Containing Alicyclic Ring Having At Least Seven Members Patents (Class 568/821)
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Patent number: 5516929Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallochloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.Type: GrantFiled: February 12, 1993Date of Patent: May 14, 1996Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
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Patent number: 5489716Abstract: The invention provides novel methods for the oxidation of hydrocarbons with oxygen-containing gas to form hydroxy-group containing compounds and for the decomposition of hydroperoxides to form hydroxygroup containing compounds. The catalysts used in the methods of the invention comprise transition metal complexes of a porphyrin ring having 1 to 12 halogen substituents on the porphyrin ring, at least one of said halogens being in a meso position and/or the catalyst containing no aryl group in a meso position. The catalyst compositions are prepared by halogenating a transition metal complex of a porphyrin.Type: GrantFiled: September 7, 1994Date of Patent: February 6, 1996Assignee: Sun Company, Inc. (R&M)Inventors: Paul E. Ellis, Jr., James E. Lyons
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Patent number: 5475158Abstract: A process for the preparation of cycloalkanols by the hydrolysis of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters, which comprises the following steps:a) reaction of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters with water at a temperature of from 30.degree. to 250.degree. in the liquid phase yielding a reaction mixture consisting of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters, cycloalkanol, C.sub.1 -C.sub.4 fatty acids, and water.b) separation of the reaction mixture obtained in stage a) at a temperature of from 0.degree. to 200.degree. C. into a top phase consisting substantially of cycloalkanol and cycloalkyl C.sub.1 -C.sub.4 fatty acid esters and a bottom phase consisting substantially of water and C.sub.1 -C.sub.4 fatty acids.c) separation of cycloalkanol from the top phase obtained in stage b) by distillation and recycling unconverted cycloalkyl C.sub.1 -C.sub.4 fatty acid esters to stage a).Type: GrantFiled: December 1, 1993Date of Patent: December 12, 1995Assignee: BASF AktiengesellschaftInventors: Thomas Krug, Rolf Fischer, Rolf Pinkos
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Patent number: 5426246Abstract: Disclosed are a catalyst for directly reducing a carboxylic acid, the catalyst comprising a tin compound and a ruthenium compound supported on a carrier, the catalyst being prepared by the steps of calcining the tin compound in the presence of oxygen after deposition of the tin compound alone on the carrier, and activating the obtained product after deposition of the ruthenium compound on said carrier, a process for preparing the catalyst, and a process for preparing an alcohol compound using the catalyst.Type: GrantFiled: July 26, 1994Date of Patent: June 20, 1995Assignee: Arakawa Chemical Industries, Ltd.Inventors: Eiji Nagahara, Yasushi Itoi
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Patent number: 5405948Abstract: A compound of formula (I): selected from 1,5-diyne-3-cyclodecene and undecene compounds. ##STR1## in which: R represents a hydrogen atom, a straight-chain or branched (C.sub.1 -C.sub.6) acyl radical or a glycoside radical,R' represents a hydrogen atom ##STR2## n is 1 or 2, and R.sub.1 and R.sub.2 simultaneously represent two hydrogen atoms or, together with the two carbon atoms and the double bond to which they are attached, form a phenyl ring.Type: GrantFiled: September 30, 1992Date of Patent: April 11, 1995Assignee: Adir et CompagnieInventors: Jean-Marie Beau, Christophe Crevisy, Ghanem Atassi, Alain Pierre
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Patent number: 5406001Abstract: The present invention relates to a method for the continuous preparation of a mixture of a cycloalkanone, a cycloalkanol and a cycloalkylhydroperoxide. In the method, a cycloalkane, corresponding to the cycloalkenone, cycloalkenol and cycloalkylhydroperoxide, is oxidized in a continuous process, with the aid of an oxygen-containing gas, in the absence of a metal catalyst, at a temperature of between 130.degree. C. and 200.degree. C. The oxidation is at least partly carried out in the presence of between 0.002 and 2 mmol of a phenolic compound per kg of reaction mixture (mmol/kg).Type: GrantFiled: December 15, 1993Date of Patent: April 11, 1995Assignee: DSM N.V.Inventors: Johannes G. H. M. Housmans, Ubaldus F. Kragten
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Patent number: 5406007Abstract: Disclosed is a process for the conversion of conjugated epoxyalkenes to unsaturated alcohols wherein a conjugated epoxyalkene is catalytically hydrogenated in the presence of a sulfur-modified or sulfided nickel catalyst whereby the epoxide ring is hydrogenolyzed without concomitant hydrogenation of the olefinic unsaturation thereby producing allylic and/or homoallylic alcohols.Type: GrantFiled: July 15, 1994Date of Patent: April 11, 1995Assignee: Eastman Chemical CompanyInventor: Stephen N. Falling
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Patent number: 5399587Abstract: The present invention relates to novel potassium channel agonists which are useful in activating the calcium activated Maxi-K potassium channel in mammalian neuronal and smooth muscle tissue. The claimed compounds are of the general formula: ##STR1## In addition, a novel microbiological process for producing the claimed compounds is described.Type: GrantFiled: December 13, 1993Date of Patent: March 21, 1995Assignee: Merck & Co., Inc.Inventors: Maria L. Garcia, Robert A. Giacobbe, Otto D. Hensens, Gregory J. Kaczorowski, Seok H. Lee, Owen B. McManus, Deborah L. Zink
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Patent number: 5349112Abstract: Novel cyclic anti-tumor promoter compounds and therapeutic compositions are disclosed, along with method for their production and use as anti-cancer and cancer-prevention agents.Type: GrantFiled: November 26, 1993Date of Patent: September 20, 1994Assignee: University of HawaiiInventor: Marcus A. Tius
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Patent number: 5344946Abstract: The present invention provides a process for the preparation of vicinal diols and/or epoxides by the oxidation of olefinically-unsaturated compounds with the use of an inorganic heptavalent rhenium compound as catalyst and of hydrogen peroxide as oxidation agent, wherein the reaction is carried out in a solvent selected from the group consisting of organic phosphoric acid esters and ethers with a boiling point above 50.degree. C. under atmospheric conditions.Type: GrantFiled: May 20, 1993Date of Patent: September 6, 1994Assignee: Solvay Interox GmbHInventors: Siegfried Warwel, Mark R. Klaas, Michael Sojka
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Patent number: 5292971Abstract: Fluorine-substituted vicinal glycols of the formula ##STR1## in which the substituents R.sub.1 to R.sub.4, independently of one another, have the following meanings: R.sub.1 to R.sub.4 =H, fluorine, C.sub.1 - to C.sub.18 -alkyl in which some or all of the hydrogens may be substituted by fluorine, and at least one of the substituents R.sub.1 to R.sub.4 is a completely fluorinated alkyl or an alkyl of the formula--(CH.sub.2).sub.m --(C.sub.n F.sub.2n+1),in which m is 1 or 2, and n is an integer from 1 to 17, and x is 0 or 1.Furthermore, a method for the preparation of the fluorinated vicinal glycols is described. If the fluorinated vicinal glycols are condensed together with dicarboxylic acids, products having enhanced thermal stability are obtained.Type: GrantFiled: February 12, 1993Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Jurgen Kulpe, Heinz Strutz
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Patent number: 5276217Abstract: Novel cyclic anti-tumor promoter compounds and therapeutic compositions are disclosed, along with method for their production and use as anti-cancer and cancer-prevention agents.Type: GrantFiled: March 19, 1992Date of Patent: January 4, 1994Assignee: University of HawaiiInventor: Marcus A. Tius
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Patent number: 5262571Abstract: A process of synthesizing enantiomerically pure compounds defined by Formula V, ##STR1## which are useful as chiral auxiliaries is disclosed. The process comprises, first, combining a base of Formula Y.sup.- Z.sup.+ (Formula I), wherein Y.sup.- is an organic anion and Z.sup.+ is an inorganic cation, with a compound of Formula II, ##STR2## wherein R.sub.1 is a C.sub.1 -C.sub.4 alkyl group and R.sub.2 is the same as R.sub.1, or wherein R.sub.1 and R.sub.2 together form cyclopentane or cyclohexane, and wherein R.sub.3 is a substituted or unsubstituted aryl group, to form a compound defined by Formula III, ##STR3## then: (b) reacting the compound of Formula III with a cyclic epoxide defined by Formula IV, ##STR4## wherein n is 1, 2, or 3, to form a racemic mixture of a compound defined by Formula V.Type: GrantFiled: March 20, 1992Date of Patent: November 16, 1993Assignee: North Carolina State UniversityInventors: Daniel L. Comins, James M. Salvador
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Patent number: 5235117Abstract: For preparing at least one boric oxide in an anhydrous or hydrated form and of general formula B.sub.2 O.sub.3, xH.sub.2 O, in which x is a number from 0 to 3, a methyl borate hydrolyzate comprising boric oxide and methanol is introduced into a distillation column is introduced the product from, at least one compound (preferably a hydrocarbon such as, e.g., 2,3-dimethyl butane or 2-methyl pentane) forming a heteroazeotrope with methanol, said heteroazaeotrope having a boiling point below that of the azeotrope formed by methyl borate with methanol and at least one compound having a boiling point higher than that of methyl borate, said compound not forming an azeotrope with a boiling point below that of said heteroazeotrope and then at the head of the column said heteroazeotrope is recovered and at the bottom of the column a suspension containing at least one boric oxide.Type: GrantFiled: September 25, 1991Date of Patent: August 10, 1993Assignee: Institut Francais du PetroleInventors: Jacques Alagy, Christian Busson, Lionel Asselineau
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Patent number: 5227543Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant, an osmium-containing compound and an organic soluble anion are combined. The presence of the organic soluble anion allows the asymmetric dihydroxylation reaction to occur rapidly and the amount of olefin that is diydroxylated is high with concomitantly less chiral ligand and osmium-containing catalyst than previously achieved.Type: GrantFiled: October 10, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Wihelm K. Amberg
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Patent number: 5210336Abstract: A process is provided for the conversion of an olefin to the corresponding glycol wherein a mixture of olefin, oxygen, carbon dioxide and water is reacted in a solvent at supercritical conditions with respect to the reaction mixture.Type: GrantFiled: January 24, 1992Date of Patent: May 11, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Anne M. Gaffney, John A. Sofranko
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Patent number: 5183942Abstract: Macrocyclic enediynediols and enediynediones having a ten carbon ring and open chain enediyne dihydroperoxides having eight carbons between the hydroperoxide groups that cleave DNA are disclosed, as are methods of making and using the same.Type: GrantFiled: November 5, 1991Date of Patent: February 2, 1993Assignee: The Scripps Research InstituteInventors: Kyriacos C. Nicolaou, Erik Sorensen, Chan-Kou Hwang, Robert Discordia, Robert G. Bergman, Robert E. Minto
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Patent number: 5166373Abstract: The present invention provides novel acyclic terpenes of the formula: ##STR1## which are useful as intermediates for the industrially advantageous production of sarcophytol A.Type: GrantFiled: December 30, 1991Date of Patent: November 24, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5149889Abstract: A process is disclosed for the preparation of tertiary alcohols, alpha-alkyl substituted nitriles, alkyl-substituted imines or tertiary amines by alkylation of a starting material that is a carbonyl compound or a nitrile followed by hydrolysis wherein the alkylation is carried out with the aid of a reaction system formed by suspending a mixture of:substantially 15 to 25% by weight of methyllithium or ethyllithium;substantially 35 to 45% by weight of an inorganic compound selected from the group which consists of at least one metal oxide selected from the group which consists of SiO.sub.2, Al.sub.2 O.sub.3, and CaO, and synthetic anhydrous aluminum silicate; andsubstantially 35 to 45% by weight of a paraffin oil or wax; in an organic solvent selected from the group which consists of:C.sub.5 to C.sub.10 saturated aliphatic hydrocarbons, C.sub.5 to C.sub.Type: GrantFiled: October 30, 1990Date of Patent: September 22, 1992Assignee: Metallgesellschaft AktiengesellschaftInventors: Jurgen Deberitz, Wilfried Weiss
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Patent number: 5095155Abstract: Closely boiling diastereomeric isomer alcohols are separated by converting them to esters having disparate boiling points, separating the ester isomers by distillation and saponifying the separate ester isomers to obtain the individual alcohol isomers.Type: GrantFiled: June 7, 1990Date of Patent: March 10, 1992Assignee: Union Camp CorporationInventor: Peter W. D. Mitchell
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Patent number: 5047575Abstract: Compounds, and a process for their preparation, have the formula ##STR1## or corresponding salts thereof wherein R represents a group of the formula ##STR2## wherein R.sub.1 represents oxazolinyl, --C.tbd.N, --CH.sub.2 OR.sub.2 or ##STR3## These compounds in the form of pharmaceutical or cosmetic compositions are useful for the treatment of keratinization disorders.Type: GrantFiled: October 14, 1988Date of Patent: September 10, 1991Assignee: L'OrealInventors: Guy Solladie, Serge Forestier, Gerard Lang
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Patent number: 5004843Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.Type: GrantFiled: May 29, 1990Date of Patent: April 2, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
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Patent number: 4999454Abstract: The invention is directed to a new process for the preparation of carbinols of the general formula I ##STR1## by reaction chloral and olefins of the general formula ##STR2## and by optional acylation of the product comprising dissolving a catalyst of the general formula IIIFe.sub.n (NH.sub.4).sub.x Y.sub.m .multidot.A.sub.p IIIin chloral, then adding the olefin of the general formula II in order to produce a complex of the general formula IV ##STR3## from which a complex of the general formula V ##STR4## is formed, and from the reaction mixture a compound of the general formula I is obtained whereafter(a) the residual complex of the general formula V dissolved in the product is decomposed with an acidic solution and if desired the obtained product is distilled or(b) the product in the reaction mixture is acylated.The compounds prepared according to the invention can be utilized as intermediates when preparing e.g., permethrin and other pyrethroid insecticides.Type: GrantFiled: October 3, 1985Date of Patent: March 12, 1991Assignee: Chinoin Gyogyszer ES Vegyeszeti Termekek Gyara RT.Inventors: Rudolf Soos, Jozsef Nemes, Miklos Szelestei, Istvan Schler, Laszlo Vidra, Istvan Szekely
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Patent number: 4980485Abstract: Optically active periplanone-B is manufactured through oxidizing (1RS, 4S, 5E)-isopropyl-7-methylene-5-cyclodecene-1-ol. The oxidized product is regioselectively enolized and then sulfenylated. The sulfenylated product is oxidized and then subjected to decomposition of the sulfoxide. The decomposed product is epoxidated, and the epoxidated product is converted into an enolate which is then oxidized. The oxidized product is oxidized and then regio- and stereoselectively epoxidated to obtain optically active periplanone-B.Type: GrantFiled: September 26, 1989Date of Patent: December 25, 1990Assignee: Japan Tobacco Inc.Inventors: Kenji Mori, Takeshi Kitahara, Koshi Koseki
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Patent number: 4968848Abstract: A process for the preparation of perfluoroalkyl compounds which comprises reacting a perfluoroalkyl-trimethylsilane of the general formula (CH.sub.3).sub.3 Si-C.sub.n F.sub.2n+1 (I), wherein the group C.sub.n F.sub.2n+1 represents a perfluoroalkyl group having from 1 to 6 carbon atoms, with a carbonyl compound of the general formula F.sup.1 --CO--R.sup.2 (II), wherein R.sup.1 represents a hydrocarbon group or hydrogen and R.sup.2 represents a hydrocarbon group, a perfluoroalkyl group or a perfluoroaryl group, but wherein R.sup.1 and R.sup.2 together may also be part of an alicyclic ring system, in the presence of a salt-like fluoride--which is at least partially soluble in the reaction medium--as a catalyst to yield a silylether of the formula ##STR1## and isolating this compound or hydrolyzing it to yield an alcohol of the formula IV ##STR2## The invention also relates to pentafluoroethyl trimethylsilane (CH.sub.3).sub.3 Si--CF.sub.2 CF.sub.3 and a process for the preparation of this compound.Type: GrantFiled: February 21, 1989Date of Patent: November 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Alfred Kruse, Gunter Siegemund, Axel Schumann
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Patent number: 4948780Abstract: Compounds of the general formulae ##STR1## in which R may be a methyl or ethyl radical and R.sup.1 may be a hydrogen, methyl or ethyl radical are disclosed. Also provided as part of the present invention are processes for the preparation of the above compounds. The compounds of the invention are useful as scents.Type: GrantFiled: January 6, 1988Date of Patent: August 14, 1990Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Walter Hafner, Helmut Gebauer, Erich Markl, Marlies Regiert
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Patent number: 4933508Abstract: A method for producing a cycloalkanol, which comprises oxidizing a cycloalkane with a molecular oxygen-containing gas in a liquid phase in the presence of a catalyst, wherein an aromatic nitro compound is present in the oxidation reaction system.Type: GrantFiled: September 23, 1988Date of Patent: June 12, 1990Assignee: Mitsubishi Kasei CorporationInventors: Haruo Habu, Kouji Watanabe, Takeshi Matsuoka
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4906794Abstract: The present invention provides lysosome liberation inhibitors comprising, as effective ingredients, cembrane-type diterpene compounds represented by the general formula (I) or (II): ##STR1## wherein R is a hydrogen atom or an acyl group. Also provided is histamine release inhibitors comprising the cembrane-type diterpene compounds represented by the general formula (I) or (II) above as effective ingredients.Type: GrantFiled: February 10, 1989Date of Patent: March 6, 1990Assignee: Mitsubishi Kasei CorporationInventors: Kohei Umezu, Koichiro Hirayama, Kazuo Suzuki
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Patent number: 4853368Abstract: The invention relates to new methylcyclododecatri-2,5,9-en-1-oles of formula ##STR1## in which one of the dashed lines represents a double bond and the other a single bond, and the endocyclic double bonds may be cis- and trans-configured,a process for their preparation and their use as scents.Type: GrantFiled: March 22, 1988Date of Patent: August 1, 1989Assignee: Haarmann & Reimer GmbHInventors: Jurgen Neinhaus, Rudolf Hopp, Wilhelm Gottsch, Egon Oelkers
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Patent number: 4849550Abstract: A industrially excellent method for producing a cycloalkanol by the hydration of a cycloalkene having from 4 to 8 carbon atoms with an aromatic sulfonic acid as a catalyst which comprises carrying out said hydration in the presence of a phenol.Type: GrantFiled: March 24, 1988Date of Patent: July 18, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Tamio Shirafuji, Itaru Kawata
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Patent number: 4822925Abstract: Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.Type: GrantFiled: February 6, 1987Date of Patent: April 18, 1989Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4783558Abstract: Flavoring and perfume compositions, flavored foodstuffs and luxury consumables and perfumed products which contain (+)-spathulenol and/or (+)-4a-allospathulenol, having respective structural formula ##STR1## as the base material, (+)-4a-allospathulenol per se and a process for the preparation of these spathulenols.Type: GrantFiled: April 10, 1987Date of Patent: November 8, 1988Assignee: Naarden International N.V.Inventors: Leendert M. van der Linde, Franciscus P. van Lier, Antonius J. A. van der Weerdt
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Patent number: 4755626Abstract: 4-isopropyl-7-methylene-5-cyclodecen-1-ol is disclosed. The compound allows manufacture of optically active periplanone-B on an industrial scale.Type: GrantFiled: August 7, 1987Date of Patent: July 5, 1988Assignee: Japan Tobacco, Inc.Inventors: Masataka Mori, Kenji Mori, Takeshi Kitahara, Koshi Koseki
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Patent number: 4749681Abstract: Described are polyalkyl-substituted oxocycloheptane derivatives defined according to the structure: ##STR1## wherein X represents one of the moieties: ##STR2## wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond; or both dashed lines are carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 represents hydrogen or lower alkyl with the proviso that when the dashed line at the 4-5 position is a double bond, R.sub.2 is hydrogen and when the dashed line at the 3-4 position is a double bond, R.sub.1 is hydrogen; wherein R.sub.4 represents C.sub.1 -C.sub.4 lower alkyl; and wherein Y represents chloro or bromo.Type: GrantFiled: May 22, 1986Date of Patent: June 7, 1988Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Howard H. Heinsohn, Jr.
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Patent number: 4720591Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.Type: GrantFiled: December 12, 1986Date of Patent: January 19, 1988Assignee: BASF AktiengesellschaftInventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
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Patent number: 4701570Abstract: An antitumor agent containing 2,7,11-cembratriene-4,6-diol as an active ingredient, and a process for treatment of tumors with the antitumor agent, are disclosed.Type: GrantFiled: July 2, 1986Date of Patent: October 20, 1987Assignee: Japan Tobacco Inc.Inventors: Shigenobu Mizusaki, Daisuke Yoshida, Yutaka Saito
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Patent number: 4693845Abstract: Novel bornane-3-spiro-1'-cylopentane derivatives of the following formula (I) ##STR1## in which R.sub.1 and R.sub.2 are defined such that when R.sub.1 is a hydrogen atom, R.sub.2 is a hydroxyl group, or R.sub.1 and R.sub.2 are joined to form a ketone are obtained from camphor.The derivatives are synthesized in a simple process from an economical starting material, camphor. The derivatives have woody-note and can be widely used in perfumes, soaps, shampoos, hair rinses, cosmetics and the like.Type: GrantFiled: June 18, 1986Date of Patent: September 15, 1987Assignee: KAO CorporationInventors: Yoshiaki Fujikura, Akira Yamamuro, Motoki Nakajima
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Patent number: 4693844Abstract: A vinylnorbornyl alcohol of 5- or 6-vinyl-2-hydroxymethylbicyclo[2.2.1]heptane which is represented by the following structural formula: ##STR1## The compound has particular fragrance of a mint-like note partaking of camphor tone.Type: GrantFiled: November 22, 1985Date of Patent: September 15, 1987Assignee: Nippon Petrochemicals Company LimitedInventors: Yoshiharu Inoue, Fumio Tanimoto, Hisao Kitano
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Patent number: 4691064Abstract: A method for producing cycloalkanols important as a material for caprolactam, adipic acid and the like, which comprises carrying out the catalytic hydration of a cycloalkene using as a catalyst an aromatic sulfonic acid having at least one hydroxyl or ether group and separating the resulting cycloalkanol from the reaction solution by extraction.Type: GrantFiled: November 12, 1986Date of Patent: September 1, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Tamio Shirafuji, Itaru Kawata
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Patent number: 4681977Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.Type: GrantFiled: June 27, 1985Date of Patent: July 21, 1987Assignee: BASF AktiengesellschaftInventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
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Patent number: 4658056Abstract: A process for the catalytic oxidation of liquid cycloparaffins to oxidation products thereof is disclosed. In the process, partial oxidation products are formed by oxidizing the cycloparaffin with molecular oxygen-containing gas in the presence of an oxidation catalyst comprising two heavy metal compounds. The first heavy metal compound is a cobalt compound having ligands selected from dialkyl phosphate, dicycloalkylphosphate and alkylcycloalkylphosphate, optionally additionally combined with pyridine. The second heavy metal compound is a chromium alkanoate. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] combined with chromium naphthenate.Type: GrantFiled: April 22, 1982Date of Patent: April 14, 1987Assignee: Du Pont Canada Inc.Inventor: Peter A. Sipos
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Patent number: 4631147Abstract: Novel cycloalkan-1-ol derivatives having a formula (I): ##STR1## wherein R represents a hydrogen atom, lower alkyl group or an allyl group, and n is an integer of 3 or 4 provided that when n is 3, R is not a hydrogen atom or lower alkyl group, have a woody, green and earthy odor and may be prepared according to one of the following reaction formulae: ##STR2## where R.sub.1 represents a lower alkyl group or allyl group, M represents MgX or lithium atom, n is a value of 3 or 4, and X represents a halogen atom. ##STR3## The derivatives (I) may be blended with other perfumes to give perfume compositions and thus obtained compositions can be widely applied to various articles which require aromatizing such as perfumes, soaps, shampoos, hair rinses, cosmetics, hair sprays and the like.Type: GrantFiled: February 6, 1986Date of Patent: December 23, 1986Assignee: Kao CorporationInventors: Kiyoshi Matsumoto, Yoshiaki Fujikura, Motoki Nakajima
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Patent number: 4626603Abstract: Aliphatic or cyclic epoxides containing 3 to 8 carbon atoms which are present in aromatic hydrocarbons or halohydrocarbons are saponified continuously and directly to vicinal diols without the use of high temperatures and pressures which would otherwise be necessary. The saponification is acid catalyzed.Type: GrantFiled: November 15, 1985Date of Patent: December 2, 1986Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer
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Patent number: 4613456Abstract: This invention discloses a tricyclo[2.2.1.0.sup.2,6 ]heptane derivative of the general formula ##STR1## where X represents --CH.sub.2 CH.sub.2 -- or ##STR2## and R.sup.1 and R.sup.2 independently represent hydrogen or methyl, a process for preparing the same, and perfume compositions containing the same.Type: GrantFiled: May 17, 1985Date of Patent: September 23, 1986Assignee: Nippon Oil Co. Ltd.Inventors: Mitsuo Matsuno, Teraki Yamanashi, Hitoshi Yuasa, Hirosuke Imai
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Patent number: 4562299Abstract: A process for the preparation of water-soluble vicinal diols by means of a direct catalytic hydroxylation of the corresponding olefines with H.sub.2 O.sub.2. An olefine possibly carrying functional groups inert under the reaction conditions, and whose corresponding vicinal diol is soluble in water, is made to react, under vigorous stirring, with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C. and at a pressure between 1 and 100 atmospheres, in a two-phase aqueous liquid/organic liquid system consisting or consisting essentially of an acid aqueous phase containing H.sub.2 O.sub.2 and of an organic phase containing (1) said olefine; (2) possibly a solvent immiscible with the aqueous phase; and (3) a catalyst of the formula:Q.sub.3 XW.sub.4 O.sub.24-2nwherein Q represents an onium (RR.sub.1 R.sub.2 R.sub.3 M).sup.+ cation, wherein M is chosen from among N, P, As and Sb, and R, R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: December 12, 1984Date of Patent: December 31, 1985Assignee: Montedison S.p.A.Inventors: Carlo Venturello, Mario Gambaro
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Patent number: 4533772Abstract: The process for hydroxylating olefins with oxygen in the presence of water, an osmium-halide (e.g., OsBr.sub.3) catalyst and transition metal containing co-catalyst (CuBr.sub.2) is disclosed.Type: GrantFiled: August 29, 1983Date of Patent: August 6, 1985Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4533773Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an osmium oxide catalyst such as OsO.sub.4, a carboxylate salt co-catalyst, such as sodium acetate, and organic hydroperoxide oxidant is disclosed.Type: GrantFiled: March 22, 1984Date of Patent: August 6, 1985Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4526999Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit lipoxygenase, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: April 25, 1983Date of Patent: July 2, 1985Assignee: Merck & Co., Inc.Inventors: Philippe L. Durette, Timothy F. Gallagher
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Patent number: 4507512Abstract: An improved process for producing an alcohol by hydrating an olefin wherein the improvement comprises hydrating an olefin in the presence of a hydrogen-type catalyst having a silica/alumina molar ratio of 20 to 500 and a solvent using either:A. hydrogen-type mordenite or hydrogen-type zeolite Y, and a sulfone; orB. hydrogen-type crystalline aluminosilicate in which the entrance of the main void is formed by a 10-membered or 12-membered oxygen ring, and a C.sub.2 to C.sub.5 oxy acid or the lactones, lactides, methyl or ethyl esters thereof.Type: GrantFiled: May 14, 1984Date of Patent: March 26, 1985Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Setsuo Kamiyama, Hiroshi Furukawa, Katsumi Kaneko