The Additional Ring Is Benzene Patents (Class 568/744)
  • Patent number: 4599464
    Abstract: Novel compositions useful as antioxidants are formed by the reaction of resorcinol with an alkenylbenzene.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: July 8, 1986
    Assignee: Koppers Company, Inc.
    Inventor: Hans Dressler
  • Patent number: 4594460
    Abstract: Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: June 10, 1986
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4590301
    Abstract: Compounds of the general formula ##STR1## wherein n, R.sub.1, R.sub.2 and X are defined herein, are effective inhibitors of polymerization of vinylic monomers, particularly acrylic monomers. The inhibitors are easily, efficiently, and thoroughly removed from solution with the monomer by contact with charcoal.
    Type: Grant
    Filed: October 24, 1984
    Date of Patent: May 20, 1986
    Assignee: Barnes-Hind, Inc.
    Inventors: Drahoslav Lim, Peter C. Morris
  • Patent number: 4532367
    Abstract: A method is provided for the production of antimicrobially effective phenol derivatives according to general Formula I in which R.sub.1 is bromine or chlorine, R.sub.2 is methyl or ethyl, R.sub.3 is hydrogen or sodium, potassium, ammonium or by alkyl with up to 10 C-atoms substituted ammonium, magnesium, calcium, barium, aluminum, tin, bismuth, copper, zinc, R.sub.4 and R.sub.5 are independently hydrogen, alkyl or alkoxy with up to 5 C-atoms, bromine or chlorine. The compounds are obtained by benzylation of 6-halogen- or 4-halogen-2-alkylphenol, halogenation of 2-alkyl-4-benzylphenol or -6-benzylphenol, or by alkylation of 6-halogen-4-benzylphenol or of 4-halogen-6-benzylphenol and if necessary through reaction of the product with hydroxide, alcoholate, carbonate or hydrogen carbonate of the above-mentioned metals. Water or lipid soluble effective substances are obtained which display a broad antimicrobial activity spectrum.
    Type: Grant
    Filed: August 30, 1982
    Date of Patent: July 30, 1985
    Assignee: VEB Jenapharm
    Inventors: Herbert Teubner, Axel Kramer, Wolfgang Weuffen, Eberhard Schrotter, Gerhard Grubel
  • Patent number: 4514577
    Abstract: Phenols having an unsubstituted ortho-position are benzylated by reaction with a benzyl alcohol in contact with an activated alumina catalyst especially gamma alumina at a temperature sufficient to maintain the reactants in the vapor phase.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: April 30, 1985
    Assignee: Ethyl Corporation
    Inventors: Allen H. Filbey, Henry G. Braxton, Jr., Bernard R. Meltsner
  • Patent number: 4510338
    Abstract: The invention relates to new resorcin derivatives of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 3 carbon atoms or alkoxy having from one to 3 carbon atoms.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 9, 1985
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
  • Patent number: 4508926
    Abstract: The invention relates to new 4-hydroxy-benzhydrols of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms, with the proviso that if R.sub.1 is hydrogen, R.sub.2 is other than hydrogen or a 3-trifluoromethyl group, or if R.sub.1 is a 2-methyl group, R.sub.2 is other than a 5-methyl group.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredients are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 2, 1985
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
  • Patent number: 4506103
    Abstract: o-Benzylphenol is prepared by reacting phenol with dibenzyl ether in the presence of .gamma.-aluminum oxide as a condensation agent.o-Benzylphenol is used, inter alia, as such or, after chlorination, in the form of chlorobenzylphenols, as a microbicidal agent.
    Type: Grant
    Filed: September 6, 1983
    Date of Patent: March 19, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz-Peter Hemmerich, Werner Schulte-Huermann, Heinz Dohm
  • 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: 4410739
    Abstract: Meta-chlorophenols useful as intermediates in various organic syntheses are prepared by selectively catalytically hydrodechlorinating a polychlorophenol in liquid organic phase and in the presence of a nobel metal catalyst and a Lewis acid, said polychlorophenol bearing chlorine substituents in both the meta- and ortho- and/or para-positions.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: October 18, 1983
    Assignee: Rhone-Poulenc Industries
    Inventor: Georges Cordier
  • Patent number: 4398047
    Abstract: 2-Substituted-4,6-di-t-butylresorcinol represented by the general formula: ##STR1## wherein R represents a straight or branched alkyl group having 1 to 20 carbon atoms, a straight or branched alkenyl group having 2 to 20 carbon atoms and at least one double bond, or an aralkyl group, wherein no tertiary carbon atom of R is directly bonded to the benzene nucleus, is prepared by allowing 4,6-di-t-butylresorcinol to react with a halogen compound represented by the general formula:RXwherein R has the same meaning as defined above, and X represents a halogen atom, excluding the X bonded to a tertiary carbon of R, in an aqueous alkali solution. By further debutylization of the 2-substituted-4,6-t-butylresorcinol, 2-substituted resorcinol represented by the general formula: ##STR2## wherein R has the same meaning as defined above, but the tertiary carbon of R is free from direct bonding to the benzene nucleus, is prepared.
    Type: Grant
    Filed: February 23, 1982
    Date of Patent: August 9, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukihisa Takisawa, Shinichi Hasegawa
  • Patent number: 4391827
    Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.
    Type: Grant
    Filed: July 27, 1981
    Date of Patent: July 5, 1983
    Assignee: Pfizer Inc.
    Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4390735
    Abstract: A process for the preparation of a p-allylphenol of the formula I, which comprises reacting a phenol of the formula II with an allyl halide of the formula III ##STR1## in which the symbols R.sub.1 to R.sub.6 and X are as defined in the description, in the presence of a base and a phase transfer catalyst.p-Allylphenols are valuable intermediates and lubricant additives.
    Type: Grant
    Filed: October 13, 1981
    Date of Patent: June 28, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Siegfried Rosenberger
  • Patent number: 4366330
    Abstract: An intermediate useful in the production of liquid crystal esters has a molecular structure ##STR1## in which of the groups R' and R" one is fluorine and the other is hydrogen, and in which R is an alkyl group having more than one carbon atom, an aryl substituted alkyl group or a cyclohexyl substituted alkyl group.These compounds may be prepared from the corresponding alkoxy compounds ##STR2## where R'" is a protective alkyl group such as methyl. These compounds may be used in the production of liquid crystal esters by a conventional esterification with carboxylic acids, or acid derivative, eg chloride, eg containing the radical ##STR3## where X is an alkyl group and ##STR4## is a benzene or cyclohexane ring.
    Type: Grant
    Filed: September 30, 1980
    Date of Patent: December 28, 1982
    Assignees: BCH Chemicals Limited, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: George W. Gray, David Lacey, John A. Jenner, Martin G. Pellatt
  • Patent number: 4357344
    Abstract: Certain polybutylbenzylphenols and benzyl-3,4-methylenedioxybenzenes are useful for insect control especially as insect chemosterilants and oviposition inhibitors. The benzyl-3,4-methylenedioxybenzenes also find utility as growth inhibitors for mosquito larvae.
    Type: Grant
    Filed: March 29, 1979
    Date of Patent: November 2, 1982
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Leonard Jurd
  • Patent number: 4342777
    Abstract: Certain polybutylbenzylphenols and benzyl-3,4-methylenedioxybenzenes are useful for insect control especially as insect chemosterilants and oviposition inhibitors. The benzyl-3,4-methylenedioxybenzenes also find utility as growth inhibitors for mosquito larvae.
    Type: Grant
    Filed: November 5, 1981
    Date of Patent: August 3, 1982
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Leonard Jurd
  • Patent number: 4320235
    Abstract: 1-(Aralkyl)-2-naphthols are prepared by reacting a 2-naphthol with a styrene in the presence of a carboxylic acid.The 1-(aralkyl)-2-naphthols obtainable by the process according to the invention are valuable starting materials for the preparation of dyes, pest control agents, drugs, ointments, emulsifiers, dispersants, stabilizers, hydraulic fluids, plasticizers, corrosion inhibitors, disinfectants, crop protection agents and scents.
    Type: Grant
    Filed: November 21, 1980
    Date of Patent: March 16, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Gerhard Nestler
  • Patent number: 4316996
    Abstract: Detrimental color change of phenolic antioxidants during production, storage and use in rubbers is inhibited by adding during the synthesis of the phenolic antioxidant a disubstituted hydroxylamine to the catalyst neutralization solution and a substituted oxime together with a disubstituted hydroxylamine to the reaction mixture prior to filtration.
    Type: Grant
    Filed: November 17, 1980
    Date of Patent: February 23, 1982
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Jacques H. Collonge, Hans Widmer
  • Patent number: 4284830
    Abstract: Monohalogenated hydrocarbyl substituted phenols can be produced by reacting hydrocarbyl substituted phenols with a halogen carrying out the reaction in a diluent such as benzene, alkyl substituted benzenes, and halosubstituted hydrocarbons of 1-3 carbon atoms.
    Type: Grant
    Filed: February 1, 1980
    Date of Patent: August 18, 1981
    Assignee: Phillips Petroleum Co.
    Inventors: Ronald D. Knudsen, Darryl R. Fahey
  • Patent number: 4275071
    Abstract: Imidazole derivatives of the formula I and pharmaceutically acceptable acid addition salts thereof are provided: ##STR1## In the formula, R.sub.4 1- or 2-naphthyl, optionally substituted with Cl, Br, or I; 1,2,3,4-tetrahydro-6-naphthyl; 3-duryl, optionally 6-substituted by Cl, Br, I, NO.sub.2, CH.sub.3 or benzyl; mesityl, phenyl 2-, 3- or 4-substituted by OH, NH.sub.2, NO.sub.2, CH.sub.3 CONH, phenyl, phenoxy, cyclohexyl, phenylthio, benzylthio, C.sub.1 -C.sub.6 alkyl or C.sub.1 C.sub.6 alkylthio; 4-bibenzylyl; 3,4-dihydroxyphenyl,n=0, 1 or 2 and(a) R=H, alkyl having 1 to 6 carbon atoms or phenyl R.sub.1 =H, alkyl having 1 to 6 carbon atoms or phenyl one of R.sub.2 and R.sub.3 =H the other of R.sub.2 and R.sub.3 =H, OH, benzoyloxy, C.sub.2 -C.sub.7 alkanoyloxy, N-(C.sub.1 -C.sub.6 alkyl)-carbamoyloxy, N,N-[di-(C.sub.1 C.sub.6)alkyl]-carbamoyloxy, but if R.sub.2 =R.sub.3 =H then R=R.sub.1 =H, or(b) R=H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.1 =H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.2 +R.sub.
    Type: Grant
    Filed: July 10, 1979
    Date of Patent: June 23, 1981
    Assignee: Recordati S.A.
    Inventors: Dante Nardi, Alberto Tajano, Maria J. Magistretti
  • Patent number: 4212762
    Abstract: Novel mesomorphic substances, constituting, in certain temperature ranges, nematic or smectic liquid crystals which are compounds of the formula: ##STR1## wherein R.sub.1 is an alkyl or alkoxy group containing 1 to 10 atoms of carbon;R.sub.2 is Br, CN or an alkyl (or an alkoxy) group containing 1 to 10 atoms of carbon.
    Type: Grant
    Filed: November 21, 1978
    Date of Patent: July 15, 1980
    Assignee: Thomson-CSF
    Inventors: Jean-Claude Dubois, Huu Tinh Nguyen, Annie Zann
  • Patent number: 4202199
    Abstract: Alkylphenol compounds are manufactured by continuous reaction of phenolic compounds with olefins in the presence of a pulverulent polystyrenesulfonic acid exchanger suspended in the reaction mixture. The products are starting materials for the manufacture of dyes, pesticides, pharmaceuticals, emulsifiers, dispersing agents, stabilizers, antioxidants, plasticizers, corrosion inhibitors, disinfectants, seed dressings, aging inhibitors, crop protection agents and scents.
    Type: Grant
    Filed: October 6, 1977
    Date of Patent: May 13, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Gerhard Nestler
  • Patent number: 4201878
    Abstract: Bisphenols substantially free of by-products, are produced rapidly by reacting a phenol and a compound of the formulae: ##STR1## wherein R and R' are hydrogen, lower alkyl or aryl; X is lower alkoxy or the same as X'; Y is chlorine or the same as X; X' is aryloxy; Z is a 1,2- or 1,3-propylenedioxy (that may optionally carry hydroxy, lower alkyl or lower hydroxyalkyl substituents), or arylenedioxy radical; n is integer from three to nine; m is (n-1).
    Type: Grant
    Filed: February 10, 1978
    Date of Patent: May 6, 1980
    Assignee: General Electric Company
    Inventors: Victor Mark, Lawrence C. Mitchell, Charles V. Hedges
  • Patent number: 4182915
    Abstract: Process for the preparation of nucleophilically ring-substituted aromatic compounds from an aromatic-thallium (III) metallate is provided in which the aromatic-thallium (III) metallate is contacted with a source of the nucleophile to form the desired substituted aromatic compound, which may be recovered from the reaction mixture as by distillation. Exemplary processes include the preparation of aniline and phenol from benzene.
    Type: Grant
    Filed: January 24, 1977
    Date of Patent: January 8, 1980
    Assignee: Halcon International, Inc.
    Inventor: Robert J. Harvey
  • Patent number: 4174460
    Abstract: A process for the hydroxylation of phenols and phenol ethers in the nucleus with hydrogen peroxide wherein a phenol or a phenol ether is reacted at the start of the reaction with substantially anhydrous hydrogen peroxide and wherein the reaction is carried out in the presence of a strong acid.
    Type: Grant
    Filed: March 31, 1977
    Date of Patent: November 13, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Seifert, Helmut Waldman, Wulf Schwerdtel, Wolfgang Swodenk
  • Patent number: 4160113
    Abstract: The present invention is related to a process for the manufacture of resorcinols by catalytic dehydrogenation of cyclohexane diones-(1,3) in the liquid phase by means of a dehydrogenating mixture consisting of a solvent and of a catalyst containing a noble metal from Group VIII of the Periodic Table.
    Type: Grant
    Filed: November 11, 1977
    Date of Patent: July 3, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner H. Muller, Knut Riedel, Hans Krekeler
  • Patent number: 4147726
    Abstract: An organic hydroperoxide is hydrolyzed by acid-catalysis in a reaction medium comprising essentially a mixture of a polar solvent, e.g. a low boiling, low molecular weight alcohol and/or sulfolane and phenol. Specifically cyclohexanone and phenol are obtained from cyclohexylbenzene hydroperoxide.
    Type: Grant
    Filed: November 8, 1976
    Date of Patent: April 3, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Yulin Wu
  • Patent number: 4147872
    Abstract: Azacycloalkanes, and derivatives thereof, including unsaturated analogs, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.
    Type: Grant
    Filed: September 13, 1977
    Date of Patent: April 3, 1979
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4117243
    Abstract: A process for preparing o-benzylphenol is disclosed. The process comprises heating benzyl phenyl ether, either in liquid or vapor phase, in the presence of an effective amount of activated alumina catalyst.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: September 26, 1978
    Assignee: Continental Oil Company
    Inventors: Charles M. Starks, Allan J. Lundeen
  • Patent number: 4105698
    Abstract: A process for preparing ortho-substituted cinnamyl phenols is disclosed. The process comprises heating a mixture of cinnamyl alcohol and phenol in the presence of an effective amount of activated alumina.
    Type: Grant
    Filed: February 16, 1977
    Date of Patent: August 8, 1978
    Assignee: Continental Oil Company
    Inventors: Charles M. Starks, Allan J. Lundeen
  • Patent number: 4105699
    Abstract: A process for preparing o-benzylphenol in high selectivity is disclosed. The process comprises heating a mixture of benzyl alcohol and phenol in the presence of an effective amount of activated alumina as a catalyst.
    Type: Grant
    Filed: February 16, 1977
    Date of Patent: August 8, 1978
    Assignee: Continental Oil Company
    Inventor: Charles M. Starks
  • Patent number: 4098829
    Abstract: Polymeric hydroquinones of the structure ##STR1## WHEREIN N IS FROM 3 TO 10,000 INCLUSIVE AND R and R' independently are hydrogen or a lower alkyl, are disclosed, as is the preparation and the use of such materials, especially as nonabsorbable polymeric antioxidants for edible materials.
    Type: Grant
    Filed: May 19, 1977
    Date of Patent: July 4, 1978
    Assignee: Dynapol
    Inventors: Ned M. Weinshenker, James A. Dale
  • Patent number: 4091225
    Abstract: This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.
    Type: Grant
    Filed: January 22, 1974
    Date of Patent: May 23, 1978
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Dane K. Parker
  • Patent number: 4087554
    Abstract: The disclosure relates to a method for use in the practice of animal husbandry which comprises the oral administration to non-ruminant animals of an iodonium salt. Solid or liquid compositions of said iodonium salts for use in the said method are also disclosed. Certain of the iodonium sats used in the said method are novel compounds.
    Type: Grant
    Filed: October 14, 1975
    Date of Patent: May 2, 1978
    Assignee: Imperial Chemical Industries Limited
    Inventors: David Bryan Haydock, Michael James Smithers
  • Patent number: 4087410
    Abstract: 2,6-Dimethoxyphenol reacts with a tertiary carbinol in the presence of an acid to provide exclusively a 1-hydroxy-2,6-dimethoxy-4-tertiary alkyl)benzene, which when reacted with a halogenated disubstituted phosphite affords a 2,6-dimethoxy-4-tertiary alkyl)phenyl disubstituted phosphate. Reduction of the phenyl phosphate derivative by reaction with an alkali metal affords a 1-(tertiary alkyl)-3,5-dimethoxybenzene, which upon reaction with a demethylating agent provides a 5-(tertiary alkyl)resorcinol.
    Type: Grant
    Filed: June 14, 1976
    Date of Patent: May 2, 1978
    Assignee: Eli Lilly and Company
    Inventors: Samuel J. Dominianni, Charles W. Ryan