled: October 16, 2003Date of Patent: August 22, 2006Assignee: Great Lakes Chemical CorporationInventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
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Patent number: 7009084Abstract: 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: GrantFiled: February 1, 2003Date of Patent: March 7, 2006Assignees: Uhde GmbH, Vinnolit Technologie GmbH & Co. KGInventors: Michael Benje, Dieter Jaculi, Ingolf Mielke, Peter Schwarzmaier, Klaus Krejci, Joachim Schubert, Horst Ertl
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Patent number: 6977316Abstract: 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: GrantFiled: December 8, 2004Date of Patent: December 20, 2005Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, HsuehSung Tung
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Patent number: 6841708Abstract: 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: GrantFiled: October 12, 1999Date of Patent: January 11, 2005Assignees: Vinnolit Technologie GmbH & Co., Uhde GmbHInventor: Michael Benje
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Patent number: 6835860Abstract: 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: GrantFiled: January 31, 2003Date of Patent: December 28, 2004Assignee: Merck & Co., Inc.Inventors: Yongkui Sun, Thorsten Rosner
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Patent number: 6756513Abstract: 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: GrantFiled: August 16, 2002Date of Patent: June 29, 2004Assignee: Degussa AGInventors: Manfred Neumann, Clemens Osterholt
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Patent number: 6740253Abstract: 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: GrantFiled: January 23, 2002Date of Patent: May 25, 2004Assignee: Council of Scientific and Industrial ResearchInventors: 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
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Patent number: 6693224Abstract: 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: GrantFiled: May 22, 2002Date of Patent: February 17, 2004Assignee: Uhde GmbHInventor: Joachim Motz
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Patent number: 6506952Abstract: 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: GrantFiled: October 18, 2001Date of Patent: January 14, 2003Assignee: Albemarle CorporationInventor: John K. Kendall
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Patent number: 6420617Abstract: 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: GrantFiled: June 8, 2001Date of Patent: July 16, 2002Assignee: Albemarle CorporationInventors: John K. Kendall, Jeffrey T. Aplin
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Patent number: 6284935Abstract: 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: GrantFiled: August 18, 1999Date of Patent: September 4, 2001Assignee: Albemarle CorporationInventors: John K. Kendall, Jeffrey T. Aplin
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Patent number: 6252125Abstract: 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: GrantFiled: April 14, 2000Date of Patent: June 26, 2001Assignee: Krupp Uhde GmbHInventor: Peter Porscha
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Patent number: 6235953Abstract: 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: GrantFiled: August 23, 1999Date of Patent: May 22, 2001Assignee: Vinnolit Monomer GmbH & Co. KGInventors: Peter Schwarzmaier, Ingolf Mielke
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Supported catalyst, process for its production as well as its use in the oxychlorination of ethylene
Patent number: 5986152Abstract: 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: GrantFiled: November 24, 1998Date of Patent: November 16, 1999Assignee: Degussa-Huls AGInventors: Herbert Muller, Stefan Bosing, Ludwig Schmidhammer, Albin Frank, Klaus Haselwarter -
Patent number: 5905177Abstract: 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: GrantFiled: March 15, 1996Date of Patent: May 18, 1999Assignee: Toshoh CorporationInventors: Ikuya Seo, Terumasa Yoshida
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Patent number: 5866732Abstract: 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: GrantFiled: August 22, 1997Date of Patent: February 2, 1999Assignee: BASF AktiengesellschaftInventors: Matthias Eiermann, Klaus Ebel
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Patent number: 5831137Abstract: 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: GrantFiled: February 10, 1997Date of Patent: November 3, 1998Assignee: Huels AktiengesellschaftInventors: Josef Metz, Clemens Osterholt
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Patent number: 5773673Abstract: 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: GrantFiled: July 1, 1997Date of Patent: June 30, 1998Assignee: Occidental Chemical CorporationInventors: Pravin M. Khandare, Edward A. Rowe
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Patent number: 5527975Abstract: 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: GrantFiled: February 13, 1995Date of Patent: June 18, 1996Assignee: Albemarle CorporationInventors: Dominique Cosserat, Francois Stutz