Processes Of Preparing, Purifying, Or Recovering Unsaturated Compound Patents (Class 570/216)
  • Patent number: 5663472
    Abstract: A process for reacting ethane with chlorine to produce a mixture of ethylene and vinyl chloride is disclosed. The process involves the intimate mixing of ethane and chlorine in an ethane to chlorine ratio of at least about 0.9:1 at a temperature such that ethane and chlorine do not react during mixing, and heating the mixture to a temperature above about 215.degree. C. to commence the reaction, allowing the reaction to proceed for a period of less than about 1 minute, and providing sufficient heat to the reacting mixture so that the reacted mixture will have a temperature between about 400.degree. C. and about 800.degree. C.
    Type: Grant
    Filed: February 7, 1995
    Date of Patent: September 2, 1997
    Assignee: University of Southern California
    Inventors: Sidney W. Benson, Maja A. Weissman
  • Patent number: 5600042
    Abstract: The purpose of this invention is to describe a new process for the manufacture of choroethene (C.sub.2 H.sub.3 Cl). This new process involves the use or ethylene (C.sub.2 H.sub.4) as a feedstock. Highly chlorinated ethenes or methanes are used as chlorinating agents. The corresponding less chlorinated ethenes or methanes are recovered as co-products or recycled to the process to produce additional chloroethene. The distribution of the products may be adjusted so that chloroethene is the major product.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: February 4, 1997
    Inventors: Wu-Chi Chen, Harvey R. Chen
  • Patent number: 5476979
    Abstract: A process for converting a chlorinated alkene feedstock including two or more chlorines to reaction products including a less-chlorinated alkene in a commercially substantial proportion, comprising reacting the chlorinated alkene feedstock with hydrogen in the presence of a catalyst consisting essentially of a Group VIII metal other than rhodium, palladium or ruthenium and a Group IB metal on a support.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: December 19, 1995
    Assignee: The Dow Chemical Company
    Inventors: Larry N. Ito, Craig B. Murchison, Michael T. Holbrook, A. Dale Harley, David D. Smith
  • Patent number: 5453557
    Abstract: A process for the catalytic conversion of various chlorinated hydrocarbon byproducts and waste products especially to less chlorinated, useful or salable products, in which a chlorinated hydrocarbon feedstock containing two or more chlorines is reacted with hydrogen in the presence of a catalyst consisting essentially of an active hydrogenating metal component such as platinum in elemental or compound form, and a surface segregating metal component such as copper in elemental or compound form on a support.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: September 26, 1995
    Assignee: The Dow Chemical Company
    Inventors: A. Dale Harley, Michael T. Holbrook, David D. Smith, Mark D. Cisneros, Larry N. Ito, Craig B. Murchison
  • Patent number: 5449833
    Abstract: A novel process for the preparation of a chlorinated polyolefin having excellent low temperature characteristics and brightness is provided which comprises allowing a polyolefin dissolved or suspended in a solvent to undergo chlorination reaction with chlorine gas or chlorinated sulfuryl in the presence of a radical initiator as a catalyst, characterized in that as said solvent there is used 1,1,2-trichloroethane and the temperature is controlled to 90.degree. C. or lower at the process for removing hydrogen chloride and/or sulfur dioxide by-produced during the reaction from the reaction system.
    Type: Grant
    Filed: September 26, 1994
    Date of Patent: September 12, 1995
    Assignee: Tosoh Corporation
    Inventors: Nobuyuki Ito, Katsushige Okayama, Yoshinori Karasuda, Yasumichi Miyagawa
  • Patent number: 5446203
    Abstract: Alternative methods for synthesizing haloenones and haloakenes and their use as starting materials for synthesis of substituted or unsubstituted alkyl and aryl substituted enones and alkenes, including tamoxifen and tamoxifen analogs, using such haloenones and haloalkenes.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: August 29, 1995
    Assignee: New York University
    Inventor: Edward McNelis
  • Patent number: 5243109
    Abstract: Tribromostyrene (TBS) is produced by the preparation of a TBS precursor, which is .beta.-bromoethyl-tribromobenzene (.beta.-BrBr.sub.3), and the successive elimination of hydrogen bromide from said precursor. The precursor is prepared by selective bromination of phenethyl bromide (.beta.-Br), wherein the molar ratio of bromine to phenethyl bromide is comprised between 2.5 and 3.5, and preferably between 3.1 and 3.3 included; and by adding bromine, after an initial addition, at a controlled molar rate.
    Type: Grant
    Filed: August 6, 1992
    Date of Patent: September 7, 1993
    Assignee: Bromine Compounds Ltd.
    Inventors: Nurit Kornberg, David Beneish, Michael Peled
  • Patent number: 5196617
    Abstract: A process for hydrodehalogenating halogenated organic compounds present in a contaminated aqueous environmental source in which the halogenated organic compounds are reacted with hydrogen gas or a source of hydrogen gas in the presence of a catalyst of palladium on carbon.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: March 23, 1993
    Assignee: Engelhard Corporation
    Inventors: Suphan Kovenklioglu, Edward N. Balko, Jeffrey B. Hoke, Robert J. Farrauto, Gary A. Gramiccioni
  • Patent number: 5138107
    Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of (i) a phase transfer catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 LJ where L is selected from the group consisting of phosphorus and nitrogen, where J is an inorganic anion other than fluoride, and where R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: August 11, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Yoel Sasson
  • Patent number: 5132475
    Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of a quaternary ammonium fluoride catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 NF where R.sup.1, R.sup.2, and R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrocarbyl radicals containing from 1 to about 20 carbon atoms.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: July 21, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Yoel Sasson
  • Patent number: 5113028
    Abstract: A process for mixing hot ethane with chlorine gas using a mixer consisting of a main pipe through which ethane is conducted, and four or more jets through which chlorine gas is introduced into the main pipe. The angle between the axis of each jet and the line from the center point to the point where the axis of each jet makes contact with the inside surface of the main pipe ranges between about 30.degree. to 45.degree..
    Type: Grant
    Filed: August 1, 1991
    Date of Patent: May 12, 1992
    Inventors: Hang-Chang B. Chen, Gerald F. Achee
  • 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: 4918252
    Abstract: A novel and efficient synthetic route is proposed for the preparation of (Z,E)-9,12-tetradecadienyl acetate as a sex pheromone compound used for population control of the pest insects belonging to the genus of Spodoptera via an intermediate 1-halo-(Z,E)-7,10-dodecadiene, which is a novel compound not known in the prior art. This novel compound is synthesized by reacting a Grignard reagent XMgC.tbd.C(CH.sub.2).sub.6 X,X being Cl or Br, with (E)-2-butenyl chloride or bromide to form an ene-yne compound of the formula CH.sub.3 CH.dbd..sup.(E) CHCH.sub.2 C.tbd.C(CH.sub.2).sub.6 X and then partially hydrogenating this ene-yne compound.
    Type: Grant
    Filed: February 5, 1989
    Date of Patent: April 17, 1990
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Akira Yamamoto
  • Patent number: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4870220
    Abstract: A method for manufacturing methallyl chloride by reacting isobutene with chlorine in the gas phase is disclosed. The reaction is carried out in a distributed nozzle-mixing reactor which enables the reaction to proceed in a stabile manner even without addition of oxygen. At the same time, the yield of methallyl chloride is increased.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: September 26, 1989
    Assignee: Huels Aktiengesellschaft
    Inventors: Julius Jabrik, Gerhard Sticken, Rolf Viehweger
  • Patent number: 4814522
    Abstract: Catalyzed halogen exchange between perhaloolefins to form products of the formulas:R.sup.1 R.sup.2 C=CR.sup.3 R.sup.8andR.sup.5 R.sup.6 C=CR.sup.7 R.sup.4wherein R.sup.1, R.sup.2, R.sup.3, R.sup.5, Rhu 6l , and R.sup.7 are individually selected from the group F, Cl, Br, C.sub.1 to C.sub.4 perfluoroalkyl, and pentafluorophenyl; or R.sup.1 and R.sup.3, R.sup.2 and R.sup.3, R.sup.5 and R.sup.7, R.sup.6 and R.sup.7 together, with the proviso that both groups are in the cis configuration, are selected from the group perfluoroalkylene of 2 to 4 carbons ando--C.sub.6 F.sub.4 (--)CF.sub.2 --,R.sup.8 =F, R.sup.4 =Cl or Br; and wherein none of the fluoroolefins simultaneously contains both Cl and Br.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: March 21, 1989
    Assignee: E. I. DuPont DeNemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 4760211
    Abstract: A process for recovering brominated acenaphthylene and its condensate in the form of powder, comprising dropping a solution of brominated acenaphthylene and its condensate produced from acenaphthene by reactions of bromination, condensation and dehydrobromination into hot water containing a carboxylic acid ester of polyoxyalkylene sorbitan, while the solvent is being distilled off, to recover the brominated acenaphthylene and its condensate in the form of powder dispersed in water.
    Type: Grant
    Filed: September 18, 1986
    Date of Patent: July 26, 1988
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Masahige Kubo, Koji Kawabata, Yukihiro Tsutsumi
  • Patent number: 4747914
    Abstract: A process for the purification of 1,2-dichloroethane is described, in which the crude product, containing not more than 3% by weight of high-boilers, is distilled in a first column at 125.degree. to 180.degree. C. in such a way that the bottom product contains not more than 7% by weight of high-boilers. The purified, vaporous 1,2-dichloroethane discharged at the head of this column is used to heat product streams containing 1,2-dichloroethane. The bottom product from the first column is distilled in a second column, advantageously at a pressure of 5 to 40 kPa, together with a feed composed of vaporous 1,2-dichloroethane obtained from the reaction of ethylene with chlorine. The process makes it possible to purify 1,2-dichloroethane with a saving in energy.
    Type: Grant
    Filed: May 27, 1986
    Date of Patent: May 31, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Schwarzmaier, Walter Frohlich, Wenzel Kuhn, Josef Riedl, Iwo Schaffelhofer, Erich Mittermaier, Reinhard Krumbock
  • Patent number: 4734534
    Abstract: Novel alumina-supported nickel boride catalysts prepared by the borohydride promoted reduction of nickel arsenate are described. Method of catalyst preparation and process for hydrogenation of acetylenic and diolefinic compounds employing the invention catalysts are also described.
    Type: Grant
    Filed: February 5, 1986
    Date of Patent: March 29, 1988
    Assignee: Phillips Petroleum Company
    Inventor: Ted H. Cymbaluk
  • Patent number: 4716255
    Abstract: 3,3-dichloro-2-methylpropene is prepared by reacting 1-chloro-2-methylpropene with sulfuryl chloride in the presence of a catalytically effective amount of nitrogen-containing bases or phosphines. Suitable nitrogen-containing bases are preferably aliphatic, aromatic and heterocyclic amines, as well as mixtures thereof; suitable phosphines are preferably aliphatic or aromatic phosphines.
    Type: Grant
    Filed: August 27, 1984
    Date of Patent: December 29, 1987
    Assignee: Huels Aktiengesellschaft
    Inventor: Dieter J. Muller
  • Patent number: 4605797
    Abstract: Selective hydrogenation process is provided employing as catalyst a composition consisting essentially of elemental palladium on calcium carbonate support with lead acetate and an aromatic amine oxide. Very high selectivities to cis-olefinic compounds from acetylenic compounds is achieved employing the catalyst of the invention.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: August 12, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4599469
    Abstract: Process for the hydrogenation of functionally substituted acetylenic compounds employing catalyst comprising nickel boride on an inorganic oxide support is disclosed. Functionally-substituted acetylenic compounds are selectively reduced under mild reaction conditions to give functionally-substituted cis-olefinic compounds in high yield.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: July 8, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Ted H. Cymbaluk, Jim D. Byers, Marvin M. Johnson
  • Patent number: 4587367
    Abstract: Cis- and trans-1,3-dichloro-2-methylpropene and 3-chloro-2-chloromethylpropene are produced by the reaction of 3-chloro-2-methylpropene with sulfuryl chloride in the presence of catalytic amounts of amines and/or phosphines.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: May 6, 1986
    Assignee: Huels Aktiengesellschaft
    Inventor: Dieter J. Mueller
  • Patent number: 4571438
    Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
    Type: Grant
    Filed: March 21, 1985
    Date of Patent: February 18, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Dennis S. Banasiak
  • Patent number: 4540826
    Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: September 10, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Dennis S. Banasiak, Jim D. Byers
  • Patent number: 4400550
    Abstract: A process for the synthesis of (Z,Z)-11-13-hexadecadienal is disclosed, starting with undecylenic alcohol.
    Type: Grant
    Filed: February 12, 1982
    Date of Patent: August 23, 1983
    Assignee: Albany International Corp.
    Inventors: Clyde E. Bishop, Gary W. Morrow
  • Patent number: 4329483
    Abstract: A method for preparing cyclotetrasiloxane, aliphatic chlorides and/or acyl chlorides from a chlorosilane and an acyloxy compound is disclosed. The chlorosilane and the acyloxy compound may be present as substantially equimolar amounts of separate compounds or they may be present in the same molecule in equimolar amounts. The reactants are merely heated sufficiently, with or without a soluble halide salt catalyst, to form the products. Advantageously this method can provide cyclotetrasiloxanes having water-sensitive radicals such as silicon-bonded chlorine atoms and/or silicon-bonded acyl chloride radicals.
    Type: Grant
    Filed: July 10, 1981
    Date of Patent: May 11, 1982
    Assignee: Dow Corning Corporation
    Inventor: John L. Speier
  • Patent number: 4329482
    Abstract: A method for preparing cyclotetrasiloxane, aliphatic chlorides and/or acyl chlorides from a cyclotrisiloxane, a chlorosilane and an acyloxy compound is disclosed. The chlorosilane and the acyloxy compound may be present as substantially equimolar amounts of separate compounds or they may be present in the same molecule in equimolar amounts. The reactants are merely heated sufficiently, with or without a soluble halide salt catalyst, to form the products. Advantageously this method can provide cyclotetrasiloxanes having water-sensitive radicals such as silicon-bonded chlorine atoms and/or silicon-bonded acyl chloride radicals. This method also provides a method for preparing cyclotetrasiloxanes having either one type of siloxane unit (non-mixed cyclotetrasiloxanes) or more than one type of siloxane unit (mixed cyclotetrasiloxanes).
    Type: Grant
    Filed: July 10, 1981
    Date of Patent: May 11, 1982
    Assignee: Dow Corning Corporation
    Inventor: Maher Y. A. I. Elsheikh
  • Patent number: 4329525
    Abstract: A compound is chlorinated with chlorine to produce chlorinated product and hydrogen chloride byproduct. Recovered hydrogen chloride byproduct is contacted with oxygen and a molten salt mixture containing the higher and lower valent chlorides of a multivalent metal, such as cuprous and cupric chloride, to effect recovery of the hydrogen chloride by enriching the molten salt content of the higher valent chloride. The molten salt, enriched in higher valent chloride, is then dechlorinated by use of a stripping gas, preferably hydrogen chloride, to produce a gaseous effluent containing stripped chlorine and the stripping gas, which is then recycled to the chlorination step. The presence of stripping gas, as a diluent, improves the chlorination operation.
    Type: Grant
    Filed: February 21, 1978
    Date of Patent: May 11, 1982
    Assignee: The Lummus Company
    Inventors: Herbert Riegel, Vincent Strangio, Morgan C. Sze
  • Patent number: 4307243
    Abstract: Conversion of esters (R.sup.1)(R.sup.2)C(C Hal.sub.3)OX, X being-P Hal.sub.2, --C(O)OR.sup.3 or ##STR1## R.sup.1, R.sup.3 and R.sup.4 being optionally substituted hydrocarbyl groups and R.sup.2 methyl or hydrogen, with zinc in acetic acid gives a very high yield of a dihalovinyl compound (R.sup.1)(R.sup.2)C.dbd.C Hal.sub.2, e.g., of the ethyl ester of the parent acid of pyrethroid insecticides.
    Type: Grant
    Filed: March 25, 1980
    Date of Patent: December 22, 1981
    Assignee: Shell Oil Company
    Inventors: Petrus A. Kramer, Pieter A. Verbrugge
  • Patent number: 4269780
    Abstract: A process for forming non-polymeric disproportionation products of non-conjugated olefins using catalysts comprising (1) at least one of certain neutral carbene complexes, and (2) at least one of certain compounds of Groups IVa, IVb, Vb, VIb, VIIb, VIII, and Ib of the Periodic Table of the Elements.
    Type: Grant
    Filed: December 6, 1979
    Date of Patent: May 26, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Dennis S. Banasiak