Halogen Containing Patents (Class 568/709)
  • Patent number: 8859819
    Abstract: 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: Grant
    Filed: April 8, 2010
    Date of Patent: October 14, 2014
    Assignee: Pierre Fabre Dermo-Cosmetique
    Inventor: St├ęphane Poigny
  • Publication number: 20120178931
    Abstract: 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: Application
    Filed: August 23, 2010
    Publication date: July 12, 2012
    Applicant: IHARA CHEMICAL INDUSTRY CO., LTD
    Inventor: Kentaro Kawazoe
  • Patent number: 6977315
    Abstract: 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: Grant
    Filed: November 2, 2004
    Date of Patent: December 20, 2005
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tohru Yamada, Taketo Ikeno
  • Patent number: 6358431
    Abstract: 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: Grant
    Filed: February 24, 1999
    Date of Patent: March 19, 2002
    Assignee: The University of Sheffield
    Inventors: Charles James Matthew Stirling, Frank Davis
  • Patent number: 6265621
    Abstract: 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: Grant
    Filed: August 15, 2000
    Date of Patent: July 24, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Komori, Kazuhiko Nishioka
  • Patent number: 5847231
    Abstract: 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: Grant
    Filed: April 9, 1997
    Date of Patent: December 8, 1998
    Assignee: Junsei Chemical Co., Ltd.
    Inventors: Hideki Kanno, Hiroyuki Chida, Yurie Otani
  • Patent number: 5817888
    Abstract: 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: Grant
    Filed: June 9, 1997
    Date of Patent: October 6, 1998
    Assignee: Albemarle Corporation
    Inventors: Hassan Y. Elnagar, Robert L. Davis, Mahmood Sabahi
  • Patent number: 5773651
    Abstract: 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: Grant
    Filed: November 27, 1996
    Date of Patent: June 30, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Friedrich Seitz
  • Patent number: 5414148
    Abstract: 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: Grant
    Filed: May 26, 1994
    Date of Patent: May 9, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Pascal Metivier, Laurent Bernard
  • Patent number: 5393776
    Abstract: 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: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5371291
    Abstract: 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: Grant
    Filed: October 15, 1993
    Date of Patent: December 6, 1994
    Assignee: The Dow Chemical Company
    Inventor: Bassam S. Nader
  • Patent number: 5292966
    Abstract: 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: Grant
    Filed: March 16, 1993
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Meier, Heinz-Georg Kautz
  • Patent number: 5292967
    Abstract: 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: Grant
    Filed: March 23, 1993
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Theodor Papenfuhs, Joachim Hackenbruch, Ralf Pfirmann
  • Patent number: 5292932
    Abstract: 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: Grant
    Filed: April 10, 1992
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Tronich, Carl-Stephan Frohlich, Gunther Sell
  • Patent number: 5227535
    Abstract: 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: Grant
    Filed: October 7, 1992
    Date of Patent: July 13, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs, Klaus Forstinger
  • Patent number: 5204242
    Abstract: 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: Grant
    Filed: September 17, 1991
    Date of Patent: April 20, 1993
    Assignee: Boehringer Mannheim GmbH
    Inventors: Martina Junius-Comer, Bernd Vogt, Rupert Herrmann
  • Patent number: 5136109
    Abstract: 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: Grant
    Filed: May 29, 1991
    Date of Patent: August 4, 1992
    Assignee: Taoka Chemical Company, Ltd.
    Inventors: Osamu Kimura, Yasuhiko Horikawa, Masaya Yamashita, Kazutaka Morino, Shinichi Koyama
  • Patent number: 5012015
    Abstract: 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: Grant
    Filed: March 7, 1989
    Date of Patent: April 30, 1991
    Assignees: Daiei Chemical Co., Ltd., Sumitomo Chemical Co., Ltd.
    Inventors: Masanobu Terao, Yuzo Maegawa, Yasuyoshi Ueda, Kiyoyasu Hashimoto, Takashi Omura
  • Patent number: 5001279
    Abstract: 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: Grant
    Filed: November 17, 1989
    Date of Patent: March 19, 1991
    Assignee: The Dow Chemical Company
    Inventor: Tyze-Kuan T. Yin
  • Patent number: 4978808
    Abstract: 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: Grant
    Filed: May 31, 1989
    Date of Patent: December 18, 1990
    Assignee: Central Glass Company, Limited
    Inventors: Masamichi Maruta, Tetsuo Wada
  • Patent number: 4962198
    Abstract: 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: Grant
    Filed: July 7, 1989
    Date of Patent: October 9, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mieczyslaw Makosza, Krzysztof Sienkiewicz
  • Patent number: 4960955
    Abstract: 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: Grant
    Filed: May 17, 1989
    Date of Patent: October 2, 1990
    Assignee: Wella Aktiengesellschaft
    Inventors: Thomas Clausen, David Rose
  • Patent number: 4954662
    Abstract: 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: Grant
    Filed: July 18, 1988
    Date of Patent: September 4, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Bernard Besson, Isabelle Jouve
  • Patent number: 4943666
    Abstract: 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: Grant
    Filed: April 14, 1989
    Date of Patent: July 24, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Taiiti Okada, Toru Ishida
  • Patent number: 4885388
    Abstract: New 2-methyl-4-fluoro-phenols and process for their preparation from 2-methyl-4-fluoro-phenol.
    Type: Grant
    Filed: September 12, 1988
    Date of Patent: December 5, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Reiner Fischer
  • Patent number: 4879415
    Abstract: 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: Grant
    Filed: November 25, 1987
    Date of Patent: November 7, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Bernhard Albrecht, Jurgen Beyrich
  • Patent number: 4855292
    Abstract: 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: Grant
    Filed: July 23, 1987
    Date of Patent: August 8, 1989
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
  • Patent number: 4835324
    Abstract: 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: Grant
    Filed: December 9, 1987
    Date of Patent: May 30, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
  • Patent number: 4827047
    Abstract: 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: Grant
    Filed: March 7, 1988
    Date of Patent: May 2, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Isabelle Jouve
  • Patent number: 4766244
    Abstract: 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: Grant
    Filed: October 30, 1986
    Date of Patent: August 23, 1988
    Assignee: The Dow Chemical Company
    Inventor: Zenon Lysenko
  • Patent number: 4723043
    Abstract: 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: Grant
    Filed: July 7, 1986
    Date of Patent: February 2, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Serge Ratton
  • Patent number: 4720595
    Abstract: 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: Grant
    Filed: October 22, 1986
    Date of Patent: January 19, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Frisch, Paul Bittner
  • Patent number: 4670608
    Abstract: 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: Grant
    Filed: March 19, 1986
    Date of Patent: June 2, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Paetz, Karlfried Wedemeyer
  • Patent number: 4596893
    Abstract: 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: Grant
    Filed: May 23, 1985
    Date of Patent: June 24, 1986
    Assignee: Budapesti Vegyimuvek
    Inventors: Gyula Eifert, Ferenc Bihari, Istvan Magyari, Jeno Meszaros, Peter Inczedy, Judit Timar, Rudolf Czovek, Peter Bohus, Egon Klumpp, Erzsebet Schuszler
  • Patent number: 4581178
    Abstract: 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: Grant
    Filed: February 28, 1985
    Date of Patent: April 8, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David Milstein
  • Patent number: 4558040
    Abstract: Certain miticidal (2-alkyl-3,4-dihydro-2H-1-benzopyran-8-yl)diazenecarboxylic acid esters.
    Type: Grant
    Filed: December 3, 1984
    Date of Patent: December 10, 1985
    Assignee: Shell Oil Company
    Inventors: Kurt H. Pilgram, Richard D. Skiles
  • Patent number: 4551264
    Abstract: 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: Grant
    Filed: March 14, 1983
    Date of Patent: November 5, 1985
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Michael Romer, Georg Weber
  • Patent number: 4540832
    Abstract: 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: Grant
    Filed: April 26, 1984
    Date of Patent: September 10, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Otto Arndt, Theodor Papenfuhs
  • Patent number: 4538004
    Abstract: 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: Grant
    Filed: May 4, 1984
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4538005
    Abstract: 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: Grant
    Filed: May 7, 1984
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4479019
    Abstract: 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: Grant
    Filed: February 21, 1984
    Date of Patent: October 23, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4473713
    Abstract: 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: Grant
    Filed: September 27, 1982
    Date of Patent: September 25, 1984
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Serge Ratton
  • Patent number: 4347148
    Abstract: 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: Grant
    Filed: November 19, 1979
    Date of Patent: August 31, 1982
    Assignee: The Lubrizol Corporation
    Inventor: Kirk E. Davis
  • Patent number: 4310702
    Abstract: 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: Grant
    Filed: July 28, 1980
    Date of Patent: January 12, 1982
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic
  • Patent number: 4310711
    Abstract: 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: Grant
    Filed: September 2, 1980
    Date of Patent: January 12, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Muller, Konrad Baessler
  • Patent number: 4283565
    Abstract: 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: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4282160
    Abstract: 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: Grant
    Filed: May 22, 1980
    Date of Patent: August 4, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4224244
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: September 23, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: RE34589
    Abstract: 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: Grant
    Filed: October 26, 1992
    Date of Patent: April 19, 1994
    Assignee: The Dow Chemical Company
    Inventor: Tyze-Kuan T. Yin
  • Patent number: RE34745
    Abstract: 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: Grant
    Filed: November 9, 1992
    Date of Patent: September 27, 1994
    Assignee: The Dow Chemical Company
    Inventor: Zenon Lysenko