Including Chemical Reaction With By-product Hydrogen Halide Patents (Class 570/229)
  • Patent number: 9732017
    Abstract: A process for the dehydrochlorination of a chlorinated hydrocarbon comprising at least one chlorine atom and at least one hydrogen atom on vicinal carbon atoms to yield the corresponding unsaturated hydrocarbon, said process comprising contacting the chlorinated hydrocarbon with a guanidinium salt or its guanidine precursor.
    Type: Grant
    Filed: July 28, 2014
    Date of Patent: August 15, 2017
    Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Ivan Wlassics, Marco Colladon, Stefano Millefanti, Giuseppe Marchionni, Marco Piccinini
  • Patent number: 9475739
    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: October 25, 2016
    Assignee: BLUE CUBE IP LLC
    Inventors: Max M. Tirtowidjojo, Barry B. Fish, David S. Laitar
  • Patent number: 9403741
    Abstract: Processes for the production of chlorinated alkanes are provided. The present processes comprise dehydrochlorinating one or more trichloroalkanes having from 3-6 carbon atoms and vicinal chlorine atoms, followed by a series of sequential chlorination and/or further dehydrochlorination steps. Because the trichloroalkane is first dehydrochlorinated, rather than being first chlorinated, greater specificity to desired tetra- and pentachloroalkanes can be seen.
    Type: Grant
    Filed: March 7, 2014
    Date of Patent: August 2, 2016
    Assignee: BLUE CUBE IP LLC
    Inventors: Max M. Tirtowidjojo, David S. Laitar, Matthew L. Grandbois, William J. Kruper, Jr., Edward M. Calverley
  • Patent number: 8907149
    Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of a feedstream comprising 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. Selectivity of the process is enhanced over conventional processes employing successive chlorinations and/or dehydrochlorinations, by conducting at least one chlorination in the presence of an ionic chlorination catalyst. The present processes may 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: May 18, 2012
    Date of Patent: December 9, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Max M. Tirtowidjojo, William J. Kruper, Jr., Barry B. Fish, David S. Laitar
  • 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: 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
  • Publication number: 20140163265
    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
  • 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: 8115038
    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: December 17, 2008
    Date of Patent: February 14, 2012
    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: 20090216055
    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: December 17, 2008
    Publication date: August 27, 2009
    Inventors: Richard L. Wilson, Rodney D. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Patent number: 5705720
    Abstract: A thermal process for cracking 1,2-dichloroethane to form vinyl chloride comprising heating 1,2-dichloroethane in a reaction zone at a temperature between 300.degree. and 650.degree. C. under an absolute pressure between 1 and 40 bars; said heating being conducted in the presence of hydrochloric acid.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: January 6, 1998
    Assignee: Atochem
    Inventors: Claude Demaiziere, Jean Lesparre, Yves Correia
  • Patent number: 5672792
    Abstract: Process for preparing chloroprene by dehydrochlorinating 3,4-dichloro-1-butene in the presence of lime and a polyol, such as a glycol selected from (poly)ethylene glycol and (poly)propylene glycol or sugars, with ethylene glycol being preferred.
    Type: Grant
    Filed: September 19, 1994
    Date of Patent: September 30, 1997
    Assignee: Enichem Elastomeres France SA
    Inventors: Jean-Pierre Tassara, Michel Baudouin
  • Patent number: 5659093
    Abstract: There are provided production methods of 1,1,1,3,3-pentafluoropropane characterized in that 1,1,1,3,3-pentafluoro-2,3-dichloropropane is reacted with hydrogen fluoride in the presence of a noble metal catalyst; of 1,1,1,3,3-pentafluoro-2-halogeno-3-chloropropane characterized in that the halogenated propene indicated as general formula I is fluorinated in the presence of antimony trihalogenide and/or antimony pentahalogenide by hydrogen fluoride of mole ratio of or over five times the said antimony halogenide in a liquid phase; and of 1,1,1,2,3,3-hexaohloropropene characterized in that 1,1,1,2,2,3,3-heptachloropropane is reacted with an aqueous solution of alkali metal hydroxide in the presence of a phase transfer catalyst. Therefore, an industrial manufacturing method which is possible to obtain the objective product easily at low cost and high yield can be provided.
    Type: Grant
    Filed: June 27, 1995
    Date of Patent: August 19, 1997
    Assignee: Daikin Industries Ltd.
    Inventors: Seiji Takubo, Hirokazu Aoyama, Tatsuo Nakada
  • Patent number: 5545781
    Abstract: A process for producing chloroprene by means of the dehydrochlorination of 3,4-dichloro-1-butene is disclosed, which is characterized in that the dehydrochlorination is carried out in the presence of lime and a primary amine having the general formula R--NH.sub.2, in which R is a monofunctional C.sub.1 -C.sub.15 hydrocarbyl radical selected from linear or branched alkyl, alkylaryl, cyclohexyl, alkylcyclohexyl, cyclopentyl, alkylcyclopentyl radicals.
    Type: Grant
    Filed: September 19, 1994
    Date of Patent: August 13, 1996
    Assignee: Enichem Elastomeres France S.A.
    Inventors: Michel Baudouin, Jean-Pierre Tassara
  • Patent number: 5176897
    Abstract: This application relates to a catalyst and a process using this catalyst to convert or destroy organic compounds including organohalogen compounds. A preferred catalyst contains as catalytic components titania, vanadium oxide, tungsten oxide, tin oxide and at least one noble metal selected from the group consisting of platinum, palladium and rhodium, characterized in that the vanadium oxide, tungsten oxide and noble metals are uniformly dispersed on the titania. The process of this invention comprises contacting the gas stream, which contains organohalogen compounds and other organic compounds, at a temperature of about 200.degree. to about 500.degree. C. with the catalyst described above in the presence of an oxidizing agent and water. The oxidizing agent can be oxygen or air.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: January 5, 1993
    Assignee: Allied-Signal Inc.
    Inventor: George R. Lester
  • Patent number: 5151263
    Abstract: A process for the catalytic decomposition of chlorofluoro-alkanes commonly named as "flons" into harmless substances against destructing ozone layer of the stratosphere by using the catalyst comprising alumina or alumina -silica complexed oxide, wherein the range of Al/(Al+Si)atomic ratio is 1.0 to 0.5, in the presence of steam at the temperature of 350.degree. to 1.000.degree. C.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: September 29, 1992
    Assignee: Dupont-Mitsui Fluorochemicals Co., Ltd.
    Inventors: Susumu Okazaki, Akito Kurosaki
  • Patent number: 5118492
    Abstract: A process for the catalytic decomposition of chlorofluoro-alkanes commonly named as "flons" into harmless substances against destructing ozone layer of the stratosphere by using the catalyst comprising iron oxide supported on active carbon at the temperature more than 300.degree. C. in the presence of steam.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: June 2, 1992
    Assignee: Dupont-Mitsui Fluorochemicals Co., Ltd.
    Inventors: Susumu Okazaki, Akito Kurosaki
  • 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: 4629816
    Abstract: 2,3-Dichlorobutadiene-(1,3) is obtained from 2,3,4-trichlorobutene-1 by dehydrohalogenation in the presence of a phase transfer catalyst, an inhibitor and oxygen according to an improved process in which the aqueous solution of an alkali metal hydroxide is added to the mixture of trichlorobutene, catalyst, inhibitor and optionally water, and the reaction is carried out at a temperature of from -10.degree. to +60.degree. C. under an inert gas which contains from 0.1 to 8% by weight of oxygen.
    Type: Grant
    Filed: March 1, 1983
    Date of Patent: December 16, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef Heinrich, Rudolf Casper, Manfred Beck
  • Patent number: 4605800
    Abstract: An improved process for the catalytic dehydrochlorination of 3,4-dichlorobutene-1 with aqueous alkali, wherein the effluent from the dehydrochlorination reactor is separated into phases, and the organic phase is steam-stripped at low temperature (below about 80.degree. C.) to recover chloroprene product, while the steam stripper heels are returned to the dehydrochlorination reactor. A small portion of the heels are purged prior to being recycled. Most of the catalyst is recovered and returned to the reaction, but a small amount of make-up catalyst is added. Chloroprene made in this process is a valuable monomer which finds use in the manufacture of a broad line of synthetic elastomers of considerable industrial interest.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: August 12, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Joseph F. Englert, Jr., Louis J. Maurin, III, Clare A. Stewart, Jr.
  • Patent number: 4540838
    Abstract: Chloroprene is produced by reacting 3,4-dichlorobutene-1 in an aqueous solution of an alkali metal hydroxide in the presence of at least one of furfuryl alcohol and tetrahydrofurfuryl alcohol preferably at 20.degree. to 70.degree. C.
    Type: Grant
    Filed: July 31, 1980
    Date of Patent: September 10, 1985
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takao Iwasaki, Higashi Ito, Seiichi Watanabe
  • 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: 4510341
    Abstract: Chloroprene is produced by a dehydrochlorination of 3,4-dichlorobutene-1 by contacting 3,4-dichlorobutene with a metal alkoxide of tetrahydrofurfuryl alcohol. The reaction mixture in a form of a slurry obtained by the dehydrochlorination is distilled to separate lower boiling components comprising chloroprene and the unreacted 3,4-dichlorobutene-1 as main components from higher boiling components comprising tetrahydrofurfuryl alcohol and a metal chloride as main components.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: April 9, 1985
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Itsuo Tabata, Seiichi Watanabe
  • Patent number: 4418232
    Abstract: Improvement in the catalytic dehydrohalogenation of a halogenated hydrocarbon to an ethylenically unsaturated product with aqueous alkali in a series of reactors in a cascade arrangement, wherein the fresh alkali feed is relocated from the first reactor to a reactor subsequent to the first, and partly spent alkali solution from the last reactor is recirculated to the first reactor, while the ethylenically unsaturated product is recovered from the effluent from the last reactor, and waste brine is removed from the effluent from the reactor immediately preceding that to which fresh alkali is fed. In this manner, the amount of both the alkali and the catalyst can be reduced, and the conversion is increased. Dehydrochlorination of 3,4-dichlorobutene-1 gives chloroprene, which is a valuable monomer for making synthetic elastomers.
    Type: Grant
    Filed: November 29, 1982
    Date of Patent: November 29, 1983
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventor: Louis J. Maurin, III
  • Patent number: 4384159
    Abstract: Saturated C.sub.1-6 hydrochlorocarbons are dehydrochlorinated by contacting with ZSM-5 or silicalite zeolites at 200.degree. C.-400.degree. C.
    Type: Grant
    Filed: March 12, 1982
    Date of Patent: May 17, 1983
    Assignee: The Dow Chemical Company
    Inventor: Ronald W. Diesen
  • Patent number: 4308410
    Abstract: Chloroprene is produced by continuous dehydrochlorinating 3,4-dichlorobutene- 1 at 40.degree.-70.degree. C. in two phase liquid mixture of water and alcohol with standing alkali metal hydroxide of not more than 10% by weight in aqueous phase and separating an organic liquid phase containing chloroprene from the resulting mixture.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: December 29, 1981
    Assignees: BP Chemicals Limited, Distugil S.A.
    Inventors: Antony H. P. Hall, Jean P. Merle
  • Patent number: RE31330
    Abstract: 1,1,1-Trihalogeno-4-methyl pentenes and 1,1-dihalogeno-4-methyl-1,3-pentadienes are produced. These compounds are of value as intermediates for the production of pyrethrin analogs which are of use as insecticides or agricultural chemicals.
    Type: Grant
    Filed: October 23, 1980
    Date of Patent: August 2, 1983
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoshiji Fujita, Yoshiaki Omura, Fumio Mori, Kazuo Itoi, Takashi Nishida, Yoshin Tamai, Sukeji Aihara, Takeo Hosogai, Fumio Wada