Oxy Containing Reactant Patents (Class 568/322)
  • Patent number: 5023381
    Abstract: A process is described for the preparation of 2-methoxy-6-propionyl-naphthalene, an intermediate in the synthesis of naproxen.The process consists of Friedel-Crafts acylation of 2-methoxy-naphthalene, and obviates the drawbacks related to the use of nitrobenzene as solvent.
    Type: Grant
    Filed: December 20, 1989
    Date of Patent: June 11, 1991
    Assignee: Zambon Group S.p.A.
    Inventors: Giulio Perdoncin, Claudio Giordano, Maurizio Paiocchi, Roberto Casagrande
  • Patent number: 5019655
    Abstract: Method of preparing 4-disubstituted phenyl-1-tetralones of formula ##STR1## in which X represents halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and Y, situated in position 2' or 3', represents halogen or C.sub.1 -C.sub.4 alkyl, this method being characterized in that it comprises the reaction, in the presence of an acid agent, of .alpha.-naphthol of formula (II) with a phenyl compound of formula (III): ##STR2## where X represents halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and Y is situated in the ortho or meta position with respect to X and represents halogen or C.sub.1 -C.sub.4 alkyl.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: May 28, 1991
    Assignee: Delalande S.A.
    Inventor: Guy P. Adrian
  • Patent number: 5008461
    Abstract: Benzyl ketones of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.8 -alkyl which is unsubstituted or substituted by cycloalkyl or aryl and R.sup.2 and R.sup.3 are each halogen, C.sub.1 -C.sub.4 -alkyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.2 -C.sub.4 -methylenedioxy, are prepared by a process in which a glycol monoether of the general formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings and R.sup.4 is C.sub.1 -C.sub.8 -alkyl, is converted in the presence of silica, a phosphate or a zeolite at from 50.degree. to 500.degree. C. and under from 0.01 to 50 bar.
    Type: Grant
    Filed: March 7, 1990
    Date of Patent: April 16, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz Naeumann, Eckhard Hickmann
  • Patent number: 4990680
    Abstract: A process for the preparation of 2,4-dihydroxybenzophenone by reacting resorcinol with benzotrichloride in water, wherein the reaction mixture contains a surfactant or a dispersing or emulsifying agent in a concentration of from 0.05 to 5%, by weight of the water.The product is obtained in high yield and good purity.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Alexander Aumueller
  • Patent number: 4982006
    Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: January 1, 1991
    Assignee: Norwich Eaton Pharmaceuticals, Inc.
    Inventor: Thomas T. Hudec
  • Patent number: 4967009
    Abstract: This invention relates to a method for manufacturing aromatic compounds having the following formula (II) comprising the step of reacting an unsaturated aromatic compound having the following formula (I) with an aryl compound containing an iodosyl group or the salt thereof within a temperature range of from -50.degree. to 200.degree. C.
    Type: Grant
    Filed: July 7, 1989
    Date of Patent: October 30, 1990
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Kouichi Iwamoto
  • Patent number: 4967011
    Abstract: The present invention relates to a process for decomposing an aromatic acylated compound.HF-BF.sub.3 complex in preparing an aromatic acylated compound by decomposing an aromatic acylated compound.HF-BF.sub.3 complex obtained by reacting an aromatic compound with an acylating agent in the presence of HF-BF.sub.3 as a catalyst, which comprises subjecting the aromatic acylated compound.HF-BF.sub.3 complex to thermal decomposition in the presence of at least one aromatic hydrocarbon (A.H.) selected from benzene, toluene and chlorobenzene and at least one saturated aliphatic hydrocarbon (S.H.) selected from pentane, hexane and cyclohexane, as a decomposing agent.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: October 30, 1990
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Nobuyuki Tokura, Tadayoshi Takefumi, Shunichi Matsumoto, Tatsuhiko Yanagawa, Yoshihiro Shiokawa, Ichiyo Ohtsuka
  • Patent number: 4960943
    Abstract: Phenylketones etherified in the 4-position can be prepared by reaction of aromatic ethers which have a free 4-position with acylating agents, the acylation being carried out in the presence of zeolite catalysts having pore sizes of at least 5 .ANG..
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: October 2, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Artur Botta, Hans-Josef Buysch, Lothar Puppe, Dieter Arlt
  • Patent number: 4922026
    Abstract: Aromatic diketones are prepared by a process comprising contacting at least one acylatable aromatic compound and at least one aromatic diacyl halide in the presence of catalytic amounts of ferric chloride or ferric oxide at an elevated temperature and at superatmospheric conditions.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: May 1, 1990
    Assignee: The Dow Chemical Company
    Inventors: Robert B. Baker, Jr., R. Garth Pews, Eric W. Otterbacher, James A. Gall
  • Patent number: 4918237
    Abstract: 1,4-Bis(4-phenoxybenzoyl)benzene is made in a homogeneous or heterogeneous system by a reaction of diphenyl ether with 1,4-benzenedicarbonyl chloride at 220.degree.-258.degree. C. in the presence of certain iron, gallium, and indium compounds in catalytic amounts. The mole ratio of diphenyl ether to 1,4-dicarbonyl chloride is 5:1 to 25:1 and the mole ratio of 1,4-benzenedicarbonyl chloride to the catalyst is 1000:1 to 10:1.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: April 17, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: David R. Corbin, Enio Kumpinsky
  • Patent number: 4906658
    Abstract: Compounds of Formula I ##STR1## the pharmaceutically acceptable salts, and the gamma-lactone form thereof are described. They are antagonists of leukotrienes and SRS-A.
    Type: Grant
    Filed: April 21, 1987
    Date of Patent: March 6, 1990
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Haydn W. R. Williams, Robert N. Young
  • Patent number: 4898983
    Abstract: Friedel Crafts preparation of aryl carbonyl compounds having an exceptionally high degree of isomeric purity and freedom from by-products can be achieved by adding to the Lewis acid reaction system a protic controlling agent selected from ROX, water, RCOOX, RSO.sub.3 X, and ROY, wherein R is organic, X is hydrogen or metal, and Y is metal. Contrary to conventional expectation, the protic agent does not significantly alkylate or acylate the Friedel Crafts reaction product.
    Type: Grant
    Filed: November 7, 1988
    Date of Patent: February 6, 1990
    Assignee: Raychem Limited
    Inventor: Ian D. H. Towle
  • Patent number: 4898988
    Abstract: A process for the preparation of .beta.-hydroxyketones comprising the catalytic hydrogenolysis of an aqueous solution of isoxazolines having the formula ##STR1## in a fixed bed reactor containing a transition metal catalyst at a temperature between 20.degree. to 150.degree. C. and a pressure from about 0 to 150 psig; wherein R.sub.1 and R.sub.2 are independently selected from hydrogen, alkyl, cycloalkyl or aromatic group and wherein the aqueous solution of isoxazolines is substantially free of acids or buffers.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: February 6, 1990
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: You-Jyh Lin, Harold Kloczewski
  • Patent number: 4868337
    Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moiety and R.sup.1 is an achiral organyl moeity.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 19, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4868338
    Abstract: The acylation of a naphthalene compound, substituted in the 2-position with an electron-donating group, with a reactive derivative of a lower aliphatic acid, in an aprotic organic diluent and in the presence of a Friedel Crafts catalyst consisting of a halide of an element having at least two valences, is improved when maintaining constant at any time the molar ratio of the naphthalene compound to the acylating agent and that of the acylating agent to the Friedel Crafts catalyst within specific ranges.
    Type: Grant
    Filed: March 8, 1988
    Date of Patent: September 19, 1989
    Assignee: Blaschim S.p.A.
    Inventors: Ambrogio Magni, Giuseppina Visentin
  • Patent number: 4845302
    Abstract: 5H-Dibenzo[a,d]cyclohepten-5-ones (I) ##STR1## (A and B being radicals for completing aromatic ring systems) are prepared by converting (Z)-2-(2-arylethenyl)arylcarboxylic acids (II) ##STR2## or E/Z-isomer mixtures thereof with a halogenating agent for carboxylic acids at from (-30.degree.) to +120.degree. C. to the corresponding carbonyl halides (III) ##STR3## where X is halogen, and cyclizing said carbonyl halides at from 0.degree. to 100.degree. C. in the presence of a Lewis acid.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: July 4, 1989
    Assignee: BASF Aktiengsellschaft
    Inventors: Marco Thyes, Gerd Steiner
  • Patent number: 4843179
    Abstract: A method of preparing 4,4'-diphenoxybenzophenone, comprising reacting diphenyl ether and carbon dioxide in the presence of a Friedel-Crafts catalyst and a promoting agent, preferably selected from the group consisting of phosphoryl chloride, phosphorus pentoxide, tetrachlorosilane, methyltrichlorosilane, dimethyldichlorosilane, titanium tetrachloride, zirconium tetrachloride, zirconium oxyhalide, and phosphorus pentachloride. In a preferred embodiment, the Friedel-Crafts catalyst is aluminum chloride and the promoting agent is phosphoryl chloride.
    Type: Grant
    Filed: January 5, 1988
    Date of Patent: June 27, 1989
    Assignee: Raychem Corporation
    Inventors: Viktors Jansons, Heinrich C. Gors
  • Patent number: 4835318
    Abstract: A process for the preparation of arylperfluoroalkyl ketones of the general formula I ##STR1## wherein R.sup.1 and R.sup.5 represent at least one of the substituents hydrogen, halogen, alkyl, alkoxy, alkylthio and perfluorinated alkyl, each having from 1 to 6 carbon atoms and n is an integer from 1 to 6, which comprises reacting an aryl carbonyl compound having the general formula II ##STR2## wherein R.sup.1 to R.sup.5 have the above-mentioned meaning and X as a monovalent moiety represents fluorine, chlorine or bromine and as a bivalent moiety the oxygen atom of an anhydride bridge, with a perfluoroalkyl halide of the general formula C.sub.n F.sub.2n+1 -Hal (III), wherein Hal represents chlorine, bromine or iodine and n is an integer from 1 to 6, in the presence of a trisdialkyl amide of phosphorus acid of the general formula P[N(alkyl)2]3 (IV).
    Type: Grant
    Filed: July 28, 1988
    Date of Patent: May 30, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Alfred Kruse, Gunter Siegemund, Klaus Schlich, Ingo Ruppert, deceased
  • Patent number: 4835319
    Abstract: 1,4-Bis(4-phenoxybenzoyl)benzene is made in a heterogeneous system by a reaction of diphenyl ether with 1,4-benzenedicarbonyl chloride at 190.degree.-250.degree. C. in the presence of a zeolite catalyst having a ring structure containing 12 oxygen atoms, which can be either an activated zeolite in hydrogen form or an iron-exchanged zeolite, which zeolite can be readily separated from the hot liquid phase in the reaction mixture. The mole ratio of diphenyl ether to 1,4-dicarbonyl chloride, when the catalyst is in hydrogen form, is about 50-80:1; when the catalyst is in iron-exhcanged form, it is about 10-50:1, and the weight ratio of 1,4-benzenedicarbonyl chloride to zeolite in hydrogen form is 3:1 to 1:2, while the ratio of 1,4-benzenedicarbonyl chloride to zeolite in iron-exchanged form is 10:1 to 1:32. The product readily crystallizes in a high state of purity from the cooled solution. 1,4-Bis(4-phenoxybenzoyl)benzene is a vaulable intermediate in the synthesis of polyetherketone resins.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: May 30, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: David R. Corbin, Enio Kumpinsky, Antonio Vidal
  • Patent number: 4827041
    Abstract: A process for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, wehrein diphenyl ether is contacted for about 30-360 minutes at 130.degree.-200.degree. C. with 1,4-benzenedicarbonyl chloride in respective mole ratios of about 15-80:1 in the presence of a fluorocarbon resin carrying pendant sulfonic acid groups, the weight ratio of the resin to 1,4-benzenedicarbonyl chloride being 3:1-1:2; the hot solution is separated from the resin, and the crystalline product is recovered from the solution on cooling. The so obtained 1,4-bis(4-phenoxybenzoyl)-benzene is a high purity material free of ortho-isomer and catalyst contamination and can be used without further purification as one of the starting materials in the preparation of polyetherketones, which are important engineering resins.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: May 2, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Thomas M. Ford, Enio Kumpinsky, Antonio Vidal
  • Patent number: 4824612
    Abstract: Aromatic ketones or .alpha.-diketones can be prepared from the corresponding carbinols by reaction with molar amounts of a sulfonyl chloride in the presence of a base. The corresponding sulfinic acid or salt thereof with the base is formed simultaneously.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: April 25, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Rutsch, Mario Slongo
  • Patent number: 4814508
    Abstract: Aromatic carbonyl compounds, in particular arylene ether ketones, are prepared by reacting an appropriate reagent system in the presence of free Lewis acid and a complex between a Lewis acid, for example, aluminum trichloride, and a Lewis base, for example, N,N-dimethylformamide, and, optionally, a diluent, such as methylene chloride. The process is particularly advantageous for the preparation of substantially or all para-linked arylene ether ketones as the presence of the Lewis acid/Lewis base complex markedly reduces alkylation and ensures the substantial absence of ortho substitution.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: March 21, 1989
    Assignee: Raychem Corporation
    Inventors: Heinrich C. Gors, Patrick J. Horner, Viktors Jansons
  • Patent number: 4803013
    Abstract: Novel halogenated naphthalene derivatives of the formula ##STR1## where X is F or Br, and a process for making the same are disclosed. Insulating oils are also disclosed which essentially comprise such a fluorine-containing compound and commonly used hydrocarbon insulating oils. The additive is highly conductive to improved dielectric constant, dielectric loss, hydrogen gas absorptivity, fluidity and viscosity characteristics.
    Type: Grant
    Filed: March 16, 1988
    Date of Patent: February 7, 1989
    Assignee: Nippon Oil Co., Ltd.
    Inventor: Nobuo Yokoyama
  • Patent number: 4772714
    Abstract: Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: September 20, 1988
    Assignee: Agency of Industrial Science & Technology
    Inventors: Masato Tanaka, Toshiyasu Sakakura
  • Patent number: 4764642
    Abstract: A process is described for preparing alpha-haloalkyl-aryl-ketones, comprising reacting a substantially anhydrous strong acid with a ketal of formula ##STR1## in which Ar, R, R.sub.1, R.sub.2 and X have the meanings given in the description.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: August 16, 1988
    Assignee: Zambon S.p.A.
    Inventors: Graziano Castaldi, Silvia Cavicchioli, Claudio Giordano
  • Patent number: 4694111
    Abstract: The production of a 1-hydroxy-2-lower alkoxyalkyl benzene, e.g. 2-(1'-methoxyethyl) phenol, is carried out by reacting phenol with a lower acetal or ketal, e.g., 1,1-dimethoxyethane at an elevated temperature in the presence of an H-ZSM-5 zeolite, as catalyst.
    Type: Grant
    Filed: July 9, 1986
    Date of Patent: September 15, 1987
    Assignee: Celanese Corporation
    Inventor: Balaram B. G. Gupta
  • Patent number: 4670603
    Abstract: Preparation of aryl alkyl ketones by reaction of an aryl compound with an aliphatic acid and/or a functional derivative thereof in anhydrous hydrofluoric acid.
    Type: Grant
    Filed: September 24, 1985
    Date of Patent: June 2, 1987
    Assignee: Blaschim S.p.A.
    Inventors: Oreste Piccolo, Giuseppina Visentin, Pietro Blasina, Franca Spreafico
  • Patent number: 4665246
    Abstract: The process of producing ethynyl aromatic compounds which are useful as intermediates in the preparation of 3-dimensional carbon-carbon structures for aerospace and military applications and as starting materials in the preparation of organic semi-conductors. The ethynyl aromatic compounds may be any of the classes illustrated in FIGS. 1, 2 and 3 of the drawing. Starting compounds for the process may by any compound from the classes illustrated in FIGS. 4, 5 and 6. The starting compound is reacted in the presence of a Friedel-Crafts catalyst in a suitable solvent with an acyl compound from the class illustrated in FIG. 7 to yield a compound within the classes illustrated in FIGS. 8, 9 and 10. The carbonyl groups in this compound are reduced to yield a corresponding alcohol. Each hydroxy group in the alcohol is converted to an easily eliminatable group, e.g., by reacting it with methane sulfonyl chloride, when subjected to basic conditions.
    Type: Grant
    Filed: March 9, 1984
    Date of Patent: May 12, 1987
    Assignee: Chem Biochem Research, Inc.
    Inventor: Chris Anderson
  • Patent number: 4647702
    Abstract: A method for the dehydroxylation of alpha-hydroxyketone using lithium diphenylphosphide. The alpha-hydroxyketone, e.g. benzoin, is reacted with a solution of lithium diphenylphosphide followed by the addition of either an alkyl halide, e.g. methyliodide, or an alkyl halide and an organic acid, e.g. acetic acid, to yield the dehydroxylated compound, e.g. desoxybenzoin.
    Type: Grant
    Filed: November 18, 1985
    Date of Patent: March 3, 1987
    Assignee: Stauffer Chemical Company
    Inventor: Andrea Leone-Bay
  • Patent number: 4628120
    Abstract: A preparing method of optically active ketones given by a general formula ##STR1## (wherein R represents a hydrocarbon group having 2 to 20 carbon atoms and R' represents a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon groups of R and R' may contain functional groups having no influence on the reaction. But, * represents an asymmetric carbon atom, and R represents a more electron donating group than R' (except when R=R') through the rearrangement reaction by using organoaluminum compound.
    Type: Grant
    Filed: October 16, 1984
    Date of Patent: December 9, 1986
    Assignee: Toyo Stauffer Chemical Co., Ltd.
    Inventors: Genichi Tsuchihashi, Keisuke Suzuki
  • Patent number: 4618726
    Abstract: A process for the preparation of benzophenones. A compound of the formula COX.sub.4 X.sub.5, where X.sub.4 and X.sub.5, which may be identical or different are halogen atoms, is reacted, in liquid hydrofluoric acid, with a deactivated benzene derivative, in the presence of boron trifluoride in such amount that the absolute pressure of boron trifluoride in the reaction space is at least one bar.
    Type: Grant
    Filed: December 18, 1984
    Date of Patent: October 21, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4618724
    Abstract: This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: October 21, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Hitosi Nozaki, Koichiro Oshima
  • Patent number: 4616095
    Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloakyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: October 7, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4613706
    Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: September 23, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4604486
    Abstract: A method of preparing optically active ketones having the general formula ##STR1## wherein R.sup.2 and R.sup.3 indicate hydrocarbon groups having 1 to 20 carbon atoms characterized by submitting an optically active sulfonyloxy alcohol having the general formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 indicate hydrocarbon groups having carbon atoms of 1 to 20 and which optionally contain N, O, P and S. The symbol * indicates asymmetric carbon atoms to rearrangement in a solvent and in the presence of organoaluminum compounds given by the general formula R.sub.3-n.sup.4 AlX.sub.n, (wherein R.sup.4 indicates an alkyl group having carbon atoms of 1 to 20 and X indicates a halogen atom, an alkoxy group or a CN group. n is 1, 1.5 or 2).
    Type: Grant
    Filed: January 4, 1985
    Date of Patent: August 5, 1986
    Assignee: Toyo Stauffer Chemical Co., Ltd.
    Inventors: Genichi Tsuchihashi, Keisuke Suzuki
  • Patent number: 4604485
    Abstract: Preparation of para-substituted 4-hydroxybenzophenones by forming poly(4-oxybenzoyl) in situ and reacting it with an appropriately substituted aromatic compound. The poly(4-oxybenzoyl) can be formed from a precursor such as 4-hydroxybenzoic acid by reaction with an agent which removes water from the acid to form the polymer. The reaction with the appropriately substituted aromatic compound, for example fluorobenzone, is effected in the presence of a Lewis acid compound such as aluminum chloride.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: August 5, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventor: Howard M. Colquhoun
  • Patent number: 4599452
    Abstract: Preparation of para-substituted 4-hydroxybenzophenones by reacting appropriately substituted aromatic compound with poly(4-oxybenzoyl) in the presence of an acid catalyst. The reaction with the appropriately substituted aromatic compound, for example fluorobenzene, is effected in the presence of an acid catalyst such as a strong proton acid or a Lewis Acid or a mixture thereof.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: July 8, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventors: Howard M. Colquhoun, Alan G. Breeze
  • Patent number: 4593125
    Abstract: Naphthalene substituted in the 2- or .beta.-position with an electron-donating substituent can be acylated with high regioselectivity in the 6-position by using an acylating agent in substantially anhydrous hydrogen fluoride which functions both as catalyst and solvent.
    Type: Grant
    Filed: March 13, 1985
    Date of Patent: June 3, 1986
    Assignee: Celanese Corporation
    Inventors: Kenneth G. Davenport, H. Clay Linstid, III
  • Patent number: 4568429
    Abstract: 2,4-Dihydroxybenzophenone is prepared substantially quantitatively and in a highly purified form by reacting resorcinol with a benzotrihalide in the presence of an aqueous solution of N-methylpyrrolidone and subsequently subjecting the crude reaction product mixture to vacuum distillation.
    Type: Grant
    Filed: March 2, 1984
    Date of Patent: February 4, 1986
    Assignee: GAF Corporation
    Inventor: Kou-Chang Liu
  • Patent number: 4568768
    Abstract: A method for producing m-hydroxy-acetophenone which comprises allowing m-(2-hydroxy-2-propyl)cumene hydroperoxide to react at 30.degree. to 100.degree. C. in the presence of an aqueous solution containing 0.001 to 1 mole of iron salt per mole of said compound, 0.01 to 4 moles of copper salt per mole of said iron salt, and mineral acid to give m-(2-hydroxy-2-propyl)acetophenone, then allowing the resulting compound to react at 30.degree. to 95.degree. C. in the presence of 1 to 20 moles of 5 to 90% by weight aqueous hydrogen peroxide solution per mole of said compound and acid catalyst to form m-(2-hydroperoxy-2-propyl)acetophenone, and further subjecting the product formed to acid decomposition. m-Hydroxyacetophenone is an important intermediate in the fields of pharmaceuticals, agricultural chemicals, dyestuffs and the like.
    Type: Grant
    Filed: December 13, 1984
    Date of Patent: February 4, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Nakamura, Seiichi Kai, Nobuharu Kono
  • Patent number: 4562287
    Abstract: Therapeutic compositions having anti-inflammatory and analgesic activity, containing as active compound 2-(4-biphenylyl)-4-hexenoic acid and/or derivatives thereof, characterized by low toxicity and by the absence or minimum level of ulcerogenic effect.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: December 31, 1985
    Assignee: Scharper S.p.A. per l'Industria Farmaceutica
    Inventors: Alfonso Del Vecchio, Grazia Sestini
  • Patent number: 4562294
    Abstract: Spiro[5.5]undeca-1,4,8-trien-3-ones are prepared by heating a reaction mixture consisting essentially of a 4-aminomethylphenol, a conjugated diene, and an inert solvent at a temperature of at least about 190.degree. C.
    Type: Grant
    Filed: October 15, 1984
    Date of Patent: December 31, 1985
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper
  • Patent number: 4560805
    Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4551554
    Abstract: A new process for production of 2-haloacetylphenols having the general formula ##STR1## (wherein, Y is halogen atom;m is an integer of 0-2,X and n have the same meaning as mentioned below),which comprises reacting phenols having the general formula ##STR2## (wherein, X is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.5 alkoxy or halogen atom;n is an integer of 0-2)with haloacetonitriles and boron halide compounds in the presence of condensing coagents.
    Type: Grant
    Filed: September 23, 1981
    Date of Patent: November 5, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tsutomu Sugasawa, Tatsuo Toyoda, Kazuyuki Sasakura
  • Patent number: 4524221
    Abstract: Process for the production of an acyloin comprising the steps of:A. reacting a Grignard reagent with silylated cyanohydrin,B. treating the reaction product of step A with aqueous acid, andC. recovering the resulting acyloin.Acyloins thus formed are useful as photoinitiators for initiation of free radical polymerization reactions.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: June 18, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
  • Patent number: 4510329
    Abstract: A process for preparing cyclopentenolones of the formula ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl or alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## in which R.sub.2 is a hydrogen atom, a methyl group or a halogen atom directly from the corresponding furan-carbinols of the formula: ##STR3## wherein R.sub.1 is as defined above in a single step with an excellent yield, characterized in that the furan-carbinols are treated with water in the presence or absence of a catalyst.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: April 9, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Hiroshi Yamachika
  • Patent number: 4508924
    Abstract: o-Acylphenols and p-acylphenols are prepared by reacting phenol with an acid halide and aluminum chloride, using a halobenzene as the solvent, at from 15.degree. to 55.degree. C. and then at from 55.degree. and 200.degree. C.The compounds obtainable by the process of the invention are valuable starting materials for the preparation of drugs, pesticides and dyes.
    Type: Grant
    Filed: November 1, 1983
    Date of Patent: April 2, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Josef Mueller, Walter-Wielant Wiersdorff, Werner Kirschenlohr, Gerd Schwantje
  • Patent number: 4496767
    Abstract: A novel process for preparing 2-cyclopentenones of the formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkenyl and R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, which comprises esterifying a mixture of a 3-hydroxy-4-cyclopentenone of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each as defined above and a 4-hydroxy-2-cyclopentenone of the formulas: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above with an aliphatic carboxylic acid to give a mixture of the 4-hydroxy-2-cyclopentenone (III) and the cyclopentenone ester of the formula: ##STR4## wherein R.sub.1 and R.sub.2 are each as defined above and R is hydrogen or C.sub.1 -C.sub.4 alkyl and subjecting the resulting mixture to reduction.
    Type: Grant
    Filed: October 18, 1983
    Date of Patent: January 29, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Tadashi Katsura
  • Patent number: 4495370
    Abstract: A process for the preparation of a 5-aryloxy-1-chloro-3,3-dimethyl-2-pentanone of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is halogen, alkyl having 1 to 4 carbon atoms, alkoxy or alkylthio each having 1 to 2 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio each having 1 to 2 carbon atoms and 1 to 5 halogen atoms, cyclohexyl, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, nitro, cyano, alkoxy-carbonyl having 1 to 4 carbon atoms in the alkyl moiety, phenyl or halophenyl, m and n each independently is an integer from 0 to 5, and m+n.ltoreq.5,comprising reacting 1,1,5-trichloro-3,3-dimethyl-1-pentene of the formula ##STR2## with a phenol of the formula ##STR3## in the presence of a base in a diluent, to produce a compound of the formula ##STR4## and subjecting such reaction product to acid hydrolysis.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: January 22, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
  • Patent number: 4480133
    Abstract: Novel 2,4-dihydrocarbylspiro[5.5]undeca-1,4,8-trien-3-one compounds are prepared by reacting an N,N-dihydrocarbyl,2,6-dihydrocarbyl-4-aminomethylphenol with a conjugated diene and an alkyl halide in a liquid solvent medium.
    Type: Grant
    Filed: March 4, 1983
    Date of Patent: October 30, 1984
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper