Including Chemical Reaction With By-product Hydrogen Halide Patents (Class 570/229)
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Patent number: 9732017Abstract: 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: GrantFiled: July 28, 2014Date of Patent: August 15, 2017Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Ivan Wlassics, Marco Colladon, Stefano Millefanti, Giuseppe Marchionni, Marco Piccinini
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Patent number: 9475739Abstract: 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: GrantFiled: August 1, 2012Date of Patent: October 25, 2016Assignee: BLUE CUBE IP LLCInventors: Max M. Tirtowidjojo, Barry B. Fish, David S. Laitar
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Patent number: 9403741Abstract: 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: GrantFiled: March 7, 2014Date of Patent: August 2, 2016Assignee: BLUE CUBE IP LLCInventors: Max M. Tirtowidjojo, David S. Laitar, Matthew L. Grandbois, William J. Kruper, Jr., Edward M. Calverley
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Patent number: 8907149Abstract: 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: GrantFiled: May 18, 2012Date of Patent: December 9, 2014Assignee: Dow Global Technologies LLCInventors: Max M. Tirtowidjojo, William J. Kruper, Jr., Barry B. Fish, David S. Laitar
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Patent number: 8907147Abstract: 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: GrantFiled: January 30, 2014Date of Patent: December 9, 2014Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung, Joshua Close, Terris Tianxue Yang
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Patent number: 8877990Abstract: A process of making a chlorinated hydrocarbon through a thermal dehydrochlorination step in which an unsaturated compound represented by the following general formula (2) is obtained by thermally decomposing a saturated compound represented by the following general formula (1). CCl3—CCl2-mHm—CCl3-nHn??(1) CCl2?CCl2-mHm-1—CCl3-nHn??(2) (in the above formulas, m is 1 or 2, and n is an integer of 0 to 3.Type: GrantFiled: June 17, 2010Date of Patent: November 4, 2014Assignee: Tokuyama CorporationInventors: Tadahiro Fukuju, Kikuo Yamamoto, Masayuki Moriwaki, Yasutaka Komatsu, Akihiro Saito, Shunsuke Hosaka, Dai Tsunoda, Jun Kawakami
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Publication number: 20140163265Abstract: 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: ApplicationFiled: August 1, 2012Publication date: June 12, 2014Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Max M. Tirtowidjojo, Barry B. Fish, David S. Laitar
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Patent number: 8258355Abstract: 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: GrantFiled: July 24, 2008Date of Patent: September 4, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh S. Tung, Michael Van Der Puy, Jing Ji Ma
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Patent number: 8115038Abstract: 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: GrantFiled: December 17, 2008Date of Patent: February 14, 2012Assignee: Occidental Chemical CorporationInventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
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Publication number: 20090216055Abstract: 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: ApplicationFiled: December 17, 2008Publication date: August 27, 2009Inventors: Richard L. Wilson, Rodney D. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
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Patent number: 5705720Abstract: 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: GrantFiled: June 7, 1995Date of Patent: January 6, 1998Assignee: AtochemInventors: Claude Demaiziere, Jean Lesparre, Yves Correia
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Patent number: 5672792Abstract: 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: GrantFiled: September 19, 1994Date of Patent: September 30, 1997Assignee: Enichem Elastomeres France SAInventors: Jean-Pierre Tassara, Michel Baudouin
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Patent number: 5659093Abstract: 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: GrantFiled: June 27, 1995Date of Patent: August 19, 1997Assignee: Daikin Industries Ltd.Inventors: Seiji Takubo, Hirokazu Aoyama, Tatsuo Nakada
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Patent number: 5545781Abstract: 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: GrantFiled: September 19, 1994Date of Patent: August 13, 1996Assignee: Enichem Elastomeres France S.A.Inventors: Michel Baudouin, Jean-Pierre Tassara
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Patent number: 5176897Abstract: 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: GrantFiled: June 12, 1991Date of Patent: January 5, 1993Assignee: Allied-Signal Inc.Inventor: George R. Lester
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Patent number: 5151263Abstract: 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: GrantFiled: July 25, 1990Date of Patent: September 29, 1992Assignee: Dupont-Mitsui Fluorochemicals Co., Ltd.Inventors: Susumu Okazaki, Akito Kurosaki
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Patent number: 5118492Abstract: 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: GrantFiled: July 16, 1990Date of Patent: June 2, 1992Assignee: Dupont-Mitsui Fluorochemicals Co., Ltd.Inventors: Susumu Okazaki, Akito Kurosaki
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Patent number: 4650914Abstract: 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: GrantFiled: January 9, 1985Date of Patent: March 17, 1987Assignee: Monsanto CompanyInventor: Scott S. Woodard
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Patent number: 4629816Abstract: 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: GrantFiled: March 1, 1983Date of Patent: December 16, 1986Assignee: Bayer AktiengesellschaftInventors: Josef Heinrich, Rudolf Casper, Manfred Beck
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Patent number: 4605800Abstract: 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: GrantFiled: January 17, 1983Date of Patent: August 12, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Joseph F. Englert, Jr., Louis J. Maurin, III, Clare A. Stewart, Jr.
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Patent number: 4540838Abstract: 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: GrantFiled: July 31, 1980Date of Patent: September 10, 1985Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Takao Iwasaki, Higashi Ito, Seiichi Watanabe
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Patent number: 4535194Abstract: 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: GrantFiled: July 6, 1983Date of Patent: August 13, 1985Assignee: Monsanto Co.Inventor: Scott S. Woodard
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Patent number: 4510341Abstract: 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: GrantFiled: May 7, 1980Date of Patent: April 9, 1985Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Itsuo Tabata, Seiichi Watanabe
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Patent number: 4418232Abstract: 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: GrantFiled: November 29, 1982Date of Patent: November 29, 1983Assignee: E. I. Du Pont de Nemours & Co.Inventor: Louis J. Maurin, III
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Patent number: 4384159Abstract: Saturated C.sub.1-6 hydrochlorocarbons are dehydrochlorinated by contacting with ZSM-5 or silicalite zeolites at 200.degree. C.-400.degree. C.Type: GrantFiled: March 12, 1982Date of Patent: May 17, 1983Assignee: The Dow Chemical CompanyInventor: Ronald W. Diesen
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Patent number: 4308410Abstract: 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: GrantFiled: May 12, 1978Date of Patent: December 29, 1981Assignees: BP Chemicals Limited, Distugil S.A.Inventors: Antony H. P. Hall, Jean P. Merle
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Patent number: RE31330Abstract: 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: GrantFiled: October 23, 1980Date of Patent: August 2, 1983Assignee: Kuraray Co., Ltd.Inventors: Yoshiji Fujita, Yoshiaki Omura, Fumio Mori, Kazuo Itoi, Takashi Nishida, Yoshin Tamai, Sukeji Aihara, Takeo Hosogai, Fumio Wada