Reactant Contains -coo- Group Patents (Class 568/319)
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Patent number: 4967011Abstract: 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: GrantFiled: August 11, 1989Date of Patent: October 30, 1990Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Nobuyuki Tokura, Tadayoshi Takefumi, Shunichi Matsumoto, Tatsuhiko Yanagawa, Yoshihiro Shiokawa, Ichiyo Ohtsuka
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Patent number: 4960943Abstract: 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: GrantFiled: March 2, 1989Date of Patent: October 2, 1990Assignee: Bayer AktiengesellschaftInventors: Artur Botta, Hans-Josef Buysch, Lothar Puppe, Dieter Arlt
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Patent number: 4950763Abstract: Ketones of the general formula (I) ##STR1## where R.sup.1 and R.sup.2 independently of one another are each alkyl, cycyloalkyl, arylalkyl, aryl or hetaryl, and one or more of the radicals R.sup.1 and R.sup.2 carry one or more hydrogen atoms on the .alpha.-carbon atom, are prepared by reacting two carboxylic acids of the general formulae (IIa/IIb), R.sup.1 --COOH (IIa) and R.sup.2 --COOH (IIb) or by reacting a carboxylic acid R.sup.1 --COOH (IIa) and a ketone ##STR2## or by reacting a mixture of IIa, IIb and Ib, in the gas phase in the presence of a catalyst, by a process in which a catalyst is used whose active material contains at least 50% by weight of titanium dioxide having a specific surface area greater than 10 m.sup.2 /g.0.Type: GrantFiled: July 18, 1989Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Charles Schommer, Klaus Ebel, Toni Dockner, Matthias Irgang, Wolfgang Hoelderich, Harald Rust
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Patent number: 4929761Abstract: There is disclosed a process for the preparation of a benzophenone, which process comprises contacting a feed comprising an aromatic carboxylic acid in the vapor phase and under suitable conditions with a catalyst which is capable of catalyzing the conversion of an aromatic carboxylic acid to a benzophenone to provide a yield of at least 10% benzophenone and which comprises at least one oxide that is an oxide of an element having an atomic number of at least 60. Typical catalysts are neodymium trioxide and a mixture of thorium dioxide and magnesium oxide.Type: GrantFiled: December 22, 1986Date of Patent: May 29, 1990Assignee: Amoco CorporationInventors: Gregory P. Hussmann, Carl A. Udovich
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Patent number: 4898983Abstract: 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: GrantFiled: November 7, 1988Date of Patent: February 6, 1990Assignee: Raychem LimitedInventor: Ian D. H. Towle
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Patent number: 4895984Abstract: Aromatics are acylated by the Friedel-Crafts method by carrying out the acylation in the presence of metalalkyls or metalalkyl halides of metals or semimetals of main groups two to five and/or of metals of subgroups two or four of the Periodic Table.Type: GrantFiled: May 25, 1988Date of Patent: January 23, 1990Assignee: BASF AktiengesellschaftInventors: Manfred Eggersdorfer, Hardo Siegel, Alfred Schuhmacher, Walter Grosch, Jochem Henkelmann
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Patent number: 4894482Abstract: A process is provided for removing water from a mixture of hydrogen fluoride (HF), a carboxylic acid, e.g., acetic acid, and water by extractive distillation in the presence of a Lewis base as solvent, which does not azeotrope with water, forms bonds with the HF and carboxylic acid which can be broken by heat and has a boiling point at atmospheric pressure at least about 20.degree. C. above that of the carboxylic acid, e.g., N-methyl-2-pyrrolidone, and taking off an overhead vapor comprising a major proportion of the water in said mixture. The extractive distillation may be advantageously integrated in an overall process with the production of an aromatic ketone, e.g., 4-hydroxyacetophone, by the Friedel-Crafts acylation of an aromatic compound, e.g., phenol, with the carboxylic acid, using HF as catalyst, to produce a product mixture comprising the aromatic ketone, HF, carboxylic acid and water, and the removal of aromatic ketone from the product mixture by means of a solvent assisted distillation.Type: GrantFiled: December 6, 1988Date of Patent: January 16, 1990Assignee: Hoechst Celanese CorporationInventors: Daniel D. Lindley, Carl D. Murphy
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Patent number: 4873363Abstract: A new process for the preparation of a 3-(4'-bromobiphenyl-4-yl)tetralin-1-one known as a key intermediate for the production of rodenticides and clinical medicines is provided. The title compound is prepared from P-bromobiphenylbenzylketone in three steps, wherein one of key inventions is dehydroxylation of 3-(4'-bromobiphenyl)-3-hydroxy-4-phenylbutyric acid ethyl ester using trialkylsilane in trifluoroacetic acid. This new process offers a high yield with a facile way and is more suitable for a commercial production than the prior art methods.Type: GrantFiled: May 11, 1988Date of Patent: October 10, 1989Assignee: Korea Advanced Institute of Science and TechnologyInventors: In O. Kim, Sang G. Lee
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Patent number: 4868338Abstract: 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: GrantFiled: March 8, 1988Date of Patent: September 19, 1989Assignee: Blaschim S.p.A.Inventors: Ambrogio Magni, Giuseppina Visentin
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Patent number: 4855460Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.Type: GrantFiled: July 11, 1988Date of Patent: August 8, 1989Assignee: Rhone-Poulenc ChimieInventors: Marc Tordeux, Claude Wakselman, Catherine Francese
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Patent number: 4853481Abstract: Alkyl-substituted aromatic ketones are prepared by reacting alkylbenzenes with carboxylic anhydrides in the presence of a Friedel-Crafts catalyst by performing the reaction in the presence of a tertiary amine or diamine.Type: GrantFiled: November 30, 1987Date of Patent: August 1, 1989Assignee: BASF AktiengesellschaftInventors: Jochem Henkelmann, Manfred Eggersdorfer, Walter Grosch, Alfred Schuhmacher, Hardo Siegel
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Patent number: 4843179Abstract: 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: GrantFiled: January 5, 1988Date of Patent: June 27, 1989Assignee: Raychem CorporationInventors: Viktors Jansons, Heinrich C. Gors
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Patent number: 4835318Abstract: 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: GrantFiled: July 28, 1988Date of Patent: May 30, 1989Assignee: Hoechst AktiengesellschaftInventors: Alfred Kruse, Gunter Siegemund, Klaus Schlich, Ingo Ruppert, deceased
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Patent number: 4827044Abstract: Process of preparation of ketones by the reaction of an organo-metallic compound with a compound carrying a carbonyl, within a solvent, in the presence of a manganous salt as catalyst. The manganous salt is in the form of a double salt of Mn and an alkali metal cation.Type: GrantFiled: March 8, 1988Date of Patent: May 2, 1989Assignee: Societe Nationale Elf AquitaineInventors: Pierre Tozzolino, Gerard Cahiez
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Patent number: 4822919Abstract: There is described a process for producing fungicidally active 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, andn is 0, 1 or 2, which process comprises reacting a 3-trifluoromethyl-4-phenylpyrrole of the formula II ##STR2## wherein R.sub.n is as defined under the formula I, and R.sub.1 is hydrogen or an acyl group, at elevated temperature and elevated pressure, with ammonia. Important intermediates and the production thereof are also described.Type: GrantFiled: August 26, 1987Date of Patent: April 18, 1989Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Robert W. Lang
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Patent number: 4803298Abstract: A process for the preparation of a perfluoroalkyl ketone. A perfluoroalkyl halide, zinc and an ester are brought into contact with one another. Preferably a polar aprotic solvent and/or a pyridine is also present.Type: GrantFiled: July 15, 1987Date of Patent: February 7, 1989Assignee: Rhone-Poulenc ChimieInventors: Catherine Francese, Marc Tordeux, Claude Wakselman
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Patent number: 4777299Abstract: 1,3-Dialkylbenzenes are acylated and deprotected in a mixture of acetic or propionic acid and hydrobromic acid. The dihydroxyphenones thus produced are intermediates in the synthesis of leukotriene antagonists.Type: GrantFiled: January 11, 1988Date of Patent: October 11, 1988Assignee: Eli Lilly and CompanyInventors: Winston S. Marshall, Sandra K. Sigmund, Celia A. Whitesitt
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Patent number: 4777300Abstract: An aromatic ketone having the formula XArCOPhPhOH is made by contacting an ester of formula XArCOOPhPh, whereAr is a divalent mono- or poly - aromatic group which may optionally be substituted;Ph is para-phenylene; andX is hydrogen or halogen or a nitro-, alkylsulphonyl-, arylsulphonyl-, alkylcarbonyl- or hydrocarbon groupwith a Friedel Crafts catalyst comprising one or more Lewis acids in an amount of at least 2.2 moles of such catalyst for each mole of the ester.Type: GrantFiled: January 30, 1987Date of Patent: October 11, 1988Assignee: Imperial Chemical Industries PLCInventors: Howard M. Colquhoun, James A. Daniels, David F. Lewis
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Patent number: 4777298Abstract: Resorcinol is acylated in a mixture of acetic or propionic acid and hydrobromic acid. The dihydroxy acylbenzenes thus produced are intermediates in the synthesis of leukotriene antagonists.Type: GrantFiled: January 11, 1988Date of Patent: October 11, 1988Assignee: Eli Lilly and CompanyInventors: Winston S. Marshall, Sandra K. Sigmund, Celia A. Whitesitt
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Patent number: 4764641Abstract: A process is described for preparing optically active alpha-halogenated carbonyl compounds.This process consists of transforming the carbonyl compound into the corresponding acetal with tartaric acid or a derivative thereof, halogenating this acetal and releasing the carbonyl compound.Type: GrantFiled: October 6, 1986Date of Patent: August 16, 1988Assignee: Zambon SpAInventors: Graziano Castaldi, Silvia Cavicchioli, Claudio Giordano, Carlo Restelli
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Patent number: 4764642Abstract: 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: GrantFiled: October 6, 1986Date of Patent: August 16, 1988Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Silvia Cavicchioli, Claudio Giordano
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Patent number: 4754074Abstract: There is disclosed a method for the preparation of a dialkyl ketone from an aliphatic carboxylic acid in the presence of a catalyst comprising manganese dioxide on a support of catalytically active alumina. This method is a convenient way of making diethyl ketone from propionic acid.Type: GrantFiled: December 22, 1986Date of Patent: June 28, 1988Assignee: Amoco CorporationInventor: Gregory P. Hussmann
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Patent number: 4714781Abstract: The production of a 4-lower alkyl or 4-phenyl ring-substituted phenyl lower alkyl ketone, e.g. 4-methylacetophenone, 4-ethylacetophenone or 4-phenylacetophenone, is carried out by reacting a lower alkyl- or phenyl-substituted benzene, e.g. toluene, ethylbenzene, or biphenyl, with a lower alkanoic acid, e.g. acetic acid, at an elevated temperature in the presence of a medium pore, pentasil-type molecular sieve, e.g. an H-ZSM-5 zeolite, a silicalite or an AMS-1B borosilicate, as catalyst.Type: GrantFiled: March 27, 1986Date of Patent: December 22, 1987Assignee: Hoechst Celanese CorporationInventor: Balaram B. G. Gupta
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Patent number: 4705801Abstract: There is described a process for producing fungicidally active 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, and n is 0, 1 or 2, which process comprises reacting a 3-trifluoromethyl-4-phenylpyrrole of the formula II ##STR2## wherein R.sub.n is as defined under the formula I, and R.sub.1 is hydrogen or an acyl group, at elevated temperature and elevated pressure, with ammonia. Important intermediates and the production thereof are also described.Type: GrantFiled: October 7, 1985Date of Patent: November 10, 1987Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Robert W. Lang
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Patent number: 4675449Abstract: A process is provided for the production of 6-hydroxy-2-naphthones, e.g., 6-hydroxy-2-acetonaphthone, by contacting a 2-naphthyl carboxylate ester, e.g., 2-naphthyl acetate with at least 20 moles of hydrogen fluoride per mole of 2-naphthyl ester, at reaction temperatures, e.g., 0.degree. to 100.degree. C. for a period of reaction, e.g., 30 minutes to 8 hours sufficient to produce the desired amount of 6-hydroxy-2-naphthone. The process may utilize a carboxylic acid or anhydride, e.g., acetic acid or anhydride as an additive for the purpose of further increasing the regioselectivity of the 6-hydroxy-2-naphthone product. The process is capable of being carried out at a conversion of 2-naphthyl ester of at least 90% and a regioselectivity to 6-hydroxy-2-naphthone of at least 90 mol %.Type: GrantFiled: June 3, 1986Date of Patent: June 23, 1987Assignee: Celanese CorporationInventor: Kenneth G. Davenport
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Patent number: 4670603Abstract: 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: GrantFiled: September 24, 1985Date of Patent: June 2, 1987Assignee: Blaschim S.p.A.Inventors: Oreste Piccolo, Giuseppina Visentin, Pietro Blasina, Franca Spreafico
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Patent number: 4668826Abstract: The production of 2-hydroxyphenyl lower alkyl ketones, e.g. 2-hydroxyacetophenone, by reaction of phenol and a lower alkanoic acid, e.g. acetic acid, is carried out by contacting the phenol and acid at an elevated temperature with a ZSM-5 zeolite catalyst having the formula:0.9.+-.0.2M.sub.2/n O:w.sub.2 O.sub.3 :5-100yO.sub.2 :zH.sub.2 Owherein M is a cation, n is the valence of said cation, w is selected from the group consisting of aluminum and gallium, Y is selected from the group consisting of silicon and germanium, and z is from 0 to 40, and in which at least about 80% of the cations are replaced with hydrogen ions. Preferably the catalyst has the formula:0.9.+-.0.2M.sub.2/n O:Al.sub.2 O.sub.3 :5-100SiO.sub.2 :zH.sub.2 Oand M is selected from the group consisting of alkali metal cations and tetraalkylammonium cations, the alkyl groups of which preferably contain 2-5 carbon atoms.Type: GrantFiled: December 2, 1985Date of Patent: May 26, 1987Assignee: Celanese CorporationInventor: Balaram B. G. Gupta
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Patent number: 4665246Abstract: 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: GrantFiled: March 9, 1984Date of Patent: May 12, 1987Assignee: Chem Biochem Research, Inc.Inventor: Chris Anderson
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Patent number: 4663485Abstract: A process is provided for the distillation of a composition containing 4-hydroxyacetophenone and hydrogen fluoride in the presence of an alkane assisting solvent having from 4 to 16 carbon atoms e.g. n-hexane or n-octane. The process is carried out to obtain an overhead vapor containing alkane solvent and most of the hydrogen fluoride in the feed, and a liquid residue containing most of the 4-hydroxyacetophenone in the feed. The overhead vapor is condensed to form two immiscible phases, one containing a preponderance of hydrogen fluoride and the other a preponderance of alkane solvent, with the latter phase being returned to the distillation as reflux. The liquid residue also separates into two immiscible layers, one containing most of the 4-hydroxyacetophenone in the feed which is recovered and the other a preponderance of alkane solvent.Type: GrantFiled: July 22, 1986Date of Patent: May 5, 1987Assignee: Celanese CorporationInventors: Carl D. Murphy, Donna L. Keene, Daniel D. Lindley
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Patent number: 4652683Abstract: A process is provided for the production of 2-hydroxyphenyl lower alkyl ketones, e.g. 2-hydroxyacetophenone, by reacting phenol and a lower alkanoic acid, e.g. acetic acid or an ester of phenol and a lower alkanoic acid, e.g. phenyl acetate, in the presence of a silicalite catalyst containing about 700 to 14000 ppm of alumina, which has been calcined at least once from the as synthesized form. The reaction is preferably conducted in the vapor phase in the presence of an inert gas such as nitrogen.Type: GrantFiled: December 2, 1985Date of Patent: March 24, 1987Assignee: Celanese CorporationInventors: Ioan Nicolau, Adolfo Aguilo
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Patent number: 4650873Abstract: Processes for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide.Type: GrantFiled: May 1, 1986Date of Patent: March 17, 1987Assignee: Riker LaboratoriesInventor: Charles M. Leir
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Patent number: 4622066Abstract: A fluorine-containing benzophenone derivative of the formula: ##STR1## wherein R.sup.1 is a group of the formula: --OM (in which M is hydrogen or alkali metal), lower alkoxy, lower acyloxy, a group of the formula: ##STR2## (in which R.sup.3 and R.sup.4 are same or different and hydrogen or lower alkyl) or a group of the formula: --OCH.sub.2 COOR.sup.5 (in which R.sup.5 is hydrogen, lower alkyl or alkali metal); R.sup.2 is halogen, nitro, chlorosulfonyl, sulfo, trifluoromethyl or a group of the formula: --SCF.sub.2 H; and m and n are each an integer of 1 to 4 provided that the sum of m and n is not more than 5 having selective herbicidal activities on grasses and crops.Type: GrantFiled: January 10, 1984Date of Patent: November 11, 1986Assignee: Daikin Kogyo Co., Ltd.Inventors: Katsuhiko Kitahara, Tetsuya Masutani, Takashi Yamaoka, Tetsuo Kitahaba, Takasi Nisioka, Yasuo Itami
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Patent number: 4607125Abstract: A process of acylating a monocyclic phenolic reactant, e.g. phenol to a hydroxy aromatic ketone, e.g. 4-hydroxyacetophenone, by contacting the phenolic reactant with about 0.4 to 0.8 moles of a carboxylic acid anhydride, e.g. acetic anhydride as acylating agent per mole of phenolic reactant of in the presence of a Friedel-Crafts catalyst, e.g. hydrogen fluoride. The process generally results in phenolic reactant conversions of at least about 80% and reaction selectivities to hydroxy aromatic ketone of at least about 70%.Type: GrantFiled: April 8, 1985Date of Patent: August 19, 1986Assignee: Celanese CorporationInventor: Graham N. Mott
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Patent number: 4605758Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 4604485Abstract: 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: GrantFiled: June 4, 1984Date of Patent: August 5, 1986Assignee: Imperial Chemical Industries PLCInventor: Howard M. Colquhoun
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Patent number: 4599452Abstract: 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: GrantFiled: June 4, 1984Date of Patent: July 8, 1986Assignee: Imperial Chemical Industries PLCInventors: Howard M. Colquhoun, Alan G. Breeze
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Patent number: 4593125Abstract: 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: GrantFiled: March 13, 1985Date of Patent: June 3, 1986Assignee: Celanese CorporationInventors: Kenneth G. Davenport, H. Clay Linstid, III
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Patent number: 4576752Abstract: .beta.-Substituted polyfluoroethyl compounds, process for the preparation thereof, copolymers thereof, compound intermediates, and process therefor. The copolymers are useful as ion exchange resins or structural foams.Type: GrantFiled: July 19, 1982Date of Patent: March 18, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4569945Abstract: The invention is dealing with arylindane-1,3-diones of the formula: ##STR1## which can be used in the treatment of inflammatories, psoriasis and asthma.Type: GrantFiled: October 12, 1984Date of Patent: February 11, 1986Assignee: Akzo N.V.Inventors: Alexander C. Campbell, Donald F. M. Stevenson
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Patent number: 4568478Abstract: There is disclosed a solution of at least one fluoroxy compound, wherein said solution has a fluoroxy compound concentration of at least 0.5 meq/liter; said concentration containing about 35 to 100% of an acyl hypofluorite, based on the total number of equivalents of fluoroxy compounds present. The acyl hypofluorite has the formula X(CF.sub.2).sub.n COOF wherein X is H or F and n is 5 to 16. The solution is prepared by treating a suspension of a corresponding specified alkali salt with excess F.sub.2, and is useful as a selective fluorinating agent.Type: GrantFiled: April 18, 1984Date of Patent: February 4, 1986Assignee: E. I. Dupont de Nemours and CompanyInventors: William J. Middleton, Shlomo Rozen
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Patent number: 4560787Abstract: The present invention relates to a method of preparing 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-one or substitution products thereof from dibenzyl-o-carboxylic acid or its corresponding substitution products, by cyclocondensation. The cyclocondensation is performed in either of two ways, namely (a) with catalytic amounts of a concentrated acid as catalyst, or (b) with the aid of di- and/or trichloromethyl aromatic compounds in the presence of catalysts, preferably catalysts from the group of the Lewis acids.Type: GrantFiled: July 19, 1984Date of Patent: December 24, 1985Assignee: Dynamit Nobel AGInventors: Gunter Zoche, Wilhelm Vogt
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Patent number: 4559177Abstract: A compound of the formula: ##STR1## wherein m is an integer of 11 to 22; R.sub.1 is alkyl having 1 to 4 carbon atoms; R.sub.2 is hydrogen, alkyl having 1 to 4 carbon atoms or carboxylic acyl having 1 to 8 carbon atoms. Such compounds have pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory and lysosomal membrane stabilizing activity, and inhibit SRS-A production, and are useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.Type: GrantFiled: June 30, 1980Date of Patent: December 17, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Tetsuya Okutani, Giichi Goto
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Patent number: 4495104Abstract: A compound of the general formula ##STR1## wherein n is an integer of 10 to 21, inclusive; R is H or lower alkyl having 1 to 4 carbon atoms has pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory, lysosomal membrane stabilizing and SRS-A production inhibitory activities and is useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.Type: GrantFiled: July 11, 1980Date of Patent: January 22, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Isuke Imada, Tetsuya Okutani, Masazumi Watanabe
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Patent number: 4474990Abstract: Substantially pure p-phenoxybenzoyl compounds are prepared by reacting diphenyl ether and an appropriate acyl compound in the presence of hydrogen fluoride. The resulting p-phenoxyaryl alkyl ketone can be converted into p-phenoxybenzoic acid or salts thereof, p-phenoxybenzoyl halide or lower alkyl p-phenoxybenzoate for use preparing homo- and copolymers containing a p-phenoxybenzoyl repeating unit.Type: GrantFiled: November 24, 1982Date of Patent: October 2, 1984Assignee: Raychem CorporationInventor: Viktors Jansons
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Patent number: 4469883Abstract: Acetoxyacetophenone is the predominant product when phenyl acetate, acetic acid and acetic anhydride are reacted in the presence of palladium and a gas mixture containing an inert gas and more than 13 vol. % oxygen. Secondary products are hydroxyacetophenone and phenylene diacetates. The meta isomers predominate when a metal acetate is present in the reaction mixture. Mineral acids cause shift to ortho isomers.Type: GrantFiled: May 11, 1981Date of Patent: September 4, 1984Assignee: Sun Tech, Inc.Inventors: Chao-Yang Hsu, James E. Lyons
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Patent number: 4454350Abstract: A process for the acylation of halo- or trihalomethylbenzenes, wherein a halo- or trihalomethylbenzene is reacted with a carboxylic acid, a precursor or a derivative thereof in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: June 12, 1984Assignee: Rhone-Poulenc Specialities ChimiquesInventor: Michel Desbois
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Patent number: 4453010Abstract: Production of a hydroxy arylophenone by reacting an aromatic carboxylic acid Ar(--CO.sub.2 H).sub.p where Ar is an aromatic radical, (--CO.sub.2 H) is an aromatic carboxylic acid group, and p is 1 or 2 with an aromatic compound H--Ar'--OH where Ar' is an aromatic radical and --H and --OH are aromatically bound para to each other in a benzenoid ring, in the presence of an alkyl sulphonic acid, particularly methane sulphonic acid, to produce a hydroxy arylophenone of formula Ar(--CO--Ar'--OH).sub.p where the carbonyl and hydroxyl groups are para to each other in the hydroxyl-containing benzenoid ring of Ar'. The production of the hydroxy arylophenone proceeds through the intermediate ester (H--Ar'--O--CO--).sub.p Ar and the production of the hydroxy arylophenone starting from the ester is also claimed.Type: GrantFiled: January 20, 1982Date of Patent: June 5, 1984Assignee: Imperial Chemical Industries PLCInventor: Philip A. Staniland
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Patent number: 4453012Abstract: A process for the preparation of phenyl ketones, characterized in that, in a first stage, a halo- or trihalomethylbenzene is reacted with a trihalomethylated aliphatic or aromatic compound in the presence of boron trifluoride in an amount such that the absolute pressure of boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent, and in that, in a second stage, the resultant product is hydrolyzed. The products are used as intermediates in the synthesis of compounds having a pharmaceutical or phytosanitary (e.g., herbicidal) activity.Type: GrantFiled: June 28, 1982Date of Patent: June 5, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4446078Abstract: A process for the preparation of .alpha.,.alpha.-difluoroalkoxy or .alpha.,.alpha.-difluoroalkylthiophenyl ketones, in which a polyhaloalkoxybenzene or a polyhaloalkylthiobenzene is reacted with a carboxylic acid, a precursor or a derivative of this acid in the presence of boron trifluoride in such an amount that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: May 1, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4438043Abstract: A process for the preparation of di- or trifluoromethoxyphenyl ketones or di- or trifluoromethylthiophenyl ketones, characterized in that, in a first stage, a di- or trihalomethoxybenzene or a di- or trihalomethylthiobenzene is reacted with a trihalomethylated aromatic or aliphatic compound in the presence of boron trifluoride in an amount such that the absolute pressure of boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent and in that, in a second stage, the product of the first stage is hydrolyzed. The resultant products are useful as intermediates in the synthesis of compounds having a pharmaceutical or phytosanitary (e.g., herbicidal) activity.Type: GrantFiled: June 28, 1982Date of Patent: March 20, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois