Ether Oxygen Bonded Directly To Benzene Ring Patents (Class 568/584)
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Patent number: 4847426Abstract: 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: GrantFiled: May 25, 1988Date of Patent: July 11, 1989Assignee: Hoechst AktiengesellschaftInventors: Dieter Heck, Hartmut Heise, Manfred Hintzmann
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Patent number: 4782190Abstract: 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: GrantFiled: March 6, 1987Date of Patent: November 1, 1988Assignee: Bayer AktiengesellschaftInventors: Josef Kasbauer, Karlfried Wedemeyer
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Patent number: 4613682Abstract: 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: GrantFiled: August 19, 1985Date of Patent: September 23, 1986Assignee: The Dow Chemical CompanyInventor: Kathryn A. Eickholt
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Patent number: 4605745Abstract: 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: GrantFiled: December 24, 1984Date of Patent: August 12, 1986Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Daniel A. Singleton
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Patent number: 4595763Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.Type: GrantFiled: June 27, 1983Date of Patent: June 17, 1986Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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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: 4537999Abstract: 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: GrantFiled: September 21, 1983Date of Patent: August 27, 1985Assignees: Chisso Corporation, Kaken Pharmaceutical Co., Ltd.Inventors: Tetsuya Ogawa, Shinichi Saitoh, Takeshi Inoi, Masaji Kato, Heitaro Obara
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Patent number: 4513141Abstract: 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: GrantFiled: April 28, 1983Date of Patent: April 23, 1985Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Daniel A. Singleton
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Patent number: 4479015Abstract: 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: GrantFiled: January 7, 1983Date of Patent: October 23, 1984Assignee: GADOT, Petrochemical Industries, Ltd.Inventors: Yoel Sasson, Shmuel Zbaida
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Patent number: 4454355Abstract: 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: GrantFiled: May 24, 1982Date of Patent: June 12, 1984Assignee: Hoechst AktiengesellschaftInventors: Hans Schubert, Konrad Baessler
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Patent number: 4424365Abstract: 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: GrantFiled: June 22, 1982Date of Patent: January 3, 1984Assignee: The Upjohn CompanyInventor: Wendell Wierenga
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Patent number: 4423229Abstract: 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: GrantFiled: February 8, 1982Date of Patent: December 27, 1983Assignee: The Upjohn CompanyInventor: Wendell Wierenga
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Patent number: 4415744Abstract: 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: GrantFiled: October 21, 1981Date of Patent: November 15, 1983Assignee: Monsanto CompanyInventors: Ignatius Schumacher, Kang-Bo Wang
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Patent number: 4376868Abstract: 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: GrantFiled: February 14, 1980Date of Patent: March 15, 1983Assignee: Conoco Inc.Inventors: Gerald L. Nield, Kang Yang, Paul H. Washecheck
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Patent number: 4349487Abstract: 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: GrantFiled: August 24, 1981Date of Patent: September 14, 1982Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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Patent number: 4341905Abstract: 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: GrantFiled: August 18, 1980Date of Patent: July 27, 1982Assignee: The Dow Chemical CompanyInventor: Paul E. Strege
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Patent number: 4328166Abstract: 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: GrantFiled: November 21, 1980Date of Patent: May 4, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Fumio Fujita, Hiroshi Kishida, Nobushige Itaya, Ichiki Takemoto
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Patent number: 4314086Abstract: 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: GrantFiled: June 20, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Daniel Michelet
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Patent number: 4288638Abstract: 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: GrantFiled: February 19, 1980Date of Patent: September 8, 1981Assignee: Societe Nationale des Poudres et ExplosifsInventors: Helene M. Pascal, Jean-Marie L. Emeury
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Patent number: 4287125Abstract: 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: GrantFiled: June 20, 1980Date of Patent: September 1, 1981Assignee: Rhone-Poulenc IndustriesInventor: Gerard Soula
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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: 4257943Abstract: 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: GrantFiled: August 14, 1978Date of Patent: March 24, 1981Assignee: Hoechst AktiengesellschaftInventor: Reinhard Hahnle
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Patent number: 4236029Abstract: 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: GrantFiled: December 18, 1978Date of Patent: November 25, 1980Assignee: Societe Nationale des Poudres et ExplosifsInventors: Helene M. Pascal, Jean-Marie L. Emeury
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Patent number: 4233463Abstract: 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: GrantFiled: December 18, 1978Date of Patent: November 11, 1980Assignee: Societe Nationale des Poudres et ExplosifsInventors: Helene M. Pascal, Jean-Marie L. Emeury
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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: 4220804Abstract: 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: GrantFiled: November 20, 1978Date of Patent: September 2, 1980Assignee: The United States of America as represented by the Secretary of the NavyInventors: Arnold T. Nielsen, Clifford D. Bedford
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Patent number: 4216152Abstract: 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: GrantFiled: December 14, 1978Date of Patent: August 5, 1980Assignee: GAF CorporationInventors: Louis Schneider, David E. Graham
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Patent number: 4192949Abstract: 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: GrantFiled: June 15, 1978Date of Patent: March 11, 1980Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae, Ludwig Schroff, deceased
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Patent number: 4187247Abstract: Novel 9-substituted phenyl-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives useful as anti-tumor agents.Type: GrantFiled: March 8, 1979Date of Patent: February 5, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
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Patent number: 4182911Abstract: 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: GrantFiled: December 20, 1977Date of Patent: January 8, 1980Assignee: Imperial Chemical Industries LimitedInventor: Howard Tucker
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Patent number: 4163057Abstract: 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: GrantFiled: December 27, 1977Date of Patent: July 31, 1979Assignee: Sandoz, Inc.Inventor: Jeffrey Nadelson
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Patent number: 4157344Abstract: 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: GrantFiled: January 16, 1978Date of Patent: June 5, 1979Assignee: E. I. Du Pont de Nemours and CompanyInventor: Andrew E. Feiring
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Patent number: 4125563Abstract: 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: GrantFiled: August 26, 1977Date of Patent: November 14, 1978Assignee: Hughes Aircraft CompanyInventor: Robert H. Boschan