Isomerization Patents (Class 570/236)
  • Patent number: 10590052
    Abstract: 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: Grant
    Filed: June 26, 2018
    Date of Patent: March 17, 2020
    Assignee: ARKEMA FRANCE
    Inventors: Dominique Deur-Bert, Anne Pigamo, Philippe Bonnet
  • Patent number: 9221732
    Abstract: 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: Grant
    Filed: July 5, 2013
    Date of Patent: December 29, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Okamoto, Satoshi Yoshikawa, Fuyuhiko Sakyu
  • Patent number: 9162947
    Abstract: 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: Grant
    Filed: March 11, 2014
    Date of Patent: October 20, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9000239
    Abstract: 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: Grant
    Filed: March 14, 2013
    Date of Patent: April 7, 2015
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8822739
    Abstract: 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: Grant
    Filed: March 6, 2013
    Date of Patent: September 2, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventor: Mario Joseph Nappa
  • Patent number: 8779222
    Abstract: 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: Grant
    Filed: August 27, 2010
    Date of Patent: July 15, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Souda, Koji Hagiya
  • Patent number: 8461402
    Abstract: 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: Grant
    Filed: August 16, 2012
    Date of Patent: June 11, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Konstantin A. Pokrovski, Hsueh Sung Tung, Michael Van Der Puy
  • Patent number: 8288598
    Abstract: 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: Grant
    Filed: January 13, 2010
    Date of Patent: October 16, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Konstantin A. Pokrovski, Hsueh S. Tung, Michael Van Der Puy
  • Patent number: 8263818
    Abstract: 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: Grant
    Filed: January 13, 2010
    Date of Patent: September 11, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Konstantin A. Pokrovski, Hsueh S. Tung, Michael Van Der Puy
  • Patent number: 8217208
    Abstract: 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: Grant
    Filed: December 8, 2009
    Date of Patent: July 10, 2012
    Assignee: Honeywell International, Inc.
    Inventors: Ryan Hulse, Rajiv R. Singh, Konstantin A. Pokrovski, Hsueh Sung Tung, Daniel Merkel, Haiyou Wang, Michael Van Der Puy
  • Patent number: 8067650
    Abstract: 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: Grant
    Filed: July 10, 2007
    Date of Patent: November 29, 2011
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8058491
    Abstract: 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: Grant
    Filed: August 14, 2008
    Date of Patent: November 15, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Mario Joseph Nappa
  • Patent number: 8044252
    Abstract: 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: Grant
    Filed: July 11, 2007
    Date of Patent: October 25, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Donald J. Toton, Velliyur Nott Mallikarjuna Rao
  • Publication number: 20110218370
    Abstract: 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: Application
    Filed: November 12, 2009
    Publication date: September 8, 2011
    Applicant: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
  • Patent number: 7872163
    Abstract: 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: Grant
    Filed: December 16, 2009
    Date of Patent: January 18, 2011
    Assignee: DuPont Performance Elastomers L.L.C.
    Inventor: Jay Reimers
  • Patent number: 7709691
    Abstract: 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: Grant
    Filed: July 8, 2009
    Date of Patent: May 4, 2010
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7638660
    Abstract: An integrated process for the manufacture of HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze) by first catalytically dehydrofluorinating 1,1,1,3,3-pentafluoropropane to thereby produce a mixture of cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and hydrogen fluoride. Then optionally recovering hydrogen fluoride, catalytically isomerizing cis-1234ze into trans-1234ze, and recovering trans-1,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: January 5, 2009
    Date of Patent: December 29, 2009
    Assignee: Honeywell International Inc
    Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
  • Patent number: 7563936
    Abstract: 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: Grant
    Filed: October 27, 2006
    Date of Patent: July 21, 2009
    Assignee: Honeywell International Inc
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7485760
    Abstract: An integrated process for the manufacture of HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze) by first catalytically dehydrofluorinating 1,1,1,3,3-pentafluoropropane to thereby produce a mixture of cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and hydrogen fluoride. Then optionally recovering hydrogen fluoride, catalytically isomerizing cis-1234ze into trans-1234ze, and recovering trans-1,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: January 24, 2007
    Date of Patent: February 3, 2009
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
  • Patent number: 7268262
    Abstract: 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: Grant
    Filed: April 29, 2004
    Date of Patent: September 11, 2007
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Clark S. Graybill, Stephen R. Lester
  • Patent number: 6881872
    Abstract: 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: Grant
    Filed: March 27, 2003
    Date of Patent: April 19, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Tomoko Matsumoto, Tateo Nakano, Yutaka Yokoyama
  • Patent number: 6774270
    Abstract: 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: Grant
    Filed: April 1, 2003
    Date of Patent: August 10, 2004
    Assignee: 3M Innovative Properties Company
    Inventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
  • Patent number: 6392107
    Abstract: 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: Grant
    Filed: March 13, 2001
    Date of Patent: May 21, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventor: Peter Schertl
  • Publication number: 20010012910
    Abstract: 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: Application
    Filed: April 11, 2001
    Publication date: August 9, 2001
    Inventors: John David Scott, Charles Brian Blake, Paul Nicholas Ewing, Jeremy Charles Bauser Hunns, Steven Toplis, Andrew Neil Irwin, Mark Spruce
  • Patent number: 6034290
    Abstract: 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: Grant
    Filed: March 26, 1999
    Date of Patent: March 7, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 5763711
    Abstract: 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: Grant
    Filed: August 7, 1996
    Date of Patent: June 9, 1998
    Assignee: The Dow Chemical Company
    Inventor: Larry N. Ito
  • Patent number: 5510546
    Abstract: 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: Grant
    Filed: July 7, 1995
    Date of Patent: April 23, 1996
    Assignee: The Dow Chemical Company
    Inventor: Larry N. Ito
  • Patent number: 5072063
    Abstract: 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: Grant
    Filed: January 9, 1990
    Date of Patent: December 10, 1991
    Assignee: DowElanco
    Inventor: Peter Langensee
  • Patent number: 5051536
    Abstract: 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: Grant
    Filed: November 13, 1989
    Date of Patent: September 24, 1991
    Assignee: PPG Industries, Inc.
    Inventors: Earl M. Gorton, John D. Driskill, Randall M. Hall
  • Patent number: 4895993
    Abstract: 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: Grant
    Filed: September 15, 1988
    Date of Patent: January 23, 1990
    Assignee: Phillips Petroleum Company
    Inventors: H. Wayne Mark, Richard C. Doss, Clarence R. Bresson
  • Patent number: 4827059
    Abstract: 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: Grant
    Filed: July 8, 1988
    Date of Patent: May 2, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Alexander T. Harris, Donald A. Melchert, Jr.
  • Patent number: 4781807
    Abstract: 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: Grant
    Filed: November 28, 1986
    Date of Patent: November 1, 1988
    Assignee: National Distillers and Chemical Corporation
    Inventors: Clarence E. Clark, Jr., Richard G. Fayter, Jr.
  • Patent number: 4761507
    Abstract: 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: Grant
    Filed: June 28, 1985
    Date of Patent: August 2, 1988
    Assignee: Union Camp Corporation
    Inventors: Peter W. D. Mitchell, Lois T. McElligott, David E. Sasser
  • Patent number: 4704489
    Abstract: 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: Grant
    Filed: June 28, 1985
    Date of Patent: November 3, 1987
    Assignee: Union Camp Corporation
    Inventor: Lois T. McElligott
  • Patent number: 4704486
    Abstract: 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: Grant
    Filed: June 28, 1985
    Date of Patent: November 3, 1987
    Assignee: Union Camp Corporation
    Inventor: Lois T. McElligott
  • 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: 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: 4461920
    Abstract: 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: Grant
    Filed: February 12, 1980
    Date of Patent: July 24, 1984
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Higashi Ito, Seiichi Watanabe
  • Patent number: 4328381
    Abstract: 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: Grant
    Filed: December 2, 1980
    Date of Patent: May 4, 1982
    Assignee: Denki Kaguku Kogyo Kabushiki Kaisha
    Inventors: Itsuo Tabata, Seiichi Watanabe, Masayuki Shinoyama
  • 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