Dehydrohalogenation Patents (Class 570/226)
  • Patent number: 11360064
    Abstract: Oxy-pyrohydrolysis articles, systems and methods for total halogen, in particular fluorine analysis are provided. A sample containing halogen elements is provided into a pyrotube for combustion. A combustion-enhancing bed including ceramic fibers or fabrics is disposed inside the pyrotube to enhance the combustion and protect the pyrotube from damage by corrosive gases.
    Type: Grant
    Filed: March 17, 2017
    Date of Patent: June 14, 2022
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventor: Phanasouk Vorarath
  • Patent number: 11198667
    Abstract: Disclosed is a chemical process of preparing dehydrohedione from Hedione via ?-chlorination and elimination steps. The process can be conducted in a one-pot process or in a continuous reactor system. Accordingly, a simple and cost effective process of preparing cis-Hedione enriched products is developed through reduction of dehydrohedione in the presence of a chiral catalyst system.
    Type: Grant
    Filed: March 30, 2018
    Date of Patent: December 14, 2021
    Assignee: International Flavors & Fragrances Inc.
    Inventors: James S. Sharley, Ian R. Baxendale, Estela Espinos Ferri, Ana Maria Collado Perez, Isabelle Fernandez Fernandez
  • Patent number: 11060024
    Abstract: Mixed halide scintillation materials of the general formula AB(1?y)MyX?wX?(3?w), where 0?y?1, 0.05?w?1, A may be an alkali metal, B may be an alkali earth metal, and X? and X? may be two different halogen atoms, and of the general formula A(1?y)BMyX?wX?(3?w), where 0?y?1, 0.05?w?1, A maybe an alkali metal, B may be an alkali earth metal, and X? and X? are two different halogen atoms. The scintillation materials of formula (1) include a divalent external activator, M, such as Eu2+ or Yb2+. The scintillation materials of formula (2) include a monovalent external activator, M, such as Tl+, Na+ and In+.
    Type: Grant
    Filed: June 26, 2019
    Date of Patent: July 13, 2021
    Assignee: University of Tennessee Research Foundation
    Inventors: Luis Stand, Charles L. Melcher, Mariya Zhuravleva, Hua Wei
  • Patent number: 10017436
    Abstract: The present invention provides a method of making 1,1,1,2,3-pentachloropropane comprising: (1) utilizing 1,1,1,3-tetrachloropropane as a raw material and 1,1,1,2,3-pentachloropropane as a solvent to carry out a dehydrochlorination reaction to obtain 1,1,3-trichloropropene, and after the reaction, (2) introducing chlorine gas into the reaction system to carry out a chlorination reaction to obtain 1,1,1,2,3-pentachloropropane. In the present invention, 1,1,1,2,3-pentachloropropane acts as a solvent or a diluent, and may act as an inhibitor to prevent the production of high-boiling residues such as dimers, oligomers or polymers during the dehydrochlorination process. Then, the conversion rate of 1,1,1,3-tetrachloropropane is increased, and consequently, the yield of final product 1,1,1,2,3-pentachloropropane is also increased.
    Type: Grant
    Filed: March 26, 2018
    Date of Patent: July 10, 2018
    Assignee: Jiangxi Tianyu Chemical Co., Ltd.
    Inventors: Zhong Zhou, Haipeng Xu, Yiming Yu, Peng Peng, Yaling Zhao, Xichao Wang, Xiaori Yue
  • Patent number: 9056305
    Abstract: The present invention discloses a catalyst used in preparing vinyl chloride, its method of preparation, and its applications. Said catalyst used in making vinyl chloride comprises activated carbon as a support, a barium compound and a phosphorus compound supported thereon. The barium compound accounts for 0.2% to 20% of the total mass of the catalyst and the phosphorus compound accounts for 0% to 10% of the total mass of the catalyst based on the mass percentage. A water-soluble barium compound, a water-soluble phosphorus compound, an aqueous polymer monomer, and water are mixed to form a solution or emulsion A. The activated carbon is added into the solution or emulsion A. The activated carbon is removed from water after impregnation, spin-dried, and then the monomers are polymerized. The activated carbon, after polymerization step, is heated to remove water and to decompose and carbonize the polymer. The catalyst after carbonization was activated to obtain a catalyst used in making vinyl chloride.
    Type: Grant
    Filed: October 26, 2011
    Date of Patent: June 16, 2015
    Assignees: SHANGHAI CAS ADVANCED RESEARCH INSTITUTE, ZHONGKE YIGONG (XIAMEN) CHEMICAL TECHNOLOGY CO., LTD.
    Inventors: Biao Jiang, Jinguang Zhong
  • Patent number: 9040760
    Abstract: This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl?CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.
    Type: Grant
    Filed: October 27, 2011
    Date of Patent: May 26, 2015
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
  • Patent number: 9018428
    Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 28, 2015
    Assignee: Honeywell International Inc.
    Inventor: Stephen A. Cottrell
  • Patent number: 9012702
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCFClCH2X with a catalyst in a reaction zone to produce a product mixture comprising RfCF?CHX, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, X ?H, F, Cl, Br or I, M=K, Na or Cs, and Y?F, Cl or Br.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: April 21, 2015
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Patent number: 9012705
    Abstract: The invention relates to a process for the preparation of formula (I) which process comprises pyrolyzing a compound of formula (II) wherein X is chloro or bromo, and to compounds which may be used as intermediates for the manufacture of the compound of formula I and to the preparation of said intermediates.
    Type: Grant
    Filed: August 22, 2011
    Date of Patent: April 21, 2015
    Assignees: Syngenta Paticipations AG, Syngenta Limited
    Inventors: George Robert Hodges, Dominik Faber, Alan James Robinson, Andrew Charles Shaw
  • Patent number: 8921622
    Abstract: A process for the selective dehydrofluorination of hydrochlorofluoroalkanes and novel hydrochlorofluoroalkenes is described wherein an effective amount of a catalytically active metal compound is applied which is selected from the group consisting of AlF3??, MgAlxF2+3x?? and MgZryF2+4y??, wherein x and y have, independently of one another, values in the range of from 0 to 0.33 and ? has a value in the range of from 0 to 0.1. Certain hydrofluorochloroalkenes are also described, as well as their use as intermediates in chemical reactions.
    Type: Grant
    Filed: March 31, 2011
    Date of Patent: December 30, 2014
    Assignee: Solvay SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Patent number: 8912369
    Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a composition containing a compound of the general formula (1): CF3—CH2—CHClX (where X is a fluorine atom or a chlorine atom) into contact with a solid catalyst in the presence of hydrogen chloride. In this production method, the composition containing ozone depleting HCFC such as 3-chloro-1,1,1,3-tetraluoforpropane or 3,3-dichloro-1,1,1-trifluoropropane can be efficiently converted to the 1-chloro-3,3,3-trifluoropropene, which has less influence on the global environment and is useful as a solvent, a cleaning agent, a coolant, a working fluid, a propellant, a raw material for fluorinated resins etc.
    Type: Grant
    Filed: June 27, 2013
    Date of Patent: December 16, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Hideaki Imura, Naoto Takada
  • Patent number: 8907148
    Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of a feedstock comprising 1,2,3-trichloropropane and chlorinates the 1,1,2,3-tetrachloropropane generated by the process prior to a dehydrochlorination step. Production of the less desirable pentachloropropane isomer, 1,1,2,3,3-pentachloropropane, is thus minimized. The present processes provide better reaction yield as compared to conventional processes that require dehydrochlorination of 1,1,2,3-tetrachloropropane prior to chlorinating the same. The present process can also generate anhydrous HCl as a byproduct that can be removed from the process and used as a feedstock for other processes, while limiting the production of waste water, thus providing further time and cost savings.
    Type: Grant
    Filed: August 1, 2012
    Date of Patent: December 9, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Max M. Tirtowidjojo, Barry B. Fish, David S. Laitar
  • Patent number: 8889927
    Abstract: This invention relates to a method to improve 1,1,3-trichloropropene (HCC-1240za) and/or 3,3,3-trichloropropene (HCC-1240zf) selectivity in the dehydrochlorination of 1,1,1,3-tetrachloropropane (HCC-250fb). In normal practice, FeCl3 is used as the catalyst for the dehydrochlorination of HCC-250fb to produce 1,1,3-trichloropropene and/or 3,3,3-trichloropropene. Here the improvement comprises, using as the starting material, a mixture comprising HCC-250fb and Heavies generated from the reaction of CCl4 and ethylene to produce HCC-250fb, wherein the Heavies comprise one or more tetrachloropentane isomers. These compounds reduce or eliminate the formation of unwanted high boiling compounds (HBCs).
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Terris Yang, Joshua Close, Hsueh Sung Tung
  • Patent number: 8889928
    Abstract: This invention relates to a method to improve 1,1,3-trichloropropene (HCC-1240za) and/or 3,3,3-trichloropropene (HCC-1240zf) selectivity in the dehydrochlorination of 1,1,1,3-tetrachloropropane (HCC-250fb). In normal practice, FeCl3 is used as the catalyst for the dehydrochlorination of HCC-250fb to produce 1,1,3-trichloropropene and/or 3,3,3-trichloropropene. The present invention demonstrates that when using FeCl3 as the catalyst for 1,1,1,3-tetrachloropropane dehydrochlorination, the reaction product contains significant amounts of high boiling compounds, such as pentachlorocyclohexene and/or hexachlorocyclohexane species. The addition of one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system, inhibits the formation of these high boiling compounds and improves selectivity to the desired product.
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Terris Yang, Hsueh Sung Tung
  • Patent number: 8884082
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a carbon catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.
    Type: Grant
    Filed: February 16, 2012
    Date of Patent: November 11, 2014
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Publication number: 20140329983
    Abstract: Process for the manufacture of vinyl chloride monomer (VCM), comprising step 1): subjecting 1,2-dichloroethane (EDC) to pyrolysis in order to generate a gas mixture comprising VCM, hydrochloric acid (HCl), and EDC; step 2): quenching and/or cooling and/or condensing such gas mixture to a liquid+gas mixture; step 3): subjecting such liquid+gas mixture to a first separation step to remove substantially all the HCl from the liquid+gas mixture so as to leave a stream consisting substantially of VCM and EDC; and step 4): subjecting such VCM+EDC stream to a second separation step so as to get a stream of substantially pure VCM and a stream of unconverted EDC, wherein a heat exchanger is used to heat up the VCM+EDC stream prior to being fed to a distillation column in step 4), such heat exchanger being powered by a stream of hot fluid available in any one of steps 2) to 4) of the process.
    Type: Application
    Filed: December 4, 2012
    Publication date: November 6, 2014
    Inventors: Andrea Salto, Maria Martin Carnicero, Paul Julius Degraeve, Michel Lempereur
  • 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: 8841493
    Abstract: The subject matter of the invention is a process for preparing fluoroolefin compounds. The invention relates more particularly to a process for producing a (hydro)fluoroolefin compound, which comprises (i) bringing at least one compound comprising from three to six carbon atoms, at least two fluorine atoms and at least one hydrogen atom, on the condition that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, into contact with a solid reactant comprising calcium hydroxide.
    Type: Grant
    Filed: May 4, 2010
    Date of Patent: September 23, 2014
    Assignee: Arkema France
    Inventors: Dominique Guillet, Michel Devic
  • Patent number: 8809601
    Abstract: The invention relates to a method for preparing olefin fluorine compounds.
    Type: Grant
    Filed: May 19, 2010
    Date of Patent: August 19, 2014
    Assignee: Arkema France
    Inventors: Jean-Michel Bossoutrot, Pierre-Marie Sedat
  • Patent number: 8791311
    Abstract: The present invention provides a process for preparing 1,1,2,3-tetrachloropropene, including heating 1,1,1,2,3-pentachloropropane in a gas phase in the absence of a catalyst to carry out a dehydrochlorination reaction. According to the process of the present invention, 1,1,2,3-tetrachloropropene (HCC-1230xa) can be efficiently produced by a simple and economically advantageous method that is suitable for industrial-scale production.
    Type: Grant
    Filed: November 24, 2010
    Date of Patent: July 29, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Masatoshi Nose, Atsushi Suzuki
  • Publication number: 20140179962
    Abstract: Processes for the production of chlorinated propenes are provided wherein a dehydrochlorination reaction occurs prior to a first chlorination reaction. The present processes make use of at least one reactor twice, i.e., at least two reactions occur in the same reactor. Cost and time savings are thus provided. Additional savings can be achieved by conducting more than two chlorination reactions, or all chlorination reactions, in one chlorination reactor, and/or by conducting more than two dehydrochlorination reactions, or all dehydrochlorination reactions, within a single dehydrochlorination reactor.
    Type: Application
    Filed: August 4, 2012
    Publication date: June 26, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Max M. Tirtowidjojo, Barry B. Fish, David S. Laitar
  • Publication number: 20140081055
    Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of 1,2-dichloropropane, a by-product in the production of chlorohydrin, as a low cost starting material, alone or in combination with 1,2,3-trichloropropane. The present processes can also generate anhydrous HCl as a byproduct that can be removed from the process and used as a feedstock for other processes, providing further time and cost savings. Finally, the processes are advantageously conducted in the liquid phase, thereby presenting additional savings as compared to conventional, gas phase processes.
    Type: Application
    Filed: May 18, 2012
    Publication date: March 20, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES, LLC
    Inventors: Max M. Tirtowidjojo, William J. Kruper, JR., Barry B. Fish, David S. Laitar
  • Patent number: 8586804
    Abstract: Disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising contacting 1,1,1,3,tetrachloropropane in the vapor phase in a reaction zone with a catalyst comprising iron, to produce a product mixture comprising 1,1,3-trichloro-1-propene; and recovering said 1,1,3-trichloro-1-propene from the product mixture produced. Also disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising heating 1,1,1,3-tetrachloropropane in the liquid phase to produce a mixture comprising 1,1,3-trichloro-1-propene, cooling said mixture, separating hydrogen chloride from said mixture and recovering 1,1,3-trichloro-1-propene.
    Type: Grant
    Filed: October 21, 2011
    Date of Patent: November 19, 2013
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Robert D. Lousenberg, Andrew Jackson
  • Publication number: 20130281744
    Abstract: The invention relates to a process for the preparation of formula (I) which process comprises pyrolysing a compound of formula (II) wherein X is chloro or bromo, and to compounds which may be used as intermediates for the manufacture of the compound of formula I and to the preparation of said intermediates.
    Type: Application
    Filed: August 22, 2011
    Publication date: October 24, 2013
    Applicant: Syngenta Crop Protection LLC
    Inventors: George Robert Hodges, Dominik Faber, Alan James Robinson, Andrew Charles Shaw
  • Publication number: 20120289751
    Abstract: The present invention provides a process for preparing 1,1,2,3-tetrachloropropene, including heating 1,1,1,2,3-pentachloropropane in a gas phase in the absence of a catalyst to carry out a dehydrochlorination reaction. According to the process of the present invention, 1,1,2,3-tetrachloropropene (HCC-1230xa) can be efficiently produced by a simple and economically advantageous method that is suitable for industrial-scale production.
    Type: Application
    Filed: November 24, 2010
    Publication date: November 15, 2012
    Inventors: Masatoshi Nose, Atsushi Suzuki
  • Patent number: 8258355
    Abstract: Provided is a continuous process for preparing 1,1,2,3-tetrachloro-1-propene having the steps of catalytically dehydrochlorinating CH2ClCCl2CH2Cl in the gas phase to produce CHCl?CClCH2Cl; chlorinating the CHCl?CClCH2Cl to form CHCl2CCl2CH2Cl; and catalytically dehydrochlorinating the CHCl2CCl2CH2Cl in the gas phase to form CCl2?CClCH2Cl.
    Type: Grant
    Filed: July 24, 2008
    Date of Patent: September 4, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung, Michael Van Der Puy, Jing Ji Ma
  • Patent number: 8178466
    Abstract: The present disclosure provides methods for pre-treating activated carbon before it is used in a dehydrochlorination process. The methods can comprise mixing the activated carbon with an acid, an oxidizing agent in a liquid phase, or an oxidizing agent in a gas phase. Activated carbons undergoing one or more of these methods can exhibit improved stability during the dehydrochlorination process.
    Type: Grant
    Filed: January 14, 2011
    Date of Patent: May 15, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh S. Tung
  • Publication number: 20120116133
    Abstract: The invention relates to a method for preparing olefin fluorine compounds.
    Type: Application
    Filed: May 19, 2010
    Publication date: May 10, 2012
    Applicant: Arkema France
    Inventors: Jean-Michel Bossoutrot, Pierre-Marie Sedat
  • Publication number: 20120053374
    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: Application
    Filed: June 17, 2010
    Publication date: March 1, 2012
    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
  • 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: 20110230683
    Abstract: Process and apparatus for producing ethylenically unsaturated halogenated hydrocarbons The invention relates to a process and an apparatus for preparing ethylenically unsaturated halogenated hydrocarbons, preferably vinyl chloride by thermal dissociation of 1,2-dichloroethane, using physical or chemical measures which initiate the dissociation reaction. The process/apparatus described makes it possible to increase the amount produced using dissociation reactors of a given size considerably. Use is made here of initiating measures to increase the heat flux through the wall of the reaction tube and at the same time the feed stream and the heating power of the reaction furnace are increased so that the conversion of the reaction is not significantly increased compared to processes without use of initiating measures.
    Type: Application
    Filed: September 3, 2009
    Publication date: September 22, 2011
    Inventors: Michael Benje, Peter Kammerhofer, Klaus Krejci, Rainer Kampschulte, Helmut Grumann
  • Publication number: 20110230684
    Abstract: The invention relates to a process and an apparatus for product-conserving thermal dissociation of halogenated aliphatic hydrocarbons, preferably for thermal dissociation of 1,2-dichloroethane to vinyl chloride. This uses chemical dissociation promoters and/or physical measures which initiate the dissociation reaction. The initiation of the dissociation reaction, with the same conversion, lowers the temperature level in the reaction mixture and the temperature of the dissociation gas on exit from the dissociation furnace. The amount and the exit temperature of the flue gas from the radiation zone of the dissociation furnace likewise decrease at the same time.
    Type: Application
    Filed: September 3, 2009
    Publication date: September 22, 2011
    Inventors: Michael Benje, Peter Kammerhofer, Klaus Krejci, Rainer Kampschulte, Helmut Grumann
  • Patent number: 7968756
    Abstract: Process and apparatus to form vinyl chloride monomer from ethylene dichloride in a cracking furnace, including a firebox chamber having a thermal protective layer disposed on refractory walls and/or process tubes disposed within the chamber, a quencher to form vinyl chloride monomer, and fractionator separate products. The thermal protective layer which contains an inorganic adhesive for metal/alloy tubes or colloidal silica and/or colloidal alumina for refractory walls or ceramic tubes, a filler, and one or more emissivity agents.
    Type: Grant
    Filed: August 12, 2008
    Date of Patent: June 28, 2011
    Assignee: Wessex Incorporated
    Inventors: John W. Olver, Jason Andrew Simmons
  • Patent number: 7884254
    Abstract: The present disclosure provides methods for pre-treating activated carbon before it is used in a dehydrochlorination process. The methods can comprise mixing the activated carbon with an acid, an oxidizing agent in a liquid phase, or an oxidizing agent in a gas phase. Activated carbons undergoing one or more of these methods can exhibit improved stability during the dehydrochlorination process.
    Type: Grant
    Filed: August 7, 2008
    Date of Patent: February 8, 2011
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7767869
    Abstract: The invention relates to a process for the production of vinyl chloride by thermal cracking, in which the energy balance, the operating time of the cracking furnace and/or the yield of the reaction are distinctly enhanced in comparison with the prior art. A pressure of from 1.4 to 2.5 MPa is established in the cracking coil at a temperature of from 450 to 550° C. and, for pre-heating the EDC (=1,2-dichloroethane) introduced, inter alia the waste heat of the gas stream leaving the top of the quench column is utilized.
    Type: Grant
    Filed: March 17, 2004
    Date of Patent: August 3, 2010
    Assignee: Vinnolit Technologie GmbH & Co. KG
    Inventors: Peter Kammerhofer, Ingolf Mielke, Peter Schwarzmaier
  • Patent number: 7625988
    Abstract: The present invention is directed to novel flame retardant monomers and polymers, wherein the flame retardant properties of the polymers are provided by functionality in pendant groups attached to a polymer backbone (as opposed to the polymer backbone itself possessing flame retardant properties. The present invention is also directed to methods of making such polymers and monomers, and articles of manufacture incorporating such monomers and polymers.
    Type: Grant
    Filed: June 18, 2004
    Date of Patent: December 1, 2009
    Assignee: William Marsh Rice University
    Inventors: James M. Tour, Joshua L. Jurs, Jason J. Stephenson
  • Publication number: 20090118555
    Abstract: An integrated process for the manufacture of HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze) by first catalytically dehydrofluorinating 1,1,1,3,3-pentafluoropropane to thereby produce a mixture of cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and hydrogen fluoride. Then optionally recovering hydrogen fluoride, catalytically isomerizing cis-1234ze into trans-1234ze, and recovering trans-1,3,3,3-tetrafluoropropene.
    Type: Application
    Filed: January 5, 2009
    Publication date: May 7, 2009
    Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
  • Patent number: 7473810
    Abstract: Provided is a method for selectively preparing 2-chloropentafluoropropene comprising catalytic dechlorination of 1,2,2-trichloro-1,1,3,3,3-pentafluoropropane in the presence of hydrogen and a noble metal catalyst. Also provided is method for dechlorinating a vicinal chloride substituted organic compound using a palladium/barium sulfate catalyst.
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: January 6, 2009
    Assignee: Honeywell International Inc.
    Inventors: Michael Van Der Puy, Jingji Ma
  • Patent number: 7135601
    Abstract: A process for producing a producing a product of the formula: R—CF?CHR1 wherein R is F or CF3 and R1 is F when R is F and is H when R is CF3 by reacting a reactant of the formula: CF3—R2 wherein R2 is selected from and wherein R3 is H, F or Cl and R4 is H or Cl, in the presence of a suitable catalyst, with a reducing agent selected from methane, methyl chloride and mixtures thereof, in a gas phase reaction.
    Type: Grant
    Filed: March 28, 2005
    Date of Patent: November 14, 2006
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, HsuehSung Tung
  • Patent number: 7033811
    Abstract: The present invention relates to isolated polypeptides having Family 74 xyloglucanase activity and isolated nucleic acid sequences encoding the polypeptides. The invention also relates to nucleic acid constructs, vectors, and host cells comprising the nucleic acid sequences as well as methods for producing and using the polypeptides.
    Type: Grant
    Filed: April 18, 2003
    Date of Patent: April 25, 2006
    Assignee: Novozymes, Inc.
    Inventors: Michael W. Rey, Elizabeth J. Zaretsky, Jeffrey A. Haas
  • Patent number: 6909024
    Abstract: This invention is a process for producing vinyl chloride from an ethylene-containing feed, oxygen, and a chlorine source in the presence of a catalyst. The process permits direct production of vinyl chloride in a single reactor system, and further permits ethane to be used as the C2 hydrocarbon feed with recycle of ethylene from the product stream to constitute the ethylene specified for the feed. This invention in another aspect concerns also a composition of matter, and a method for making the composition, wherein the composition is useful as a catalyst for the vinyl chloride process. The composition comprises a rare earth-containing material, with the proviso that the catalyst prepared therefrom is substantially free of iron and copper and with the further proviso that when cerium is present the catalyst further comprises at least one more rare earth element other than cerium.
    Type: Grant
    Filed: October 3, 2000
    Date of Patent: June 21, 2005
    Assignee: The Dow Chemical Company
    Inventors: Mark E. Jones, Michael M. Olken, Daniel A. Hickman
  • Patent number: 6797845
    Abstract: A process for producing vinyl chloride monomer where significant quantities of both ethane and ethylene in input streams to the affiliated reactor where hydrogen chloride in the reactor effluent is essentially fully recovered from the reactor effluent in the first unit operation after the ethane/ethylene-to-vinyl reaction step or stage. Steps are presented of oxydehydro-chlorination catalytic reaction of ethane, ethylene, hydrogen chloride, oxygen, and chlorine; quenching the reactor effluent stream to provide a raw product stream having essentially no hydrogen chloride; and separation of the raw product stream into a vinyl chloride monomer product stream and into a lights stream; and recycling the lights steam to the reactor.
    Type: Grant
    Filed: May 14, 2002
    Date of Patent: September 28, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Daniel A. Hickman, John P. Henley, Mark E. Jones, Kenric A. Marshall, Daniel J. Reed, William D. Clarke, Michael M. Olken, Lee E. Walko
  • Patent number: 6441257
    Abstract: In a process for the treatment of a cracking gas formed by pyrolysis of 1,2-dichloroethane (EDC), in which the cracking gas is split into its principal components hydrogen chloride (HCl), vinyl chloride (VCM) and unreacted 1,2-dichloroethane (EDC), and these are formed in substantially pure form, where, in the first step of the treatment of the cracking gas, the solids are separated therefrom in a quench zone, the disadvantages of the prior art are intended to be reduced at least partly and in particular the energy losses which usually arise due to the substantial condensation of the quench gas and its re-heating for the purposes of distillative separation are avoided and, due to the circulation of the unreacted EDC at a higher temperature level, the original conversion in the pyrolytic cracking of EDC is intended to be subsequently increased.
    Type: Grant
    Filed: October 9, 2000
    Date of Patent: August 27, 2002
    Assignee: Krupp Uhde GmbH
    Inventor: Friedrich Seidelbach
  • Patent number: 6426440
    Abstract: The work-up of the gaseous products from the thermal cracking of 1,2-dichloroethane is simplified if the cracking gases are cooled to a temperature range of about 150 to 180° C., only a subsidiary proportion, which comprises all the coke formed, being condensed and fed to a separate work-up.
    Type: Grant
    Filed: December 26, 2000
    Date of Patent: July 30, 2002
    Assignee: Vinnolit Monomer GmbH & Co. KG
    Inventors: Thomas Wild, Juergen Eichler, Werner Strang, Peter Widmann
  • Publication number: 20020077514
    Abstract: Catalysts for the fluid-bed hydrodechlorination of carbon tetrachloride to chloroform having high catalytic stability and comprising platinum supported on microspheroidal gamma alumina, characterized in that the platinum is in the form of particles dispersed throughout the mass of the support.
    Type: Application
    Filed: October 9, 2001
    Publication date: June 20, 2002
    Inventors: Michele Rossi, Carlo Rubini, Antonia Pasquale, Luigi Cavalli
  • Patent number: 6388151
    Abstract: A method for synthesizing tetramethylcyclopentadiene from 2,3-dibromobutane is described. A 2-bromo-2-butene Grignard is reacted with an ethyl formate to produce a 3,5-dimethyl-2,5-heptadiene-4-ol magnesium bromide which is then quenched with acetic acid to produce 3,5-dimethyl-2,5-hepadiene-4-ol.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: May 14, 2002
    Assignee: Boulder Scientific Company
    Inventors: Jeffrey M. Sullivan, Richard D. Crawford
  • Patent number: 6368494
    Abstract: A method of reducing the formation of coke deposits on the heat-transfer surfaces of an ethylene dichloride to vinyl chloride pyrolysis furnace comprising exposing the heat transfer surfaces of said pyrolysis furnace to a phosphite selected from the group consisting of phosphites with the general formula: wherein A1, A2 and A3 are selected from the group consisting of —OR1, —SR2 and Cl, wherein R1 and R2 are selected from the group consisting of alkyl, aryl, alkylaryl and arylalkyl, wherein A1, A2 and A3 may be the same or different, provided that at least one of A1, A2, and A3 is not Cl.
    Type: Grant
    Filed: August 14, 2000
    Date of Patent: April 9, 2002
    Assignee: Nalco/Exxon Energy Chemicals, L.P.
    Inventor: Youdong Tong
  • Publication number: 20020022753
    Abstract: Halogenated compounds are dehydrohalogenated in a multi-stage bubble reactor wherein agitation of the reactor contents is provided by in situ generation and vaporization of reaction product having a boiling point lower than that of the reactants.
    Type: Application
    Filed: March 7, 2001
    Publication date: February 21, 2002
    Inventors: David William Drew, Terry Wayne Redwine