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.
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.
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.
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.
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.
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
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.
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.
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
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
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.
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.
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.
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.
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.
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
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.
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.
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.
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.
Abstract: The alkylation of para-substituted isopropyl benzenes with dipentenes employing an aluminum halide catalyst system produces novel tetracyclic compounds.
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.
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.
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.
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.
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.
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].
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.
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.
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.
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
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
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