Dehalogenation Or Dehydrohalogenation With Halogenation In Separate Zones Patents (Class 570/220)
  • Patent number: 11780792
    Abstract: A method of producing carbon tetrachloride includes providing a chloromethanes stream, combining the chloromethanes stream with chlorine and additional carbon tetrachloride to form a reaction mixture, wherein the reaction mixture includes at least stoichiometric levels of chlorine, introducing electromagnetic radiation to the reaction mixture and subjecting the reaction mixture to suitable reaction conditions to form product carbon tetrachloride, and collecting a product stream including the product carbon tetrachloride.
    Type: Grant
    Filed: January 10, 2020
    Date of Patent: October 10, 2023
    Assignee: Occidental Chemical Corporation
    Inventors: Robert L. Zeller, III, Darrell G. Hollis, Keith S. Kramer, Brian Calderwood, Rodney L. Klausmeyer, John L. Dawkins
  • Patent number: 10934232
    Abstract: Disclosed is a process for producing a chlorinated C3-6 alkane comprising providing a reaction mixture comprising an alkene and carbon tetrachloride in a principal alkylation zone to produce chlorinated C3-6 alkane in the reaction mixture, and extracting a portion of the reaction mixture from the principal alkylation zone, wherein: a) the concentration of the chlorinated C3-6 alkane in the reaction mixture in the principal alkylation zone is maintained at a level such that the molar ratio of chlorinated C3-6 alkane:carbon tetrachloride in the reaction mixture extracted from the alkylation zone does not exceed 95:5 when the principal alkylation zone is in continuous operation; and/or b) the reaction mixture extracted from the principal alkylation zone additionally comprises alkene and the reaction mixture is subjected to a dealkenation step in which at least about 50% or more by weight of the alkene present in the reaction mixture is extracted therefrom and at least about 50% of the extracted alkene is fed
    Type: Grant
    Filed: April 4, 2019
    Date of Patent: March 2, 2021
    Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBU A.S.
    Inventors: Karel Filas, Pavel Kubicek, Zdenek Ondrus, Petr Sladek
  • Patent number: 10513478
    Abstract: The present invention provides improved processes for preparing halogenated alkanes. In particular, the processes comprise reacting an alkene, a halogenated alkene, or combinations thereof and a halogenated methane with at least one chlorine atom.
    Type: Grant
    Filed: January 4, 2017
    Date of Patent: December 24, 2019
    Assignee: BLUE CUBE IP LLC
    Inventors: John D. Myers, Max M. Tirtowidjojo, Thomas U. Luebbe, Marc Sell
  • Patent number: 10131597
    Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, oligomerization/polymerization of such reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that vaporizing such starting reagents in the presence of one or more organic co-feed reduces such oligomerization/polymerization and improves catalytic stability.
    Type: Grant
    Filed: November 2, 2012
    Date of Patent: November 20, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Selma Bektesevic, Daniel C. Merkel, Haluk Kopkalli, Yuon Chiu
  • Patent number: 10081582
    Abstract: The preparation of chlorinated hydrocarbons by reacting a chlorinated alkane substrate, such as 1,1,1,3-tetrachloropropane, with a source of chlorine, such as chlorine (Cl2), in the presence of a polyvalent molybdenum compound, such as molybdenum pentachloride, is described. With the method of the present invention, the chlorinated alkane product has covalently bonded thereto at least one more chlorine group than the chlorinated alkane substrate, and the chlorinated alkane substrate and the chlorinated alkane product each have a carbon backbone structure that is in each case the same.
    Type: Grant
    Filed: October 20, 2015
    Date of Patent: September 25, 2018
    Assignee: Eagle US 2 LLC
    Inventors: Scott A. Sherwood, Stephen Robert Lester
  • Patent number: 9981892
    Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.
    Type: Grant
    Filed: April 21, 2017
    Date of Patent: May 29, 2018
    Assignee: OCCIDENTAL CHEMICAL CORPORATION
    Inventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Patent number: 9840448
    Abstract: Disclosed is a process for preparing a highly pure 1,1,1,2,3-pentachloropropane product, comprising 1-a) providing a reaction mixture comprising ethylene, carbon tetrachloride and a catalyst in a principal alkylation zone to produce 1,1,1,3-tetrachloropropane in the reaction mixture, and 1-btreating the reaction mixture obtained in step 1-a) to obtain a 1,1,1,3-tetrachloropropane feedstock; 2-a) contacting the 1,1,1,3-tetrachloropropane feedstock with a catalyst in a dehydrochlorination zone to produce a reaction mixture comprising 1,1,1,3-tetrachloropropane and 1,1,3-trichloropropene, and 2-b) treating the reaction mixture obtained in step 2-a) to obtain a 1,1,3-trichloropropene feedstock; 3-a) contacting the 1,1,3-trichloropropene feedstock with chlorine in a reaction zone to produce a reaction mixture containing 1,1,1,2,3-pentachloropropane and 1,1,3-trichloropropene, the reaction zone being different from the dehydrochlorination zone, and 3-b) treating the reaction mixture obtained in step 3-a) to obta
    Type: Grant
    Filed: October 15, 2015
    Date of Patent: December 12, 2017
    Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBU A.S.
    Inventors: Zdenek Ondrus, Pavel Kubicek, Karel Filas, Petr Sladek
  • Patent number: 9663425
    Abstract: The present invention provides a method for the high yield production of HCC-1230xa from the known four step method, wherein the Step 3 crude product (crude HCC-240db) is used directly as the starting material in the Step 4 reaction—but only if the crude HCC-240db contains less than 0.5 wt % of impurities selected from the group consisting of HCC-250fb, HCC-1240za, and mixtures thereof.
    Type: Grant
    Filed: March 16, 2015
    Date of Patent: May 30, 2017
    Assignee: Honeywell International Inc.
    Inventors: Terris Yang, Hsueh Sung Tung
  • Patent number: 9650319
    Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.
    Type: Grant
    Filed: August 17, 2015
    Date of Patent: May 16, 2017
    Assignee: OCCIDENTAL CHEMICAL CORPORATION
    Inventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Patent number: 9624149
    Abstract: Disclosed is a process for preparing a chlorinated alkene, comprising contacting a chlorinated alkane with a catalyst in a dehydrochlorination zone to produce a liquid reaction mixture comprising the chlorinated alkane and the chlorinated alkene, and extracting chlorinated alkene from the reaction mixture, wherein the concentration of the chlorinated alkene in the reaction mixture present in the dehydrochlorination zone is controlled such that the molar ratio of chlorinated alkene:chlorinated alkane is from 1:99 to 50:50.
    Type: Grant
    Filed: October 15, 2015
    Date of Patent: April 18, 2017
    Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBU A.S.
    Inventors: Zdenek Ondrus, Pavel Kubicek, Karel Filas, Petr Sladek
  • Patent number: 9598334
    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. At least one dehydrochlorination is conducted in the gas phase, and is the first process step. 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.
    Type: Grant
    Filed: September 13, 2013
    Date of Patent: March 21, 2017
    Assignee: BLUE CUBE IP LLC
    Inventor: Max M. Tirtowidjojo
  • 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: 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: 8907147
    Abstract: The present invention provides an improved process for producing 1,1,2,3-tetrachloropropene. By using a first reactive distillation column for HCC-250fb dehydrochlorination, and a second reactive distillation column for HCC-240db dehydrochlorination/HCC-1230xf isomerization, the 1,1,2,3-tetrachloropropene manufacturing process can be greatly simplified, resulting in reduced equipment use, energy use, as well as increased productivity.
    Type: Grant
    Filed: January 30, 2014
    Date of Patent: December 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Joshua Close, Terris Tianxue Yang
  • Patent number: 8829254
    Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: September 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv Ratna Singh, David Nalewajek, Andrew Joseph Poss
  • Patent number: 8816140
    Abstract: The present invention provides a process for producing a fluorine-containing alkene of the general formula CF3(CX2)nCF?CH2, wherein X each independently represents F or Cl, and n is an integer of 0 to 2. The process includes a first reaction step of allowing a specific chlorine-containing compound to react with a fluorinating agent under increased pressure in a gas phase in the presence of at least one fluorination catalyst selected from the group consisting of chromium oxide and fluorinated chromium oxide, and a second reaction step of heating the product of the first reaction step in a gas phase under a pressure lower than the pressure in the first reaction step. The process of the present invention can produce a fluorine-containing alkene with a high selectivity with the use of a catalyst that can be easily handled, while suppressing production of by-products that cannot be easily converted into the target or separated.
    Type: Grant
    Filed: February 8, 2011
    Date of Patent: August 26, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Daisuke Karube, Yuzo Komatsu, Atsushi Suzuki
  • Publication number: 20140221705
    Abstract: The present invention provides an improved process for producing 1,1,2,3-tetrachloropropene. By using a first reactive distillation column for HCC-250fb dehydrochlorination, and a second reactive distillation column for HCC-240db dehydrochlorination/HCC-1230xf isomerization, the 1,1,2,3-tetrachloropropene manufacturing process can be greatly simplified, resulting in reduced equipment use, energy use, as well as increased productivity.
    Type: Application
    Filed: January 30, 2014
    Publication date: August 7, 2014
    Applicant: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Joshua Close, Terris Tianxue Yang
  • Publication number: 20140163266
    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: Application
    Filed: August 1, 2012
    Publication date: June 12, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Max M. Tirtowidjojo, Barry B. Fish, David S. Laitar
  • Publication number: 20130190541
    Abstract: A catalyst system for use in oxychlorination, the catalyst system comprising catalyst pellets comprising a catalyst carried on a substrate the pellets having length x, breadth y and depth z, intrinsic density P and bulk density p and diluent beads having length x±25%, breadth y±25% and depth z±25%, intrinsic density?P+25% and a bulk density p ±25%.
    Type: Application
    Filed: July 1, 2011
    Publication date: July 25, 2013
    Applicant: INEOUS EUROPE AG
    Inventors: Lorette Du Preez, Stephen Kevin Lee, Andrea Marsella, Sandro Vidotto
  • Patent number: 8487146
    Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.
    Type: Grant
    Filed: October 13, 2011
    Date of Patent: July 16, 2013
    Assignee: Occidental Chemical Corporation
    Inventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Publication number: 20120035402
    Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.
    Type: Application
    Filed: October 13, 2011
    Publication date: February 9, 2012
    Applicant: OCCIDENTAL CHEMICAL CORPORATION
    Inventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Publication number: 20100036180
    Abstract: The present invention relates to a method of producing liquid 1,2-dichloroethane (DCE), obtained by low-temperature direct chlorination of ethylene, in the presence of a Lewis acid-type catalyst, that makes it possible to obtain, after separation of the catalyst, DCE of sufficient purity to give, via cracking, vinyl chloride monomer (VCM); characterized in that it comprises a step of dechlorination (5) of the liquid DCE stream (4) exiting the chlorination reactor (1), that makes it possible to remove the excess dissolved chlorine, followed by a step of direct evaporation (9) of the whole of the liquid DCE stream (8) exiting said reactor, that makes it possible to separate the catalyst from the evaporated fraction (10) of the stream of DCE good for cracking. The invention also relates to the plant for the implementation of such a method.
    Type: Application
    Filed: July 10, 2007
    Publication date: February 11, 2010
    Inventors: Philippe Leduc, Francois Vanney, Remy Teissier
  • Patent number: 7309471
    Abstract: An apparatus for producing ethylenically unsaturated aliphatic halogenic hydrocarbons by thermal cleavage of saturated aliphatic halogenic carbons using an apparatus that introduces an educt gas stream into a reactor which includes at least one supply conduit which opens into the reactor, the supply conduit feeds a heated gas formed from cleavage promotors and radicals produced by a nonthermal plasma device which permits an increased in the yield of the cleavage reaction.
    Type: Grant
    Filed: April 30, 2003
    Date of Patent: December 18, 2007
    Assignee: Uhde GmbH
    Inventors: Michael Benje, Horst Ertl, Ingolf Mielke, Thomas Wild, Peter Kammerhofer, Peter Schwarzmaier
  • Patent number: 6979754
    Abstract: The invention concerns a method for obtaining directly polymerisable vinyl chloride which consists in subjecting a cooled raw product derived from of pyrolysis of 1,2-dichloroethane, to another cooling process at a temperature not more than 40° C., under pressure ranging between 10 to 15 bars then in leaving it at substantially identical temperature and pressure levels for a duration not more than 20 minutes. The invention also concerns a device for implementing the method.
    Type: Grant
    Filed: October 15, 2002
    Date of Patent: December 27, 2005
    Assignee: ARKEMA
    Inventors: Béatrice Rondot, François Vanney
  • Patent number: 6900363
    Abstract: A process for preparing 1,2-dichloroethane which comprises (A) feeding an ethane-containing feed gas stream into a dehydrogenation zone and dehydrogenating ethane to ethane to give a product gas stream comprising ethane, ethane and secondary constituents, (B) feeding the ethan- and ethene-containing dehydrogenation product gas stream as a single stream or a plurality of substreams, optionally after having separated off secondary constituents, into one or more chlorination zones, chlorinating ethene to 1,2-dichloroethane to give one or more product gas streams comprising 1,2-dichloroethane, ethane and possibly further secondary constituents, isolating 1,2-dichloroethane and one or more ethane-containing circulating gas streams and recirculating the ethane-containing circulating gas stream or streams to the ethane dehydrogenation.
    Type: Grant
    Filed: December 4, 2002
    Date of Patent: May 31, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Harth, Götz-Peter Schindler, Christian Walsdorff, Christian Kuhrs, Falk Simon
  • 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
  • Patent number: 6410265
    Abstract: This invention relates to the isolation of a novel putative efflux gene from Pseudomonas mendocina. The putative efflux gene is useful for probing an organism's efflux system to gain an understanding of the mechanisms of solvent tolerance. The invention further provides a Pseudomonas mendocina strain deficient in this gene. This strain is unable to grow in the presence of chloramphenicol and, compared to the wildtype strain, grows slowly in the presence of high concentrations of PHBA.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: June 25, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Kevin Keqin Chen
  • Patent number: 6103945
    Abstract: Ethylene is chlorinated in a reaction zone to form a product stream containing 1,2-dichloroethane, the latter being then thermally cracked in a cracking zone to form vinyl chloride. Light by-products formed during the thermal cracking step are chlorinated in a zone external and directly downstream of the reaction zone used for the preparation of the 1,2-dichloroethane product stream. The product stream leaving the chlorination reaction zone for the 1,2-dichloroethane are passed into said downstream zone so that the light by-products are chlorinated in the presence of said product stream.
    Type: Grant
    Filed: March 14, 1997
    Date of Patent: August 15, 2000
    Assignee: Elf Atochem S.A.
    Inventor: Sylvie Daire
  • Patent number: 5958757
    Abstract: Saturated aliphatic halocarbons, including environmental contaminants, are degraded to innocuous, environmentally acceptable compounds by contact, either in situ or in a bioreactor, with microorganisms that produce aromatic oxygenases, preferably with use of a co-substrate, for example, phenol, toluene, benzene, ethylbenzene and xylene, including the provision of novel bacteria that produce aromatic oxygenases, and new recombinant microorganisms that contain cloned aromatic oxygenase genes, examples of saturated aliphatic halocarbon that may be degraded to innocuous compounds being chloroform; bromoform; 1,2-dichloroethane; 1,2-dibromoethane; monochloroethane and monobromoethane.
    Type: Grant
    Filed: September 13, 1996
    Date of Patent: September 28, 1999
    Assignee: Envirogen, Inc.
    Inventors: Robert Jon Steffan, Kevin Rock McClay
  • Patent number: 5841004
    Abstract: A novel 3-substituted .alpha.,.beta.-dibromoethylbenzene of formula (I): ##STR1## wherein X represents a halogen atom or a trihalomethyl group, which is useful as an intermediate for pharmaceuticals or agricultural chemicals, is prepared by a simple and high yield process which comprises reacting a 3-substituted .alpha.-bromoethylbenzene represented by formula (II): ##STR2## wherein X is as defined above, or a 3-substituted ethylbenzene represented by formula (III): ##STR3## wherein X is as defined above, with bromine in the presence of a quaternary ammonium salt.
    Type: Grant
    Filed: July 17, 1996
    Date of Patent: November 24, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Ken Tanaka, Manabu Katsurada, Akemi Hosokawa
  • Patent number: 5196617
    Abstract: A process for hydrodehalogenating halogenated organic compounds present in a contaminated aqueous environmental source in which the halogenated organic compounds are reacted with hydrogen gas or a source of hydrogen gas in the presence of a catalyst of palladium on carbon.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: March 23, 1993
    Assignee: Engelhard Corporation
    Inventors: Suphan Kovenklioglu, Edward N. Balko, Jeffrey B. Hoke, Robert J. Farrauto, Gary A. Gramiccioni
  • Patent number: 4960962
    Abstract: ar-Bromoaromatics having an alkenyl side chain on the aromatic nucleus are formed by feeding a beta-bromoalkyl-ar-bromoaromatic compound, together with a substantial excess of water, into a thermal dehydrobromination zone held at or above 475.degree. C., and maintaining a very short residence time (5 seconds or less) in the dehydrobromination zone. Very little extraneous co-products are formed. For example dibromostyrene was produced by co-feeding bromoethyldibromobenzene (BEDB) and excess amounts of water (using nitrogen as a carrier gas) into a Vycor tube packed with glass beads at 500.degree. C. By suitable controlling residence times, the amount of undesired coproducts formed was kept below 1.5 G. C. area %, and the percentage of BEDB conversion was in the range of 84.1% up to 99.1%.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: October 2, 1990
    Assignee: Ethyl Corporation
    Inventor: David R. Brackenridge
  • Patent number: 4899000
    Abstract: A process is provided for the production of allyl chloride from three carbon atom hydrocarbons (propane and/or propylene) using hydrogen chloride or hydrogen chloride/chlorine mixtures as the chlorinating agent. The process includes reaction steps operated in tandem in separate zones first comprising the reaction of perchloroethylene with hydrogen chloride and oxygen in the presence of an oxychlorination catalyst to give hexachloroethane and water, second comprising the vapor phase reaction of hexachloroethane with propane/propylene feedstock to produce allyl chloride, perchloroethylene, and hydrogen chloride, and third isolating the products of the second step and repeating the first step using as starting materials the thus isolated perchloroethylene and hydrogen chloride.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: February 6, 1990
    Inventor: John E. Stauffer
  • Patent number: 4849561
    Abstract: The liquid phase dehydrochlorination of haloalkanes is performed with an initiator mainly comprising decachlorobutane and/or octachloro-1-butene.The process is applicable, in particular, to the production of chloroethylenes from the corresponding polychloroethanes.
    Type: Grant
    Filed: February 18, 1987
    Date of Patent: July 18, 1989
    Assignee: Solvay & Cie (Societe Anonyme)
    Inventor: James Franklin
  • Patent number: 4760206
    Abstract: Ferric chloride (FeCl.sub.3), a known chlorination and polymerization catalyst for 1,3-butadiene ("BD"), can nevertheless be effectively used in a packed or trayed quench tower, operating under essentially anhydrous conditions, without plugging it. Essentially all BD from a crude stream of vinyl chloride (VCl), is removed within a hold-up time of 6 minutes. The speed of removal is note-worthy because less than half the stoichiometric amount of chlorine required to chlorinate the BD is used. The BD is preferentially chlorinated, the time being too short to chlorinate a substantial amount of chloroprene and monovinylacetylene. Only a portion of the BD is removed by chlorination, the remainder being removed by polymerization catalyzed by 100-200 ppm anhydrous FeCl.sub.3.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: July 26, 1988
    Assignee: The B. F. Goodrich Company
    Inventor: Wolfgang W. Schneider
  • Patent number: 4650914
    Abstract: A process is disclosed for preparing 1,1,2,3-tetrachloropropene comprising allylic rearrangement of 2,3,3,3-tetrachloropropene using a substantially anhydrous ferric chloride catalyst. Alternatively, 1,1,2,3-tetrachloropropene is prepared by dehydrochlorination of 1,1,1,2,3-pentachloropropane using a ferric chloride catalyst. Process schemes commencing with the preparation of the precursor 1,1,1,3-tetrachloropropane by reaction of ethylene with carbon tetrachloride are also disclosed.
    Type: Grant
    Filed: January 9, 1985
    Date of Patent: March 17, 1987
    Assignee: Monsanto Company
    Inventor: Scott S. Woodard
  • Patent number: 4590317
    Abstract: A process is disclosed for the economical operation of a commercial ethylene dichloride (EDC) cracking furnace which typically is prone to coking of the tubes through which the EDC is flowed. The EDC cracking furnace is found to be critically sensitive to the presence of trace amounts, 30 ppm or more of FeCl.sub.3 and/or 20 ppm or more of free chlorine, which cause coking of the tubes of the furnace. The coking of the tubes is minimized by maintaining less than 30 ppm by weight of FeCl.sub.3 or less than 20 ppm of free chlorine in the EDC feed to the EDC furnace. In the particular instance where EDC is produced at least in part in a high temperature direct chlorination ("boiling") reactor constructed from mild steel, this goal requires that the chlorine content of the effluent from the boiling reactor be controlled so as not to exceed 20 ppm. But this is to be done without using more than a 2% by weight excess of ethylene over the stoichiometric amount required to produce the EDC in the boiling reactor.
    Type: Grant
    Filed: August 6, 1984
    Date of Patent: May 20, 1986
    Assignee: The B. F. Goodrich Company
    Inventor: John P. Lenczyk
  • Patent number: 4590318
    Abstract: 1,2-Dichloroethane is pyrolyzed in a pyrolysis furnace to produce a stream comprising vinyl chloride and 1,2-dichloroethane. The stream is removed from the furnace and introduced to essentially unheated conduit means to establish a stream flowing in the conduit means. Pyrolysis promoter is introduced to the stream in the conduit means and sensible heat of the stream is utilized in the conduit means to pyrolyze further amounts of 1,2-dichloroethane and to increase the yield of vinyl chloride.
    Type: Grant
    Filed: November 23, 1984
    Date of Patent: May 20, 1986
    Assignee: PPG Industries, Inc.
    Inventor: David A. Longhini
  • Patent number: 4535194
    Abstract: A process is disclosed for preparing 1,1,2,3-tetrachloropropene comprising allylic rearrangement of 2,3,3,3-tetrachloropropene using a substantially anhydrous ferric chloride catalyst. Alternatively, 1,1,2,3-tetrachloropropene is prepared by dehydrochlorination of 1,1,1,2,3-pentachloropropane using a ferric chloride catalyst. Process schemes commencing with the preparation of the precursor 1,1,1,3-tetrachloropropane by reaction of ethylene with carbon tetrachloride are also disclosed.
    Type: Grant
    Filed: July 6, 1983
    Date of Patent: August 13, 1985
    Assignee: Monsanto Co.
    Inventor: Scott S. Woodard
  • Patent number: 4400552
    Abstract: A reagent comprising the product of the reaction of an alkali metal hydroxide with a polyglycol or a polyglycol monoalkyl ether and oxygen, effects complete decomposition of halogenated organic compounds, such as polychlorinated biphenyls (PCBs), when mixed therewith in the presence of oxygen.
    Type: Grant
    Filed: March 5, 1981
    Date of Patent: August 23, 1983
    Assignee: The Franklin Institute
    Inventors: Louis L. Pytlewski, Kenneth Krevitz, Arthur B. Smith
  • Patent number: 4400550
    Abstract: A process for the synthesis of (Z,Z)-11-13-hexadecadienal is disclosed, starting with undecylenic alcohol.
    Type: Grant
    Filed: February 12, 1982
    Date of Patent: August 23, 1983
    Assignee: Albany International Corp.
    Inventors: Clyde E. Bishop, Gary W. Morrow
  • Patent number: 4337368
    Abstract: A reagent, comprising the product of the reaction of an alkali metal with a polyglycol or a polyglycol monoalkyl ether and oxygen, effects complete decomposition of halogenated organic compounds, such as polychlorinated biphenyls (PCBs), when mixed therewith in the presence of oxygen.
    Type: Grant
    Filed: June 11, 1980
    Date of Patent: June 29, 1982
    Assignee: The Franklin Institute
    Inventors: Louis L. Pytlewski, Kenneth Krevitz, Arthur B. Smith
  • Patent number: 4319062
    Abstract: An improved process for production of allyl chloride which comprises (1) thermally chlorinating propylene above 300.degree. C., but below that at which substantial carbon formation is effected, (2) separating the allyl chloride from its by-products, (3) subjecting the unsaturated compounds in said by-products to a low temperature chlorination, (4) separating the 1,2-dichloropropane from the products of said low temperature chlorination, and (5) passing said 1,2-dichloropropane to a cracking furnace. The effluent from the cracking furnace can be recycled to the allyl chloride finishing system by adding it to the high temperature propylene chlorination reactor effluent. Reaction temperatures are optimized to eliminate problems caused by carbon formation in the high temperature chlorination reactor, while overall yields of allyl chloride are increased and effluents which are ecologically and economically undesirable are reduced.
    Type: Grant
    Filed: April 17, 1978
    Date of Patent: March 9, 1982
    Assignee: The Dow Chemical Company
    Inventors: Theodore S. Boozalis, John B. Ivy, Gordon G. Willis
  • Patent number: 4255597
    Abstract: There is disclosed a process for the production of hexachlorocyclopentadiene comprising the steps of:1. Reacting liquid cyclopentadiene and chlorine at a temperature of from about 0.degree. to about 100.degree. C. until an average of at least 4 chlorine atoms has been added per mole of cyclopentadiene to form a first-stage product;2. heating the resultant liquid reaction product of Step 1 in a second stage at a temperature of from about 140.degree. C. to below about 200.degree. C. with chlorine in the presence of from about 0.0001% to about 5.0% (by weight) of an aromatic compound until the reaction products of Step 1 contain an average of about 6 chlorine atoms per molecule, based on cyclopentadiene starting material; wherein said aromatic compound contains from 1 to 3 aromatic rings; at least one of the rings containing a nitrogen atom;3. vaporizing and heating the resulting reaction products of Step 2 in a third stage in the presence of chlorine to a temperature of above 450.degree. C.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: March 10, 1981
    Assignee: Velsicol Chemical Corporation
    Inventors: Kalidas Paul, Glendon D. Kyker
  • Patent number: 4246205
    Abstract: There is disclosed a process for the production of hexachlorocyclopentadiene comprising the steps of:1. Reacting liquid cyclopentadiene and chlorine at a temperature of from about 0.degree. to about 100.degree. C. until an average of at least 4 chlorine atoms has been added per mole of cyclopentadiene to form a first-stage product;2. heating the resultant liquid reaction product of Step 1 in a second stage at a temperature of from about 140.degree. C. to below about 200.degree. C. with chlorine in the presence of from about 0.0001% to about 5.0% (by weight) of an aromatic compound until the reaction products of Step 1 contain an average of about 6 chlorine atoms per molecule, based on cyclopentadiene starting material; wherein said aromatic compound contains from about 4 to about 30 carbon atoms and from 1 to about 4 aromatic rings; and3. vaporizing and heating the resulting reaction products of Step 2 in a third stage in the presence of chlorine to a temperature of above 450.degree. C.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: January 20, 1981
    Assignee: Velsicol Chemical Corporation
    Inventors: Kalidas Paul, Glendon D. Kyker
  • Patent number: 4233251
    Abstract: There is disclosed a process for the production of hexachlorocyclopentadiene comprising the steps of:(a) reacting liquid cyclopentadiene and chlorine at a temperature of from about 0 to about 100 degrees centigrade until a minimum of four chlorine atoms has been added per mole of cyclopentadiene to form a first-stage product;(b) heating the resultant liquid reaction product of step (a) in a second stage at a temperature of from about 140 degrees centigrade to below about 200 degrees centigrade with chlorine in the presence of from about 0.0001 percent to about 5.0 percent (by weight) of a phosphorus compound until the reaction products of step (a) contain an average of about six chlorine atoms per molecule, based on cyclopentadiene starting material, wherein said phosphorus compound is ##STR1## wherein a, b, c, d, e, f, and g are integers independently selected from the group consisting of 0 and 1, and R.sup.1, R.sup.2, and R.sup.
    Type: Grant
    Filed: June 18, 1979
    Date of Patent: November 11, 1980
    Assignee: Velsicol Chemical Corporation
    Inventors: Glendon D. Kyker, Kalidas Paul
  • Patent number: RE47429
    Abstract: The preparation of chlorinated hydrocarbons, such as pentachloropropanes, such as 1,1,1,2,3-pentachloropropane, from tetrachloropropanes, such as 1,1,1,3-tetrachloropropane, in the presence of a polyvalent antimony compound that includes a pentavalent antimony compound, such as antimony pentachloride, is described. Also described are methods for preparing optionally chlorinated alkenes, such as, tetrachloropropenes, from chlorinated alkanes, such as pentachloropropanes, in the presence of ferric chloride and a polyvalent antimony compound that includes a pentavalent antimony compound.
    Type: Grant
    Filed: August 23, 2016
    Date of Patent: June 11, 2019
    Assignee: EAGLE US 2 LLC
    Inventors: Scott A. Sherwood, Stephen Robert Lester