Processes Of Preparing, Purifying, Or Recovering Benzene Ring Containing Compound Patents (Class 570/190)
  • Patent number: 5180862
    Abstract: A process for isomerizing trichlorobenzene is disclosed. In the process of the present invention, a mixture of trichlorobenzene isomers containing 1,3,5-trichlorobenzene and/or 1,2,3-trichlorobenzene in small concentrations is contacted with a catalyst including acid type mordenite zeolite or acid type beta zeolite and a rhenium component and/or silver component in liquid phase in the presence of hydrogen, thereby increasing concentrations of 1,3,5-trichlorobenzene and/or 1,2,3-trichlorobenzene in said mixture.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: January 19, 1993
    Assignee: Toray Industries, Inc.
    Inventors: Kazuyoshi Iwayama, Hiroaki Honda
  • Patent number: 5177302
    Abstract: This invention is concerned with a process for separating isomers of disubstituted benzenes, wherein a mixture of isomers of disubstituted benzenes is contacted with a substituted cyclodextrin to form inclusion complexes, and desired isomers are recovered therefrom in a highly selective manner. The invention also provides substituted cyclodextrins suited for use in the process. Substituted cyclodextrins used in the process can be recovered and used repeatedly.
    Type: Grant
    Filed: May 22, 1991
    Date of Patent: January 5, 1993
    Assignees: Director-General, Agency of Industrial Science and Technology, Ensuiko Sugar Refining Co., Ltd.
    Inventors: Isamu Uemasu, Hideki Takahashi
  • Patent number: 5159082
    Abstract: A process for producing an aromatic compound is disclosed, which comprises coupling an aromatic sulfinic acid or a salt thereof with an aromatic halogen compound having at least one halogen atom attached to the carbon atom of the aromatic nucleus thereof or a vinyl group-containing halogen compound having at least one halogen atom attached to the carbon atom of said vinyl group in the presence of a catalyst compound containing an element selected from platinum metals.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: October 27, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Toru Okoshi
  • 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: 5110903
    Abstract: A process is provided for the preparation of a mixture of parylene dimers wherein the distribution of dimers within the mixture is predetermined by the proper selection of halogenated and non-halogenated 2,2-paracyclophane starting material. Since the dimers are free of alpha-halogens, the formation of environmentally undesirable acid halides during the deposition of parylene films and coatings is avoided. Since the dimers are useful in the preparation of inert, transparent, conformal coatings of parylene, desirable chemical and/or physical properties can be imparted to such coating by formation of a dimer mixture of a predetermined composition. The parylene film properties, composition and deposition conditions will be different by varying dimer distribution.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: May 5, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Chinsoo Lee, David R. Bassett
  • Patent number: 5107044
    Abstract: A process for the bromination of biphenyl, particularly for the preparation of 4-bromobiphenyl or of 4,4'-dibromobiphenyl. The process comprises reacting biphenyl with BrCl. The BrCl may be formed in situ in the reaction medium or may be formed before reaction with biphenyl.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: April 21, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventor: Alain Nonn
  • Patent number: 5105036
    Abstract: Aromatic hydrocarbons monosubstituted by straight-chain or branched C.sub.1 -C.sub.12 -alkyl or by Chd 3-C.sub.8 -cycloalkyl can be chlorinated in the aromatic ring in the liquid phase in the presence of Friedel-Crafts catalysts if cyclic amidines which are oxy-sustituted on the exocyclic N atom are employed as co-catalysts. An increased proportion of the p-isomer is obtained in this reaction.
    Type: Grant
    Filed: February 6, 1991
    Date of Patent: April 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 5087769
    Abstract: A method of forming 6-substituted-2-vinyl naphthalene from a 2-substituted naphthalene compound wherein the substituent in the 2-position is an ortho-para directing electron-donating group not reactive with hydrogen fluoride, comprises contacting the naphthalene compound and an acylating agent with substantially anhydrous hydrogen fluoride to acylate the naphthalene compound to a 6-substituted-2-acylnaphthalene compound, hydrogenating the 6-substituted-2-acylnaphthalene compound to convert the 2-acyl substituent to an alcohol substituent, dehydrating the product of hydrogenation in the presence of a free radical inhibitor to convert the alcohol substituent to an olefinic substituent, and isolating the formed 6-substituted-2-vinylnaphthalene subsequent to the dehydration.
    Type: Grant
    Filed: September 26, 1990
    Date of Patent: February 11, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Henry C. Linstid, III., Kenneth G. Davenport
  • Patent number: 5030777
    Abstract: A process for synthesizing 3,5-dichloroalkylbenzene and recovering 1,3-dichlorobenzene from a starting mixture of 1,3- and 1,4-dichlorobenzenes. The process includes the sequential steps of selectively alkylating the 1,3-dichlorobenzene in the starting mixture; isomerizing a portion of the 2,4-dichloroalkylbenzene produced to 3,5-dichloroalkylbenzene; separating the 1,4-dichlorobenzene from the isomeric mixture of dichlorocumenes; and selectively transalkylating the dichlorocumenes to yield alkylbenzene, 3,5-dichloroalkylbenzene and 1,3-dichlorobenzene. By selectively alkylating only a portion of the 1,3-dichlorobenzene, the reaction products are obtained in good yield and substantially free of undesirable by-products.
    Type: Grant
    Filed: October 31, 1989
    Date of Patent: July 9, 1991
    Assignee: Standard Chlorine of Delaware, Inc.
    Inventors: Jacob George, Kanti B. Desai, Jimmy Peress
  • Patent number: 5026931
    Abstract: Disclosed is a process comprising preparing a product stream rich in naphthalene and 2-monoiodonaphthalene comprising contacting hydrogen and a feed stream containing iodonaphthalenes selected from the group consisting of monoiodonaphthalene, diiodonaphthalene and triiodonaphthalene and mixtures thereof with an X or Y type zeolite containing an ion selected from the group consisting of sodium, potassium and rubidium and a metal selected from the group selected from the group consisting of palladium, platinum, rhodium and ruthenium.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: June 25, 1991
    Assignee: Eastman Kodak Company
    Inventors: Victor H. Agreda, Thomas H. Larkins, Jr.
  • Patent number: 5004848
    Abstract: A method for producing high melting hexabromocyclododecane product by selective recovery of preferred isomers.
    Type: Grant
    Filed: February 5, 1990
    Date of Patent: April 2, 1991
    Assignee: Ethyl Corporation
    Inventor: Phillip R. Beaver
  • Patent number: 4914247
    Abstract: A para-substituted halogenobenzene derivative is prepared by halogenating a benzene derivative in the liquid phase in the presence of a molded zeolite catalyst body comprising, based on the weight of the molded zeolite catalyst body, 10 to 95% by weight of an L-type zeolite as the anhydrous state and 5 to 90% by weight of amorphous silica.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: April 3, 1990
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Kazuhiko Sekizawa, Toshio Hironaka, Masao Nakano, Yukihiro Tsutsumi
  • 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: 4873383
    Abstract: A selective isolation of m-dichlorobenzene is carried out at a high efficiency by bringing an isomeric mixture containing m- and o- and/or p-dichlorobenzenes into contact with an absorbing material comprising a TPZ-3 type zeolite consisting of at least one aluminosilicate compound of the formula (I):M.sub.2/n O.multidot.Al.sub.2 O.sub.3 .multidot..sub.x SiO.sub.2 .multidot..sub.m H.sub.2 O (I)wherein M = a mono or di-valent cation, for example, H.sup.+, Li.sup.+ or Na.sup.+, n=1 or 2, x=10 or more, and m=0 or 1 or more, to selectively absorb dichlorobenzene by the absorbing material, and then, by collecting the non-absorbed fraction of the isomeric mixture.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: October 10, 1989
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Toshitaka Kaneshiki, Osamu Narukawa, Tadayoshi Haneda, Toshiyuki Endo
  • Patent number: 4849559
    Abstract: A process is provided for the preparation of the dimer, dichloro-[2,2]paracyclophane, which is useful as the starting material for the deposition of conformal parylene coatings employed, for example, in the electronics industry for the protection of various sensitive electronic components.The process avoids the normally low yields of chlorinated dimer formed by the chlorination of 2,2-paracyclophane and instead utilizes the Hofmann elimination of 2(3)-chloro-p-methylbenzyltrimethylammonium hydroxide by conducting the elimination reaction under carefully controlled conditions of reaction temperature and profile, reaction feed configuration, water concentration in the reactor and the use of a cosolvent, certain reaction promoters, or a combination thereof.
    Type: Grant
    Filed: May 15, 1987
    Date of Patent: July 18, 1989
    Assignee: Union Carbide Corporation
    Inventors: Chinsoo Lee, David R. Bassett
  • Patent number: 4832873
    Abstract: Polybrominated higher alkylbenzenes may be produced by reacting the corresponding hydrocarbon material with bromine chloride in an excess bromine reaction medium in the presence of an antimony halide catalyst.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: May 23, 1989
    Assignee: Great Lakes Chemical Corporation
    Inventors: Nicolai A. Favstritsky, Dennis M. Borden
  • Patent number: 4822928
    Abstract: Disclosed herein is a process for producing 2,5-dichlorotoluene which is useful as a monomer of heat-resistant polymers and an intermediate raw material for medicines, agricultrual chemicals and various organic synthetic substances, the process giving 2,5-dichlorotoluene at a high selectivity and in a high yield and comprising the steps of chlorinating 4-t-alkyltoluene or 4-isopropyltoluene in the presence of a catalyst, thereby obtaining a 2,5-dichlorocompound, and bringing the formed 2,5-dichlorocompound into contact with toluene in the presence of a catalyst, thereby subjecting the 2,5-dichlorocompound to transalkylation.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: April 18, 1989
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masashi Ohtsuru, Toshio Hozumi
  • Patent number: 4798913
    Abstract: A method for separating a trihalogenobenzene isomer from a mixture of at least two trihalogenobenzene isomers selected from the group consisting of 1,2,3-, 1,2,4- and 1,3,5-substituted isomers among trihalogenobenzenes represented by the formula: ##STR1## wherein X is Cl or Br, by means of a zeolite adsorber, characterized in that a ZSM-zeolite is used as the adsorber.
    Type: Grant
    Filed: January 5, 1988
    Date of Patent: January 17, 1989
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Kikuo Otomo, Masashi Yamagushi, Masami Ito, Hiroki Tokunaga
  • Patent number: 4704481
    Abstract: Benzylic and aromatic mercaptans are desulphurized by contacting the mercaptan with carbon monoxide at elevated temperatures in the presence of an aqueous hydrocarbon and a cobalt carbonyl catalyst.
    Type: Grant
    Filed: January 6, 1986
    Date of Patent: November 3, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, David J. H. Smith
  • Patent number: 4668832
    Abstract: Halogenated, unsaturated alcohols are dehydrated by contacting the alcohol and a carrier gas with a silica alumina catalyst to form dienes of the formula: ##STR1## wherein each X is independently hydrogen, fluorine chlorine, or bromine with the proviso that no more than one of them is hydrogen, and each R is independently hydrogen, alkyl, aralkyl, alkaryl, or aryl.
    Type: Grant
    Filed: October 8, 1985
    Date of Patent: May 26, 1987
    Assignee: The Dow Chemical Company
    Inventor: William J. Kruper, Jr.
  • Patent number: 4668835
    Abstract: The alkylation of para-substituted isopropyl benzenes with dipentenes employing an aluminum halide catalyst system produces novel tetracyclic compounds.
    Type: Grant
    Filed: October 4, 1985
    Date of Patent: May 26, 1987
    Assignee: Phillips Petroleum Co.
    Inventor: Raymond L. Cobb
  • Patent number: 4607116
    Abstract: Provided is a process for preparing a diaryl or a mixture of diaryls represented by any or a combination of the following formulae (II), (III) and (V), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted in a solvent in the presence of a transition metal catalyst and a reducing metal at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 -I.sup..sym. -Ar.sub.2 ]X.sup..crclbar. (I)Ar.sub.1 -Ar.sub.1 (II)Ar.sub.1 -Ar.sub.2 (III)Ar.sub.2 -Ar.sub.2 (IV)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups and X.sup..crclbar. is a counter ion which is inert to said reaction.
    Type: Grant
    Filed: March 8, 1984
    Date of Patent: August 19, 1986
    Assignee: Nippon Petrochemicals Company Limited
    Inventors: Yasuo Yamazaki, Takehiko Suzuki, Masaharu Uchiyama
  • Patent number: 4560814
    Abstract: Disclosed is a process for alkylating halogenated and trifluoromethylated benzene compounds. In that process, an alkyl halide is reacted with a benzene compound having two or three substituents selected from the group consisting of the halogens and the trifluoromethyl group, and also having a hydrogen atom whose two ortho positions are occupied by two of the said substituents. The reaction is carried out in the presence of at least one alkali metal amide and at least one agent that complexes with the cation of the alkali metal amide.
    Type: Grant
    Filed: January 31, 1984
    Date of Patent: December 24, 1985
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Gerard Soula
  • Patent number: 4554360
    Abstract: Provided is a process for converting an aromatic compound to prepare an iodoarene, Ar--I, and an aryl compound which is a compound wherein an unsaturated compound is bonded directly to an aryl group, Ar, which process comprises reacting a diaryliodonium salt represented by general formula (I)[Ar--I.sup..sym. --Ar]X.sup..crclbar. (I)wherein Ar is an aryl group which may be substituted and two Ar's are identical and X.sup..crclbar. is a counter ion inert to the reaction with the unsaturated compound in a solvent in the presence of a transition metal catalyst and a base or a reducing metal, said reaction being carried out at a temperature not higher than 80.degree. C. and/or by using at least one of the base, the reducing metal and the unsaturated compound in an amount not more than 1.
    Type: Grant
    Filed: March 29, 1984
    Date of Patent: November 19, 1985
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Yasuo Yamazaki, Takehiko Suzuki, Isoo Shimizu, Yasuo Matsumura
  • Patent number: 4538003
    Abstract: Process for the monoalkylation/monoarylation of dihaloaromatic compounds by treating the latter with selected magnesium or zinc organometallic reagents in the presence of a nickel/bidentate or tridentate phosphorus ligand. The products are intermediates to agricultural and pharmaceutical compounds.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: August 27, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Wilson Tam
  • Patent number: 4507513
    Abstract: A 3-halo-2-methylphenylmagnesium halide is cross-coupled with a halobenzene using nickel(II) acetylacetonate as catalyst, producing a 3-halo-2-methyl[1,1'-biphenyl]. The amount of catalyst should be greater than 0.01 mole percent, but not more than 0.1 mole percent, based on the 3-halo-2-methylphenylmagnesium halide to achieve the best yields.
    Type: Grant
    Filed: January 30, 1984
    Date of Patent: March 26, 1985
    Assignee: FMC Corporation
    Inventor: Eric G. DelMar
  • Patent number: 4465879
    Abstract: A 3-halo-2-methylphenylmagnesium halide is cross-coupled with a halobenzene under heterogeneous conditions using palladium metal as catalyst, producing a 3-halo-2-methyl[1,1'-biphenyl].
    Type: Grant
    Filed: August 19, 1983
    Date of Patent: August 14, 1984
    Assignee: FMC Corporation
    Inventor: Eric G. DelMar
  • Patent number: 4405792
    Abstract: 4-(Chlorophenyl)pyridines in which the chlorine atom is in the 3- or 4-position of the phenyl group are prepared by reacting a 4-vinyl pyridine with chloroprene to form a 4-(3- or 4-chlorocyclohex-3-enyl)pyridine and then catalytically dehydrogenating the 4-(3- or 4-chlorocyclohex-3-enyl)pyridine to form a 4-(3- or 4-chlorophenyl)pyridine. The 4-(3- and 4-monochlorocyclohex-3-enyl)pyridines are novel compounds.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: September 20, 1983
    Assignee: Ethyl Corporation
    Inventor: Thomas J. Walter
  • Patent number: 4371721
    Abstract: A process for selective cracking of 1,4-disubstituted benzene compounds having at least one polar substituent. Mixtures containing isomers of such a compound are brought into contact with a specified type of shape selective crystalline zeolite catalyst under conditions of temperature and pressure conducive to reaction of said benzene compound, thereby selectively reacting the 1,4-disubstituted isomer in preference to the 1,2- and 1,3-disubstituted isomers of said polar benzene compound. The shape selective zeolite catalysts employed herein are crystalline zeolites characterized by a silica to alumina ratio of at least about 12 and a constraint index within the approximate range of 1 to 12.
    Type: Grant
    Filed: September 25, 1981
    Date of Patent: February 1, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Margaret M. Wu
  • Patent number: 4329524
    Abstract: 3,5-Dichlorocumene is separated from a mixture comprising 3,5-dichlorocumene and 2,4-dichlorocumene by a process comprising contacting the mixture with an isopropyl group acceptor, in the presence of a catalyst comprising:(1) at least one Lewis acid compound, and(2) a proton source.The isopropyl group of 2,4-dichlorocumene is preferentially transferred, as compared to the isopropyl group of 3,5-dichlorocumene, to the acceptor forming a reaction product comprising an acceptor bearing the isopropyl group, 3,5-dichlorocumene and m-dichlorobenzene. 3,5-Dichlorocumene is readily separated from this reaction product by any conventional technique, typically distillation.
    Type: Grant
    Filed: March 12, 1980
    Date of Patent: May 11, 1982
    Assignee: The Dow Chemical Company
    Inventor: James R. Dewald
  • Patent number: 4328380
    Abstract: A novel process for the preparation of phenylpropyl halides of the formula ##STR1## by reacting the corresponding phenylpropyl halides, substituted only by R.sup.2 and R.sup.1, with an alcohol, alkyl halide or olefin; and phenylpropyl halides where R.sup.3 has certain meanings.
    Type: Grant
    Filed: August 8, 1980
    Date of Patent: May 4, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Norbert Goetz, Bernd Zeeh, Juergen Varwig
  • Patent number: 4284832
    Abstract: Tear gas or CS (o-Chlorobenzalmalononitrile) has two nitrile functional gps which, when removed, effects the chemical conversion of bulk CS to o-chlorostyrene. This involves a first step, an acid or base catalyzed hydrolysis of CS to o-chlorocinnamic acid. Thereafter a second reaction is the decarboxylation of the intermediate product to give o-chlorostyrene.CS is reacted with 70% sulfuric acid at 120.degree. C., producing ammonium sulfate and orth-ochlorocinnamic acid (the intermediate product). This intermediate product is separated and thermally decarboxylated at 270.degree. C. (with a catalytic amount of soda lime and copper powder) to ortho-chlorostyrene.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: August 18, 1981
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Solim S. W. Kwak
  • Patent number: 4250123
    Abstract: A novel process for the preparation of phenylpropyl halides of the formula ##STR1## by reacting the corresponding phenylpropyl halides, substituted only by R.sup.2 and R.sup.1, with an alcohol, alkyl halide or olefin; and phenylpropyl halides where R.sup.3 has certain meanings.
    Type: Grant
    Filed: May 11, 1979
    Date of Patent: February 10, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Norbert Goetz, Bernd Zeeh, Juergen Varwig