Halogen Containing Patents (Class 568/709)
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Patent number: 8859819Abstract: The present invention relates to a compound of the general formula (I) where: X?S, SO or SO2; and one of the radicals R1 and R2 is a hydrogen atom and the other is a radical: a C1 to C18 linear or branched alkyl, optionally substituted by one or more halogen atom(s); a C2 to C18 linear or branched alkenyl, optionally substituted by one or more halogen atom(s); an aralkyl, optionally substituted by one or more C1 to C6 alkoxy group(s); or a COR3 or CONHR3, but not simultaneously, where R3 is a radical: a C1 to C18 linear or branched alkyl, optionally substituted by one or more halogen atom(s); a C2 to C18 linear or branched alkenyl, optionally substituted by one or more halogen atom(s); an aralkyl, optionally substituted by one or more C1 to C6 alkoxy group(s); an aralkenyl, optionally substituted by one or more C1 to C6 alkoxy groups and/or one or more OH group(s); or an aryl radical, optionally substituted by one or more C1 to C6 alkoxy group(s).Type: GrantFiled: April 8, 2010Date of Patent: October 14, 2014Assignee: Pierre Fabre Dermo-CosmetiqueInventor: Stéphane Poigny
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Publication number: 20120178931Abstract: Provided is a process by which pyrimidinylacetonitrile derivatives can be prepared easily and efficiently from industrially available raw materials. Also provided are intermediates for the synthesis of the derivatives. A process for the preparation of pyrimidinylacetonitrile derivatives represented by general formula (3) [wherein X is a halogen atom, and R is an alkoxymethyl group], characterized by reacting a 2,4-dihalogeno-6-nitrobenzene derivative represented by general formula (1) [wherein X and R are each as defined above] with 4,6-dimethoxy-2-cyanomethylpyrimidine represented by general formula (2) [wherein Me represents a methyl group] in the presence of a base; and intermediates for the synthesis of the pyrimidinylacetonitrile derivatives.Type: ApplicationFiled: August 23, 2010Publication date: July 12, 2012Applicant: IHARA CHEMICAL INDUSTRY CO., LTDInventor: Kentaro Kawazoe
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Patent number: 6977315Abstract: The present invention relates to a process for producing optically active ?-nitroalcohols wherein nitroaldol reactions of aldehydes and nitroalkanes are carried out in the presence of a base and an optically active metal complex catalyst represented by the following formula (c): (where R4, R5, and R6 represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an acyl group, an alkoxycarbonyl group, or an aryloxycarbonyl group, and R5 and R6 may be linked together to form a ring; X* represents a hydrocarbon group having an asymmetric carbon atom or axial asymmetry; M represents a cobalt ion or a chromium ion; and Y represents an anion capable of forming a salt when the valence of M is larger than that of a ligand).Type: GrantFiled: November 2, 2004Date of Patent: December 20, 2005Assignee: Mitsui Chemicals, Inc.Inventors: Tohru Yamada, Taketo Ikeno
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Patent number: 6358431Abstract: A method of imparting a water repellent surface to a hydrophilic substrate which comprises contacting the substrate with a solution or dispersion of a suitable calixarene in a liquid medium.Type: GrantFiled: February 24, 1999Date of Patent: March 19, 2002Assignee: The University of SheffieldInventors: Charles James Matthew Stirling, Frank Davis
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Patent number: 6265621Abstract: The present invention provides a process for producing a halogenated phenol compound represented by the general formula [II]: wherein Q is a monovalent organic residue, A is, the same or different, a hydrogen atom, halogen atom, —SO3H or —SO3Na group, or A at the ortho-position relative to Q may be combined with Q to form a divalent organic residue and X is a halogen atom including each isotope thereof, which comprises the step of reacting in a solvent a phenol compound represented by the general formula [I]: wherein X, Q and A have the same meanings as defined above, with a halide ion represented by the general formula X− wherein X has the same meanings as defined above, in the presence of a semiconductor catalyst with a photocatalytic activity under light irradiation conditions. According to the present invention, the halogenated phenol compound can be produced under moderate conditions.Type: GrantFiled: August 15, 2000Date of Patent: July 24, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Komori, Kazuhiko Nishioka
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Patent number: 5847231Abstract: Process for preparing 4-nitrophenol derivatives of formula (IV) with high selectivity, which comprises converting phenols to diphenyl oxalate derivatives of formula (III) and conducting nitration reaction and hydrolysis to give said 4-nitrophenol derivatives. ##STR1## In the above formulae, R is, the same or different from each other, an alkyl group having 1 to 4 carbon atoms; a halogen atom; an alkoxy group having 1 to 4 carbon atoms; a formyl group; a nitrile group; --COOR.sup.1 (R.sup.1 is an alkyl group having 1 to 4 carbon atoms); --CONR.sup.2 R.sup.3 (R.sup.2 and R.sup.3 are, the same or different from each other, hydrogen atom(s) or alkyl group(s) having 1 to 4 carbon atoms); or --COR.sup.4 (R.sup.4 is an alkyl group having 1 to 4 carbon atoms), andR is not substituted at the 4-position of the phenyl ring and not substituted at the 2- and 6-positions of the phenyl ring at the same time, and,n is 1, 2 or 3.Type: GrantFiled: April 9, 1997Date of Patent: December 8, 1998Assignee: Junsei Chemical Co., Ltd.Inventors: Hideki Kanno, Hiroyuki Chida, Yurie Otani
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Patent number: 5817888Abstract: A bromination process for organic compounds employs stabilized bromine chloride solutions as the brominating agent. Activated aromatic compounds such as anisole can be selectively monobrominated in the para-position in high purity and yield.Type: GrantFiled: June 9, 1997Date of Patent: October 6, 1998Assignee: Albemarle CorporationInventors: Hassan Y. Elnagar, Robert L. Davis, Mahmood Sabahi
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Patent number: 5773651Abstract: Process for the preparation of fluorine-containing compounds by reduction in a container provided with a stirrer, the stirrer being constructed entirely or partly of a carbon material.Type: GrantFiled: November 27, 1996Date of Patent: June 30, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Friedrich Seitz
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Patent number: 5414148Abstract: p-Nitrophenolic compounds, e.g., p-nitrophenol itself, are selectively prepared by (a) reacting a phenolic compound with a nitrosating agent in the presence of sulfuric acid, the concentration of which H.sub.2 SO.sub.4 being at least 60%, (b) oxidizing the p-nitrosophenolic compound thus formed with nitric acid, the concentration of sulfuric acid in the medium of reaction, upon completion of oxidation, being no greater than 80%, and (c) separating the p-nitrophenolic compound which thus precipitates.Type: GrantFiled: May 26, 1994Date of Patent: May 9, 1995Assignee: Rhone-Poulenc ChimieInventors: Pascal Metivier, Laurent Bernard
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5371291Abstract: The invention is a new process for preparing 4,6-diaminoresorcinol, a precursor to polybisbenzoxazoles. The desired product is prepared from resorcinol by incorporating a halo group on the 2-position of resorcinol to form 2-haloresorcinol, then nitrating selectively at the 4- and 6-positions of the 2-haloresorcinol to form 2-halo-4,6-dinitroresorcinol, then hydrogenating the 2-halo-4,6-dinitroresorcinol. The selective incorporation of a halo group on the 2-position of resorcinol is accomplished by sulfonating resorcinol at the 4- and 6-positions.Type: GrantFiled: October 15, 1993Date of Patent: December 6, 1994Assignee: The Dow Chemical CompanyInventor: Bassam S. Nader
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Patent number: 5292932Abstract: Process for the preparation of compounds of the formula (1) ##STR1## in which R is an alkyl (C.sub.1 -C.sub.6) group and X is a hydrogen or alkali metal atom, in which compounds of the formula (2) ##STR2## in which R and X have the abovementioned meanings, are converted into the corresponding diazonium compound with a diazotizing agent in a mineral acid at temperatures of about -5.degree. C. to about +25.degree. C., this diazonium compound is then reacted, without or after intermediate isolation, with aqueous mineral acid at temperatures of about 70.degree. C. to about 120.degree. C. and the resulting compounds of the above formula (1) are isolated.Type: GrantFiled: April 10, 1992Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Tronich, Carl-Stephan Frohlich, Gunther Sell
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Patent number: 5292966Abstract: 2-Nitro-3,6-dichlorophenol is prepared by sulfonation of 2,5-dichlorophenol and subsequent nitration and desulfonation, in which the nitration is carried out by metering in a nitrating acid composed of 98 to 100% strength nitric acid and 96 to 100% strength sulfuric acid at temperatures from -15.degree. to 35.degree. C. and a metering time of at least 1 hour.Type: GrantFiled: March 16, 1993Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Michael Meier, Heinz-Georg Kautz
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Patent number: 5292967Abstract: According to a process for producing isomer-free 2,3-difluoro-6-nitrophenol, 2,3,4-trifluoronitrobenzene is reacted with an aqueous solution of alkali metal or alkaline earth metal hydroxide in the absence of organic solvent, at temperatures between about 20.degree. C. and 100.degree. C., the pH value of the reaction mixture is set at about 1 to 6 by acid addition, the resulting product is stream distilled and the 2,3-difluoro-6-nitrophenol is isolated after cooling. No organic solvents are used during any of the steps of the process.Type: GrantFiled: March 23, 1993Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Joachim Hackenbruch, Ralf Pfirmann
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Patent number: 5227535Abstract: The present invention relates to a process for the preparation of isomerically pure 2-nitro-5-fluoro- or -5-chlorophenol, by reacting 2,4-difluoronitrobenzene or 2,4-dichloronitrobenzene with aqueous alkali metal or alkaline earth metal hydroxide solution or suspension in the absence of organic solvents or other solubility promoting substances at temperatures from about 20.degree. C. to about 190.degree. C., adjusting the pH of the reaction mixture to about 1 to about 6 by the addition of acid, steam distilling the resultant product and isolating it from the distillate after cooling.Type: GrantFiled: October 7, 1992Date of Patent: July 13, 1993Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs, Klaus Forstinger
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Patent number: 5204242Abstract: The present invention provides a colorimetric process for the detection of an oxidative coupling reaction in which a coupling component is reacted with a developer component in the presence of an oxidation agent to give a colored material, wherein, as coupling component, there is used a compound of the general formula: ##STR1## in which X is a bromine or chlorine atom, n is 1, 2 or 3, Y is COOR, CONRR', SO.sub.3 R, SO.sub.2 NRR', OR, NRR' or NRR'R".sym. and R, R' and R", independently of one another, are hydrogen atoms or C.sub.1 -C.sub.3 -alkyl radicals.The present invention also provides a reagent which contains the above compound, as well as new substituted phenols and a process for the preparation thereof.Type: GrantFiled: September 17, 1991Date of Patent: April 20, 1993Assignee: Boehringer Mannheim GmbHInventors: Martina Junius-Comer, Bernd Vogt, Rupert Herrmann
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Patent number: 5136109Abstract: 2-4-Dichloro-3-alkyl-6-nitrophenols which are useful as intermediate of cyan couplers in color photography are prepared by sulfonating 4-chloro-3-alkyl-phenols to obtain 5-chloro-4-alkylhydroxybenzenesulfonic acids, chlorinating the acids in an aqueous phase to obtain 3,5-dichloro-4-alkyl-2-hydroxybenzenesulfonic acids and nitrating the sulfonic acids.Type: GrantFiled: May 29, 1991Date of Patent: August 4, 1992Assignee: Taoka Chemical Company, Ltd.Inventors: Osamu Kimura, Yasuhiko Horikawa, Masaya Yamashita, Kazutaka Morino, Shinichi Koyama
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Patent number: 5012015Abstract: 2,4-Dichloro-3-alkyl-6-nitrophenol, which is a precursor of 2,4-dichloro-3-alkyl-6-aminophenol useful for the production of a cyan coupler to be used with a sensitive material in the field of a photography in color, is industrially advantageously produced by (a) nitration of 2,4,5-trichloro-3-alkylbenzene, followed by hydrolysis of the resulting 2,4,5-trichloro-3-alkyl-6-nitrobenzene, or (b) hydrolysis of 2,4,5-trichloro-3-alkylbenzene-6-sulfonic acid or a salt thereof, followed by nitration of the resulting 2,4-dichloro-3-alkylphenol-6-sulfonic acid or a salt thereof, the starting material usable for these processes being 4-alkylbenzenesulfonic acid or a salt thereof, which is easily available.Type: GrantFiled: March 7, 1989Date of Patent: April 30, 1991Assignees: Daiei Chemical Co., Ltd., Sumitomo Chemical Co., Ltd.Inventors: Masanobu Terao, Yuzo Maegawa, Yasuyoshi Ueda, Kiyoyasu Hashimoto, Takashi Omura
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Patent number: 5001279Abstract: The displacement of halogen from a 1,2,3-trihalo-4,6-dinitroresorcinol can be carried out in an aqueous medium using alkali metal hydroxide to form 2-halo-4,6,-dinitroresorcinol. The product is a useful intermediate in the synthesis of 4,6-diaminoresorcinol, which is a monomer for polybenzoxazole polymers. The process from part of a useful aqueous process for synthesizing 4,6-diaminoresorcinol.Type: GrantFiled: November 17, 1989Date of Patent: March 19, 1991Assignee: The Dow Chemical CompanyInventor: Tyze-Kuan T. Yin
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Patent number: 4978808Abstract: Disclosed herein is a method of producing 2,2-bis(3-nitro-4-hydroxphenyl)hexafluoropropane, which comprises (a) preparing 2,2-bis(4-hydroxyphenyl)hexafluoropropane and a lower fatty acid; and (b) allowing the 2,2-bis(4-hydroxyphenyl)hexafluoropropane to react with nitric acid in the lower fatty acid.Type: GrantFiled: May 31, 1989Date of Patent: December 18, 1990Assignee: Central Glass Company, LimitedInventors: Masamichi Maruta, Tetsuo Wada
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Patent number: 4962198Abstract: The invention relates to a generally applicable process for the hydroxylation of electrophilic aromatic compounds, according to which the electrophilic aromatic compounds are reacted with organic hydroperoxides in the presence of bases.Type: GrantFiled: July 7, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Mieczyslaw Makosza, Krzysztof Sienkiewicz
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Patent number: 4960955Abstract: The process of making 4-chloro-2-methyl-5-nitro phenol (I) ##STR1## comprises nitrating a 4-chloro-2-methyl-phenyl sulfonate of the formula (II) at the 5 position ##STR2## in which R is a residue selected from the group consisting of methyl-, ethyl-, trifluoromethyl-, phenyl- and tolyl and the sulfonyl residue comprises --SO.sub.2 R at the position 5 to form 4-chloro-2-methyl-5-nitro-phenyl-sulfonate and then cleaving the sulfonyl residue of the 4-chloro-2-methyl-5-nitro-phenyl-sulfonate to form the 4-chloro-2-methyl-5-nitro-phenyl. The process uses technically available and economical starting materials and allows an isomerically pure product to be made in very good yield.Type: GrantFiled: May 17, 1989Date of Patent: October 2, 1990Assignee: Wella AktiengesellschaftInventors: Thomas Clausen, David Rose
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Patent number: 4954662Abstract: Ortho-substituted phenolic compounds, e.g., 2,6-dichlorophenol, are selectively chlorinated, e.g., into 2,4,6-trichlorophenol, with gaseous chlorine in either the molten state or in a solvent medium, in the presence of a selectivity-enhancing effective amount of an organic cation.Type: GrantFiled: July 18, 1988Date of Patent: September 4, 1990Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Bernard Besson, Isabelle Jouve
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Patent number: 4943666Abstract: An improved industrial process for producing a compound of the general formula: ##STR1## wherein R is an alkyl group having 1 to 4 carbon atoms which comprises reacting a compound of the general formula: ##STR2## wherein R is as defined above with nitrous acid in a mixed solvent of water and a water-insoluble or slightly soluble organic solvent.Type: GrantFiled: April 14, 1989Date of Patent: July 24, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Taiiti Okada, Toru Ishida
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Patent number: 4885388Abstract: New 2-methyl-4-fluoro-phenols and process for their preparation from 2-methyl-4-fluoro-phenol.Type: GrantFiled: September 12, 1988Date of Patent: December 5, 1989Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Reiner Fischer
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Patent number: 4879415Abstract: The invention relates to a process for the preparation of chloronitroanilines or chloronitrophenols, which comprises chlorinating nitroanilines or nitrophenols in hydrochloric acid by adding simultaneously separate streams of nitroanilines or nitrophenols and of a chlorinating agent to said hydrochloric acid. The process affords pure products in good yield. An accumulation of chlorine during the reaction is avoided.Chloronitroanilines and chloronitrophenols are useful intermediates for the snythesis of disperse dyes.Type: GrantFiled: November 25, 1987Date of Patent: November 7, 1989Assignee: Ciba-Geigy CorporationInventors: Bernhard Albrecht, Jurgen Beyrich
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Patent number: 4855292Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.Type: GrantFiled: July 23, 1987Date of Patent: August 8, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
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Patent number: 4835324Abstract: A compound of the formula: ##STR1## wherein R is NH.sub.2 or NO.sub.2, and X is chlorine or bromine, is disclosed. These compounds are useful as intermediates in the production of herbicidal tetrahydrophthalimides of the formula: ##STR2## wherein R' is a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, and X is as defined above.Type: GrantFiled: December 9, 1987Date of Patent: May 30, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
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Patent number: 4827047Abstract: The chloronitrophenols, e.g., 2,6-dichloro-4-nitrophenol (a known agrochemical/pharmaceutical intermediate), are efficiently prepared by chlorinating ortho- or para-nitrophenol with gaseous chlorine, characteristically in the molten state, and in the presence of a catalytically effective amount of a primary, secondary or tertiary amine.Type: GrantFiled: March 7, 1988Date of Patent: May 2, 1989Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Isabelle Jouve
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Patent number: 4766244Abstract: High purity 4,6-dinitro-1,3-benzenediol is prepared by (a) contacting a 1,2,3-trihalobenzene with a nitrating agent and an acid under reaction conditions such that a 1,2,3-trihalo-4,6-dinitrobenzene is produced, (b) contacting the 1,2,3-trihalo-4,6-dinitrobenzene prepared in (a) with an alkanol and a base under reaction conditions such that a 4,6-dinitro-2-halo-1,3-benzenediol is produced, and (c) contacting the 4,6-dinitro-2-halo-1,3-benzenediol prepared in (b) with a hydrogenating agent in the presence of a solvent and a catalyst under reaction conditions such that a 4,6-diamino-1,3-benzenediol is produced. This 4,6-diamino-1,3-benzenediol is useful in the preparation of high molecular weight polybenzoxazoles.Type: GrantFiled: October 30, 1986Date of Patent: August 23, 1988Assignee: The Dow Chemical CompanyInventor: Zenon Lysenko
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Patent number: 4723043Abstract: Substituted phenols are nitrated by contacting same with a 10 to 70% by weight concentrated aqueous solution of nitric acid. The subject nitration process is well adopted for the preparation, e.g., of 2,6-dichloro-4-nitrophenol, a valuable intermediate in the production of various agrochemicals/pharmaceuticals.Type: GrantFiled: July 7, 1986Date of Patent: February 2, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4720595Abstract: Agents which contain a combination product of 30 to 90% by weight of 3-trifluoromethyl-4-nitrophenol, which contains 12 to 20% by weight of water, with 10 to 70% by weight of a basic salt of the alkaline earth series or of the metals Zn(II), Al(III), Fe(II) or Fe(III), where appropriate in the presence of a polyalkylene glycol, are suitable and advantageous for controling lampreys, because they release the active compound in a delayed manner.Type: GrantFiled: October 22, 1986Date of Patent: January 19, 1988Assignee: Hoechst AktiengesellschaftInventors: Gerhard Frisch, Paul Bittner
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Patent number: 4670608Abstract: 2,4-Dichloro-3-alkyl-6-nitrophenols are prepared by chlorinating, with chlorine in the presence of a catalyst, 1-alkyl-4-nitrobenzenes having a C.sub.2 -C.sub.8 -alkyl radical until the content of trichloroalkylnitrobenzenes is at least 60% by weight in the chlorination mixture, removing the catalyst from the chlorination mixture, then hydrolyzing the chlorination mixture, removing the precipitated reaction product, and treating it with an aqueous inorganic acid. The 2,4-dichloro-3-alkyl-6-nitrophenols are new.Type: GrantFiled: March 19, 1986Date of Patent: June 2, 1987Assignee: Bayer AktiengesellschaftInventors: Christian Paetz, Karlfried Wedemeyer
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Patent number: 4596893Abstract: The present invention relates to 2-trifluoro-methyl-4,6-dinitro-phenol and derivatives thereof prepared by hydrolyzing 2-chloro-3,5-dinitrobenzotrifluoride with an alkali hydroxide or alkaline earth metal hydroxide at elevated temperature in an aqueous medium without catalyst, 2-trifluoro-methyl-4,6-dinitro-phenol show herbicidal, acaricidal and crop regulating properties.Type: GrantFiled: May 23, 1985Date of Patent: June 24, 1986Assignee: Budapesti VegyimuvekInventors: Gyula Eifert, Ferenc Bihari, Istvan Magyari, Jeno Meszaros, Peter Inczedy, Judit Timar, Rudolf Czovek, Peter Bohus, Egon Klumpp, Erzsebet Schuszler
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Patent number: 4581178Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.Type: GrantFiled: February 28, 1985Date of Patent: April 8, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Milstein
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Patent number: 4558040Abstract: Certain miticidal (2-alkyl-3,4-dihydro-2H-1-benzopyran-8-yl)diazenecarboxylic acid esters.Type: GrantFiled: December 3, 1984Date of Patent: December 10, 1985Assignee: Shell Oil CompanyInventors: Kurt H. Pilgram, Richard D. Skiles
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Patent number: 4551264Abstract: New polyhalogenoaromatic compounds of Formula I ##STR1## wherein Y and Z are each independently alkyl, alkoxy or alkanoyl each of 1 to 12 C atoms, --COOR.sup.1, --O--CO--R.sup.1, CN, NO.sub.2, NH.sub.2 or OH;Q is one or two identical or different radicals selected from Ph, Cy, 1,4-bicyclo[2,2,2]octylene or 1,3-dioxane-2,5-diyl;X.sup.1 to X.sup.4 are each independently H, F, Cl or Br;R.sup.1 is alkyl of 1 to 4 C atoms, Ph--R.sup.2 or Cy--R.sup.2 ;R.sup.2 is alkyl or alkoxy each of 1-12 C atoms or CN;Ph is 1,4-phenylene; and Cy is 1,4-cyclohexylene,can be used as components of liquid-crystal dielectrics.Type: GrantFiled: March 14, 1983Date of Patent: November 5, 1985Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Michael Romer, Georg Weber
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Patent number: 4540832Abstract: A process for the preparation of 6-chloro-2,4-dinitrophenol in a high yield and in a high degree of purity by saponifying 2,4-dinitrochlorobenzene and/or 2,4-dinitrophenyl alkyl ethers of the formula ##STR1## in which m denotes the number 2, 3 or 4 and n denotes the number 1 or 2, by means of aqueous sodium hydroxide or potassium hydroxide solution and chlorinating the resulting 2,4-dinitrophenol with sodium hypochlorite, which comprises chlorinating the 2,4-dinitrophenol, without prior isolation as an intermediate, in aqueous suspension at a pH value of 3.5-7 by means of chlorine bleach liquor at temperatures of 5.degree. to 20.degree. C.Type: GrantFiled: April 26, 1984Date of Patent: September 10, 1985Assignee: Hoechst AktiengesellschaftInventors: Otto Arndt, Theodor Papenfuhs
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Patent number: 4538004Abstract: 4-(3-Trifluoromethyl-4-nitrophenyl)phenols are prepared by reacting a 2-trifluoromethyl-1-nitrobenzene having a replaceable hydrogen in the 4-position with a phenol having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The 2-trifluoromethyl-1-nitrobenzene and phenol may be substituted or unsubstituted, and preferred phenols include phenol and 2,6-dialkylphenols.Type: GrantFiled: May 4, 1984Date of Patent: August 27, 1985Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4538005Abstract: 4-(2-Trifluoromethyl-4-nitrophenyl)phenols are prepared by reacting a 3-trifluoromethyl-1-nitrobenzene having a replaceable hydrogen in the 4-position with a phenol having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The 3-trifluoromethyl-1-nitrobenzene and phenol may be substituted or unsubstituted, and preferred phenols include phenol and 2,6-dialkylphenols.Type: GrantFiled: May 7, 1984Date of Patent: August 27, 1985Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4479019Abstract: A process is disclosed for separating nitrated phenolic compounds from other nitrated and unnitrated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with one of the phenolics over other related phenolics in the mixture. The preferentially-formed complex of one of the phenolics may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one phenolic. The process is particularly suitable for resolving a mixture comprising phenol or cresol from their ortho-nitrated derivatives, or a mixture of two isomeric nitrated phenols or cresols or a mixture of mono-and dinitrated phenols or cresols.Type: GrantFiled: February 21, 1984Date of Patent: October 23, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4473713Abstract: At least one of the other functions comprising an aryl-aliphatic ether, e.g., veratrol, is catalytically hydrolyzed with water, e.g., to guaiacol, in the presence of a catalytically effective amount of a salt of a carboxylic acid.Type: GrantFiled: September 27, 1982Date of Patent: September 25, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4347148Abstract: Nitro phenols of the general formula ##STR1## wherein R is an aliphatic substituent of at least about 40 carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants and intermediates to such additives. These nitro phenols can be conveniently prepared by nitrating appropriate phenols. Typically nitro phenols are formed by nitration of alkyl phenols having an alkyl group of at least about 50 carbon atoms.Type: GrantFiled: November 19, 1979Date of Patent: August 31, 1982Assignee: The Lubrizol CorporationInventor: Kirk E. Davis
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Patent number: 4310702Abstract: Sulfuryl chloride is reacted in the liquid phase with an organic reactant which is a ketone or aromatic alcohol unsubstituted on both ortho carbons in the presence of a moderator selected from the group consisting of aliphatic alcohols of 1-3 carbons and aliphatic ethers of 2-6 carbons, with sufficient moderator being present to selectively produce a product substantially free of compounds with more than one chlorine atom per carbonyl or aromatic hydroxy. The products, such as monochloroacetone, monochlorocyclohexanone, monochlorophenol and 2,2-bis(3-chloro-4-hydroxyphenyl)propane, are useful as chemical intermediates and as monomers for flame retardant polymers.Type: GrantFiled: July 28, 1980Date of Patent: January 12, 1982Assignee: Allied CorporationInventors: Divakaran Masilamani, Milorad M. Rogic
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Patent number: 4310711Abstract: A process for preparing 5-chloro-2-nitrophenol from 2,4-dichloronitrobenzene and excess alkali metal hydroxide in the presence of aprotic polar solvents at 20.degree. to 150.degree. C.Type: GrantFiled: September 2, 1980Date of Patent: January 12, 1982Assignee: Hoechst AktiengesellschaftInventors: Helmut Muller, Konrad Baessler
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Patent number: 4283565Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.Type: GrantFiled: December 29, 1978Date of Patent: August 11, 1981Assignee: Dynamit Nobel AGInventors: Gunther Bernhardt, Gerhard Daum
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Patent number: 4282160Abstract: The present invention is concerned with novel compounds useful in photographic products and processes comprising triarylmethane dyes possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is an alkyl group or a phenyl group, unsubstituted or substituted with a solubilizing group and Y is an electron-withdrawing group.Type: GrantFiled: May 22, 1980Date of Patent: August 4, 1981Assignee: Polaroid CorporationInventor: James W. Foley
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Patent number: 4224244Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: May 9, 1979Date of Patent: September 23, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
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Patent number: RE34589Abstract: The displacement of halogen from a 1,2,3-trihalo-4,6-dinitroresorcinol can be carried out in an aqueous medium using alkali metal hydroxide to form 2-halo-4,6-dinitroresorcinol. The product is a useful intermediate in the synthesis of 4,6-diaminoresorcinol, which is a monomer for polybenzoxazole polymers. The process from part of a useful aqueous process for synthesizing 4,6-diaminoresorcinol.Type: GrantFiled: October 26, 1992Date of Patent: April 19, 1994Assignee: The Dow Chemical CompanyInventor: Tyze-Kuan T. Yin
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Patent number: RE34745Abstract: High purity 4,6-dinitro-1,3-benzenediol is prepared by (a) contacting a 1,2,3-trihalobenzene with a nitrating agent and an acid under reaction conditions such that a 1,2,3-trihalo-4,6-dinitrobenzene is produced, (b) contacting the 1,2,3-trihalo-4,6-dinitrobenzene prepared in (a) with an alkanol and a base under reaction conditions such that as 4,6-dinitro-2-halo-1,3-benzendiol is produced, and (c) contacting the 4,6-dinitro-2-halo-1,3-benzenediol prepared in (b) with a hydrogenating agent in the presence of a solvent and a catalyst under reaction conditions such that a 4,6-diamino-1,3-benzendiol is produced. This 4,6-diamino-1,3-benzene diol is useful in the preparation of high molecular weight polybenzoxazoles.Type: GrantFiled: November 9, 1992Date of Patent: September 27, 1994Assignee: The Dow Chemical CompanyInventor: Zenon Lysenko