Halogen Containing Reactant (e.g., Dehydrohalogenation, Etc.) Patents (Class 568/323)
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Patent number: 5298664Abstract: The present invention relates to the production of aryl ketones. Specifically the invention relates to the production of aryl ketones by reaction of aromatic hydrocarbon compounds and aromatic or aliphatic acyl halides in the presence of anhydrous iron (III) chloride. In particular, the invention relates to reaction under conditions of elevated temperature and pressure. Preferred embodiments of the invention specifically relate to the synthesis of benzophenone, methylbenzophenone and dimethylbenzophenone.Type: GrantFiled: April 30, 1992Date of Patent: March 29, 1994Assignee: Velsicol Chemical CorporationInventors: Arlice E. Rains, Terry E. Lea, David I. Templer
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Patent number: 5296636Abstract: A process for the preparation of 2,4,6-trimethylbenzoic acid of the formula I ##STR1## in which .alpha.-chloro-2,4,6-trimethylacetophenone is reacted with an alkali hydroxide solution and chlorine in the presence of a phase-transfer catalyst at a temperature ranging from 0.degree. to 150.degree. C. and a pressure ranging from 0.01 to 50 bar, and a process for the preparation of 2,4,6-trimethylbenzoic acid I, in which .alpha.-chloro-2.4.6-trimethylacetophenone of the formula II ##STR2## is reacted with 1,3,5-trimethylbenzene and chloroacetyl chloride in the presence of a catalyst at a temperature ranging from 0.degree. to 150.degree. C. and a pressure ranging from 0.01 to 50 bar, the catalyst used being an iron oxide.Type: GrantFiled: January 28, 1993Date of Patent: March 22, 1994Assignee: BASF AktiengesellschaftInventors: Wolfgang Siegel, Rudolf Kropp, Jochen Schroeder
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Patent number: 5288915Abstract: Ketones are prepared by admixing at least one gem-dichloro compound with at least one acid such that the ketone wherein the keto-oxygen replaces the gem-dichloro group is formed. The reaction is exemplified by the reaction of 9,9-dichlorofluorene with an acid such that fluorenone is formed. This process has the advantage that no oxidizing agent is used.Type: GrantFiled: December 17, 1992Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventor: Marlin E. Walters
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Patent number: 5258547Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.Type: GrantFiled: January 9, 1992Date of Patent: November 2, 1993Assignee: Imperial Chemical Industries plcInventor: Gary N. Sheldrake
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Patent number: 5235000Abstract: This invention relates to a process for reducing the formation of carbonyl halide in bromine chloride and to an improved process for the bromination of compounds with BrCl in the presence of a carbonyl halide poisonable catalyst.Type: GrantFiled: December 10, 1990Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventor: Bonnie G. McKinnie
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Patent number: 5210313Abstract: A method for preparing isomerically pure 2,5-dichlorobenzophenones in good to high yields is provided. The invention comprises Friedel-Crafts aroylation of 1,4-dichlorobenzene using an aroyl halide or aromatic anhydride and at least one Lewis acid, the latter being present in an amount of at least about 1.1 mole per mole of aroyl halide or aromatic anhydride, preferably about 1.5 moles per mole of aroyl halide or aromatic anhydride and, more preferably, from about 2 to about 2.5 moles of Lewis acid per mole of aroyl halide or aromatic anhydride. Preferably, the molar ratio of 1,4-dichlorobenzene to aroyl halide ranges from about 1.2:1 to about 8:1.Type: GrantFiled: January 10, 1992Date of Patent: May 11, 1993Assignee: Maxdem IncorporatedInventors: Ying Wang, Mark S. Trimmer
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Patent number: 5208383Abstract: A process for producing an aromatic acylation product from an aromatic compound, an olefin and carbon monoxide, which comprises the steps of:(a) reacting an olefin with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride at a pressure of not more than 100 kg/cm.sup.Type: GrantFiled: January 24, 1992Date of Patent: May 4, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tadayoshi Takefumi, Yoshihiro Shiokawa, Shunichi Matsumoto, Nobuyuki Tokura
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Patent number: 5196607Abstract: A novel multi-step process for preparing the (4S)-enantiomer of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone in a highly-optically pure form is disclosed. The process involves (1) first reacting 3,4-dichlorocinnamyl chloride with L-(-)-ephedrine in a chlorinated lower hydrocarbon solvent to form the corresponding chiral N-methyl-N-(.beta.-hydroxy-.beta.-phenylisopropyl)-3-(3,4-dichlorophenyl)p ropenoamide; (2) then subjecting the chiral .alpha.,.beta.-unsaturated amide formed in the first step to a Grignard reaction with phenyl magnesium chloride or bromide, followed by hydrolysis, to effect a conjugate addition of the phenyl group and the hydrogen element to the aforesaid .alpha.,.beta.-unsaturated propenoamide and so selectively form the corresponding chiral N-methyl-N-(.beta.-hydroxy-.beta.Type: GrantFiled: February 14, 1992Date of Patent: March 23, 1993Assignee: Pfizer Inc.Inventor: George J. Quallich
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Patent number: 5194636Abstract: In the preparation of benzyl ketones of the formula ##STR1## a benzyl chloride of the formula ##STR2## is reacted with an acid chloride of the formulaR.sup.6 --CO--Cl (III)a) in a first stage with an excess of zinc powder in the presence of a diluent at a temperature between 80.degree. C. and 200.degree. C. under an inert gas atmosphere, and separating off the excess zinc powder, thereby to obtain a benzyl derivative of the formula ##STR3## and b) in a second stage reacting the benzyl derivative of the formula (IV) with an acid chloride of the formula (III) in the presence of a palladium catalyst and in the presence of a diluent at a temperature between 0.degree. C. and 150.degree. C. under an inert gas atmosphere.Type: GrantFiled: March 3, 1992Date of Patent: March 16, 1993Assignee: Bayer AktiengesellschaftInventors: Thomas Himmler, Udo Kraatz, Wolfgang Kramer, Klaus Stroech
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Patent number: 5191133Abstract: The selective formation of 2-acetonaphthalene is achieved by acetylating naphthalene in the presence of liquid hydrogen fluoride. The 2-acetonaphthalene can be separated from the formed 1-acetonaphthalene isomer by successive hydrogenation of the isomer mixture and dehydration. The hydrogenation is selective to the 2-isomer while the 1-acetonaphthalene remains unreacted. Upon completion, 2-vinylnaphthalene can be distilled off from the unreacted 1-acetonaphthalene.Type: GrantFiled: May 22, 1991Date of Patent: March 2, 1993Assignee: Hoescht Celanese CorporationInventor: Henry C. Linstid, III
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Patent number: 5185469Abstract: A continuous process is disclosed for the acylation or alkylation of aromatic compounds in hydrogen fluoride. The aromatic compound is sufficiently insoluble in hydrogen fluoride that a two phase reaction medium forms. However, surprisingly, the product acylated or alkylated aromatic compound is soluble in hydrogen fluoride. The present invention particularly relates to use of a continuous, multi-stage process for carrying out the acylation or alkylation reaction. In the multi-stage process, the continuous phase can be either the hydrogen-fluoride rich phase or the aromatic compound-rich phase. The movement of the continuous phase relative to the non-continuous (dispersed) phase can be countercurrent or concurrent. The multi-stage process can be operated in a manner such that the aromatic compound feed to the reaction is entirely consumed or such that unreacted aromatic compound is recycled.Type: GrantFiled: August 23, 1991Date of Patent: February 9, 1993Assignee: Hoechst Celanese Corp.Inventors: Daniel D. Lindley, Timothy R. Ryan, Thomas A. Curtis, Edward M. De la Garza, Charles R. Hilton, Thomas M. Kenesson
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Patent number: 5162587Abstract: The present invention provides a novel compound represented as ##STR1## The present novel compound is prepared by reacting fluorine with pyridine-boron trifluoride and is useful as a fluorinating agent in the fluorination of organic compounds.Type: GrantFiled: October 18, 1991Date of Patent: November 10, 1992Assignee: Allied-Signal Inc.Inventors: Michael Van Der Puy, David Nalewajek, George A. Shia, William J. Wagner
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Patent number: 5146001Abstract: In the preparation of benzyl ketones of the formula ##STR1## a benzyl chloride of the formula ##STR2## is reacted with an acid chloride of the formulaR.sup.6 --CO--Cl (III)a) in a first stage with an excess of zinc powder in the presence of a diluent at a temperature between 80.degree. C. and 200.degree. C. under an inert gas atmosphere, and separating off the excess zinc powder, thereby to obtain a benzyl derivative of the formula ##STR3## and b) in a second stage reacting the benzyl derivative of the formual (IV) with an acid chloride of the formula (III) in the presence of a palladium catalyst and in the presence of a diluent at a temperature between 0.degree. C. and 150.degree. C. under an inert gas atmosphere.Type: GrantFiled: June 3, 1991Date of Patent: September 8, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Himmler, Udo Kraatz, Wolfgang Kramer, Klaus Stroech
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Patent number: 5144070Abstract: Disclosed is a process for the preparation of .alpha.-iodocarbonyl compounds such as .alpha.-iodocarboxylic acid anhydrides and .alpha.-iodoketones by the reaction of a carboxylic anhydride with molecular iodine. Hydrolysis of the .alpha.-iodocarboxylic acid anhydrides gives the corresponding .alpha.-iodocarboxylic acids.Type: GrantFiled: August 30, 1989Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier
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Patent number: 5138098Abstract: A regioselective acylation process is provided for coverting a 2-methylnaphthalene compound to a 2-acetyl-6-methylnaphthalene compound. The process is conducted under liquid phase conditions in an acylation inert solvent using a complexing agent which is regiospecific for the beta position of naphthalene and which is a thermally stable nitrohydrocarbon compound. Preferred such agents are nitrobenzene, o-nitrotoluene, and mesitylene. Also provided is a novel method for producing a 2-acetyl-6-methylnaphthalene compound of relatively high purity from isomer mixtures by recrystallization from a hydrocarbon solvent, such as n-octane, isooctane, or n-nonane.Type: GrantFiled: March 14, 1991Date of Patent: August 11, 1992Assignee: Amoco CorporationInventors: Gary P. Hagen, Gregory E. Schmidt, John M. Weis, Thomas G. Smith
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Patent number: 5118860Abstract: In accordance with the present invention, aromatic ketones are prepared by the acylation of aromatic reactants using boron trifluoride as a catalyst and in a solvent medium comprising anhydrous liquid sulfur dioxide. The acylation proceeds in accordance with the equation I: ##STR1## wherein n ranges from 5 to 9, Ar is phenylene and n is 5, naphthalene and n is 7, or a bis phenylene radical having the structure: ##STR2## and n is 9; wherein Z is selected from the group consisting of a covalent carbon to carbon bond, O, S, SO.sub.2, C.dbd.O and C.sub.1 to C.sub.3 alkylene or alkylidene, X is selected from the group consisting of H, OH, halogen, C.sub.1 to C.sub.6 alkyl C.sub.1 to C.sub.6 alkoxy and combinations thereof, R is an alkyl group containing from 1 to about 16 carbon atoms and Y is selected from the group consisting of hydroxy, acyloxy and halogen.Type: GrantFiled: November 27, 1990Date of Patent: June 2, 1992Assignee: Hoechst Celanese CorporationInventor: Charlet R. Lindley
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Patent number: 5118839Abstract: A process for preparing nitro substituted polyarylketones of the formula: ##STR1## is disclosed. The process involves the condensation of ##STR2## where R.sub.A is hydrogen, --COOH, or C.sup.1 to C.sub.12 linear or branched alkyl, Y and Y' are the same or different and are a chemical bond ##STR3## or --Si(CH.sub.3).sub.2 -- and m is 0 or 1 and X is halo. These nitro groups of these compounds can be reduced to provide the corresponding amines, which are useful for the preparation of thermally stable high melting polyimides.Type: GrantFiled: September 4, 1990Date of Patent: June 2, 1992Assignee: Ethyl CorporationInventors: Allan A. Eisenbraun, Venkataraman Ramachandran
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Patent number: 5113020Abstract: The present invention provides a process for producing a p-halogenobenzophenone derivative of a high purity in a high yield at a low cost in the presence of a repeatedly usable catalyst having a long life and free from the problem of waste water treatment without using any chemical of a strong toxicity. According to the present invention, the p-halogenobenzophenone derivative is produced by reacting an (un)substituted benzotrichloride of the following formula (I) with a halogenobezene of the following formula (II) in the presence of a catalyst selected from the group consisting of alumina, nickel sulfate, zirconium oxide, amorphous silica/alumina and a mixture of two or more of them or a catalyst obtained by treating these compounds with an acid and hydrolyzing the resulting bisphenyldichloromethane of the following formula (III): ##STR1## wherein X represents a halogen atom or a hydrogen atom and Y represents a halogen atom.Type: GrantFiled: August 28, 1991Date of Patent: May 12, 1992Assignee: Kureha Kagaku Kogyo K.K.Inventors: Kazuhiko Sunagawa, Nobuyuki Kusano
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Patent number: 5093529Abstract: In the process for the preparation of fluorinated benzoic acids of the formula I ##STR1## in which X and Y, for example, independently of one another denote chlorine or fluorine and X moreover denotes bromine, a fluorinated chloroacetophenone of the formula II ##STR2## in which Z denotes chlorine or hydrogen, is reacted with a hypohalite.Type: GrantFiled: July 16, 1990Date of Patent: March 3, 1992Assignee: Cassella AktiengesellschaftInventor: Horst Schmand
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Patent number: 5093532Abstract: Halogenomethylketones are prepared from nitro compounds by treating the latter in alcoholic solution with sodium alkoxide or potassium alkoxide, cooling to a temperature in the range -10.degree. to -100.degree. C. and then allowing the mixture to react with ozone at -10.degree. to -100.degree. C. The process is particularly suitable for the preparation of 1,1,1-trifluoroacetone from 1,1,1-trifluoro-2-nitropropane.Type: GrantFiled: July 31, 1991Date of Patent: March 3, 1992Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Jens Lorentzen
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Patent number: 5068447Abstract: Aromatic carbonyl compounds, in particular arylene ether ketones, are prepared by reacting an appropriate reagent system in the presence of free Lewis acid and a complex between a Lewis acid, for example, aluminum trichloride, and an inorganic salt controlling agent, for example, lithium chloride, and, optionally, a diluent, such as methylene chloride. The process is particularly advantageous for the preparation of substantially or all para-linked arylene ether ketones as the presence of the Lewis acid/Lewis base complex markedly reduces alkylation and ensures the substantial absence of ortho substitution.Type: GrantFiled: July 6, 1990Date of Patent: November 26, 1991Assignee: Raychem CorporationInventors: Heinrich C. Gors, Patrick J. Horner, Viktors Jansons
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Patent number: 5026917Abstract: A regioselective acetylation process is provided for converting a 2-methylnaphthalene compound to a 2-acetyl-6-methylnaphthalene compound. The process is conducted under liquid phase conditions using a new complexing agent which is regiospecific for the beta position of naphthalene and which is an electron-rich, carbon-based compound. A preferred such agent is hexamethylbenzene. Also provided is a novel method for producing a 2-acetyl-6-methylnaphthalene compound of relative high purity from isomer mixtures by recrystallization from a hydrocarbon solvent, such as n-octane, isooctane, or n-nonane.Type: GrantFiled: March 1, 1990Date of Patent: June 25, 1991Assignee: Amoco CorporationInventors: Gary P. Hagen, Gregory E. Schmidt, John M. Weis, Thomas G. Smith
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Patent number: 4983774Abstract: The preparation of ketones by reacting an acylating agent with an organo-manganous compound is catalyzed by a copper compound.Type: GrantFiled: December 16, 1988Date of Patent: January 8, 1991Assignee: Societe Nationale Elf AquitaineInventors: Gerard Cahiez, Blandine Laboue, Pierre Tozzolino
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Patent number: 4982006Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.Type: GrantFiled: May 1, 1989Date of Patent: January 1, 1991Assignee: Norwich Eaton Pharmaceuticals, Inc.Inventor: Thomas T. Hudec
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Patent number: 4978798Abstract: Disclosed is a method of making a bisphenyl dihalomethane by reacting a trihalomethylbenzene with a halobenzene and a Lewis acid. The bisphenyl dihalomethane can than be reacted with water to form a halobenzophenone. In an optical third step ring chlorines that are present can be replaced with fluorines and, in a final step, any remaining chlorines can be removed to leave a fluorobenzophenone. The process is particularly useful in making 4,4'-difluorobenzophenone, which is in turn useful in making polyetheretherketones.Type: GrantFiled: November 13, 1989Date of Patent: December 18, 1990Assignee: Occidental Chemical CorporationInventor: Jeffrey S. Stults
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Patent number: 4968845Abstract: A process for the preparation of halogen-containing aromatic compounds of the formula ##STR1## wherein Hal represents fluorine, chlorine or bromine and Z represents an aromatic group which comprises reacting a halobenzene of the formula C.sub.6 H.sub.5 Hal (II) under anhydrous conditions with a halide of a bisacid having the formula Hal-CO-Z-CO-Hal (III) in a molar ratio of at least 2:1 in the presence of a haloalkane sulfonic acid of the formula Y(C.sub.n X.sub.2n)SO.sub.3 H (IV), in formulae II and III Hal and Z having the afore-mentioned meaning and Y representing fluorine or hydrogen, X at least one of fluorine and chlorine, but at least one X being fluorine, and n being an integer of from 1 to 10.The said bis-(4-halobenzoyl) compounds being useful monomers for chemically resistant plastics which are still resistant even at high temperatures.Type: GrantFiled: March 7, 1989Date of Patent: November 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Joachim Hackenbruch, Theodor Papenfuhs, Klaus Warning, Gunter Siegemund
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Patent number: 4967011Abstract: The present invention relates to a process for decomposing an aromatic acylated compound.HF-BF.sub.3 complex in preparing an aromatic acylated compound by decomposing an aromatic acylated compound.HF-BF.sub.3 complex obtained by reacting an aromatic compound with an acylating agent in the presence of HF-BF.sub.3 as a catalyst, which comprises subjecting the aromatic acylated compound.HF-BF.sub.3 complex to thermal decomposition in the presence of at least one aromatic hydrocarbon (A.H.) selected from benzene, toluene and chlorobenzene and at least one saturated aliphatic hydrocarbon (S.H.) selected from pentane, hexane and cyclohexane, as a decomposing agent.Type: GrantFiled: August 11, 1989Date of Patent: October 30, 1990Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Nobuyuki Tokura, Tadayoshi Takefumi, Shunichi Matsumoto, Tatsuhiko Yanagawa, Yoshihiro Shiokawa, Ichiyo Ohtsuka
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Patent number: 4960945Abstract: The present invention relates to a process for the production of halobenzophenone derivatives represented by the following formula (II): ##STR1## wherein X and Y are the same or different and are independently F, Cl, Br or I, m stands for an integer of from 1 to 4 and n stands for an integer of from 0 to 4. The process comprises oxidizing a compound with an aqueous nitric acid solution having a specific gravity of from 1.32 to 1.47 at 20.degree. C., said compound being represented by the following formula (I): ##STR2## wherein X, Y, m and n have the same meanings as defined above and Z is Cl or H.Type: GrantFiled: July 13, 1989Date of Patent: October 2, 1990Assignee: Kureha Kagaku Kogyo K.K.Inventors: Takashi Terauchi, Kazuo Yoshida, Yoshihisa Machida, Nobuyuki Okubo, Yutaka Konai
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Patent number: 4924014Abstract: A process for the preparation of halogen-containing aromatic compounds of the formula I ##STR1## wherein Hal represents halogen,R represents H, C.sub.1 -C.sub.3 -alkyl, phenyl, halogen or trifluoromethyl,Y represents CO or SO.sub.2 andZ represents an aromatic or heteroaromatic group, andY-Z-Y together may also be CO or SO.sub.2, which comprises reacting a haloaromatic compound of the formula RC.sub.6 H.sub.4 Hal (II) with a halide of a bisacid having the formula Hal-Y-Z-Y-Hal (III) in a molar ratio of at least 2:1 in the presence of hydrogen fluoride and or boron trifluoride, in formulae II and III Hal, R, Y and Z having the aforementioned meaning.Type: GrantFiled: February 28, 1989Date of Patent: May 8, 1990Assignee: Hoechst AktiengesellschaftInventors: Andreas Fuss, Gunter Siegemund
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Patent number: 4922026Abstract: Aromatic diketones are prepared by a process comprising contacting at least one acylatable aromatic compound and at least one aromatic diacyl halide in the presence of catalytic amounts of ferric chloride or ferric oxide at an elevated temperature and at superatmospheric conditions.Type: GrantFiled: December 27, 1988Date of Patent: May 1, 1990Assignee: The Dow Chemical CompanyInventors: Robert B. Baker, Jr., R. Garth Pews, Eric W. Otterbacher, James A. Gall
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Patent number: 4898983Abstract: Friedel Crafts preparation of aryl carbonyl compounds having an exceptionally high degree of isomeric purity and freedom from by-products can be achieved by adding to the Lewis acid reaction system a protic controlling agent selected from ROX, water, RCOOX, RSO.sub.3 X, and ROY, wherein R is organic, X is hydrogen or metal, and Y is metal. Contrary to conventional expectation, the protic agent does not significantly alkylate or acylate the Friedel Crafts reaction product.Type: GrantFiled: November 7, 1988Date of Patent: February 6, 1990Assignee: Raychem LimitedInventor: Ian D. H. Towle
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Patent number: 4895984Abstract: Aromatics are acylated by the Friedel-Crafts method by carrying out the acylation in the presence of metalalkyls or metalalkyl halides of metals or semimetals of main groups two to five and/or of metals of subgroups two or four of the Periodic Table.Type: GrantFiled: May 25, 1988Date of Patent: January 23, 1990Assignee: BASF AktiengesellschaftInventors: Manfred Eggersdorfer, Hardo Siegel, Alfred Schuhmacher, Walter Grosch, Jochem Henkelmann
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Patent number: 4868338Abstract: The acylation of a naphthalene compound, substituted in the 2-position with an electron-donating group, with a reactive derivative of a lower aliphatic acid, in an aprotic organic diluent and in the presence of a Friedel Crafts catalyst consisting of a halide of an element having at least two valences, is improved when maintaining constant at any time the molar ratio of the naphthalene compound to the acylating agent and that of the acylating agent to the Friedel Crafts catalyst within specific ranges.Type: GrantFiled: March 8, 1988Date of Patent: September 19, 1989Assignee: Blaschim S.p.A.Inventors: Ambrogio Magni, Giuseppina Visentin
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Patent number: 4845302Abstract: 5H-Dibenzo[a,d]cyclohepten-5-ones (I) ##STR1## (A and B being radicals for completing aromatic ring systems) are prepared by converting (Z)-2-(2-arylethenyl)arylcarboxylic acids (II) ##STR2## or E/Z-isomer mixtures thereof with a halogenating agent for carboxylic acids at from (-30.degree.) to +120.degree. C. to the corresponding carbonyl halides (III) ##STR3## where X is halogen, and cyclizing said carbonyl halides at from 0.degree. to 100.degree. C. in the presence of a Lewis acid.Type: GrantFiled: December 18, 1987Date of Patent: July 4, 1989Assignee: BASF AktiengsellschaftInventors: Marco Thyes, Gerd Steiner
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Patent number: 4835318Abstract: A process for the preparation of arylperfluoroalkyl ketones of the general formula I ##STR1## wherein R.sup.1 and R.sup.5 represent at least one of the substituents hydrogen, halogen, alkyl, alkoxy, alkylthio and perfluorinated alkyl, each having from 1 to 6 carbon atoms and n is an integer from 1 to 6, which comprises reacting an aryl carbonyl compound having the general formula II ##STR2## wherein R.sup.1 to R.sup.5 have the above-mentioned meaning and X as a monovalent moiety represents fluorine, chlorine or bromine and as a bivalent moiety the oxygen atom of an anhydride bridge, with a perfluoroalkyl halide of the general formula C.sub.n F.sub.2n+1 -Hal (III), wherein Hal represents chlorine, bromine or iodine and n is an integer from 1 to 6, in the presence of a trisdialkyl amide of phosphorus acid of the general formula P[N(alkyl)2]3 (IV).Type: GrantFiled: July 28, 1988Date of Patent: May 30, 1989Assignee: Hoechst AktiengesellschaftInventors: Alfred Kruse, Gunter Siegemund, Klaus Schlich, Ingo Ruppert, deceased
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Patent number: 4827044Abstract: Process of preparation of ketones by the reaction of an organo-metallic compound with a compound carrying a carbonyl, within a solvent, in the presence of a manganous salt as catalyst. The manganous salt is in the form of a double salt of Mn and an alkali metal cation.Type: GrantFiled: March 8, 1988Date of Patent: May 2, 1989Assignee: Societe Nationale Elf AquitaineInventors: Pierre Tozzolino, Gerard Cahiez
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Patent number: 4814508Abstract: Aromatic carbonyl compounds, in particular arylene ether ketones, are prepared by reacting an appropriate reagent system in the presence of free Lewis acid and a complex between a Lewis acid, for example, aluminum trichloride, and a Lewis base, for example, N,N-dimethylformamide, and, optionally, a diluent, such as methylene chloride. The process is particularly advantageous for the preparation of substantially or all para-linked arylene ether ketones as the presence of the Lewis acid/Lewis base complex markedly reduces alkylation and ensures the substantial absence of ortho substitution.Type: GrantFiled: March 21, 1988Date of Patent: March 21, 1989Assignee: Raychem CorporationInventors: Heinrich C. Gors, Patrick J. Horner, Viktors Jansons
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Patent number: 4803013Abstract: Novel halogenated naphthalene derivatives of the formula ##STR1## where X is F or Br, and a process for making the same are disclosed. Insulating oils are also disclosed which essentially comprise such a fluorine-containing compound and commonly used hydrocarbon insulating oils. The additive is highly conductive to improved dielectric constant, dielectric loss, hydrogen gas absorptivity, fluidity and viscosity characteristics.Type: GrantFiled: March 16, 1988Date of Patent: February 7, 1989Assignee: Nippon Oil Co., Ltd.Inventor: Nobuo Yokoyama
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Patent number: 4749804Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: June 10, 1986Date of Patent: June 7, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: George C. Schloemer
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Patent number: 4681952Abstract: A process for the preparation of 2,2-dimethyl-3-arylcyclopropanecarboxylic acid or ester of the formula ##STR1## in which Ar is naphthyl or the radical ##STR2## R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, Z is oxygen, sulphur, or 1,2-ethenediyl, andR.sup.2 represents hydrogen, halogen, cyano, nitro or trialkylsilyl or a radical, which is optionally substituted by halogen, from the series comprising alkyl, cycloalkyl, alkenyl, alkoxy, alkylenedioxy, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylamino, phenyl and phenoxy,comprising reacting a 1-aryl-1-halogeno-2,2-dimethyl-3-butanone of the formula ##STR3## in which X.sup.1 is chlorine or bromine, with a base in the presence of a diluent at a temperature between about -20.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-arylcyclobutanone of the formula ##STR4## and reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +50.degree. C.Type: GrantFiled: November 7, 1984Date of Patent: July 21, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4665246Abstract: The process of producing ethynyl aromatic compounds which are useful as intermediates in the preparation of 3-dimensional carbon-carbon structures for aerospace and military applications and as starting materials in the preparation of organic semi-conductors. The ethynyl aromatic compounds may be any of the classes illustrated in FIGS. 1, 2 and 3 of the drawing. Starting compounds for the process may by any compound from the classes illustrated in FIGS. 4, 5 and 6. The starting compound is reacted in the presence of a Friedel-Crafts catalyst in a suitable solvent with an acyl compound from the class illustrated in FIG. 7 to yield a compound within the classes illustrated in FIGS. 8, 9 and 10. The carbonyl groups in this compound are reduced to yield a corresponding alcohol. Each hydroxy group in the alcohol is converted to an easily eliminatable group, e.g., by reacting it with methane sulfonyl chloride, when subjected to basic conditions.Type: GrantFiled: March 9, 1984Date of Patent: May 12, 1987Assignee: Chem Biochem Research, Inc.Inventor: Chris Anderson
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Patent number: 4618726Abstract: A process for the preparation of benzophenones. A compound of the formula COX.sub.4 X.sub.5, where X.sub.4 and X.sub.5, which may be identical or different are halogen atoms, is reacted, in liquid hydrofluoric acid, with a deactivated benzene derivative, in the presence of boron trifluoride in such amount that the absolute pressure of boron trifluoride in the reaction space is at least one bar.Type: GrantFiled: December 18, 1984Date of Patent: October 21, 1986Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4611080Abstract: A process for the preparation of a halogenated aroylacetic acid ester of the formula ##STR1## in which R is alkyl with 1-6 carbon atoms,X and X.sup.2 each independently is halogen, andX.sup.1 and X.sup.3 each independently is hydrogen or halogen, comprising reacting a benzoyl chloride of the formula ##STR2## with dichloroethylene in the presence of anhydrous aluminum chloride to form the corresponding benzene trichloroethyl ketone, dehydrochlorinating the trichloroethyl ketone to form the corresponding benzene dichlorovinyl ketone, and treating the dichlorovinyl ketone with an alcoholate and then with an aqueous acid. The products are known intermediates for known antibacterials.Type: GrantFiled: July 12, 1985Date of Patent: September 9, 1986Assignee: Bayer AktiengesellschaftInventor: Klaus Grohe
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Patent number: 4605758Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 4593125Abstract: Naphthalene substituted in the 2- or .beta.-position with an electron-donating substituent can be acylated with high regioselectivity in the 6-position by using an acylating agent in substantially anhydrous hydrogen fluoride which functions both as catalyst and solvent.Type: GrantFiled: March 13, 1985Date of Patent: June 3, 1986Assignee: Celanese CorporationInventors: Kenneth G. Davenport, H. Clay Linstid, III
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Patent number: 4562287Abstract: Therapeutic compositions having anti-inflammatory and analgesic activity, containing as active compound 2-(4-biphenylyl)-4-hexenoic acid and/or derivatives thereof, characterized by low toxicity and by the absence or minimum level of ulcerogenic effect.Type: GrantFiled: May 29, 1984Date of Patent: December 31, 1985Assignee: Scharper S.p.A. per l'Industria FarmaceuticaInventors: Alfonso Del Vecchio, Grazia Sestini
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Patent number: 4552876Abstract: Compounds of the formula: ##STR1## wherein, R is H, alkyl, cycloalkyl, aryl, or heteroaryl;R.sub.1 is H, alkyl, cycloalkyl, aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aryl, halo, OR.sup.2, SR.sup.2, NR.sub.2, CF.sub.3, NO.sub.2, CN, COOR.sup.2, CHO, SO.sub.3 H or SO.sub.2 NH.sub.2,whereinR.sup.2 is H, methyl, ethyl or propyl;Y is ##STR2## Z is O, S, NH or CH.sub.2 ; X is --CH.sub.2 --, ##STR3## or --(CH.sub.2).sub.n CHOH(CH.sub.2).sub.n --; whereinR.sup.2 is H, methyl, ethyl or propyl;n is 1-10, and pharmaceutically acceptable salts thereof have antiallergy and antiinflammatory activity.Type: GrantFiled: July 9, 1984Date of Patent: November 12, 1985Assignee: USV Pharmaceutical Corp.Inventors: Howard Jones, Ernest Magnien, John H. Musser, Mujahid L. Shaikh
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Patent number: 4546184Abstract: The invention relates to a novel fluorinated pre-polymer and novel process steps in producing the same. The pre-polymers are quinoxaline materials derived by reaction of diketone linkage containing perfluoro-compounds with an aromatic diamine. The diketone is produced by oxidatively dechlorinating a polychloroketone which may be a monoketone or a bis-ketone. The polychloroketone is produced by reacting a keto-ylid with a chlorinating agent, e.g., chlorine. The keto-ylid is produced by reacting a phosphorane with an acid halide of a polyoxy-perfluoroalkylene oxide wherein the perfluoro-oxyalkylene group contains two or three carbon atoms, and there are present from two to twenty perfluoro-oxyalkylene units in the oligomer. The quinoxalines, the polychloroketones and the diketones hereof are novel products. Cross-linking may be effected with a free radical generator.Type: GrantFiled: May 23, 1983Date of Patent: October 8, 1985Assignee: SCM CorporationInventor: Keith B. Baucom
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Patent number: 4539420Abstract: A manufacturing method is described for the preparation of optically active 1-aromatic-group-substituted-1-alkanones characterized in that an optically active alkane acid halide is allowed to react with an aromatic compound in the presence of a Lewis acid. The optically active 1-aromatic-group-substituted-1-alkanones are useful intermediates in the preparation of optically active alpha-arylalkanoic acids, which are useful as pharmaceutical, e.g. anti-inflammatory, analgesic and anti-pyretic, agents and as insecticidal agents.Type: GrantFiled: June 11, 1982Date of Patent: September 3, 1985Assignee: Syntex Pharmaceuticals International LimitedInventors: Gen-Ichi Tsuchihashi, Shuichi Mitamura, Koji Kitajima
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Patent number: 4529813Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.Type: GrantFiled: March 14, 1980Date of Patent: July 16, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann