Ether Oxygen Bonded Directly To Benzene Ring Patents (Class 568/584)
  • Patent number: 4847426
    Abstract: A process for the preparation of 2,4-dinitrophenyl ethers of the general formula (1) ##STR1## in which R denotes an alkyl(C.sub.1 -C.sub.6) or alkoxy(C.sub.1 -C.sub.4)alky(C.sub.1 -C.sub.4) group by reacting 1 mole of 2,4-dinitrochlorobenzene in the anhydrous alcohol which is required for the ether formation and is of the general formula (2)R--OH (2)in which R has the abovementioned meaning, in the presence of 1.0 to 3.0 mole of an anhydrous alkali metal carbonate, at temperatures of 20.degree. C. to 150.degree. C., where appropriate under pressure.
    Type: Grant
    Filed: May 25, 1988
    Date of Patent: July 11, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dieter Heck, Hartmut Heise, Manfred Hintzmann
  • Patent number: 4782190
    Abstract: 4-Nitrophenetol is prepared by reaction of 4-chloronitrobenzene with ethanol and alkali metal hydroxides in the presence of phase-transfer catalysts by carrying out the reaction at temperatures from 60.degree. to 95.degree. C. and under pressure in the presence of oxygen-containing gases diluted with inert gases, there being at the start of the reaction 0.2 to 1.0 mol of alkali metal hydroxide metered each hour into the reaction mixture for each 1 mol of 4-chloronitrobenzene.
    Type: Grant
    Filed: March 6, 1987
    Date of Patent: November 1, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef Kasbauer, Karlfried Wedemeyer
  • Patent number: 4613682
    Abstract: The vapor phase reaction of phenolic compounds with organic halides to form aromatic ethers is catalyzed by metal oxides. The halide value of the organic halide is retained as hydrogen halide which can be reacted with a halide acceptor such as methanol to form methyl halide and water.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: September 23, 1986
    Assignee: The Dow Chemical Company
    Inventor: Kathryn A. Eickholt
  • Patent number: 4605745
    Abstract: A method is provided for making aromatic ethers by effecting the displacement of reactive radicals on an activated aromatic nucleus such as a phthalimide with a mono or bisalkali metal phenoxide in the presence of an organic solvent and a dialkylamino branched alkyl substituted pyridinium salt as a phase transfer catalyst. Improved yields of bis(aromatic ethers) are achieved without the production of undesirable by-products, such as akylated phenols.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: August 12, 1986
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Daniel A. Singleton
  • Patent number: 4595763
    Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: June 17, 1986
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • 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: 4537999
    Abstract: A process for the production of dinitrophenyl ethers having the general formula [III]: ##STR1## wherein, one of R.sub.1 and R.sub.2 is a nitro radical, and the other is a hydrogen atom or a straight-chain, branched-chain or cyclic, saturated or unsaturated hydrocarbon radical containing from 1 to 10 carbon atoms, and R.sub.3 is a radical selected from the group consisting of (i) a straight-chain, branched-chain or cyclic, saturated or unsaturated hydrocarbon radical containing from 2 to 10 carbon atoms, (ii) a straight-chain hydrocarbon radical having one phenyl group as a substituent and containing from 1 to 5 carbon atoms, (iii) a phenyl radical, and (iv) a phenyl radical with one or more than one substituents selected from the group consisting of a nitro group, a halogen group, a saturated or unsaturated hydrocarbon group containing from 1 to 5 carbon atoms and an alkoxy group containing from 1 to 4 carbon atoms, by reacting a compound represented by the formula [I]: ##STR2## wherein, R.sub.1 and R.sub.
    Type: Grant
    Filed: September 21, 1983
    Date of Patent: August 27, 1985
    Assignees: Chisso Corporation, Kaken Pharmaceutical Co., Ltd.
    Inventors: Tetsuya Ogawa, Shinichi Saitoh, Takeshi Inoi, Masaji Kato, Heitaro Obara
  • Patent number: 4513141
    Abstract: A method is provided for making aromatic ethers by effecting the displacement of reactive radicals on an activated aromatic nucleus such as a phthalimide with a mono or bisalkali metal phenoxide in the presence of an organic solvent and a dialkylamino branched alkyl substituted pyridinium salt as a phase transfer catalyst. Improved yields of bis(aromatic ethers) are achieved without the production of undesirable by-products, such as alkylated phenols.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: April 23, 1985
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Daniel A. Singleton
  • Patent number: 4479015
    Abstract: The present invention relates to a process for the manufacture of ortho - or para-nitrophenetole. According to the invention, the respective nitrochlorobenzene is reacted with ethanol and alkali hydroxide in the presence of a catalyst system which comprises a tetramethylammonium salt of a general formula (CH.sub.3).sub.4 NX, wherein X is Cl.sup.-, Br.sup.-, HSO.sub.4.sup.- or OC.sub.2 H.sub.5, and an aqueous phase. The process has several advantages such as high yields and purity, the products obtained being completely free of side reaction products such as azoxy compounds.
    Type: Grant
    Filed: January 7, 1983
    Date of Patent: October 23, 1984
    Assignee: GADOT, Petrochemical Industries, Ltd.
    Inventors: Yoel Sasson, Shmuel Zbaida
  • Patent number: 4454355
    Abstract: The invention provides a process for the preparation of p-nitrophenetole with high yields and in an especially pure form from p-chloronitrobenzene and ethanol by heating to a temperature of from 60.degree. to 80.degree. C. with addition of alkali metal hydroxide and a phase transfer catalyst.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: June 12, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Schubert, Konrad Baessler
  • Patent number: 4424365
    Abstract: Novel antibacterially active compound, 1,2,8,8a-cyclopropa?c!benzo?1,2-b:-4,3-b'!dipyrrol-4(5H)-one, prepared by a novel chemical process. This compound, as well as antibacterially-active intermediates, can be used to eradicate or control susceptible bacteria, for example B. subtilis, K. pneumonia, S. lutea, S. aureus, and M. avium.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: January 3, 1984
    Assignee: The Upjohn Company
    Inventor: Wendell Wierenga
  • Patent number: 4423229
    Abstract: Novel antibacterially-active compound, 1,2,8,8a-cyclopropa[ c]-benzo[1,2-b:-4,3-b']dipyrol-4(5H)-one, prepared by a novel chemical process. This compound, as well as antibacterially-active intermediates, can be used to eradicate or control susceptible bacteria, for example, B. subtilis, K. pneumonia, S. lutea, S. aureus, and M. avium.
    Type: Grant
    Filed: February 8, 1982
    Date of Patent: December 27, 1983
    Assignee: The Upjohn Company
    Inventor: Wendell Wierenga
  • Patent number: 4415744
    Abstract: Aromatic compounds are nitrated in the vapor phase via a process comprising contacting the aromatic compound with a nitrating agent in the presence of a nitration promotion catalyst which comprises the adduct of:(a) an alumina-silica-metal oxide combination represented by the formula:(Al.sub.2 O.sub.3).sub.a (SiO.sub.2).sub.b (M.sub.2/n O).sub.cwherein M is a metal cation selected from the group consisting of the lanthanides or rare earths, Groups 1b, 2b, 5b, 6b, 7b, and 8 of the Periodic Table of the Elements, and mixtures thereof, and a, b, and c represent weight percent of the Al.sub.2 O.sub.3, SiO.sub.2, and M.sub.2/n O components, respectively, in the alumina-silica-metal oxide combination, with a being 0 to 100, b being 0 to 100, and c being 0 to 50, and n represents an integer from 1 to 7 of the valence of the metal cation, with the proviso that the sum of (a+b) must be greater than 0, and(b) a catalytically effective amount of sulfur trioxide.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: November 15, 1983
    Assignee: Monsanto Company
    Inventors: Ignatius Schumacher, Kang-Bo Wang
  • Patent number: 4376868
    Abstract: Cresylic acid ethoxylation is catalyzed by basic compounds and salts of alkaline earth metals. Ethoxylates from such reactions have narrow ethylene oxide distributions, lower pour points and lower by-products as compared to alkali base catalyzed ethoxylation. Suitable catalysts include strontium-containing and barium-containing materials. The catalyst also includes co-catalyst combinations using these materials with one or more promoters including polyols, amines, amides, carboxylic acids and phenols. The co-catalyst combinations can be preformed prior to introduction into the reaction mixture.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: March 15, 1983
    Assignee: Conoco Inc.
    Inventors: Gerald L. Nield, Kang Yang, Paul H. Washecheck
  • Patent number: 4349487
    Abstract: Phenolic compounds are etherified by contacting at elevated temperature with a mixture of methyl trichloroacetate and either a primary alkyl halide or an aromatic halide containing strongly electron-withdrawing groups in the presence of an initiator.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: September 14, 1982
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4341905
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of an alkali metal halide catalyst.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: July 27, 1982
    Assignee: The Dow Chemical Company
    Inventor: Paul E. Strege
  • Patent number: 4328166
    Abstract: A compound of the formula: ##STR1## which is useful as a herbicide, is effectively produced by reacting a compound of the formula: ##STR2## with dimethyl sulfate in a two phase reaction medium consisting of water and a hydrophobic organic solvent in the presence of a phase transfer catalyst, or produced through a novel intermediate of the formula: ##STR3##
    Type: Grant
    Filed: November 21, 1980
    Date of Patent: May 4, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Fumio Fujita, Hiroshi Kishida, Nobushige Itaya, Ichiki Takemoto
  • Patent number: 4314086
    Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Daniel Michelet
  • Patent number: 4288638
    Abstract: The invention relates to a process for the synthesis of 2,4-dinitro-6-t-butyl-3-methylanisole or musk ambrette.The process according to the invention is characterized in that 6-t-butyl-3-methylanisole is reacted with a nitrating mixture consisting of 30 to 50% of acetic acid, 20 to 30% of acetic anhydride and 25 to 45% by weight of nitric acid, at between 7.degree. and 15.degree. C. The product is recovered in the pure state with a good yield by adding small amounts of water to the crude reaction mixture.Application: Synthesis of a scented product.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: September 8, 1981
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Helene M. Pascal, Jean-Marie L. Emeury
  • Patent number: 4287125
    Abstract: Benzenoid ethers/thioethers are prepared by reacting an activated halobenzene with an anionic reactant, RA.sup.- M.sup.+, in the presence of at least one tertiary amine sequestering agent having formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: September 1, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Gerard Soula
  • 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: 4257943
    Abstract: A compound of the formula ##STR1## in which X represents chlorine or bromine, Y and Z each represent methyl or ethyl, and n stands for the integer 1 or 2, said compound being useful as a navy blue dye for the dyeing or printing synthetic fibrous materials, preferably polyester fibers, in aqueous baths, suitably in the form of dyestuff preparations containing dispersing agents, and also useful for dyeing fibrous materials in organic solvents, such as trichloroethylene or methanol.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: March 24, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Reinhard Hahnle
  • Patent number: 4236029
    Abstract: The invention relates to a process for the synthesis of 2,4-dinitro-6-t-butyl-3-methylanisole or musk ambrette.The process according to the invention is characterized in that 6-t-butyl-3-methylanisole is reacted with a nitrating mixture consisting of 30 to 50% of acetic acid, 20 to 30% of acetic anhydride and 25 to 45% by weight of nitric acid, at between 7.degree. and 15.degree. C. The product is recovered in the pure state with a good yield by adding small amounts of water to the crude reaction mixture.Application: Synthesis of a scented product.
    Type: Grant
    Filed: December 18, 1978
    Date of Patent: November 25, 1980
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Helene M. Pascal, Jean-Marie L. Emeury
  • Patent number: 4233463
    Abstract: The invention relates to a process for the separation of 2,4-dinitro-6-t-butyl-3-methylanisole, referred to as musk ambrette, from the crude mixtures in which it is present, which are obtained by nitrating 6-t-butyl-3-methylanisole.According to the invention, an amount of water representing from 5 to 40% by weight of the nitrating mixture used in the synthesis is introduced onto the crude synthesis mixture in a first addition, the pure musk ambrette obtained is collected and several small amounts of water, representing from 1 to 15% by weight of the said nitrating mixture used, are then introduced, the precipitated product being collected between each addition. The process makes it possible to collect, in a pure form and without the use of an organic extraction solvent, about three quarters of the musk ambrette present in the crude synthesis mixture.
    Type: Grant
    Filed: December 18, 1978
    Date of Patent: November 11, 1980
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Helene M. Pascal, Jean-Marie L. Emeury
  • 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: 4220804
    Abstract: Substituted gem-dinitroalkanes are prepared by reacting a nitro olefin, tetranitromethane and an alcohol or organolithium derivative. The substituted gem-dinitroalkanes are useful as explosives, plasticizers and binders.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: September 2, 1980
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Arnold T. Nielsen, Clifford D. Bedford
  • Patent number: 4216152
    Abstract: This invention relates to an improved process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines which are useful intermediates in the synthesis of agricultural herbicides.This process of the invention comprises reacting a 2-substituted aniline with N-chloromethylpyrrolidone at about room temperature in the presence of an acid acceptor. Such room temperature alkylation of the aniline prevents excessive side reactions, particularly with a substituent in the 2-position of the aniline, such as an alkenyl group, which is sensitive to alkylating agents which require excessive heating to effective the condensation reaction.
    Type: Grant
    Filed: December 14, 1978
    Date of Patent: August 5, 1980
    Assignee: GAF Corporation
    Inventors: Louis Schneider, David E. Graham
  • Patent number: 4192949
    Abstract: Phenol ethers are prepared by reacting phenols with dialkyl carbonates in the presence of tertiary amines and/or phosphines. The aralkyl aryl ethers and alkyl aryl ethers obtained are starting materials for the manufacture of dyes, crop protection agents and scents.
    Type: Grant
    Filed: June 15, 1978
    Date of Patent: March 11, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae, Ludwig Schroff, deceased
  • Patent number: 4187247
    Abstract: Novel 9-substituted phenyl-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: March 8, 1979
    Date of Patent: February 5, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4182911
    Abstract: Novel optically-active (S)- 1-aryloxy-2,3-epoxy-propane derivatives, a process for their manufacture, various intermediates used in the preparation thereof, and a process for using them for the manufacture of optically-active (S)-1-aryloxy-3-amino-2-propanol derivatives useful as .beta.-adrenergic blocking agents.
    Type: Grant
    Filed: December 20, 1977
    Date of Patent: January 8, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventor: Howard Tucker
  • Patent number: 4163057
    Abstract: Compounds of the formula ##STR1## where R.sub.1 is hydrogen or lower alkyl, andR.sub.2 is hydrogen or straight chain lower alkyl, andR.sub.3 is hydrogen, fluoro, chloro, lower alkoxy, lower alkyl or trifluoromethyl, andN is 1, 2, 3, and 4,Which are useful as minor tranquilizers, sleep inducers and muscle relaxants.
    Type: Grant
    Filed: December 27, 1977
    Date of Patent: July 31, 1979
    Assignee: Sandoz, Inc.
    Inventor: Jeffrey Nadelson
  • Patent number: 4157344
    Abstract: A one-step process for the synthesis of aryl trifluoromethyl ethers by reacting phenol or certain substituted phenols with a perhalomethane and hydrogen fluoride is provided. The compounds produced by the process of this invention are useful intermediates in the production of dyestuffs and pharmaceuticals.
    Type: Grant
    Filed: January 16, 1978
    Date of Patent: June 5, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Andrew E. Feiring
  • Patent number: 4125563
    Abstract: I have discovered a process for making nitroarylacetylenes and aminoarylacetylenes in which the aryl radical is a phenylene radical or a diphenylene radical. With the exception of p-aminophenylacetylene, the compounds produced by this process are novel. The compounds are all useful as intermediates in the preparation of addition polymers utilizing a polymeric backbone of polyimides. The addition polymers are useful as adhesives and as laminating resins.
    Type: Grant
    Filed: August 26, 1977
    Date of Patent: November 14, 1978
    Assignee: Hughes Aircraft Company
    Inventor: Robert H. Boschan