Isomerization Patents (Class 570/236)
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Patent number: 10590052Abstract: A process for producing a main (hydro)halocarbon compound, including the formation of a mixture of compounds including hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene and one or more other (hydro)halocarbon compounds, distillation of this mixture making it possible to collect, firstly, an azeotropic composition, and, secondly, at least one of the compounds of the mixture. The (hydro) halocarbon compounds are preferably selected among tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes.Type: GrantFiled: June 26, 2018Date of Patent: March 17, 2020Assignee: ARKEMA FRANCEInventors: Dominique Deur-Bert, Anne Pigamo, Philippe Bonnet
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Patent number: 9221732Abstract: A separation method of 1-chloro-3,3,3-tetraluofopropene and hydrogen fluoride according to the present invention includes reducing the hydrogen chloride content of a mixture containing hydrogen chloride, 1-chloro-3,3,3-tetrafluoropropene and hydrogen fluoride, thereby causing phase separation of the mixture so as to obtain an upper phase predominantly containing the hydrogen fluoride and a lower phase predominantly containing the 1-chloro-3,3,3-tetrafluoropropene. This separation method is industrially economically advantageous since the 1-chloro-3,3,3-tetraluofopropene and the hydrogen fluoride can be separated rapidly by simple operation.Type: GrantFiled: July 5, 2013Date of Patent: December 29, 2015Assignee: Central Glass Company, LimitedInventors: Satoru Okamoto, Satoshi Yoshikawa, Fuyuhiko Sakyu
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Patent number: 9162947Abstract: Disclosed are processes for a high temperature isomerization reaction converting (E)-1-chloro-3,3,3-trifluoropropene to (Z)-1-chloro-3,3,3-trifluoropropene. In certain aspects of the invention, such a process includes contacting a feed stream with a heated surface, where the feed stream includes (E)-1-chloro-3,3,3-trifluoropropene or mixture of (E)-1-chloro-3,3,3-trifluoropropene with (Z)-1-chloro-3,3,3-trifluoropropene. The resulting product stream includes (Z)-1-chloro-3,3,3-trifluoropropene and (E)-1-chloro-3,3,3-trifluoropropene, where the ratio of (Z) isomer to (E) isomer in the product stream is higher than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.Type: GrantFiled: March 11, 2014Date of Patent: October 20, 2015Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung
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Patent number: 9000239Abstract: The present invention provides processes for the production of HCFO-1233zd, 1-chloro-3,3,3-trifluoropropene, from the starting material, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf). In a first process, HCFO-1233zd is produced by the isomerization of HCFO-1233xf. In a second process, HCFO-1233zd is produced in a two-step procedure which includes (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne; and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd.Type: GrantFiled: March 14, 2013Date of Patent: April 7, 2015Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 8822739Abstract: An isomerization process is disclosed. The process involves contacting 2,3,3,3-tetrafluoropropene with a suitable catalyst in a reaction zone to produce a product mixture comprising 1,3,3,3-tetrafluoropropene.Type: GrantFiled: March 6, 2013Date of Patent: September 2, 2014Assignee: E I du Pont de Nemours and CompanyInventor: Mario Joseph Nappa
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Patent number: 8779222Abstract: A production method of 1,1,3-trichloro-1-propene comprising the following steps A and B; Step A: 1,1,1,3-tetrachloropropane is dehydrochlorinated at a temperature between 30° C. and 50° C. in the presence of at least one base selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, and a phase transfer catalyst, Step B: 3,3,3-trichloro-1-propene obtained in the step A is isomerized into 1,1,3-trichloro-1-propene in the presence of a metal catalyst.Type: GrantFiled: August 27, 2010Date of Patent: July 15, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Souda, Koji Hagiya
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Patent number: 8461402Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.Type: GrantFiled: August 16, 2012Date of Patent: June 11, 2013Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Konstantin A. Pokrovski, Hsueh Sung Tung, Michael Van Der Puy
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Patent number: 8288598Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.Type: GrantFiled: January 13, 2010Date of Patent: October 16, 2012Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Konstantin A. Pokrovski, Hsueh S. Tung, Michael Van Der Puy
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Patent number: 8263818Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.Type: GrantFiled: January 13, 2010Date of Patent: September 11, 2012Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Konstantin A. Pokrovski, Hsueh S. Tung, Michael Van Der Puy
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Patent number: 8217208Abstract: Disclosed are processes for an isomerization reaction between (E)1-chloro-3,3,3-trifluoropropene and (Z)1-chloro-3,3,3-trifluoropropene. Some of the disclosed processes include the step of contacting a feed stream with a heated surface, where the feed stream includes (E)1-chloro-3,3,3-trifluoropropene, (Z)1-chloro-3,3,3-trifluoropropene or mixtures thereof. The resulting product stream includes (E)1-chloro-3,3,3-trifluoropropene and (Z)1-chloro-3,3,3-trifluoropropene, where the ratio of (E) isomer to (Z) isomer in the product stream is different than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.Type: GrantFiled: December 8, 2009Date of Patent: July 10, 2012Assignee: Honeywell International, Inc.Inventors: Ryan Hulse, Rajiv R. Singh, Konstantin A. Pokrovski, Hsueh Sung Tung, Daniel Merkel, Haiyou Wang, Michael Van Der Puy
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Patent number: 8067650Abstract: This invention relates a process for the manufacture of the HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze). More particularly, the invention pertains to a process for the manufacture of the HFO trans-1234ze by first 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 and then recovering trans-1,3,3,3-tetrafluoropropene.Type: GrantFiled: July 10, 2007Date of Patent: November 29, 2011Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 8058491Abstract: A starting material comprising 1,2,3,3,3-pentafluoropropene is contacted with an aluminum chlorofluoride (AlClxF3-x) catalyst to obtain a final product wherein the Z/E ratio of 1,2,3,3,3-pentafluoropropene is either increased or decreased relative to the Z/E ratio of 1,2,3,3,3-pentafluoropropene in said starting material.Type: GrantFiled: August 14, 2008Date of Patent: November 15, 2011Assignee: E. I. du Pont de Nemours and CompanyInventor: Mario Joseph Nappa
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Patent number: 8044252Abstract: A process is disclosed to increase the Z/E ratio of 1,2,3,3,3-pentafluoropropene. The process involves contacting a starting material comprising 1,2,3,3,3-pentafluoropropene with a catalyst on AlF3 or carbon, wherein the catalyst is selected from the group consisting of SbClwF5-w, TiClxF4-x, SnClyF4-y and TaCl2F5-z wherein w is from 0 to 4, x is from 0 to 3, y is from 0 to 3, z is from 0 to 4, to obtain a product wherein the Z/E ratio of 1,2,3,3,3-pentafluoropropene is increased relative to the Z/E ratio of 1,2,3,3,3-pentafluoropropene in the starting material. A process is also disclosed to decrease the Z/E ratio of 1,2,3,3,3-pentafluoropropene.Type: GrantFiled: July 11, 2007Date of Patent: October 25, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Donald J. Toton, Velliyur Nott Mallikarjuna Rao
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Publication number: 20110218370Abstract: The present invention provides a process for the manufacture of trans 1-chloro-3,3,3-trifluoropropene (E-1233zd). The first step of the process comprises the fluorination of 1,1,3,3-tetrachlororopropene (1230za, CCh?CH—CHCh) and/or 1,1,1,3,3-pentaachloropropane (240fa) to a mixture of cis 1233zd (Z-1233zd) and trans 1233zd (E-1233zd). The second step of the process comprises a separation of the mixture formed in the first step to isolate cis 1233zd (Z-1233zd) from the mixture. The third step of the process comprises isomerization of cis 1233zd (Z-1233zd) to trans 1233zd (E-1233zd).Type: ApplicationFiled: November 12, 2009Publication date: September 8, 2011Applicant: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
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Patent number: 7872163Abstract: 3,4-Dichlorobutene-1 is produced by a process comprising the step of contacting 1,4-dichlorobutene-2 with either 1) a ferric carboxylate catalyst of the formula where R is an alkyl or alkenyl group of 4-18 carbon atoms, a cycloalkyl or cycloalkenyl group of 6-18 carbon atoms or an aryl group selected from phenyl, benzyl, xylyl, tolyl, and naphthyl groups, whereby a portion of the 1,4-dichlorobutene-2 is isomerized to form 3,4-dichlorobutene-1, or 2) a ferric carboxylate catalyst of the formula where R, R? and R? are independently alkyl or alkenyl groups of 4-18 carbon atoms, cycloalkyl or cycloalkenyl groups of 6-18 carbon atoms or aryl groups selected from phenyl, benzyl, xylyl, tolyl, and naphthyl groups, the sum of m, n and o is 3 and m, n and o are independently 0, 1 or 2, whereby a portion of the 1,4-dichlorobutene-2 is isomerized to form 3,4-dichlorobutene-1.Type: GrantFiled: December 16, 2009Date of Patent: January 18, 2011Assignee: DuPont Performance Elastomers L.L.C.Inventor: Jay Reimers
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Patent number: 7709691Abstract: Disclosed are processes for the conversion of isomerizable halogenated C2-C6 olefins from one geometric form to a more preferred geometric form. Preferred process aspects comprise converting C2-C6 olefin in a cis-form to a trans-form comprising exposing the cis-form of the compound, preferably contained in process stream, to conditions effective to convert at least about 50 percent, and even more preferably at least about 70 percent, of the cis-form compound to the trans-form compound. Preferably the catalyst comprises at least one Lewis acid metal fluoride.Type: GrantFiled: July 8, 2009Date of Patent: May 4, 2010Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 7638660Abstract: 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: GrantFiled: January 5, 2009Date of Patent: December 29, 2009Assignee: Honeywell International IncInventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
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Patent number: 7563936Abstract: Disclosed are processes for the conversion of isomerizable halogenated C2-C6 olefins from one geometric form to a more preferred geometric form. Preferred process aspects involve converting C2-C6 olefin in a cis-form to a trans-form under conditions effective to convert at least about 50 percent, and even more preferably at least about 70 percent, of the cis-form compound to the trans-form compound. In preferred embodiments the C2-C6 olefin comprises tetrafluoropropene, with cis-1,3,3,3 tetrafluoropropene (cis-HFO-1234ze) being converted, preferably at high conversion rates and high selectivity, to trans-1,3,3,3 tetrafluoropropene (trans-HFO-1234ze).Type: GrantFiled: October 27, 2006Date of Patent: July 21, 2009Assignee: Honeywell International IncInventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 7485760Abstract: 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: GrantFiled: January 24, 2007Date of Patent: February 3, 2009Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
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Patent number: 7268262Abstract: Describes a method for recovering trans-1,2-dichloroethene from a liquid feed composition comprising both the cis-and trans-isomers of 1,2-dichloroethene and contaminating amounts of other chlorinated hydrocarbons, e.g., lower alkyl chlorinated hydrocarbons, such as C1-C2 chlorinated hydrocarbons. In one of the described methods, the liquid feed composition is introduced into a first distillation column 10 wherein the stereoisomers and chlorinated hydrocarbons more volatile than the stereoisomers are removed as overhead 12 and charged to a second distillation column 20. In column 20, the stereoisomers are separated from the more volatile chlorinated hydrocarbons, and a bottoms fraction 24 comprising the stereoisomers is charged to a reactive distillation column 30 wherein the cis-isomer is isomerized to the trans-isomer in the liquid phase and in the presence of an organic free-radical initiator, e.g., an azonitrile initiator.Type: GrantFiled: April 29, 2004Date of Patent: September 11, 2007Assignee: PPG Industries Ohio, Inc.Inventors: Clark S. Graybill, Stephen R. Lester
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Patent number: 6881872Abstract: Less colored trans-1,3-dichloropropene and a process for producing it, are presented. A composition comprising cis-1,3-dichloropropene, trans-1,3-dichloropropene and C6 compounds, is subjected to a distillation step and to a step of reacting chlorine or bromine, to remove cis-1,3-dichloropropene as a low boiling component, and then the residue is distilled to remove the chlorinated C6 compounds as a high boiling component and to obtain trans-1,3-dichloropropene as a low boiling component.Type: GrantFiled: March 27, 2003Date of Patent: April 19, 2005Assignee: Asahi Glass Company, LimitedInventors: Tomoko Matsumoto, Tateo Nakano, Yutaka Yokoyama
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Patent number: 6774270Abstract: A method of removing hexafluoropropylene dimers (“HFP dimers”), dimer hydrides and other oligomers from a fluid is described. The method comprises heating the fluid to isomerize the HFP dimers to the thermodynamic isomer, and contacting the fluid with a tertiary amine (or salts thereof) to form a hexafluoropropylene dimer—tertiary amine adduct. The method may further comprise the step of separating the dimer adducts from the reaction mixture.Type: GrantFiled: April 1, 2003Date of Patent: August 10, 2004Assignee: 3M Innovative Properties CompanyInventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
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Patent number: 6392107Abstract: This invention relates to a process for isomerizing 1,4-dichloro-2-butene to yield 3,4-dichloro-1-butene or 3,4-dichloro-1-butene to yield 1,4-dichloro-2-butene, characterized in that the catalyst used comprises a compound of the formula CpFe(CO)2X, wherein Cp denotes a cyclopentadienyl derivative of the general formula (I), wherein R1 to R5 mutually independently denote H, C1 to C12 alkyl, C5 to C8 cycloalkyl, which may in turn bear C1 to C12 alkyl groups, C6 to C14 aryl, alkylaryl, arylalkyl, wherein two adjacent residues may together form saturated or unsaturated C3 to C14 cycles, or denote—SiR6R7R8, wherein R6 to R7 may mutually independently mean C1 to C4 alkyl, C5 to C8 cycloalkyl or C6 to C14 aryl, and X denotes F, Cl, Br.Type: GrantFiled: March 13, 2001Date of Patent: May 21, 2002Assignee: Bayer AktiengesellschaftInventor: Peter Schertl
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Publication number: 20010012910Abstract: Prior to carrying out a gaseous phase chemical reaction, a liquid phase organic compound which is prone to degrade is vaporized at elevated pressures with the aid of a second compound. In one embodiment of the invention, vaporization is effected by co-vaporizing a mixture of the two compounds in a vaporizer. In another embodiment, the first compound is injected into a hot gaseous stream and undergoes atomization into droplets which then vaporize within the gaseous stream. The second compound is used to assist the atomization process and/or to sweep atomized droplets of the first compound away from hot surfaces where the first compound would otherwise tend to undergo degradation if the droplets are allowed to reside in contact with such surfaces.Type: ApplicationFiled: April 11, 2001Publication date: August 9, 2001Inventors: John David Scott, Charles Brian Blake, Paul Nicholas Ewing, Jeremy Charles Bauser Hunns, Steven Toplis, Andrew Neil Irwin, Mark Spruce
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Patent number: 6034290Abstract: Porous microcomposites comprising a perfluorinated ion-exchange polymer (PFIEP) containing pendant metal cation exchanged sulfonate groups, metal cation exchanged carboxylate groups, or metal cation exchanged sulfonate and carboxylate groups, wherein the metal cation may be ligand coordinated, and optionally pendant sulfonic acid groups, carboxylic acid groups, or sulfonic acid and carboxylic acid groups, the PFIEP being entrapped within and highly dispersed throughout a network of metal oxide, a network of silica or a network of metal oxide and silica can be prepared from PFIEP and one or more precursors selected from the group consisting of a metal oxide precursor, a silica precursor, and a metal oxide and silica precursor using an in situ process. Preferred metal cations are Cr, Sn, Al, Fe, Os, Co, Zn, Hg, Li, Na, Cu, Pd or Ru. Such microcomposites have a first set of pores having a pore size diameter ranging from about 0.Type: GrantFiled: March 26, 1999Date of Patent: March 7, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 5763711Abstract: A process for converting 3,3-dichloropropene in an intermediate boiling byproduct stream from a process of making allyl chloride by the chlorination of propylene to cis- or trans-1,3-dichloropropene or a mixture of these, wherein the 3,3-dichloropropene is contacted in the liquid phase with an alumina, silica or zeolite catalyst, characterized in that the alumina, silica or zeolite catalyst is selected to possess a predominance of basic sites as associated with a high alkali or alkaline earth metals content, for increased conversion and productivity and reduced catalyst deactivation rates.Type: GrantFiled: August 7, 1996Date of Patent: June 9, 1998Assignee: The Dow Chemical CompanyInventor: Larry N. Ito
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Patent number: 5510546Abstract: An improved process for converting 3,3-dichloropropene in an intermediate boiling byproduct stream from a process of making allyl chloride by the chlorination of propylene to cis- or trans-1,3-dichloropropene or a mixture of these, wherein the intermediate boiling byproduct stream is processed batchwise or continuously to dry the stream to a water content of less than about 15 parts per million by weight, and then is contacted in the liquid phase with an alumina, silica or zeolite catalyst under conditions effective to carry out the conversion.Type: GrantFiled: July 7, 1995Date of Patent: April 23, 1996Assignee: The Dow Chemical CompanyInventor: Larry N. Ito
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Patent number: 5072063Abstract: Cis- and trans-1,3-dichloropropenes and their homologs and 1,3-dibromopropenes can be prepared by isomerizing the corresponding 3,3-dihalopropene or homolog thereof in a simple, high yield process by contacting the latter with an effective silica, alumina, or zeolite catalyst. Thus, a mixture of cis- and trans-1,3-dichloropropenes is produced in good yield and with good selectivity when a mixture of 3,3-dichloropropene with other chlorinated hydrocarbons, principally 1,2-dichloropropane, is contacted with an acidic activated alumina catalyst at a temperature of about 100.degree. C.Type: GrantFiled: January 9, 1990Date of Patent: December 10, 1991Assignee: DowElancoInventor: Peter Langensee
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Patent number: 5051536Abstract: One stereoisomer of 1,2-dichloroethene is isomerized to the other stereoisomer in the liquid phase and in the presence of free radical initiator.Type: GrantFiled: November 13, 1989Date of Patent: September 24, 1991Assignee: PPG Industries, Inc.Inventors: Earl M. Gorton, John D. Driskill, Randall M. Hall
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Patent number: 4895993Abstract: An isomerization of a haloalkene is conducted in the presence of a mixture of a copper compound and a trithiocarbonic acid derivative or dithiocarbonic acid derivative.Type: GrantFiled: September 15, 1988Date of Patent: January 23, 1990Assignee: Phillips Petroleum CompanyInventors: H. Wayne Mark, Richard C. Doss, Clarence R. Bresson
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Patent number: 4827059Abstract: Formation of solid and/or high boiling residues during the isomerization of one of 1,4-dichlorobutene-2 and 3,4-dichlorobutene-1 into each other in the presence of a cuprous chloride catalyst is inhibited by the addition to the isomerization reaction of a small amount of a hydroxylamine salt.Type: GrantFiled: July 8, 1988Date of Patent: May 2, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Alexander T. Harris, Donald A. Melchert, Jr.
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Patent number: 4781807Abstract: This invention relates to an efficient cis-to-trans isomerization of 1,4-dihalobutene-2 by means of a thiol or hydrogen bromide or hydrogen chloride catalyzed reaction.Type: GrantFiled: November 28, 1986Date of Patent: November 1, 1988Assignee: National Distillers and Chemical CorporationInventors: Clarence E. Clark, Jr., Richard G. Fayter, Jr.
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Patent number: 4761507Abstract: A method for the isomerization of linalyl halides is disclosed, improved by the presence of an organic quaternary salt. The improved method of the invention requires less energy for completion of the isomerization and shortens the isomerization times.Type: GrantFiled: June 28, 1985Date of Patent: August 2, 1988Assignee: Union Camp CorporationInventors: Peter W. D. Mitchell, Lois T. McElligott, David E. Sasser
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Patent number: 4704489Abstract: A method for the isomerization of linalyl halides is disclosed, improved by the presence of an alcohol. The improved method of the invention requires less energy for completion of the isomerization and shortens the isomerization times.Type: GrantFiled: June 28, 1985Date of Patent: November 3, 1987Assignee: Union Camp CorporationInventor: Lois T. McElligott
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Patent number: 4704486Abstract: The disclosure is of an improved process for the hydrohalogenation of myrcene in the presence of a catalyst, which comprises carrying out the hydrohalogenation in the presence of an alcohol.Type: GrantFiled: June 28, 1985Date of Patent: November 3, 1987Assignee: Union Camp CorporationInventor: Lois T. McElligott
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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: 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: 4461920Abstract: 3,4-Dichlorobutene-1 and 1,4-dichlorobutene-2 are isomerized in the presence of a catalyst of a combination of a copper compound or copper metal and at least one additive from the group of 1,3-diphenylguanidine, di-o-tolylguanidine, glycine ethyl ester hydrochloride and 2-amino-4-chlorophenol.Type: GrantFiled: February 12, 1980Date of Patent: July 24, 1984Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Higashi Ito, Seiichi Watanabe
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Patent number: 4328381Abstract: An isomerization between 3,4-dichlorobutene-1 and 1,4-dichlorobutene-2 is carried out in the presence of a catalyst for isomerization as a combination of a copper compound and a dithiocarbamic acid derivative. The dithiocarbamic acid derivative is a compound having the formula ##STR1## wherein R and R' are the same and different and respectively represent a C.sub.1 -C.sub.8 alkyl group or an aryl group and M represents hydrogen atom or a metal atom or ammonium group and R" represents a C.sub.1 -C.sub.8 alkyl group, an aryl group or a heterocyclic group such as mercaptobenzothiazole.Type: GrantFiled: December 2, 1980Date of Patent: May 4, 1982Assignee: Denki Kaguku Kogyo Kabushiki KaishaInventors: Itsuo Tabata, Seiichi Watanabe, Masayuki Shinoyama
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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